20VC: Affirm Max Levchin on Why Grading Talent by Letter (A or B) is Total BS | How to Create a Culture of Post Mortems and Writing | Why You Should Only Study Failure Not Success & The Biggest Surprises Scaling to $18.7BN Market Cap

Howie Liu is the Founder and CEO @ Airtable, the fastest way to build apps for your business. To date, Howie has raised over $1BN with Airtable with the last round valuing the company at $11BN and an investor base including Benchmark, Thrive, Caffeinated, Greenoaks and Coatue to name a few. In Todays Episode with Howie Liu We Discuss: 1. Scaling into Enterprise: What are the single biggest challenges when moving from PLG to enterprise? Why does Howie believe you have only truly hit enterprise when you sign $1M contracts? How long did it take for Airtable to sign their first $1M ARR contract? How can founders know when is the right time to scale into enterprise? How does the product need to change with the scaling? 2. Enterprises: Do They Really Love AI: Why does Howie believe that enterprises are not jumping on AI yet? When does enterprise interest turn into enterprise buying and purchasing? What are the single biggest barriers to enterprises buying AI solutions today? Post-purchase, what are the biggest implementation challenges for enterprises with AI? 3. The Changing Sales Process: Are we seeing the bundling of tools within large enterprises today? Which categories and vendors are most vulnerable? Which will survive the cuts? What do vendors need to do to prove to CFOs that they need to remain in their budget? How has the customer success process changed over the last year with tightening budgets? 4. Howie Liu: AMA: Airtable famously got Benchmark to lead their Series C, how did this come to be when they famously always only do Series A? Why does Howie believe that it is total BS to suggest post-PMF, everything is good? What does Howie know now that he wishes he had known when he started Airtable?

25 Aug 202339min

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. Rick Zullo is the Co-Founder and General Partner at Equal Ventures. Prior to co-founding Equal Ventures, Rick was an investor at Lightbank, Prior to Lightbank, Rick worked with investment firms Foundation Capital, Bowery Capital, and Lightview Capital. In Today's Episode We Discuss: 1. Why Venture Capital Needs It's Jerry Maguire Moment: Why does Rick believe that VC needs it's "Jerry Maguire" moment? What needs to change? What needs to stay the same? Why does Jason believe we will see even more mega funds in 2024 and 2025? 2. Unicorns are So 2019: Why does Jason believe that "unicorn investing is mostly dead for bigger funds and none of them are looking for a $1BN outcome anymore?" Why does Rick believe that multi-stage fund investing at seed simply does not make sense? What does Rick believe many founders need to know when they take multi-stage money at seed? Of the over 1,000 unicorns created over the last few years, how many of them do Rick and Jason feel are actually unicorns today? 3. Efficiency and Growth: We Need it All: Why does Jason believe, as a founder you should be embarrassed if you ever had a RIF (reduction in force)? Last year many founders got a pass on growth as they were more efficient. Is that pass over? Do they need to get back to growth? What is the single biggest reason that companies do not scale from seed to Series A? What happens to the many companies with years of runway but no product-market-fit? Are we entering a new age of efficient company building or will we go back to high burn environments and excessive spending? 4. Entering the World of LPs: If Jason and Rick were to advise LPs today on how much to discount the value of their venture books, what advice would they give? How have markups completely corrupted the venture ecosystem? How does LPs being incentivized by paper-marks make the industry even more screwed? What are the single biggest misalignments between GP and LP?

23 Aug 202354min

Nick Huber is a serial entrepreneur, investor, and content creator focused on real estate and small business. In the last 9 months, Nick has co-founded 6 companies including RE Cost Set, RecruitJet, Titan Risk, Blue Key Capital, Tax Credit Hunter, and WebRun Labs. His primary business, Bolt Storage, owns 1.8M sqft of self-storage facilities across 62 locations in 11 states.  In Todays Episode with Nick Huber We Discuss: Wealth: What the richest families in the world all understand and what the majority of people forget? What are the two best ways to make money as an employee? What do most forget/not do? Why money does make you happy and why society drastically undervalues wealth today? Why we should not be concerned by the levels of income inequality? Marriage and Parenting: 5. Why it is BS to not pass your wealth down to your children? 6. Why you have to let your kids suffer in order for them to grow? 7. How do you stop kids from becoming assholes if they are brought up with money? 8. Why the majority of the time, people choose the wrong partner? What should we look for? 9. What is the number one thing you can do to set your child up for success? Silicon Valley and Entrepreneurship: 10. Why entrepreneurship is not for everyone? Who is it for? 11. Why VCs are out of touch and naive? 12. What is the single biggest lie of Silicon Valley? 13. Why will so many would-be great entrepreneurs burn themselves out when they should not have to? Management and Brand Building: 14. How to build a brand today? Why you have to be controversial to be interesting? 15. How to deal with hate and criticism? Why you cannot please everybody? 16. Why woke culture can give you an advantage if you do not have it? 17. How to build a strategic network the right way? How to become a card in someone's rolodex? 18. What is the single worst thing you can do when hiring? 19. What do you do when you lose trust in an employee?

21 Aug 202357min

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. He is widely recognized as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors and prompt engineering. He has over 150,000 citations and served as an adjunct professor in the computer science department at Stanford. In Today's Episode with Richard Socher We Discuss: 1. The Decade-Long Journey to Becoming an AI OG: How did Richard first make his way into the world of AI over a decade ago? What are 1-2 of his biggest lessons from working with Marc Benioff? How did 5 years at Salesforce impact how he both thinks and operates? 2. Models: Does Size Matter: How important is model size? Is data size more important? What are the biggest misconceptions people have around models today? How does Richard respond to the suggestion that "many startups are wrappers around LLMs"? Are hallucinations a feature or a bug? 3. Where Does Value Accrue: Where does Richard believe most of the value will accrue; startup or incumbent? Which incumbents are best positioned to win? Which are the laggards and behind? What do many not see about the startup vs incumbent race in the AI war? 4. Open vs Closed: Which Wins: Does Richard favour Yann LeCun's open approach? Or is the world of AI more closed? What are the biggest challenges of an open ecosystem? What are the nuances that make both challenging? 5. Richard Socher: AMA: Why will carpenters be paid more than software engineers in 10 years? Why is AGI still way off? Are people too unrealistic? How much money does Google make off search every day? Why does that leave them vulnerable?

18 Aug 202345min

Brian Balfour is the Founder and CEO of Reforge. Previously, he was the VP of Growth @ HubSpot. Prior to HubSpot, he was an EIR @ Trinity Ventures and founder of Boundless Learning and Viximo. He advises companies including Blue Bottle Coffee, Gametime, Lumoid, GrabCAD, and Help Scout on growth and customer acquisition. In Today's Episode with Brian Balfour We Discuss: 1. Entry into Growth and Lessons from Hubspot: How did Brian make his entry into the world of growth? What does Brian know now about growth that he wishes he had known when he started in growth? What are 1-2 of his single biggest takeaways from his time at Hubspot that impacted his mindset? 2. The Foundations: What is growth? What is it not? What does Brian mean when he says "all growth can be boiled down to 4 things"? When is the right time to bring in your first growth person? Should the first growth person be senior or junior? Should the growth team be standalone or sit within an existing function? 3. The Importance of Product Channel Fit: What is product channel fit? How should founders approach it? How do you know when you have it? What are the single biggest mistakes founders make with regards to PCF? 4. Next Comes Channel Model Fit: What is channel model fit? How should founders approach it? What are clear indicators that you have or do not have channel model fit? What are the biggest mistakes founders make with CMF? 5. Finally, Model Market Fit: What is model market fit? How should founders approach it? What are clear indicators that you have or do not have model market fit? What are the biggest mistakes founders make with MMF? 6. Brian Balfour: AMA: Why is product market fit not enough? What does Brian mean when he says "revenue does not create usage"? What are the biggest dangers of mixing customers and users? What do Hubspot do better than anyone else to know when an existing product/strategy is dying? Is it always better to diversify marketing channels?

16 Aug 202357min

Tim Urban is the writer/illustrator and co-founder of Wait But Why, a long-form, stick-figure-illustrated website with over 600,000 subscribers and a monthly average of half a million visitors. He has produced dozens of viral articles on a wide range of topics, from artificial intelligence to social anxiety to humans becoming a multi-planetary species. Tim’s 2016 TED main stage talk is the third most-watched TED talk in history with 66 million views. In 2023, Tim published his bestselling book What’s Our Problem? A Self Help Book for Societies. In Today's Episode with Tim Urban We Discuss: 1. The Founding of Wait by Why: What was the a-ha moment for Tim that Wait but Why should be his life's work and sole focus? What does Tim know now that he wishes he had known when he started? What does Tim believe he is running away from? Why is he so fearful of constraints? 2. Wait But Why: The Scaling Journey to 600,000 Subs: What was the first piece to really go viral? How did that change the trajectory? What single piece is Tim most proud of? What piece is he least proud of? What has been the hardest element of scaling Wait But Why? What was the most surprising and unexpected elements of Wait But Why's scaling? 3. Topic Selection: Choosing What To Write: What does the process look like for Tim when deciding what topic to write about? How does Tim know what his audience will want to hear about vs what they will not? What topics has Tim thought would be interesting but post initial research, are not? 4. The Writing Process: How does Tim approach the writing process? How has his changed over time? What mechanisms does Tim put in place to avoid writers block? What are some of Tim's biggest tips to aspiring writers and authors? 5. The Distribution Process: How does Tim approach distributing the content once produced? What works? What does not? Why did Tim choose newsletter, Twitter and Instagram as his channels of choice? How important has the newsletter been to the growth of the business? 6. AI: Super-Intelligence and The Future: On reviewing his pieces on AI back in 2015, what does he believe he got right? What would he change with the benefit of hindsight? Is Tim more or less positive looking forward at AI proliferating through all of society? What is Tim most concerned about in the world right now?

14 Aug 202358min

Sam Lessin is a Co-Founder and Partner @ Slow Ventures with a portfolio including the likes of Airtable, Robinhood, Slack, Solana, PillPack and many more unicorn companies. Prior to Slow, Sam was a VP Product at Facebook having sold his company to Meta. Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. As for Frank, prior to QED, Frank was one of the earliest analysts hired into Capital One and spent almost 13 years there helping build many of the company’s business units and operational areas.  Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. In Today's Discussion on Why Seed is Broken We Discuss: 1. The Seed Model Was Broken and What Comes Now: Why does Sam Lessin believe the model for seed of a "factory line" was broken? What does he believe will replace it? Why does Jason Lemkin argue that this might not be the case for SaaS and enterprise? 2. Round Construction: YC, Multi-Stage Funds and Party Rounds: Why does Sam Lessin believe we have seen the end of party rounds? Why does Jason Lemkin disagree and we will see more than ever? Why does Sam Lessin believe the factory model of YC churning out companies is over? Where does Jason Lemkin believe the value lies in the YC model? Will the multi-stage funds remain in seed? How has their entrance and deployment changed the seed market? 3. VC Value Add at Seed: Is it BS? Why does Jason believe all talent arms in venture firms have failed? Why does Sam believe that no VCs provide value? Do the best founders really need help? Why do Jason and Sam disagree? 4. What Happens Now: Why does Jason believe that every manager can write off their fund from 2021? Who will be the winners in seed in the next 10 years? Why does Sam believe if you want to bet on AI, just bet on Meta or Microsoft? What will happen to the many companies with no PMF but 10 years of runway?

11 Aug 202353min

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. In Today's Episode with Jason Lemkin We Discuss: 1. WTF is Happening At Seed Right Now: Why does Jason believe seed is more active than ever? Is the pricing of seed rounds impacted since the downturn? Why does Jason believe it is not only not the end of party rounds but just the beginning of them? Why does Jason believe you cannot fail if you have $1M in ARR and an amazing founder? Why does Jason believe that seed investors cannot participate in "hot seed rounds" anymore? 2. Is Series A a Dead Zone: How does Jason analyze the Series A and B environment today? What has changed in what investors expect and want to see in potential Series A and B investments? What happens to the many companies who raised pre-emptive Series As and have 10 years of runway but no product-market fit? Why does Jason believe founders should offer to give the money back when it is not working? What happens to the Series A and B market in the next 18 months? When does it come back? 3. Growth: People are Too Negative! Why does Jason believe that growth is more active than many are giving credit for? What are the ARR benchmarks required to get a good growth round term sheet today? Why does Jason believe that VC DD is a load of BS? Why does Jason believe that every VC has fraud in their portfolio? Will they come out? 4. Ring That Bell: IPOs and M&A: Why does Jason believe 2024 will be an amazing year for IPOs? Why does much of the IPO market rely on Stripe and Databricks? What is needed for an amazing 2024 IPO market? How does Jason evaluate the M&A market in 2024? Will regulation get in the way? 5. Jason Lemkin: AMA: Why does Jason Lemkin believe this generation of workers will never work hard again? What is the only way for seed funds to make money investing in serial entrepreneurs? What does Jason know now that he wishes he had known when he started investing?

9 Aug 20231h 9min