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

Sarah Cannon is a Partner @ Index Ventures, one of the world's leading venture funds with a portfolio including the likes of Dropbox, Skype, Figma, Bird, Slack and many more incredible companies. As for Sarah, at Index, she works with groundbreaking companies including Notion, Slack, Pitch, Quill and Instabase. Prior to Index Sarah spent time at CapitalG, Warburg Pincus and even worked in The White House as Policy Advisor for the National Economic Council. Akshay Kothari is the COO @ Notion, the company that has taken the modern working world by storm as the all-in-one workspace to write, plan, collaborate and get organised. Just last week Notion raised a $50M round led by Index at a reported $2Bn valuation. Prior to Notion, Akshay spent 5 years at LinkedIn following his prior company, Pulse News, being acquired by LinkedIn in 2013. In Today's Episode You Will Learn: 1.) How did Sarah make her way into the world of venture from The White House and come to be a Partner @ Index today? How did Akshay parlay his angel investment into Notion into joining as COO the company 5 years later? 2.) With such a proliferation of collaboration tools today, how does Sarah see the remote work/collaboration tools landscape playing out? Are wein a phase of bundling or unbundling? Will we enter a phase of heavy consolidation? How does Notion think about the transition from an application to a platform? What are the challenges in doing so? 3.) What have been some of Akshay's core observations and learnings from watching the world move to remote work overnight? What behaviours will remain post COVID? What behaviours will not? What sectors will be forever changed due to the crisis? What opportunities does that bring about? 4.) Why did Notion decide to keep the team so small for so long? What are the advantages? How does Notion think about maintaining quality when hiring for scale now? What have been some of Akshay's biggest learnings in what it takes to attract A* talent to Notion? 5.) Why did Notion choose the route of profitability over the more conventional early path of the VC treadmill? How does one's mindset change when suddenly raising a large round of new financing? What becomes possible? What guard rails still need to be set? Items Mentioned In Today's Show: Akshay's Fave Book: Order without Design: How Markets Shape Cities Sarah's Fave Book: Guns, Germs and Steel: A short history of everybody for the last 13,000 years 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. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

David "DHH" Heinemeier Hansson (@dhh) is the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37Signals), and the best-selling co-author of Rework and Remote: Office Not Required. If that was not enough, fun fact, he went from not having a driver's license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the "Grand Prix of endurance and efficiency." In Today's Episode You Will Learn: 1.) How David made his way into the world of tech and startups from his childhood living in Copenhagen and how a cold email led to the founding of Basecamp with Jason Fried? 2.) What have been some of David's core observations as people move to remote work over the last few weeks? What is the #1 mistake that 90% of teams make? How does David advise founders to approach loneliness and depression in their team? What strategies have Basecamp used to unite the team and inspire collaboration and teamwork? 3.) Why have David and Jason always tried to keep the Basecamp team as small as possible? Why does David believe one of the biggest problems is that execs have too much time? How does that manifest itself? What does David's week look like? How does he approach meetings? 4.) Why does David hate the majority of "mission statements" today? What are the best composed of? What are the worst? What feelings does David believe your mission statement should inspire in the reader? What does David believe one needs to do to build a challenger brand today? 5.) Why has David and Basecamp always resisted the conventional path of raising VC funds? Why does David believe needs VC money is total BS? Why does David believe it is BS to chase being a unicorn? Why have founders got this so wrong today and what can they do to change? 6.) How would David describe his relationship to money? How has that relationship changed over time? What are the core challenges as one moves from a monetary to a deeper appreciation of what makes one happy? How did the transition occur for David? How does David advise others in terms of finding their moment for the transition? Items Mentioned In Today's Show: David's Fave Book: Erich Fromm: To Have Or To Be As always you can follow Harry, The Twenty Minute VC and David and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Blake Scholl is the Founder & CEO @ Boom Supersonic, the world's fastest commercial aeroplane, aspiring to bring back supersonic passenger flight at an affordable price. To date, Blake has raised over $166M in funding with Boom from the likes of Paul Graham, Sam Altman, Ray Tonsing @ Caffeinated Capital, Homebrew and 8VC to name a few who have featured on the show in the past. Prior to changing the world of commercial flight, Blake started his career with a 5-year stint at Amazon as a Manager of Social Networks and Automated Advertising. Blake then went on to found his own company, Kima Labs, acquired by Groupon in 2012 where he then spent 2 further years before founding Boom. In Today's Episode You Will Learn: 1.) How Blake made the move from Groupon to changing the way we think about commercial travel today with Boom Supersonic? 2.) How was the fundraising process for Blake given he was raising for supersonic jets? What is his most memorable fundraising moment? Where does Balek believe investors provide outsized value? Where could the investing class improve? How should the fund structures today change? 3.) What deliberate choices and decisions has Blake made to find and acquire the best talent? What is Blake's favourite interview question? What works? What does not work? What specific elements has Blake built into the culture at Boom to build operational excellence? 4.) How has Blake seen himself evolve and develop as a leader over the last few years? What have been the most challenging elements to develop and scale? How does Blake feel on whether founders should have experience on the industry they are entering or if there are benefits of not having so? 5.) What would Blake really like to change about the world of tech and Silicon Valley today? How does Blake feel about the current level of both innovation and founder ambitions? What can be further done to foster this in the coming years? Items Mentioned In Today's Show: Blake's Fave Book: Atlas Shrugged As always you can follow Harry, The Twenty Minute VC and Blake and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest and largest early-stage seed firms. Prior to co-founding Stride, Fred was a General Partner @ Accel where he was the lead investor and board member at Deliveroo, Pillpack (acq. AMZN for $1BN) and Carwow. Prior to Accel, he was a partner at Atlas Venture (now Accomplice) where he invested in and served on the board of Pillpack, Zoopla (IPO), Secret Escapes, Integral Ad Science (partial exit to Vista at $850M) and TheCurrencyCloud to name a few. Fun fact, his portfolio has a total enterprise value of more than $10BN and he generated in excess of $700M in exit value to investors. In Today's Episode You Will Learn: 1.) How did Fred make his way into the world of venture and come to co-found one of Europe's newest and largest seed funds in Stride.VC? 2.) If you look to Twitter, all VCs are "open for business", does Fred really believe the market is still open for business? How will deal volume be affected? How bad does Fred think this could get? How does this downturn compare to that of the dot-com and 2008? 3.) Why did Stride decide to take the decision to pause on investing at this moment in time? How does Fred respond to the suggestion of better pricing and less competition at this time? How does Fred believe venture investors view of risk evolves at this time? What is the first to change? 4.) With many new funds deploying their first fund in 18 months, does Fred think we will see a gravyard of new fund managers out of cash and with cash hungry portfolios? What advice does Fred give to newer managers of other elements they have to be minfdul/aware of? 5.) How does Fred think about the right way for managers to communicate with their LPs at this time? What has Stride done that has worked? Does Fred believe we will see many LPs defaulting on their initial commitments? How does Fred think emerging managers can navigate this? Items Mentioned In Today's Show: Fred's Fave Movie: Mulholland Drive Fred's Most Recent Investment: Collective Benefits As always you can follow Harry, Fred and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ravi Viswanathan is the Founder and Managing Partner @ NewView Capital, launched in 2018 with their $1.35Bn Fund I, they have already set themselves as leaders in the world of growth funding with 3 massive exits in less than 2 years in the form of Plaid, sold to Visa for $5.3Bn, Acquia, sold to Vista Equity for $1Bn and then Scout, sold to WorkDay for $540M. Prior to founding NewView Ravis spent 14 years at one of the largest venture firms in the business, NEA where he co-led their venture growth equity practice and in 2016, became COO @ Nea. Before the world of venture, Ravi spent 4 years as a VP @ Goldman Sachs and before that was at McKinsey & Co. In Today's Episode You Will Learn: 1.) How Ravi made his way into the world of venture from investment banking and how that led to his founding the monster $1.35Bn Fund I for NewView Capital? 2.) Given the first fund being $1.35Bn, how did Ravi find the fundraising process for NewView? On reflection, what did he and the team do well that they would do again? What did they not do well that they would alter? What advice would Ravi give to first-time fund managers raising today? 3.) Would Ravi agree with Bill Gurley, "the biggest challenge today is the sheer quantum of capital flowing into the industry"? What does Ravi make of the rise of private equity (PE) houses entering the venture landscape? How does it change the exit landscape? 4.) How does Ravi think about the right way for funds to navigate and approach the secondary market? What advice would he give to emerging managers? How does Ravi feel about founder secondaries? What framework does he use to determine whether the amount is reasonable? 5.) How does Ravi think about what it take to truly win the best deals in competition today? If one does not have the budget of a16z, how does one build a venture platform? Where do the majority of investors make mistakes when it comes to VC value add? Items Mentioned In Today's Show: Ravi's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Born A Crime: Stories from a South African Childhood Ravi's Most Recent Investment: Plaid As always you can follow Harry, Ravi and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Businesses are always looking for ways to shorten their sales cycles. HelloSign provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They're an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don't let pen and paper processes slow you down. Click Here to join the millions of users already using HelloSign to close more deals faster!

Jean-Charles Samulian is the Co-Founder & CEO @ Alan, the startup revolutionising health insurance with a service centred on people, simplicity and comfort. To date, Jean-Charles has raised over $85M in funding with Alan from some of the best in the business including Jan Hammer @ Index, Shakil Khan, Tom Stafford @ DST, Xavier Niel and Brent Hoberman to name a few. Prior to changing the healthcare insurance system, Jean-Charles founded Expliseat, revolutionising airline seating for economy class, now used by some of the world's leading airlines. In Today's Episode You Will Learn: 1.) How Jean-Charles made his way from re-inventing the airline seating industry to re-inventing the way consumers experience healthcare insurance? How did re-inventing the airline seat prepare and impact Jean-Charles' mindset going into the highly regulated healthcare market with Alan? 2.) How does JC structure his investor updates? What framework does JC believe these investor updates should take? Does he include thank you's at the end? Does he include requests for help? How does he involve the team in the writing of these updates? How does JC insert core strategic thinking into his updates? How much time does JC allocate to writing updates? How does JC think about transparency when coming investor updates? 3.) How has JC created a culture of distributed ownership combined with radical transparency? What are the key elements to achieve this? Where do so many go wrong with culture maintenance and creation? What have been the biggest challenges in scaling from 20 to 190 people in just 2 years? What has worked? What has not worked? 4.) How does JC structure the hiring process at Alan? Why does JC believe in the importance of "shadowing" for people to be excellent at hiring? How does JC define "excellence" in a potential candidate? What questions does JC most like to ask candidates? How does JC think about the right way to optimise new employee onboarding? Where do many go wrong with onboarding? What have been their core lessons at Alan as to what it takes to make it great? 5.) How does JC think about extreme self-organization today? How does JC structure his day and his time? How would JC summarise his relationship to his phone? What does he actively do to reduce his dependence on his phone? What has worked and what has not worked with regards to increasing productivity? How does JC advise others looking to make their first steps in increasing their productivity? Items Mentioned In Today's Show: Jean-Charles's Fave Book: The Everything Store: Jeff Bezos and the Age of Amazon As always you can follow Harry, The Twenty Minute VC and Jean-Charles and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Howard Marks is the Co-Founder and Co-Chairman of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, "When I see memos from Howard Marks in my mail, they're the first thing I open and read. I always learn something." In Today's Episode You Will Learn: 1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard's life? 2.) What does Howard believe is the fundamental economic crisis occurring today? How does Howard expect liquidity availability to change over the next few years? What analogies of prior downturns and recessions can we look to learn from? How does this downturn differ and align to prior recessions and downturns? What policies would Howard like to see governments enact to prevent the worst-case scenario? 3.) In conditions of such uncertainty, how does Howard think about how to manage and move forward with such volatility? What are Howard's frameworks and mechanisms to analyse crises events like this? Taking the analysis one level further, how bad does Howard believe this could get? If short of The Great Depression, are there scenarios that could lead there? What are the leading signals? 4.) Being proactive, how does today's situation change the mentality and activity at Oaktree? Why does Howard not agree with the notion of "the falling knife"? How does Howard think about market bottoms? How does Howard determine the right insertion point? Why does Howard believe the best investors are unemotional? How can one manage the psychology of catching a falling knife that falls further? 5.) What advice would Howard give to the may millions of working professionals today that have never seen a recession in their professional career? What makes Howard the most nervous when he looks at and assess the landscape today? What does Howard believe is the biggest misconception people believe with regards to the current economic crisis? Items Mentioned In Today's Show: Howard's Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets 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.

Alyssa Ravasio is the Founder & CEO @ Hipcamp, the startup that allows you to book unique camping experiences on over 300,000 campsites, cabins, RV parks, public parks and more. To date, Alyssa has raised over $41M in funding from some of the best in the business including Benchmark, a16z, Brad Feld, Dave Morin, Sam Shank @ Hotel Tonight and more. Prior to founding Hipcamp, Alyssa enjoyed numerous diverse roles including being Director of Sales & Marketing @ Revel Systems to working on International Information and Communication Policy in the US State Department. In Today's Episode You Will Learn: 1.) How Alyssa made her way from the US State Department to founding the game-changer of camping experiences in the form of Hipcamp? 2.) How did Alyssa solve the classic chicken and egg problem for marketplaces in the early days with Hipcamp? How important does Alyssa believe it is for marketplaces to have truly differentiated supply? How does Alyssa think about what it takes to prevent leakage in marketplaces today? How can marketplace founders be strategic in building moats around their business? What works? What does not work when building marketplace defensibility? 3.) How does Alyssa manage the psychology of being CEO? What does Alyssa find to be the most challenging element of the role? What have been Alyssa's biggest lessons from her last 12 months in the role? How has she seen her style of leadership change and develop over time? How does Alyssa deal with the shit hit the fan moments? 4.) How did Alyssa find the fundraising process for Hipcamp? Why did Alyssa wait 5 years before raising the Series A? What changed in the business that made Alyssa realise then was the right time to raise big? How did the Series B with a16z and Andrew Chen catalyse so fast? Why did Alyssa select the investors she did? What investors did Alyssa not select or not select her that she would also loved to have worked with? Items Mentioned In Today's Show: Alyssa's Fave Book: The Overstory: Shortlisted for the Man Booker Prize 2018, Uncanny Valley: A Memoir As always you can follow Harry, The Twenty Minute VC and Alyssa on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Manu Kumar is the Founder @ K9 Ventures, one of the leading seed firms of the last decade with a portfolio including the likes of Carta, Lyft, Twilio, Auth0 and Lucidchart to name a few incredible companies. Prior to K9, Manu was either the founder or co-founder of 4 companies, 3 of which with successful exits and the 4th being the fantastic Carta. Manu also has an incredible model with K9 where he not only invests in companies but also founds them and is currently the founder and CEO @ HiHello, the company that allows you to network smarter providing digital business cards designed to help you curate and grow your network. In Today's Episode You Will Learn: 1.) How Manu made his way into the world of venture having founded 4 prior companies and how he came to found K9 and be one of the OG's of pre-seed funding, having coined the term? 2.) What does Manu believe have been the biggest and most significant changes in the early stage market over the last 7 years? How does Manu evaluate the rise of operator and scout funds? Would Manu agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed?" What advice does Manu give to founders on taking multi-stage money at seed? How does Manu evaluate their aggressive movement back into the seed stage? Why is it? 3.) Given Manu only makes 3-4 new investments per year, how does Manu think about and assess his own portfolio construction today? How does Manu think about building temporal diversification into the portfolio? What does Manu believe is the biggest mistake early-stage managers make in the first few years? Why does Manu believe that "group think" is so dangerous for funds today? What can they do deliberately to avoid it? 4.) Manu not only invests but also founds companies at the same time, how does Manu split his time and what does his day look like? What are the benefits of investing and operating simultaneously? What are the biggest challenges and drawbacks? What elements did Manu believe as an investor before starting his new company, HiHello, that he has now changed his mind on, post founding the company? Items Mentioned In Today's Show: Manu's Fave Book: How to Win Friends and Influence People Manu's Most Recent Investment: Workona: A Better Way To Work As always you can follow Harry, The Twenty Minute VC and Manu on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Misha Esipov is the Founder & CEO @ Nova Credit, the startup that allows you to use your international credit history to apply for credit cards, apartment rentals, loans and more. To date, Misha has raised over $69M with Nova from some of the best in the business Kleiner Perkins, Index, First Round, Pear and Core Innovation Capital to name a few. As for Misha, prior to changing the world of credit history, he spent over 5 years in the more traditional world of finance including time at Apollo in the world of private equity and then also Goldman Sachs in the world of investment banking. If that was not enough, due to the incredible impact Nova is having, Misha also sits on the board of World Education Services. In Today's Episode You Will Learn: 1.) How Misha made his way from the world of investment banking and private equity with Goldman and Apollo to changing the way we think about international credit with the founding of Nova? 2.) How does Misah think about and asses both risk and value creation? How did Misha's time at Goldman Sachs influence his operating mentality and how he thinks about the value of data today? Why does Misha find the growth at all costs and revenue later mindset challenging? What core fundamentals around unit economics did Misha establish early with Nova? How does Misha advise founders when it comes to unit economics? 3.) Misha has raised over $69M from some of the best, how did Misha find the process of fundraising? Where specifically does Misha believe his investors provide outside value? What is the optimal way to use an investor in the recruitment process? Where does Misha believe investors could do better and improve? How does Misha advise founders when it comes to manager selection? 4.) How does Misha manage the psychology of being CEO? How does he deal with the shit hit the fan moments? How has his role changed over the last 3 years? What elements have been the most challenging to learn and scale? 5.) How does Misha advise founders on building a diverse pipeline of recruitment candidates from day 1? Why does Misha believe that no recruitment firm can solve for diversity? What is his process as a result for ensuring a truly diverse team? What works? What does not? How does Misha building a culture of accountability? How does Misha think about optimising internal decision-making? Items Mentioned In Today's Show: Misha's Fave Book: Mastery (The Robert Greene Collection) As always you can follow Harry, The Twenty Minute VC and Misha on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Toni Schneider is a Partner @ True Ventures, one of the valley's leading early-stage firms with a portfolio including the likes of Peloton, Hashicorp, Fitbit, Automattic (Wordpress) and Tray.io to name a few. As for Toni, he has spent 14 years as a Partner @ True but during that tenure, he was also the CEO of Automattic for 8 years where he helped WordPress.com become a top 10 global internet destination with close to a billion monthly visitors. Before that, he was a VP @ Yahoo post their acquisition of the company he was CEO of Oddpost, much of their work formed the basis for Yahoo mail. (Note: Recorded Pre-Coronavirus) In Today's Episode You Will Learn: 1.) How Toni made his way into the world of venture following two turns in the seat of CEO and then joining Yahoo? 2.) Does Toni fundamentally believe it helps when investing to have been both an operator with Automattic and Partner @ True? How did being CEO @ Automattic shape how he thinks about investing today? How did Toni manage the balancing act of a being a CEO and Partner at a venture fund for 7 years? Having been a CEO and having worked with the best, what does Toni believe are the qualities that make the great CEO of today? 3.) Why does Toni believe that startups do not have to be as stressful as they are or are portrayed to be? How does Toni deal with the shit hit the fan moments? What can an investor do in times of high stress when the founder is not performing? What is the right way for them to express that the performance is not where it needs to be? On the flip side, what is the right way for investors to show their support to the founders? 4.) What are Toni's biggest learnings from the Wordpress days on what it takes to run a truly successful remote team? Where does Toni see many people going wrong today? What does Toni advise those considering going remote first? What does Toni believe are the biggest pros and cons of the model? What infrastructure does one need to have in place to make it seamless? Does it still make sense for companies to be in the valley? Items Mentioned In Today's Show: Toni's Fave Book: Their Eyes Were Watching God, Predictably Irrational: The Hidden Forces That Shape Our Decisions Toni's Most Recent Investment: Piavita As always you can follow Harry, The Twenty Minute VC and Toni on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Adena Hefets is Co-Founder @ Divvy Homes, the startup that turns your monthly rent into a down payment allowing you to get on the property ladder, sooner. To date, Adena has raised over $189M with Divvy from some of the best in the business including a16z, Ray Tonsing @ Caffeinated, Max Levchin, DFJ and Threshold Ventures to name a few. Prior to founding Divvy, Adena was an early-stage fintech investor at DF. Before the world of venture, Adena was part of the original team that started Square Capital and grew the product to over 10,000 advances ($50M) within 1 year. Finally, before that, Adena started her career in the world of private equity with TPG. In Today's Episode You Will Learn: 1.) How Adena made her way from the world of venture with DFJ to changing the way we think about homeownership with Divvy? 2.) What does Adena believe are the 3 addictions of many early-stage startup founders? How does Adena advise founders on the right way to think about paid marketing? What have been some surprising lessons from seeing Divvy's CAC change over time? How does Adena advise founders to construct a playbook and cadence for hiring? 3.) How does Adena think differently about unit economics today? Is it fundamental to have this mindset from Day 1? Where does Adena believe many founders go wrong when it comes to unit economics? Who is to blame for this desire for synthetic growth? The founders? The VCs? 4.) Considering female founders get a tiny portion of VC funds raised, how was the fundraise for Adena with Divvy? How does Adena advise other female founders and minorities on fundraising successfully? Does Adena believe that founders should always be raising? How does raising debt differ to raising equity? Why is it so much more challenging? 5.) Why does Adena believe that micromanagement can be beneficial in the early days? How does Adena ensure that it does not lead to dependencies and dejected team members? What does Adena to do push people to really get the most out of them? What works? What does not? Items Mentioned In Today's Show: Adena's Fave Book: Evicted: Poverty and Profit in the American City As always you can follow Harry, The Twenty Minute VC and Adena on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Matt Mochary coaches some of the world's leading venture capitalists and founders helping them to build the best organizations possible. On the VC side, Matt has worked with Peter Fenton @ Benchmark, several Sequoia Partners, Hemant @ GC and Mamoon @ Kleiner to name a few. As for founders, Matt has worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport and more. Prior to coaching, Matt began his business career as an investor with Spectrum Equity Investors. He then co-founded Totality, eventually sold to MCI/Verizon. In his own words, Matt went on to have fun (making the Academy Award short-listed documentary Favela Rising) and do good (starting the Mochary Foundation). In Today's Episode You Will Learn: 1.) How Matt made his way from growth investor to immensely successful founder to now coaching the world's leading investors and founders? 2.) How does Matt advise founders to think about their relationship towards fear and anger? Why doe they generate bad quality of decision-making? What should be done when one recognises they are fearful or angry? Where do many founders and investors go wrong here? 3.) How does Matt advise founders who struggle with issues of self-doubt and imposter syndrome? What process should they go through to gain their confidence? What should they not do? How should they communicate their self-doubt to their team and the world? 4.) How does Matt advise founders in terms of the optimal communication strategy both with their team and their co-founders? Does radical transparency need to be instant or should it be timed correctly? What are the best conflict resolution strategies between founding teams? 5.) Why does Matt believe boards are the death of investors? Why are board members not optimally placed to advise their founders? What does Matt believe makes the best board members having worked with the likes of Peter Fenton? What does Matt advise new board members to be the best board member they can be? As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Iman Abuzeid is the Founder & CEO @ Incredible Health, the startup that connects hospitals with nurses and other high shortage healthcare professionals to dramatically speed up the hiring process. To date, Iman has raised over $17M with Incredible Health from some dear friends of the show including NFX, a16z, Charles Hudson @ Precursor and Obvious Ventures to name a few. As for Iman, prior to Incredible, she was a medical doctor, a McKinsey alumnus and led product management at AliveCor, a Khosla-backed health tech startup. In Today's Episode You Will Learn: 1.) How Iman made her way into the world of startups from a family of surgeons and then through being a medical doctor herself? 2.) How was the fundraising process for Iman as a female minority founder? What advice would Iman give to other women and/ or minority when it comes to getting the very best investors? Where does Iman see so many founders make mistakes raising? How should founders structure their meetings with VCs? 3.) Where does Iman believe VCs can be most helpful? Where do many think VCs are helpful but they are actually not? What does Iman think of the "VC Twitter" ecosystem at play today? What investors said no along the way but Iman really liked? Why? Why does Iman believe MBA's provide such an advantage to startup founders today? 4.) How does Iman manage the psychology of being a CEO? How does Iman deal with moments of self-doubt and imposter syndrome? How has Iman seen herself evolve and change as a leader over the last 3 years? What elements have been the most challenging to come to grips with? 5.) Why does Iman still believe if you are not building your startup in the bay, you are missing out? What is so special about Silicon Valley? What advice does Iman give to founders looking to build a diverse team from day 1? How does Iman think about inevitable hiring mistakes? When is the right time to pull the plug? Items Mentioned In Today's Show: Iman's Fave Book: The Hard Thing About Hard Things As always you can follow Harry, The Twenty Minute VC and Iman on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mark Goldberg is a Partner @ Index Ventures, one of the leading venture firms of the last decade with a portfolio including the likes of Dropbox, Revolut, Supercell, Plaid and Transferwise to name a few. As for Mark, since joining Index he has largely specialised on all things financial services and sits on the board of Plaid, Nova Credit, Intercom, Pilot and more incredible companies. Prior to Index, Mark spent 3 years in BizOps at Dropbox where the company increased tenfold during his time there. In Today's Episode You Will Learn: 1.) How Mark made his way into the world of venture with Index having spent 3 years at Dropbox during a transformational time for the company? What were Mark's biggest takeaways from seeing the growth cycle at Dropbox? How did that impact his investing mindset with Index? 2.) Why does Mark believe that venture as an asset class is commoditising? What does Mark believe the best funds will have to do to stay ahead? How does Mark build relationships of trust and authenticity so early with founders? What works? What does not? What is the right way to deliver direct and tough feedback to founders? 3.) How does Mark feel about multi-stage funds re-entering seed investing again? What are the right questions seed founders should ask multi-stage funds when determining whether to take their money? What does Mark believe it takes to be competitive and win the very best of deals? How is the Founder <> VC dynamic changing with capital supply? 4.) Why does Mark believe that most angels are going to lose their money? What does Mark wish all angels knew when they started? How does Mark feel about the rise of founders investing alongside operating? What are the pros? What are the cons? How does Mark feel about the rise of scout funds? Where is there place in the ecosystem? 5.) We are seeing unparalleled levels of activity in fintech, is this a boom or are we at the start of a fundamental shift in the landscape? Why does Mark believe we will soon see our first $100Bn neo-bank? Why does Mark believe we will see a strong rise in the consolidatory environment for fintech moving forward? Items Mentioned In Today's Show: Mark's Fave Book: Barbarian Days: A Surfing Life As always you can follow Harry, The Twenty Minute VC and Mark on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tomer London is the Co-Founder @ Gusto, the people platform for small businesses providing one place to run payroll, manage benefits, and support your team. To date, Tomer and the team have raised over $520M with Gusto from some of the industry's leading investors including General Catalyst, CapitalG, Kleiner Perkins, T Rowe, Fidelity and more and then individuals including Shopify Founder Tobias Luttke, Sam Altman, Max Levchin, Matt Mullenweg, Kevin Hartz and Elad Gil to name a few. Prior to Gusto, Tomer did a PHD in Electrical Engineering at Stanford and before that was Founder and CEO @ Vizmo, mobile self-service technologies for enterprise to try to fix customer care. In Today's Episode You Will Learn: 1.) How Tomer made his way from creating inventory management software for his Father's small business in Israel to Stanford and founding the unicorn that is Gusto? 2.) Why does Tomer believe that most founders approach fundraising with the wrong mindset today? What does he mean when he says, "fundraising = creating change"? What is the "values motivation alignment"? How can founders use it to help them select the right investor for them? Why should you add investors just as you would new team members? 3.) Having raised over $200M in the latest financing, how does Tomer think about when is the right time to pour fuel on the fire and go big? Is it a fundamentally different mindset when you have so much cash thrown on you? What would Tomer advise founders with suddenly expanded budgets? With 111 investors on the Gusto cap table, what would Tomer advise founders when it comes to cap table management? 4.) What have been Tomer's biggest learnings when it comes to building a delightful product at scale across different segments? How important does Tomer feel time to delight from the UX perspective is? How does Tomer think about testing levels of user delight? NPS? Product analytics? How does Tomer think about the balance between product development and going all out for scaling? 5.) How has Tomer seen himself change and evolve as a leader of the last 5 years? What elements has he found super challenging to come to grips with? Where does Tomer believe he has a superpower on the flip side? Question from Laela @ CapitalG, what specifically did you do to create the culture that you did in the early days? Items Mentioned In Today's Show: Tomer's Fave Book: No Room for Small Dreams: Courage, Imagination and the Making of Modern Israel As always you can follow Harry, The Twenty Minute VC and Tomer on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Vinod Khosla is the Founder @ Khosla Ventures, one of the valley's most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Vinod, he started his career as a Founder, founding Daisy Systems, a company that went on to IPO. Then in 1982, Vinod founded Sun Microsystems where he pioneered open systems and commercial RISC processors. In 1986, Vinod joined his longtime friend, John Doerr and became a General Partner @ KPCB where he helped incubate Juniper Networks and helped transform the telecommunications business with Cerent Corporation, which was acquired by Cisco Systems in 1999 for $7.2 billion. In Today's Episode You Will Learn: 1.) How Vinod made his way into the world of startups with the founding of Daisy and Sun Microsystems and how that led to his entry into the world of venture with KPCB and ultimately founding Khosla Ventures? 2.) How does Vinod feel about the term "venture assistance" today? Where does Vinod believe VCs can really drive value? How does Vinod allocate his time to drive as much value for the portfolio as possible? How does Vinod get involved when it comes to talent acquisition for the portfolio? 3.) Why does Vinod believe that most board members are not qualified to advise entrepreneurs today? Why does Vinod believe that most value is driven outside of the board? What can founders to do make their boards as efficient as possible? How does Vinod advise founders to determine which advice to take vs which to disregard? 4.) How does Vinod assess his own approach and attitude to risk today? What does Vinod believe are acceptable vs unacceptable risks in startups? How does Vinod believe the very best founders think about risk management? Does Vinod agree time is the biggest killer of startups? Why does Vinod believe startups are so much quicker to innovate than incumbents? 5.) Why does Vinod believe that tolerance for failure has gone down in Silicon Valley? How does Vinod determine between the realism of when something is not work and to give up vs the visionary persistence to see a project through to the very end? What experience of his own have really led his thinking here? Items Mentioned In Today's Show: Vinod's Fave Book: Life on the Edge: The Coming of Age of Quantum Biology, The Third Pillar As always you can follow Harry, The Twenty Minute VC and Vinod on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Emmett Shear is the Co-Founder & CEO @ Twitch, the world's leading live streaming platform for gamers and the things we love. Prior to Twitch's exit to Amazon for a reported $970M, Emmett raised over $42M in funding from some of the best including Thrive Capital, Bessemer, Mike Maples, Aydin Senkut, Paul Graham and Y Combinator. Emmett is also a part-time Partner @ Y Combinator, advising YC companies on everything from fundraising strategy to product decisions to hiring and firing. Before Twitch, Emmett co-founded Kiko, a company he later sold on eBay for 6 figures. In Today's Episode You Will Learn: 1.) How Emmett made his way into the world of startups with Kiko? How he ended up selling that for 6 figures on eBay? How that led to the creation of Justin.TV & Twitch? 2.) Why does Emmett believe starting a startup is like "deciding to take on the burden of Sisyphus?" At what point in the journey does is start to get easier? Does Emmett agree with many on the show who say, "it does not get easier, it just gets different"? How does one know when to give up vs when to persist and follow the vision? 3.) How does Emmett think about structuring an org at 1,500 people? Why does Emmett believe there is a fundamental tension when scaling teams between centralisation and decentralisation? How does one structure a reorg without causing instability? How does one communicate the reorg to the team? Where does Emmett see many go wrong here? 4.) Does Emmett agree the best CEOs are the best resource allocators? How does Emmett approach internal resource allocation today between both functions and projects? What does he find most challenging here? What does the decision-making process look like? What are his taekaways from Apple, Amazon and Microsoft in how they determine and process resource allocation internally? 5.) How does Emmett believe he has changed and evolved as a leader over the last 10 years with Twitch? What elements has he found the most challenging to master? What has he done to combat those weaknesses? Where has he always been naturally strong? What makes him so good at those particular functions? Items Mentioned In Today's Show: Emmett's Fave Book: Order without Design: How Markets Shape Cities As always you can follow Harry, The Twenty Minute VC and Emmett on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast's leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine's "100 Most Influential People in the World". In Today's Episode You Will Learn: 1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently? 2.) How does Ashton's background in the world of media impact Sound's investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound? 3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through? 4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify? 5.) What have been Ashton's learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton's check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today? Items Mentioned In Today's Show: Ashton's Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies Ashton's Most Recent Investment: Community As always you can follow Harry, The Twenty Minute VC and Ashton on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today's Episode You Will Learn: 1.) How Gabriel made his way into the world of startups and came to found one of today's leading search engines and privacy companies in DuckDuckGo? 2.) Gabriel decided to raise $13M from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today? 3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG? 4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies? 5.) DDG is 83 people and fully remote, what have been Gabe's biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale? Items Mentioned In Today's Show: Gabe's Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business As always you can follow Harry, The Twenty Minute VC and Gabe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jude Gomila is the Founder & CEO @ Golden, creating the world's first self-constructing knowledge database built by artificial and human intelligence. To date, Jude has raised from some of the best in the business including Founders Fund, a16z, SV Angel and one of my dearest friends, Josh Buckley. Jude is also a prolific angel having invested in over 150 companies including Carta, Airtable, Superhuman, Gusto, Linear and many more incredible companies. Prior to Golden, Jude started Heyzap (now used by 100,000 mobile apps) alongside former guest Immad, now Founder of Mercury. In Today's Episode You Will Learn: 1.) How Jude made his way into the world of tech and Silicon Valley having been born and raised in Harrow, London? How did he then make his way into the world of investing? 2.) What models should investors and founders have common ground on? Where are founders and investors often misaligned? What does Jude mean when he says he uses "algorithms for investing"? How are these algorithms structured? What is within them? How can/should people build their own? 3.) Why does Jude very much disagree with spray and pray to be the dominant model to make money at seed? How does Jude think about portfolio construction having now made 180 investments? How has Jude's approach and attitude to ownership changed over time? 4.) Does Jude agree with Semil Shah that founders are voting with their feet and taking multi-stage money at seed today? How does Jude evaluate the approach of multi-stage funds back into seed? How does Jude think about VC value add? Where does he believe they really can add value? Where do people think they do but they actually do not? 5.) How does Jude foresee the future of the early-stage market? Will we see a generation of old school venture firms die out? Why does Jude believe younger investors have a higher chance of finding and winning the next best deal? How does Jude believe the angel ecosystem will shake out? Will we fundamentally see the unbundling of capital? Items Mentioned In Today's Show: Jude's Fave Book: Godel, Escher, Bach: An Eternal Golden Braid Jude's Most Recent Investment: Linear As always you can follow Harry, The Twenty Minute VC and Jude on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shoaib Makani is the Co-Founder & CEO @ KeepTruckin, the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world's leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob. In Today's Episode You Will Learn: 1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today? 2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful? 3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject? 4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC's on incumbent platforms? 4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house? Items Mentioned In Today's Show: Shoaib's Fave Book: Presidents of War As always you can follow Harry, The Twenty Minute VC and Shoaib on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Todd Jackson is First Round Capital's newest Partner (announced today) having spent the last 2 years as a Founder-in-Residence working with the FRC portfolio. Prior to his time in venture, Todd spent close to 3 years at Dropbox as VP Product & Design. Before that he was with Twitter as Director of Product Management, following his startup, Cover, being acquired by Twitter in 2014. Before founding Cover, Todd was a Product Manager @ Facebook where he helped lead major redesign of Newsfeed. Finally, Todd started his career at Google as a Product Lead taking Gmail from 0 to 200m users in 4 years. Todd is joined today by his Partner @ First Round, Phin Barnes. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must-read. In Today's Episode You Will Learn: 1.) Phin, what is the exclusive news you would like to break on the show today? Todd, taking one step back, how did you make your way to this stage, what was your entry into technology and how did you come to be a Partner @ First Round Capital today? What were Todd's biggest takeaways from working on some of the most transformative social products in Gmail, Twitter, Newsfeed @ Facebook and Dropbox? 2.) What advice does Phin have for Todd when it comes to entering a venture partnership? Where do many people go wrong in their first year in venture? What should Todd be optimising for in the partnership? In terms of measurement, how does one measure success of the first year of work as a Partner? 3.) Todd, making the move from angel to institutional VC is a mindset shift, how does Todd think his investment mentality will be impacted by the shift from angel to institutional VC? Having raised funding as a founder, what type of founder experience and investor does Todd want to be and bring? 4.) Phin, it has been a long time since FRC added a Partner, walk me through the recent changes at the top of FRC? What are the most important qualities for First Round when adding a Partner? What are the biggest tips to doing generational transition well? Where do many firms go wrong in generational transition? Items Mentioned In Today's Show: Todd's Fave Book: Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs, Trillion Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell Todd's Most Recent Investment: Papaya Payments, Snackpass As always you can follow Harry, The Twenty Minute VC and Todd on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Businesses are always looking for ways to shorten their sales cycles. HelloSign provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They're an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don't let pen and paper processes slow you down. Click Here to join the millions of users already using HelloSign to close more deals faster!

Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller "Financially Fearless" and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House. In Today's Episode You Will Learn: 1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC's largest-ever female-led VC fund in the form of Inspired? 2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here? 3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round? 4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation? Items Mentioned In Today's Show: Alexa's Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact Alexa's Most Recent Investment: Snackpass As always you can follow Harry, The Twenty Minute VC and Alexa on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Katie Stanton is the Founder and General Partner of Moxxie Ventures, investing in founders who make life and work better. Prior to Moxxie, Katie was a Founding Partner of #angels and has the most incredible angel portfolio including Airtable, Carta, Cameo, Coinbase and Modern Fertility to name a few. Katie also served in numerous executive operating roles at Twitter, Google, Yahoo, and Color and also served in the (Obama) White House and State Department. If that was not enough, Katie is also on the board of Vivendi and previously sat on the board of Time Inc. In Today's Episode You Will Learn: 1.) How Katie made her way into the world of tech with Yahoo? How did that translate into her investing in Lowercase Fund I? How did the angel investing lead to founding Moxxie? How has Katie found her investment mindset has changed moving from angel to VC? 2.) How did Katie find the fundraise for Moxxie? How many LPs did Katie meet and how did she structure the process? What does Katie think she did well in the fundraise? What would she look to improve or change when raising for Fund II? What advice was Katie given in the process by Semil Shah which really changed her thinking? What advice would Katie give to other emerging managers raising today? 3.) Does Katie agree with Semil Shah that "founders are voting with their feet in taking multi-stage money at seed"? What advice does Katie give to founders who do have these offers from multi-stage funds at seed? How does Katie assess these later stage funds moving earlier? How should smaller micro-managers respond to this? 4.) How does Katie think about portfolio construction today with Moxxie? What are the hard rules that mean Katie is willing to walk away from a deal? How does Katie think about and assess her own price sensitivity? In terms of decision-making, what support system has Katie built around herself to enhance her decision-making process? 5.) How does Katie advice founders when it comes to selecting their VC? What are the most common ways founders look for and need to help with? How does Katie think about party rounds? When are they good? When are they not? Why does Katie believe so much of the power has shifted to the hands of the founders? Items Mentioned In Today's Show: Katie's Fave Book: Becoming by Michelle Obama, Angel by Jason Calacanis Katie's Most Recent Investment: ethel's club As always you can follow Harry, The Twenty Minute VC and Katie on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rick Nucci is the Co-Founder & CEO @ Guru, the knowledge management platform that delivers everything you need so you can spend less time searching and more time doing. To date, Rick has raised over $38m with Guru from some of the best in the business including Thrive, Emergence Capital, Firstmark, Slack and Salesforce. Prior to Guru, Rick was the Founder of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was ultimately acquired by Dell where Rick went on to grow the organisation into the industry leader it is today. In Today's Episode You Will Learn: 1.) How Rick made his way into the world of startups originally and how he came to change the way we think about knowledge management with his founding of Guru? 2.) How would Rick describe his leadership style today? How has he seen his style change over the years? What have been those learnings and the inflexion points causing them? Does Rick believe can be learned as a leader? What does he recommend to founders wanting to become more empathetic? 3.) Culture is a fluffy and overused term, what does it mean to Rick? What has Rick done to purposefully build a very specific culture that he wanted to create? What specific initiatives have worked well? What have not worked so well? How does Rick think about culture maintenance with scale? What are the challenges with scaling culture? 4.) How does Rick think about the interview process when adding to the team at Guru? How do they literally structure it? What does their culture interview encompass? How heavily is it weighted? What specific questions do they ask and responses they look for? If it does not work out, what have been Rick's biggest lessons on letting people go? 5.) Rick is based in Philadelphia, often people say if you are not in a tech hub it is not possible to get the best talent, does Rick agree with this? In what roles does it make sense to hire from a tech hub for? What are the advantages of hiring outside of a hub? Fundraising wise, does Rick believe you have to have a presence in a core hub to raise from Tier 1 VCs? Items Mentioned In Today's Show: Rick's Fave Book: The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace As always you can follow Harry, The Twenty Minute VC and Rick on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, "When I see memos from Howard Marks in my mail, they're the first thing I open and read. I always learn something." In Today's Episode You Will Learn: 1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard's life? 2.) Where does Howard think we are in the cycle today? What leads his thinking here? What is it crucial for all investors to remember at any point in the cycle? From a risk distribution and diversification perspective, does Howard believe now is a better or worse time to increase risk? 3.) Having worked through and been at the forefront of some of the most significant downturns of financial markets, what have been Howard's biggest learnings from seeing the booms and busts? How did it impact his investment mindset? At a point in 2008, Oaktree were deploying $600M per week for 15 weeks running, so how does Howard think about when is the right time to be aggressive vs when to pullback? 4.) How does Howard think about and assess his own price sensitivity? If there is one thing Howard wants to know to determine the right price, what is it? How does Howard believe we are seeing pro-risk mindsets alter investors attitude to price? How does Howard think about his right vs wrong and consensus vs non-consensus matrix? 5.) Howard and his Partner, Bruce have a very special relationship, what have they done to foster a relationship of radical intellectual honesty and that environment of safety? What are some things Howard will say to his team to encourage productive disagreement? What to Howard is the most important skill an investor can have is? Items Mentioned In Today's Show: Howard's Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets 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.

Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures. In Today's Episode You Will Learn: 1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital? 2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal? 3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively? 4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes? 5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today? Items Mentioned In Today's Show: Sumeet's Fave Book: Howard Marks: The Value of Predictions As always you can follow Harry, The Twenty Minute VC and Sumeet on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Samir Kaul is a Founding Partner and Managing Director at Khosla Ventures, one of the valley's most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Samir, he led the firm's investment in Guardant Health, Impossible Foods, Nutanix [NASDAQ: NTNX], Oscar, among others. Prior to Khosla, Samir spent five years at Flagship Ventures where he started and invested in early-stage biotechnology companies, including Helicos Biosciences which went on to IPO. Samir was also founding CEO of Codon Devices and led the Arabidopsis Genome Initiative at Craig Venter's Institute for Genomic Research. In Today's Episode You Will Learn: 1.) How Samir made his way into the world of venture from the world of biotech and came to found one of the leading firms of the last decade? 2.) How did seeing the booms and busts of the last 2 decades impact Samir's investing mindset? Why does Samir think it is dangerous for a VC to have a "conservative mindset"? How does Samir analyse and think about upside maximisation when investing today? How does Samir think about when to sell your position and how to determine the right time? 3.) What does investment decision-making look like at Khosla? What are the criteria that re-investments are made upon? Why does Samir believe that pro-rata is a kop out? Which should be the core questions that determine whether to double down or not? How does Samir and the partnership think about time allocation across the portfolio? 4.) How does Samir approach the exercise of market sizing? Why does Samir never want to take a risk when it comes to market? Why does Samir want to maximise his risk when it comes to technological risk? How does Samir think through having to carry these deep tech companies for longer? What were his learnings from the clean tech days on this? 5.) How would Samir analyse his own price sensitivity today? What was his most formative inflexion moment as an investor? What did he learn from it? From a people side, who had the biggest impact on Samir as an investor? What were the core elements he learned from them? How does Samir deal with the element of self-doubt? How does he get through those moments? Items Mentioned In Today's Show: Samir's Fave Book: Start Something That Matters Samir's Most Recent Investment: Lightship: Direct to Patient Clinical Trials As always you can follow Harry, The Twenty Minute VC and Samir on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kurt Rathmann is the Founder & CEO @ ScaleFactor, the startup providing an automated bookkeeping solution at its core, bringing all of your company's important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG. In Today's Episode You Will Learn: 1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise? 2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, "when there is money on the table, take it"? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do? 3.) What is Kurt's biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not? 4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally? 5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds? Items Mentioned In Today's Show: Kurt's Fave Book: The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants As always you can follow Harry, The Twenty Minute VC and Kurt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Gaurav Jain is Co-Founder & Managing Partner @ Afore Capital, one of the west coast's leading pre-seed funds with a $124M fund focused purely on pre-seed. To date, they have backed the likes of Petal, BetterUp, BenchSci and Modern Health to name a few. Prior to co-founding Afore, Gaurav was a Principal @ Founder Collective where he was directly involved with some incredible companies including Cruise (Acq. by General Motors for $1B+), Periscope (acq. by Twitter), Airtable and Dia & Co. Before venture, Gaurav spent time in operations both at Google as one of the first engineers for Android and then also founding his own company, Polar, a leading mobile solutions provider with $10m in funding. In Today's Episode You Will Learn: 1.) How Gaurav made his way into the world of venture with Founder Collective and how that led to the realisation that Afore needed to exist in the funding landscape? What were the 3 biggest takeaways for Gaurav from his time at Founder Collective? 2.) Why does Gaurav believe now is the hardest time in the last decade to raise your first institutional round of funding? What is driving these capital reductions at pre-seed? How does Gaurav assess the rise of operator funds and super angels we have seen in the last 5 years? How does Gaurav advise founders on investor selection at pre-seed? 3.) What does Gaurav make of large multi-stage funds entering into pre-seed? Why does Gaurav strongly believe that you cannot apply the same financing product to a different market? Does this mean the multi-stage funds will revert back to later stages? 4.) How is Gaurav seeing Series A funds behaving? Why are they more aggressive now than ever before? What does Gaurav make of the rise of pre-emptive rounds? How does he advise founders on pre-emptive rounds? 5.) How does Gaurav think about portfolio construction today with Afore? What is the right level of diversification across the portfolio to be sufficiently diversified at pre-seed? How does Gaurav think about reserve allocation today? How does the decision-making process compare when comparing initial to re-investment decision? Items Mentioned In Today's Show: Gaurav's Fave Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell Gaurav's Most Recent Investment: Modern Health As always you can follow Harry, The Twenty Minute VC and Gaurav on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn. In Today's Episode You Will Learn: 1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman? 2.) What does Rahul mean when he says, "you can reverse engineer a process to get to product-market fit"? What does Rahul believe is the defining metric which determines your "product-market fit score"? What is Julie Supan's framework? How did Dropbox and Airbnb use it to increase their product-market fit? How can founders implement it into their process? 3.) What can founders do to expand the customer base to include users that currently are "somewhat disappointed"? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we "disregard the users whereby the primary benefit of the product does not resonate"? 4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul's biggest lessons from going through this painstaking process stage by stage? 5.) Finally on fundraising, what does Rahul mean when he says, "always be raising but never be actively raising"? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here? Items Mentioned In Today's Show: Rahul's Fave Book: The Art of Game Design As always you can follow Harry, The Twenty Minute VC and Rahul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rob Salvagno is VP of Corporate Development and Cisco Investments at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco's strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco's history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco's place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette. In Today's Episode You Will Learn: 1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world's largest tech players of the last decade? 2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham's comment of "do not talk to corp dev"? What are the nuances here? How does it differ for consumer vs enterprise? 3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob's biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit? 4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob's most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in? 5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob's lessons on the importance of speed in winning the best transactions? Items Mentioned In Today's Show: Rob's Fave Book: The Poisonwood Bible Rob's Most Recent Acquisitions: CloudCherry, Voicea As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today's Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today's Show: Bill's Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos Bill's Most Recent Investment: Good Eggs As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brandon Deer is VP of Operations & Strategy @ UiPath, one of the world's fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development. In Today's Episode You Will Learn: 1.) How Brandon made his way from being a rising star in the world of venture with Openview to leading one of the fastest-growing companies in history in UiPath? What has been the most surprising element in making the transition from investor to operator? 2.) How does Brandon think about decision-making today? How does he determine what to spend time on vs what to delegate? What does he mean when he says, "you have to think whether it is rubber or crystal?" How does that ultimately guide decision-making? 3.) What does the UiPath software actually do? What is the relationship between RPA and AI? Where do they differ? Where do they intersect? Recently, RPA has seen a meteoric rise, is this sustainable over the long term? How does Brandon respond to the suggestion that RPA is replacing human jobs? What is the human and societal impact? 4.) How does Brandon think about vulnerability in leadership? Why does Daniel and Brandon's relationship work so well today? What has Daniel (Founder) taught Brandon about communicating that vulnerability the right way and authentically? What does Brandon advise founders in terms of being open to their vulnerabilities? 5.) What are the biggest challenges in scaling an organisation to the 1,000+ person organisation that UiPath is today? What breaks When does it break? How does one maintain culture wit such scale? What have been the challenges of building a truly global business from Day 1? How do they look to mitigate them? Items Mentioned In Today's Show: Brandon's Fave Book: The Five Temptations of a CEO: A Leadership Fable As always you can follow Harry, The Twenty Minute VC and Brandon on Twitter here!

Adam D'Augelli is a Partner @ True Ventures, one of the West Coast's leading early-stage funds with a portfolio including the likes of Fitbit, Peloton, Hashicorp, Tray.io, Ring, Automattic (makers of WordPress) and many more amazing companies. As for Adam, he has spent close to 10 years at True where he has led investments in Hashicorp, Ring, Splice and Namely, just to name a few. Prior to joining the world of venture with True, Adam was an instructor at The University of Florida in Business Finance. Before that Adam was the Founder of Perfect Wave Records, a donation-based record label - helping bands better monetize the relationships with their fans. In Today's Episode You Will Learn: 1.) How Adam made his way into the world of venture with True having had a slightly unorthodox start as an Instructor at The University of Florida? 2.) How does Adam think about portfolio construction today with True? Is it still possible to get 20% ownership on first check? Does Adam believe you can build ownership in subsequent rounds? Does this mean we are seeing the end to rounds being co-led? What does Adam make of pre-emptive rounds? How do True respond to them today? 3.) How does True think about initial vs re-investment decision-making? How do the decision processes differ? Does Adam believe it is possible to stack rank companies and allocate capital accordingly? What is the right way to tell a founder you will not be re-investing? How does Adam think about risk maximisation at a company level? 4.) As a partnership, how does True look to create an environment of safety where both conviction and concerns can be expressed? What should partnerships not do? Why is attribution so dangerous to this EQ of the partnership? How does the partnership work with the companies at a company level? How does True view board seats? How does True think about when is the right time to roll off boards? 5.) What were Adam's biggest takeaways from leading Ring's seed to their acquisition by Amazon? How does Adam think about the importance of market vs the importance of people when investing? How does Adam think about company failure, post-mortems and subsequent next steps? Items Mentioned In Today's Show: Adam's Fave Book: Doing Capitalism in the Innovation Economy: Markets, Speculation and the State Adam's Most Recent Investment: Membio 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.

John Vrionis is the Founder and Managing Partner @ Unusual Ventures, the firm that is redefining seed investing and raising the bar for what entrepreneurs should expect from a seed investment firm. Prior to founding Unusual, John spent 11 years as a Partner @ Lightspeed where his investments included Mulesoft, AppDynamics, Nimble Storage and Heptio to name a few. Before Lightspeed John spent time in product management and sales @ Determina and Freedom Financial Network. In Today's Episode You Will Learn: 1.) How did John make his way into the world of venture and come to be a Partner @ Lightspeed? How did that lead to his founding Unusual? How did his father's MS diagnosis change his mentality towards both investing and how he views the world? What were John's biggest takeaways from his 12 years with the Lightspeed partnership? 2.) Where does John feel the bar needs to be raised in venture? What does the current product not offer? What do seed-stage founders fundamentally need? How have Unusual structured the firm to provide this? How was the fundraise for John? What does John know post-closing that he wishes he had known at the beginning? What advice would John give to aspiring emerging managers? Why is LP diversity so important to John? 3.) Why does John believe taking multi-stage money at seed is not in the best interests of the founder? How does John explain this logically to founders? Does John agree with Semil Shah, "founders are voting with their feet and choosing multi-stage funds"? Why does John believe to be truly best in class, you have to specialise? Does this not go against the data of Benchmark, Sequoia, Founders Fund, all generalist funds, having the best returns? 4.) How does John think about being company vs being founder first? What does one do when alignment erodes between the interest of the firm and the interest of the founder? How does John look to build a relationship of trust and honesty with his founders? What works? What does not work? How does John feel about VCs being friends with their founders? 5.) What is the most challenging element of John's role today with Unusual? Who is the best board member John has ever sat on a board with? Why and what did he learn? What would John most like to change about the world of venture today? What would he like to remain the same? Items Mentioned In Today's Show: John's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Give and Take: Why Helping Others Drives Our Success John's Most Recent Investment: Shujinko As always you can follow Harry, The Twenty Minute VC and John on Twitter here!

Emmanuel Schalit is the Founder & CEO @ Dashlane, the company that provides your all-in-one internet shortcut for passwords, payments and personal info. To date, Emmanuel has raised over $192m in funding for Dashlane from some of the best in the business including Jim Goetz @ Sequoia Capital, Rick @ Firstmark, Alex @ Bessemer and Habib @ Rho, just to name a few. As for Emmanuel, prior to founding Dashlane, he was the CEO @ CBS Outdoor in France and before that COO @ La Martiniere Group. In Today's Episode You Will Learn: 1.) How Emmanuel made his way from CEO of 5,000+ people companies to founding Dashlane and changing the world of passwords and identification? How does Emmanuel asses his own risk profile moving from CEO of a large company to starting Dashlane? 2.) Is Emmanuel concerned by the excess capital available today? Why does Emmanuel believe that raising a mega-round makes your life as a founder harder, not easier? What specifically becomes harder? How does Emmanuel advise founders when it comes to burn and capital efficiency? How does Emmanuel think about when is the right time to pour fuel on the fire? 3.) Where does Emmanuel think that VCs do tangibly add real value? Where does Emmanuel believe that despite what some think, VCs do not add value in certain areas? What have been Emmanuel's biggest lessons of operating and managing a VC board? What does he advise founders starting out on this learning curve? 4.) What does Emmanuel believe are the core challenges of scale? What breaks at what specific points? How has Emmanuel seen himself scale in his role as CEO? What have been the most challenging element to scale into? How did Emmanuel get through them and what does he do to mitigate them now? Items Mentioned In Today's Show: Emmanuel's Fave Book: Sapiens: A Brief History of Humankind As always you can follow Harry, The Twenty Minute VC and Emmanuel on Twitter here!

David Tisch is the Founder & Managing Partner @ BoxGroup, one of the leading early-stage firms in NYC with a portfolio that includes the likes of Flexport, RigUp, Ro, Glossier, Clearbit, PillPack and Plaid, to name a few. Recently they raised their first external capital with 2 separate vehicles totalling over $160m. David is also Professor and Head of Startup Studio @ Cornell Tech. Prior to BoxGroup, he was Managing Director of Techstars NYC and before that was an Executive Vice President @ KGB. In Today's Episode You Will Learn: 1.) How David made his way into the world of early-stage investing? How he made the transition from prolific angel investor to raising $160m+ in external capital? Why did David feel now was the right time to raise external funding after 10 years of self-funding? How has taking on external capital changed his investing mindset? 2.) Many suggest that "concentrated seed investing does not work", how does David think about and assess portfolio construction? May others also suggest that, "seed investors are not company builders", does David agree with that? Does David believe investors can change the trajectory of a company? Where can they help the most? Where do many think they help but they actually do not? 3.) Why does David believe that founders do not speak openly about bad experiences with VCs? What have been David's biggest lessons on the right way to turn down an opportunity? Do founders really want direct and honest feedback? Is it actually damaging to give it to them? Why? How does David approach this? 4.) Why does David believe "consumer social is interesting again"? Why was it not interesting for a while? How does that mean David is approaching the category? What does David mean when he says, "for the first time ever there is no channel to arbitrage on the internet"? Is David concerned by the state of CACs today? How much attention does David pay to CAC/LTV in the early days? What are the key signals? Items Mentioned In Today's Show: David's Fave TV Show: Survivor As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Jason Brown is the Founder & CEO @ Tally, the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance. In Today's Episode You Will Learn: 1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that "serial entrepreneurship is overrated"? 2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today? 3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead? 4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why? 5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor? Items Mentioned In Today's Show: Jason's Fave Book: Sapiens: A Brief History of Humankind As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Josh Buckley manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company. In Today's Episode You Will Learn: 1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever? 2.) What does Josh mean when he says, "the best entrepreneurs are cockroaches"? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is "the oversupply of capital"? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates? 3.) As both a fund manager and founder, what have been some of Josh's biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh's operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing? 4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh's biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh's biggest lessons when it comes to payback period and it changing over time? Items Mentioned In Today's Show: Josh's Fave Blog/ Newsletter: Paul Graham Blog As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here!

Ash Fontana is a Managing Director @ Zetta Venture Partners, the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta he started the money side of AngelList, where, he launched online investing, created the first startup 'index fund'. He also ran special projects like AngelList's expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded. In Today's Episode You Will Learn: 1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash's time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval? 2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value? 3.) We often hear the term, "system of record", why is Ash so much more excited by the "system of intelligence"? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency? 4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology? 5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash's favourite optimisation? Items Mentioned In Today's Show: Ash's Fave Book: The Strategy of Life: Teleology and Mechanics in Nineteenth-Century German Biology As always you can follow Harry, The Twenty Minute VC and Ash on Twitter here!

Dom Holland is the Founder & CEO @ Fast, the world's fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years. In Today's Episode You Will Learn: 1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley's hottest new startups in Fast? 2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, "serial entrepreneurship is overrated"? What advice does Domm give to first-time founders? Where do they most often make mistakes? 3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc? 4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans? 5.) Jan Hammer @ Index has discussed Domm's work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today? Items Mentioned In Today's Show: Dom's Fave Productivity Tool: Superhuman As always you can follow Harry, The Twenty Minute VC and Domm on Twitter here!

Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally. In Today's Episode You Will Learn: 1.) How Rick made his way into the world of venture and came to found one of NYC's leading venture funds in the form of Firstmark? 2.) How did seeing the booms and bust of the macro impact Rick's investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, "the biggest challenge of today is the over-supply of capital"? 3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat? 4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important? 5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick's interest when analysing a consumer investment today? How does Rick think about CAC's scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer? Items Mentioned In Today's Show: Rick's Fave Book: Moneyball: The Art of Winning an Unfair Game Rick's Most Recent Investment: Crisp As always you can follow Harry, The Twenty Minute VC and Rick on Twitter here!

Ryan Denehy is the Founder & CEO @ Electric.ai, the company that provides a world-class IT solution that's centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later. In Today's Episode You Will Learn: 1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17? 2.) Having founded 2 prior companies, would Ryan agree with Joe Fernande @ JoyMode in saying that "serial entrepreneurship is overrated"? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling? 3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan's investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself? 4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting? Items Mentioned In Today's Show: Ryan's Fave Book: Barbarians At The Gate As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Lisa Edgar is a Managing Director @ Top Tier Capital Partners, one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge. In Today's Episode You Will Learn: 1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier? 2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad? 3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don't want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund? 4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs? 5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition? Items Mentioned In Today's Show: Lisa's Fave Book: From the Mixed-Up Files of Mrs. Basil E. Frankweiler Lisa's Most Recent Investment: Boldstart Ventures As always you can follow Harry and The Twenty Minute VC on Twitter here!

Vlad Magdalin is the Founder & CEO @ Webflow, the startup that allows you to build better business websites, faster, without coding. To date, Vlad has raised over $73m with Webflow from some dear friends of the show including Accel, Ron @ Rainfall, Brianne @ Work Life, Benjamin Ling and Y Combinator to name a few. Prior to founding Webflow, Vlad was a Senior Software Engineer @ Intuit. Before Intuit, Vlad co-founded Chatterfox, a web application allowing people to stay in touch with groups of friends, family, or co-workers. In Today's Episode You Will Learn: 1.) How Vlad made his way into the world of startups? How did the original idea to democratise the world of design and site creation with Webflow come about? 2.) Webflow has had an unorthodox funding path with their recent $73m Series A, how was it for Vlad raising the seed round with Webflow? What lessons did he learn from that raise? Why did they drive to be breakeven so much earlier than others might? Why did Vlad believe now was the right time to go big and raise the Series A? 3.) Vlad chose to partner with Accel, what advice does Vlad give to founders in determining which funding partner to choose? What makes for the best VC <> founder relationships? What is the optimal way to build those relationships? Where does Vlad believe that VCs can strategically move the needle? Where do many think VCs can really help but they most often cannot? 4.) What have been Vlads biggest lessons when it comes to successful board management? What advice would Vlad give Harry when it comes to joining boards as new board member? What does Vlad mean when he says, the best board members come to the board with the mindset of "servant leadership"? How do they show that in their actions? How can investors create an environment of trust at the board? 5.) Vlad AMA: Why does Vlad believe that it is a distraction for founders to be angel investing alongside their role as a founder? How does he believe this creates a wedge between them and the team? How has having kids impacted how he thinks about operating today? What have been the big takeaways from fatherhood? Items Mentioned In Today's Show: Vlad's Fave Book: Leaders Eat Last: Why Some Teams Pull Together and Others Don't As always you can follow Harry, The Twenty Minute VC and Vlad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz, one of the leading and most prestigious venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Lyft, Coinbase and many more incredible companies. Ben is also the author of the New York Times bestseller, The Hard Thing About Hard Things, and the upcoming Harper Business book, What You Do Is Who You Are, available October 29. Prior to a16z, Ben was Co-Founder and CEO of Opsware, acquired by Hewlett-Packard for $1.6 billion in 2007. Previously, Ben ran several product divisions at Netscape Communications, including the widely acclaimed Directory and Security product line. In Today's Episode You Will Learn: 1.) How did Ben make his way into the world of venture having previously co-founded Opsware? What was the original thinking for a16z? How did seeing the booms and busts of the market as an operator, impact how Ben thinks about investing today? 2.) In the book Ben says, "If soldiers trust the general, communication will be vastly more efficient". What have been Ben's biggest lessons on how to create an environment of trust quickly? As a board member, how does Ben create an environment of trust for the founder? What is Ben's advice to Harry having just gained his first board seat last year? 3.) Ben has said before of the importance of creating "shocking rules". What are the rules for creating these shocking rules? What are the best rules composed of? Given their shocking nature, how does one instil them in the organisation? What does Ben think is the most shocking rule he has implemented at a16z? 4.) What does ben believe that founders can take away from the rituals of the Samurai? Why does Ben believe that "meditating on company downfalls will enable you to build your culture the right way". Why is the negativity so helpful in forming the right culture? How does ben advise founders when their company is struggling, the team knows it and morale is low? What happened at Okta? How did they turn the culture and business around? 5.) Ben has previously spoken about bringing in external leadership from the cultures you want to master. How does one know when is the right time to bring in this external influence? What can we learn from observing Google Cloud's strategy? How does one retain the old culture but augment it with the new? What were some of Ben's biggest hiring lessons when operating? How does Ben get employees to "feel a sense of urgency", when a change needs to occur? Items Mentioned In Today's Show: Ben's Fave Book: The Black Jacobins: Toussaint L'ouverture and the San Domingo Revolution As always you can follow Harry, The Twenty Minute VC and Ben on Twitter here!

Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO. In Today's Episode You Will Learn: 1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015? 2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase? 3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey? 4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion? 5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look? Items Mentioned In Today's Show: Steve's Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan 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.

Arif Janmohamed is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin's Affirm, AppDynamics and many more incredible companies. Some of Arif's most notable companies that he has led or been involved with for LSVP includel; TripActions, Blend, Nutanix, AppZen, MoveWorks and more. Prior to Lightspeed, Arif worked in the corporate business development team @ Cisco as part of transaction leadership and execution on a number of deals including WebEx. Before WebEx, Arif founded WVP Ventures, a student-run venture capital organization. In Today's Episode You Will Learn: 1.) How Arif made his way into venture and came to be one of the valley's leading enterprise investors with Lightspeed? 2.) We are seeing pricing hit 100x ARR multiples, does Arif believe we are seeing enterprise investing as past it's peak? Are we seeing late-cycle momentum investing? Would Arif agree with matt Harris, "Series A pricing does not matter anymore?" How does Arif assess his own price sensitivity today? How has it changed over time? 3.) Why does Arif believe that market risk is the most dangerous risk to underwrite as a VC? How does Arif think about and assess market timing? What has changed over the last few years to unlock such quantums of capital into the enterprise market? With the acquisitions of Duo, Mulesoft, Qualtrics, will we have a next-gen incumbent set or will it be an environment of existing incumbent consolidation? 4.) What does Arif specifically believe founders need to get right when it comes to company design, in order to scale to a $5-10Bn market leader? In terms of the go-to-market, who does Arif think has nailed it most recently? Why? How does Arif test for a founding team's ability to execute on go-to-market when meeting them early on? Items Mentioned In Today's Show: Arif's Fave Book: Stumbling on Happiness, How Not To Die: Discover the foods scientifically proven to prevent and reverse disease Arif's Most Recent Investment: TripActions As always you can follow Harry, The Twenty Minute VC and Arif on Twitter here!