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 for more information on the podcast, show notes, resources and more.
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Now displaying: February, 2023
Feb 27, 2023

David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David is also the Chairman of GoodDog, a marketplace to find pets online.

In Today's Episode with David Tisch We Discuss:

1.) From Techstars To Founding BoxGroup:

  • How did David start his own firm in the form of Box having started at Techstars?
  • What advice from Brad Feld does David always remember and hold close?
  • What does David know now that he wishes he had known when started investing?

2.) The Debate: The Math Does Not Work: Portfolio Construction:

  • Ownership Does not Matter: How does David justify writing $100K checks from a $127.5M early-stage fund? Even if it is a home run, it does not make a difference to the fund?
  • Level of Diversification: If David is writing small checks like this, with his fund size he will have hundreds of companies, what does David believe is the right level of diversification?
  • Reserves management: How does David think about the ratio of initial to reserves when deploying the funds today? How does reserves management change in a recession?
  • How does David prevent other VCs from using this to try and push him down to always writing a $100K check?
  • Why does David believe that the size of check he is able to invest is the VC's problem and not the founders?
  • Price Sensitivity: How does David assess his own relationship to price today? Why does he believe that company valuation is not something that the investor controls?

3.) Advice to Founders Raising Rounds:

  • What does David believe is the #1 role of the CEO?
  • What are the three most important variables for founders to focus on when raising their round?
  • How should founders analyze the tradeoff between the brand of the VC and the size of the round?
  • Does signaling really make a difference when a large fund invests at seed?
  • How did multi-stage funds change the seed landscape forever with a new product?
  • Who does David believe are the tourists in early-stage venture? Will they leave in the recession?

4.) David Tisch: AMA:

  • Why does David believe that consumer social is not fun anymore?
  • Who when they send him a deal does David take it most seriously?
  • How does David want to ensure that bad VC behaviour is exposed?
  • What would David most like to change about the venture landscape today?

Feb 24, 2023

Joey Levin is the CEO of IAC where he has overseen the constant evolution of the company, including the initial IPO and subsequent spin-off of Match Group, the spin-off of Vimeo, and the acquisitions of Angie’s List and If that was not enough, in October 2022, Joey was also appointed as CEO of Angi Inc. In addition to this, Joey also serves on the boards of IAC, Turo, and MGM Resorts International.

In Today's Discussion with Joey Levin We Discuss:

1.) The Makings of a Great Leader:

  • When Joey was younger, what did he want to be when he grew up?
  • What is Joey's biggest advice to people coming out of college/university at this time?
  • What 1-2 things does Joey credit his internal and fast rise in IAC to?

2) Value Investing is BS & The Markets Today:

  • Why does Joey believe the idea of "value investing" is BS?
  • What 1-2 behavior traits of investors in the last few years were most dangerous?
  • Why does Joey believe that the current market is reasonable and now is the new normal?
  • How does Joey keep internal morale high when people have become accustomed to high stock prices?
  • Does Joey believe in the statement, "be greedy when others are fearful and fearful when others are greedy"?

3.) Simplification is the Secret to Margin & Messaging 101:

  • Why does Joey believe simplification is the core of high margins?
  • How can startups and scale-ups identify where to simplify first? What are the subsequent steps?
  • Why does Joey believe that the best values should make you feel uncomfortable?
  • What is a lesson from Joey's father on what makes truly great messaging?

4.) Parenting, Money and Marriage:

  • How does Joey reflect on his own relationship to money today?
  • What are 1-2 lessons taught by his mother on how to approach money and wealth?
  • What does Joey believe is the secret to truly happy marriages?
  • What are Joey's biggest lessons on what it takes to be an effective and good father?

Feb 22, 2023

Kevin Systrom and Mike Krieger are the co-founders of Instagram. Since its release in 2010, Instagram has become of the most significant products in modern society shaping the way millions of people engage with the world around them. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized news feed driven by artificial intelligence.

In Today's Show with Kevin Systrom and Mike Krieger We Discuss:

1.) The Perfect Partnership:

  • Question from Josh Kushner @ Thrive: What makes Kevin and Mike such a great partnership?
  • What was the last disagreement they had? How was it resolved?
  • They built Instagram in person, in an office. They are building Artifact remotely, what has changed in the way they operate when comparing remote to in-person?

2.) Why Social Networks are Broken & The Next Frontier:

  • Why does Kevin believe social networks today are broken and should be less social?
  • What fundamental premise are social networks built on that Kevin believes is wrong?
  • How will AI and machine learning be central in the next wave of social?
  • How do Kevin and Mike evaluate TikTok and the next wave of content discovery?

3.) Welcome Artifact: The Comeback:

  • Why does Kevin believe they chose the worst idea for their new company? Why is it?
  • Were they nervous about founding Artifact and expectations being so high given Instagram?
  • Why does Kevin argue that Artifact is not actually a "news app"?
  • What does Kevin believe is the biggest lesson Apple taught us about messaging?

4.) Family, Money, San Francisco:

  • Why does Kevin believe that SF will return as the centre of tech once again?
  • Why does Kevin believe that many millennials in the workforce today are entitled and soft?
  • How has becoming a father changed the way Kevin and Mike operate and execute?
  • How do Kevin and Mike assess their relationship with money today? How has it changed?

5.) Hiring, Investing, Managing:

  • What are some of Kevin and Mike's biggest lessons when it comes to hiring?
  • What are the single biggest hiring mistakes they have made?
  • Is it wrong to not hire someone because they are really really boring?
  • What are the biggest lessons for Kevin and Mike from their angel investing?

Feb 20, 2023

Zach Lawryk is Head of Solutions Consulting @ Rippling, what is solutions consulting? They are the product expert in the solution that ties a business value to help support the sales rep in the execution of their quota. And there is no one better than Zach, prior to leading the solutions consulting team at Rippling, Zach was VP of Solutions Consulting at Slack where he scaled the SE team from 10 to 200. Before Slack, Zach was Head of Solutions Engineering @ Optimizely and before that was Director of Sales Engineering at Box.

In Today's Episode with Zach Lawryk We Discuss:

1. ) WTF is Solutions Engineering:

  • What is Solutions engineering and why is it important?
  • How does a software developer turned lawyer become one of the OGs of Solutions Engineering?
  • What is the single biggest piece of advice Zach gives to graduates entering the workforce today?

2.) When and Who: Building the Foundations:

  • When is the right time to hire your first solutions engineer?
  • Should this be a senior hire or a more junior hire? What experience is ideal?
  • Would Zach rather have someone who has sold to the same customer segment or sold to the same deal size? What are the challenges with each?

3.) Making the First Hire: The Process:

  • What is the right hiring process for solutions engineers?
  • Which members of your existing team should be involved in the process?
  • What are some of Zach's favourite questions on the candidates past to determine quality?
  • What are the best case studies and tests to give potential hires to test their aptitude?
  • What are the biggest red flags in the hiring process for solutions engineers?

4.) Integrating into the Team: Making it Work:

  • What is the optimal onboarding process for solutions engineers?
  • Why does Zach think it is important they spend time with customer success in their first month?
  • What is the right way to measure the effectiveness of SE's?
  • How should the entrance of SE's impact the close rate and comp structure for AE's?
  • How can sales leaders prevent division and friction between AEs and SEs?

Feb 17, 2023

Aloe Blacc is a GRAMMY nominee and the voice behind such hits as Wake Me Up, The Man, SOS, I Need A Dollar, and many more. Aloe has toured the world, won countless awards but his latest album, All Love Everything, is the singer-songwriter’s first collection of material written as a father. “Becoming a father made me want to share those experiences in music,” he says, admitting it’s a challenge to translate such a powerful thing into lyrics and melody. If that was not enough, Aloe is also an entrepreneur with the founding of his new company, something we discuss in the show today.

In Today's Discussion with Aloe Blacc:

1.) Entry into Music and Running From Fame:

  • How Aloe first fell in love with music and made his foray into the world of music from Ernst & Young?
  • Why does Aloe believe he is running from fame? What does it bring that he does not like?
  • What does Aloe believe he is running towards? How has this changed?

2.) The Art of Storytelling:

  • How does Aloe think about what it takes to be truly great at storytelling?
  • What is the difference between a great vs an average story?
  • How has his style of storytelling changed over time?
  • What are the biggest mistakes that people make in storytelling?

3.) The Songwriting Process 101:

  • What is Aloe's process for writing new songs?
  • How does he take an idea and expand it, test it and execute against it?
  • How did "Wake Me Up" with Avicci come about? What was the creation process there?
  • What was it like working with Avicci? What did Aloe learn from him about being liked?

4.) Marriage, Fatherhood, and Global Stardom:

  • What does Aloe believe is the key to truly successful marriages?
  • How does Aloe retain a sense of romance with intense work pressures?
  • How has becoming a father changed the way in which Aloe thinks and operates?
  • What is Aloe's love language? How has doing this with his wife changed their relationship?

Feb 15, 2023

Mike Duboe is a Partner @ Greylock where he sits on the board of Builder, Inventa, Novi, Pepper, Postscript. Prior to entering the world of venture, Mike was the first in-house growth hire at Stitch Fix, where he built and led the Growth organization helping take the company through to their IPO. Before Stitchfix, Mike was the first growth hire at Tilt, where he built and oversaw multiple teams, including analytics, marketing, community, and growth product. He also served on YC’s growth advisory council and was a growth lecturer at Reforge.

In Today's Episode with Mike Duboe We Discuss:

1.) Entry into the World of Growth:

  • How Mike made his way from consulting at Bain to leading the growth team for Stitchfix?
  • What did Mike believe about growth 5 years ago that he no longer believes?
  • What does Mike know now that he wishes he had known when he entered the world of growth?

2.) When and Who To Hire:

  • How does Mike define the term "growth team"? What is their core role and responsibility?
  • Should the first growth hire be a senior growth lead or a more junior analytical lead?
  • What data foundations should founders have in place prior to their growth hire joining?
  • What are the most common ways founders fail to prepare for their first growth hires joining?
  • When does Mike believe is the right and crucial time for growth hires to be made?
  • Should these growth hires join existing teams or be put in standalone "growth teams"?

3.) The Hiring Process: How to Detect and Win the Best:

  • How should founders structure the interview process for their first growth hires?
  • What are the best questions to ask to reveal the quality of a potential growth hire?
  • What are the right case studies and tests to do to assertain their quality?
  • What are the different levels of comp package for different growth execs?
  • What are the single biggest mistakes founders make in the hiring process?

4.) Mastering Paid Marketing: Lessons from Stitchfix:

  • Why is CAC/LTV a BS metric? What should be used instead?
  • When is the right time to start really engaging with paid marketing?
  • How should marketing and growth teams determine budget on a per channel basis?
  • How much is the right mix between paid vs organic?
  • What are Mike's biggest lessons from making paid work so well at Stitchfix?
  • What are the single biggest mistakes Mike sees founders make today with paid marketing?


Feb 13, 2023

Tom Loverro is a Partner @ IVP where he has led or was actively involved in investments in Amplitude, Coinbase, Hashicorp and Datadog to name a few. As a result of his investing success, Tom was named to Forbes Midas List in 2021. Prior to joining IVP, Tom was a Principal at RRE Ventures.

In Today's Episode with Tom Loverro We Discuss:

1.) The Entry into Venture:

  • How did Tom make his way into venture first with RRE? How did the role with IVP come about?
  • Does Tom believe we will see many venture investors move firms with much of their existing expected carry cut in half with the changing landscape?
  • What is Tom's biggest advice to someone looking to make their way into the venture world?

2.) The Calm Before the Storm:

  • Why does Tom believe now is the calm before the storm?
  • Why does Tom urge founders to go out and raise now before the storm hits?
  • Is Tom already seeing pricing coming down for both early and late-stage companies?

3.) When The Storm Hits:

  • When does Tom believe the storm will hit?
  • Why does Tom believe when it does hit, it will be worse than The Great Financial Crisis?
  • How will VCs respond when the storm hits? How will it impact their investing cadence?
  • How will LPs respond when the storm hits? Will they cut back their manager commitments?
  • Does Tom have hope that their will be a new class of LPs in this new economic cycle?

4.) The Rounds That Happen When The Storm Hits:

  • Does Tom believe we will see a wave of down rounds when the storm hits? Why are they less common than people think?
  • In the eye of the storm, will we see further layoffs? Will we see firesales? Will we see a tidal wave of shutdowns?
  • Will large multi-stage funds with huge amounts of dry powder change their deployment pace?

The Survival Guide for the Storm:

1.) Raise Now:

  • Why does Tom believe that startups should raise now, not later? What amount of runway should they raise for in this environment?

2.) Cut, Cut and Cut Some More:

  • What amount of runway should startups be cutting to get to?
  • How will this impact marketing spend? Why are your marketing dollars more powerful now than ever before?

3.) Focus on Survival Not Valuation:

  • What does Tom mean by this? How can founders gain leverage with VCs when raising today?
  • How can founders instil a sense of urgency in their raise with investors?

4.) Bring on Operators with Experience:

  • Why would operators with experience join a struggling startup?
  • Will operators with experience not have a flight to safety and stay at their well-paid FANNG role?
  • Does this potential operator not shorten runway even further as they are often expensive?

5.) Unit Economics over Growth:

  • How can founders show investors a superior profile of unit economics moving forward?
  • Do investors not want both unit econ and growth today?

6.) Play Your Cards Right and Then Go on Offense:

  • How does Tom advise founders on the right time to go on offense?

7.) Be Decisive, Half Measures Rarely Succeed:

  • How does Tom define a half-measure? What is so wrong with half-measures?

Feb 10, 2023

Steve Pagliuca is a Senior Advisor at Bain Capital, the firm he joined in 1982 and as a Managing Director of Bain Capital, he has helped build the firm into one of the world’s leading investment companies with over $160 billion in assets under management. Steve is also a Managing Partner and Co-Owner of the World Championship Boston Celtics Basketball franchise. Steve is also co-owner and co-chairman of the Serie A professional football club, Atalanta Bergamasca Calcio. If that was not enough, Steve currently, serves on the Board of Directors of Burger King, Gartner Group, HCA, Warner Chilcott, and FCI. Huge thanks to Moshe @ Shrug Capital for making the intro.

In Today's Episode with Steve Pagliuca We Discuss:

1.) From Duffel Bags at Duke to Buying Sports Teams:

  • How Steve went from having a single duffel bag arriving at Duke University to entering the world of private equity with the founding of Bain's PE funds?
  • Did Steve always know he would be successful? What does Steve think about the importance between luck and timing?
  • How did Steve's mother impact how he approaches parenting and self-belief with his children?

2.) Buying Sports Teams: Not So Different to Companies:

  • When buying and running a sports team, what is the same, and what is different from buying and running a company?
  • What is Steve's biggest advice to new owners of sports teams?
  • What are the single biggest mistakes sports team owners make when they buy a team?
  • What happened with the Chelsea bid? Why did Steve lose? How did debt change the deal?

3.) The Future of Sports Ownership:

  • Why does Steve believe we have seen a massive rise in American and private equity buyers of both global sports teams but also European sports teams?
  • How has "new media" changed the inherent value that can be placed on a team? Why does it change the value? Which forms of "new media" are most important?
  • How much further can the value of these sports teams increase?
  • Does this massive increase in the price and assets of certain clubs not lead to a massive inequality in sports? What can be done to prevent this imbalance?

4.) Steve Pagliuca: The Person and Capital Allocator:

  • What is the single best investment advice Steve has ever received?
  • How does Steve think about his relationship to wealth today? How has it changed over time?
  • What does it take to have an amazing marriage and be at the top of your profession?
  • What were 1-2 elements that made Bain able to scale to the proportions of AUM that they have done? What would he have done differently?


Feb 8, 2023

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Ariel has raised over $2BN for Navan from some of the best including a16z, Zeev Ventures, Lightspeed, Greenoaks, and Elad Gil. Prior to TripActions, Ariel co-founded streamOnce, a business multimedia integration platform that was successfully acquired by Jive Software, where Ariel had previously served in a senior position following his time at Hewlett-Packard.

In Today's Episode with Ariel Cohen We Discuss:

1.) Why Education is Outdated and Wisdom to People Entering the Working World:

  • Why did Ariel not really attend many classes when he was a student?
  • What would be his biggest advice to young people leaving school today? Where would he focus?
  • Why does Ariel believe that traditional education is more outdated now than ever before?

2.) Why SAP and Salesforce Will Die:

  • Why does Ariel believe that SAP and Salesforce have not innovated for a decade?
  • Why does Ariel believe that Slack is a disaster inside of Salesforce?
  • What are the single biggest advantages that startups have over these large incumbents?
  • What can startups do to retain innovation and speed as they scale into becoming an incumbent?
  • Why are the best founders willing to kill their own projects?

3.) Growing a Business 3x and Raising at a $9.2BN Valuation in COVID:

  • How did Ariel grow the business 3x with all travel being banned?
  • What were the tactics to blitz scaling during COVID?
  • How did Ariel approach his investors for a new round in the middle of COVID? How did he get such a high price in the midst of a global pandemic?
  • What is the bull case for how Navan can be a $40BN company?

4.) Margins Matter: Gaining Leverage Through Additional Margin:

  • With Navan's 80% margin, they have 30% higher margins than other competitors, how do they have such high margins?
  • With the additional 30%, how does Ariel plan to scale Navan's reach and use the margin to do so?
  • How does OpenAI play a role in helping Navan increase its margin even further?

Feb 6, 2023

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. Today, Orlando directs the firm’s strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street’s best dealmaker" in 2019, and he was dubbed "Private equity’s king of SaaS" by the Financial Times in 2021.

In Today's Episode with Orlando Bravo We Discuss:

1.) From Puerto Rico Roots to Wall Street's Best Dealmaker:

  • How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him?
  • Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors?
  • What does Orlando know now that he wishes he had known when he started his career?
  • Why does Orlando disagree with setting timelines in life? Why does it not help?

2.) The Secret to Success in Value Investing:

  • What is good value investing today? What is it not?
  • What three things does Orlando look for when doing a deal and acquiring a company?
  • Why is every company in the world worth its future cash flows?
  • How important is price today? How does Orlando reflect on his own price sensitivity?
  • Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022?

3.) WTF is Happening In Markets Today:

  • How does Orlando reflect on where the market is today?
  • Is this the new normal? How does Orlando expect the market to change over the next 12 months?
  • Why does Orlando believe that the best companies win in the worst times?
  • Is this the result of quantitative easing on behalf of central banks? Who is to blame?
  • How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife?

4.) Orlando Bravo: The Leader, Father and Husband:

  • What is Orlando's biggest fear in investing? How has this changed over time?
  • How does Orlando reflect on his own relationship to money today? How has that changed?
  • What are Orlando's biggest parenting lessons from his mother?
  • Why does Orlando believe that for most people, their late twenties are their toughest?
  • How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up?
  • How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage?

Items Mentioned in Today's Episode:

Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

Feb 3, 2023

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org. 

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter.

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos.

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay.

Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. 

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack. 

For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015.

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012.

In Today's Episode on How to Hire a Product Manager, We Discuss:

1.) When to Hire Your First PM:

  • What are the core signs that the founder must delegate and hire their first PM?
  • What are the first things that are breaking when you do not have one but need one?
  • How does the timing of the first PM differ when comparing B2B vs B2C?

2.) What is the Right Profile:

  • What should founders look for in this first PM hire? What traits make the best?
  • What are the biggest red flags in the personalities and styles of potential candidates?
    • Should they have experience in the product domain they are entering?
  • What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume?

3.) The Hiring Process: How To Hire a Product Manager

  • How do we structure and run the hiring process for this person?
  • What tests can we do to understand if they have the skill set we need for the role?
  • How do we structure a hiring panel to make this process more effective?
  • What are the biggest mistakes founders make in the hiring process for PMs?

Feb 1, 2023

Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, EBITDA positive since Sept 2022, 85%+ gross margins, and over $5BN paid out to 250,000 people. Alex has raised over $679M with Deel, pricing the company at the last round at $12.1BN. Investors in the company include a16z, Spark Capital, Coatue, and many more.

In Today's Episode with Alex Bouaziz We Discuss:

1.) From Student in London to Decacorn Founder:

  • How Alex made his way into the world of startups and how he came up with the idea for Deel?
  • Did Alex always know he would be successful when he was growing up?
  • What does Alex know now that he wishes he had known when he was starting?

2.) The Importance of Execution:

  • How important does Alex think speed of execution is for startups?
  • What can startups do to deliberately increase their speed of execution?
  • How does Alex think about the dilemma of losing quality with speed?
  • What does Alex think you do need to go slow on to ensure it is perfect?
  • How does Alex think about focus and prioritisation today with Deel?

3.) Scaling to $295M in ARR in 3 Years:

  • When did Alex know he had true product-market fit with Deel?
  • How did Alex use a 50-person Whatsapp group to both determine product market fit and to navigate product direction for the company?
  • What was the key to Deel's blitz scaling strategy? What worked? What did not work?
  • How did Alex hire 2,000 people in such a short space of time?
  • What broke first in the organisation? How could they have prevented it?

4.) Secondaries, Angel Investing and Wealth Management:

  • How much did Alex take out in secondaries in the last round of funding?
  • How did Alex determine how much cash to allocate to angel investing?
  • Why does Alex believe most founders make poor angel investments when they have cash?
  • What have been Alex's biggest lessons from investing? How has it changed how he operates?
  • Why should all founders be super transparent in investor updates?