Nine days earlier, I told two people I was probably going to pass on Pinata.
I wrote one advisor that the decision would free me to help her company. I told an executive recruiter that I had decided not to pursue something and was definitely still available for fractional or full-time work.
That was honestly where I thought the decision had landed.
Then I met with more of the Pinata team and started doing the work anyway.
The company needed better property and facilities data. I wrote a scraper, sent a live Google Sheet, and left it running locally when I hit the Sheets API limit. I added error checking, worked through missing addresses, and offered to connect another data source. I was not an employee yet. I just liked the problem and knew how to make the situation better.
The same thing happened with the team plan. I started talking with recruiters about a lead engineer, a junior engineer, two cost-efficient mid-level hires in Latin America, and a temporary group in Eastern Europe to help with the codebase transition.
That made the decision clearer than another interview would have. I can spend weeks talking about a role and still be unsure whether I want it. Give me one broken data flow, one hiring problem, and a team trying to move, and I know very quickly whether I care.
I cared.
The offer kept moving too.
The hard part remained the options. I had asked for a longer exercise window because startup exits often take seven to ten years and leadership teams change along the way. In my email I wrote that I had given back well over $30 million in equity during my career because I could not retain it.
That number sounds insane. It is also how startup equity can work. A grant can be worth a lot on paper while the cash and tax cost of exercising it makes the ownership impossible to keep.
I was not trying to get more equity. I wanted a practical route to own the portion I earned.
The longer exercise window was one answer. A company buyback or another way to deal with vested options could also work. The exact mechanism mattered less than avoiding the standard version where leaving a private company creates a ninety-day bill large enough to erase the value of the grant.
I had seen that movie already. I did not want another ticket.
We worked through the issue until the offer was something I could accept. Sunday afternoon, the last day of the quarter, I wrote back:
“The offer letter looks great.”
Then, in caps, “I REALLY appreciate and acknowledge the effort on this one, I am excited to get started!”
I signed the formal letter the next morning.
The role was Chief Product and Technology Officer, full time, with an April 22 start. The letter also made room for the parts of my work that did not disappear when I took a job. I could remain a cofounder and board member at Apply, advise BAB, continue startup work through Black Raven Labs, and advise the early AI networking project, with the outside work capped at fifteen hours a month.
That mattered. I wanted to commit to Pinata without pretending the other companies, people, and ideas had stopped existing.
The carveout was not permission to treat the job as part time. Pinata was the full-time role. It was a written acknowledgment that Apply still had board and cofounder work, a few advisory commitments were real, and I would keep them inside a small monthly limit instead of hiding them or acting surprised later.
The offer had followed me to Phoenix as one more unresolved decision. It ended back in New York with a signature.
My deadline was the end of Q1. I accepted on the last day and signed on the first morning after it.
Close enough.