Two things I built, with receipts.

In May 2022, DoorLoop’s CEO and CMO asked if I wanted to build a website division for their property-management customers, then warned me they had tried it at a previous company and couldn’t make it work. I said, “Cool, I won’t fail.” Then I asked what would happen to me if I did. “We’d move you to something else.” That safety net let me build boldly instead of defensively.

The earlier attempt died from too much customization and no system. So I built the opposite. Smart constraints instead of unlimited options, repeatable processes instead of heroics, and an offer shaped by eight months of hearing customers complain about their websites in support calls. The first site went live in November 2022.

By August 2025 the division had published more than 1,000 websites, run by me full-time plus one colleague for about two hours a week. Property managers who used to apologize for their websites now show them off in sales calls.

Read the full story →

Jewish learning is profound, and it is often locked into rigid schedules, intimidating entry points, and one-size-fits-all formats. I grew up in day school with teachers who made the texts feel alive, and it bothered me that most people never get that.

Derekh Learning is an iOS app that uses AI as a chevruta, a study partner, for Torah, Talmud, and Jewish wisdom. Your derekh ("path") adapts to your pace and your actual questions, whether that’s parenting, work, or purpose. Ten minutes between meetings counts. Nap time counts. There is no guilt for missing a day.

The design constraint was to make the AI serve the tradition rather than flatten it. The technology surfaces connections and suggests pathways; it does not pretend to replace the texts or the teachers. That constraint shaped every product decision, and it is the story I tell when teams ask how to ship AI features people trust.

Read the launch post →