Patrick O'Shaughnessy

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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.

Ladder was my first angel investment ever.

It was made entirely on trust in Tom Deegan at a point when I had no idea what I was doing in venture capital.

What followed over the next seven years is one of the most unlikely and dramatic business stories that I've been a part of.

Today, Ladder is the number one strength training app.

They're approaching $100 million in ARR and more than 300,000 paying members.

But the path from near death to dominant fitness app involved debt collectors, leadership changes, and a full reset during the pandemic pivot.

At one point, Greg Stewart entered what he calls a cave process, where a huge amount of effort and time went into cracking the TikTok algorithm just to make sure from content work as a growth engine.

Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising whatever amount of money they could from any investor, and willing to do whatever it took when most founders would have quit.

In this conversation, we cover the messy early years when survival meant negotiating creditors at 20 cents on the dollar, how they figured out their customer by reading thousands of app store reviews, and how they built the TikTok growth engine without any performance marketing background.

Tom and Greg share their long-term vision for becoming the system of record for health and fitness, their approach to AI, and why they still have no managers on a 30-person team.