In my last post, I wrote about the moment I decided I wanted to build something of my own. It was a quiet decision. No fanfare, no plan, just a feeling that solidified into a direction.
But a direction without a partner is just a guy with a dream and a laptop. I needed someone to build with.
Turns out, he was already in my life. I just didn’t know it yet.
About a year earlier, I was at a security startup, building a team from scratch. I was hiring carefully, handpicking every person, making sure each one was the right fit. Every person except one.
Dan joined the team as my first hire, but I hadn’t chosen him. He was placed there. At first, I wasn’t sure what to make of it. But I gave him the onboarding I’d always dreamed of giving. Thorough, intentional, the kind I wished someone had given me earlier in my career.
Then life hit hard. Dan lost his father.
I watched most of the company carry on like nothing happened. I couldn’t do that. I made sure he knew someone had his back. I checked in. I listened. I showed up. Not as a manager performing empathy, but as a person who gave a damn.
Here’s the thing though: I already knew I was leaving. I had signed with another company. Dan had joined a few weeks earlier, and the first engineer I’d handpicked for the team, a brilliant woman who would later become a close friend to both of us, was about to arrive. The team I’d built from nothing was finally taking shape, and I was walking out the door.
The guilt was real. So I did the only thing I could. I stayed in touch. Kept supporting them even after I left. It wasn’t a strategy. It was just the right thing to do.
Months later, after I’d left that next job too (the one from the first post), Dan called me. He’d been fired.
He wanted to sit down and talk.
We met, and within minutes, we were saying the same things. We both wanted to build something bigger than ourselves. We were tired of building other people’s visions. We wanted ownership. Not just of code, but of direction, of purpose, of the thing itself.
The energy was electric. Two people who’d been carrying the same restlessness, finally saying it out loud to someone who understood.
But I’d learned something from watching my friend Avi build his startup. Excitement is cheap. Alignment is expensive. You don’t become co-founders because you’re both excited on a Tuesday afternoon. You become co-founders because you’ve looked at the hard questions and didn’t look away.
So I said: “Let’s not rush this. Let’s do this right.”
I went home and built a document.
Not a business plan. Not a pitch deck. A questionnaire. A structured framework designed to create a baseline of honesty between two people before they commit to building a company together.
The idea was simple: each person fills it in independently, about themselves AND about the other person. You answer the same questions twice. Once looking in the mirror, once looking at your partner. Then you sit down and compare.
Here’s what it covered:
- The “Why” Question — Why do you actually want to start a startup? What are your real motivations?
- Thinking About the Future — Imagine 5 years ahead. What does the company look like? What culture have you built? Why do people love working with you?
- Strengths and Weaknesses — What are you good at? What are you lacking? What do you need from a co-founder to balance you out?
- Who Will Be the CEO? — The question nobody wants to ask on day one. We asked it on day zero.
- Personal Intuition — Do you genuinely trust this person? Is there anything bothering you that you’re ignoring? How do you feel about their working style?
That last section is the one that matters most. It’s the one where people either get honest or get polite. I designed it to make politeness impossible.
If you want to use this with your own potential co-founder, here’s the blank template. Duplicate it. Fill it in separately. Then sit down together. It might be the most important 4 hours you ever spend.
We booked an afternoon. No distractions. No phones. Just two people, two laptops, and a Notion doc that was about to make things very real.
The first hour was easy. We read each other’s “Why” answers and nodded along. We both wanted to build something meaningful. We both cared about culture. We both talked about creating a company where people come first. So far, so good.
Then we got to Strengths and Weaknesses.
I had written, honestly, that I was worried about Dan’s technical depth. I wasn’t sure he had the engineering chops for what we’d need to build. It was hard to write, and harder to read out loud.
Dan had his own honest observations about me. Things I needed to hear, even if they stung. That’s the whole point of the document. If you can’t be real with each other before you start, you definitely can’t be real when things get hard.
We both wanted to be CEO. That one made us laugh. But we’d both also written that we’d do whatever was best for the company, even if it meant stepping into a different role. That alignment mattered more than the ambition.
The Personal Intuition section was the hardest. I had written that I genuinely trusted Dan. He’d written that he trusted me, with hesitation. He didn’t know me well enough yet.
That could have been a dealbreaker. Instead, it became a foundation. He wasn’t telling me what I wanted to hear. He was telling me the truth. And honestly? I respected him more for it.
After four hours, we didn’t have an idea. We didn’t have a product, a market, or a revenue model. We didn’t have a name.
But we had something better. We had honesty. We had alignment on the things that matter before the first line of code, before the first pitch, before the first fight at 2am over a feature nobody will ever use.
We looked at each other and said: “Let’s do this.”
We had a partnership. Now we needed an idea. That story, the brainstorming, the pivots, the startup called Butler AI, and all the mistakes we made along the way, is for next time.