20VC: Turning $16.5M into $2.1BN; Lessons from the Greatest Venture Investment in European History: UiPath | Why VC is Not Being Commoditised | Why Price Does Not Matter | Lessons on Loss Ratio, Selling and Signalling with Cem Sertoglu

20VC: Turning $16.5M into $2.1BN; Lessons from the Greatest Venture Investment in European History: UiPath | Why VC is Not Being Commoditised | Why Price Does Not Matter | Lessons on Loss Ratio, Selling and Signalling with Cem Sertoglu

Cem Sertoglu is one of the great venture investors of the last decade. Cem is famed for writing the first check into UiPath and over several rounds turning $16.5M into $2.1BN. Cem recently started Bek Ventures, a $250M fund that was 3x oversubscribed.

In Today's Show with Cem Sertoglu We Discuss:

1. Has Venture Capital Been Commoditised:

  • Why does Cem believe that VC has not been commoditised?

  • Why does Cem believe many VCs today are not even VCs anymore?

  • How does Cem advise founders who have offers from large multi-stage firms? What questions should they ask them pre-working with them?

  • How do the best founders select the VC they choose to work with?

2. Price, Reserves, Loss Ratios:

  • Why does Cem believe that price does not matter?

  • How does Cem approach reserves and reserves management?

  • What does Cem know now about reserves that he wishes he had known when he started investing?

  • Does Cem care about loss ratio? Does he do scenario planning when making investments?

3. Making $2.1BN on UiPath:

  • How did Cem meet Daniel for the first time? Was it obvious he was incredible?

  • Why did they only write a $1M check and not take the whole round with $1.5M?

  • Why did 40 of the best investors in Europe all turn down UiPath for the Series A?

  • What did doing the bridge round for UiPath teach Cem about reserves?

  • When was it obvious UiPath was going to be a mega hit?

  • How did they continue to concentrate capital with each round?

  • When did they first start to sell shares in UiPath?

  • What was their approach to the selldown of their position?

  • When the company IPO'd, how much of it did they have?

4. AMA with One of Europe's Best:

  • Does signalling exist? How does Cem advise founders on this?

  • What has been his biggest loss? How did that change his mindset?

  • What has been Cem's biggest miss? What did he not see?

  • Why does Cem always believe you should manufacture arguments with founders before investing?

  • Why does Cem believe a high GP commit can actually misalign the GP and the LP?

Episoder(1395)

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 Des 1h 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 Des 1h 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 Des 1h 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 Des 47min

20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behind Evernote's product machine. Today that changes with Federico Simionato joining 20Product. Fede has been a Product Lead at Bending Spoons for 8 years where he has led product teams at Evernote, WeTransfer and more.   AGENDA: 03:02 From Dentist Games to $11BN Bending Spoons 04:54 Advice for Aspiring Product Managers 05:38 Building a Coveted Brand at Bending Spoons 07:43 Evaluating and Testing New Product Ideas 13:35 How Evernote has Mastered User Retention 25:24 The Impact of AI on Product Design and Prototyping 31:19 How Bending Spoons Does Product Launches and Lessons Learned 33:27 How Every Product Team Should Do Monthly Updates to Users 36:38 Recording and Transparency in Updates 38:06 Lessons from Failed Product Launches 45:14 Structuring Teams and Acquisitions 47:12 Monetization Strategies and Push Notifications 57:21 Quick Fire Round: Insights and Reflections

5 Des 1h 5min

20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software

20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software

AGENDA: 04:20 Thrive and OpenAI Partnership  07:14 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 17:39 Eventbrite Acquired by Bending Spoons for $500M 21:39 Pagerduty's $1BN Market Cap, Just 2x Revenue 26:59 The TAM Trap: Why SaaS Is Like Japan 37:42 Lessons from Companies Hitting $100M ARR 44:57 The Future of Labour Markets is F****** 52:10 The Importance of Compounding in Investments 56:45 The Relevance Game in Venture Capital 01:05:01 Supabase at $5BN or Lovable at $6BN: Which One?

4 Des 1h 12min

20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

Jonathan Siddharth is Founder and CEO of Turing, one of the fastest-growing AI companies advancing frontier models. Jonathan has led the company to an astonishing $300M ARR with just $225M raised and a profitable company. A Stanford-trained AI scientist, Jonathan previously helped pioneer natural language search at Powerset, which was acquired by Microsoft. AGENDA: 03:35 Data, Compute, Algorithms: What is Most Abundant? What is Lacking Most? 09:18 What Does No One Know About AI's Data Requirements That Everyone Should? 17:05 The Biggest Challenges Enterprises Have with AI Adoption 20:38 Why Will 99% of Knowledge Work Will be Gone in 10 Years 27:12 How Will Data-Driven Feedback Loops Replace Technology as the Moat 36:08 Who Wins the Data Labelling Market? Who Loses? 38:23 Is Revenue BS in Data Labelling? Are Players Calling GMV Revenue?  45:20 Why is SaaS Dead in a World of AI? 51:23 Will the Phone be the Primary User Interface to an AI World? 57:07 Quickfire Round

1 Des 1h 8min

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped scale BladeLogic from a startup into a public company — ultimately leading to its ~$880M sale to BMC — and drove GeoTel into a multi-billion dollar acquisition. Today he sits on the boards of top names such as Snowflake and MongoDB, while also mentoring and influencing a who's-who of modern SaaS sales leaders. AGENDA: 03:33 The Art and Science of Sales: Insights from a Veteran 04:29 Adapting Sales Strategies in the Age of AI and PLG 07:47 The Ultimate Framework to do Deal Qualification 14:13 How to Drive Urgency and Maintain Sales Process 20:06 How to Hire the Best Sales Reps 25:11 Step-by-Step Guide to Training Sales Reps 45:22 The Mindset of the Best Sales Reps 54:55 Single Most Important Skill to Win in Sales

28 Nov 1h 8min

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