Invest Like the Best with Patrick O'Shaughnessy
Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
20 Jan 2026
Chapter 1: What is discussed at the start of this section?
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? 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. That's exactly the problem that Ramp set out to solve.
Looking at the parts of finance, everyone quietly hates and asking why are humans doing any of this? Turns out they don't need to. Ramp's AI handles 85% of expense reviews automatically with 99% accuracy. which means your finance team stops being the department that processes stuff and starts being the team that thinks about stuff. Here's the real shift.
Companies using ramp aren't just 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 work you have to do stops getting in the way of the work that you want to do. Investing is hard. It's an apprenticeship industry with messy data, complicated workflows, and decisions that demand judgment. Investing needs specialized AI, and that's why I'm so excited about Rogo.
Rogo is an AI platform purpose-built for Wall Street, not a generic chatbot, but a suite of agents designed around how bankers and investors actually work, from sourcing, diligence, and modeling, to turning analysis into deliverables. Finance requires deep domain expertise far beyond your average chatbot.
As listeners of this podcast know, every investment firm is unique, with its own thesis, internal notes, templates, and ways of investing.
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Chapter 2: How does Ramp's AI technology improve finance team efficiency?
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 real outputs in the way that your best people do. Auditable spreadsheets, investment memos, diligence materials, and slide decks that match your standards. Rogo is built by a deeply technical AI team with real finance DNA. Large language models for finance professionals by finance professionals.
I'm fully bought into that vision, and I think their work will fundamentally reshape investing.
Chapter 3: What is the significance of the Upanishads in shaping Patrick's worldview?
Learn more at rogo.ai slash invest. If you're a longtime listener of this show, you've heard the same pattern play out across so many great companies. The moment a product finds early traction, the constraints shift from engineering curiosity to enterprise execution. And one of the biggest hurdles, whether you're OpenAI, Cursor, Perplexity, Vercel, or a brand new startup is identity and access.
SSO, SCIM, RBAC, audit logs, these are the capabilities that give enterprises the confidence to adopt your product at scale. That's where WorkOS comes in. It's become the default way fast-growing software companies get enterprise-ready.
Instead of spending months building SSO or provisioning or permissions in-house, WorkOS gives you all the core features enterprises require through clean, modern APIs. And in the era of AI, this matters more than ever. AI-native companies scale faster than anything we saw in classic SaaS. They can't afford to wait on enterprise compliance. They need it on day zero.
That's why so many of the top AI teams you hear about already run on WorkOS. If you're building software and want to unlock larger customers or just avoid reinventing a very unglamorous wheel, head to WorkOS.com. It's the fastest way to become enterprise-ready and stay focused on what actually moves the needle your product. Visit WorkOS.com to get started. Hello and welcome everyone.
I'm Patrick O'Shaughnessy and this is Invest Like the Best. 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.
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast.
This week we have an unusual episode because I am on the other side of the mic on my friend David Senra's new show called David Senra, in which he interviews me. I've chosen for the last five or six years to never be interviewed, mostly because I love doing what I do so much, shining a light on an investor, a founder, a thinker of some type who I can learn from. But after we did the show,
I thought it would be a neat and rare opportunity to share with you all how I think about a lot of things as we build Invest Like the Best, Colossus, and Positive Sum. I really hope you enjoy this little bit different and special episode with David Senra.
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Chapter 4: How does Patrick define his organizing principle for life?
And this extends to my kids, my wife, my friends, the CEOs of companies that we've invested in, people that we have on our show that we tell the world about. That's the repeated thing that I love. And I also kind of like picking sides. I like saying I like this person. And by extension, I like them more than the other available options in this field or this industry or whatever.
And I just get tremendous joy out of that. So now I'm architecting my life to just be able to do as much of that as possible. I hope I get to do it for a long time.
I screenshotted this text. This was many years ago. Somebody was asking me, I can't remember who it was now, but they were asking me what Patrick is like. I was like, well, positive sum is definitely a way to describe him. He doesn't do things for money. That doesn't mean he's not commercial. He makes a lot of money.
He's going to continue to make a lot of money, but that's not the driver behind it. Let me go back to, one of the craziest days of my life has directly involved you, right? Like I was like in the middle of this like five and a half year struggle of like being obsessed with something I know I truly cared and thought was really good.
But the external world was like, no, like nobody gives a shit about what you're doing, David. And, you know, I kept doing it. And we have a mutual friend in Sam Hinckley who's going to keep getting annoyed because I bring him up on every podcast I go on.
He's deserving of the mentions.
The two episodes he did with you, especially the one about find your people, I think is the beautiful one. I go back to that one all the time and the notes that he says in there. And one of the things that I think about all the time which again, I'm not an investor, but I want like access and I want deep relationships with people, very high quality people.
And I, it is just like, he's like, people are power law and the best ones change everything. And so once you actually see that, you are very, almost like ruthless with who you let have access to you. And I think I've, I'm getting very ruthless and continue to be ruthless because of like what I'm, you know, kind of chasing after. But I had no followers on Twitter at all.
Just tweeting into the oblivion, no one gave a shit what I'm doing. One day, this is why it's one of the first things that I think speaks volumes about you and how you actually live your life. I think you've now leaned into this more over the last four years that we've been talking. And I'm like, see a bunch of notifications on Twitter. I'm like, I don't get notifications on Twitter.
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Chapter 5: How do relationships influence success in life and work?
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This goes back to the beneficial nature of relationships. You start out as like, okay, I had a conversation with them. And then if there's some kind of mutual respect, you build a relationship. Like right now, we're filming, this is the first podcast ever filmed at the Amman in New York.
Yeah.
You try to email the Amman in New York and ask them if they let me set up and film a podcast here for free. That's not going to happen. That happens because of the relationship, a personal relationship that I have with a friend of mine who is involved with Amman. This is why I would say relationships run the world. And our jobs are essentially like learning relationships.
and then taking what we learned and packaging it for the consumption of somebody else for an easy way for somebody else to consume and benefit from that learning, whether it's a conversation, a book review, or whatever the case is. So that's very practical. That was in the early days when you were doing Canvas, right? Yeah. What about larger things in your life? Who do you think had an impact?
My life would not be the same if not for that one conversation, that one idea with that person.
Two people came to mind right away. The first is Herb Allen from Allen & Company, who I don't know well. These lessons came from one incredibly interesting conversation about my sense of him again, don't know him well, is that he is uncompromising in his values. He's maybe like the apex predator of like the thing I wanna do, which is like picking and supporting people.
I think that's what he's done for a really long time with unbelievable success. And that he is so incredibly uncompromising about how he does that and willing, I won't tell the examples, but I think willing famously to throw away huge commercial opportunities just because the person wasn't who he wanted to support.
So sometimes it's literally a conversation with a person that just smacks you in the face and makes you feel validated maybe for what you're trying to do. There's a gentleman named Reese Duca who's very, very private and there's no content about him or interviews with him. I wish to God he would let me interview him. I know he never will.
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Chapter 6: What does it mean to be red on the color wheel?
So I could keep – I literally could rattle names. A gentleman I spend a ton of time with now named Jesse Beiruti, who I am with basically every day, who also I think has no interest in fame or accolades or recognition, but I think is one of the great – will go down, I would predict, as one of the great investors ever.
And he's like Reese, he's completely uncompromising and the most principled way of living I've ever seen. Just like refuses to get sucked into the game. And I could, God, man, I could rattle off names for hours and hours. I mean, there's so many people that have influenced me. And that's what makes this all fun. That's what makes what you and I do so fun is I'm inspired constantly.
And you're doing this new show. I interview people once a week, but really I interview like 10 people a day. That's what I do. I just happen to have mics there one of the times. If I'm doing it 40 or 50 times a week, which is not an exaggeration, it really is that many people every week. Just like, who are you? What's your deal? I love doing that.
And so there's just too many to name, but those are a couple that came to mind.
Munger said, I'm paraphrasing, but he's like, one of the best ways to learn is you find somebody that's an outlier and you just ask, what the hell is going on with this person? Yeah. You just keep asking that question to try to get deeper and deeper and deeper, but reverse engineer of what they're doing and why they're really successful.
There's another fascinating thing where there's this meme where it's like, everybody has a podcast now, and everybody starts podcasts. And as soon as that takes hold, you've been doing podcasting for 10 years, and you decide, no, I'm going to go in a different direction.
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Chapter 7: What role does kindness play in shaping our lives?
And the majority of our conversations, I would say, now are not even about the podcast. They're about these profiles that you're writing about. on Colossus. Some of them have been so incredible that I actually used them as source material for a Founders episode, which I think we should do more of those collabs because they were really well-written, kind of like doing my job for me. Yeah.
Why did you decide to do that?
I'm, in the abstract, very interested in how can I create and control valuable, scarce units of attention and then dole those things out to the people that we believe in. at a very high level, the reason we now have a magazine, which on its face, I think everyone would have agreed was a stupid idea or told me it was a stupid idea when we started it.
Why are we doing these profiles that take months or quarters or years to write and require lots of investment? Why do them? Well, the reason is I think it's just a beautiful way to shine the light beyond like podcasting on people that we admire. And to teach someone, teach the world about a compelling founder or a compelling investor or artist or whatever.
And the thing that I didn't realize was that because I'm not writing the profiles, our amazing team is writing them, it would actually be a double whammy that not only when we started doing this, I went and read David Remnick, who's the long-time editor for The New Yorker. And New Yorker profiles were always my favorite growing up, these incredibly detailed, amazing, well-written profiles.
He wrote in the introduction to this, his compilation of his favorite New Yorker profiles. There's this line that says, the best profiles over the last hundred years are defined by somebody doing a thing they're obsessed with and a writer that is as obsessed with the person as the person is with the thing. And I remember reading that paragraph and just thinking, wow, I want to read.
That's what I want to read. And, you know, so I went and I read a million profiles. And the very best one I read was in a publication called Tablet on Palmer Luckey from Andrew. And I reached out to the author. His name is Jeremy Stern. who's now the editor-in-chief at Colossus. And the rest of that story is sort of history.
He joined, we've got other people that have joined or are joining to write these profiles. And it just felt like, wow, this is another way to do the thing we love to do, which is to find the person, become obsessed, learn everything about them, take great time and pain to write a definitive thing about them, and then share it with millions of people.
And the fact, the one that we wrote about Josh Kushner and Thrive was one of these like bizarre break the internet moments when it just like completely took over the internet for a while. And I remember reading it the first time, and I was like 45 minutes into reading it, and I was still reading about the Holocaust.
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Chapter 8: How does one define their life's work?
And I thought that was the coolest, most beautiful thing. So this project has become an excuse to, first of all, find more talented people, the writers,
that we can support which is great see the potential you know same thing we've been talking about over and over again so now now team members become more people that we can do this supporting thing with and for them to write things they're obsessed with and passionate about and then for the rest of the world to benefit for the people being profiled hopefully to benefit
If we tell the honest stories and we want to tell the hard parts and the interesting parts. It's been successful beyond what I ever could have imagined. I think it's important to note when I started with the first idea, everyone said it was a stupid. I mean, literally everybody said it was a stupid idea. When I started the podcast, everyone said it was a stupid idea.
When we started Canvas, everyone said it. I think if people say something is a good idea, I always get a little nervous. Because if it sounds like a good idea, it just feels you're in a more competitive space. It's going to be harder. I think the key is stuff that sounds dumb but isn't. And I think that's what I would – starting a magazine in 2025 I think falls in that category of sounds dumb.
Magazines are dead or dying. But the thing underneath it was this desire to – have more ways to do the thing that we love to do, which is find people, learn about them, tell the world about them. I suspect it won't be long until that's much bigger than even the podcast, which itself is very, very big. The surprising thing is I think you want that to be the case. What specifically?
Colossus being bigger than the podcast. Of course. That's not an of course thing. You got to unpack that. You got to explain why you feel that way. I know you don't know how other people view you, but I get a lot of this because they know of our association. They're like, this is the best business interviewer in the world, and this is incredible.
Why would he not want that to be the biggest thing? I'm not saying I want to keep doing that. I know that. For sure. I love it. But I think in your heart, if you had to choose, you'd be like, no, I'd rather have the profiles be bigger. Because you like, again, this goes back to, I think, how we started the conversation. Like, I really do believe you'd like to be the guy behind the guy.
That's true, but the reason for me is almost so obvious that it's uninteresting, which is, well, if a bunch of other talented people are doing this and then creating these things, first of all, I'll have more of them so I can enjoy them more and I'll get to enjoy it just like everybody else. I can't tell you how fun it is to get the first draft of one of these things in Slack.
The things that make me the most giddy in my work are some new draft that they've created for Colossus and some new research report on an investment created by my incredible team on that side, who in many ways are just doing, it's turtles all the way down. It's the same like deep investigation, publishing, writing, clear thinking.
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