People ask me this in some form pretty often. Usually at the end of a conversation, almost like an afterthought. "So what made you actually do it?" The honest answer is annoying because it isn't one thing. It was a slow drip over about 14 months.

But if I had to pick the moment, it was a Wednesday in February 2018. I was in a conference room in Plaza Midwood with our CEO, a guy named James, and we were arguing about whether to build an integration with a PMS that I thought was already dying. He wanted to build it. I thought it was a waste of two engineering quarters. I won the argument, sort of. We didn't build it. But I remember walking back to my car and thinking, I have spent four years winning arguments like this, and the work that happens in this company because of those arguments is not the work I want to be doing.

That sounds dramatic. It wasn't dramatic. I drove home, made dinner with Whitney, didn't say anything about it. But the thought stayed.

The boring stuff first

I was VP of Product at a Charlotte real estate operations company. Good company, good people. James was, and is, a good CEO. We had about 60 employees, profitable, growing maybe 30 to 40 percent a year. My total comp was somewhere around $290K with bonus. We had a kid. Well, we didn't have a kid, but Whitney was running a marketing business and I was the steadier of the two paychecks, so leaving was not a casual decision.

The thing that's hard to explain about leaving a job like that is that nothing was wrong. If you've been miserable at a job and you quit, that story makes sense to people. "Of course, you were miserable." But when you leave a job where you're paid well and treated well and the work is reasonable, people get a little suspicious. Like there must be something you're not saying.

There wasn't anything I wasn't saying. It was just that I had been working on the same problem from the outside for too long.

The problem I couldn't stop thinking about

The company I was at sold software to multifamily operators. Big ones, mid sized ones. We had this product for resident communications that worked fine. Not great. Fine. And what I noticed, over and over, was that our customers' operations teams were all running the same broken playbook.

They had a property management system (Yardi, RealPage, Entrata, AppFolio depending on the operator) for accounting and leasing. Then they had a different vendor for resident communications, often us. Then a third vendor for work orders and maintenance. Then a fourth for resident screening. Then a fifth for renewals. None of these things talked to each other. The poor regional VP at a 200 property operator had to look at four dashboards every morning to figure out what was going on at her portfolio. And the on site teams were drowning.

I would go on customer visits and I'd sit with a property manager and watch her work. She'd have 11 tabs open. Maintenance requests would come in via three channels. She'd manually copy resident phone numbers between systems. She'd miss things. Not because she was bad at her job but because the tooling was bad.

And our product, the one I was responsible for, was making the problem slightly worse. We were the sixth tab.

I kept proposing that we expand the product. We could do work orders. We could do renewals. James didn't want to. His view, which was reasonable, was that our customers wanted us to do communications better, not be a worse version of someone else's product. He was probably right for that company. He had a board, he had a roadmap, he had revenue targets.

But I couldn't stop thinking about the property manager with 11 tabs.

The actual decision

The thing I learned from this is that big career decisions don't get made in single moments, they get made by accumulation. By June 2018 I had a Google Doc with maybe 30 pages of notes about what an integrated multifamily operations platform should do. I had three friends in product who I'd been bouncing it off. I had two operators who told me, separately, that they would use it if I built it.

And I had a slow growing feeling that if I didn't try, in five years I was going to be 40 something and watching some other person build it, and I'd be mad about that for a long time.

I told Whitney in July. We had been talking around it for months. She asked me three questions. How long can we go without your income, what does failure look like, and do you actually want to do this or do you just want to want to do this. The third question is the one that mattered. I sat with it for a couple weeks. The answer was that I actually wanted to.

I gave notice in October. Three months runway, professional handoff, no drama. James was honestly great about it. He even introduced me to two of the operators who would later become our first customers.

What I got wrong

I had a plan. The plan said the first version would take six months and we'd have paying customers by summer 2019. The first version took eleven months. We had a paying customer in October 2019. The product we shipped in October 2019 was a worse version of what I'd promised those original operators. They paid anyway because I had begged them to and because they liked me, not because the product was good.

I burned through more of my savings than I planned to. Mercury account went down to about $8K at one point in early 2020. I remember checking it on a Saturday morning and not telling Whitney for two days. (She knew anyway. She always knows.) Then COVID hit, which was somehow good for us, because multifamily operators suddenly desperately needed digital tools. By July 2020 we had eight customers and could afford to hire two engineers.

The seed round closed in March 2019, six months later than planned, smaller than planned. The Series A in 2023 was on a timeline I would have called insane in 2018. The Series B closed last month after I told myself I was done thinking about it about 40 times.

None of this went the way the plan said.

If I had to answer the question in one sentence

Here's what I tell people when they ask now, after thinking about it for a few years.

I left because I wanted to spend my forties on a problem I cared about, with people I picked, building something I'd be proud of regardless of whether it worked. The not working part was always possible. The not being proud of it would have been worse.

It's a slightly self serving answer and it's also true.

Whitney would add a fourth thing, which is that I am completely incapable of doing nothing, and that staying at a comfortable job would have eaten me from the inside. She is probably right about this too. She usually is.