Ola disarmed my best joke in the first minute. Her name sounds like hola in Spanish, so I made the obvious comment. She told me that if she had a cent for every time someone said that, she'd be a millionaire by now. Fair enough.
She was calling from central Italy, near Rome, though that's only her current base. Ukraine, Germany, Mexico, Portugal, now Italy. When I asked who she actually is, the CV stopped being much use.
You can't scale belonging
Ola has built community twice. Taste Remote, an online food community with 17+ chapters. And Nesting Away, a coliving villa an hour north of Rome. Both deliberately small. Once a group gets too big, people stop knowing each other, and knowing each other is the entire point. She put it more bluntly than I would have: she doesn't want to be surrounded by copies of her own brain. Smallness isn't a constraint she's working around. It's the product.
When signing the budget stopped meaning anything
Before the community work, she built Apptrust into a seven-figure agency. Berlin, Wroclaw, clients in Japan and Korea, 8am calls with Asia after a 2am dinner. The classic next-big-thing treadmill. The signal that it was over wasn't dramatic. Signing a new budget used to give her a small hit of self-assurance, and at some point it just stopped. She didn't care anymore. So she followed the thing that did still light her up: watching people from her first retreat start projects together and stay friends years later. That's a different signal than a new client budget.
I asked her to coach me
The part I keep coming back to is when I flipped it and asked Ola for advice on building my own practice. She didn't hedge. Find your niche first, then build your positioning so you become the obvious choice. Most new coaches stay halfway in and halfway out, never owning the new identity. Practice your one-line introduction until it sits at the front of your brain, not the back. Document every session from day one, while it's still vivid. And don't over-build. Systems should match the stage of the business. Over-engineering early is just avoidance dressed up as productivity.
She drew one more line I liked, on AI. A lot of founders call it their co-founder. Her answer was a flat no. A tool, yes. Brainstorm with it, generate options. But you still have to make the decision. You can't outsource that one.
What I took away
Two things stuck. First, the problem a client brings you is almost never the real one, in coaching or anywhere, so the skill is knowing what to dig for underneath. Second, rest days for the brain are as necessary as rest days in the gym. We accept that in sport and somehow never apply it to our thinking work.
Worth a watch if you've ever quietly confused building a bigger business with building a better life...
