20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram artwork

20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

March 16, 2026

Gokul Rajaram is one of the greatest operators turned investors of the last 2 decades. He is trusted as the go to advisor for the greatest founders in the world. Today he serves as a Board Director at three public companies: Coinbase, Pinterest and The Trade Desk.
Speakers: Gokul Rajaram, Harry Stebbings
**Gokul Rajaram** (0:00)
The first mode is data mode. Second is the workflow mode. Third one is regulatory mode. Fourth mode is a distribution mode.

**Harry Stebbings** (0:07)
We're on number five.

**Gokul Rajaram** (0:08)
Ecosystem mode. Sixth one is a network mode. Seventh one is the thing you mentioned, physical infrastructure, right? And the eighth one, I would say scale mode. You cannot be a single product company. I think vertical products, you've got to really own full stack. I think it's harder otherwise to be a 10 plus billion dollar company.

**Harry Stebbings** (0:25)
This is 20VC with me, Harry Stebbings, and I'm so excited for the show today. I'm thrilled to welcome one of the best operated turned investors of the last two decades, Gokul Rajaram. He works with some of the best founders of our time, serving on the boards of three public companies, including Coinbase, Pinterest, and The Trade Desk. He's also one of the most successful angel investors of the last few decades, with early investments in Airtable, Figma, Vercel, Supabase, and many more. And now as the founder of Marathon, he's helping the next generation of great founders. He was one of the first investors in 20VC Fund One, and this is one of the best episodes we've done in a long time. But before we dive into the show today, as an investor, I'm always on the lookout for tools that really transform how I work. Tools that don't just save time, but fundamentally change how I uncover insights. That's exactly what AlphaSense does. With the acquisition of Tegas, AlphaSense is now the ultimate research platform built for professionals who need insights they can trust, fast. I've used Tegas before for company deep dives right here on the podcast. It's been an incredible resource for expert insights. But now with AlphaSense leading the way, it combines those insights with premium content, top broker research and cutting edge generative AI. The result? A platform that works like a supercharged junior analyst, delivering trusted insights and analysis on demand. AlphaSense has completely reimagined fundamental research, helping you uncover opportunities from perspectives you didn't even know how they existed. It's faster, it's smarter and it's built to give you the edge in every decision you make. To any VC listeners, don't miss your chance to try AlphaSense for free. Visit alphasense.com/twozero to unlock your trial. That's alphasense.com/twozero.
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**Gokul Rajaram** (4:29)
It's my pleasure to be here, my friend. Thank you again.

**Harry Stebbings** (4:31)
Now, I wanted to start with how some of your prior companies that you've worked out have shaped your investing mind specifically. And I wanted to start with Google. When you reflect on your time with Google, how did that shape your mindset for the types of companies that you like today?

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