Gokul Rajaram: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI

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. Prior to Marathon (his firm), Gokul served on the executive team at DoorDash and Block. Before Block, he served as Product Director of Ads at Facebook. Earlier in his career, Gokul served as a Product Management Director for Google AdSense. Gokul is also a prolific angel investor, having invested in 700+ companies, including Airtable, Figma, Groq, Runway, Supabase, and Vercel.

In Today's Show We Discuss:

• Investing Lessons from Google, Doordash and Facebook

• Why Every Company Today Needs to be Multi-Product

• The SaaS Apocalypse: Is the Entire Sector Going to Zero?

• The 8 Moats of Enduring Software Companies: How to Analyse Companies

• Salesforce vs. Atlassian: Which Systems of Record are Dying?

• Outcome-Based Pricing: Is This the Total Death of Seat Pricing?

• The Bolt-On AI Trap: Why Rebuilding Your Entire UX is Non-Negotiable

• Are the Outcome Sizes of Vertical SaaS Large Enough for VC Today?

• The Zombie Cohort: What Happens to Private Companies with High Valuations?

• Is "King Making" Complete Bullshit?

• Durability Over Margins: What Really Matters in a 100x Growth World

• The Non-Consumption Miracle: Why Granola and Gamma are Crushing It

• The PayPal Rule: Can You Raise Prices 5 Times in 3 Years?

• My Biggest Miss: How I Misread the Shopify Billion-Dollar Mark

• The Courage to Bet: Why Instacart is the Best VC Deal Ever

• Does "Proprietary Founder Access" Even Exist?

• Double Down or Diversify? The Truth About Fund Reserves

• The Vanta Anti-Portfolio: A Mistake I'll Never Forget

• When to Sell: The "Sell a Third, Hold a Third, Trade a Third" Rule

• Why Remote Early-Stage Companies are Dying

• Why Mid-Level Partners are Fleeing Mega Funds