Turning a Personal Learning Habit Into One of the Most Valuable Audiences in Finance

Patrick O'Shaughnessy recorded the first episode of Invest Like the Best in 2016 because he was frustrated with books. The podcast was a shortcut to better thinking. He was also running O'Shaughnessy Asset Management at the time, and no capital was raised for the show, nor was there a team behind it. He showed up and asked questions.

Eight years later, those questions had been downloaded almost 100 million times. Colossus, the company he founded in 2020, now runs more than half a dozen podcasts, hosts high-end investor events, and publishes a quarterly print magazine that reaches an estimated five million unique listeners a year.

The sponsors are Ramp, Vanta, WorkOS, and Ridgeline, all B2B tools whose ideal customers are almost exactly the people listening to his shows on a Monday morning commute.

The whole business grew by going deep on the professional investor or serious operator who reads everything, listens to everything, and will always want one more conversation with someone smarter than them.

Before Colossus existed as a company, the entire operation ran alongside O'Shaughnessy's day job, drawing on the access he had built over years of running an institutional asset management firm.

What made the show compound was the guest list. Because he was one of them, running money and thinking about markets, serious investors trusted the conversation.

The listeners who found the show were equally specific. People who had already read the public record on guests wanted the unscripted version. This is a different audience from someone who stumbled onto a business podcast from a search result.

By 2020, Invest Like the Best had enough audience and revenue to sustain itself as a profitable solo operation. O'Shaughnessy formalized Colossus and began building a network around it.

He started with David Senra's Founders, which was obsessively researching audio essays on founder biographies and had a small but intensely loyal audience.

O'Shaughnessy recognized the quality before the scale and brought Senra in as a partner rather than offering a licensing deal. This gave the show access to:

The cross-pollination that followed was something neither show could have generated alone.

Business Breakdowns came next, with in-depth analyses of individual companies for investors who want to understand how specific businesses operate at a mechanical level.

Each show served a distinct need within the same universe. The logic was not to create variety, but to give each potential listener an independent reason to show up.

Both are the kind of professionals whose employers sponsor the tools they use at work.

The Colossus magazine launched in late 2024. What looks like a nostalgia play from the outside is something more deliberate.

Issue 01 was limited to 1,000 copies and shipped only to the US, UK, and Canada. This created artificial scarcity and allowed Colossus to test fulfillment at a manageable scale before expanding.

By Issue 04, it was featuring profiles of figures like Thomas Peterffy alongside essays on AI in private markets, with an editorial ambition that puts it on par with serious long-form financial publications.

The membership model bundles multiple layers of value:

Listeners who would not pay for a podcast subscription may pay for a physical magazine that also unlocks additional audio.

Colossus also offers corporate multi-copy subscriptions, which opens a different kind of sale. 

How the Sponsorship Economics Work

Five million unique listeners annually is a meaningful number, but it is not how Colossus competes. What it offers sponsors is concentration.

Colossus has committed to content with a long shelf life. The oldest episodes still receive significant engagement, which means sponsors buy placement in a catalog that continues to generate listens for years after publication.

Colossus also sells sponsorships directly rather than through a network.

O'Shaughnessy's theory of audio informs the entire network's design.

Audio is easier to produce than comparable-quality video and it carries emotional resonance that writing cannot match.

That combination of low production friction, high convenience, and emotional depth makes it the most leveraged format for long-form intellectual conversation.

This is why Colossus has not launched video versions of its podcasts.

Video would:

The intimacy of a long interview, where a guest says something they would not say on camera, is part of the product.

The platform strategy reflects the same thinking.

Colossus publishes across every major directory, but the canonical experience is the website, which hosts full transcripts and episode archives.

Each episode generates ongoing search traffic. Someone researching a specific guest or company finds the Colossus episode months or years after it aired.

That extends the value of every conversation long past its original publish date.

Colossus did not start with a plan. It started with a habit. Asking better questions and staying close to a specific audience over time.

Everything that followed is consistent with that starting point. The podcasts build trust. The magazine adds depth. The events convert attention into relationships. Each layer works because it serves the same person.

The lesson is not about format. It is about precision. A clearly defined audience compound. A broad one does not.

Most media expand first and figure out revenue later. Colossus built something specific enough that revenue was already there.

See you next week.

If you liked this edition of Growth Curve, forward it to a founder or marketer who needs to stop renting their audience — and start owning it.