“Potential co-founder” was still a question, not a title.
Caroline and I had spent a few weeks working together on Loop. The product work was real. We had prototype prompts, an early relationship digest, a designer, and a long list of questions about how a professional network product should be different from LinkedIn.
Working on something together is not the same as starting a company together. We needed to learn how the other person made decisions, handled pressure, treated a team, and dealt with disagreement. The sensible version of co-founder dating included references in both directions.
I spoke with someone close to Caroline and thanked her afterward for being direct about the possible partnership. Caroline spoke with people who had worked closely with me. I introduced her to one former colleague by saying he was in my top three, then corrected myself to number one. I told her he was the best analytical mind and general technology leader I had worked with.
The process was deliberately mutual. We were not asking, “Is this person good?” We were asking whether the combination made sense and what each of us should know before making a much bigger commitment.
The paperwork had not caught up with the question. An advisor agreement arrived first so there was a clean way to cover the work already happening. I signed it and replied, “Neat! Money is great :).” Technically an advisor. Functionally deep in product, brand, and co-founder references.
The first visual identity work arrived with two treatments. I did not love either one. One felt flexible but bland. The other had brighter colors and interlocking circles, but the color wheels stressed me out. Too many years in New York for me. Black on black :).
I sent a long set of notes from a plane with terrible Wi-Fi. The mark needed to work without the word. The product needed warmth without looking soft. Most importantly, Loop had to convey connectedness without becoming another generic network diagram.
Later that day I introduced Caroline to one of the professional leaders I respect most. The subject line said “potential co-founder.” In the note I explained that Caroline and I were exploring co-founding, sharing some of our closest connections, and trying to assess mutual fit.
That was accurate. The question was no longer hypothetical. It was just not answered yet.