Invest Like the Best with Patrick O'Shaughnessy
Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464]
24 Mar 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What is the main topic discussed in this episode?
Most software companies try to maximize your time on their app to juice engagement. Ramp does the exact opposite.
Chapter 2: What insights does Mitchell Green share about cold calling 10,000 companies?
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 85% of expense reviews with 99% accuracy.
Chapter 3: How is Lead Edge Capital structured to achieve consistent investment returns?
And since Ramp saves companies 5%, 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 busy work, check out ramp.com slash invest. 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 runs end-to-end and produces real outputs the way the best people do. Auditable spreadsheets, investment memos, diligence materials, and slide decks that match your standards. This all comes from the fact that Rogo is built by finance professionals for finance professionals. and it's already being adopted by some of the most demanding institutions in the world.
Chapter 4: What criteria does Lead Edge use to evaluate potential investments?
To learn more, visit rogo.ai slash invest. OpenAI, Cursor, Anthropic, Perplexity, and Vercel all have something in common. They all use WorkOS.
Chapter 5: What opportunities exist in enterprise software according to Mitchell Green?
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 WorkOS comes in. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS 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 WorkOS.
WorkOS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit WorkOS.com to get started. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best.
Chapter 6: How does Lead Edge Capital build relationships with entrepreneurs?
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus along with all of our podcasts at colossus.com.
To learn more, visit psum.vc.
Chapter 7: What is Lead Edge's unique culture and how does it impact performance?
My guest today is Mitchell Green, the founder of Lead Edge Capital. When I think about Lead Edge, I sort of think about this giant money machine that Mitchell and his two partners have designed over the last 15 plus years to make remarkably consistent investment returns for their clients.
They have all sorts of unique aspects to the machine that they built, whether that's their collection of LPs, their eight point criteria for how they select companies, the way they do cold calls, the way they construct their portfolio. This is just a totally different way of approaching markets. They're trying to hit singles and doubles and deliver very consistent returns.
Mitchell says it's really important in life to be memorable. That's just a great simple thing that you can do.
Chapter 8: How does AI influence investment strategies and decision-making?
I think you'll find listening to Mitchell today and him talk about his entire machine and the firm that he's built, that he himself is extremely memorable. I hope you enjoy learning about his business. So the first time that I heard about Lead Edge Capital was the very famous list of what companies report, starting with cash profits.
And then if they don't have cash profits and you go down this very funny list. Hierarchy of bullshit. And the bottom one is the place that's voted the best place to work in New York City or something. Absolutely. Where did that list come from?
Why did you put that together? We've always found that the best way to communicate with our audiences, which is entrepreneurs, is to and also our LPs, our clients effectively, is to like write a quarter letter about a different topic. And I started my career cold calling companies and that's the way we source deals.
But when you start your career talking to, I think Brian and I probably spoke to like 10,000 companies. And if you want to know it's a good company, just call 10,000. Call 10,000 of them. You'll figure it out really quick. It's pretty good pattern recognition. Until our head of PR comms came in a few years ago, we had actually never posted any of these things online.
We joked that we sent this letter to some people in the VC community, one of which is like our buddy, then Jason Horowitz. And they posted it for us. We just thought, I think it's like a... Very simple way, like in a world where people spout off total bullshit all the time and like you see everything in decks. This is just a good way to distill it.
Talk to me about the 10,000 calls. What did you learn calling that many companies?
You learn to be very disciplined, actually, and you learn that most things are actually just noise, and to figure out what makes a lead-edge company, and then try to ignore everything else. You learn a lot about responsiveness of people, and more responsive CEOs tend to be better CEOs.
I think another thing you learn that's really important for young people, if you tell an entrepreneur that you're gonna actually do something, then actually do it. I think that's actually true of life. There are so many people that say they'll do things, they just never do them. And so if you're known as a firm and a person that actually does what you say you're gonna do, it goes a long way.
So if you tell an entrepreneur, hey, I know somebody at, Adobe, do you want an intro? Because it looks like it could be helpful for your business. And then he or she says, I'd love to. Well, then guess what? Follow up with that.
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