I ran a one man side gig for a couple years (farm management software). Got it to $200k and growing after 6 months in the market but I needed to bring the development in-house.
Could've used outsourced talent for all dev and customer support but interestingly enough the reason why I hired was "what happens to all of our customers if I die?". I felt like I owed it to them to put a team in place, albeit a small one.