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

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Now displaying: 2023
Sep 29, 2023

Kevin Niparko is the VP of Product @ Twilio. Kevin joined Twilio through the acquisition of Segment where he spent an incredible 8 years in numerous different roles including as Head of Product. Before entering the world of product, Kevin was a Management Associate at the world-renowned, Bridgewater Associates.

In Today's Episode with Kevin Niparko We Discuss:

1. From Bridgewater to Head of Product:

  • How Kevin made his way from the world of asset management and analytics to leading product teams?
  • What are 1-2 of Kevin's biggest takeaways from his time at Bridgewater with Ray Dalio?
  • How did the 8 year journey with Segment leading to their $3BN acquisition impact his approach to product?

2. What Makes a Great Product Person:

  • Does Kevin believe that product is more art or science? If he were to put a number on it? What would it be out of 100?
  • Why does Kevin believe that all product people should learn to write?
  • Why does Kevin believe that the best product people are generalists and not specialists?
  • Why does Kevin think that analytics is an insanely good start for product people?

3. How to Hire the Best Product People:

  • How does Kevin approach the hiring process for product hires today?
  • What are the non-obvious traits of hires he looks for? How does he test for them?
  • Does Kevin use case studies? Where do many fall down? What do the best do?

4. Product Reviews: Good vs Great:

  • How often does Kevin do product reviews? Who is invited?
  • How have product reviews changed in a world where the company is now fully remote?
  • What is the difference between good and great product reviews?
  • What is the single best product decision Kevin has made? What did he learn?
  • What is the worst product decision Kevin made? How did that change his approach?

Sep 27, 2023

Christian Lanng is the Founder and Former CEO @ Tradeshift, a company he took from garage to unicorn raising over $900M for with a latest price of $2.7BN in 2021. Just last month, Christian stepped away from the company and is now Chairman @ Beyond Work, building a better work experience through AI native software.

In Today's Episode with Christian Lanng We Discuss:

1. Burnout: When it Hits:

  • How did Christian know when something was really seriously wrong? What were the signs?
  • How did being a founder literally almost kill Christian? How was that not a wakeup moment?
  • How does being a founder make you so out of touch with reality?

2. The Things We Are Never Told:

  • Why does Christian think one of the biggest crimes is the myth that everyone can be a founder?
  • What are the single biggest things about VCs that founders are not told?
  • Why does Christian believe fundraising is absolutely a game? What are the rules to win it?
  • What makes the best VCs? What makes the worst VCs?
  • Why does Christian not like to take a discount for a brand name VC?

3. The Chaos That Happens Inside a Company:

  • Why does Christian believe politics should not be discussed within companies?
  • What are Christian's biggest lessons on working with friends? Why after 14 years does Christian only have 3 friends that still talk to him?
  • How did Christian fire 50% of his leadership team and productivity not change at all?
  • Why does Christian believe US startups are inherently better than European ones?

4. Parenting and Relationship to Money:

  • Does Christian regret not being a present father for his child when building Tradeshift?
  • What are the two options as a founder you have when bringing up kids?
  • Was Christian scared to leave Tradeshift? How does he reflect on his relationship to money?

5. AI: Co-Pilot is BS, The Future Business Model and more...

  • Why does Christian believe co-pilot is the last dying breathe attempt from incumbents?
  • Why does Christian believe that per-seat pricing will die? What will replace it?
  • Why does Christian believe that AI will negate the importance of consumer-facing brands?
  • In what way does Christian believe that UI is total BS? How does it change over time?

Sep 25, 2023

Marc Benioff is Chair, Chief Executive Officer and Co-Founder of Salesforce and a pioneer of cloud computing. Under Benioff's leadership, Salesforce is the #1 provider of CRM software globally and one of the world's fastest-growing enterprise software companies. Benioff founded Salesforce in 1999, and it is now a Fortune 150 company with 70,000+ employees. Benioff is the owner and co-chair of TIME, and the founder of TIME Ventures. Benioff is the author of the New York Times bestseller Trailblazer: The Power of Business as the Greatest Platform for Change. Benioff was named “Innovator of the Decade” by Forbes and is recognized as one of the World’s 25 Greatest Leaders by Fortune.

In Today's Episode with Marc Benioff We Discuss:

1. The Future of San Francisco:

  • What would Marc do if he were in charge of San Francisco today?
  • What would he change with regards to housing, policing and crime?
  • Why does Marc believe there are doomsday proclaimers on SF? What do they have to gain?
  • Will Dreamforce always be held in San Francisco?

2. Money and Ambition: The Mind Behind a $200BN Machine

  • Does Marc believe that money makes you happy?
  • How has Marc's relationship to money changed over time?
  • How does Marc think about bringing children up in a more affluent home?
  • What does Marc advise anyone who is seeking "happiness" today?

3. Mastering Decisions and Prioritisation:

  • How does Marc assess his own decision-making framework today? Has it changed with time?
  • What is Marc's 5 step process to understand your own priorities today?
  • What does Marc believe are the three biggest priorities for Salesforce today?
  • What are the single biggest blockers that would prevent Salesforce from achieving their goals?

4. Marc Benioff: AMA:

  • What does great fatherhood mean to Marc?
  • Who would win the cage fight, Zuck or Elon?
  • What does a day in the life of Marc Benioff look like?
  • What does Marc think about work from home?

Sep 22, 2023

Christian Kleinerman is the SVP of Product @ Snowflake. Before Snowflake, Christian spent close to 5 years at Google as a Senior Director of Product Management @ YouTube working on their infrastructure and data systems. Before YouTube, Christian spent over 13 years at Microsoft serving as General Manager of the Data Warehousing product unit where he was responsible for a broad portfolio of products.

In Today's Episode with Christian Kleinerman We Discuss:

1. Lessons from the Greats:

  • How did Christian first make his way into the world of product?
  • What are 1-2 of his biggest lessons from working with Satya Nadella and Frank Slootman?
  • What are 1-2 of hs biggest product lessons from Google and Microsoft?

2. Generative AI: Real vs Fake:

  • How does Christian analyze the current generative AI landscape?
  • Which segments will be the fastest to adopt? Which will be the slowest?
  • What aspects of the ecosystems are overblown? Which are under-appreciated?
  • How does Christian respond to many VCs who suggest that many startups are simply wrappers on GPT?

3. Models 101: Why Size is Not Everything!

  • What matters more, the size of the data or the size of the model?
  • Will any of the models used today be used in a year?
  • Does Christian believe Alex @ Nabla is right in saying that "the most successful companies will be those that are able to transition between models the easiest"?
  • How are we seeing the evolution of model size impact the accuracy of result snad size of data required?

4. Incumbent vs startup & Open vs Closed:

  • Who is best positioned to win; startups or incumbents?
  • What are the nuances; which spaces are best served for startups to win vs incumbents?
  • Will open or closed source be the dominant mode?
  • What are the single biggest challenges preventing open from being successful?

Sep 20, 2023

Eric Paley is the Managing Partner at Founder Collective, one of the world’s most successful seed funds with investments in the likes of Uber, The Trade Desk, Coupang and Airtable.

Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of TwitchOkta, Lyft, Twitter and more.

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds with a portfolio including Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few.

In Today's Episode on Is the Venture Model Broken? :

  1. Is the classic seed model dead? Can seed funds play in a world of $25M valuations?
  2. Why is having a firm grasp of the present the best thing an early-stage investor can have?
  3. Why does Mike Maples believe no company with true product-market-fit has ever failed?
  4. Why does Eric Paley believe "go faster" is the worst startup advice?
  5. Why does Mike Maples believe there is a direct relationship between price and risk?
  6. Why does Mike Maples believe that outliers by their very nature are lower priced?
  7. Why does Eric Paley not focus on ownership? Why can it be dangerous?
  8. What are the biggest risks for founders raising at valuations that are too high?
  9. Why does Eric Paley believe we will have the biggest chasm between TVPI and DPI in the prior vintage of venture capital returns?
  10. Why does Eric believe the majority of SPACs were BS and great companies can always go public?
  11. Why does Jason believe that if multiples do not reflate, the venture model is broken?
  12. Why does Jason believe we will see the biggest hiring spree in tech next year?
  13. How has illiquidity allowed Eric Paley to make some of the best investment decisions?
  14. What is Mike Maples biggest lesson from selling Twitter stock early at $1BN?

Sep 18, 2023

Miles Grimshaw is a General Partner @ Benchmark, widely considered one of the best venture capital firms in history. Prior to joining the Benchmark Partnership, Miles was a General Partner @ Thrive Capital where he led investments in Airtable, Monzo, Lattice, Github, Segment, Slack and Benchling to name a few.

In Today's Episode with Miles Grimshaw We Discuss:

1. Straight into VC From University: From Yale to Thrive

  • How did Miles come to land a role with Josh Kushner and Thrive right out of Yale?
  • What are 1-2 of his biggest lessons from working with Josh @ Thrive for 8 years?
  • What does Miles know now that he wishes he had known when he started in venture?

2. The Pillars of Venture Capital: Sourcing, Selecting, Servicing:

  • What does Miles believe are the 5 core pillars of successful venture capital?
  • 1-5, what is his strongest and what is his weakest?
  • Does Miles really believe that VCs add value today?
  • What are the most clear ways that Miles have seen VCs destroy value in portfolio companies?

3. Investment Decision Making: From Github to Segment:

  • What is the single most important question that Miles has to answer to say yes to an investment?
  • How does Miles think about both market sizing risk and market timing risk?
  • What have been Miles' biggest hits? What did he learn from making those investments?
  • What have been Miles' biggest misses? What did he learn from missing Figma and Plaid?
  • What have been 1-2 of Miles's biggest lessons so far from working with Bill Gurley and Peter Fenton?

4. AI: What Happens Next:

  • Does Miles believe we are in an AI bubble today? How does he assess the landscape?
  • Why does Miles believe that the "Co-Pilot" strategy is an incumbent strategy?
  • Where does Miles believe the value will accrue; the application layer or the infrastructure layer?
  • What does Miles mean when he says the future is in "selling the work and not the software"?
  • What business model disruption and adoption disruption does Miles believe AI will enable?
  • Why does Miles believe that the analogy of AI to the rise of mobile is wrong?

Sep 15, 2023

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce.

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research.

Alex Lebrun is the Co-Founder and CEO of Nabla, an AI assistant for doctors. Prior to Nabla, he led engineering at Facebook AI Research. Alex founded Wit.ai, acquired by Facebook in 2015. 

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.

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 and Neeva.

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential. To date, Emad has raised over $110M with Stability with the latest round reportedly pricing the company at $4BN. 

Clem Delangue is the Co-Founder and CEO @ Hugging Face, the AI community building the future. To date, Clem has raised over $160M from the likes of Sequoia, Coatue, Addition and Lux Capital to name a few.

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. To date, Cris has raised over $285M for the company from the likes of Lux Capital, Felicis, Coatue, Amplify, and Nvidia to name a few.

Noam Shazeer is the co-founder and CEO of Character.AI. A renowned computer scientist and researcher, Shazeer is one of the foremost experts in artificial intelligence (AI) and natural language processing (NLP). 

The Two Most Pressing Questions in AI:

  1. What matters more the size of the model or the size of the data?
  2. Where does the value accrue in the next 5-10 years; to startups or to incumbents?

Sep 13, 2023

Suchit Dash is the VP of Core Product Experience at Reddit, responsible for the surfaces that millions of users interact with daily. Prior to Reddit, Suchit was a cofounder at Dubsmash, a short video platform that was used by millions globally and acquired by Reddit in December 2020. In just 10 days, Suchit scaled the product to an immense 43M users, and gained fans such as Neymar and Jimmy Fallon. Suchit previously held roles at Soundcloud and PayPal.

In Today's Episode with Suchit Dash We Discuss:

1. The Founding of Dubsmash & V1:

  • How did the founding of Dubsmash come to be?
  • Suchit scaled V1 of the product to 43M users in 10 days, what was the secret? What worked?
  • What were the first signs that all was not right?
  • How did the team respond to the realization that their retention numbers were terrible?
  • What are Suchit's biggest lessons and pieces of advice from this massive V1 and launch?

2. Data: Retention, Cohorts and The Smiley Face:

  • What specific data did Suchit and the team really use to understand their level of product market fit?
  • What level of retention were they looking for? What is average, good, and great in terms of retention in consumer social?
  • What is really important for founders to try and observe and analyze in net new user cohorts?
  • When and why did the team start to see the hailed smiley face of consumer returning to the app?

3. Battling TikTok:

  • Despite the resurgence, TikTok was roaring, what did TikTok do so well to take the market?
  • How did TikTok leverage both FB and Snap's ad platform to acquire so many users so fast?
  • What did TikTok not do well? What could they have done better?
  • How did TikTok pay and incentivize the creator community?
  • What are some of Suchit's biggest lessons and advice for founders battling a better-funded incumbent?

4. The Decision to Sell: Being Acquired by Reddit:

  • Ultimately, why did Suchit decide to sell the company to Reddit?
  • Why did the first two acquisition attempts fail?
  • What are 1-2 of the biggest pieces of advice Suchit has for founders debating whether it is right to sell their company?
  • What do all founders being acquired need to remember?
  • With the benefit of hindsight, if Suchit could do the acquisition process again, what would he do differently?

 

Sep 11, 2023

David Velez is the Founder and CEO of Nubank, one of the largest and fastest-growing financial institutions in the world. 1 in 2 people in Brazil alone have a Nubank account. Nubank's purple credit card in Mexico is the highest-rated NPS product of any consumer product in the world. Before founding Nubank in 2013, David was a partner at Sequoia Capital between 2011 and 2013, in charge of the firm’s Latin American investments group. Before Sequoia, David worked in investment banking and growth equity at Goldman Sachs, Morgan Stanley and General Atlantic.

In Today's Episode with David Velez We Discuss:

1. From Sequoia Partner to Creating One of the Largest Financial Institutions:

  • What was the Sequoia interview process like?
  • What questions did Doug Leone really dive into when hiring David?
  • What impressed David most about how Sequoia interview and win talent?
  • What are 1-2 of David's biggest lessons from working with Doug Leone?

2. From a Small House to a $BN Public Company:

  • What does David believe are the 1-2 core but non-obvious reasons why Nubank scaled so fast?
  • What does David believe are the most non-obvious but massive opportunities Nubank has to 10x from here?
  • Why does David believe emerging market fintech providers will be more valuable than Western fintechs?
  • What does David believe Western fintechs and regulators can learn from BRIC economy fintechs?

3. How AI Changes The Future of Financial Services:

  • How does David believe AI will change financial services?
  • What products are the lowest-hanging fruit? Which products will be harder for AI to serve?
  • How will AI handle the ambiguity of which master to serve; the consumer and their experience or the bank and their fees and profit motive?
  • Will banks need to own and operate their own models? If using other models, what will differentiate them when they are layers on top of someone else's technology?

4. David Velez: The Leader and Father:

  • What does it mean to be a great listener? How does David approach it?
  • What has been David's biggest lessons from Sequoia on culture? What works? What does not?
  • What are David's biggest pieces of advice to raise kids that are not spoiled and are hard-working and humble?
  • How does David think about "efficient giving" with the philanthropy he does today?
  • What is the big paradox and challenge in philanthropy today?

Sep 8, 2023

Doug Adamic is the CRO @ Brex and leads the company's revenue and growth strategy. Prior to Brex, Doug was most recently the Chief Revenue Officer at SAP Concur, a provider of travel spend management solutions and services. During his 16-year tenure oversaw an organization of 600+ employees. He was responsible for all aspects of revenue, generating go-to-market strategies and departments. Prior to SAP Concur, he had a five-year tenure as an Enterprise Sales Manager for Kronos, Inc.

In Today's Episode with Doug Adamic We Discuss:

1. Entry into Sales:

  • Does Doug believe that love of sales is innate or can be learned? When did he discover his love?
  • What does Doug know now about sales he wish he had known when he started?
  • What are 1-2 of his biggest takeaways from leading 600+ people at SAP?

2. Discovery, Pipeline and Qualification:

  • What are the three core reasons why companies buy software today? How do the best sales teams use those needs to get deals done fast?
  • What does great sales discovery mean today? Why do you have to make customers feel uncomfortable to understand their true needs?
  • What are the biggest mistakes sales teams make when asking questions, determining customer pain, willingness to pay etc etc?
  • Why does Doug believe that everyone in the company is responsible for demand creation?
  • What are the core pillars to success in qualification? Where do so many go wrong?

3. Getting Deals Done:

  • Why does Doug disagree that now is the hardest time to be selling? Are companies buying new software today?
  • What is the secret to opening up organizations that say they are not open for buying new software?
  • How can sales teams create multiple champions in a prospect? How can they determine who is really a buyer vs who is an influencer in a prospect?
  • What are the biggest tactics that can be used to reduce sales cycles and create urgency in a sales process?

4. Discounting, Trust and Deal Reviews:

  • What is a good reason to lose a deal?
  • What is a bad reason to lose a deal?
  • How does Doug and Brex conduct deal reviews? What makes a good vs a bad deal review?
  • What is the fastest way to lose trust either with prospects or with customers?
  • Why does Doug believe discounting is BS and should not be used?

Sep 6, 2023

Nikhil Basu Trivedi is Co-Founder & General Partner at Footwork, an early-stage focused venture firm investing its first fund. In his venture career, he has invested in the early rounds of several companies that have exited or are currently valued at over $1B, including Athelas, Canva, ClassDojo, Color Health, Frame.io, Imperfect Foods, Lattice, and The Farmer's Dog. Prior to Footwork, Nikhil was a Managing Director at Shasta Ventures, on the investment team at Insight Partners, and on the founding team at Artsy.

In Today's Episode with Nikhil Basu Trivedi We Discuss:

1. From Summer Intern to Founding a Firm: The 13 Year Journey:

  • How did Nikhil first make his way into venture as an intern at Insight Partners in NYC?
  • What does Nikhil know now that he wishes he had known on his first day in venture?
  • Why does Nikhil advise all young VCs to "not look at their business card"? Why does title not matter in venture?
  • Should founders meet with Juniors as well as GPs and more senior people?

2. Small Funds Outperform Large Funds:

  • Why does Nikhil believe that small funds outperform large funds?
  • Why is AUM the biggest bullshit metric in VC?
  • How does Nikhil advise seed stage founders who have offers from seed firms for smaller rounds at lower valuations and are weighing them against larger rounds with higher valuations from multi-stage funds?
  • Does Nikhil believe that platform value-added services really provide any value?

3. The Art of Investing:

  • What has been Nikhil's biggest investing win? How has it changed his approach to investing?
  • How does Nikhil prioritize between people, traction, and market? What is most important?
  • What has been Nikhil's biggest investing miss? How has that changed his approach?
  • Does Nikhil believe the great founders are immediately obvious?
  • Why is market size the single question that keeps Nikhil up the most?

4. The Dysfunctions of Venture Capital:

  • What are the single biggest areas of misalignment between GP and LP?
  • What do many GPs see and know well that LPs should know and see more of?
  • What are the biggest ways that decision-making breaks down in a venture fund?
  • Why does Nikhil believe that so much of the investment in AI is going to go up in flames?

Sep 4, 2023

Mudassir Sheikha is the CEO and Co-Founder of Careem. Over the last 11 years, Mudassir has scaled the service to more than 80 cities in 10 countries, with 1,400+ colleagues and more than 2.5 million Captains. With such success, in 2020 Uber announced they would be acquiring Careem for a reported $3.1BN. Prior to Careem, Mudassir co-founded “DeviceAnywhere”, a company that was acquired by “Keynote” in 2008 before joining the management consulting firm “McKinsey & Company” in Dubai.

In Today's Episode with Mudassir Sheikha We Discuss:

1. From McKinsey to $3.1BN Exit to Uber:

  • What was the founding a-ha moment for Mudassir with Careem?
  • What does Mudassir know now that he wishes he had known at the beginning?
  • What does Mudassir believe he is running away from?

2. Finding Product-Market Fit:

  • What is the single biggest mistake founders make when trying to find product-market fit?
  • Does Mudassir believe you have to do things that do not scale, to scale? What did Careem do?
  • What are some of Mudassir's biggest pieces of advice to founders on finding a core target audience and doing customer discovery the right way?

3. Competing with Giants: How To Win When You Cannot Outspend:

  • How did Careem beat Uber when they had 1/100th of their budget?
  • What advice does Mudassir have for founders who have competition that is much better funded?
  • What is the story of spending the night in bunk beds and barely sleeping before raising $300M the next day? How did that happen?

4. The Acquisition: How it Went Down:

  • How did Mudassir and Dara @ Uber first come to meet?
  • How did Dara's approach contrast with the prior approach of Travis Kalanick?
  • Why did Mudassir decide to sell and join Uber?
  • What were the main reasons or arguments against the acquisition?

5. Talk to me About:

  • Careem's Pakistan MD having to flee Pakistan for his safety post a marketing campaign?
  • Elon Musk likes one of Careem's promotional videos and why?
  • An investor who wired $1M with absolutely no paperwork?
  • The catch up meeting that turned into a $3BN offer?

Aug 31, 2023

Noam Shazeer is the co-founder and CEO of Character.AI, a full-stack AI computing platform that gives people access to their own flexible superintelligence. A renowned computer scientist and researcher, Shazeer is one of the foremost experts in artificial intelligence (AI) and natural language processing (NLP). He is a key author for the Transformer, a revolutionary deep learning model enabling language understanding, machine translation, and text generation that has become the foundation of many NLP models. A former member of the Google Brain team, Shazeer led the development of spelling corrector capabilities within Gmail, the algorithm at the heart of AdSense.  

In Today's Episode with Noam Shazeer We Discuss:

1. Entry into the World of AI and NLP:

  • How did Noam first make his way into the world of AI and come to work on spell corrector with Google?
  • What are 1-2 of his biggest takeaways from spending 20 years at Google?
  • What does Noam know now that he wishes he had known when he started Character?

2. Model Size or Data Size:

  • What is more important, the size of the data or the size of the model?
  • Does Noam agree that "we will not use models in a year that we have today?" What is the lifespan of a model?
  • Does Noam agree that the companies that win are those that are able to switch between models with the most ease?
  • With the majority of data being able to be downloaded from the internet, is there real value in data anymore?

3. The Biggest Barriers:

  • What is the single biggest barrier to Character today?
  • What are the most challenging elements of model training? Why did they need to spend $2M to train an early model?
  • What are the most difficult elements of releasing a horizontal product with so many different use cases?
  • Where does the value accrue in the race for AI dominance; startups or incumbents?

4. AI's Role on Society:

  • Why does Noam believe that AI can create greater not worse human connections?
  • Why is Noam not concerned by the speed of adoption of AI tools?
  • What does Noam know about AI's impact on society that the world does not see?

Aug 28, 2023

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. To date, Cris has raised over $285M for the company from the likes of Lux Capital, Felicis, Coatue, Amplify, and Nvidia to name a few. Runway’s customers include academy-nominated movies, TV shows, media companies, and creatives across industries.

In Today's Episode with Cris Valenzuela We Discuss:

1. From Childhood in Chile to Founding one of the Hottest AI Startups:

  • What was the founding moment for Cris with Runway?
  • His investors described Cris as an "outsider". Does Cris believe he is an outsider? What are the biggest pros and cons of being an outsider?
  • What does Cris believe he is running from? What is he running towards?

2. Models are not a Moat: Models 101:

  • What does Cris believe is more important; model size or data size?
  • Why does Cris believe that models are not a moat?
  • How does Cris think about the lifespan of models? Will any used today be used in a year?
  • Are hallucinations a feature or a bug? What are the nuances?

3. The World Has Got AI Wrong: We Need Different Stories:

  • Why does Cris believe the world has got AI wrong?
  • Why do we need different stories for what AI can do and will be? Who should tell them?
  • Why do groups like screenwriters riot and protest if the tool is empowering and not replacing?

4. Company Building 101: Hiring and Fundraising:

  • What are the biggest pieces of startup advice that are total BS?
  • What has been the single biggest lesson Cris has learned when it comes to fundraising?
  • Does Cris believe that VCs really add value?
  • What have been the single biggest hiring mistakes that Cris has made?
  • How has Cris structured their interview process to make it the best interview process in the world?

Aug 25, 2023

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?

Aug 23, 2023

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?

Aug 21, 2023

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:

  1. What the richest families in the world all understand and what the majority of people forget?
  2. What are the two best ways to make money as an employee? What do most forget/not do?
  3. Why money does make you happy and why society drastically undervalues wealth today?
  4. 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?

 

Aug 18, 2023

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?

Aug 16, 2023

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?

Aug 14, 2023

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?

Aug 11, 2023

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?

Aug 9, 2023

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?

Aug 7, 2023

Vinod Khosla is the Founder of Khosla Ventures, one of the leading venture firms of the last decade with investments in OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Prior to founding Khosla, Vinod was a co-founder of Daisy Systems and founding CEO of Sun Microsystems.

In Today's Episode with Vinod Khosla We Discuss:

1. The State of AI Today:

  • Does Vinod believe we are in a bubble or is the excitement justified based on technological development?
  • What are the single biggest lessons that Vinod has from prior bubbles?
  • What is different about this time? What is Vinod concerned about with this AI bubble?

2. The Future of Healthcare and Music:

  • How does Vinod evaluate the impact AI will have on the future of healthcare?
  • How does Vinod analyse the impact AI will have on the future of music and content creation?
  • Does Vinod believe that humans will resist these advancements?
  • Who will be the laggards, slow to embrace it and who will be the early adopters?

3. Solving Income Inequality:

  • Does Vinod believe AI does more to harm or to hurt income inequality?
  • What mechanisms can be put in place to ensure that AI does not further concentrate wealth into the hands of the few?
  • Does Vinod believe in universal basic income? What does everyone get wrong with UBI?

4. The Future of Energy, Climate and Politics:

  • Why is forcing non-economic solutions the wrong approach to climate? What is the right approach?
  • Why is Vinod so bullish on fusion and geothermal? How does fusion bankrupt entire industries?
  • How does the advancements in energy and resource creation change global politics?
  • Does Vinod believe Larry Summers was right; "China is a prison, Japan is a nursing home and Europe is a museum"?

5. Vinod Khosla: AMA:

  • What is Vinod's single biggest investing miss?
  • What does Vinod know now that he wishes he had known when he started investing?
  • Why did the Taylor Swift concert have such a profound impact on him?
  • What was Marc Andreesen like when he backed him with Netscape in 1996?

Aug 4, 2023

Ilir Sela is the Founder and CEO of Slice, the all-in-one ordering and marketing tech platform for local pizzerias. Through its partnerships, Slice has driven over $1B in earnings for over 18,000 independent pizzerias nationwide. Fun fact, Slice is also one of the largest employers in Macedonia and at one point, employed so many people there, they had to start their own school to train more people. Before Slice, Ilir started Nerd Force and sold it in 2008. Huge thanks to Jeff Richards (GGV) and Ben Sun (Primary) for some amazing questions today.

In Today's Discussion with Ilir Sela We Discuss:

1. From Macedonia to the Bright Lights of NYC and Bentley Buying:

  • How Ilir made his way into the world of startups having grown up in Macedonia?
  • How did his less affluent upbringing impact his approach to company building?
  • How does Ilir think about the importance of money? How did he come to buy a Bentley?
  • What does Ilir know now that he wishes he had known when he started?

2. Why Bootstrapped Was Best & The Decision to Fundraise:

  • Why did Ilir scale the business to $4M in revenue without ever fundraising?
  • What does Ilir believe are the benefits of scaling businesses with less money?
  • What would Ilir have done differently had he raised money earlier?
  • What advice does Ilir have for founders who see competitors raising more money than them?

3. Why Delegation is BS and Your Upbringing F***** You Up:

  • Why does Ilir believe that much of our upbringing can instill principles which make us a worse leader?
  • Why does Ilir believe it is BS to hire great people and get out of the way?
  • What are the single biggest mistakes Ilir sees founders make in company scaling?
  • What have been some of Ilir's biggest lessons in talent acquisition?

4. Decision-Making 101:

  • How does Ilir analyze his decision-making framework today?
  • Where does he need to improve as a leader today? What does he need to do to get there?
  • What has been the single best decision he made with Slice? What did he learn from it?
  • What has been the worst decision he has made in the scaling process? How did that change his mindset?

Aug 2, 2023

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box.

In Today's Episode with Lori Jimenez We Discuss:

1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook:

  • How Lori made her foray into the world of sales at the age of 15?
  • What are 1-2 of Lori's biggest takeaways from her time at Google, Facebook and Box?
  • What does Lori know now that she wishes she had known at the start of her career in sales?

2. The Sales Playbook: What, When and How:

  • How does Lori define the "sales playbook"? What is it not?
  • Should the founder be the one to create the sales playbook?
  • When is the right time for founders to make their first sales hires?
  • What is the right profile for the first sales hires?
  • Should founders hire 2 sales reps at a time? What are the pros and cons?

3. The Hiring Process: Building the Sales Team:

  • How does Lori structure the hiring process for all new sales hires?
  • What are the must-ask questions to ask in every sales hiring meeting?
  • What are the biggest red flags founders should look for when hiring for sales?
  • What are Lori's biggest lessons on how to navigate compensation discussions with potential sales hires?
  • What are Lori's biggest lessons on what title negotiation says about a candidate?
  • What are the single biggest mistakes founders make when hiring for sales teams?

4. Scaling the Machine: Bringing the Dollars In:

  • How does Lori approach discounting? When is the right time to do it?
  • Is old-school enterprise sales and entertaining dead? How has it changed?
  • How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal?
  • How does Lori approach multi-year deals? What is good? What is bad?

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