20VC: Why You Have To Raise $100m+ If You Want To Go Big Today, The 5 Fundamentals To Starting and Scaling A Successful Marketplace & Why Female Founders Under-Promise and Over-Deliver with Paul Hsiao, Founding Partner @ Canvas Ventures

20VC: Why You Have To Raise $100m+ If You Want To Go Big Today, The 5 Fundamentals To Starting and Scaling A Successful Marketplace & Why Female Founders Under-Promise and Over-Deliver with Paul Hsiao, Founding Partner @ Canvas Ventures

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley's leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies.

In Today's Episode You Will Learn:

1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC?

2.) Question from Oren Zeev: Having been a partner at both, how does Paul compare the culture and strategy of two such differing firms of Canvas vs NEA? How does Paul's thinking on exit expectations and requirements change with the change of fund? How does a smaller fund fundamentally change the way you think about investing?

3.) What does Paul believe are the 5 fundamentals of building and scaling a successful marketplace? Why does Paul believe that it is the supply side that tells you if your marketplace is or is not working? Why does Paul believe stubbornness is good in marketplace founders?

4.) Why does Paul believe that raising $100m is critical for new companies if they want to go big? What does this mean for capital efficiency? What does this mean for ownership with multiple dilutive rounds impacting investor returns? How should founders then think about winning the "capital arms race"? What are the exceptions to these rules?

5.) Female founders receive 2.19% of VC funding, however, Paul has many more female founders in portfolio than the industry. Why does Paul think this is? What would Paul like to see change in the distribution of VC funds? What is the required steps to make this happen?

Items Mentioned In Today's Show:

Paul's Fave Book: The Innovator's Dilemma

Paul's Most Recent Investment: Thrive Global, Roofstock

As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

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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

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

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15 Dec 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 Dec 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 Dec 20251h 31min

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

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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 Dec 202547min

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 Dec 20251h 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?

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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

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