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

Alex Rodriguez is a businessman and the Chairman and Chief Executive Officer of A-Rod Corp, a broad-based investment firm that bets on world-class startups and partners with leading global companies across the real estate, health and wellness, technology, and sports & entertainment industries. While best known as one of the world's greatest athletes (a 14x MLB All-Star and a 2009 World Series Champion with the New York Yankees), for more than 25 years, Alex leads a team of experts building high-growth businesses and is co-owner of the Minnesota Timberwolves. In Today's Episode with Alex Rodriguez 1.) From MLB to Business MVP: How Alex made his transition from one of the world's greatest athletes to the world of business? What does Alex know now that he wishes he had known at the start of his business career? What is Alex running away from? How do his insecurities drive him? 2.) Lessons from Magic Johnson and Warren Buffet: What are some of the single biggest lessons Alex has learned from his time with Warren Buffet? How did Magic Johnson impact Alex's approach to business? What is Magic Johnson's framework? How can others use it as a blueprint for their career? 3.) Alex Rodriguez: The Business Builder and Investor: What has been Alex's single biggest investing hit? What did he learn from it? What has been Alex's single worst investment decision? How did that change his approach? Why is Alex not buying real estate currently? How does he view the future of real estate buying? 4.) Alex Rodriguez: The Father and Son: How did having two daughters impact Alex's approach to business and life? What have been Alex's single biggest lessons from seeing his single mother operate? How does Alex reflect on his own relationship to money? How has it changed?

Vince Hankes is a Partner @ Thrive Capital where he has led the firm's investments in OpenAI, Melio, and Airplane.dev. He currently sits on the board of Airtable, Benchling, Lattice, and Melio. Prior to joining Thrive, Vince was an investor at Tiger Global where he learned the craft of venture from the legend that is Lee Fixel. In Today's Episode with Vince Hankes We Discuss: 1. From Tiger Global to Partner @ Thrive Capital: How Vince made his way into the world of investing with Tiger Global? What are 1-2 of his biggest takeaways from working alongside the legendary Lee Fixel? Why did Vince make the move from Tiger to Thrive? How do the two firms differ? 2. The OpenAI Investment: The Memo: How did the OpenAI deal come to be? What were the round dynamics? Market Evaluation: How did Vince and the team analyze the market top down? Competition: Who did Vince identify as the core competitors to OpenAI? Defensibility: How did Vince think through the long-term defensibility of OpenAI's model? Does Vince believe these models will become commoditised? Price: How did Vince and the team get comfortable with the $29BN price? 3. AI: Hype or Generational Defining Transformation: Trend or Transformation: Why does Vince believe AI will be the defining technology of our generation? Startup vs Incumbent: Does Vince think the value will accrue to the incumbent or the startup? Open or Closed: Does Vince think we will operate in a closed (one model rules them all) environment or an open-source environment with many models? AI Talent: Where does Vince think the majority of the best AI talent will concentrate? Speed: Why would Vince be scared if he were a startup today looking at the incumbents? 4. The Changing Investor: Lessons from Good and Bad: How has Vince changed most significantly as an investor over time? What has been his single biggest investing mistake? How did he learn from it? What has been his biggest investing success? How did that change his mindset? What has Thrive done in their org structure to allow them to make bets very few other firms can do?

Mark Carney is the Vice Chair and Head of Transition Investing @ Brookfield Asset Management, one of the world's leading asset managers with over $800BN in AUM. Mark is also United Nations Special Envoy on Climate Action and Finance. He has also served as Finance Advisor to the British Prime Minister. In addition to this, Mark is on the board of Stripe, PIMCO and The World Economic Forum. In a previous life, Mark spent over a decade as a Central Banker, most recently as Governor of The Bank of England and before that as Governor of The Bank of Canada. In Today's Episode with Mark Carney We Discuss: 1. Is The Banking Crisis Over? What Happened? Why does Mark not believe we are in a banking crisis? Why does he not believe the banking turmoil is over? Was SVB the fault of regulatory mistakes or management mistakes? Is FRB a damaged asset in it's own right or the result of contagion within the banking ecosystem? 2. The Impact of the Banking Turmoil: What Happens Now? What does Mark believe is the future of regional banks? Why does Mark believe we will see massive consolidation in banks coming soon? Should the Fed be guaranteeing all deposits automatically? 3. What Happens To The Macro Now? How does the banking turmoil impact growth rates? Will we definitely go into a recession now? What is the impact on monetary policy? Can the Fed raise rates even higher? What does this mean for the future of money? Why is it a silver bullet for stablecoins? If Mark could bet on China or the US for the next 10 years, who would it be? Does Mark believe the UK is in a weaker situation than ever? What about Europe? 4. The Future of Climate and Net Zero: Where are we at with Net Zero? Are we ever going to make progress? Is it possible to make progress without the cooperation of China? Why does Mark disagree and suggest China has done more than most to help the climate? Who is talking more than they are acting in the fight to save the climate? On the flip side, who is acting more than they are talking?

Sarah Guo is the Founding Partner @ Conviction Capital, a $100M first fund purpose-built to serve "Software 3.0" companies. Prior to founding Conviction, Sarah was a General Partner at Greylock where she made investments in the likes of Figma, Coda, Neeva and many more incredible companies. Sarah also hosts her own podcast, No Priors with the wonderful Elad Gil. In Today's Episode with Sarah Guo We Discuss: 1. From Large Multi-Stage Firm to Founding Conviction: Why did Sarah decide to leave Greylock? What are 1-2 of her biggest lessons from her time at Greylock? How did they impact her mindset when building Conviction today? What does Sarah believe are the most surprising or hardest elements of firm building? 2. The Future for AI: The Opportunities and the Challenges: Why does Sarah believe AI is the most foundational technology of our lifetime? Why did Sarah decide to centre the entire fund around AI? Is AI not an enabling technology that will power all sectors in technology? Is Sarah concerned by the further wealth inequality that AI and billion dollar companies created by 10 people, will inevitably bring? How does Sarah think about the potential for malicious AI use? What can be done to prevent this? 3. Startup and VC Principles That Are BS: Why does Sarah believe that defensibility is BS? Why do Sarah and Harry both believe that reserves in venture funds are a suboptimal use of funds? "Great founder, bad market, market wins". Does Sarah agree? How does Sarah prioritize the centrality of founder vs market? 4. Sarah Guo: The Investor How has Sarah changed most significantly as an investor over the last 5 years? What is Sarah's biggest miss? How did it impact her mindset today? What is Sarah's biggest win? How did that alter her risk appetite? How does Sarah see the future of venture? If Sarah could invest in one multi-stage firm and one seed-stage firm, which would it be?

Jack Brody is the VP Product @ Snap. Jack joined Snap in 2014 as a Product Designer, and ultimately helped build out the design organization as the Head of Design before taking on his current role overseeing all of Product for the Snapchat application and Hardware. In his 9 years at Snap, he helped create Memories, the Snap Map, and AR Lenses like Face Swap. In Today's Episode with Jack Brody We Discuss: The Shortest Internship in Tech: How did Jack get an internship with Evan Spiegel and Snap while he was still at college? How did it turn into the shortest internship in tech history? What are the single biggest product lessons Jack has from working with Evan Spiegel? 2. Product 101: Art vs Science: Does Jack believe product is more art or science? If he were to assign numbers to them, what would they be? How does Jack define creativity? What can founders and product leaders do to ensure their teams are as creative as possible? What is the 3 step framework through which product leaders should prioritize product ideas? Does Jack believe that when the CEO is no longer the Head of Product, the company is dead? Does Jack agree with Gustav Soderstrom, "talk is cheap, so we should do more of it"? 3. The SNAP Hiring Process: What Works and What Does Not: What is the hiring process for the product team at SNAP? What questions are most revealing of 10x product people in the interview process? What case studies and tests does Jack use in the interview process? What other roles and functions does Jack bring into the interview process as part of the decision? What are the single biggest mistakes founders make in the hiring process for product? 4. SNAP, The Future, and The World Around Us: What do Jack and SNAP believe will be the future for augmented reality? What country is SNAP not big in today but will be in the next 5 years? Why that one? Why did SNAP tear down its android app and start again? What has been the impact? Were the SNAP glasses a success? What is their future?

Avlok Kohli is the CEO @ AngelList. Under his leadership, Avlok has taken AngelList from an SPV provider to a company that is becoming the software platform for the entire industry. Today, AngelList supports over $15BN in assets and 40% of US unicorns have had a GP invest in them through AngelList. Prior to becoming CEO @ AngelList, Avlok founded 3 companies, all of which were acquired including by the likes of Square and eBay. In Today's Episode with Avlok Kohli We Discuss: 1. From 3x Founder to Scaling AngelList to $15BN in AUM: How did Naval convince Avlok to join AngelList and be CEO? Does Avlok believe in startups having defensibility in the early days? How important does Avlok believe it is for companies to be "first to market"? Why does Avlok believe all the last-mile grocery delivery companies will go bust in the downturn? 2. What is Going On in Venture: New Funds, LPs, Secondaries: Are we seeing the amount of net new funds reduce in the downturn? Are we seeing the size of new funds being raised, being smaller? Is the time to first close increasing in time? Does AVlok agree that the fund segment hit hardest by the downturn is micro fund managers? Which LP class has pulled back from fund investing most significantly? Why does Avlok believe institutions have returned to fund investing more than ever right now? Are we seeing an increase in fund secondary positions? 3. What is Going on in Startups: Rounds, Valuations, Party Rounds Are we seeing the number of startups able to close their round reduce? Are we seeing the size of startup funding rounds reduce? How does this depend on the stage? What are we seeing for startup valuations? Why is seed as high as ever? What is the most hit? How is the composition of funding rounds changing? More or fewer party rounds? When does Avlok believe we will see down rounds and pay-to-play, really come into effect? 4. The Business of AngelList and its Future: What are the margins on AngelList products today? What is the best margin AngelList product? What is the worst? What product did AngelList do that in hindsight, Avlok wishes they had not done? Why did AngelList back out of Europe? Was it a mistake? How does Avlok think about AngelList's fierce competition with Carta today?

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages. Prior to founding Theory, Tom spent 14 years at Redpoint as a General Partner where he made investments in the likes of Looker, Expensify, Monte Carlo, Dune Analytics, and Kustomer to name a few. Tom also writes one of the best blogs and newsletters in the business which can be found here. In Today's Episode with Tomasz Tunguz We Discuss: Founding a Firm: The Start of Theory: Why did Tom decide to leave Redpoint after 14 years to found Theory? What are 1-2 of his biggest lessons from Redpoint that he has taken with him to his building of Theory? What does Tom know now that he wishes he had known when he started investing? 2. From 150 LP Meetings to Closing $230M: Raising a Fund I How would Tom describe the fundraising process? How many meetings with LPs did he have? How many did he know previously? What documents did he share with LPs? Did he have a dataroom? How did he use it? How did Tom create a sense of urgency to compel LPs to come into the fund? How does Tom feel about the debate between one close and multiple closes? What was the #1 reason LPs said no to investing? What worked and Tom would do again for the next raise? What did not work and he would change for the next raise? 3. Where Will Value Accrue in the Next Decade of AI: Startup vs Incumbent: Will incumbents embrace AI before startups are able to acquire distribution? Infrastructure vs Application Layer: Where will the majority of value accrue in the next decade; infrastructure or application layer? Bundled or Unbundled: Will bundled services be the dominant consumer and enterprise choice or will unbundled specialized solutions win? 4. AI and The World Around It: How does Tom believe AI could save the US economy? Why does Tom believe Google are the losers in the AI race? Which incumbents have responded best to AI? Why does Tom believe we will be in a worse macro place at the end of the year than we are now?

Mark Goldberger is Head of Enterprise Sales at Ramp, the fastest-growing corporate card and bill payment software in America, and recently named Most Innovative Company in North America by Fast Company. Prior to joining Ramp, Mark was the first enterprise rep at TripActions (now Navan), where he helped bring in more than $100m of ARR as an IC and sales leader. Before TripActions, Mark worked at Highfive, a video conferencing company since acquired by Dialpad. In Today's Episode with Mark Goldberger We Discuss: 1. From Wine Industry to Sales Leader: How Mark made his way into the world of enterprise sales having been in the wine industry? Mark sent out 100 CVs for his first sales role, why did they not respond? How should companies think differently about the people they hire? What could he have done better with the outreach? What does Mark know now that he wishes he had known when he entered the world of sales? 2. The Sales Playbook and Why You Should Never Hire a Sales VP First: Why does Mark believe that you should never hire a Sales VP as the first sales hire? What does Mark mean when he says product-customer-fit is more important than product-market-fit? Why does Mark believe that revenue does not matter with your first customers? If revenue does not matter, what should you be trying to get out of them? When should the founder handover sales to either a junior or more senior hire? 3. How to Hire 10x Sales Teams: The Process: How does Mark structure the process for hiring 10x sales reps? What questions are most revealing in identifying a 10x sales rep? How do they respond? Why does Mark want candidates to pitch his own product back to him? How does Mark make the hiring process more challenging to really test the quality of candidates? What is the core difference between losers and winners in sales? 4. Discounting, Champions, Creating Urgency: Why does Mark not like discounting? Where do many sales teams use it poorly? How does Mark like to create urgency in a sales process? What works? What does not? How can sales reps know whether they truly have a deal champion within a buyer? What is the right way for sales reps to ask to meet the exec buyer? When is the right time to ask to meet the exec buyer? What are some clear signs that you are not speaking to a decision-maker? 5. Building a High-Functioning Sales Org: What is the right way to do deal reviews? How often? Who should be invited? What is the right way to do sales onboarding for all new reps? Why is traditional outbound still the most important thing in a sales process? Why do so many people get pipeline qualification so wrong?

From college party promoter to managing global stars to CEO and investor. Scott "Scooter" Braun is one of the most powerful people in media and one of the most multi-faceted entrepreneurs we have ever met. As the founder of media company SB Projects and the co-founder of TQ Ventures, he has backed prominent companies such as Pinterest, Spotify and Uber and managed some of the world's biggest names in music including Justin Bieber, Ariana Grande, and Demi Lovato. Braun's other accolades include founding Ithaca Ventures (acquired by HYBE for $1BN+) in 2021, and philanthropic efforts such as being a Make-A-Wish board member, raising $55M+ for Hurricane Harvey and Irma relief and continuing to instill the value of social good wherever possible. In Today's Episode with Scooter Braun We Discuss: 1. From College Party Promoter to Managing The World's Biggest Superstars: What was the single most catalytic moment of Scooter's career? What was Scooter's most painful professional mistake, and what did he learn from it? What was the decision-making behind Scooter's HYBE deal? What is the biggest challenge in scaling the trajectories of the people Scooter works with? If Scooter could change one thing about the music industry, what would it be? 2. College Party Promoter Turned Venture Investor: How did Scooter originally get into investing? How did Scooter's party promoting business almost lead to an early investment in Facebook? Do people approach Scooter differently as an investor because of his success in the music industry? Why is vulnerability helpful for investing? 3. Scooter's Lessons on Success (And How to Deal With It): Why does Scooter believe happiness and success are not aligned? How does Scooter approach deal-making? Is work-life balance bullshit? Does Scooter think you have to break your back to become as successful as Jeff Bezos? Is Scooter scared of mediocrity? Why does Scooter think all entrepreneurs are bad at having faith? 4. The Secrets to Being a Better Parent, Child, and Partner: How does Scooter approach trust? How did having kids impact Scooter's mindset? Why was divorce the biggest catalyst in Scooter's entire life? Does Scooter worry that money will negatively influence how his children are brought up? What is the most important thing a child can hear from a parent? 5. Finding the "Scott" Buried Inside "Scooter": It's easy to become the brand you create. How does Scooter prevent losing himself when that happens? What does Scooter need to unlearn in the future? What has Scooter changed his mind on in the past 12 months? How does Scooter approach his relationship to regret? What single lesson you most would Scooter most want a young person listening to this conversation to take away?

David Marcus is the co-founder and CEO of Lightspark, building infrastructure that extends the capabilities and utility of Bitcoin. Prior to Lightspark, David led all payment and crypto efforts at Facebook/Meta and scaled Messenger to 1.5BN users. David previously founded three other companies: Zong (acquired by eBay/PayPal for $240M), Echovox (acquired by MBO), and GTN (acquired by World Access). In Today's Episode with David Marcus We Discuss: 1. From Losing Everything to Becoming Changing the World of Fintech: How did seeing his family lose everything lead to David starting his first company, GTN? Does David believe that great companies can be built in Europe? What are the biggest mistakes David made with Zong? How did they impact his mindset? 2. The Secret to Building a Great Company from Mark Zuckerberg's ex-Right Hand Man: Where does David think Paypal lost its way? How did David "brutally" change PayPayl's company culture when he came in? What worked and what didn't in scaling Messenger to 1.5BN users? Why did Diem (formerly Libra) fail? How did David know when to give up that fight? What is David's biggest lesson from working with Mark Zuckerberg? 3. Crypto & AI's Ripple Effect on The Rest of The World: What will be the fallout from the de-banking of crypto? How does David think the future of AI will impact income equality? If David was in charge of the SEC, what would he do first? What worries David most about the next 1-5 years in the crypto industry? What are the most significant signs that the tea leaves not looking great for the US dollar? 4. How The Best Leaders Hire The Best Talent: Why does David believe that naivety is good for entrepreneurs? Does David believe we'll be in a worse macro position by the end of the year? How has David changed most as a leader over time? What is David's biggest piece of advice in regard to hiring across many different companies?

Joost De Valk is one of the OGs of SEO. As the Founder of Yoast, he scaled what was a side project plugin into a multi-million dollar business, used by 13 million sites and selling to Newfold Media in 2021. As one of the early SEO pioneers he is also an extremely coveted angel investor and invests through his company, Emilia Capital. In Today's Episode with Joost De Valk We Discuss: 1. From Side Project to Multi-Million Dollar Business: Why and how did Joost create the first version of Yoast? When did he realise that this was not a side project and could be a big business? What does he know now that he wishes he had known when he started Yoast? 2. When, How and Why To Invest in SEO: When is the right time to invest in SEO? How should one determine how much budget to allocate to SEO? Once decided on budget, what are the first steps to investing in SEO? Which part of the org should SEO team specialists sit in? What are the biggest mistakes founders make when investing in SEO/ 3. AI Changes The World of Context: How does AI change the way businesses create content? How can startups leverage AI to create and distribute more content for SEO? What are the biggest challenges/problems to leveraging AI for content creation? 4. Creating a Developer-Led Brand and Mastering PLG: What is the secret to creating the best developer-led brand? What are the biggest mistakes people make when marketing to developers? How does Joost navigate the balance between having enough value in a freemium product but also retaining enough value to be able to charge for the premium product? Is Joost concerned that budgets will revert back to CFOs and away from individual contributors with the financial downturn that is ensuing?

Rob Lacher founded Visionaries Club in 2019, in just 3 years he has scaled the firm to $600M AUM and backed some of Europe's best including Xentral, Personio, Miro, and Ledgy. Prior to Visionaries, Rob founded the fashion platform AMAZE in 2014 which he sold to Zalando, and founded the European seed and growth stage venture capital fund La Famiglia in 2016. In Today's Episode with Rob Lacher We Discuss: 1.) From Novice Tennis Player to Investing on a Global Stage: When Rob realized beating Federer wasn't an option, how did he make his way into the world of venture capital? When did Rob know he wanted to be a VC? What did Rob learn about himself after leaving La Famiglia? What characteristics make business partners compatible? 2.) The Secret to Building a Fund? Hire People With No Experience: What does Rob think is the hardest element of building a firm? What advice would Rob give to emerging managers when starting their firms? What is the single biggest mistake that Rob sees hiring managers make? Why does Rob prefer to hire people with no VC experience? 3.) The Red Ocean of European Venture: Does Rob think the Series A product in Europe is any good? How would Rob advise founders debating a US multi-stage fund or a European offer? If Rob could choose one European board member, who would it be and why? In Rob's dream, what would the Europe venture ecosystem look like in 2028? How does Rob think Europe's family institutions can become Europe's Google? 4.) Lessons on Investing From a Pro: Where does Rob think VCs, founders, and boards are misaligned? When Rob invests, how central of a role does price actually pay? What is Rob's single biggest investing mistake? How did it impact his mindset and approach? What are the three ways reserve management strategy has changed? What does Rob absolutely hate about VC?

Mike Salguero is the Founder and CEO @ ButcherBox, the meat delivery subscription service that he has scaled to $600M in revenue, 215 employees and the national leader in the space. All of this achieved while raising $0 of venture capital. Prior to ButcherBox, Mike was the Founder & CEO @ CustomMade, an online marketplace that, unlike ButcherBox, raised millions in venture funding from prominent VCs. In Today's Episode with Mike Salguero We Discuss: 1.) The Makings of a Great Entrepreneur: How did Mike's father not being present in his childhood impact the type of leader he is today? How does Mike's fear of abandonment show itself in his leadership style? What does Mike know now that he wishes he had known when he started? 2. Consumer Subscription is Not a VC Backabale Business Model: Why does Mike believe consumer subscription D2C businesses are not VC backable? What are the biggest challenges of running a consumer subscription business? Why did all the D2C food prep and delivery companies fail? What did they do wrong? What happens to all the heavily funded D2C subscription companies of the last 5 years? Why does Mike believe now is the hardest time ever to do D2C consumer subscription? 3. The Secret to Efficient Marketing: How did ButcherBox scale to $50M in revenue with just one marketing channel working? When should founders think about the second channel? How should they choose which one? Why does Mike not like "brand marketing"? How did ButcherBox burn $8.5M on brand marketing? What are Mike's biggest lessons from doing this? What emerging channel does Mike see as having the biggest potential over the coming years? Why does customer acquisition increase with time? Why do elections cause it to increase? 4. The Economics of a $600M Revenue ButcherBox: How much does it cost ButcherBox to acquire a customer? What is their payback period on that customer? How has this change with time? What is the single metric that drives the profitability of ButcherBox? What are the single biggest points of margin in the business? What is the lifetime value of a ButcherBox subscriber? What are the single biggest points of churn in the customer lifecycle? 5. Venture Capital: To Raise or Not to Raise: Why did Mike never raise venture capital for ButcherBox? Has Mike ever sold secondary? Why not? What would Mike most like to change about the world of venture capital? What are his biggest lessons from raising VC with CustomMade? How did that impact how he approached building ButcherBox? What does Mike believe all founders need to know about raising VC?

Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Over an incredible 18 years, Tobi has scaled Shopify to 10% of total US e-commerce, millions of merchants in over 170 countries, and a market cap today of over $60BN. Huge thanks to Harley Finkelstein for making this happen. In Today's Episode with Tobi Lütke We Discuss: 1. From a Small German Town to One of the World's Most Powerful CEOs: What did Tobi want to be when he was growing up? Who did Tobi learn most from in his younger years? How does Tobi think about the importance of mentorship in learning? What does Tobi know now that he wishes he had known when he started Shopify? 2. You Can Learn More from World of Warcraft Than You Can Companies: Why does Tobi believe you can learn more from World of Warcraft than you can from studying companies? Why does Tobi believe that humans are terrible at company building? What are the most obvious ways we can improve the quality of the companies we build? Why does Tobi believe that in-person is far superior to remote working? What are the nuances? 3. The Best Companies Operate with Many Constraints: Why does Tobi believe in all cases, constraints produce creativity? What is the difference between an enforced constraint and an artificial constraint? How can leaders create and enforce artificial constraints when they are not real? How do the best leaders use constraints to ensure their companies move faster and faster? 4. Inside the Mind of Tobi Lütke: Decision-Making & Prioritisation: How does Tobi reflect on his own decision-making process? How has it changed? Why does Tobi believe that sunk cost fallacy is BS and only leads to your outsourcing approval to someone else? Why does Tobi hate "black boxes"? How does he remove them from the org entirely? How does Tobi decide what to learn? What is his learning process once he has made this decision? How does Tobi decide what to prioritise in terms of strategic initiatives for Shopify?

Jackie Reses is the Chair and CEO of Lead Bank, a community bank in Kansas City. Previously, she was the Executive Chairman of Square Financial Services and Capital Lead and Head of the People Team at Block Inc (Square). Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area. Jackie is on the board of directors of Endeavor, Affirm and Nubank. Previously, she served on the Board of Directors of Alibaba Group. She has been named one of Forbes' "Self Made Women", Fast Company's "Most Creative People in Business," and American Banker "Most Powerful Woman in Finance". In Today's Episode with Jackie Reses We Discuss: 1. From Humble Beginnings to "Most Powerful Woman in Finance": What is Jackie running from? How did Jackie's upbringing impact her approach to business and management today? What does jackie know now that she wishes she had known when she started her career? 2. Building the Best Teams: Lessons from Square and Yahoo Why does Jackie believe that past experience is BS in hiring candidates for a role? Why does Jackie deliberately not look for domain knowledge when hiring? Why does Jackie believe employers should tell candidates what they suck at in hiring? What does Jackie mean when she says, "you have to invest in people for 20 years"? 3. The Best Deal-Maker in the Business: Secret to Negotiating: What does Jackie believe is the secret to successful negotiations? How did Jackie do the Alibaba deal for Yahoo and make $50BN for them? Why does Jackie believe the Laffonts and Coatue are the best risk managers? What are the biggest mistakes people make in deal-making today? 4. The Next Wave of Fintech: Who wins and who loses in the next wave of fintech? What will happen to the crypto industry? How will crypto be regulated? Why does Jackie believe that financial super apps are BS? Why does Jackie believe that Goldman tried and failed to innovate? Will we see a wave of M&A in fintech over the coming years?

Jag Duggal is the CPO @ Nubank where he is responsible for product strategy and roadmap reporting to CEO David Velez. Jag leads over 200 professionals across different functions within his role. Before Nubank, he was the Director of Product Management at Facebook, leading monetization of video and third party content. Before Facebook, Jag spent close to 7 years at Quantcast as a Senior VP of Product Management & Strategy. Finally, pre-Facebook, Jag was at Google for 5 years as a Group Product Manager and Head of Strategy (Display). In Today's Episode with Jag Duggal We Discuss: 1. From Cushy Valley Job to CPO @ Brazilian Startup: Why did Jag leave the life of luxury in the valley at Facebook to join David as CPO @ Nubank? What does Jag know now that he wishes he had known when he took the position? What one piece of advice would Jag give to a product leader starting a new position today? 2. Product: The Playbook, Art vs Science: Why does Jag believe that product is 90% science? What is the final 10%? Why does Jag believe that you should not listen to your customers? What is the right way to ask customers questions to determine their pains? Why does Jag believe that you should not fall in love with your own ideas? 3. Building the Bench: Hiring the Best Team: How does Jag approach the hiring process for all new product hires? What are the single biggest mistakes Jag has made when hiring for the product team? What are the must ask questions when hiring for product? What hiring lesson did Jag learn from Kevin Systrom? How has he applied it today? What did Jag believe about hiring that he now no longer believes? 4. Go Time: Build, Manage and Execute: Why does Jag think execution is overrated and strategy deserves more credit than people give it? How does Nubank utilise small teams to operate fastest? What have been lessons here? What are the best ways to do product post-mortems? What works? What does not work? What has been Jag's best product decision? What has been his worst?

Dara Khosrowshahi is the CEO of Uber, where he has managed the company's business in more than 70 countries around the world since 2017. Dara was previously CEO of Expedia, which he grew into one of the world's largest online travel companies. Dara was promoted to Expedia CEO after serving as the Chief Financial Officer of IAC Travel. Before joining IAC, Dara served as Vice President of Allen & Company and spent a number of years as an analyst. He currently serves on the Board of Directors of Expedia and Catalyst.org and was previously on the board of the New York Times Company. In Today's Episode with Dara Khosrowshahi We Discuss: 1. From the Iranian Revolution to One of the Most Powerful CEOs: What is Dara running from? What is he running towards? How did seeing his family lose everything impact his mindset to life and business? What are 1-2 of Dara's biggest lessons from working with the legendary Barry Diller? How did Daniel Ek @ Spotify convince Dara to take the CEO role at Uber? 2. Dara Khosrowshahi: The Foundations of Great Leadership: What does high performance in business mean to Dara? Does Dara agree, "the best CEOs are the best resource allocators"? Does Dara believe he is a better peacetime or wartime CEO? Which is he at Uber? What decision-making framework does Dara use to make really hard decisions? How does Dara does what to focus on and what to prioritise? 3. Investments and Acquisitions: The Scorecard: Why did Dara decide to make the Kareem acquisition? Has it been successful? What was the thinking behind the Postmates acquisition? What does Dara believe is the single best acquisitions he has made at Uber? What has been the worst acquisition he has made at Uber? Why does Dara believe that Uber entering scooters was a mistake? 4. The Future: Food Delivery, Parenting, Marriage: What does Dara say to those who suggest Uber Eats has lost the war to Doordash? What does Dara believe is the secret to a happy marriage? How does Dara define great parenting? What does Dara do to be the best father he can be? What would Dara like to improve or change about himself? Why?

Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Mike has been on the Forbes Midas List eight times in the last decade and was also named a "Rising Star" by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship. In Today's Episode with Mike Maples We Discuss 1.) Lesson from SVB #1: The Importance of Scenario Planning: What is the right way to do scenario planning in startups? What is the difference between good vs bad scenario planning? What do the best scenario plans include and involve? What is the right way to communicate these scenario plans to your stakeholders? 2.) Lesson from SVB #2: The Importance of Financial Agility: What does it mean for a startup to be "financially agile"? From a banking relationships perspective, what can startups do to be financially agile? How many accounts should a startup have? How much runway should be in each? Should startups bank with startup banks as well as traditional banks? Should startups have their money in sweep accounts and money market accounts? 3.) Lesson from SVB #3: How to Master Crisis Communications: Why is it so important for founder to over-communicate in tough times? How transparent should they be in these communications? What does Mike mean when he says "be radically human"? If Mike were to face a crisis, what would he do differently in the way he communicates to his LPs? 4.) Lessons from SVB: The Wider World: Why does Mike believe the level of quantitative easing that occurred in COVID was scandalous? Does Mike believe the USD will continue to be the reserve currency of the world? Will we be in a better or worse macro situation by the end of the year? Has Mike ever had a company that achieved true PMF and failed?

Frank Fillman is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today. In Today's Episode with Frank Fillman We Discuss: 1.) From Selling Kitchen Utensils to Leading $1BN Revenue Line for Salesforce: How did Frank first make his way into the world of sales selling kitchen utensils? Why does Frank believe, "how you handle tragedy defines you"? How did it define him? What does Frank know now that he wishes he had known when he started in sales? 2.) Build and Execute the Sales Playbook: How does Frank define what a "sales playbook" is today? What is it not? Literally, what are the first steps to building a sales playbook? Is it the founder who does it? What does a good playbook have? What does a bad playbook have? What makes the best? What tools should founders and sales leaders use to create their playbook? 3.) Enterprise Deal Dynamics 101: Why does Frank believe that you should never start with the price or "send over numbers"? How can enterprise sellers create urgency in a deal cycle? What works? What does not work? How does Frank advise sales teams on the use of discounting? How open should reps be in communicating the win for them as well as the win for the customer of closing a deal? 4.) Building the Bench: How does Frank structure the hiring process for all new sales reps? Why does Frank believe that all sales leaders want to be super reps? How does Frank rank high potential vs high experience when hiring reps? What matters more; the exec have experience in the sector you are selling into or the deal size? What are the single biggest mistakes founders and leaders make when hiring sales? 5.) Setting Quota and Deal Reviews: How does Frank advise founders on setting quotas? Why does Q1 set the tone for the year? How does Frank conduct deal reviews? How often? With who? What is the agenda? What is the one question that Frank always asks when a rep says, "the client told us it was not a priority and so it slipped into next quarter"? How does Frank advise founders and sales leaders on multi-threading large enterprise accounts? Items Mentioned in Today's Episode: Frank's Most Recent Book: The Go-Giver: A Little Story About a Powerful Business Idea

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets. Bill is also a member of the board of Universal Music Group N.V. He serves as a member of the Investor Advisory Committee on Financial Markets for the Federal Reserve Bank of New York, and a member of the Board of Dean's Advisors of the Harvard Business School. Prior to forming Pershing Square, Mr. Ackman co-founded Gotham Partners Management Co., LLC. In Today's Episode with Bill Ackman We Discuss: 1.) From HBS to Starting Your First Fund: How did Bill go from HBS to raising his first fund in Gotham Partners? How was that first fundraise? From 100 meetings, what worked? What did not work? What were the core fundraising lessons? What did Bill learn about great partnerships from his time with David building Gotham? 2.) Bill Ackman: A Winner's Mindset: How To Deal with the Highs and Lows: On reflection, what have been the most challenging times for Bill professionally? What does he say to himself when he is going through the hardest times? What is his mind talk? When the war is lost and it is time for learning, how does Bill reflect and learn from losses? Bill has previously described himself as "the most persistent man in America". How does Bill know when enough is enough, he was wrong and it is time to change his approach? 3.) Bill Ackman: SVB + Bank Runs and The Future of our Financial System: Why does Bill believe that the depositor guarantees for SVB and Signature Bank have created a "Three Tier Banking System"? What are those three tiers? Why does Bill believe that SVB is now the safest place to deposit your money? Why is First Republic Bank and SVB very different in terms of their exposure? What can be done to prevent further bank runs? What should the Fed be doing? Why are they not doing it? What would Bill do if he was in charge of the Fed? Why does Bill believe the current levels of FDIC insurance are insufficient and outdated? What should be used in their place? 4.) Bill Ackman: The World Around Us & Potential Politician Why does Bill want Jamie Dimon to run for President? If it is Trump vs Biden, who wins? Why does Bill believe Biden's tax policies destroy the US economy? What should we have instead? Why does Bill believe we should give every newborn baby $6,500 and invest it for them when born? What are Bill's 10-Year Long's and 10-Year Shorts? Why them? Would Bill ever run for politics? When is the right time?

Ophelia Brown is the Founder of Blossom Capital, one of Europe's newest but leading early-stage venture firms. Ophelia and the Blossom team have invested in stand-outs including Checkout, Duffel, Tines, and Moonpay. Prior to Blossom, Ophelia was a GP at LocalGlobe and a Principal at Index Ventures where her investments included Robinhood and Typeform. In Today's Episode with Ophelia Brown We Discuss: 1.) From Restaurant-Owning DJ to Leading European VC: How Ophelia made her way into the world of venture and came to found Blossom? What does Ophelia know now that she wishes she had known when she entered venture? What does Ophelia feel she is running away from? 2.) Venture Capital: The Market: Why does Ophelia believe the best venture firms focus either by stage/theme/geography? Why does Ophelia believe that marketing in venture has no substance? How can founders determine between what is real and what is false? Why does Ophelia believe that growth investors have ruined the venture market? When does Ophelia believe VCs will realise that FOMO investing is not a good strategy? 3.) Ophelia Brown: The Investor and Fund Manager: What has been Ophelia's biggest investing mistake? How did it change her mindset and approach? In a world where everyone does seed investing, why does Ophelia not? How was raising the first Blossom fund? What were some of her biggest lessons? Why does Ophelia believe that follow-on investing can damage returns? How does Ophelia reflect on her own relationship to price? When has she paid up and it worked? When has she paid up and it not worked? Does Ophelia think it is fair that many find her curt and abrasive to work with? 4.) Europe: Is Now Really The Right Time? What would Ophelia like to see change in the way European VCs act? If Ophelia could invest in one seed firm, one Series A firm and one growth firm in Europe, what would they be? Why? What are 1-2 of the biggest barriers Europe must overcome in the next 5 years?

Adam Grenier is an OG of the growth world. His first role in growth, was none other than Uber where he was Head of Growth Marketing and Innovation building the global marketing growth infrastructure and team from the ground up. He then enjoyed successful spells at Lambda School and Masterclass as VP Growth and VP of Marketing, respectively. If that was not enough, Adam is also a prolific angel having made investments in Superhuman, Table22, and FitXR to name a few. In Today's Episode with Adam Grenier We Discuss: 1.) Entry into the World of Growth with Uber: How did Adam make his way into the world of growth with Uber and Ed Baker? What are the single biggest takeaways from his time at Uber, Lambda and Masterclass? What does Adam know now that he wishes he had known when he started in growth? 2.) Growth: What it is? Why You Do Not Need a Team for it? How does Adam define the term "growth" today? What is the role of "Head of Growth"? Why does Adam believe that you do not need a growth team? How can leaders infuse growth principles, mindsets and metrics into existing teams? WHat are the single biggest mistakes founders make when thinking about growth? 3.) Hiring Growth Mindsets: How to Ask the Right Question: What are the clearest signs to Adam that someone has a growth mindset? What are the right questions to ask to see how they think? How does Adam use tests and case studies to determine the growth mindset of a person? What did Uber teach Adam about the best practices to hire for growth? 4.) Uber: Scaling a Monster and Spending $1BN on Ads: What are some of Adam's biggest lessons from spending $1BN on advertising at Uber? Why at anytime were there 200 people paying for ads with their personal credit cards? Why does Adam believe China was "the wild-west"? How did all of their competitors in China have Uber data? How do growth mechanics, channels and disciplines compare between US vs China?

Jackie Reses is the CEO of Lead Bank and previous Exec Chair of Square Financial Services and Head of Lending and Banking. One of only people to have started a bank as a de no; Only tech company to get approved for a de novo. Chair Economic Advisory Council of SF Federal Reserve. Kris Dickson is the CFO of Lead Bank and previously the CAO / CFO of post-BK Lehman Brothers parent co-estate for 10 years. Lehman Holdco estate has liquidated and distributed $129 billion to unsecured creditors through the end of 2022. In Today's Episode on SVB We Discuss: What Happened? How and why did SVB fail so fast? Was it the result of systemic problems or a series of management mistakes? What role did VCs play in the downfall of SVB? What role did social media and online banking play in the failing of SVB? What Now? What happens now? Will depositors have their deposits guaranteed? Will there be a buyer for SVB? Who is the most likely? Should founders be worried about moving their money to neo-banks? Should founders in any circumstances transfer money to their personal accounts? What is the best and worst outcome?

Amjad Masad is the Founder and CEO @ Replit, whose mission is to bring the next billion software creators online. With Replit, Amjad has raised over $100M from the likes of Peter Thiel, a16z, Coatue and Addition, to name a few. Before founding Replit, Amjad was a tech lead on the JavaScript infrastructure team at Facebook. Before Facebook, Amjad was #1 employee at Codecademy. In Today's Episode with Amjad Masad We Discuss: 1.) From Troublemaker Child in Iran to Silicon Valley Founder: How did Amjad make his way into the world of tech and Silicon Valley having grown up as a misbehaving child in Iran? In what ways did Amjad show early signs of exceptionalism? Why does he always look for this in people he is hiring for Replit? What does Amjad know now that he wishes he had known when he started Replit? 2.) The Future: A New World with AI at the Centre: Why does Amjad believe we will see thousands of billionaires created from the innovation in AI? Why does Amjad believe AI will lead to 100 more Elon Musks? If Amjad were CEO of Facebook, what would he do? Why and how do they have to invest in AI? Will TikTok be banned in the US? How will this be resolved? Why does Amjad believe that 300 people control the future of AI? Is that not concerning? 3.) The Future of Society, Employment and Wages: Why does Amjad believe in 10 years, 1 engineer will be able to do what 100 do today? What will happen to the real wages of engineers? How does Amjad see the inclusion of universal basic income in the future? Is Amjad concerned about societal and civil unrest with wealth disparity widening further? 4.) Building the Replit Army: Why does Amjad believe that so many in tech have gotten too soft in the last few years? Why does Amjad release a "Why You Should Not Join Replit" page and share it with all candidates? How can a founder know if they have good company values or not? Why does Amjad feel we need a spiritual reform in company building? Why are startups and religion the same?

Glen Coates is the VP of Product @ Shopify, leading the development of Shopify's core commerce platform. He also oversees the core developer platform and Shopify's partner ecosystem, which includes over 10,000 publicly available apps in the Shopify App Store. Originally a CompSci grad, Glen moved from Sydney to San Diego in 2008 to run US distribution and e-commerce for an Australian eco-products company. In 2010, he attended Columbia Business School for one whole day before quitting to start Handshake, a SaaS B2B e-commerce platform. Glen joined Shopify in May 2019 when the company acquired Handshake. Glen has been in the Vice President role since October 2020. In Today's Episode with Glen Coates We Discuss: 1. From Game Developer in Sydney to Running E-Commerce Warehouse in NYC: How Glen made his way into the world of product and e-commerce having started life as a game developer? Why does Glen believe that the best founders and product people often have their roots in gaming? What does Glen know now that he wishes he had known when he joined Shopify? 2. The Art of Product and Product Management: Is product more an art or a science? If you had to put a number on it, what would it be? What is "product management"? Why can it not be reduced to frameworks? What are "product principles"? How do Shopify use them? How should product teams set them? What makes the very best PMs today? What are the commonalities in them? What is the sign of a poor PM? What would Glen most like to change about the world of PMs? 3. The Art of Product Marketing: What does Glen believe is the true art of product marketing? How did a CEO group teach Glen how to tell truly great stories? How can one tell great stories when you have to cater to multiple different customers/personas? How does Glen evaluate the current state of Shopify's product marketing? 4. Shopify and The Future of Shopify: Why does Glen think it is important for Shopify to have a tops down decision-making process for product strategy? What does Glen believe is the #1 reason why Shopify is such a large and successful company? What is the single hardest element of Glen's role today? How does Glen believe that Shopify will be larger than Amazon in 5-10 years time?

Alex Schultz is the Chief Marketing Officer and VP of Analytics for Meta (formerly Facebook), leading Marketing, Analytics, and Internationalization. Previously, Mark Zuckerberg stood up and said, "Facebook would not be a BN user company without Alex". At Meta, Alex has pioneered the integration of product and direct response marketing at Meta and helped launch many of the company's most impactful products and initiatives. Alex is gay and is the executive sponsor of Facebook's LGBTQ+ Employee Resource Group. In Today's Episode with Alex Schultz We Discuss: 1. From Paper Planes to CMO of Facebook: How Alex started his career in the world of paper planes and how that led to his getting a role at an early eBay? What are 1-2 of his biggest lessons from eBay? How did the role at Facebook come about in 2008? Why did he decide to join the early Facebook? What does Alex know now that he wishes he had known when he started his time at Facebook? 2. The Secret to Scaling to 1 Billion Users: Mark Zuckerberg has said that "Facebook would not be a billion-user company without Alex". So what does Alex believe are the 1-2 biggest needle movers in FB scaling to 1 billion users? Why does Alex believe that the best leaders are patiently right? How can management be direct and effective but also show they care and be kind? What have been some of Alex's biggest lessons on people management across different phases of the company? 3. Crucible Moments in Facebook History: Facebook Messenger Split: What was the decision-making process behind splitting Messenger from the core Facebook App? What did they do right and well in the split? What mistakes were made? Rebrand to Meta: Why did Facebook decide it was right to rebrand to Meta? Has the rebrand gone well? How does Alex define success with the rebrand? Reels vs TikTok vs SNAP: Does Alex believe we are moving away from the social graph and moving to content discovery only? How does Alex feel Reels is doing in the race against TikTok? What have they done well? Why does Alex believe SNAP hasn't innovated in the way people think and copied Kakao in cases? What is the key to turning Reels into a monetization machine for Facebook? 4. Alex Schultz: The Person and Leader: How was the coming out process for Alex in the tech community? How did his parents respond to the news? What does Alex mean when he says, "everyone has to mourn their own version of your future self"? Why when he moved to the states was Alex advised to go back in the closet? Does Alex feel we have a long way to go in equalizing the playing field both for homosexuality and trans-gender participation?

Hunter Somerville is a Partner @ Stepstone, one of the largest secondary buyers, fund investors and players in our ecosystem with over $600BN in capital responsibility and over $100BN AUM. Additionally, Hunter serves on the LP Advisory Boards for Felix Capital, Foundry Group, Imaginary Ventures, Scale Venture Partners, Boldstart Ventures, Ludlow Ventures, and more. Prior to StepStone, Hunter was a general partner with Greenspring Associates, a venture capital and growth equity investment firm that merged with StepStone in 2021. Before that, he worked as an associate for Camden Private Capital. In Todays Episode with Hunter Somerville We Discuss: 1. Three Types of Secondaries: What are the three different types of secondaries? What is the current situation with company secondary opportunities today? What is the current landscape for fund secondary opportunities today? What are GP-led restructuring or strip sales? How do they work? 2. LPs Today and Moving Forward Investing in Funds: Will we see a wave of LPs not commit to their existing managers? What is the denominator effect and how does that impact LP deployment into funds? What are the top 3 reasons why LPs will not re-commit to existing managers? Do LPs feel VCs have fairly marked down their venture books in the last 6 months? Does Hunter agree that if you have not returned cash to your LPs when you could have done ijn the last 5 years, then you are most in trouble? Why does Hunter believe we will see more international LPs entering venture than ever before? 3. Liquidity: When Does the Cash Hit: Why was liquidity so bad in 2022? How did that compare to 2021? How does Hunter forecast liquidity environments in 2023? What could drive them? How active were Stepstone in secondary buying over the last few years? Is now the time to be greedy when others are fearful in secondaries? What discount was Hunter seeing both on fund and company side secondaries in 20-22? What is the current level of discount being applied to both company and fund secondaries? 4. AMA with One of the Largest Secondary Buyers: Which LP class will be hurt the most from the last fund cycle? What would Hunter most like to change about the world of venture? What was Hunter's biggest mistake on a company investment? What are the biggest mistakes LPs make when they do direct investing? Why are big-name people entering firms as GPs not always a good sign?

Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world's first Wi-Fi video doorbell while working in his garage in 2011. Since Ring's launch in 2013, Ring has helped make thousands of neighborhoods safer all around the world. As part of the journey, Jamie raised over $385M from the likes of True Ventures, Felicis, First Round, CRV, Upfront and more. In 2018, Amazon acquired Ring for a reported $1BN. Prior to Ring, Jamie founded several successful ventures including PhoneTag, the world's first voicemail-to-text company, and Unsubscribe.com, a service that helped email users clean commercial email from their inboxes. He successfully sold both companies in 2009 and 2011 respectively. In Today's Episode with Jamie Siminoff We Discuss: 1.) From Creating the First Wi-Fi Doorbell to $BN Acquisition: When was the moment Jamie realized he had to create the world's first Wi-Fi-enabled doorbell? How di Richard Branson come to be an investor in Ring? What was the process? How does Jamie advise other founders when it comes to the question of whether it is valuable having business moguls as investors in their business? 2.) Crucible Moments: From Lawsuits and Near-Death to $22M in Sales in a Day: When Jamie hears the words "near-death experience" what is the moment in the Ring journey that comes to mind? How did Jamie get through a crippling lawsuit and come out selling $22M in 24 hours on QVC? How did Jamie feel when he placed a $500M order with manufacturers when he only had $100M? What does Jamie believe was the hardest phase of the business? 3.) Jamie Siminoff: The Leader: Why does Jamie want to hire marathon runners? Why does the analogy make for good hires? Does Jamie start from a position of trust with new hires and it is there to be built or start with no trust and it is there to be gained? Does Jamie believe he is a tolerant leader? What does he mean when he says, "I want to see the dirt under your fingernails"? Why does Jamie believe that building a brand is like making great wine? Why does Jamie really hate customer surveys? What should be done instead? 4.) Selling for $1BN to Amazon: How did the Amazon acquisition come to be? How did the discussion go? Why did Jamie decide then was the right time? When you sell for a $1BN, does the cash hit your account soon? When did Jamie actually receive the money? How did he feel when he saw it is in his account? What does Jamie believe Ring did so well to make the acquisition a success? What did Amazon do well to ensure Ring was integrated most effectively? What are 1-2 of the biggest lessons Jamie has learned from being within Amazon?

David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry's, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David is also the Chairman of GoodDog, a marketplace to find pets online. In Today's Episode with David Tisch We Discuss: 1.) From Techstars To Founding BoxGroup: How did David start his own firm in the form of Box having started at Techstars? What advice from Brad Feld does David always remember and hold close? What does David know now that he wishes he had known when started investing? 2.) The Debate: The Math Does Not Work: Portfolio Construction: Ownership Does not Matter: How does David justify writing $100K checks from a $127.5M early-stage fund? Even if it is a home run, it does not make a difference to the fund? Level of Diversification: If David is writing small checks like this, with his fund size he will have hundreds of companies, what does David believe is the right level of diversification? Reserves management: How does David think about the ratio of initial to reserves when deploying the funds today? How does reserves management change in a recession? How does David prevent other VCs from using this to try and push him down to always writing a $100K check? Why does David believe that the size of check he is able to invest is the VC's problem and not the founders? Price Sensitivity: How does David assess his own relationship to price today? Why does he believe that company valuation is not something that the investor controls? 3.) Advice to Founders Raising Rounds: What does David believe is the #1 role of the CEO? What are the three most important variables for founders to focus on when raising their round? How should founders analyze the tradeoff between the brand of the VC and the size of the round? Does signaling really make a difference when a large fund invests at seed? How did multi-stage funds change the seed landscape forever with a new product? Who does David believe are the tourists in early-stage venture? Will they leave in the recession? 4.) David Tisch: AMA: Why does David believe that consumer social is not fun anymore? Who when they send him a deal does David take it most seriously? How does David want to ensure that bad VC behaviour is exposed? What would David most like to change about the venture landscape today?

Joey Levin is the CEO of IAC where he has overseen the constant evolution of the company, including the initial IPO and subsequent spin-off of Match Group, the spin-off of Vimeo, and the acquisitions of Angie's List and Care.com. If that was not enough, in October 2022, Joey was also appointed as CEO of Angi Inc. In addition to this, Joey also serves on the boards of IAC, Turo, and MGM Resorts International. In Today's Discussion with Joey Levin We Discuss: 1.) The Makings of a Great Leader: When Joey was younger, what did he want to be when he grew up? What is Joey's biggest advice to people coming out of college/university at this time? What 1-2 things does Joey credit his internal and fast rise in IAC to? 2) Value Investing is BS & The Markets Today: Why does Joey believe the idea of "value investing" is BS? What 1-2 behavior traits of investors in the last few years were most dangerous? Why does Joey believe that the current market is reasonable and now is the new normal? How does Joey keep internal morale high when people have become accustomed to high stock prices? Does Joey believe in the statement, "be greedy when others are fearful and fearful when others are greedy"? 3.) Simplification is the Secret to Margin & Messaging 101: Why does Joey believe simplification is the core of high margins? How can startups and scale-ups identify where to simplify first? What are the subsequent steps? Why does Joey believe that the best values should make you feel uncomfortable? What is a lesson from Joey's father on what makes truly great messaging? 4.) Parenting, Money and Marriage: How does Joey reflect on his own relationship to money today? What are 1-2 lessons taught by his mother on how to approach money and wealth? What does Joey believe is the secret to truly happy marriages? What are Joey's biggest lessons on what it takes to be an effective and good father?

Kevin Systrom and Mike Krieger are the co-founders of Instagram. Since its release in 2010, Instagram has become of the most significant products in modern society shaping the way millions of people engage with the world around them. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized news feed driven by artificial intelligence. In Today's Show with Kevin Systrom and Mike Krieger We Discuss: 1.) The Perfect Partnership: Question from Josh Kushner @ Thrive: What makes Kevin and Mike such a great partnership? What was the last disagreement they had? How was it resolved? They built Instagram in person, in an office. They are building Artifact remotely, what has changed in the way they operate when comparing remote to in-person? 2.) Why Social Networks are Broken & The Next Frontier: Why does Kevin believe social networks today are broken and should be less social? What fundamental premise are social networks built on that Kevin believes is wrong? How will AI and machine learning be central in the next wave of social? How do Kevin and Mike evaluate TikTok and the next wave of content discovery? 3.) Welcome Artifact: The Comeback: Why does Kevin believe they chose the worst idea for their new company? Why is it? Were they nervous about founding Artifact and expectations being so high given Instagram? Why does Kevin argue that Artifact is not actually a "news app"? What does Kevin believe is the biggest lesson Apple taught us about messaging? 4.) Family, Money, San Francisco: Why does Kevin believe that SF will return as the centre of tech once again? Why does Kevin believe that many millennials in the workforce today are entitled and soft? How has becoming a father changed the way Kevin and Mike operate and execute? How do Kevin and Mike assess their relationship with money today? How has it changed? 5.) Hiring, Investing, Managing: What are some of Kevin and Mike's biggest lessons when it comes to hiring? What are the single biggest hiring mistakes they have made? Is it wrong to not hire someone because they are really really boring? What are the biggest lessons for Kevin and Mike from their angel investing?

Zach Lawryk is Head of Solutions Consulting @ Rippling, what is solutions consulting? They are the product expert in the solution that ties a business value to help support the sales rep in the execution of their quota. And there is no one better than Zach, prior to leading the solutions consulting team at Rippling, Zach was VP of Solutions Consulting at Slack where he scaled the SE team from 10 to 200. Before Slack, Zach was Head of Solutions Engineering @ Optimizely and before that was Director of Sales Engineering at Box. In Today's Episode with Zach Lawryk We Discuss: 1. ) WTF is Solutions Engineering: What is Solutions engineering and why is it important? How does a software developer turned lawyer become one of the OGs of Solutions Engineering? What is the single biggest piece of advice Zach gives to graduates entering the workforce today? 2.) When and Who: Building the Foundations: When is the right time to hire your first solutions engineer? Should this be a senior hire or a more junior hire? What experience is ideal? Would Zach rather have someone who has sold to the same customer segment or sold to the same deal size? What are the challenges with each? 3.) Making the First Hire: The Process: What is the right hiring process for solutions engineers? Which members of your existing team should be involved in the process? What are some of Zach's favourite questions on the candidates past to determine quality? What are the best case studies and tests to give potential hires to test their aptitude? What are the biggest red flags in the hiring process for solutions engineers? 4.) Integrating into the Team: Making it Work: What is the optimal onboarding process for solutions engineers? Why does Zach think it is important they spend time with customer success in their first month? What is the right way to measure the effectiveness of SE's? How should the entrance of SE's impact the close rate and comp structure for AE's? How can sales leaders prevent division and friction between AEs and SEs?

Aloe Blacc is a GRAMMY nominee and the voice behind such hits as Wake Me Up, The Man, SOS, I Need A Dollar, and many more. Aloe has toured the world, won countless awards but his latest album, All Love Everything, is the singer-songwriter's first collection of material written as a father. "Becoming a father made me want to share those experiences in music," he says, admitting it's a challenge to translate such a powerful thing into lyrics and melody. If that was not enough, Aloe is also an entrepreneur with the founding of his new company, something we discuss in the show today. In Today's Discussion with Aloe Blacc: 1.) Entry into Music and Running From Fame: How Aloe first fell in love with music and made his foray into the world of music from Ernst & Young? Why does Aloe believe he is running from fame? What does it bring that he does not like? What does Aloe believe he is running towards? How has this changed? 2.) The Art of Storytelling: How does Aloe think about what it takes to be truly great at storytelling? What is the difference between a great vs an average story? How has his style of storytelling changed over time? What are the biggest mistakes that people make in storytelling? 3.) The Songwriting Process 101: What is Aloe's process for writing new songs? How does he take an idea and expand it, test it and execute against it? How did "Wake Me Up" with Avicci come about? What was the creation process there? What was it like working with Avicci? What did Aloe learn from him about being liked? 4.) Marriage, Fatherhood, and Global Stardom: What does Aloe believe is the key to truly successful marriages? How does Aloe retain a sense of romance with intense work pressures? How has becoming a father changed the way in which Aloe thinks and operates? What is Aloe's love language? How has doing this with his wife changed their relationship?

Mike Duboe is a Partner @ Greylock where he sits on the board of Builder, Inventa, Novi, Pepper, Postscript. Prior to entering the world of venture, Mike was the first in-house growth hire at Stitch Fix, where he built and led the Growth organization helping take the company through to their IPO. Before Stitchfix, Mike was the first growth hire at Tilt, where he built and oversaw multiple teams, including analytics, marketing, community, and growth product. He also served on YC's growth advisory council and was a growth lecturer at Reforge. In Today's Episode with Mike Duboe We Discuss: 1.) Entry into the World of Growth: How Mike made his way from consulting at Bain to leading the growth team for Stitchfix? What did Mike believe about growth 5 years ago that he no longer believes? What does Mike know now that he wishes he had known when he entered the world of growth? 2.) When and Who To Hire: How does Mike define the term "growth team"? What is their core role and responsibility? Should the first growth hire be a senior growth lead or a more junior analytical lead? What data foundations should founders have in place prior to their growth hire joining? What are the most common ways founders fail to prepare for their first growth hires joining? When does Mike believe is the right and crucial time for growth hires to be made? Should these growth hires join existing teams or be put in standalone "growth teams"? 3.) The Hiring Process: How to Detect and Win the Best: How should founders structure the interview process for their first growth hires? What are the best questions to ask to reveal the quality of a potential growth hire? What are the right case studies and tests to do to assertain their quality? What are the different levels of comp package for different growth execs? What are the single biggest mistakes founders make in the hiring process? 4.) Mastering Paid Marketing: Lessons from Stitchfix: Why is CAC/LTV a BS metric? What should be used instead? When is the right time to start really engaging with paid marketing? How should marketing and growth teams determine budget on a per channel basis? How much is the right mix between paid vs organic? What are Mike's biggest lessons from making paid work so well at Stitchfix? What are the single biggest mistakes Mike sees founders make today with paid marketing?

Tom Loverro is a Partner @ IVP where he has led or was actively involved in investments in Amplitude, Coinbase, Hashicorp and Datadog to name a few. As a result of his investing success, Tom was named to Forbes Midas List in 2021. Prior to joining IVP, Tom was a Principal at RRE Ventures. In Today's Episode with Tom Loverro We Discuss: 1.) The Entry into Venture: How did Tom make his way into venture first with RRE? How did the role with IVP come about? Does Tom believe we will see many venture investors move firms with much of their existing expected carry cut in half with the changing landscape? What is Tom's biggest advice to someone looking to make their way into the venture world? 2.) The Calm Before the Storm: Why does Tom believe now is the calm before the storm? Why does Tom urge founders to go out and raise now before the storm hits? Is Tom already seeing pricing coming down for both early and late-stage companies? 3.) When The Storm Hits: When does Tom believe the storm will hit? Why does Tom believe when it does hit, it will be worse than The Great Financial Crisis? How will VCs respond when the storm hits? How will it impact their investing cadence? How will LPs respond when the storm hits? Will they cut back their manager commitments? Does Tom have hope that their will be a new class of LPs in this new economic cycle? 4.) The Rounds That Happen When The Storm Hits: Does Tom believe we will see a wave of down rounds when the storm hits? Why are they less common than people think? In the eye of the storm, will we see further layoffs? Will we see firesales? Will we see a tidal wave of shutdowns? Will large multi-stage funds with huge amounts of dry powder change their deployment pace? The Survival Guide for the Storm: 1.) Raise Now: Why does Tom believe that startups should raise now, not later? What amount of runway should they raise for in this environment? 2.) Cut, Cut and Cut Some More: What amount of runway should startups be cutting to get to? How will this impact marketing spend? Why are your marketing dollars more powerful now than ever before? 3.) Focus on Survival Not Valuation: What does Tom mean by this? How can founders gain leverage with VCs when raising today? How can founders instil a sense of urgency in their raise with investors? 4.) Bring on Operators with Experience: Why would operators with experience join a struggling startup? Will operators with experience not have a flight to safety and stay at their well-paid FANNG role? Does this potential operator not shorten runway even further as they are often expensive? 5.) Unit Economics over Growth: How can founders show investors a superior profile of unit economics moving forward? Do investors not want both unit econ and growth today? 6.) Play Your Cards Right and Then Go on Offense: How does Tom advise founders on the right time to go on offense? 7.) Be Decisive, Half Measures Rarely Succeed: How does Tom define a half-measure? What is so wrong with half-measures?

Steve Pagliuca is a Senior Advisor at Bain Capital, the firm he joined in 1982 and as a Managing Director of Bain Capital, he has helped build the firm into one of the world's leading investment companies with over $160 billion in assets under management. Steve is also a Managing Partner and Co-Owner of the World Championship Boston Celtics Basketball franchise. Steve is also co-owner and co-chairman of the Serie A professional football club, Atalanta Bergamasca Calcio. If that was not enough, Steve currently, serves on the Board of Directors of Burger King, Gartner Group, HCA, Warner Chilcott, and FCI. Huge thanks to Moshe @ Shrug Capital for making the intro. In Today's Episode with Steve Pagliuca We Discuss: 1.) From Duffel Bags at Duke to Buying Sports Teams: How Steve went from having a single duffel bag arriving at Duke University to entering the world of private equity with the founding of Bain's PE funds? Did Steve always know he would be successful? What does Steve think about the importance between luck and timing? How did Steve's mother impact how he approaches parenting and self-belief with his children? 2.) Buying Sports Teams: Not So Different to Companies: When buying and running a sports team, what is the same, and what is different from buying and running a company? What is Steve's biggest advice to new owners of sports teams? What are the single biggest mistakes sports team owners make when they buy a team? What happened with the Chelsea bid? Why did Steve lose? How did debt change the deal? 3.) The Future of Sports Ownership: Why does Steve believe we have seen a massive rise in American and private equity buyers of both global sports teams but also European sports teams? How has "new media" changed the inherent value that can be placed on a team? Why does it change the value? Which forms of "new media" are most important? How much further can the value of these sports teams increase? Does this massive increase in the price and assets of certain clubs not lead to a massive inequality in sports? What can be done to prevent this imbalance? 4.) Steve Pagliuca: The Person and Capital Allocator: What is the single best investment advice Steve has ever received? How does Steve think about his relationship to wealth today? How has it changed over time? What does it take to have an amazing marriage and be at the top of your profession? What were 1-2 elements that made Bain able to scale to the proportions of AUM that they have done? What would he have done differently?

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Ariel has raised over $2BN for Navan from some of the best including a16z, Zeev Ventures, Lightspeed, Greenoaks, and Elad Gil. Prior to TripActions, Ariel co-founded streamOnce, a business multimedia integration platform that was successfully acquired by Jive Software, where Ariel had previously served in a senior position following his time at Hewlett-Packard. In Today's Episode with Ariel Cohen We Discuss: 1.) Why Education is Outdated and Wisdom to People Entering the Working World: Why did Ariel not really attend many classes when he was a student? What would be his biggest advice to young people leaving school today? Where would he focus? Why does Ariel believe that traditional education is more outdated now than ever before? 2.) Why SAP and Salesforce Will Die: Why does Ariel believe that SAP and Salesforce have not innovated for a decade? Why does Ariel believe that Slack is a disaster inside of Salesforce? What are the single biggest advantages that startups have over these large incumbents? What can startups do to retain innovation and speed as they scale into becoming an incumbent? Why are the best founders willing to kill their own projects? 3.) Growing a Business 3x and Raising at a $9.2BN Valuation in COVID: How did Ariel grow the business 3x with all travel being banned? What were the tactics to blitz scaling during COVID? How did Ariel approach his investors for a new round in the middle of COVID? How did he get such a high price in the midst of a global pandemic? What is the bull case for how Navan can be a $40BN company? 4.) Margins Matter: Gaining Leverage Through Additional Margin: With Navan's 80% margin, they have 30% higher margins than other competitors, how do they have such high margins? With the additional 30%, how does Ariel plan to scale Navan's reach and use the margin to do so? How does OpenAI play a role in helping Navan increase its margin even further?

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo's early entry into software buyouts and built the firm into one of the top private equity firms in the world. Today, Orlando directs the firm's strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street's best dealmaker" in 2019, and he was dubbed "Private equity's king of SaaS" by the Financial Times in 2021. In Today's Episode with Orlando Bravo We Discuss: 1.) From Puerto Rico Roots to Wall Street's Best Dealmaker: How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him? Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors? What does Orlando know now that he wishes he had known when he started his career? Why does Orlando disagree with setting timelines in life? Why does it not help? 2.) The Secret to Success in Value Investing: What is good value investing today? What is it not? What three things does Orlando look for when doing a deal and acquiring a company? Why is every company in the world worth its future cash flows? How important is price today? How does Orlando reflect on his own price sensitivity? Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022? 3.) WTF is Happening In Markets Today: How does Orlando reflect on where the market is today? Is this the new normal? How does Orlando expect the market to change over the next 12 months? Why does Orlando believe that the best companies win in the worst times? Is this the result of quantitative easing on behalf of central banks? Who is to blame? How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife? 4.) Orlando Bravo: The Leader, Father and Husband: What is Orlando's biggest fear in investing? How has this changed over time? How does Orlando reflect on his own relationship to money today? How has that changed? What are Orlando's biggest parenting lessons from his mother? Why does Orlando believe that for most people, their late twenties are their toughest? How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up? How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage? Items Mentioned in Today's Episode: Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70-person product and design org. Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe's Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, EBITDA positive since Sept 2022, 85%+ gross margins, and over $5BN paid out to 250,000 people. Alex has raised over $679M with Deel, pricing the company at the last round at $12.1BN. Investors in the company include a16z, Spark Capital, Coatue, and many more. In Today's Episode with Alex Bouaziz We Discuss: 1.) From Student in London to Decacorn Founder: How Alex made his way into the world of startups and how he came up with the idea for Deel? Did Alex always know he would be successful when he was growing up? What does Alex know now that he wishes he had known when he was starting? 2.) The Importance of Execution: How important does Alex think speed of execution is for startups? What can startups do to deliberately increase their speed of execution? How does Alex think about the dilemma of losing quality with speed? What does Alex think you do need to go slow on to ensure it is perfect? How does Alex think about focus and prioritisation today with Deel? 3.) Scaling to $295M in ARR in 3 Years: When did Alex know he had true product-market fit with Deel? How did Alex use a 50-person Whatsapp group to both determine product market fit and to navigate product direction for the company? What was the key to Deel's blitz scaling strategy? What worked? What did not work? How did Alex hire 2,000 people in such a short space of time? What broke first in the organisation? How could they have prevented it? 4.) Secondaries, Angel Investing and Wealth Management: How much did Alex take out in secondaries in the last round of funding? How did Alex determine how much cash to allocate to angel investing? Why does Alex believe most founders make poor angel investments when they have cash? What have been Alex's biggest lessons from investing? How has it changed how he operates? Why should all founders be super transparent in investor updates?

Hunter Walk and Satya Patel are Co-Founders and Partners @ Homebrew, one of the leading seed funds of the last decade. Following 10 years of stellar returns with investments in the likes of Chime, Plaid, Gusto and many others, they decided to not accept any further LP capital and to only invest their own money moving forward through Homebrew Forever. In Today's Discussion on Homebrew We Breakdown: 1. ) The Foundings of a Great Partnership: What was the moment when Hunter and Satya decided they were going to go out and raise their first fund with Homebrew I? What are the core principles that all founding partners need to align on before they start a firm together? What questions should they ask of each other? Why does being independently wealthy coming into a partnership make the partnership easier and more efficient to operate? What changes when the partners have money already? 2.) What Changes When Moving From LP Dollars to Personal Capital: Why did Hunter and Satya decide to not raise any further capital from external LPs? Asset allocation-wise, how did they determine how much is the right amount to set aside for the first 2 years of investing? How many investments do they want to make with that cash? How does investing their personal capital change their deployment pace and cadence? How does it change their approach to reserves management and follow-on financing? How does it change their approach to pricing? How price sensitive are they today? 3.) Analyzing the Seed Landscape Today: Why do Hunter and Satya not think that a $100M seed fund is enough to properly execute a world-class seed strategy today? Who is their competition with the new strategy? How does it change their relationship with large multi-stage funds? How does it change their relationship with seed funds? Do they agree that the last generation of sub $20M micro-funds will not raise another fund in this cycle? How did their entrance impact the seed landscape over the last few years? Why are LPs also to blame for many of the original seed managers raising larger and larger funds? 4.) Companies: Money and People are The Problem: Why has too much money been such a problem for many Homebrew portfolio companies over the last few years? How has too much money changed their execution plans? What happens to the "living dead" companies with many years of runway but no product market fit? Who does this market cater to well? Who will thrive in this market? What have people forgotten about both startups and venture in the last 2 years that we have to remember? Why is this generation so entitled and expectant? Why are startups not a get-rich-quick scheme?

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 million monthly users, 2,000 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN. In Today's Episode with Cliff Obrecht 1.) From Teacher to Billionaire Tech Founder: How did Keith make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva? How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no's? What are Cliff's biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs? 2.) Scaling to $40BN: The Biggest Lessons: What does Cliff mean when he says the secret to successful hiring is looking for "distance traveled"? How does he determine this in the interview process? What have been some of the single biggest lessons in what it takes to acquire the best talent? What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result? What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same? 3.) The Art of Deal-Making: How does Cliff think through what makes a "good deal"? How does he approach negotiation? What are the biggest mistakes founders make when negotiating and doing deals? What have been Cliff's biggest lessons on successful investor relations over the years? How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way? 4.) Cliff Obrecht: Money, Fatherhood and Marriage: How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time? Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively? Why would Cliff hate for his children to be brought up in excess wealth? What does "great fatherhood" mean to Cliff? What are the most challenging aspects of parenting? What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?

Stevie Case is the CRO @ Vanta where she oversees Vanta's go-to-market team to support the company's rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, Stevie helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio's enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue. If that was not enough, Stevie is also a Founding Operator @ Coalition Network and a prominent angel investor. In Today's Episode with Stevie Case We Discuss: 1. ) From World's First Pro Female Gamer to CRO: How did Stevie make her way from pro gamer to CRO? How did her career in gaming make her a better CRO and sales leader? In her early sales career, how did being a single mother with a child impact her approach to sales? What can founders do to make workplaces more inclusive for parents today? 2.) Enterprise or PLG: Which One To Choose: Why does Stevie believe it is not right to do both PLG and enterprise at the same time for startups? How can startups and sales teams move into enterprise selling gradually through testing and without committing a significant budget to an enterprise sales team? How do founders know when is the right time to move from PLG to enterprise? What are the signs? 3.) The Mythical Sales Playbook: How does Stevie define the term "sales playbook" today? What is it not? Should the founder be the person to create the sales playbook? If not them, then who? When is the right time to make your first sales hire? When is the wrong time? 4.) Mastering the Hiring Process in Sales Recruits: How should we structure the interview process for new sales reps? What is the right profile for these first sales hires? How do the best sales talent answer questions and perform in interview processes? How can we really test for grit and curiosity in the interview process? What are the single biggest mistakes founders make when hiring for sales? 5.) Discovery, Discounting, Deal Velocity: With sales cycles being so long, how do you know if enterprise sales reps are good? What is the difference between good discovery vs bad discovery? Should founders engage in discounting to get deals over the line? When does it work?

Albert Wenger is a managing partner at Union Square Ventures, one of the most successful venture firms of the last decade with a portfolio including Coinbase, Twitter, Twilio, Etsy, and many more. Before joining USV, Albert was the president of del.icio.us through the company's sale to Yahoo and an angel investor (Etsy, Tumblr). He previously founded or co-founded several companies, including a management consulting firm and an early-hosted data analytics company. In Today's Episode with Albert Wenger We Discuss: 1.) From Failed Startup Founder to Leading VC: How Albert transitioned from being a failed entrepreneur to being one of the most respected venture investors with USV today? What were the clear signs for Albert that he was not a good entrepreneur? Why does Albert believe this downturn is different compared to the dot-com bubble? Why was there more hope and promise coming out of the dot-com bubble? 2.) Income Inequality, The Rise of Depression & The Role of Politics: Why is income and wealth inequality more concerning than ever? Why does Albert believe universal basic income is the right solution? Why is mental health worse than ever? What can be done to improve this? Why are our politicians failing us? What should our politicians be doing? How does the rise of Trump show us what society is looking for in politicians? 3.) Climate Change: Misnomers, Developing Countries, Civil Disobedience: What are the single biggest misnomers people have when it comes to climate change? How can we shift spending on climate change solutions from 5% of GDP to 50%? Is that possible? Why do developing nations have an advantage when implementing climate change solutions over more developed economies? Why is civil disobedience the right course of action to ensure society is on a path to change our approach to climate change? 4.) Crypto and Central Banks: The Future of Finance: Why does Albert believe that over the past few years, for many, crypto was a good hedge against inflation? How damaging does Albert believe SBF and FTX will be to crypto in the long term? How does Albert evaluate the potential for governments to create a "central bank digital currency"? What would Albert like to see in a potential currency like this? How could stable coins be the solution to this? What is Albert fearful of with central bank digital currencies? Why does Albert believe now is the best time to be investing in crypto? 5.) The Future of Social Media: Twitter & TikTok: What does Albert believe is wrong with Twitter today? Why was the blue check mark such a mess? What does Albert believe Elon should do with Twitter from this point on? How should Elon deal with the debt providers he has? What happens to Twitter moving forward? Why is it so hard to kill? What is the future of TikTok? Will it be banned in the US? How concerned should the consumer be concerning their data being shared with the Chinese Government?

Mike Cessario is the Founder and CEO @ Liquid Death, the man hacking the healthy beverage market with the first hilarious water brand. It is working, Liquid Death's latest valuation was over a staggering $700M and Mike has raised over $200M since founding the company from the likes of Science Inc. Away's Jen Rubio, Dollar Shave Club's Michael Dubin, Swedish House Mafia and Tony Hawk to name a few. Prior to founding Liquid Death, Mike was in the advertising industry at a number of dirrect firms including VaynerMedia. In Today's Episode with Mike Cessario We Discuss: 1.) From Canned Water to $700M Business: How did rockstars' hydration problems lead to the founding of Liquid Death? How did growing up with guns and heroine needles around him at school, impact how Mike sees the world today? What is he running from? What is he running towards? Everyone said, "canned water, that is a stupid idea". What does Mike tell to all entrepreneurs who are told their idea is stupid? How does Mike advise on picking your idea? 2.) How to Build a Truly Great Brand: What does the term "brand" mean to Mike? What does he mean when he says, "truly great brand transcends functional value"? What are the single biggest mistakes Mike sees founders make today on branding? Why does Mike believe people will always hate your brand, if it is good? What are the biggest brand mistakes Mike has made with Liquid Death? What brand does Mike most respect and admire? Why that brand? 3.) Marketing: The Secret to Reaching Millions of People with Little Budget: How does the Liquid Death team come up with the ideas they have for content? Why does Mike believe the label "storytelling" is kinda BS? Why does Mike believe people will always hate your marketing? What was Mike's biggest lesson from their Superbowl commercial with kids drinking Liquid Death, looking like beer? How does Mike decide which channel to prioritise? How has the rise of TikTok and short form video changed their approach to content? How does Mike approach resource allocation for new pieces of content? Do they spend big on few bits of content or spend little on many and see what works?

Hila Qu is one of the leading growth execs of the last decade. Hila helped scale Acorns from 1 million to 5 million users as their VP of growth. Hila then joined GitLab, where she launched their PLG motion (on top of an established sales motion), and built their first-ever growth team. Today Hila is an advisor to amazing companies like Replit and funds like Mucker Capital, Openview and First Round Capital. In Today's Episode with Hila Qu We Discuss: 1.) From Biology and Explosions to Growth: How Hila made her way into the world of growth with growthhackers.com? What are 1-2 of the biggest takeaways from her time with Acorns and Gitlab? How do B2B growth orgs compare to B2C growth orgs? What is different? What is the same? 2.) WTF is Growth? When? How & Why: How does Hila define growth today? What is it not? When is the right time for early-stage founders to hire their first growth hire? Why does Hila always look for data analysts in this first growth hire? From a data standpoint, what should founders have ready and accessible for their first growth hire to have access to and learn from? Is Google Analytics enough? 3.) Hiring Your First Growth Hire: How should early-stage founders structure the hiring process for the first growth hire? What do the best growth job descriptions include? What do they not include? Once applications are in, how does Hila advise founders screen for the best candidates? How should founders structure the interview process post-screening? What are the must-ask questions? Who is involved in the interview process? What are some red flags? 4.) The Master of Onboarding: What should new growth hires want to achieve in the first week? What should they want to complete in the first month? In the first quarter, what do the best candidates have completed? What can founders do to set their growth hires up for success in the best way at this time? 5.) Growth Models, North Stars, Activation and Onboarding and Key KPIs: What really is a growth model? How do founders and growth teams create one? How does Hila advise founders on how to pick the right North Star Metric to focus on? Why are activation and conversion Hila's two favorite growth metrics? What are growth loops? What are growth funnels? How do they work together?

Jeff Jordan is a General Partner @ a16z where he serves on the boards of Airbnb, Incredible Health, Instacart, Lookout, and Pinterest, just to name a few. Before a16z, Jeff was CEO OpenTable, where he led the company during a period of hyper-growth and oversaw its IPO. Prior to OpenTable, Jeff was Senior VP and General Manager of eBay North America where he oversaw eBay's early growth into one of the Internet's leading commerce brands. In this role, he drove the successful acquisitions of PayPal and Half.com and went on to become President of PayPal, where he was responsible for establishing the company as the global standard for online payments. In Today's Episode with Jeff Jordan We Discuss: 1.) From Taking Opentable Public to Being a GP @ a16z: What led to Jeff making the jump from CEO @ Opentable to becoming a GP at a16z? How does Jeff believe his operating career impacted how he thinks and acts as an investor today, both positively and negatively? What is his 1 biggest learning from eBay and then Opentable that has really shaped his mindset today as an investor? How did those experiences impact what he looks for in companies? 2.) The Two Core Features To Look For in Marketplaces: Fragmentation of supply side: Why does Jeff look for fragmented supply sides? Does this not take longer and is more expensive? How fragmented is fragmented enough? What are the most common reasons founders fail to acquire a fragmented supply side? Intelligent Lead Generation: What does Jeff really want to see in the way that new marketplaces acquire their customers? How does this change with the rise of TikTok and short-form video? What are some other really core features or traits that excite Jeff when he sees them in an early marketplace? What are some massive red flags for Jeff when he sees them early? 3.) How to Acquire and Retain the Demand Side of a Marketplace: Messaging and Brand: What are the biggest lessons Jeff has on how to craft the messaging of a marketplace to make it resonate with the target consumer? What are Jeff's biggest lessons from working with Brian Chesky on how they craft their messaging at Airbnb? What works? What does not work? Perfect Customer Cohorts: What does Jeff most want to see when examining prospective marketplace investment cohorts? What do the best have? What is the sign of a truly retained user in a marketplace? What is a good date duration to measure retention against? What are the biggest mistakes founders make presenting their cohorts? Lessons from Instacart: What are Jeff's biggest lessons from being on the Instacart board on cohorts? What makes good cohorts? How cohorts can seem bad but be good? 4.) Growth vs Profitability, CACs and LTV: Uber, OfferUp, Instacart, Deliveroo, respectfully, the level of profits these businesses are able to drive is questionable, why does Jeff believe marketplaces are good investments still? Many marketplaces start with poor unit economics, how does Jeff think about having the mental plasticity to project out to a time when unit economics could be better? Does Jeff pay attention to CACs at all? When are they important? When are they not? How can they be misleading? What is the best way for founders to present their CACs? 5.) It's Time to VC: Jeff Jordan: The Board Member What are the single biggest misalignments between VCs and their founders? How would Jeff describe his style of board membership today? How has it changed with time? What is the best way to deliver hard feedback as a board member? What are the biggest mistakes board members make? What does Jeff advise young board members today? What are the single best and worst changes that have happened at a16z in the last 24 months?

The question is: "are VCs still investing?". Today we are joined by Jason Lemkin; one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World's Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M. In Today's Episode on "Are VCs' Still Investing" We Discuss: 1. What Does it Take To Get Funded Today: Early-Stage: How has what VCs want in early-stage investments changed in this new environment? Should startups prioritize growth? Profitability? Capital efficiency? How long a runway is sufficient enough for founders to feel comfortable? Why does Jason believe most founders are still deluded that they are fundable? Growth Stage Companies: Is the growth stage totally dead? What will we see happen to all the companies that raised $50M+ at large valuations that have very little revenue? Why does Jason believe that any operator who joined a $BN company in the past few years will not make any money on their equity? What should they do now? Will we start to see down rounds and structured rounds at the growth stage? If so, when? Public Markets: Why does Jason believe this is a time unlike any he has seen before? Are we in full recession now in Jason's mind? In Dec 2023, will this be better or worse? Which are the most under-priced assets in the public markets today? Why does Jason believe VCs investing in public markets are losers? 2. Micro Funds Will Be Decimated and LP Behaviour in 2023 Why does Jason believe that micro-funds in 2023 will be decimated and unable to raise new funds? How will the majority of LPs approach new fund investments? How will LPs approach re-investing in their existing managers? How has what they need to see changed? 3. Marketing and Sales: We Need To Change Budgets and Targets How should CEOS be changing their marketing budgets in 2023? What are the single biggest mistakes CEOs are making in this downturn with regard to their marketing budget? How do sales targets need to be amended in the face of changing buying patterns? How do the best sales and marketing leaders respond to these changing budgets and targets? How do the worst respond?

How To Raise a Venture Capital Fund Over the last 4 years, I have raised around $400M across different vehicles from many different types of investors. Today I am going to break down the early stages of how to raise a venture capital fund and then stay tuned for a follow-up to this where we will break down a fundraising deck for a fund, what to do, what not to do etc. But to the first element. Your Fund Size is Your Strategy: The most important decision you will make is the size of fund you raise. So much of your strategy and approach will change according to your fund size target (LP type, messaging, documentation, structure etc). Remember, your fund size is your strategy. If you are raising a $10M Fund, you are likely writing collaborative checks alongside a follower, if you are raising a $75M fund, you will likely be leading early-stage seed rounds. These are very different strategies and ways of investing. MISTAKE: The single biggest mistake I see fund managers make is they go out to fundraise with too high a target fundraise. One of the most important elements in raising for a fund is creating the feeling of momentum in your raise. The more of the fund you have raised and the speed with which you have raised those funds dictate that momentum. So the smaller the fund, the easier it is to create that heat and momentum in your raise. LESSON: Figure out your minimum viable fund size (MVFS). Do this by examining your portfolio construction. In other words, how many investments you want to make in the fund (the level of diversification) and then alongside that, the average check size you would like to invest in each company. Many people forget to discount the fees when doing this math and so the traditional fund will charge 2% fees per year and so across the life of the fund (usually 10 years), that is 20% of the fund allocated to fees. Example: We are raising a $10M Fund. 20% is allocated to fees for the manager and so we are left with $8M of investable capital. A good level of diversification for an early-stage fund is 30 companies and so with this fund size, I would recommend 32 investments with an average of $250K per company. That is the $8M in invested capital. Big tip, I often see managers raising a seed fund and are only planning to make 15 investments, this is simply not enough. You have to have enough diversification in the portfolio if you are at the seed stage. No one is that good a picker. Likewise, I sometimes see 100 or even 200 investments per fund, this is the spray-and-pray approach, and although works for some, your upside is inherently capped when you run the maths on fund sizes with this many investments. A big element to point out in this example is we have left no allocation for reserves. For those that do not know, reserves are the dollars you set aside to re-invest in existing portfolio companies. Different funds reserve different amounts, on the low end there is 0% reserves and on the high end some even have 70% of the fund reserved for follow-on rounds. In this example, given the size of the fund being $10M with a seed focus, I would recommend we have a no-reserves policy. Any breakout companies you can take to LPs and create SPVs to concentrate further capital into the company. This is also better for you as the manager as you then have deal by deal carry on the SPVs that are not tied to the performance of the entire fund. So now we know we know $10M is our MVFS as we want to make at least 30 investments and we want to invest at least $250K per company. Great, next step. Set a target that is on the lower end, you can always have a hard cap that is significantly higher but you do not want the target to be too far away that LPs question whether you will be able to raise the fund at all. This is one of the biggest reasons why many do not invest in a first time fund, they are unsure whether the fund will be raised at all. The Team: Alongside the size of the fund, the team composition is everything, simply put, LPs like managers who have invested in the stage you are wanting to invest in moving forward. They like to see track record. IMPORTANT: I see so many angels write checks into breakout Series B companies and then go out and try and raise a seed fund with this as their track record. Do not do this, this does not prove you are a good seed investor but merely shows you have access at the Series B. These are very different things. With regards to track record, in the past, TVPI or paper mark-ups were enough, now there is a much greater focus on DPI (returned capital to investors). LPs want to see that you have invested before at that stage and they also want to see that the team has worked together before. You want to remove the barriers to no. If you have not worked with the partners you are raising with before, LPs will have this as a red flag, and as team risk, it is that simple. Navigating the World of LPs (Limited Partners) The size of the fund you are raising will massively dic

Henry Schuck is the Founder and CEO @ ZoomInfo. From ZoomInfo's founding moment, putting $25,000 on a credit card, Henry has led the company to today, with over $1BN in ARR, a market cap of over $10BN, and a team of over 3,600. This is one of the untold but truly great stories in software. In Today's Episode with Henry Schuck We Discuss: 1. From a $5,000 College Fund to Founding a $10BN Company: Why did Henry always believe early in life that he would be successful? Along the way doubt sets in, what did Henry do to combat that doubt when he questioned his own ability and potential? What does Henry believe he is running from? What is he running towards? How did seeing the work ethic of his single mother impact his work ethic with ZoomInfo? 2. Henry Schuck: The Leader: What does Henry believe is the difference between trust vs safety in team culture? Why does Henry believe safety is built through performance? How does Henry manage and communicate underperformance? How long do you give an under-performer? Why does Henry believe that happier teams outperform? What does Henry do deliberately and specifically to drive happiness in the business? ZoomInfo is magnitudes larger than some competitors who receive a lot more attention, how does Henry think about this? How does he manage his own ego as a leader today? 3. Henry Schuck: A Leader in a Changing Market: How does Henry maintain internal morale when employees see their stock options get smashed every day? Does it suck to be a public company CEO in the current market? What element is the worst? How are the buying patterns and behaviors of customers changing in 2023 vs 2021? How does this impact the sales cycle, retention rates, upsell plans, and the structure of the customer success teams? Dec 2023, will we be in a better or worse macroeconomic position? 4. Henry Schuck: Relationship to Money and Fatherhood: How does henry evaluate his relationship with money today? How has it changed over time? Why does Henry very rarely fly private planes? What does he believe this says about his values? How does Henry instill the same desire and worth ethic within his children despite being a billionaire? What does Henry know now that he wishes he could give to his 23-year-old self founding the company? Items Mentioned in Today's Episode: Henry's Favourite Book: The Happiness Advantage: The Seven Principles of Positive Psychology that Fuel Success and Performance at Work