What happens when you finally get everything you thought you wanted, and realize you want something else?

Joe Spector came to America from the Soviet Union at ten years old. His family arrived with $100 each. Joe had a red suitcase.

He studied his way into Berkeley, finished in three years, and landed a job at JP Morgan. It was the kind of secure, prestigious career his younger self thought meant he had made it.

Then he realized he didn’t care about it.

Joe left finance, moved into startups, and eventually helped build Hims, taking an idea around hair loss and sexual health and turning it into a public company.

Then he left again.

During COVID, a $2,000 emergency vet bill for his dog made him start asking questions about veterinary care. He took what he had learned building Hims and started Dutch, a pet telehealth company aimed at making veterinary care easier and less expensive.

But one of Joe’s first lessons at Dutch was that past success does not give you a perfect playbook for the next company. He initially tried to copy the Hims model. It didn’t work. Pet care was different. So he changed the model and kept building.

Joe’s story is about more than startups. It’s about refusing to confuse security with purpose. Sometimes the thing you worked years to reach turns out to be a place you need to leave.

On this episode of Keep Going, Joe and I talk about immigration, Wall Street, building Hims, starting over with Dutch, getting things wrong, and why being an outsider can make taking risks a little easier.

And we return to that ten-year-old boy carrying a red suitcase into a new country.

What would Joe tell him today?

Give yourself the freedom to look beyond what you think you need right now. There may be a much bigger life outside the path you can currently see.