the wrong co-founder

My first real mistake as a founder wasn’t about product or tech, although both did change from what they were originally. It was bringing in a friend—who was also my ex—to help build the company. I thought splitting the responsibility of running things would make it lighter, like a feather. I thought trust was enough. It isn’t. It’s like the weight that hits Wile E. Coyote—you can’t run your way out of it. You need more than history. You need someone who shows up every day, who wants to, and who can. Even if things are going swimmingly, there’s likely a time when they won’t, and when personalities are really under the pressure of potentially seven figures, or eight, or ten, or none—who knows. This might sound pessimistic, but it’s not. It’s a lesson in optimism and learning. You get better by going through it.

what I missed

We never defined the work other than at a high level: “you take marketing and finance and corporate governance bullshit, I’ll take engineering, product, and share some of the marketing.” We didn’t decide how decisions would get made other than “we’ll always run things by each other,” or agree that building a real company is full-time—like, seriously, 3 AM every night and no Cinco de Mayo parties because the patent. Startups don’t wait for you to catch up. We should have put it in writing, apart from our Founders Agreement. We should have actually weighed and measured the Founders Agreement, not signed it on our mobile devices on a whim thinking it would never really matter. I should have said what I wanted. He should have said what he wanted. We should have talked about our “fuck you numbers.” It was my first time doing this without a team, or a big company’s money, or someone else’s rules, so I can’t blame myself. I can’t blame him. Or the situation, or really anything. I can just learn, and share my experience so others don’t, hopefully, repeat the same errors in their founder journey.

what he brought

He was ambitious and hungry. He wanted to be CEO. We actually fought about who would be CEO in the end. He wanted to be the one walking into the room as the leader of a big company, the one selling it to people, the one in front. He had what I didn’t—the desire to be seen, to be admired. I prefer to do things in the background and admire my work from afar. He helped with incorporating the company, and writing (because I am obviously bad at writing). He was great at scheduling things, talking with potential customers and investors off the clock, and getting folks excited. But he just didn’t have enough time. He wasn’t willing to take the same risk, mostly because he isn’t as privileged as I am and isn’t willing to lose it all, which I get. But that’s what it takes. I now have to be a different person, and for that I am thankful, because I am stronger. But it was painful to lose him—he mattered.

when it turned

The patent. By the time it was ready for another person to review, it was like 60 pages. I had written it, read it, and iterated on it at least a hundred times—or that’s what it felt like—by the time it was ready to be submitted. All that needed to happen was his eyes, confirmation, and a plus-one. But that was also the same day as Cinco de Mayo, and the fun was enticing for us both. I didn’t buckle and submitted that night—he went for a marg. It was the beginning of the end for our co-founder-ness.

Around that same time, I pitched a licensing deal where I would own the patent and the company would lease it for free—unless I was no longer at the company, at which point it would have to pay for it. He said it wouldn’t be good for the company. What I found out later was that he started second-guessing my motives. I get it. What was really happening is that my nine-hour days felt worth more than the 50% of the company I owned, and if I was putting in all the real work, I wanted a bigger upside. In reality, I pitched that as a cry for his attention, to help course correct, and hopefully get more “work” for the company out of it.

My error here was missing that he just didn’t have the time. He was working three other jobs after all. I was naive. I could have been kinder, nicer, less aggressive even. He mentioned some of the things I said were emotionally abusive. This was hard for me to hear, but he’s probably right in some ways. I can be mean when I am tired, hungry, and at the end of my proverbial leash. I needed him to help correct me and bring me back down to normal. He was my opposite after all. I didn’t realize that it was unrealistic to expect this from a business partner—and maybe even from a friend. I have to regulate myself, and make sure I take time to garden my body and my brain, not just the business. That lesson is one I’ll take with me forever, and I thank him for that.

how it ended

The real ending was in Dolores Park. We sat and talked a bit, both of us nervous—well, I was nervous, he was probably just mad, because it was nothing like when we first met at that club on his 23rd or 24th birthday, I forget which. In some ways, it felt like the last time we’d ever meet. The conversation ended with me offering that dinner I owed him for helping me sell some jewelry I needed to fund my lifestyle and the startup (that damn patent was expensive). He agreed to the dinner, after which he walked home, looking a little lighter in his step free of me and the startup, to the puppy we used to share and his beautiful boyfriend I sometimes wish was still me. I took some solace in the idea that we were still friends, but now, maybe we aren’t? Ugh, running a company is hard. Don’t do it with your friends, ex-lovers, or family. Be warned.

what founders really need to know

When you start out, you think you know how hard it’s going to be. I didn’t. The real test isn’t the product, or the legal forms, or the late nights—it’s everything that happens to you, and who you become in the process.

I used to do ops and product, and engineering, and recruiting and everything. I thought I knew it all. In reality, it couldn’t be more different. Paying taxes, statements of information, articles of incorporation, a million contracts, boilerplate that isn’t code—the whole thing is dizzying. I was hoping he’d take this on, but I now see the value in knowing how to do it all myself, and I see the new me in it. I read every single line of a contract, the bylaws, the license agreement for the patent, and you should too. It’s what dictates the next 10+ years of your life as a founder, and maybe more if you believe the folks in “Founder vs. Investor.”

You don’t see it until you do, and it is worth it even though it doesn’t feel like it. Or at least I hope it is.

for the record

Thinking about it more, I don’t actually know if any of this was worth the cost. Losing a friend, especially an ex, never feels worth it. If I could do it again, I’d have shared my needs as a founder. I’d have explained that I am not the same person in business as I am in our friendship, or as I was in our relationship. I am somehow much stronger, but also much weaker in other ways. Please, dear reader, take note if you end up working with a friend or ex or family member: make the clear distinction between the you that is a business person, the you that is a friend, and the you that is in the clubs or when you see a cute boy, because they are all versions of you that show up at different times, and you better bet they haven’t seen the business you yet.

Some days, the work is worth every cost. Other days, it isn’t. I’m still here, still learning, and still doing the job, and I plan to until this thing really does reduce STI transmission rates and for me, that’s enough.

letter to you, and to me

You saw something in this before I did.
You helped turn it from idea to company.
You called out my blind spots.
You pulled me back in when I wanted out.
I wanted us both all-in, building something that mattered.
We didn’t get there.

I hope your part of this means something—whether or not we ever talk again.
I hope you know you mattered, even when things fell apart.

To myself:
Keep building.
Remember where you started.
Don’t lose more than you have to.
If it works, let it mean something for both of us.