Rich Liu is the CRO @ Everlaw and a unicorn GTM exec having scaled five multi-billion dollar tech unicorns across two IPOs, a successful acquisition, and numerous funding rounds. Prior to Everlaw, Rich architected the GTM motions for companies like Navan (TripActions), MuleSoft, and Meta (Facebook). As a result of his incredible success, Rich has been recognized as a 2021 Top 100 Global Sales Leader.

In Today's Episode with Rich Liu We Discuss:

1. Entry into the World of Sales:

• How Rich made his way from biochemistry into the world of sales?
• What is 1 takeaway from his time at Navan, Meta and Mulesoft that has shaped how he thinks about sales today?
• What does Rich know now that he wishes he had known when he entered the world of sales?

2. Sales Today: What is Happening?

• What are the biggest sales leaders saying today about price sensitivity and deal cycles?
• What has changed in the way companies buy software with the macro downturn?
• What do companies need to do to get deals over the line today?
• How do startups need to change the way they message to enterprises in order to sell today?
• How has the renewals process changed? What does this mean for customer success teams today?

3. PLG vs Enterprise: When and How?

• Is it possible to do both PLG and enterprise at the same time?
• Is it easier to start with enterprise and move to PLG or visa versa?
• How does the type of sales leader you need change dependent on the motion?
• When is the right time to move from founder-led sales to sales team?
• How does one know whether to hire a junior jack of all trades or a senior sales leader?

4. How To Hire The Best in Sales:

• How does Rich structure the hiring process for all new reps today?
• Does he use case studies to determine their depth and ability? Is the case study of the company they are interviewing at or a fresh company?
• What questions does Rich ask every candidate for a new role?
• What are some of the biggest red and green flags in how candidates talk in interviews?

TJ Parker is the co-founder and former CEO of PillPack. TJ Raised over $100M in financing, grew the company to more than 1k employees, and successfully sold the business to Amazon for $1B in 2018. As of last week, TJ was announced as the newest Partner @ Matrix Partners where he will initially focus on health opportunities from concept to series A.

In Today's Episode with TJ Parker We Discuss:

1.) From Growing Up in Pharmacies to Selling to Amazon for $1BN:

• How did TJ seeing the pharmacy industry from his parents lead him to believe there was a $BN company to be built in the space?
• What does TJ know now that he wishes he had known when he started the company?
• What does TJ believe he is running from? How does that impact his own style of parenting?

2.) The Truth About Entrepreneurship:

• Why do the best founders have to get comfortable in an environment of uncertainty? What have been some of TJ's biggest lessons in how to do this?
• Why does TJ believe the role of the CEO is to set the vision and get out of the way? What roles can only the CEO do? How does TJ approach delegation? What have been some of his core lessons?
• Does TJ believe being naive is a superpower when starting a company? What do founders need to know vs what do they not need to know when starting a business?

3.) Speed of Execution and Decision-Making:

• How important does TJ believe speed of execution is for startups today?
• What can founders do to create a culture of rapid decision-making? What works? What does not?
• What does TJ believe are 1-2 of the single best and worst decisions he made with PillPack?
• What are some of the biggest mistakes TJ sees founders make both in speed of execution and then also in decision-making processes?

4.) The Crucible Moments: Lawsuits & Acquisitions:

• How did an incumbent come days away from shutting down PillPack?
• How did they save the company? How does TJ deal with those moments of intense stress?
• How did the Amazon acquisition come to be? Why and how did the prior acquisition fall through?
• Does TJ regret the sale to Amazon? How was life at Amazon post-acquisition?

One of the core questions in AI and investing today; who wins, startups or incumbents? Startups have speed and innovation but incumbents have scale, resources, and distribution?

Today we hear from 6 leading investors and founders discussing where they place their bets who has the advantage; startups or incumbents?

Emad Mostaque is CEO @ StabilityAI, the parent company of Stable Diffusion. To date, Emad has raised over $110M with Stability with the latest round reportedly pricing the company at $4BN. 

Yann LeCun is VP & Chief AI Scientist at Meta and Professor at NYU. He was the founding Director of FAIR and of the NYU Center for Data Science.

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

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.

Vince Hankes is a Partner @ Thrive Capital where he has led the firm’s investments in OpenAI, Melio, and Airplane.dev. Prior to Thrive, Vince learned the craft of venture from Lee Fixel @ Tiger.

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, a $230M fund that invests $1-25m in companies that leverage technology discontinuities into go-to-market advantages.

The Question of the Day:

• Who wins? Startups or Incumbents?

David Alleman is the Co-Founder and Co-Chairman @ On Running one of the fastest-growing global sports brands with over 17 million products sold in 60+ countries. In 2021, On went public on the NASDAQ and today has a market cap of $8.7BN. However, it all started with three friends in the mountains experimenting with making shoes with pieces of garden hose to create a running shoe with a totally different feel.

In Today's Episode with David Alleman We Discuss:

1. From the Swiss Mountains to NASDAQ IPO:

• What was the initial a-ha moment for David and his co-founders with On Running?
• How did they make the first shoes?
• What are some of the biggest lessons for David in V1 product build?
• What does David know now that he wishes he had known at the start? Is naivete always good?

2. The Launch: First Customers:

• How did On get their first customers?
• What can products and companies do to instill true customer love in those first customers?
• What was the hardest element of launching On to their first customers?
• How does David analyze and use customer feedback? What does he listen to vs not?

3. Retail: Expanding into Own Store vs Partnerships:

• What are some of David's biggest lessons in how to make retail partnerships successful?
• How can brands create amazing experiences for customers in retailers that are not their own?
• Why did On decide to also have their own stores? How did this change the business?
• What have been David's biggest learnings on what it takes to do retail well with own stores?

4. Roger Federer: Working with a Legend:

• How did the relationship with Roger begin? Where was the first meeting? What was it like?
• How did Roger come to invest in On Running? Why did On not want to do the traditional athlete endorsement deal?
• What role does Roger play in the company today? How does he impact product development?
• What have been some of the biggest lessons for David from working with Roger?
• How much of an impact has Roger had on On Running as a business?

5. Financing, IPOs, and Brand:

• Does David wish they had raised venture capital sooner?
• If they had more money sooner in their journey, what would David have invested in earlier?
• Why did they decide to go public when they did? How has the journey been post being a public company? What changes? What is the same?
• What brand does Davist most respect and admire? Why? What brand decisions does David most regret? What would he have done differently?

Adam Besvinick is the Founder of Looking Glass Capital, a pre-seed-focused firm started in 2020. Before starting Looking Glass, Adam spent about 5 years at Deep Fork Capital and Anchorage Capital Group investing in pre-seed through Series C. Adam's portfolio across funds includes the likes of BigID, Transfix, NomNom, and Hone Health, to name a few. 

In Today's Episode with Adam Besvinick We Discuss:

1. How Twitter Led to Founding a Venture Firm:

• How did Adam make his way into the world of venture through Twitter?
• What are 1-2 of his biggest lessons from working with the legend, Chris Sacca?
• What does Adam know now that he wishes he had known at the beginning of his time in VC?
• What do most young VCs misunderstand when it comes to reputation?

2. Raising Fund I: The Process:

• How many LP meetings did Adam have to close Fund I?
• What docs and materials did he have for the fundraise? How does he advise other managers on doing docs for fundraises?
• How do different LP profiles want different things in the managers they work with?
• How did Adam approach first vs final close? How does he advise others managers on closing?
• How did Adam instil a sense of urgency in LPs to move and commit to the fund?
• What are 1-2 of Adam's biggest pieces of advice to managers raising a first-time fund?

3. Looking Glass: The Very Disciplined Pre-Seed Strategy:

• How did Adam decide on the fund size? Why is it the optimal fund size?
• What is the desired ownership for Adam? What level of dilution does he expect across the lifecycle of the company?
• What is the average check size? What is the average entry price?
• How does Adam approach reserves and follow-on checks?
• How does Adam reflect on his own relationship to price?
• Why does Adam not like the majority of pre-seed micro-fund strategies?

4. The Market: Multi-Stage Firms Destroying Seed

• Does Adam agree that "multi-stage firms have destroyed seed rounds"?
• How does Adam advise founders when they have multi-stage offers and seed firm offers?
• Who will be the winners and losers in the next 10 years of venture?
• Why is it harder than ever to advise founders on fundraising rounds today?

Tomer Cohen is the CPO @ Linkedin. Since joining in 2012, Tomer has served in key leadership roles, helping launch and scale new innovative member and customer experiences. He previously led the growth and development of LinkedIn’s Marketing Solutions portfolio and LinkedIn's consumer and mobile products. Prior to LinkedIn, Tomer worked as an entrepreneur with Greylock Partners and founded a company in the personal CRM space.

In Today's Episode with Tomer Cohen We Discuss:

1.) From Israeli Military and Chip Design to CPO @ Linkedin:

• How did Tomer make his way from the Israeli military to being CPO @ Linkedin?
• What does Tomer know now that he wishes he had known when he became CPO?
• What have been some of his biggest lessons from working with Reid Hoffman?

2.) Product: Art or Science:

• How does Tomer determine whether product is art or science? If he were to put a number on it, what would it be?
• How does Tomer determine whether to go with his gut vs go with the data on product decisions?
• How is AI changing the role of product managers and product leaders?
• What do product leaders and PMs need to do to stay up to date with the latest changes in AI?

3.) Linkedin: Review of Current Products: Feed, Stories, Messenger

• How does Tomer analyse the success of "the feed" in Linkedin? What worked? What did not work?
• Why did "Stories" not work in Linkedin? What went wrong? What did they learn?
• What is Tomer doing to tackle the spam issue in Linkedin? What are the biggest challenges associated?
• Why does Linkedin still have such poor messaging service? Why is it a difficult problem to solve for?

4.) AI Changes Everything:

• Why does Tomer believe this wave of AI is the most significant technological shift in our lifetime?
• Who will win the race in AI; startups or incumbents?
• Which model will work most efficiently; open or closed?
• Will we see large enterprises prefer bundled AI options or unbundled with specialised providers?

Guy Podjarny is the Founder of Snyk, the leading Developer Security platform, helping developers secure as they build. Guy was previously CTO at Akamai, co-founded Blaze.io (acquired by Akamai), and was the product manager of AppScan, the first AppSec scanner, through Sanctum, Watchfire and IBM. Guy is a public speaker, O’Reilly author, and an active early stage angel investor.

In Today's Episode with Guy Podjarny We Discuss:

1.) From Israeli Military to Founding a $10BN Company:

• How Guy made his way into the world of startups from the Israeli military?
• What is Guy running away from? Why does he hate tribalism so much?
• Does Guy believe serial entrepreneurship is valuable or naivety of young founders is good?

2.) The Secret to Finding Product Market Fit:

• Why does Guy believe PMF is a poorly defined term? How does Guy define PMF?
• What are the single biggest mistakes founders make while searching for PMF?
• What are the most important elements on messaging when it comes to PMF?
• If you have a horizontal tool, how do you message and resonate with specific audiences?

3.) Defensibility and Being First to Market:

• Does Guy believe that being the first to market is really that valuable?
• Does Guy agree that investors expecting defensibility on day 1 is wrong?
• Why does Guy think market leadership is way more important than first to market?
• What are the true defensible moats that can be built early today?

4.) Lessons from 100 Angel Investments:

• What have been the single biggest lessons for Guy from his 100 angel investments?
• What are the biggest mistakes angels make when investing today?
• How should founders present their market size to investors? Where do they go wrong?
• Does Guy invest in both painkiller and vitamin businesses? How does he compare them?
• Why is Boldstart Guy's favorite venture capital firm?

Nico Wittenborn is the Founder of Adjacent, one of the best early-stage firms created over the last 5 years. Before starting Adjacent, Nico spent over 3 years at Insight Partners in New York and before that learned the craft of venture from some of the best in early-stage, Point Nine, where he spent over 4 years. Nico's portfolio across funds includes the likes of Revolut, Chainalysis, Oura, RevenueCat and PhotoRoom to name a few.

In Today's Show with Nico Wittenborn We Discuss:

1.) From Selling Mobile Phones to Leading Early-Stage Investor:

• How did Nico first make his way into the world of venture with Point Nine?
• What did Nico learn from his time with Point Nine and Insight? How did his time at each impact how he invests and runs Adjacent today?
• What does Nico know now that he wishes he had known when he started investing?

2.) Is Consumer Subscription Even a Good Place to Invest?

• With Calm ($2BN) and Duolingo ($6BN) as the market leaders and there only being two of them, is consumer subscription even a good place to invest?
• How does Nico pushback that retention for consumer subscription apps is so bad? What do many not see about consumer subscription retention numbers?
• How does Nico respond to the challenge of high customer acquisition cost and navigating challenging platform shifts in advertising, when investing in consumer subscription?
• What will the consumer subscription landscape look like in 5 years time?

3.) Adjacent: The Fund, The Strategy:

• Why does Nico believe if your fund model relies on $10BN outcomes, you are in trouble?
• How large is the latest Adjacent fund? What does the portfolio construction look like for the fund?
• How much diversification is the right level of diversification? How many companies per fund?
• How does Nico think about capital concentration on a per company basis?
• What are Nico's ownership requirements? How have they changed with funds?
• What is it about Nico's structure which enables him to be more collaborative than others?

4.) Nico: The Investor: Lessons:

• How does Nico reflect on his own relationship to price? When does he pay up? When does he not?
• What has been one of Nico's biggest misses? How has that changed his approach?
• Why does Nico not really compete with the large multi-stage funds?
• Why is Nico deliberately trying to reduce the amount of companies that he sees?

5.) The Future of Venture:

• How does Nico analyze the rise of solo GPs? What are the biggest pros and cons of the model?
• Why does Nico believe the large generalist funds are in trouble?
• Who is set to win and who is set to lose in the next 10 years of venture?
• Which seed firm would Nico invest in? Which Series A firm? Which growth firm?

Ryan Wiggins is the VP of Growth and Analytics at Mercury where he oversees a Growth team and founded the Analytics function. Prior to this, Ryan built Growth teams at WhatsApp, where he helped grow WhatsApp Business from 0->100M users, Workplace, and Facebook Ads. If that was not enough, Ryan is also an active angel investor.

In Today's Episode with Ryan Wiggins We Discuss:

1.) From US Department of Commerce to Leading Growth Teams:

• How Ryan made his initial foray into the world of growth with Facebook and Whatsapp?
• What does Ryan know now that he wishes he had known when he made the entry into growth?
• What advice does Ryan have for people who want to change their career but are not sure what they want to do?

2. ) Who and When: Building the Team:

• Should we hire a Head of Growth or a more junior growth hire first?
• What are the different profiles of growth hires? How do they change with business model?
• When is the right time to hire your first growth hire?
• What are the single biggest mistakes founders make on the timing of growth hires?

3.) How to Hire: The Process:

• Structurally, what is the right way to hire for a growth team? What does the interview process look like? What do you want to get out of each meeting?
• Should case studies be used, if so, should they be used for the company hiring or of the company where the candidate is from?
• What does the comp package look like for different growth hires?
• Who should be brought into the growth hiring process? What stage should they be involved?

4.) Onboarding: Setting Growth Up for Success:

• What is the ideal first 30,60 and 90 days for new growth hires?
• What can leaders do to ensure they are set up for the maximum chance of success?
• What are three of the biggest red flags bad growth hires show in the first 30 days?
• What are the biggest mistakes founders make in the onboarding process of growth hires?

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. Investors include Coatue, Lightspeed, Sound Ventures, OSS Capital and Airstreet Capital, to name a few. Prior to Stability, Emad was in the world of hedge funds, that was until his son was diagnosed with autism and he left to make a difference in the space and help find treatments and solutions.

In Today's Episode with Emad Mostaque We Discuss:

1.) From Hedge Funds to Finding Treatments for Autism to Leading the World of AI:

• How Emad made his way from the world of hedge funds to founding one of the leading AI companies of our time?
• How did Emad find a solution to parts of his son's autism with a $6 drug?
• How does Emad believe we can use AI to solve the majority of medical problems today?
• What does the future of healthcare look like with AI at the centre?

2.) Models: What is Real? What is False?

• Why no models today will be used in a year?
• Why all models are biased and how do we solve for it?
• Why hallucinations are a feature and not a bug?
• Why the size of your model does not matter anymore?
• Why will there be national models specified to cultures and nations? How is this implemented?

3.) Who Wins: Startups or Incumbents:

• Why does Emad believe there will only be 5 really important AI companies? Which will they be?
• How does Emad review Google's AI strategy following their news last week? Was their integration of Google and Deepmind recently a success?
• How does Emad assess Meta's AI strategy? Why does Zuckerberg now acknowledge the metaverse play was a mistake?
• How does Emad evaluate the approach taken by Amazon? Why are they the dark horse in the race?
• What can startups do to get a meaningful edge on the large incumbents? How do they compete with their distribution?

4.) The Next 12 Months: What Happens:

• Why does Emad believe the .ai bubble will be bigger than the dot com bubble?
• Why does Emad believe that the biggest companies built-in AI in the next 12 months will be services-based companies? How does the ecosystem look if this is the case?
• Why will India and emerging markets embrace AI faster than anyone else? What happens to economies that have large segments reliant on freelance work that AI replaces?
• Why will we see the death of many large content publishers and media companies? What does Emad mean when he says we will see the rise of "AI first publishers"?

5.) Open or Closed: What Wins:

• Why does Emad believe we must be open by default? Why does open win?
• Why does Emad side with Elon and believe we must pause the development of AI for 6 months?
• How does Emad evaluate the leaked memo from Google stating that neither Google nor OpenAI are ahead? What does this mean for the AI ecosystem?
• Where will the best AI talent concentrate? What do companies need to do to win the best talent?

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. After a postdoc in Toronto he joined AT&T Bell Labs in 1988, and AT&T Labs in 1996 as Head of Image Processing Research. He joined NYU as a professor in 2003 and Meta/Facebook in 2013. He is the recipient of the 2018 ACM Turing Award for "conceptual and engineering breakthroughs that have made deep neural networks a critical component of computing". Huge thanks to David Marcus for helping to make this happen.

In Today's Episode with Yann LeCun:

1.) The Road to AI OG:

• How did Yann first hear about machine learning and make his foray into the world of AI?
• For 10 years plus, machine learning was in the shadows, how did Yan not get discouraged when the world did not appreciate the power of AI and ML?
• What does Yann know now that he wishes he had known when he started his career in machine learning?

2.) The Next Five Years of AI: Hope or Horror:

• Why does Yann believe it is nonsense that AI is dangerous?
• Why does Yann think it is crazy to assume that AI will even want to dominate humans?
• Why does Yann believe digital assistants will rule the world?
• If digital assistants do rule the world, what interface wins? Search? Chat? What happens to Google when digital assistants rule the world?

3.) Will Anyone Have Jobs in a World of AI:

• From speaking to many economists, why does Yann state "no economist thinks AI will replace jobs"?
• What jobs does Yann expect to be created in the next generation of the AI economy?
• What jobs does Yann believe are under more immediate threat/impact?
• Why does Yann expect the speed of transition to be much slower than people anticipate?
• Why does Yann believe Elon Musk is wrong to ask for the pausing of AI developments?

4.) Open or Closed: Who Wins:

• Why does Yann know that the open model will beat the closed model?
• Why is it superior for knowledge gathering and idea generation?
• What are some core historical precedents that have proved this to be true?
• What did Yann make of the leaked Google Memo last week?

5.) Startup vs Incumbent: Who Wins:

• Who does Yann believe will win the next 5 years of AI; startups or incumbents?
• How important are large models to winning in the next 12 months?
• In what ways does regulation and legal stop incumbents? How has he seen this at Meta?
• Has his role at Meta ever stopped him from being impartial? How does Yan deal with that?

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. Prior to Hugging Face, Clem was in product and marketing at two different startups both of which were acquired.

In Today's Episode with Clem Delangue:

1. From Tamagotchi to Leading the World of AI:

• How did a Tamagotchi startup turn into one of the hottest AI startups in the world?
• What does Clem know now that he wishes he had known when he started?
• What are Clem's biggest pieces of advice to founders on pivoting?

2. AI: Trend or Transformation:

• To what extent does Clem believe the current hype in AI is justified?
• What is overblown? What have been some true and groundbreaking developments?
• How far away does Clem believe AGI is?
• What is a massive misconception the public has that Clem wishes he could change?

3. Open vs Closed: Which Model Wins:

• Why does Clem believe the future of AI will be won by open-source?
• What is his reasoning to suggest closed is fundamentally a weaker model?
• Does Clem acknowledge that in the short term, enterprises will buy from a closed model with greater ease? How does he plan to tackle this?

4. Regulation: What Happens Now:

• What regulatory changes need to be made in the world of AI most urgently?
• Is Elon Musk right to suggest the immediate pausing of developments in AI?
• What does Clem believe to be the most likely scenario to AI regulation in the next 12 months?

5. Fundraising: Lessons and Reflection on Raising $160M:

• Do AI startups fundamentally cost more money than normal startups to build?
• Why does Clem not meet investors in between rounds?
• What does Clem believe is the most helpful thing an investor can do?
• What are Clem's spiciest takes on venture as a financing model?

Today's 20Sales is a special Mother's Day edition where we are joined by 6 of the best sales leaders who also happen to be rockstar mothers.

The Profiles

Maggie Hott is on the GTM Team (Go-To-Market) at OpenAI. Before OpenAI, Maggie was Director of Sales @ Webflow and before Webflow spent an incredible 6 years at Slack.

Stevie Case is the CRO @ Vanta. Prior to Vanta, Stevie spent an immensely successful 6 years at Twilio as VP of Mid-Market Sales.

Renu Gupta is an advisor and sales consultant to some of the fastest-growing SaaS companies today. Previously she has held sales leadership roles at Slack, Thrive and Dropbox.

Lauren Schwartz is the VP Enterprise Sales @ Fivetran. Before Fivetran, Lauren spent 4 years at Segment as Senior Director of Enterprise Sales leading to their acquisition by Twilio.

Julie Maresca is the Head of Global Accounts at Atlassian. Prior to Atlassian, Julie spent an immensely successful 6 years at Slack in numerous roles including Head of Enterprise Sales for North America.

Jessica Arnold is the VP of Global Sales Development @ Amplitude. Before Amplitude, Jessica was the Senior Director for Inside Sales North America at Dropbox for close to 6 years.

In Today's 20Sales Mothers Day Episode We Discuss:

1.) How have you navigated growing in your career at the same time, growing your family?

2.) How do you balance your career and being a mother - when do you lean in and out?

3.) What are some specific strategies or tools that have helped you maintain a work-life balance? 

4.) How do you prioritize your mental health and wellbeing while juggling your responsibilities at work and at home?

5.) How do you handle the guilt that many working mothers experience when they have to focus on their career?

6.) What are the unique challenges and advantages of being a mother in a sales leadership role?

7.) How has your experience as a mother influenced your leadership style and decision-making?

8.) How have you navigated going out on maternity leave without it having an impact on your career?

9.) America has one of the worst parental leaves of any country in the world. How can you advocate for parental leave if the existing policy isn’t up to par?

10.) What are some ways that companies can create a more inclusive and supportive environment for working mothers in sales leadership roles?

Chris Paik is a General Partner @ Pace Capital, an early-stage venture firm in NYC. Pace's first fund was $150M and their second was $250M. Before co-founding Pace, Chris was a General Partner at Thrive Capital where he spent an incredible 8 years having joined the firm when they were on their first $10M Fund.

In Today's Episode with Chris Paik We Discuss:

1. From Hipster to One of NYC's Best VCs:

• How Chris made his way from not knowing about venture capital to being one of the most prominent in NYC?
• What are 1-2 of his biggest takeaways from his 8 years at Thrive? How did they impact how he thinks about building Pace today?
• What are Chris' biggest lessons from working with Josh Kushner? What did Josh do to spot young talent in a way like no one else did?

2. The Core Pillars of Successful Venture Investing:

• "Invest in companies that can be described in a single sentence". What does Chris mean by this? How does that impact the type of companies he looks to invest in?
• "Business Model Fit is as important as PMF". What does Chris mean by this? How does he determine where a company has business model fit?
• How does Chris analyze his relationship to market sizing? How does Chris think about how willing he is to take a bet on market timing?
• Why does Chris believe that the more "virtuous" a company is, the less enterprise value it will have?

3. What is Wrong with Venture Capital: The Misalignments:

• What does Chris believe are the single biggest misalignments between VCs and Founders?
• What does Chris see as the biggest misalignments between VCs and LPs?
• Why does Chris believe we should scrap capital gains tax and all be taxed as an income tax?
• Why do acquisitions allow investors to be screwed over by the acquiring company?

4. The Future of Social and User Generated Content Platforms:

• How does Chris analyze consumer businesses according to "The Seven Deadly Sins"? Why does he call them, "The Seven Deadly Motivators"?
• What does Chris believe is the future for Substack? Why does it not have Business Model Fit?
• What are 1-2 of his biggest lessons from being on the Twitch board? How did that experience impact his mindset and approach to what good is in UGC and social?
• What does Chris believe is the number one thing to look for in a potential consumer social investment? What do so many miss?

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:

1. 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:

1. 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?