A conversation with Seán Gallagher about starting again

I started Homestead Road in 2007. Seán Gallagher started Smarthomes in 1999. By the time we sat down together in our Miami office, we had each spent more than fifteen years in the business of houses — and we had both been standing in the market when it came apart.

That is where the conversation kept returning.

Seán was direct about what 2008 did to him. Contractors and developers stopped paying. The business lost enormous sums. Good people lost their jobs. Smarthomes had grown into the largest home technology company in Ireland, and within about two years it had failed.

I was two years into building when the same wave reached us. Our earliest years were shaped entirely by that downturn — nearly every assumption I held about how fast a company could grow got rewritten between 2008 and 2010. So I recognised the arithmetic he was describing. What I did not expect was where he took it afterward.

He spent years studying how other countries legislate around financial crises, and he has been developing a proposal aimed at helping countries prevent the worst effects of the next one. That is an unusual response to losing a company. Most people who get hit that hard either stop, or start again quietly. He went looking for the structural cause.

Two things I am taking back to the team.

The first is about timing. Seán did not start his first company until his early forties. I meet a lot of people who are convinced they have missed their window. He is evidence that the window is far wider than it looks.

The second is about what you do with your worst year. He could have filed 2008 under bad luck — the market turned, and it took the company with it. Instead he treated it as information: something to be studied, understood, and if possible prevented for somebody else. That is a harder discipline than resilience, and it is the part of the conversation I have not stopped thinking about.

We also talked about how quickly AI is reshaping the way all of us work. That one deserves its own conversation.