Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]
Invest Like the Best with Patrick O'Shaughnessy
Colossus
4.7 • 2.5K Ratings
🗓️ 29 January 2026
⏱️ 79 minutes
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| 0:00.0 | Here's an interesting question to think about. If your finance team suddenly had an extra week every month, what would you have them work on? |
| 0:05.9 | Most CFOs don't know because their finance teams are grinding it out on lost expense reports, invoice coding, and tracking down receipts until the last possible minute. |
| 0:13.7 | That's exactly the problem that Ramps set out to solve. Looking at the parts of finance, everyone quietly hates and asking why are humans doing any of this? |
| 0:21.7 | Turns out they don't need to. Ramp's AI handles 85% of expense reviews automatically with 99% |
| 0:27.8 | accuracy, which means your finance team stops being the department that processes stuff and starts |
| 0:32.6 | being the team that thinks about stuff. Here's the real shift. Companies using Ramp aren't just |
| 0:37.1 | saving time. They're reallocating it. While competitors spend two weeks closing their books, you're already planning next quarter. While they're cleaning up spreadsheets, you're thinking about new pricing strategy, new markets, and where the next dollar of ROI comes from. That difference compounds. Go to ramp.com slash invest to try ramp and see how much leverage your team gains when the |
| 0:55.9 | work you have to do stops getting in the way of the work that you want to do. Investing is hard. |
| 1:00.1 | It's an apprenticeship industry with messy data, complicated workflows, and decisions that demand |
| 1:04.1 | judgment. Investing needs specialized AI, and that's why I'm so excited about Rogo. Rogo is an AI platform |
| 1:10.4 | purpose-filled for Wall Street, not a generic chatbot, but a suite of |
| 1:13.5 | agents designed around how bankers and investors actually work, from sourcing, diligence, and |
| 1:17.9 | modeling to turning analysis into deliverables. Finance requires deep domain expertise far |
| 1:22.9 | beyond your average chatbot. As listeners of this podcast know, every investment firm is unique, |
| 1:27.4 | with its own thesis, internal notes, templates, and ways of investing. Generic AI can be impressive, but it doesn't actually understand your process, and that's where the advantage lives. For me, three things set Rogo apart. One, it connects directly to your system, so it can work with your actual data, internal, and external. Two, it understands your workflows, how work really happens across a deal or an investment. And three, it runs end to end and produces |
| 1:48.4 | real outputs in the way that your best people do, auditable spreadsheets, investment memos, |
| 1:53.0 | diligence materials, and slide decks that match your standards. Rogo is built by a deeply |
| 1:57.4 | technical AI team with real finance DNA, large language models for finance |
| 2:01.6 | professionals by finance professionals, and it's already being adopted by some of the most |
| 2:05.4 | demanding institutions in the world. The teams that get this right early won't just move faster, |
| 2:09.9 | they'll compound better decisions, train their own AI analyst, and the gap will widen. |
| 2:14.2 | The Rogo team's vision is distinct, make the most ambitious investors even better, |
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