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Earlier this year, I was at a dinner with a group of women and mentioned my “failed startup” like it was a quirky quip about my career. The host, who I’d met several times, looked surprised. She had no idea I’d started a company.

I realized I almost never talk about it. Sometimes the whole thing feels like a fever dream – a short chapter in my longish career. But there it is on Crunchbase, with my name next to “co-founder.” It happened. I just hadn’t wanted to bring it up (but I’ll tell you why I do now).

This week, I was considering an opportunity to invest significantly in a project. My potential counterpart is much closer to retirement than I am. Whereas, I have decades before I reach my retirement number, and more time to let capital mature. I know we could look at the same investment and feel very differently about how much risk makes sense, or how long we can wait for a return. But it took me a hot minute to remember why and how I already knew this lesson.

It brought me back to the startup. Yes, the one I don’t talk about. In my twenties, I had three roommates and paid barely a thousand dollars in rent. My co-founders had children, mortgages, and financial obligations that were much larger than my rent payment. They had big things that needed to be paid for with a big salary. None of that was wrong. But we hadn’t talked clearly enough about how those different realities would shape the risks we could take.

We started taking the contracts that came along. We closed the deals with new clients and started the work quickly. Making money is good for business, right? But I was more interested in building systems and a product than chasing one-off clients. We needed the revenue to pay the bills, but the contracts pulled us away from the company we’d set out to build. We were making money, just not in the way I’d hoped to.

That feels especially relevant now, when so many people are working as fractional CMOs, taking part-time roles, or building a startup on the side. You can test an idea while keeping other income. But going full-time changes the math. The business now has to support more of your life, and your tolerance for risk will change with it. All these problems would have been avoided if I had talked about those expectations before said leap was taken.

That’s what my failed startup taught me to ask before going full-time: Have we agreed on how long each of us can go before this business needs to pay us? We hadn’t answered that clearly enough. When money became urgent, we took work that moved us away from the original idea.

Calling the startup a failure feels incongruous now that I can see how it helped me think through this new investment. I used to be ashamed of that chapter. Now, I’m grateful for it. I know what questions I need to ask and will be using that experience to inform how I view business partnerships in the future with more thoughtfulness. If sharing what I learned helps someone have the conversation before they start, partner, or go full-time, maybe it was worth the legal fees.