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: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI

20VC: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI

AGENDA: 03:44 Rory Is So Old He Worked with Arthur Rock!!! 07:28 Goldman Sachs Acquires Industry Ventures for $665M 16:37 Thinking Machines Co-Founder Raises $2BN and Then Leaves for Meta 29:36 SoftBank Goes for $5BN Leverage Against ARM Stock To Buy More OpenAI 39:35 More Data Centres Than Offices: Are We In a Bubble 43:28 Where is the Alpha in Venture in 2025 51:48 What 90% of Managers Get Wrong About Portfolio Management

16 Okt 1h 19min

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams. AGENDA: 00:00 Why Unreasonable Men Win in Startups 07:22 How to Make Co-CEOs Work 13:22 Are We in an AI Bubble? Is Everything Overvalued? 26:46 The Future of Software Development: More or Less Devs 32:53 Do Margins Matter in a World of AI 34:02 The Future of Vibe Coding… 36:35 Does Defensibility Exist in a World of AI 42:09 Is Per Seat Pricing Dead in a World of AI 49:01 The Founder Journey and Leadership 54:28 Quick Fire Round: Parenting Advice, Relationship to Money

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20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

Chris Degnan is the former Chief Revenue Officer at Snowflake, where he was instrumental in scaling the company from less than $1M in ARR to over $3B in annual revenue. He joined as the first sales hires and built Snowflake's go-to-market engine from scratch, growing the team from to more than 6,000 globally. Under his leadership, Snowflake became one of the fastest-growing enterprise software companies in history, achieving a record-breaking IPO in 2020. AGENDA: 04:34 How to Build a Sales Team from Scratch 07:49 How to Hire and Evaluate Sales Leaders 15:23 Four Big Lessons Scaling Snowflake to $3BN ARR 31:30 Comparing Snowflake and Databricks: What Databricks Did Better? 35:26 How to Manage Sales Team Morale in Competitive Markets 43:53 Why Customer Success is BS and What To Do With It 48:31 How Every Sales Leader Needs to Change in An AI World 49:37 Biggest Reflections on Sales Leadership 54:38 Quick Fire Questions and Final Thoughts 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

10 Okt 1h 2min

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

20VC: OpenAI's Multi $BN Deal with AMD | Polymarket, Vercel and Supabase Raise Mega Rounds | Does King Making Really Work in Venture Capital: Harvey vs Legora | Chamath is Back: The SPAC is Back

AGENDA: 03:29 OpenAI and AMD's Major Partnership 07:35 Microsoft Have F***** Up the OpenAI Partnership 17:08 OpenAI's Developer Day Announcements 20:45 Why VC is the Most Forgiving Asset Class on Price and Valuation 29:10 What Does it Take to IPO in 2025: Why Snyk Will Not IPO 42:30 Four Strategies Companies Need to Take to Own Their Own Destiny 49:31 Vercel Raises $300M at $9BN: Suicide Round or Strategic 55:39 Does King Making Really Work in Venture Capital: Legora vs Harvey 01:08:11 Chamath Raises Latest SPAC: SPACs are Back 01:10:56 Polymarket Raises $2BN at a $9BN Valuation 01:14:53 Quick Fire Questions and Wrap-Up

9 Okt 1h 24min

20VC: Cerebras CEO on Why Raise $1BN and Delay the IPO | NVIDIA Showing Signs They Are Worried About Growth | Concentration of Value in Mag7: Will the AI Train Come to a Halt | Can the US Supply the Energy for AI with Andrew Feldman

20VC: Cerebras CEO on Why Raise $1BN and Delay the IPO | NVIDIA Showing Signs They Are Worried About Growth | Concentration of Value in Mag7: Will the AI Train Come to a Halt | Can the US Supply the Energy for AI with Andrew Feldman

Andrew Feldman is Co-Founder & CEO of Cerebras, building the world's fastest AI inference and training. Cerebras recently closed a $1.1BN Series G round at an $8.1 billion valuation, backed by top names including Fidelity, Atreides, Tiger Global, Valor Equity and 1789 Capital. Under his leadership, they've leapfrogged GPU limits in inference, operate at trillions of tokens per month, and are filing to go public soon. AGENDA: 02:43 Why We Did Not IPO and Raised $1BN From Fidelity 05:03 Analysis of Chip and Compute Landscape Today 07:14 NVIDIA Showing Signs They Are Running Out of Ideas 13:57 The Real Questions to Ask on Chip Depreciation 24:54 Energy Requirements for AI: Is it Feasible? 29:25 Mag7 Value Concentration: Feature or a Bug 31:57 Talent is the Bottleneck and Trump Makes it Worse 32:55 The War for Talent: Secrets No One Sees 34:22 Evaluating the Data Centre Economy: Many Will Lose Money 38:01 Three Changes the US Could Make to Beat China in AI 42:30 Why 80% of our Revenues are in the UAE 47:26 Quick Fire Questions 58:59 Why Work Life Balance is Total BS

6 Okt 1h 4min

20Growth: How to Use Influencers to Scale Growth Insanely Fast | How to Optimise User Onboaring for Growth | How the Best Growth Teams Create Organic Growth and Community | Why LTV/CAC Models are BS with Ketty Slonimsky

20Growth: How to Use Influencers to Scale Growth Insanely Fast | How to Optimise User Onboaring for Growth | How the Best Growth Teams Create Organic Growth and Community | Why LTV/CAC Models are BS with Ketty Slonimsky

Ketty Slonimsky is Chief Growth Officer at Palta, the platform behind apps like Flo (the #1 female health app with 77M+ MAU), Simple, and Zing AI, where she leads a centralized growth function across the portfolio. She was previously first VP Product & Growth at HeliosX (£900M+ ARR, bootstrapped D2C healthtech), has advised companies like SonderMind, Runna, Guardio, Cheddar, P&G Digital Ventures, and is a board advisor at HeliosX. AGENDA: 02:33 What is Growth and When to Hire For It 06:04 Three Profiles of Successful Growth Leaders 10:07 Challenges and Learnings from Failed Ventures 21:17 How to Optimise User Onboarding for Growth 26:14 Biggest Lessons on Retention 30:25 How to Artificially Create Organic Growth and Community Building 32:10 Why LTV Models are BS 37:35 How to Use Influencers to Grow Insanely Fast 47:07 The Metrics that Matter in Growth 49:48 Push Notifications and Engagement: What To Do vs What Not to Do? 51:57 Quick Fire Round

3 Okt 1h

20VC: Are Burn Multiples BS in an AI World | Sam Altman Needs $1TRN of Energy | Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? | FiveTran and DBT: Is the Wave of Consolidation About to Begin?

20VC: Are Burn Multiples BS in an AI World | Sam Altman Needs $1TRN of Energy | Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? | FiveTran and DBT: Is the Wave of Consolidation About to Begin?

AGENDA: 03:58 Understanding Burn Multiples and Capital Efficiency in an AI World 11:54 What Metrics Founders Need to Focus on in a World of AI 19:31 The Role of Kingmakers in Venture Capital: Harvey, Abridge, Profound 33:42 Klarna, Figma, Stubhub, all Down: Are Public Markets Turning? 36:35 OpenAI Needs the Same Energy as Japan… WTF! 41:09 How Can We Fund the $1TRN Sam Altman Needs for Energy 52:39 FiveTran and DBT: Is the Wave of Consolidation About to Begin? 59:44 Does Private Equity Need to Change in a World of AI 01:06:23 Political Expression and Corporate Responsibility

2 Okt 1h 16min

20VC: OpenAI and Anthropic Will Build Their Own Chips | NVIDIA Will Be Worth $10TRN | How to Solve the Energy Required for AI... Nuclear | Why China is Behind the US in the Race for AGI with Jonathan Ross, Groq Founder

20VC: OpenAI and Anthropic Will Build Their Own Chips | NVIDIA Will Be Worth $10TRN | How to Solve the Energy Required for AI... Nuclear | Why China is Behind the US in the Race for AGI with Jonathan Ross, Groq Founder

Jonathan Ross is the Founder & CEO of Groq, the AI chip company redefining inference at scale. Under his leadership, Groq has raised over $3B from top investors. The company has reached a valuation of nearly $7B, positioning itself as one of NVIDIA's most formidable challengers. Previously at Google, Jonathan led the team that built the first Tensor Processing Unit (TPU), making him one of the leading architects of modern AI hardware. AGENDA: 00:00 The Future of AI and Compute 05:07 Why the Hyperscalers Have to Keep Spending Recklessly on AI 12:49 Why OpenAI and Anthropic Will Have to Build Their Own Chips 19:47 OpenAI and Anthropic Will be $5BN Companies: The Bull Case 29:50 Why China is Behind the US in AI and Deepseek is More Expensive to Run 33:55 How Europe Could Compete in AI and Why the US is More Risk Averse Than Europe 42:51 Why AI Will Lead to Too Many Not Too Few Jobs 43:19 Deflationary Pressures and New Job Markets 45:51 The Future of Vibe Coding 47:14 Why AI Companies Should Strive to Have Low Margins 49:31 Why We Have to Have Nuclear Energy and How to Bring it Back 56:55 How Permits are Ruining the Potential of AI 01:03:58 Why OpenAI and Anthropic are so Undervalued 01:16:53 Quickfire: Biggest Fear, Nvidia: $10TRN, Zuck Buying AI: Work or Not

29 Sep 1h 21min

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