20VC: Biggest Lessons from Working with John Doerr, How Founders Can Have Discussions of Vulnerability with Their Board and Investors & Marrying Another Founder; The Pros, Cons and Ways To Make it Succeed with Alyson Friedensohn, Co-Founder & CEO @ Modern

20VC: Biggest Lessons from Working with John Doerr, How Founders Can Have Discussions of Vulnerability with Their Board and Investors & Marrying Another Founder; The Pros, Cons and Ways To Make it Succeed with Alyson Friedensohn, Co-Founder & CEO @ Modern

Alyson Friedensohn is the Founder & CEO @ Modern Health, a one-stop solution for employee mental well-being through evidence-based support and digital content. To date, Alyson has raised over $45M in funding from some of the best in the business including Kleiner Perkins, Founders Fund, John Doerr, 01 Advisors and Katrina Lake to name a few. Prior to founding Modern Health, Alyson was a Product Partner for Operations at Collective Health and before that was an operations manager @ Keas (acquired by Welltok).

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In Today's Episode You Will Learn:

1.) How Alyson made her way into the world of startups and came to change how we think about mental health with Modern Health?

2.) How does Alyson think about and assess her own psychology? How does Alyson deal with crisis modes? What works? What does not? What is the driver for Alyson to get her through the very toughest of times? How does Alyson approach her own attitude to risk?

3.) What is Alyson's biggest pieces of advice for non-technical founders? What are the biggest challenges Alyson has had to overcome as a non-technical founder? How did she do it? How did Alyson strategically invest in the sales process? What worked? What did not? How does Alyson think about the balance of hitting sales quota and mental health?

4.) With some of the best VCs in the world, how did Alyson approach the process of investor selection? What can VCs do to build that relationship of trust with their founders? How does multi-stage VCs investing impact whether the founder remains in a "sales process" for the next round? How does Alyson temper the weight of John Doerr's words?

5.) What have been Alyson's biggest lessons in making it work marrying another founder? What works? What is challenging? How do they as a couple think about switching off? How does Alyson advise Harry on his own love life?!

Items Mentioned In Today's Show:

Alyson's Fave Book: How to Win Friends and Influence People

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

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

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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

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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 Dec 20251h 9min

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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 Dec 202556min

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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?

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 Dec 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 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

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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

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