I started a company to leverage an order taking and customer management system I’d built for a friend’s b2b outside sales company. Before, they were managing everything with excel spreadsheets on a shared drive and it was a mess. After, everything was in a php application that could set up a recurring credit card transaction within a few clicks. It used AJAX (in 2004, before responsive forms took off) to take different form inputs.
I rode that one client pony for too long. Managed to get a second client, but I hadn’t worked out a good pricing strategy. I needed to offer the program publicly, but we were too busy doing feature development for our two clients to develop features for multi tenant. I was bad at the administrative aspects of running the company, so I inadvertently ran up a bunch of bills. I wasn’t keeping my sales funnel full or dedicating much time to finding new clients and calling on them. The whole thing went crashing down when my clients decided that they didn’t want to have 100% dependence on my company anymore and per our contract paid a one time lump sum for a copy of the software. Still wasn’t enough to fill the holes the bills had left.
I could have been SalesForce if I hadn’t been an arrogant 24 year old who couldn’t learn from other people, but instead I ended up in about $50k of personal debt.