Five companies since 2005. One is still running. Most recent first: what it was, what I owned, and how it went.
Founded with Jay Wilburn, who I worked alongside previously. The company builds gamified learning apps. NCLEX Kingdom is the first; a second is planned.
Product shipped and live, marketing under way. Growth is the current problem.
First company where I committed to staying rather than solving and moving on.
A homeschool management app I built during the pandemic: students, assignments, grades, attendance, and report cards. It picked up a few hundred signups, and a handful of families kept coming back for years. Nobody ever paid. I never found a way to make the value obvious enough to charge for, so I shut it down in 2026.
Real users and long-tail retention with zero conversion. The clearest evidence I have that retention isn't willingness to pay.
Engagement without a price tag proved nothing. Charge from day one.
I ran a software consultancy for six years, delivering systems for dozens of clients across fintech, mapping, media, and hospitality. Architecture, delivery, stakeholder relationships, and small distributed teams. I wound it down in 2013 to go in-house.
Years later I revived the name for a kanban-style ticketing system that tracked how a team felt about each story in the backlog. It never found a market. I lost interest before it did, and it's been dormant since.
Six years of revenue and repeat engagements. I was the product, which is the one thing a services business can't scale.
Design everything so it still works when I'm not in the room.
A classroom-management app for K-12 teachers. At its peak it supported thousands of teachers and classrooms across the United States, organizing assignments and tracking student progress. It ran on ad revenue that never covered server costs, so I shut it down.
Thousands of teachers, no business model. The first time I learned that usage and revenue are unrelated problems.
Adoption without revenue is a warning, not a win.
A vacation-rental travel agency I co-ran as a partnership. We took bookings and we were profitable while it lasted. It ended over direction: how much to spend, what to build, what the product should be. We dissolved the company.
Profitable, then deadlocked. Alignment on spend and product matters more than the idea does.
Settle disagreements before they need settling.