20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding

20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding

Semil Shah is the founder of Haystack, an early stage investment firm now investing out of it's third fund, with previous investments being Instacart, DoorDash, Managed by Q. In the past he has also been a consultant to some of the leading funds in the valley including the likes of Kleiner Perkins, DFJ, General Catalyst and more. If that was not enough, Shah also has an extensive career in media having been a contributor for both TechCrunch and the Harvard Business Review in the past. Due to all of this Shah was listed by Marc Andreesen as one of his '55 Unknown Rockstars in Tech'.

In Today's Episode You Will Learn:

1.) How Semil made his way into VC? How did he come to create Haystack?

2.) What were the challenges and concerns for Semil in raising and establishing his own fund?

3.) Question from Michelle Tandler: How does Semil send deals through to Series A? What is his 'cool' process? What are the commonalities of those that make it to Series A and those that do not?

4.) How has Semil approached the aspect of personal VC branding? How does he evaluate the rise of the personal VC brand in the last few years?

5.) Why does Semil believe he is not 'founder friendly' in the conventional sense?

Items Mentioned In Today's Show:

Semil's Fave Book: Burmese Days by George Orwell

Semil's Most Recent Investment: AquaCloud

As always you can follow The Twenty Minute VC, Harry and Semil on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Snapchat here! This episode was brought to you by DesignCrowd, the online marketplace for custom graphic, logo and web design that helps startups, entrepreneurs, web developers and agencies outsource design projects to designers from around the world. How Does It Work? Once you have launched your brief, designers will begin submitting quality designs for you to review. With some constructive feedback, you can quickly generate a large gallery of designs that really do fit your needs. You can have exactly what you need within just three days. Once you have selected your favourite design, you will be sent all the files you require to update your branding. If you don't like any of the submitted designs, then DesignCrowd offers a money back guarantee. So checkout designcrowd.com/VC and enter the promo code VC100 to get an astonishing $100 off your next project.

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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

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 Dec 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 Dec 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 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

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

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 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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