Now

This is a now page. It's a snapshot of what I am doing and thinking about at this specific moment. I try to update it once a quarter. The version below is current as of late April 2026.

Work

The Series B closed on April 4. I have been spending most of my time over the last six weeks on hiring planning for the next 18 months. We need to add about 22 people across engineering, product, customer success, and sales. The plan exists. The hard part is staying disciplined about who we actually bring in.

I am also working with our head of product, Sarah, on a fairly substantial rewrite of how our resident communications module handles SMS. We have been getting it wrong for about a year and a half. We are finally getting around to fixing it.

Speaking at NMHC OpTech in Chicago in June. It's the one I keep getting invited back to. The topic this year is platform consolidation in multifamily operations. I expect the room will be skeptical and that is fine.

Reading

I am about a third of the way through The Power Broker by Robert Caro. Hardcover. More on this here.

I just finished re reading The Hard Thing About Hard Things by Ben Horowitz. I read it the first time in 2019 and missed about half of what was useful in it. I caught more this time.

Next up: an old copy of A Pattern Language by Christopher Alexander that's been sitting in a stack on my desk since January. I have been told by basically every product person I respect that I need to read this. We will see.

Listening

The Acquired podcast episode on Costco from last spring, which I had been told for a year I needed to listen to and finally did on a ride two weekends ago. It was worth it. Also the Invest Like the Best episode with Mike Maples Jr. on inflection points, which is more useful for thinking about company building than the title suggests.

Music: I have been on a Big Thief kick all month. No idea why.

Life

Whitney took Otis to the vet last Thursday for his eight year checkup. He is in good shape considering. His back hips are starting to show some early signs and the vet wants him to start a glucosamine routine. He has already figured out which corner of the kitchen the new pill bottle lives in and is suspicious of it.

Whitney is in the middle of a brand rebuild project for a Nashville client that has her on planes more than she'd like. I have been doing more of the morning dog walks as a result. The morning light in Dilworth in April is something I forget about and then am reminded of every spring.

My parents are coming up from Atlanta the second weekend of May for Mother's Day. We are taking them to a place called Stagioni on Providence Road that we like.

Thinking about

Whether Plotline should expand into single family rentals as a vertical. Pros: real market gap, our existing tech stack covers about 80 percent of what's needed, our investors think we should. Cons: it would distract us from the multifamily core for at least 18 months and our multifamily roadmap is already overbooked. Genuinely unsure. Currently leaning no, but I have changed my mind on this question three times in the last six months.

Whether I should write more often on this site. I have been writing posts roughly every six weeks for the last two years and the rhythm feels okay. But I keep having thoughts that don't make it onto the page because they're not quite long enough to be a post. I have been considering a "notes" section that is shorter, less polished, more frequent. Have not committed yet.