The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Maynard Webb is truly unique, he has worn 3 different hats and excelled in all of them. First, he is the Founder of The Webb Investment Network, the institutionalisation of his personal investing where he has invested in the likes of Zuora, GOAT, WePay, Okta, PagerDuty and many more incredible companies. He is also a Co-Founder and Board Member at Everwise, the startup that helps companies tailor, scale and run training at enterprise scale. Everwise has raised over $26m in funding from the likes of Sequoia Capital and Canvas Ventures. Finally, Maynard sits on the board of some of the biggest companies of our time including Salesforce and Visa. Previously Maynard was Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay. In Today's Episode You Will Learn: 1.) How Maynard made his way into the world of startups and came to invest in his first company, founded by Sequoia's Jim Goetz and how that led to eBay, LiveOps and more? 2.) Does Maynard believe we have an excess supply of capital in the market today? What does Maynard think of the mega $Bn+ funds being raised on a frequent basis? How does this distort pricing in the market? How does Maynard think about his own price sensitivity? What does this mean for his available reserve allocation? 3.) Does Maynard believe that the dominant role of CEO is management upscaling? How does Maynard advise on the transition from manager to inspirational leader? How do the vest best CEOs hire the very best execs? How does Maynard know when a stretch VP is a stretch too far? How should founders determine and approach "bet the company" decisions? 4.) When should a founder start installing their board? What does Maynard believe is the optimal board construction, both in characters and profiles? How has Maynard seen his own style of board membership changed over the years? What are the best board members talk to listen ratios? How can founders create alignment among their board? 5.) What is the right way for founders to deal with "s*** hit the fan moments"? What is the framework to approach this with? Where do many go wrong in their approach? How does one communicate this to the wider team, investors and board? What have been Maynard's biggest personal learnings here from eBay? Items Mentioned In Today's Show: Maynard's Fave Book: The Better Angels of Our Nature As always you can follow Harry, The Twenty Minute VC and Maynard on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Tavel is a General Partner at Benchmark, one of the world's leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. As for Sarah, Sarah has led Benchmark's investments in and currently sits on the boards of Chainalysis and Hipcamp. Prior to Benchmark, Sarah was a Partner at Greylock Partners, where she led Greylock's investment in Sonder and another (unannounced) company. Before Greylock, Sarah was one of the first 35 employees at Pinterest where she led the company's international expansion and aided in the closing of the Series C financing. Sarah was also the product lead for search, recommendations, machine vision, and pin quality and led three acquisitions as she helped the company scale through a period of hyper-growth. In Today's Episode You Will Learn: 1.) How Sarah made her first foray into the world of venture with Bessemer over 10 years ago? How that led to Pinterest and how she came to be a GP at Benchmark today? 2.) Speaking of Sarah's operating career with Pinterest, Pat Grady said on the show "never has the rate of decay on operating experience been greater". How does Sarah think about and respond to this? How has operating made Sarah a strong investor? What are the drawbacks that this operating experience can present for investors? 3.) Moving to evaluation, Andy Rachleff, Founder @ Benchmark said on the show, "good team poor market, market wins; good market, poor team, market wins. How does Sarah think about the balance between founder vs market? Why is going after big markets so hard? What should investors look for in a market with that in mind? How does Sarah determine the right time to open up adjacent markets? 4.) There has never been a greater supply of capital in the market than today, does Sarah believe we have an excess supply today? Does Sarah agree with her Partner, Peter Fenton, "no good deal is too expensive in hindsight"? How does Sarah assess her own price sensitivity? How does it depend on the opportunity? How has it changed over time? 5.) Having 2,5000 hours on boards, how has Sarah seen herself develop and change as a board member? What have been some of the biggest learning curves? What are the commonalities in the very best board members Sarah works with? how doe the best entrepreneurs manage and use their boards effectively? 6.) Why does Sarah think that crypto today is very much like the world of adtech in the early days? How does Sarah think about the requirement for specialisation in the space? WIll this be a game for the specialised crypto funds or can generalist VC funds compete? Items Mentioned In Today's Show: Sarah's Fave Book: Creating the Kingdom of Ends Sarah's Most Recent Investment: Hipcamp As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Amol Deshpande is the Co-Founder and CEO at Farmers Business Network, the farmer-to-farmer agronomic information network improving the livelihood of farmers by making data useful and accessible. To date, they have raised a whopping $193m in funding from the likes of Kleiner Perkins, T Rowe, GV, Temasek and more. As for Amol, prior to FBN, he was a Partner @ Kleiner Perkins where he invested in the likes of Harvest Power and Agilyx and before Kleiner, Amol was a Director @ Black River Asset Management. In Today's Episode You Will Learn: 1.) How Amol made his way into the world of startups, came to be a Partner @ Kleiner Perkins and then came to change the world of farming with Farmers Business Network? 2.) What were Amol's biggest takeaways from his time with Kleiner? Although important to think really big, how does Amol think about the Peter Thiel School of Thought, starting in a very small niche and expanding? Where does Amol see many founders go wrong when it comes to market size and assessment? 3.) How does Amol believe the very best CEOs hire the very best talent? What core characteristics does Amol look for when adding to his exec team? What are the leading questions and indicators that would excite/concern Amol? Why does Amol believe the smartest people do not always make the best hires? What are the core signs that a stretch VP is a stretch too far? 4.) What is the key to success for founders in building credibility with customers, investors and their board? What is the most challenging element of credibility building? Where does Amol see many founders go wrong and lose credibility today? How does your approach have to alter according to which class of individual you are looking to build with? 5.) How does Amol fundamentally approach the topic of capital efficiency? What does Amol believe is the right way for founders to think about dilution when raising? How does Amol determine when is the right time to raise big and pour fuel on the fire? Items Mentioned In Today's Show: Amol's Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln As always you can follow Harry, The Twenty Minute VC and Amol on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Frankel is Managing Partner @ Founder Collective, one of the leading seed funds of the last decade with a portfolio including the likes of Uber, PillPack, Coupang, Hotel Tonight, Venmo, Buzzfeed and many more incredible companies. David himself sits on the board of PillPack, Olo, Adhawk and SeatGeek. Prior to founding Founder Collective, David was the Co-Founder and CEO of Internet Solutions, one of the largest ISP providers in Africa. This led to his entrance into angel investing where he enjoyed immense success investing in the likes of Chris Dixon's Hunch and Alex Rampell's TrialPay, just to name a few. In Today's Episode You Will Learn: 1.) How David made his way into the world of startups and angel investing from founding Africa's largest ISP provider and how that led to his founding of Founder Collective? 2.) Does David agree with Andy McLoughlin on the inherent mindset shift required when moving from angel to institutional investor? What does David believe is the key to making a new venture partnership work well in the early days? How was the process between him and Eric Paley? What were some of the core challenges/ highlights and breakthroughs? 3.) What does founder-market fit truly mean to David? Why does David believe it is one of the most crucial elements to look for in all investment opportunities? How was this so perfectly evident in the case of Elliot and TJ @ PillPack? How does David navigate the balance between the perfectness of the fit and the investability of the market? 4.) From watching TJ and Elliot at PillPack, what does David believe the truly special founders do to continuously attract the best talent? When does David believe is the right time to really build out the exec team? How did Elliot and TJ align their scaling of the org chart with the growth of the business so well? 5.) How does David think about the lack of free and open distribution in acquiring new customer in a capital efficient manner today? Why does David believe the companies of the future will be advantaged in distribution? In what shape and form can this advantage take? How does David think about the right time to put the pedal to the metal and aggressively grow? Items Mentioned In Today's Show: David's Fave Book: Sapiens: A Brief History of Humankind David's Most Recent Investment: Adhawk As always you can follow Harry, The Twenty Minute VC and David on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Howard Lerman is the Founder & CEO @ Yext, the company that allows you to control your brand experience across the digital universe. Due in part to Howard's incredible leadership of the firm, Yext went public in April 2017 with an opening price of $11 a share, today the stock price sits at $26.85 and a market cap of $2.65Bn. Prior to the IPO, Yext raised over $117m in VC funding from Insight Venture Partners, IVP, SV Angel and CrunchFund to name a few. As for Howard, Yext is his 4th company and he is also Co-Founder and Chairman of Confide, a leading off-the-record messaging service. In Today's Episode You Will Learn: 1.) How Howard made his way into the world of startups and came to Partner with is co-founders to start the now public company that is Yext? 2.) Why must every founder know about Teddy Roosevelt and his "Five Minute Meetings"? Literally, what is the right way to structure these meetings? What one question is the right question to ask? How can a leader look to retain that startup culture and ethos with scale? Why does Howard believe running a global company is like running a country? 3.) What have Howard's biggest takeaways been from studying "John Lennon's Storytelling Trick"? How can founders use this trick both to inspire their team more effectively internally and then to present a better vision for the company, externally? 4.) Howard has said before "fundraising is not an end in itself". Does Howard believe that company financing should be celebrated? How was the IPO process for Howard? From a literal standpoint, how does the process run? How did Howard choose which banks to work with? How did the 10-day roadshow shape up? How did the pricing decision-making process look the night before IPO? 5.) Why does Howard believe it is fundamentally better being a public company? What does "public" status allow you? How does being public introduce a challenge never before seen to founders? Why must founders always examine the motives of the VC behind whether they are pushing them to remain private or go public? Items Mentioned In Today's Show: Howard's Fave Book: Five Stars: The Communication Secrets to Get From Good to Great As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shabih Rizvi is the Founding Partner @ Gradient Ventures, Google's new AI-focused venture fund, which will invest in and connect early-stage startups with Google's resources, innovation, and technical leadership in artificial intelligence. Prior to Gradient, Shabih was a Partner at KPCB, where he was actively involved with investments in TrueCaller, Mobcrush, Veem and Ujet. In addition, he helped the firm build their seed program and served as advisor to Flipagram and Victorious. Before KPCB, Shabih founded and led the startup outreach program for Google Play. Prior to Google Play, Shabih worked on the Mobile Apps Lab team which built SMB products. His primary focus was scaling TalkBin (Acquired by Google) to enterprise clients. Shabih joined Google after Google's acquisition of AdMob, where he was a manager on the Business Development team. In Today's Episode You Will Learn: 1.) How Shabih made his way into the world of venture with Kleiner Perkins and how he came to be a Founding Partner @ Google's AI focused venture fund, Gradient? What were Shabih's greatest lessons from working side by side with John Doerr? 2.) Shabih has said to me before "founder relationships and their longevity really matter". What does Shabih mean by this? How has this played out for Shabih in an investing environment? What have been Shabih's subsequent learnings? 3.) How does Shabih identify the "3 buckets" that VCs source from? How does Shabih look to filter through opportunities at scale? What must he see in the deck? What are his quick no's? What is Shabih's framework for saying no both with efficiency and kindness? Why does Shabih believe this is one of the hardest parts of the role? 4.) What does the internal investment decision-making process look like at Gradient? Why do they believe that 2 partner meetings a week is optimal? Prior to that, how does Shabih structure his meetings with founders? Why does Shabih believe it is so important to go to them at their HQ? Should all investors go to the founder? 5.) Why is Shabih a strong believer in the decentralisation of talent away from the valley? What are the primary drivers for this decentralization? How does Shabih think about pricing in different regions? To what extent does it differ wildly? How does Shabih respond to traditional SaaS wisdom that you have to build your SaaS business in the valley? Items Mentioned In Today's Show: Shabih's Fave Book: Measure What Matters, When Breathe Becomes Air Shabih's Most Recent Investment: Scotty.ai As always you can follow Harry, The Twenty Minute VC and Shabih on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Andrew Farah is the Founder & CEO @ Density, the startup that measures real-time occupancy of every room in your office. To date, they have raised over $16m in funding from some great friends of the show in the form of Founders Fund, Mark Suster @ Upfront, Ludlow Ventures, Jason Calacanis, Hiten Shah and Arjun Sethi, just to name a few. As for Andrew, prior to founding Density, he was a Managing Partner @ Rounded, a software development agency & product studio. There, Andrew and the team built the first Density prototype. In The Show Today: 1.) How Andrew made his way into the world of technology and product with Rounded and came to found the people counter of the next generation in Density? 2.) How does Andrew view the role of super-connectors today? What specific time has a super-connector really moved the needle for Andreq and changed the trajectory of Density? What can one do to first build relationships with these people? What can be done to sustain that relationship and really engage and deepen it? 3.) How does Andrew view the importance of "employee retention" in the ultimate success of a company? Density have never had an employee leave in 4 years, what does Andrew believe they have done right? What has not worked for them? What does he mean when he says, "the best leaders answer employees questions before they are asked"? 4.) What has Andrew found to be the commonalities in the truly special VCs? What do they do that makes them so special? How do they view the world and the assessment of companies that is so right? How does Andrew think about investor selection? Where does Andrew see many founders going wrong with this? 5.) Why does Andrew think that so many hardware startups fail today? What do they consistently underestimate and not understand? What are the core challenges in building a global supply chain? How does one have to think about cost of goods (COG) and unit economics when scaling hardware startups? Items Mentioned In Today's Show: Andrew's Fave Book: The Idea Factory: Bell Labs and the Great Age of American Innovation As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Casper, the company that deliver a great night's sleep at an incredible value. The team of engineers at Casper works nonstop prototyping, collecting data, and engineering what is certainly the most comfortable mattress. The Casper mattress has a unique combination of foams that provide the right pressure relief and alignment, so you feel perfectly balanced and comfortable. Try Casper yourself for 100 nights in your own home – RISK FREE. If you don't love it, they come pick it up and refund you everything, no questions asked. Go to casper.com to try yours for 100 nights with FREE shipping and returns. Use code 20VC to save $50 on select mattresses today. Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it's easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Barry Eggers is a Founding Partner @ Lightspeed, one of the world's leading venture funds with a portfolio that includes the likes of Snapchat, Mulesoft, Affirm, StitchFix, AppDynamics, Nutanix and many more incredible companies. Barry himself has led investments in Snapchat, Metasolv Software (acquired post-IPO by ORCL), Calista Technologies (acquired by MSFT), Arbor Networks (acquired by DHR), Growth Networks (acquired by CSCO). As a result of his incredible success, Barry has been named to Forbes Midas List numerous times. Prior to VC, Barry held executive roles at Cisco Systems where he established many of the company's largest distribution channels across OEMs, Service Providers, Distributors, and VARs. He also developed Cisco's initial M&A process and directed the first wave of acquisitions and integrations for the company. In Today's Episode You Will Learn: 1.) How Barry made his way from the world of Cisco to the wonderful world of venture and came to found one of the most successful firms of the decade in Lightspeed? 2.) How does Barry break up the development of the venture ecosystem into 3 distinct stages? What does Barry believe have been the positive changes? What does Barry believe have been the negative changes? Does Barry believe there is an excess supply of capital today? Why does Barry believe there are too many first time funds? What is the outcome? 3.) Did Barry always aim to build the multi-stage, multi-geography firm that he has built with Lightspeed, from the start? What have been the fundamental inflexion points for Lightspeed both in the increase in brand value and liquidity to LPs? Why does Barry believe building a firm really is an art? What should managers most look for in their first LPs? 4.) What does Barry believe are the 3 ways a venture firm can fail in a generational transition? How can firms incentivise young partners to see the career path and trajectory ahead? What must the older partners at the firm be willing to do? What have been Barry's biggest lessons in their successful generational transition? 5.) Barry has sat on boards for over 21 years, how has Barry seen himself develop and evolve as a board member over time? What makes a truly functional board? What are the best practices? Who is the best board member Barry has ever sat on a board with? What makes Jim Goetz such a special board member? Items Mentioned In Today's Show: Barry's Fave Book: Quantum Computing: A Gentle Introduction (Scientific and Engineering Computation) Barry's Most Recent Investment: Audius As always you can follow Harry, The Twenty Minute VC and Barry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Philip Krim is the Founder & CEO @ Casper, the global sleep company that launched in 2014 offering perfect mattresses directly to consumers. Since then they have raised over $239m in funding from the likes of NEA, Lerer Hippeau, IVP, Norwest Venture partners and even include Leonardo Di Caprio on their cap table. As for Philip, he is a serial entrepreneur having founded 2 previous startups, launching his first business out of his very own dorm room at the University of Texas. Due to his immense success, he has been profiled in The New York Times, The Wall Street Journal and been awarded a TechCrunch Crunchie award for Best in E-commerce. In Today's Episode You Will Learn: 1.) How Philip made his way into the world of startups and came to launch one of the most successful consumer brands of our day in the form of Casper? 2.) We continuously hear about "the end of retail". What does retail done poorly mean to Philip? How does he perceive the future of retail and retail done right? How does retail fundamentally change the margin structure of an originally online brand like Casper? What does Philip perceive to be the biggest challenge to opening up retail significantly? 3.) Why does Philip think we have seen many online mattress brands struggle over the past year? How has this affected how he operates and executes the plan with Casper? How does Philip think about diversification within customer acquisition channels? How does Philip assess the saturation rate of different distribution channels? 4.) Casper's latest lead investor was a strategic investor, Target. How does Philip think about accepting strategic funds? What was the internal debate and decision-making process? What advice would Philip have to founders contemplating accepting strategic money? How can strategics sometimes have ulterior motives? 5.) Does Philip agree with many former CEOs on the show, the most important role of the CEO is management upscaling? What other functions does Philip consider core? How did Philip think about building out the core of his C-Suite? Does he wish he had done it earlier? What element of the C-Suite was the hardest to hire for? Items Mentioned In Today's Show: Philip's Fave Book: Elon Musk: How the Billionaire CEO of SpaceX and Tesla is Shaping our Future, Bad Blood: Secrets and Lies in a Silicon Valley Startup As always you can follow Harry, The Twenty Minute VC and Philip on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Daniel Gross is the Founder @ Pioneer and the Head of AI @ Y Combinator. Taking them in turn, Pioneer is the home for ambitious outsiders of the world where they are building a community of creative young people working on interesting projects around the globe. YC is obviously the world's most successful accelerator with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport and many more incredible companies. Prior to Pioneer and YC, Daniel was a Director @ Apple where he focused on machine learning, as a result of his prior company, Cue (also a YC company) being acquired by Apple in 2013. Finally, Daniel also has one of the valley's most impressive angel portfolios with investments in OpenDoor, Cruise (acquired by GM), Gusto and Github, just to name a few. In Today's Episode You Will Learn: 1.) How Daniel made his way from a military camp in Israel to start a company at YC to selling the company to Apple to now, creating a global community of the world's most ambitious people? 2.) What does Daniel believe is the commonality of truly great people? Why did Daniel decide to start Pioneers now? What are the terms for entering Pioneers? How is Daniel looking to create the global talent engine through gamification with Pioneers? Why is gamification such a strong tool to understand human motivation? 3.) Why did Daniel decide it was the right decision to bring the Pioneers to SF? In the world of decentralized entrepreneurship, why did Daniel feel it necessary to bring everyone to the valley? What does Daniel believe Silicon Valley needs to solve if it is to become the home for crypto and frontier tech? What role does optimism play in the success of SF? 4.) The program is funded through Stripe and Marc Andreesen, many have suggested this poses conflict with potential optionality on projects and talent, how does Daniel think about this conflict? Why is it not a concern? What other challenges does Daniel forsee as being the biggest barriers to the success of Pioneer? 5.) How does Daniel think about KPI's for the coming 12 months? What are his core KPI's? How does Daniel construct a framework that will allow him to love previously disliked tasks? How can anyone do this with success? Items Mentioned In Today's Show: Daniel's Fave Book: Finite and Infinite Games, Enders Game Daniel's Most Recent Investment: Jump, Retool As always you can follow Harry, The Twenty Minute VC and Daniel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Joist has built the go-to platform for contractors. Joist enables contractors to professionally handle everyday tasks like estimating, invoicing, collecting payments, and manage projects, while also helping them grow their businesses as a streamlined CRM. More than 500 thousand contractors have used the Joist platform to manage more than $8.5 billion in invoiced work in North America, the UK, and Australia. Learn more at joist.com. WePay's got a great case study about how another platform, TeamSnap, is working with WePay to make payments its #1 revenue stream… more than its subscription business. Get it at wepay.com/harry. Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it's easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.

Heather Fernandez is the Founder & CEO @ Solv, the startup that simplifies everyday healthcare by providing access to high quality, last-minute care. To date, Heather has raised over $23m in funding from some of the great of the world of venture including Bill Gurley @ Benchmark, Theresia @ Aspect, James Slavet @ Greylock and Pete Flint @ NFX. Prior to Solv, Heather was part of the early team @ Trulia, where she led advertising product, marketing, and sales strategy and saw the team go from 20 people through to the $2.5B acquisition by Zillow Group. Before Trulia, Heather was at Morgan Stanley and more interestingly was National Deputy Press Secretary for Senator John McCain's 2000 presidential campaign. If all of that was not enough, Heather is also a Board Member at the global behemoth, Atlassian. In Today's Episode You Will Learn: 1.) How Heather made her way into the world of startups from the world of politics? How she came to be one of the early team at Trulia? What was the a-ha moment for Solv? 2.) How does Heather fundamentally define "culture"? What is the trust equation? Why does it play such a central role in successful culture building? What does Theather mean when she discusses "constructive candor"? What are the common mistakes Heather sees founders make when it comes to scaling culture? What literal actions can be done to instil trust and respect within the team? 3.) Does Heather agree with James @ ThredUp, "marketplaces founders have to be immensely stubborn"? Would Heather agree with Leah @ TaskRabbit with regards to marketplace NPS and "one side of the equation will always be less content"? 4.) What advice would Heather give to managers to maximize their impact in their organisation and their career? How does Heather think about bringing in the right people at various stages of the company? How does it change with scale? On funding, Solv has raised $23m, how does Heather think about when is the right time to pour fuel on the fire? 5.) Heather is also on the board of Atlassian, so what are the core benefits of simultaneously sitting on a board and managing your own board? What have been Heather's biggest learnings from her time on the Atlassian board? How do the best founders manage their boards successfully? Items Mentioned In Today's Show: Heather's Fave Book: The American Political Tradition and the Men Who Made it As always you can follow Harry, The Twenty Minute VC and Heather on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Avichal Garg is the Managing Partner @ Electric Capital, one of the leading crypto asset management firms today investing in both liquid and illiquid tokens that are emerging stores of value and rooted in novel technology. Prior to Electric they personally invested in Coinbase, Bitwise, Basecoin and more. As for Avichal as well as Electric, he is a part-time partner at YC and prior to YC, he was Director of Product Management at Facebook where he led the Local product team (a $3.5Bn line of business at the time). Before FB, Avichal worked on Search and Ads at Google, started and sold a few companies, and invested in startups including Optimizely, Boom, Color, Cruise, Instawork, CaseText, and many more. In Today's Episode You Will Learn: 1.) How Avichal made his way into the world of startups, began angel investing, discovering the power of crypto and why now for Electric Capital? 2.) How does Avichal break the world of crypto into 4 fundamentally distinct buckets today? Which 2 elements does Avichal believe will be the biggest value accruers? What is the core question to ask when assessing a crypto opportunity today? How does angel investing compare to crypto investing? 3.) Where are the majority of ICO dollars going today? Why does Avichal believe that ICOs in large part do not fundamentally make sense from an investment and pricing perspective? How does Avichal think about liquidity in the world of crypto? As an institutional manager, what mindset does Avichal embrace when liquidity is possible? 4.) Why does Avichal believe that regulation and government controls is the opposite of the real risk to the space? If this is not the biggest risk, what does Avichal believe is the biggest risk to the potential of the space? Why does Avichal believe that the US government have handled the space with nuance and intellect? 5.) Why does Avichal believe that decentralized teams will not work? How does this correlate to the progression of platform complexity with time? Why does Avichal believe this will lead to the re-centralization of talent back to Silicon Valley? What catalysts will act to speed this up or hamper it's re-centralisation? Items Mentioned In Today's Show: Avichal's Fave Book: Ender's Game Avichal's Most Recent Investment: Coda Cryptocurrency Protocol As always you can follow Harry, Avichal and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Dylan Serota is the Founder & Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service. They recently raised a phenomenal $13m Series A with some of the world's most renowned names including Lightspeed, KPCB, Craft, Thiel, Atomic and Jerry Yang just to name a few. As for Dylan, he is also a Founder-in-Residence @ Atomic, one of the valley's most exciting new institutions which both founds and funds companies and includes the likes of Hims, TalkIQ (acq by Dialpad) and more. Prior to Atomic and Terminal, Dylan was Head of Platform @ Eventbrite where he led platform product org, built third-party developer ecosystem and platform partnerships. In Today's Episode You Will Learn: 1.) How Dylan made his way into the world of startups with Eventbrite and how that led to his realisation on the future of development operations with Terminal? 2.) Why does Dylan believe that it is important for startups to build distributed teams earlier in their growth curve than often suggested? What are the key aspects to making remote teams work well? Why does Dylan believe that "companies overvalue their culture"? How does Dylan assess culture across remote teams? 3.) Jason lemkin says "startups can either hire a stretch VP or a burnt out mediocre VP", does Dylan agree with this? How does Dylan assess the balance between hiring functional specialists vs jack of all trades? When is the right time to make the transition from generalist to specialist? 4.) Hw does Dylan analyze and assess a startup leaderships team ability to adapt and prioritize speed? What is key to successful decision-making today in startups? How does Dylan think about the importance of speed when it comes to product ideation and iteration? 5.) What does Dylan believe is the biggest mistake many people make early in their career? What are the commonalities of the truly successful people in how they have structured their careers? How does Dylan think about the balance between title vs salary vs experience? What should one optimise for and when? Items Mentioned In Today's Show: Dylan's Fave Book: The Selfish Gene by Richard Dawkins As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Jeff Fagnan is Founding Partner @ Accomplice, one of the East Coast's leading early-stage funds with a portfolio including the likes of AngelList, PillPack (acq by Amazon), Freshbooks, Hopper, Secret Escapes and many more incredible companies. Accomplice is also unique as it is a platform builder creating incredible initiatives such as Spearhead, Maiden Lane and Boston Syndicates, really moving the needle in seeding local ecosystems. As for Jeff he is well known as a founding investor, working with most of his portfolio since inception, sometimes as a co-founder including Veracode (Sold to CA Technologies‍). Jeff also sits on the board of AngelList, PillPack, InsightSquared, Hopper, Freshbooks and more. In Today's Episode You Will Learn: 1.) How Jeff made his way into the world of VC from consulting over 18 years ago? How did his experience of the bubble influence Jeff's mindset and thinking? 2.) What did Jeff learn about building an optimal venture partnership with the transition from the 23 partner Atlas to the tight-knit Accomplice? Where does Jeff believe most venture partnerships go wrong today? What does Jeff believe is the right size partnership in venture? Why does Jeff believe that partners are there to save each other from themselves? 3.) How did Jeff's experience with Atlas effect his views on portfolio construction? Why does Jeff advocate for the model of raising $200m every 2.5 years for a pure seed strategy? How does Jeff think about building an effective reserve strategy? Why does Jeff not believe pro-rata should be guaranteed? Why does Jeff believe force ranking a portfolio is dangerous? 4.) Jeff believes the best VCs are able to manage 2 things, what are those 2 things? From his 18 years on boards, what does Jeff believe makes the truly special board member? Who is the best he has worked with and why? How does Jeff look to gain the balance of being both proactive to opportunities and reactive to inbound? 5.) Accomplice has recently made it's foray into the West Coast, what was the thinking behind that move? How does Accomplice think about establishing mindshare as a new entrant in a hotly contested environment? What does Jeff believe is the key to successful geographic expansion in venture? Items Mentioned In Today's Show: Jeff's Fave Book: Where The Wild Things Are Jeff's Most Recent Investment: Perch As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Armon Dadgar is the Founder & CTO @ Hashicorp, the open-source software company that provides consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, Hashicorp has raised over $74m in VC funding from many friends of the show including Scott Raney @ Redpoint, Glenn Solomon @ GGV, Semil Shah, True Ventures and Mayfield. As for Armon, today he leads the Hashicorp research group and focused on industrial research in the security and large-scale system management space. Prior to founding Hashicorp, Armon was a software engineer @ Kiip and Amazon. In Today's Episode You Will Learn: 1.) How Armon made his way from intern at Amazon to founding Hashicorp and creating the game-changing suite of tools in the world of DevOps? 2.) Hashicorp has enjoyed success after success with new products, so what does Armon believe is the secret to continuous product innovation? What does Armon mean when he says "there are really 3 phases to product adoption"? How does Armon determine between vision for a product and the realism when it is not working, when launching products? 3.) Hashicorp only recently started generating revenue, why was now the right time? At what point does one go from building products for the community to building products people will pay for? How does Armon assess professional services today? What does Armon believe are the 2 foundational problems with "professional services"? 4.) Many VCs suggest it's impossible to build big infrastructure businesses today given the commoditizing forces to open source and cloud computing. How have Hashicorp navigated that and bucked that conventional wisdom? How has Armon also bucked the conventional wisdom on the importance of focus? What core tenets must remain if one wants to go against this emphasis on focus? 5.) Armon and his co-founder brought on a CEO early, what was the realisation moment for the need to bring in an external CEO? How did Armon look to get comfortable with this transition? What advice would Armon give to founders contemplating bringing in an external CEO? With the benefit of hindsight, what would Armon do differently if he had the time again? Items Mentioned In Today's Show: Armon's Fave Book: To The Lighthouse by Virginia Woolf As always you can follow Harry, The Twenty Minute VC and Armon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Nick Brown is Managing Partner @ Imaginary, founded alongside Net-A-Porter founder, Natalie Massenet, Imaginary invests in early–stage opportunities at the intersection of retail and technology. Included in their incredible portfolio is the likes of Glossier, Daily Harvest, Farfetch, Everlane and many more awesome companies. Prior to co-founding Imaginary, Nick was a Partner at 14W Venture Partners where he invested in the likes of Goop, Outdoor Voices, The Real Real and Business of Fashion just to name a few. Before that Nick was Head of New Media @ NV Investments. In Today's Episode You Will Learn: 1.) How Nick made his way into the world of venture and consumer investing from the days of investment banking? 2.) We have seen an explosion in the world of consumer with regards to D2C brands, does Nick believe we are in a D2C bubble? There is a lot of skepticism around physical product companies being venture businesses, so what are the core considerations for Nick when investing in physical product brands today? 3.) Having backed the likes of Glossier, Farfetch, Everlane etc, what does Nick believe are some of the leading indicators from the early days whether a company has a sustaining and authentic brand? What does Nick believe is the future for direct to consumer of the next 24-36 months? What is he most excited by? 4.) How does Nick think about the interaction between D2C brands and wholesale and physical retail? When is the right time to pull the wholesale lever? What does Nick believe is a healthy ratio between paid to organic customer acquisition? What are the commonalities in the consumer brands that have broken out within his portfolio? 5.) In terms of character traits, what commonalities does Nick see in the most successful consumer founders he has backed today? We have seen a rise in the celebrity founder over the last few years, so what is the role of the celebrity founder? When does it work? When does it not work? How does the future of celebrity founder look to Nick? Items Mentioned In Today's Show: Nick's Fave Book: To Kill A Mockingbird Nick's Most Recent Investment: Fitplan As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Adam Goldberg is a Partner @ Lightspeed Venture Partners, one of the world's leading funds with a portfolio including the likes of SNAP, Mulesoft, Max Levchin's Affirm, AppDynamics and many more incredible companies. As for Adam, at age 13, Adam enrolled as a full-time student at UC Berkeley, where he studied pure and applied mathematics and conducted research in number theory and machine learning. He went on to work as a mathematician for the Department of Defense and as a researcher Berkeley, Wisconsin-Madison and Stanford. Following that, Adam worked as an engineer at Palantir and Dropbox and was an early product manager at Rubrik. In 2016, Adam left Rubrik to become a partner at Lightspeed where he has invested in the likes of Basis, Vector and Totemic Labs, just to name a few. In Today's Episode You Will Learn: 1.) How Adam made his way into the world of venture from the department of defence and working at titans such as Palantir and Dropbox? 2.) Why does Adam believe the rate of founder learning is the most important skill that an investor can evaluate and assess? What does optimizing for learning really mean to Adam? In practice, what can one do to optimize for learning? What are the common traits and signs of those founders that do this well? 3.) Why does Adam believe that there remains today no mass market decentralised consumer product? What is needed for this to happen? How does Adam forsee the development of token economics over the coming years? What novel token financing solutions does Adam respect? What is required within token economics for Adam to gain real comfort? 4.) Why does Adam believe that the Telegram ICO got such attention? Why is Adam fundamentally bullish on the opportunity? What 2 core characteristics does Telegram have that are required for crypto projects to be successful? On the other side of the table, where is there cause for concern when reviewing the opportunity? 5.)How does Adam think about "betting on fundamental trade-offs in crypto"? What are the 4 key trade-offs that founders must contemplate? What are the trade-offs that Adam is willing to accept vs not accept? How does Adam envisage the willingness to accept trade-offs so widely, change over time in the space? Items Mentioned In Today's Show: Adam's Fave Book: Flowers for Algernon Adam's Most Recent Investment: Strangeworks As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Eddy Lu is the Co-Founder & CEO @ GOAT, the largest marketplace in the world for buying and selling authentic sneakers. To date, GOAT have raised over $97m in VC funding from some of the best in the business including Accel, Index, Upfront and include angel investments from Elad Gil, Ashton Kutcher and Alexis Ohanian. Prior to GOAT, Eddy enjoyed numerous different roles including founding a chain of Japanese dessert stores building a slew of different 99c apps and started on Wall St with Lehmann Brothers and Deloitte. In Today's Episode You Will Learn: 1.) How Eddy made his way from Wall St to making 99c apps to creating a chain of Japanese desert stores to founding the world's largest sneaker marketplace in GOAT? 2.) Pivoting from social dining to sneaker marketplace, how does Eddy determine between mission and passion for the vision vs when something is simply not working? What core metrics made Eddy realise this pivot was needed? How did Eddy communicate the pivot to the existing investor base? How did he get them on board for the next chapter? 3.) Over the years, GOAT has had many investors wanting to invest, how does Eddy approach investor selection? What advice does Eddy have on optimising for valuation and the terms that founders should really focus on? What have been the biggest lessons from having former Twitter COO, Adam Bain on the GOAT board? 4.) Does Eddy agree with Paul at Canvas that marketplace founders should give up if they do not have differentiated supply? What does Eddy believe is the core characteristic of the most successful marketplaces? To what extent does Eddy believe that early marketplaces must rely on existing distribution and offline activities to scale? 5.) Eddy took the decision to merge with Flight Club, what was behind the decision to open up the business to physical retail? Why does Eddy believe that physical retail does not affect the margin structure massively when compared to it's online counterpart? How does Eddy assess the categories that make sense for physical retail between those that do not? Items Mentioned In Today's Show: Eddy's Fave Book: Crime and Punishment As always you can follow Harry, The Twenty Minute VC and Eddy on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Jason Stoffer is Managing Partner @ Maveron, the consumer-only venture fund backing a new breed of brands. Their stellar portfolio includes the likes of eBay, Zulily, General Assembly, Allbirds and Dia&Co, just to name a few. As for Jason, Jason is the master of all things consumer education, e-commerce and marketplace businesses. He has been a Board Member of a number of category-leading consumer businesses, such as zulily (Nasdaq: ZU), General Assembly (acquired by Adecco), Common and more. Prior to Maveron, Jason was Senior Director of Strategic Operations at Career Education Corp where he saw the business scale to a market cap of over $4.5Bn. In Today's Episode You Will Learn: 1.) How Jason made his way into the world of VC from the world of journalism? What were his biggest takeaways from seeing the boom and bust cycle of 2001 and 2008? 2.) Why does Jason believe that moats matter as much, if not more than brand today? How can founders look to create the strongest form of defensibility? How does Jason analyze the 2 paths for consumer businesses today; raise large amounts of capital and buy growth or raise little, grow slowly, understand unit economics and channels over time? Does Jason think we will see a graveyard of immensely funded consumer businesses? 3.) How does Jason view paid acquisition today? Does Jason agree with Peter Fenton. "there is a lack of free and open distribution in consumer today"? When does Jason believe that consumer founders should really focus on CAC/LTV? What metrics really matter in the early days for consumer? How does Jason analyse acquisition channel mortality? When does he mean when he says, "CAC works, until it does not"? 4.) Jason has said before that "VC is a struggle". What elements does Jason find most challenging? How does Jason deal witht he shit hit the fan moments as a VC? Can VCs in this hyper-competitive world be openly vulnerable in Jason's eyes? How has Jason seen his approach to hard and challenging situations in VC develop over time? 5.) Does Jason believe we are in a consolidatory environment today or will we see the next generation of mega consumer brands being built? When investing, does Jason ask, who is the potential acquirer? Why? What multiple is achievable? Would Jason agree with Kirsten Green that "Amazon does more to make the market than destroy it"? How does Amazon affect Jason's investment philosophy and approach? Items Mentioned In Today's Show: Jason's Fave Book: 100 Years of Solitude Jason's Most Recent Investment: Imperfect Produce As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. Find out more on cultureamp.com.

Fritz Lanman is the CEO @ ClassPass, the startup that provides the most flexible fitness membership ever. To date, they have raised over $154m in VC funding from the likes of Thrive, GV, CRV, Fifth Wall and Temasek just to name a few. As for Fritz, prior to ClassPass he was the Founder & CEO @ Livestar, a mobile recommendations startup that was acquired by Pinterest. Before that, he was a Senior Director in the Corporate Strategy Group @ Microsoft where he led several multi-billion dollar M&A evaluations and strategy projects including the Facebook investment and Yahoo deal. If that was not enough, Fritz is also a tremendously successful angel with a portfolio including the likes of Square, Pinterest, Wish, Flexport, Everlane and 75 or so more companies. In Today's Episode You Will Learn: 1.) How Fritz made his way into the world of startups with Microsoft? How that led to angel investments in Wish, Flexport, Square and more? How he came to be CEO @ ClassPass? 2.) How did the $250m Microsoft investment in Facebook come about? What made Fritz so confident he told Steve Ballmer he was willing to bet his career it would be a $10Bn company? What was the decision-making process internally around that deal? 3.) How does Fritz assess his own asset allocation strategy? Why does Fritz not agree with thesis-driven angel investing? When starting angel investing, how did he approach portfolio construction? Why does Fritz believe it is immensely synergistic to be both an operator and angel? As a result, how does Fritz approach placing investors in a quadrant between helpfulness and high maintenance? 4.) Why does Fritz believe that your investor cannot be your recruiter? What have been Fritz biggest learnings on continuously attracting the best talent? Why does Fritz believe that it is BS that one should not celebrate fundraising? Ultimately, what does Fritz elieve fundraising signifies? 5.) ClassPass has expanded to 34 markets over the last few years, how does Fritz determine when is the right time to pour fuel on the fire? What are the 2 fundamental questions one must ask before you do? Does Fritz believe that aggressive growth and capital efficiency are mutually exclusive? How does Fritz think about capital efficiency with ClassPass today? Items Mentioned In Today's Show: Fritz's Fave Book: Endurance: Shackleton's Incredible Voyage to the Antarctic As always you can follow Harry, The Twenty Minute VC and Fritz on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Elad Gil is the Founder @ Color, the startup that shows you your genes can help you make better health decisions. They have raised over $112m in funding from the likes of General Catalyst, CRV, 8VC, Aaron Levie and more incredible names. Elad is also an incredible angel, counting the likes of Airbnb, Stripe, Optimizely, Opendoor and Wish all in his portfolio. Now Elad is adding a new string to his very talented bow with the release of his book, High Growth Handbook, published by Stripe in which Elad interviews 14 leaders from the valley from Marc Andreesen to Reid Hoffman to Patrick Collison. Plus shares his own experiences from Google, growing from 1,500 to 15,000 and Twitter, growing from 100 to 1,500. Not only is this the first book I have read voraciously from cover to cover in a long time but it is now outselling Zero To One and Lean Startup as pre-order. In Today's Episode You Will Learn: 1.) How Elad made his way into the world of startups, came to found 2 companies that sold to Twitter and Google and came to invest in Airbnb, Stripe, Wish etc? 2.) How does Elad define the role of the CEO today? What are the commonalities in those truly great CEOs? How do the very best CEOs hire the very best execs? How do they address role allocation internally? How do they determine between employees that do and do not scale with the firm? Where do CEOs make the most fatal mistakes in high growth startups? 3.) Why are pre-emptive rounds so common today? Why does Elad believe many people will lose a lot of money in them? What advice does Elad give to founders when they are an option? Does Elad believe the lack of liquidity is good for venture this cycle? How does Elad assess the emergence of megafunds? How does this alter and distort the market? 4.) With regards to market share, how should founders prioritise between pricing and market share? Is cash ever a defensible moat? What does Elad mean when he says that "too many people are stuck on Amazon as the winning model"? Why does Elad believe that margins and capital leverage are the unsung heroes of tech? 5.) Why does Elad believe we have seen such a reduction in M&A? Why do many founders not fully assess the financial benefits of being bought by a high growth startup? What are the big questions founders should ask when an M&A opportunity does arise? What does Elad believe are the reasons to avoid IPOing? What are the inherent benefits of going public? Items Mentioned In Today's Show: Elad's Fave Book: Ben Horowitz, Andy Grove As always you can follow Harry, The Twenty Minute VC and Elad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah's "Favourite Things". Before that Rachel began her career in the publicity department at Yves Saint Lauren. In Today's Episode You Will Learn: 1.) How Rachel went from founding a company that created one of Oprah's "favourite things" to reinventing the way parents shop for their children today? 2.) Why does Rachel believe that "fundraising is like dating"? What does Rachel mean when she says "you have to play the game"? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process? 3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don't need it? What length of time does Rachel believe is the right time to raise for? 4.) Rachel has said before that, "the best investors are operators". What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders? 5.) Rachel previous sly said to me that "being a woman in this male-dominated environment is everything the stereotype suggests", what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations? Items Mentioned In Today's Show: Rachel's Fave Book: Fast Company, Inc As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley's newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today's most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion. In Today's Episode You Will Learn: 1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC? 2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change? 3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete anlyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow? 4.) What has been Pete's greatest time of failure in his career? What is the framework Pete uses to analyse and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder? 5.) How does Pete think about optimising decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early stage investing must be decided with your heart? Items Mentioned In Today's Show: Pete's Fave Book: Leonardo Da Vinci Pete's Most Recent Investment: Ribbon As always you can follow Harry, The Twenty Minute VC and Pete on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Joe Fernandez is the Founder & CEO @ JoyMode, the startup that allows you to lend everything you need to have the experiences you want. To date, Joe has raised over $16m in funding for Joymode from friends of the show including Homebrew, Slow Ventures, Founder Collective, Scott Belsky, Collaborative Fund and Lowercase, just to name a few. As for Joe, prior to founding JoyMode, Joe founded Klout, one of the leading social media analytics platforms of the day and raised $40m in funding from Kleiner Perkins, IVP, Venrock, Greycroft and more. Klout was ultimately acquired by Lithium Technologies where Joe sits on the board. In Today's Episode You Will Learn: 1.) How Joe made his way into the world of startups with the founding of Klout? Given his entrepreneurial start, would Joe say he is unemployable? 2.) Question from Craig Shapiro: What was your single greatest lesson from the Klout journey? How has that impacted how you operate JoyMode today? How has Joe approached fundraising fundamentally differently today than with Klout? How is Joe's team building strategy today different to his with Klout? 3.) Why does Joe believe that "serial entrepreneurs are over-rated"? What does Joe mean when he says, "you have to know which hill you are willing to die on"? How does Joe look to accurately ego check today? What innovative methods does Joe employ internally to ensure that his views are validated and not submitted to? 4.) What does Joe mean when he says, "you have to make big bets to win"? How can you implement this risk-taking mentality in larger teams? What is the right way for both the team and investor base to respond? How does Joe use continuous iteration and data-centricity to test and validate these theses? 5.) How does Joe approach investor update emails? Why does Joe look to terrify investors with each update? Does Joe believe that it is right to thanks specific individuals in those emails? Does like like to select individuals and request their help in the emails? How can past updates be used to attain future investors? Items Mentioned In Today's Show: Joe's Fave Book: The Accidental Superpower As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Joel Monegro is Founding Partner @ Placeholder.VC, one of the new venture capital partnerships that invest solely in crypto assets and more specifically in decentralized information networks. Prior to founding Placeholder, Joel spent three years at Union Square Ventures developing the firm's blockchain investment thesis and portfolio. Before USV, Joel started the Digital Economy Department at the Ministry of Industry and Commerce of the Dominican Republic, a government office in charge of developing the country's national and technology agenda. In Today's Episode You Will Learn: 1.) How Joel made his way into the world of VC with USV and what created his love of crypto and led to his leaving USV to found Placeholder? What were some of Joel's biggest investing lessons from his time with USV? 2.) How does Joel approach portfolio construction in building out a crypto portfolio? How does the use of reserves and building positions change when comparing VC to crypto? Why does Joel believe that the most interesting place to invest in crypto is in the assets themselves, rather than the companies? 3.) When does Joel think we will see institutional capital begin to move into the space in a meaningful way? What needs to happen/change for this institutional interest to materialize? How is the element of "custody" crucial to the entrance of institutions? 4.) In terms of fund construction, liquidity is often an attractive element to crypto, why does Joel believe that a traditional venture fund structure is necessary for Placeholder? What are the benefits both to the fund and the projects it backs? How do LPs both traditional and non-traditional respond to this? 5.) Joel has said before the 2 core elements are crypto economics and governance, why does Josh believe this? Why is governance the foundational layer where value will accrue in the space? How does the lack of defensibility of crypto projects make governance ever more valuable? Items Mentioned In Today's Show: Joel's Fave Book: Antifragile by Nassim Taleb Joel's Most Recent Investment: Decred Investment Thesis As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Max Motschwiller is a Partner with Meritech Capital, one of the West Coast's leading growth investment firms with over $150Bn in IPOs and a portfolio that includes the likes of Facebook, Salesforce, Snap, Box, Mulesoft and Cloudera just to name a few. As for Max, prior to Meritech he spent 3 years with Kleiner Perkins (KPCB) where he was actively involved with investments in Dropcam (Nest/Google), Duolingo, MyFitnessPal (Under Armour), RelateIQ (Salesforce.com) and Stance. Before joining KPCB, Max worked for 3 years at Summit Partners and was actively involved across Summit's technology portfolio. In Today's Episode You Will Learn: 1.) How did Max make his way into the world of VC with Summit and KP from University? What did that decision-making process look like for Max? 2.) As a career VC, would Max agree with Pat Grady @ Sequoia, "the rate of decay on operating experience has never been greater"? What would Max say are the biggest elements he missed through lack of operational experience? How do the skills required from early to pre-IPO change the type of background required? 3.) Max has said before, "to be a good VC you have to do 4 things well", what are those 4 things? Why does Max believe that picking is the greatest skill to develop? At growth, what does Max mean when he says "the picking is around price"? How do the very best VCs approach price sensitivity? 4.) Question from Rob Ward: Max has mastered network development from an early age, what advice would Max give with regards to developing a network? What did he do well and works? What did he try and did not do well? How does Max think about depth vs breadth of network? How does he apply this to investing and due diligence? 5.) In a time of Softbank and Sequoia's $7Bn fund, how does a firm like Meritech look to compete in such frothy environments? How has growth bifurcated into 2 clear stages? What are the advantages of being a small pure-play growth firm? How does the portfolio construction and return expectation change for you given the fund size and stage of investment? Items Mentioned In Today's Show: Max's Fave Book: Home Deus Max's Most Recent Investment: Amplitude As always you can follow Harry, The Twenty Minute VC and Max on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Hemant Taneja is Managing Director @ General Catalyst, one of the world's leading venture firms of the last decade with Airbnb, Stripe, Snapchat, Hubspot and Gusto all in their portfolio. As for Hemant, he has led investments at GC in Stripe, SNAP, Grammarly, Gusto, Livongo, Color Genomics, Class Dojo and more. He also directs the GC Stripe Platform Fund, a $10 million initiative to help start new ventures that are built on top of the Stripe Connect platform. On the educational front, Hemant holds 5 degrees from MIT and sits on the board of Khan Academy. In Today's Episode You Will Learn: 1.) How Hemant made his way from 5 degrees at MIT and wanting to be an academic to pursuing startups in the world of VC with General Catalyst? 2.) Question from Sam @ ClassDojo: What were the hardest elements of establishing GC on the West Coast? With hindsight today, what would Hemant do differently given the chance? How does Hemant think about the development and ability to accelerate the creation of local reputation? What is crucial and works most effectively? 3.) How does Hemant respond to Elad Gil's "everyone is looking for the next truly deep dein to explore"? Why is Hemant so bullish that we are in the "golden age of venture capital"? Why does Hemant believe that "scale" as a key measure has run it's course? What does Hemant's thesis of the future of "unscaling" really mean? 4.) How does Hemant analyse price sensitivity in todays forthy environment? How has his relationship to price changed over time? With regards to price, what have been some of his biggest regrets and learnings drawn from real-world examples? How does Hemant assess reserve allocation? Why does he think pro-rata is a lazy posture? 5.) Hemant has said on boards for over 1,800 hours, so what does Hemant belive makes the truly special board members? How does Hemant think about first building that rapport and "intimacy" with the founder? Secondly, how important does Hemant believe it is to build similar relations with other board members? Which founder exemplifies the best board management in Hemant's mind? Items Mentioned In Today's Show: Hemant's Fave Book: Home Deus Hemant's Most Recent Investment: Spring Discovery As always you can follow Harry, The Twenty Minute VC and Hemant on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. So put your people and culture first and find out more on cultureamp.com.

Amanda Bradford is the Founder & CEO @ The League, the exclusive dating app that wants you to spend your time a little more intelligently when it comes to finding the perfect match online. They have raised funding from the likes of Aileen Lee @ Cowboy Ventures, Sherpa Ventures and Alex Rosen @ Ridge Ventures just to name a few. Prior to founding The League, Amanda spent time at Evernote as a Product Manager, as an investor with Sequoia Capital and started her career in the strategic partnerships team at Google. In Today's Episode You Will Learn: 1.) How Amanda made her way into the world of startups and how she came to want to change the world of dating with The League? 2.) Why does Amanda totally disagree with the conventional wisdom that you cannot be a single founder? What are the benefits of being a single founder? How has Amanda used this to incentivize her team further? What are the core challenges that remain in being a single founder? What 2 reasons does Amanda feel 90% of startups fail? 3.) What does Amanda really mean when she says about "the art of the launch"? How can founders pre-game their launch to have existing users on day 1? What benchmarks does Amanda set when launching a new product, to determine the success of the launch? How core is the 7-day retention number to Amanda in her metric stack? 4.) How does Amanda think about the right time to turn on monetization? How can founders determine the level of consumer appetite for premium products, pre-developing them? What are the main challenges when turning on monetization? How does monetization affect investor appetite? 5.) Amanda has raised from Cowboy, Sherpa, Ridge, how was the fundraising process for Amanda? Why did Amanda choose to pursue the party round approach at seed? What are the core benefits of doing so? Has the lack of lead investor meant a reduced willingness to help from the investor base? Items Mentioned In Today's Show: Amanda's Fave Book: The Giver As always you can follow Harry, The Twenty Minute VC and Amanda on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Peter Parker is the Managing Partner @ BioInnovation Capital, the $130m fund transforming life science investing through backing companies based in shared laboratories in Cambridge, San Francisco, San Diego, Durham, and NYC. For the past three decades, Peter has devoted his life to venture and startups, starting in 1986 with his establishing Ampersand Ventures life sciences platform which he managed until 2006. During this period he was the first institutional capital and a Director to over 2 dozen life sciences startups and enjoyed more exits than I have done podcasts. He is also a co-founder of LabCentral, Inc, a not-for-profit shared facility for companies who need biolab space enables more than 75 companies to pursue their biotech start-up ambitions. In Today's Episode You Will Learn: 1.) How Peter made his way into what was a very different VC industry back in 1986? 2.) Peter has seen the venture ecosystem develop enormously over the last 30 years, what have been the biggest changes and transformations? What are both the most positive and negative changes to hit venture? How has specialization changed the investing game? What would Peter like to change about the world of VC today? 3.) What does Peter mean when he says the best VCs understand the importance of process? What is the right way to construct your process in VC? How does this affect Peter's thinking on functioning partnerships in venture? What can one do to optimise the quality of those relationships and conversations with partners? 4.) Peter has chaired over 25 boards over the last 32 years in VC, how has Peter seen his style of board membership fundamentally change over that time? What have been the inflection points in his learning? How do OKRs play a crucial role in how he drives board operations? How has Peter approached removing the CEO? What is the right way to do it? 5.) Peter's most recent fund is a $130m seed fund, how was the latest fundraise for Peter? What drives Peter's passion and enthusiasm for fundraising and LP communications? What makes the best LP meetings for Peter? How has Peter seen his presentation style to LPs change over time? What has Peter learned is crucial for LP conversion? Items Mentioned In Today's Show: Peter's Fave Book: The Barbarian: A Surfing Life Peter's Most Recent Investment: Graphwear As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. So put your people and culture first and find out more on cultureamp.com.

Paul English is the Co-Founder of both Lola and Kayak. Starting on Lola, the company brings joy to business travelers by finding the best flights for busy schedules and perfect hotels that suit personal preferences. To date, Paul has raised over $44m with Lola from the likes of CRV, Accel, General Catalyst and GV just to name a few. Prior to Lola, Paul co-founded Kayak, the incredible success story that helps millions of travelers make confident travel decisions. Prior to their IPO, Paul raised over $229m in VC funding from Sequoia, Accel, IVP and General Catalyst before their reported $1.8Bn acquisition by Priceline. Paul is also a prolific philanthropist and due to his success has had much press attention including the Tracy Kidder book, A Truck Full of Money. In Today's Episode You Will Learn: 1.) How Paul made his way into the world of startups from having his first taste of entrepreneurship buying and refurbishing air conditioning units? 2.) Paul is behind many groundbreaking ideas of the last decade, so what does the idea generation process look like for Paul? How does Paul determine between a good and a great idea? How has this process changed over time? How does Paul pull other individuals into validating ideas or not? 3.) Paul's VCs stated "Paul is the best founder in the world for hiring", how does Paul approach team building? What does Paul think is required to attract truly world calls talent? Can this skill be taught? Where does Paul believe so many founders go wrong in recruitment? What does Paul mean when he says you want to see "arrogant humility" 4.) Having raised from Sequoia, GV, General Catalyst and more, what has Paul found to really encapsulate the truly special VCs? What are Paul's lessons on raising the highest quality capital possible? When is the right time to optimize for valuation and when is it not? What made Mike Moritz and Joel Cutler so special to work with on Kayak? 5.) How does Paul approach the aspect of board management? How has this changed over time for him? What relationship should founders desire with their VCs and then between the VCs themselves? How does one look to optimise for efficiency in board conversations? How does Paul look to handle board disputes? Items Mentioned In Today's Show: Paul's Fave Book: The Trumpet of Conscience As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Trae Vassallo is the Co-Founder and Managing Director @ Defy.VC, one of Silicon Valley's newest and most exciting Series A funds with the announcement of their debut $151m fund in Sept 2017. Prior to co-founding Defy, Trae was a general partner at Kleiner Perkins Caufield & Byers where she invested in a number of leading companies including eero, Nest Labs, Dropcam, Aggregate Knowledge, and Opower. Before Kleiner, Trae founded Kleiner portfolio company, Good Technology which was ultimately acquired by Blackberry in 2015 for $425m. Trae is also the co-author of the incredible study, "Elephant in the Valley", highlighting the underlying data around the experiences of women in technology. In Today's Episode You Will Learn: 1.) How Trae made her way into the world of VC and Silicon Valley with a cold reach out to John Doerr and how that led to a role with Kleiner Perkins? 2.) What were Trae's biggest learnings from having John Doerr on her board, as a first-time founder? What were some of the most memorable moments working with him? What was it about him that made him such a special board member? What was the moment that Trae realized what type of board member she is? 3.) What does Trae mean when she says "Kleiner taught me what a great investment looks like"? How does that affect her investing philosophy today? How did Trae's investing learnings differ between John Doerr, Vinod Khosla, and Kevin Compton? 4.) Why does Trae believe that the venture industry is simply "overfunded"? If so, what was her reasoning for the founding of Defy? How does Trae see the expansion of multi-stage funds as presenting a market opportunity? Why are the larger players no longer incentivized to play at the Series A stage? 5.) How did Trae find the fundraising process? What were some of the core challenges in terms of the raise itself? Were there commonalities in the pushbacks that LPs had for Defy? How did Neil and Trae respond to the first time team question? How does Trae think about the infrastructure element of funds? Can it all be outsourced? Items Mentioned In Today's Show: Trae's Fave Book: Brotopia: Breaking Up the Boys' Club of Silicon Valley Trae's Most Recent Investment: Owl Car Cam: The First Security Camera For Your Car As always you can follow Harry, The Twenty Minute VC and Trae on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Jack Groetzinger is the Founder & CEO @ SeatGeek, the world's largest ticket inventory on the web serving more than 500,000 artists and teams in over 380,000 venues. To date, Jack has raised over $160m in VC funding with SeatGeek from the likes of John Locke @ Accel, Founder Collective, TCV and most recently a $57m Series D led by Glynn Capital Management. Prior to SeatGeek, Jack founded Scribnia, a web app that used collaborative filtering to recommend bloggers and blog content, sold to an ad network in 2009. Jack is also a Founder Partner @ Founder Collective and angel investor in Troops, Inc. In Today's Episode You Will Learn: 1.) How Jack made his way into the world of startups and decided to reinvent the ticketing industry with SeatGeek? 2.) How does Jack think about the combination of technical vs commercial skills for founders today? Where has Jack struggled with this balance? What would his advice be to prospective founders? How does Jack use OKRs to drive efficiency at SeatGeek? How can OKRs be constructed the right way? What is a rate of failure that suggests you are being ambitious enough? 3.) Jack has raised multiple rounds and over $160m in funding, how have the rounds differed from round to round? How does what Jack wants from an investor differ with time? What one ability do truly unique board members have the ability to do? How does Jack think about board conflicts and the right way to communicate with boards? 4.) How does Jack determine when is the right time to raise big? What is the one core metric that says now is the right time? How does Jack think about both the diversification and mortality of customer acquisition channels? How have SeatGeek seen theirs fundamentally change over time? 5.) Jack led the $56m Toptix acquisition, how was the acquisition process for Jack? What were the big learnings for Jack in terms of buying something that is large? With the acquisition, how does Jack think about the balance between capital efficiency and aggressive growth? What would Jack have done differently with regards to their growth trajectory if he had his time again? Items Mentioned In Today's Show: Jack's Fave Book: Powerful: Building a Culture of Freedom and Responsibility As always you can follow Harry, The Twenty Minute VC and Jack on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Glenn Solomon is a Managing Partner @ GGV Capital, one of the world's leading venture funds with $3.8Bn under management across 8 funds and a portfolio including the likes of Airbnb, Xiaomi, Alibaba, Slack, Square, the list goes on. As for Glenn, since joining GGV in 2005 Glenn has helped 7 companies go public including Pandora, Zendesk, Square, SuccessFactors and more and has led investments in Airbnb, Slack, Opendoor, DOMO and Hashicorp just to name a few. Prior to GGV, Glenn was a General Partner with Partech and before that spent time with Goldman Sachs. You must also check out Glenn's blog here. In Today's Episode You Will Learn: 1.) How Glenn made his way from tennis at Stanford to the walls of Goldman Sachs before entering the world of VC with Partech and then GGV? 2.) Having been in VC for over 20 years, how has Glenn fundamentally seen the startup and VC landscape alter? How did advice from John Doerr alter his thinking on platform shifts? Does Glenn agree with Elad Gil that we are all looking for the next vein of innovation to explore? How must VCs respond? 3.) How has Glenn seen the development of himself as an investor over the last 20 years? What has he found to be the commonalities amongst the very best VCs? How does Glenn think about the importance of investor specialisation? 4.) How does Glenn think about price sensitivity? When has Glenn made his biggest mistakes with regards to price? How does Glenn's opinions change with the differing insertion points from Series A to pre-IPO? 5.) What does Glenn believe makes the truly special board members? What does he mean when he says being on a board is a "full contact" sport? What are the foundational pillars that Glenn has learnt make the most productive and successful board meetings? What can both founders and VCs do to drive efficiency from their time in board meetings? Items Mentioned In Today's Show: Glenn's Fave Book: Shoe Dog, Born A Crime, Irena's Children Glenn's Most Recent Investment: Unravel Data As always you can follow Harry, The Twenty Minute VC and Glenn on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Adrian Aoun is the Founder & CEO @ Forward, a health care system combining world-class doctors with advanced technology to empower patients to take control of their health. To date Adrian has raised funding from some of the true greats of the business including Marc Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levie and Josh Kushner, to name a few. As a result of the incredible work at Forward, they were named to TIME's Best Inventions of 2017. Before Forward, Adrian was the head of special projects for the CEO of Google/Alphabet and Adrian arrived at Google following the acquisition of his artificial intelligence (AI) company, Wavii. Adrian is also a prolific angel with the likes of WorkRamp, Atrium, Convoy and more in his incredible portfolio. In Today's Episode You Will Learn: 1.) How Adrian made his way from selling Wavii to running special projects for the CEO @ Google, to now changing the world of healthcare with Forward? 2.) Why does Adrian believe that ideas don't have to be inspiration based and you can follow a process to come to a startup idea? What is the framework for that process? What is it fundamental that one focuses on the problem not the solution? Post problem identification, what is the next step? 3.) Why does Adrian believe that today, the Lean Startup Methodology makes less and less sense? What leads Adrian to suggest that "regulation is not nearly as scary as people think? How does Adrian break regulation up into 3 different categories? How should investors assess and evaluate opportunities that do face regulation? 4.) What does Adrian believe are the core benefits he has received from investing in over 150 startups? What has Jason recognised with regards to the power law effect when investing? How does Adrian approach pro-rata? What has being on the other side of the table taught Adrian about good and bad actors in the world of VC? 5.) How can angels act as a check/balance on the behaviour of VCs? How does Adrian think about investor behavior in both the good and the bad times? How do the best in the business react in both situations? Items Mentioned In Today's Show: Adrian's Fave Book: Sapiens As always you can follow Harry, The Twenty Minute VC and Adrian on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Dan Scheinman is one of the West Coast's leading angel investors with a portfolio including the likes of Zoom.us, Tango.me, TomFoolery (acquired by Yahoo) and Arista Networks, where he also sits on the board. Prior to angel investing, Dan spent 18 years at Cisco in numerous roles including Senior Vice President of Corporate Development where he rebuilt corp dev as a growth enabler for Cisco. Dan was also the Senior Vice President and General Manager of the Cisco Media Solutions Group (CMSG), an internal startup which successfully developed and marketed a hosted software. In Today's Episode You Will Learn: 1.) How Dan made his way into the world of angel investing following leading the M&A and Corp Dev teams at Cisco? 2.) Why does Dan believe that the days of spray and pray angel investing at seed are over? What does the re-entrance of large funds like Sequoia back into seed investing mean for angels and early-stage VCs? How must the early stage alter their approach with the re-entering of these giants? 3.) Why does Dan believe that the No 1 destroyer of value in a VC portfolio is founder drama? How does this lead his thinking when assessing opportunities? How can this be mitigated? Why does Dan believe it is much harder for people over 35 to raise VC funding? 4.) Why does Dan believe that in the best deals price does not matter? What opportunities has Dan passed on a deal due to price, what have been his subsequent learnings? How does Dan approach the aspect of reserve allocation? What is the decision-making process around reserves? What are the reasons he would not take his pro-rata? How does he communicate this to founding teams? 5.) Why are incumbents no longer so willing to acquire for technology and talent? What problems do these early-stage acquisitions cause for their internal dynamics and culture? When done, why are these early-stage acquisitions less and less friendly for the early investors of the company being acquired? Items Mentioned In Today's Show: Dan's Fave Book: Moneyball Dan's Most Recent Investment: Cycognito As always you can follow Harry, The Twenty Minute VC and Dan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Seth Sternberg is the Founder & CEO @ Honor, the startup that provides homecare your family will love. To date Seth has raised over $60m in funding with Honor from the likes of Thrive Capital, a16z, Homebrew and 8VC. Prior to Honor, Seth was the Co-founder & CEO of Meebo, a web communications platform backed by the likes of Sequoia, Khosla and True Ventures. Meebo reached $50M in revenue and close to half of the US internet population before being acquired by Google for $100M in 2012. At Google, Seth became a Product Director working on the Google+ Platform and GoogleX. Seth is also a prolific angel investor with a portfolio including the likes of Fitbit and Gusto to name a few. In Today's Episode You Will Learn: 1.) How Seth made his way into the world of startups with the founding of Sequoia backed, Meebo? How did he transition from social network to homecare provision? 2.) From his experience with Meebo, what are the biggest elements Seth has done differently with the building of Honor? What was successful the first time that he has carried with him to Honor? How does Seth approach the hiring process fundamentally differently the 2nd time around? 3.) Seth has worked with the likes of Sequoia, Khosla, Thrive and more, what are the commonalities that make the best VCs so special? Where does Seth believe VCs can add true value? Where do many seriously detract value? Why does Seth believe that 80% of VCs are actually detrimental to board meetings? 4.) What 3 questions must all founders ask when considering to take on a new investor? What is that investor-founder assessment structure? When there is a disagreement with investors, how does Seth approach this? What is the best method for doing this in as fast and efficient method as possible? 5.) Would Seth agree with David Barrett @ Expensify that we are going through a wave of founders creating companies for the quick flip? How does Seth's 20-year time horizon with Honor affect how he both thinks about hiring and individual scaling within the firm? Why is he so jealous of Google and Facebook with regards to this? Items Mentioned In Today's Show: Seth's Fave Book: The Firm As always you can follow Harry, The Twenty Minute VC and Seth on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Boris Wertz is the Founding Partner @ Version One Ventures, one of North America's leading early-stage funds with a portfolio including the likes of previous guests Coinbase, AngelList, Shippo, TopHat, Polychain Capital and many more incredible companies. As for Boris, prior to VC, Boris was the COO @ Abe Books, where he led a team of 60 people until their acquisition in 2008 by Amazon. In addition to this, Boris is also a Board Partner with a16z and the lead independent director @ Ether Capital, a Toronto-based technology company aiming to become the central investment hub for the Ethereum ecosystem. In Today's Episode You Will Learn: 1.) How Boris made his way from creating the largest European marketplace for used books to becoming one of North America's leading investors with Version One? 2.) How does Boris analyze where we are at now in the development and hype cycle of crypto? How does it compare to the internet bubble of 99'? Does Boris get concerned by the amount of dumb money entering the space? What resources and tools does Boris advice for people looking to learn the foundations as quickly as possible? 3.) Why does Boris believe you have to apply a new mental model when investing in crypto? What do existing VCs need to do to ensure they are not left behind by the emerging world of crypto? What does Boris believe would need to happen for the existing institutional LP class to embrace crypto? 4.) Does Boris believe existing investors can transition into this space or will vertically specialised funds be the clear winner? If existing investors can, what is required within their partnerships to make this happen? What does Boris make of VCs investing in ICOs? How does Boris evaluate the Telegram ICO? 5.) How does Boris view the future of VC in tandem with the world of crypto and ICOs? What would VCs becoming small cap hedge funds mean for the industry? How would life change? What have been Boris' biggest learnings from watching first hand a16z's attempts to innovate the VC model at scale? Items Mentioned In Today's Show: Boris' Fave Book: Shoe Dog Boris' Most Recent Investment: Coinbase As always you can follow Harry, The Twenty Minute VC and Boris on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Andrew Dudum is Co-Founder & CEO @ Hims, the fastest growing men's health and wellness brand that has raised over $45m in VC funding from some of the best in the business including Thrive Capital, Forerunner Ventures, IVP, Redpoint and SV angel just to name a few. Andrew is also co-founder and General Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world's best investors. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication. In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF). In Today's Episode You Will Learn: 1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men's health and wellness brand in Hims? 2.) How does Andrew view the world of online and offline marketing in today's proliferated D2C space? What were the core elements that allowed Hims to achieve such success with their branding? How does Andrew respond to suggestions that there is a lack of free and open distribution due to incumbents paying up for traditional channels making CAC unachievable for startups? How does Andrew look to solve for this? 3.) What does Andrew believe it is that has allowed Hims to execute faster than any other D2C brand in history? How does Andrew distinguish between people and process when considering the scaling at different stages of the business? What are the pros and cons of having such constraints on headcount? When is the right time to pour fuel on the fire? 4.) Hims raised their last round at a $200m valuation in less than a year of operating, how did Andrew evaluate this one? Does this not effectively price Hims out of the majority of M&A? What leads Andrew's thesis with his suggestion that he thought the valuation was "quite frankly, a great price for investors"? What advice would Andrew have for founders entering the fundraising process? 5.) Andrew is also the co-founder @ Atomic, so what really is a venture builder? How have Atomic built a framework around idea generation? How do Atomic determine which ideas to pursue and which to disregard? How does data and benchmarking play a central role in this process? Items Mentioned In Today's Show: Andrew's Fave Book: Creativity Inc As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Andy McLoughlin is Partner @ Uncork Capital, formerly SoftTech and one of the leading early-stage funds on the West Coast. In their incredible portfolio, they have the likes of Fitbit, SendGrid, PostMates, Front, PoshMark, Eventbrite and many more. As for Andy, he loves to invest in "unsexy ideas" with stellar teams and has led deals in the likes of Postmates, LaunchDarkly, Human Interest (previously Captain 401), and Focal Systems just to name a few. Prior to VC, Andy co-founded Huddle, an enterprise collaboration platform which raised more than $80M in venture funding before its acquisition in 2017. Andy also has a stellar angel portfolio with the likes of Buffer, Intercom and Pipedrive all angel investments. In Today's Episode You Will Learn: 1.) How Andy made the transition from Founder of one of the UK's hottest startups to one of the leading early-stage VCs in Silicon Valley? 2.) Why did Softtech decide to make the big decision to rebrand to Uncork several years into the journey? What is core to successfully relaunching a VC brand to the ecosystem? 3.) Andy likes to back "non-obvious founders" building "non-sexy businesses". What does Andy mean by "non-obvious founder"? How do they tend to behave differently to more seasoned serial entrepreneur founders from the valley? What does a "non-sexy business look like to Andy"? Why does he see such inherent opportunity within these segments? 4.) How does Andy evaluate the challenge of immensely long sales cycles within these industries? How can these be mitigated and measured against? How does this affect Andy's thinking on the right amount of runway to raise for? How does Andy assess the often issue of regulation? How does Andy distinguish between viable/ non-viable? 5.) How does Andy assess VC value add? Where does Andy believe he can provide the most value to his portfolio? Why does Andy believe startups are not just competing against other plays in their space but every startup in the valley? Items Mentioned In Today's Show: Andy's Fave Book: Venture Deals Andy's Most Recent Investment: Fritz As always you can follow Harry, The Twenty Minute VC and Andy on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours – tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Jesse Genet is the Founder & CEO @ Lumi, the startup that is used by thousands of e-commerce companies to get world-class packaging at unbeatable prices. To date, Jesse has raised close to $10m in VC funding from some of the best in the business and old friends of the show including Satya @Homebrew, Kirsten @ Forerunner, Spark Capital, Lowercase, Ludlow and more incredible names. Prior to Lumi, Jesse founded Inkodye, a bootstrapped business that Jesse scaled to 7 figures in revenue and was sold in retail stores around the world. In Today's Episode You Will Learn: 1.) How Jesse made her way into the world of startups and VC having bootstrapped her prior business to 7 figures in revenue and being sold in 1,500 stores? 2.) Given that Lumi is Jesse's first VC backed business, does this make Jesse a first-time founder? How did the bootstrapping to 7 figures in revenue with her last business, influence her philosophy and mindset with Lumi? What has Jesse done differently as a result? What are the dangers that Jesse was aware of and looks out for? 3.) What types of companies does an active content strategy make significant sense for? What are the core benefits of a well-executed content strategy? What have been the core pillars to Jesse's success with content? Where does Jesse see many firms going wrong with their content strategy? How does Jesse look to measure the ROI from content? 4.) How was the fundraising experience for Jesse, given the "non-sexy" sector of packaging and supply chains? How did Jesse determine whether an investor was engaged or not? What does Jesse think she did well in the fundraising process? What would she like to improve for the next round? What is the common stereotype that VCs attribute to founders with bootstrapping experience? 5.) How does Jesse think about the benefits of her team being small vs her 10,000+ incumbent challenger teams? Why does this mean she has the advantage? How does Jesse manage the expectations of her employees when no one could do 1/10 of what Jesse does? Items Mentioned In Today's Show: Jesse's Fave Book: Gone with the Wind As always you can follow Harry, The Twenty Minute VC and Jesse on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam - as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours - tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

Jerry Neumann is one of New York's leading angel investors with a portfolio including the likes of The Trade Desk (IPO: 2016), Datadog and Flurry (acquired by Yahoo) just to name a few. Prior to angel investing, Jerry built the first open market for the pricing and exchange of real-time consumer data in the form of Root Markets. Jerry was also the Managing Director @ Omnicom's Venture Capital Division where he enjoyed an incredible 5 IPOs from the portfolio. In Today's Episode You Will Learn: 1.) How Jerry made his way into the world of VC in the 90s and why it was difficult to lose money in venture at that time? 2.) Why does Jerry believe that the vast portfolio construction model is "wrong" and a "dead end"? In what circumstances does Jerry believe "spray and pray" investing can work? Why does Jerry believe you can only have as many companies as you can actively help? How does this lead Jerry's thinking on his own portfolio construction? 3.) Why does Jerry believe that startups must have a board from Day 1? What are the inherent benefits of having a board so early? In the earliest of stages, how should those board meetings be run? Who are the best board members Jerry has worked with? Why were they so exceptional? How does Jerry think about building board intimacy? 4.) Why does Jerry disagree with the conventional wisdom of Silicon Valley that price does not matter because the exit will either be huge or a zero? How has Jerry seen the best firms in their thinking on market price vs indicated discount price? How has Jerry's thinking on price sensitivity changed over the years? 5.) Why does Jerry believe that the follow-on investment is always a much better investment? How does the risk-reward ratio change from initial to follow-on investment? How does Jerry assess and prioritize future financing risk when investing in an opportunity? How does he mitigate that as much as possible? Items Mentioned In Today's Show: Jerry's Fave Book: Console Wars by Blake Harris Jerry's Most Recent Investment: Edmit As always you can follow Harry, The Twenty Minute VC and Jerry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. We also speak about Movidiam - as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They're already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam's account managers in hours - tailored to their project's needs. Submit a brief or check out the platform at Movidiam.com.

James Reinhart is the Founder & CEO @ ThredUp, the world's largest online thrift store, and consignment store. To date, ThredUp has raised over $130m in VC funding from many friends of the show including Tim @ Redpoint, Patricia @ Trinity, Eric @ Founder Collective and Ian @ Goldman Sachs just to name a few. As for James, prior to ThredUp he was a Goldsmith Fellow in Social Enterprise at HBS and a Bill George Fellow at the Center for Public Leadership at the Kennedy School. Before that, James co-founded Beacon Education Network, a charter management organization serving low-income students on California's Central Coast. In Today's Episode You Will Learn: 1.) How James' childhood dream of being an architect changed to founding the world's largest online thrift store? 2.) Tim Hale @ Redpoint: "James is one of the most naturally talented leaders I have ever worked with". So what does great leadership mean to James? How has James seen the way he communicates and inspires change with the scaling of the company? What has James observed as the core characteristics that great leaders share? 3.) Why does James believe that investors are inherently wary of the female and child clothing market? How did James see the funding rounds differ from round to round? What did James really look for in his early investors? How does investor value-add change with time and scaling? 4.) What have been James' core learnings in managing a board with transparency and efficiency? James has said before "your board is right 50% of the time". How does James look to determine which 50% is right vs wrong? What is a time when James has gone against the decision of the board? How did the situation result? 5.) Having raised over $130m in funding, how does James think about the balance between aggressive growth and capital efficiency? How does James assess when is the right time to pour fuel on the fire? How does James react to the mindset of "sustainable growth"? How do investors think about capital efficiency? Items Mentioned In Today's Show: James' Fave Book: Sapiens As always you can follow Harry, The Twenty Minute VC and James on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS. In Today's Episode You Will Learn: 1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there? 2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to? 3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive? 4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds? Items Mentioned In Today's Show: Chris' Fave Book: The Old Man and The Sea Chris' Most Recent Investment: Duolingo As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS. In Today's Episode You Will Learn: 1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there? 2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to? 3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive? 4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds? Items Mentioned In Today's Show: Chris' Fave Book: The Old Man and The Sea Chris' Most Recent Investment: Duolingo As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Marco Zappacosta is the Founder & CEO @ Thumbtack, the startup that allows you to find local professionals for pretty much anything. To date, Thumbtack has raised over $270m in funding from some of the very best including Sequoia Capital, CapitalG (Google Growth), Ali and Hadi Partovi, Scott and Cyan Banister and Jason Calacanis. Due to Marco's incredible success scaling Thumbtack to helping millions of Americans today, he has been recognized by Forbes as 30 under 30 and Thumbtack was recently acknowledged as one of GlassDoor's best places to work. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today's Episode You Will Learn: 1.) How Marco made his way into the world of startups and came to create one of the most prominent marketplaces of the day in Thumbtack? 2.) What does Marco mean when he says "founders must treat board members as employees"? How does Marco view the optimal structure for a board meeting? What are the core elements that founders must takeaway? Where do most first time founders go wrong with board management? 3.) Thumbtack has raised over $250m in VC funding, how can one look to achieve both operational efficiency and capital efficiency with such large injections of capital? What is core to maintaining this sense of frugality despite such large investments? How does Marco think about when is the right time to raise that warchest round? 4.) How does Marco suggest that marketplace founders can entice the supply side in the early days? How has Marco seen his supply-side acquisition change and develop with time? What has worked and what has not? Does Marco agree with Leah Busque that in marketplace, the NPS for one side will always be down? Items Mentioned In Today's Show: Marco's Fave Book: The Wizard and The Prophet As always you can follow Harry, The Twenty Minute VC and Marco on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Zal Bilimoria is Founding Partner @ Refactor Capital, one of Silicon Valley's newest entrants to the early stage scene with a $50m fund looking to back founders solving fundamental human problems. Prior to co-founding Refactor, Zal was a Partner @ a16z where he co-led investments in Omada Health, Branch.co, AltSchool, Honor, and more, while helping to launch the firm's Bio Fund. Before becoming an investor, Zal spent 10 years as a PM at Microsoft, Google, Netflix, and LinkedIn. He worked on emerging markets for Windows, became one of the first monetization team members at YouTube, and then became the 1st Head of Mobile at Netflix and helped start the Sales Solutions business at LinkedIn. In Today's Episode You Will Learn: 1.) How Zal made his way into the world of VC with a16z from the very corporate worlds of Microsoft, Google, Netflix and LinkedIn? 2.) What were Zal's 3 biggest learnings from seeing the internal processes and scaling of a16z? How does a16z use NPS in such a compelling way that it automatically improves founder treatment and interaction within the firm? What was it about a16z that led Zal to believe being insanely curious is the biggest skill of an investor? 3.) What are the signs and leading indicators that a scientist has the mental plasticity and ability to translate into a CEO and business leader? What are the biggest challenges as a VC in assessing whether this plasticity is present? Why does David believe that the very best founders are looking to solve "fundamental human problems"? 4.) Over the last few years we have seen an explosion of deep tech capital, Elad Gil suggested this reminded him of the 2007 cleantech days, does Zal agree with this suggestion? How does Zal think about the common concern of having to carry companies for longer given the extended milestones to prove progress? 5.) Zal has said before his goal is "to build a seed firm to last among the 100s of others", what does Zal believe is crucial to this sustainability of fund and brand? How does Zal evaluate the insanely crowded seed market today? Items Mentioned In Today's Show: Zal's Fave Book: Seveneves Zal's Most Recent Investment: Solugen As always you can follow Harry, The Twenty Minute VC and Zal on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley's leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies. In Today's Episode You Will Learn: 1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC? 2.) Question from Oren Zeev: Having been a partner at both, how does Paul compare the culture and strategy of two such differing firms of Canvas vs NEA? How does Paul's thinking on exit expectations and requirements change with the change of fund? How does a smaller fund fundamentally change the way you think about investing? 3.) What does Paul believe are the 5 fundamentals of building and scaling a successful marketplace? Why does Paul believe that it is the supply side that tells you if your marketplace is or is not working? Why does Paul believe stubbornness is good in marketplace founders? 4.) Why does Paul believe that raising $100m is critical for new companies if they want to go big? What does this mean for capital efficiency? What does this mean for ownership with multiple dilutive rounds impacting investor returns? How should founders then think about winning the "capital arms race"? What are the exceptions to these rules? 5.) Female founders receive 2.19% of VC funding, however, Paul has many more female founders in portfolio than the industry. Why does Paul think this is? What would Paul like to see change in the distribution of VC funds? What is the required steps to make this happen? Items Mentioned In Today's Show: Paul's Fave Book: The Innovator's Dilemma Paul's Most Recent Investment: Thrive Global, Roofstock As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the "Sell Your Item" team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few. In Today's Episode You Will Learn: 1.) How Darian made his way into the world of tech as Facebook's first ever intern at the age of 17 and how that led to the founding of Radius? 2.) According to Joe Lonsdale @ 8VC, "Darian is one of the most respected founders and CEOs in the valley". How does Darian define great CEOship? What have been the commonalities he has seen in the great leaders he has engaged with from Mark @ Facebook to Mark Pincus? 3.) How did Darian approach the fundraising strategy for the $85m he has raised with Radius? How does Darian believe that founders can test quickly whether an investor is truly interested? Why is it so important to be fundraise as fast as possible? If an investor could only provide Darian one thing, what would it be and wh? 4.) How does Darian respond to investors that suggest founders should not be actively angel investing, as Darian is? What operational benefits does Darian gain from angel investing? How does Darian think about angel portfolio construction and specialisation? How has Darian seen investor attitudes alter when it comes to capital efficiency? 5.) As an early Bitcoin miner, how does Darian evaluate the world of crypto today? Why does Darian believe BTC has reached escape velocity compared to other currencies? Why was Darian skeptical on Ethereum for so long? What are Ethereum's ongoing challenges? Why does Facebook have the chance to dominate the world of crypto? Items Mentioned In Today's Show: Darian's Fave Book: Sapiens As always you can follow Harry, The Twenty Minute VC and Darian on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Jerry Chen is a Partner @ Greylock Partners, one of the world's most successful VC funds with prior investments in the likes of Facebook, Instagram, LinkedIn, AirBnB, Dropbox, AppDynamics, Coinbase and many more incredible companies. As for Jerry, Jerry invests in entrepreneurs building new enterprise SaaS applications and in all aspects of AI and cloud infrastructure. Jerry currently sits on the Board of Docker, Cato Networks, Gladly, Rhumbix, Spoke, and Blend. Prior to joining Greylock, Jerry was Vice President of Cloud and Application Services at VMware where he was part of the executive team that scaled the company from 250 to over 15,000 employees and $5B in revenue. Check out Jerry's recent writing on Risk: The Game of Strategic Investment here. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today's Episode You Will Learn: 1.) How Jerry made his way into the world of VC with Greylock from being on the exec team at VMWare, responsible for their scaling from 250 to over 15,000 people? 2.) What does Jerry believe are the different frameworks for how investors should measure risk? Why does Jerry believe to be a good investor, one has to be an optimist? What does Jerry find the most challenging element of risk assessment? What types of risk can Jerry tolerate and which can he not in a potential investment? 3.) How does Jerry break the theme of risk down into 2 very different categories? How does one define "uncertainty" in an investment? How does this compare to "probability"? How does both "uncertainty and probability" alter when comparing differing sectors? Does Jerry think that current pricing takes fair account of both "uncertainty and probability"? 4.) What does Jerry mean when he says, "you have to have product go-to-market fit"? Why does Jerry believe that platforms shifts are fundamentally distribution model shifts? Where does Jerry see an inherent opportunity within these net new nodes of distribution shift? 5.) How does Jerry evaluate the SaaS world today of bottoms up or top down? Why does Jerry believe that if you are budget additive, bottoms up with small ACVs is the current strategy? What does this mean for those that are budget replacements, both in sales model and ACV? Items Mentioned In Today's Show: Jerry's Fave Book: Skin In The Game Jerry's Most Recent Investment: Blend As always you can follow Harry, The Twenty Minute VC and Jerry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Rachel Drori is the Founder & CEO @ Daily Harvest, the direct-to-consumer brand that delivers real, unprocessed, unrefined foods in the most convenient format possible: frozen. To date, they have raised over $43m in funding from the likes of former guest Alex Taussig @ Lightspeed, Collaborative Fund and future 20VC guest Beth Ferreira who sits on the board. As for Rachel, prior to starting Daily Harvest, Rachel harnessed her skills as a customer-centric marketing executive, leading teams at Gilt Groupe, American Express, and Four Seasons Hotels and Resorts. In Today's Episode You Will Learn: 1.) How Rachel made her way from the corporate world of American Express and The Four Seasons to founding Daily harvest, looking to change the eating habits of millions? 2.) Why did Rachel decide to deliberately raise small Seed and Series A rounds? What does Rachel believe these capital constraints allow companies in the early days? How did Rachel prioritize where to spend and where not to? How would Rachel advise emerging startup founders when it comes to capital efficiency today? 3.) Rachel recently raised $43m Series B, how did Rachel see the rounds differ from round to round? Why does Rachel believe it is imperative to VC date before the fundraising process begins? Why was Rachel's Series A very unconventional in the modern world of fundraising? What did Rachel look for most in the investors she chose from round to round? How is that different considering her single founder status? 4.) Question from Alex Taussig: How has Rachel seen the NYC ecosystem develop and evolve since the founding of Daily Harvest? Would Rachel agree that there remains a lack of early stage conviction investors in NYC? What are NYC's biggest strengths and then biggest weaknesses? 5.) Rachel has said before, "fake it till you make it" when was the last time Rachel did this and what was the outcome? Rachel also said previously, "ask for forgiveness not permission", when was the most recent occassion of this and what did it result in? Items Mentioned In Today's Show: Rachel's Fave Book: Deep Nutrition: Why Your Genes Need Traditional Food: Volume 1 As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep! Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don't take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.