Gokul Rajaram - Lessons from Investing in 700 Companies
1/29/20261 hr 16 min
My guest today is Gokul Rajaram, Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods.
Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad view into how products are built and scaled.
This conversation is about how product building is changing with AI. We discuss the one thing Gokul believes is truly...
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First 90 secondsPatrick O'Shaughnessy· Host0:00
Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite. Ramp understands that no one wants to spend hours chasing receipts, reviewing expense reports, and checking for policy violations. So they built their tools to give that time back, using AI to automate eighty-five percent of expense reviews with ninety-nine percent accuracy. And since Ramp saves companies five percent, it's no wonder that Shopify runs on Ramp, Stripe runs on Ramp, and my business does, too. To see what happens when you eliminate the busywork, check out ramp.com/invest. OpenAI, Cursor, Anthropic, Perplexity, and Vercel all have something in common: they all use Work OS. And here's why. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC, and audit logs. That's where Work OS comes in. Instead of spending months building these mission-critical capabilities yourself, you can just use Work OS APIs to gain all of them on day zero. That's why so many of the top AI teams you hear about already run on Work OS. Work OS is the fastest way to become enterprise-ready and stay focused on what matters most: your product. Visit workos.com to get started. Every investor should know about Rogo, because Rogo AI's platform is not just another generic chatbot. Instead, it was designed to support how Wall Street bankers and investors actually work, from sourcing diligence and modeling to turning analysis into deliverables. For me, three key things differentiate Rogo. First, it connects directly to your system, so it can work with your actual data. Second, it understands your workflows, how work really happens across a deal or an investment. And third, it