The Ghost That Built an Empire with J Schwan

Written By Ashley Logan

It takes a particular kind of bravery to walk away from something wildly successful. Not because it failed, but because you realized you were no longer the right person to lead it.

I first met J a few years ago at a coffee shop near where we both live in Glen Ellyn. He had just stepped away from Kin + Carta - the publicly traded B Corp he'd scaled from a solo venture to over 2,000 employees across four continents - and he was in that uncomfortable in-between phase, figuring out what came next. He talked about the second mountain - I thought it was a business idea. After this conversation, I think it was something much bigger. A whole stage of life he was choosing to move into.

J founded Solstice at 23. Scaled it. Sold it. Watched it become Kin + Carta, then stepped into the CEO seat and led the firm through four years of transformation and public market pressure. And during the last two years of that run, when the accolades were coming in and the stock was performing, he was miserable. The role had pulled him so far from the work that actually gave him life, he knew he was no longer the right person to be in it.

So he left. And where he landed says everything about who he's become.

J is now the CEO of Gladiator Tennis, a national racket sports league modernizing how adult recreational athletes connect, train, and compete. The reason he ended up there isn't a market thesis - it's personal. He spent 25 years building the digital world, and he wants to spend the next 25 getting people off their screens. That shift started on a tennis court in London, when he was isolated, grinding, and completely one-dimensional. The game brought him back to life. Now he's building something so it can do the same for 100,000 other people.

This week, instead of a traditional interview, we did something different.

We played three games, all centered around fear. We explored questions like:

  • What’s scarier - failing publicly, or succeeding and feeling empty?

  • What part of your success actually hurt you?

  • What are you afraid to admit out loud?

We ended up talking about what it actually looks like to walk away from a wildly successful machine, name the thing that drove you there, and choose a second mountain that means something to you personally.

In This Episode, We Talk About:

  • The "ghost" - J's name for the internal force that chased every achievement and still couldn't be satisfied

  • Why he tested the investor lane after Kin + Carta and knew within six months it wasn't enough

  • How transparency about imposter syndrome can actually become a leadership superpower

  • The fear underneath publicly celebrated success, and why J was miserable when the stock was doing great

  • Tennis saving his life in London, and what that taught him about what he actually wants to build

  • What the second mountain really means when it's less about climbing and more about returning to yourself

My Key Takeaways from this conversation with J Schwan:

  1. The ghost is real - and naming it changes everything.
    J describes this relentless internal force that no matter what he achieved, kept telling him he needed to do more. It brought him real success. It also brought him to genuine unhappiness. Naming it, understanding where it came from, and learning not to let it lead the way — that's the work many leaders never do.

  2. Public success and private fulfillment are not the same thing.
    During his last two years at Kin + Carta, the stock was performing, accolades were coming in, and J was completely miserable. The machine was working, but the soul wasn't. Most leaders never admit that out loud. J did.

  3. The best leaders make themselves unnecessary.
    J shared a philosophy from his colleague Kelly Manthee: your job is to put yourself out of a job. Empower the team. Build people who don't need you to call the plays. That's not just good culture - it's what lets you leave with integrity when the time comes.

  4. The second mountain is about returning to what made you come alive.
    J missed the zero-to-60 phase, and wanted to experience it again. The building, the learning, the beautiful unknown. He wanted to solve a problem that mattered to him personally. Tennis saved his life in London. If he can give 100,000 people that same experience, that's his new definition of winning.

  5. Fear evolves - and that's a sign you're growing.
    At 23, J's fear was: what will people think if this doesn't work? Now, it's: what if I can't fulfill the promise I made to the people who bet on me? That's not the same fear. That's a leader who has changed.

The best second acts aren't really about starting over. They're about going back to what made you come alive in the first place, and doing it with everything you've finally learned about yourself along the way.

Listen to the Full Conversation:

Connect with J Schwan:

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Resources Mentioned:

If you have a topic or guest you'd love to see on Fearful Giants, send me a message.

Clay

Ashley Logan
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