20VC: Why Operating Experience Becomes Irrelevant Fast and Operators Often Give Bad Advice to Founders, Is Silicon Valley Really Dead? Are Gen Z the Most Entitled Employees? What Will Happen to a Generation of Pre-PMF Companies with $50M in the Bank with

20VC: Why Operating Experience Becomes Irrelevant Fast and Operators Often Give Bad Advice to Founders, Is Silicon Valley Really Dead? Are Gen Z the Most Entitled Employees? What Will Happen to a Generation of Pre-PMF Companies with $50M in the Bank with

Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world's largest animation studio, known for Shrek, Kung Fu Panda, Madagascar and more. In 2016, DreamWorks Animation was sold to Comcast for $3.8 billion. Before founding DreamWorks, Jeffrey was Chairman of The Walt Disney Studios, where he took the studio from last place to first at the box office with hits like Three Men and a Baby, Pretty Woman, Father of the Bride and Sister Act. Most recently, Jeffrey co-founded WndrCo alongside Sujay Jaswa and has led WndrCo's investments in Airtable, Frame.io, Quibi, Vise, Placer.ai, NexHealth, Deel, and ID.me.

Sujay Jaswa is one of Silicon Valley's leading business innovators. At Dropbox, he created and led the company's global business and finance organizations. Sujay and his teams raised over $1 billion, launched and scaled Dropbox's products for businesses, created partnerships responsible for over 100 million users, executed some 20 acquisitions, and scaled the global business team from two to more than 500 employees in seven global offices. During this period, the company significantly scaled overall revenue from $12 million in 2010 to over $500 million run rate, Dropbox for Business revenue from $1 million to over $200mm run rate, and users from 15 million to 300 million. Most recently, Sujay Jaswa and Jeffrey Katzenberg co-founded WndrCo and Sujay has led WndrCo's investments in Figma, 1Password, Databricks, Pango, Pilot, Rally, Zagat / The Infatuation, and other great companies.

In Today's Episode with Jeffrey Katzenberg and Sujay Jaswa:

1.) From Dreamworks and Dropbox to Venture with WndrCo:

  • How did Jeffrey and Sujay both make their way into the world of venture from Dropbox and Dreamworks?
  • What was Jeffrey's single biggest lesson from his time leading Dreamworks and being in Hollywood?
  • What was Sujay's biggest takeaway from being at the helm as COO at Dropbox?

2.) Operating Experience is Irrelevant and Can Be Dangerous:

  • Why does Sujay believe that operating experience is irrelevant?
  • What are the single biggest mistakes that operator investors make when it comes to advising their founders?
  • What do both Sujay and Jeffrey do to try and refresh their operating experience in real time?
  • How did Quibi impact their willingness and desire to take large risk both investing and operating?

3.) Building Teams and Hiring People:

  • What are the single biggest hiring mistakes Jeffrey and Sujay have made?
  • What did Jeffrey mean when he said at Disney, "if you do not come in on Saturday, do not bother coming in on Sunday".
  • How do Jeffrey and Sujay feel about remote work? Why did it not work for them?
  • What did Alfred Lin @ Sequoia teach Sujay about the question all managers need to ask themselves on questing whether they should let someone go?

4.) Silicon Valley: Dead and Entitled?

  • Why does Jeffrey strongly disagree with the death of Silicon Valley?
  • What will happen to the generation of companies that raised too much with no product-market fit?
  • How will the mass layoffs in the valley change the valley as it is today?
  • Does Sujay agree that millennials are the worst segment to hire from? Are they entitled?

Jaksot(1407)

20VC: Enterprises Will Not Adopt AI without Forward-Deployed Engineers | Who Wins the Data Labelling Race: How Does it Shake Out? | How Synthetic Data Threatens the Future of Human-Generated Data with Matt Fitzpatrick, CEO of Invisible Technologies

20VC: Enterprises Will Not Adopt AI without Forward-Deployed Engineers | Who Wins the Data Labelling Race: How Does it Shake Out? | How Synthetic Data Threatens the Future of Human-Generated Data with Matt Fitzpatrick, CEO of Invisible Technologies

Matt Fitzpatrick is the CEO of Invisible Technologies, leading the company's mission to make AI work. Since joining as CEO in January 2025, he has raised $100M and accelerated AI adoption across industries from sports to consumer and government. Previously, Matt was a Senior Partner at McKinsey, where he led QuantumBlack Labs, the firm's AI R&D and software development arm. AGENDA: 04:40 Interview with Matt Fitzpatrick: Career Journey and Leadership 09:35 The Single Biggest Barriers to Enterprises Adopting AI 15:26 It is BS That Enterprises Can Adopt AI Without Forward-Deployed Engineers 28:05 Are AI Talent Marketplaces Dead? What is the best model? 46:33 How Does the Data Labelling Market Shake Out: Who Wins/ Who Loses 48:27 Are Revenue Numbers for Data Labelling Real Revenue? Or GMV? 51:20 Best Capital Allocation Decision? What did Matt Learn from it? 53:19 How Important is Brand for AI Companies Selling Into Enterprise? 01:05:59 Remote Work vs. In-Person Collaboration 01:17:06 What Does No-One Know About the Future of AI That Everyone Should Know

31 Joulu 20251h 23min

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions for 2026: Top Performing Tech Stocks of the Year 35:25 B2B Stocks to Watch 38:31 Why Salesforce Could Be the Buy of 2026 47:11 Google, Meta, Apple, NVIDIA, Microsoft: Buy One, Short One 55:38 IPO Speculations: Who Will Go Public in 2026 01:00:57 The Impact of AI on Employment

22 Joulu 20251h 9min

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a decade building consumer brands with collaborators such as Microsoft and Ferrari. AGENDA: 00:00 – Why Most "Great Products" Fail to Create Emotion 03:00 – How Perfume Taught Me Everything About Desire & Product 06:10 – The Brutal Reality of Building Physical vs Digital Products 16:00 – Why "Simple Design" Is Overrated and Dangerous 23:00 – Why Vuori is the Brand to Short in Consumer  28:30 – The Biggest Product Mistake: Listening to Customers Too Much 32:10 – On Only Do Tennis Because of Roger Federer 38:30 – Were We Too Late to Marathon Running? A Painful Admission 43:40 – The Most Controversial Product On Has Ever Launched 49:00 – Are Counterfeits Good or Bad in Fashion?

19 Joulu 202556min

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It Means 23:19 Oracle Hit Hard: Is Now the Time to Buy 28:34 Broadcom's Market Cap Drop and Anthropic's AI Chip Orders 35:04 Cursor Competes with Figma: The Convergence of Design and Coding Tools 46:20 The Biggest Danger for Incumbents: Being Maimed by AI 55:28 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:00:24 Will SpaceX IPO at $1.5TRN and The Elon Option Value

18 Joulu 20251h 22min

20VC: a16z's David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z

20VC: a16z's David George on How $BN Funds Can 5×, Do Margins & Revenue Matter in AI & the Most Controversial Bet at a16z

David George is a General Partner at Andreessen Horowitz, where he leads the firm's Growth investing team. His team has backed many of the defining companies of this era, including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI, and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge. AGENDA: 03:05 – Why Everyone is Wrong: Mega Funds Does Not Reduce Returns 10:40 – Is Public Market Capital Actually Cheaper Than Private Capital? 18:55 – The Biggest Advantage of Staying Private for Longer 23:30 – The #1 Investing Rule for a16z: Always Invest in the Founder's Strength of Strengths 31:20 – Why Fear of Theoretical Competition Makes Investors Miss Great Companies 35:10 – Does Revenue Matter as Much in a World of AI? 44:10 – Does Kingmaking Still Exist in Venture Capital Today? 49:20 – Do Margins Matter Less Than Ever in an AI-First World? 53:50 – My Biggest Miss: Anthropic and What I Learn From it?  56:30 – Has OpenAI Won Consumer AI? Will Anthropic Win Enterprise? 59:45 – The Most Controversial Decision in Andreessen Horowitz History 1:01:30 – Why Did You Invest $300M into Adam Neumann and Flow?

15 Joulu 20251h 6min

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Raaz Herberg is the Chief Marketing Officer and VP Product Strategy at Wiz, the fastest-growing cloud security company in history. As one of the first 10 employees, Raaz has helped scale the business from nothing to a multi-billion-dollar ARR business. Before Wiz, Raaz was a Senior PM working on Azure at Microsoft.  AGENDA: 03:51 What No One Knows About The Early Wiz Days 09:08 Most Effective Marketing Wiz Ever Did? Lessons from it? 24:11 How Wiz Mastered Enterprise Sales and Product Development 39:12 The Value of Proof of Concept an Why Everyone Gets Them Wrong 44:23 Why The Best Leaders Give More Equity Than They Should 52:55 The Impact of COVID on Business Operations 01:01:33 What in AI is No One Talking About That Everyone Should Be? 01:07:29 Why Does Raaz Think Custom Tools Will Dominate the Enterprise?

12 Joulu 20251h 16min

20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

AGENDA: 03:46 SpaceX's $800 Billion Valuation: A Deep Dive 09:18 IPO Market Predictions for 2026 18:18 Netflix's Bold Move: Acquiring Warner Brothers 27:43 Tiger's New Fund Strategy 33:02 Databricks' Head of AI $500 Million Seed Round 36:38 Harvey Raises $160M at an $8BN Valuation 48:22 Will LLMs Kill the App Layer 01:02:02 Google's AI Capabilities 01:06:58 Chinese Open Source Models in US Startups 01:08:57 Airwallex Raises $330M at an $8BN Valuation 01:23:50 Prediction Markets and Insider Trading

11 Joulu 20251h 31min

20VC: Kalshi's $1BN Raise, the Polymarket Feud, and the Battle to Replace Traditional Media

20VC: Kalshi's $1BN Raise, the Polymarket Feud, and the Battle to Replace Traditional Media

Tarek Mansour is the Co-Founder and CEO @ Kalshi, the leader in the world of prediction markets. Just last week, they announced their $1BN raise at an $11BN valuation. In total, they have raised $1.59BN from some of the best, including Sequoia, a16z, General Catalyst, IVP, Meritech, and more. They also last week announced exclusive partnerships with CNN and CNBC, marking their move into mainstream media and news.  AGENDA: 03:28 Why Did Kalshi Need to Raise $1BN 10:35 Why is Kalshi vs Polymarket Such a Fierce Rivalry? 20:44 The Future of Prediction Markets 25:09 Why Does Kalshi Partner with CNN When They Could Replace Them? 26:27 Why Did Tarek Fight For the Rights of his Early Investors So Much? 27:25 What Makes Alfred Lin The Best? 29:19 Does Having Sequoia as an Investor Change the Game? 36:58 Are Teenage Founders Today Emotionally Ready to Lead Companies 38:30 Quick Fire Round: Celebrity Investors, Relationships with Parents

8 Joulu 202547min

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