Invest Like the Best with Patrick O'Shaughnessy
The Chainsmokers - Music & Markets - [Invest Like the Best, EP.430]
24 Jun 2025
Chapter 1: What is the evolution of The Chainsmokers from DJs to investors?
The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busywork. If you think about it, you become a finance leader because you love strategic work.
modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions.
Chapter 2: How do The Chainsmokers approach the creative process in music?
It's the opposite of leverage. This is exactly why I'm so bullish on what the team at Ramp has built. Kareem and Eric understood that every minute spent on manual expense management is a minute stolen from high leverage work. So they automated all of it. Automatic categorization, receipt matching, spending controls that actually work.
Check out ramp.com slash invest and see what happens when you eliminate the busy work. Cards issued by Sutton Bank, member FDIC. Terms and conditions apply. To me, Ridgeline isn't just a software provider, it's a true partner in innovation. They're redefining what's possible in asset management technology, helping firms scale faster, operate smarter, and stay ahead of the curve.
I want to share a real-world example of how they're making a difference.
Chapter 3: What parallels exist between music creation and venture investing?
Let me introduce you to Brian. Brian, please introduce yourself and tell us a bit about your role. My name is Brian Strang. I'm the Technical Operations Lead, and I work at Congress Asset Management. How would you describe your experience working with Ridgeline? Ridgeline is a technology partner, not a software vendor, and the people really care. I get sales calls all the time and I ignore them.
Ridgeline sold me very quickly. We went from 7 billion to 23 billion and the goal is 50 billion. Ridgeline was the clear front runner to help us scale. In your view, what most distinguishes Ridgeline? They reimagined how this industry should work. It was obvious that they were operating on another level. It's worth reaching out to Ridgeline to see what the unlock can be for your firm.
Visit RidgelineApps.com to schedule a demo. I'm excited to introduce our newest sponsor, Arcana. Arcana is the world's most advanced portfolio intelligence platform trusted by institutional investors managing trillions in assets under management, including market neutral, long short, long only, and capital allocators.
Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and IDEO, construct optimal portfolios, and decompose performance at incredible granularity.
Chapter 4: How do The Chainsmokers manage failure in their careers?
Arcana is the only real-time, intraday system in the market with extensive live scenario analysis, custom screening and tagging, and a slate of one-click, lightning-fast portfolio construction tools, mock portfolio trackers, reporting, and single-stock crowding.
This is the kind of tool I wanted when I was managing public equities, and I'm sure you'll benefit from the insights the system has to offer. Visit arcana.io to request a demo and learn more. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
Chapter 5: What is the importance of intentionality in music and investing?
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 Review, our quarterly publication with in-depth profiles of the people shaping business and investing.
You can find Colossus Review along with all of our podcasts at joincolossus.com.
To learn more, visit psum.vc.
My guests today are Alex Paul and Drew Taggart.
Chapter 6: How did The Chainsmokers transition into tech investments?
You might know them as the Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high touch relationship driven approach that built their music empire now defines their investment philosophy. Their frameworks for backing founders mirrors their artistic approach.
They invest in obsessive individuals who will pursue their visions regardless of external validation, much as they've remained authentic to their sound despite industry pressures.
We discuss parallels between creative iteration in music and venture investing, particularly around managing failure, maintaining intentionality in an age of abundance, and the importance of taste as a differentiating factor.
Chapter 7: What does Mantis represent in their investment strategy?
Please enjoy this fascinating discussion with the Chainsmokers, Alex Paul and Drew Taggart.
How do you feel about models training on your content? I don't care. Yeah, I figured.
Chapter 8: How do The Chainsmokers define success in their ventures?
Yeah. Because it's like a cat out of the bag. We don't care about our music either. I ask, is there so much controversy around music and art?
Tripp Adler described a pretty successful company and he's starting something new. And he's like, you know, one of those founders where you're like, normally you'd be like, this is a really successful second time founder starting something in AI now. And I spoke to him. He was like, yeah, it's basically like licensing copyright rights that we find a way to protect and then get people paid.
And I was just like, this feels... It's like I'm going to stand in front of a tsunami and I'm going to hold it off. Yeah, I was like, everything here is like hinged on government protecting IP. And by the way, it's already too late.
I'd compare this phase in AI models training off of copyrighted data is the Napster moment, where the record labels couldn't figure out a way to sell music in the digital age. If they had been forward thinking and accepted that they would have created Spotify, we wouldn't be paying an extra 30% to a DSP. But they didn't.
And it had this whole moment where it's like, you can't really stop this from happening. So just embrace it and figure out how to harness it when it comes out the other side. One person will get sued.
Yeah. Like, who knows?
These models are going to train on this and they are going to be able to do these things that everyone's feared about them doing. But then we're going to be able to make better art or different art. Is there anything you do fear? Loaded question that I want to answer correctly. My first instinct is to say no. Because I feel, specifically us, we're DJs.
15 years ago, the DJ producer, and still to this day, you've seen the memes about they're just pressing play or all of their music is software. And...
I remember the whole first wave of that democratization of like music software being available and accessible and the barriers to entry coming down and all of us being able to make stuff that we weren't able to create before we gave, unless we had like access to a crazy studio. And I remember everyone saying that that wasn't real music.
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