I'm on year 13 of running businesses of one (I built an audience development platform and an educational/fundraising platform, plus a handful of smaller ones). On the plus side, I'd say that it has been pretty easy to maintain margins and keep cost under control. It's also easy to stay under the radar of larger competitors. On the downside, I think acquisitions would have been easier if I had a team in place and higher revenue, even with lower operating margins. Last year, my revenue fell a bit and I've considered looking for a more traditional job, but it has been harder than I expected because I believe my experience may not fit a traditional job description. Still, if you can swing it, I would very much recommend it, but good to consider the downsides as well.