“Can we be both?”
I had written that Caroline and I could be a formidable team. Then I got distracted by the word. In French, formidable means tremendous. In English, it can mean intimidating.
Could we be both?
The joke was sitting at the top of a much more serious note about becoming cofounders.
Amanda and I had just spent a few days in Paso Robles. Her support mattered more than anything in the document. She had seen the good, bad, and ugly of nearly every startup I had helped build. She understood what a founder role does to the calendar, the bank account, and the rest of life.
Her job was also considering a promotion that could put her in St. Louis most of the week. If that happened, we might carry two homes for a while. I might rent out the Williamsburg apartment, work from Rockaway, and take the ferry into the city. I asked whether Caroline and I could do most of our in-person work in Dumbo or the Financial District and build around two or three office days a week.
This was not an abstract conversation about company culture. It was about whether Amanda and I could make the math and geography work.
The company math needed work too.
Caroline wanted to maintain majority control through the seed round. We both knew this was not the usual two-people-quit-together and split-it-fifty-fifty story. She had already raised a friends-and-family round and worked on the idea before I arrived. I was joining with years of product, technology, and company-building experience, plus a willingness to take a very large pay cut and start over.
I did not want to wake up two years later feeling like the ownership gap had nothing to do with the work or sacrifices each of us made. I wrote that plainly. We talked through equity, future pay, board seats, hiring, office logistics, and how we would divide decisions as the company grew.
I used Apply as one data point. Three of us had built that company together, and the ownership and board structure reflected it. Loop would be different, but it helped to have a real example instead of negotiating entirely from vibes.
Meanwhile, I had only been at Pinata for eight weeks.
The work there was going well. The direct-to-consumer product was live, the product backlog was getting cleaned up, and we were reorganizing engineering around the parts of the business that mattered. Leaving that quickly felt lousy.
My proposed exit was to give four weeks of notice, with a strong preference to wrap the full-time job in two weeks and remain available on a small fractional basis while Pinata hired a replacement. I wanted to do the right thing without putting Loop at risk before it had really begun.
Loop was still early. We were budgeting one or two more design sprints and wanted enough product work to carry us through a beta. We needed to raise more money, sharpen the full vision, and decide how much product we could honestly build with the cash we had.
The formal offer was dated June 14. It said Co-Founder and Chief Product and Technology Officer, reporting to Caroline, with the work based principally in Brooklyn.
Two weeks earlier, the email subject still said “potential co-founder.”
The word potential was gone.