In my twenties I founded four different but related companies. Each one lasted about five years and overlapped with the one that came before. In all cases the customers were creatives, designers and builders.
Most of what I know, I've learned from trying to make these businesses work. They spanned social networks, conferences and live events, agency and consulting, and finally hardware + software.
The summary of them goes like this:
Positive Posters was my attempt at giving graphic designers a way to make impact on the world. I asked the question "If you had to design a poster that advertised an issue you cared about, what would that be?". We built a Wordpress website and invited people to submit posters. In our third year, Yoko Oko answered a letter I'd sent her and we arranged for her to Tweet about our work to her followers.
This sent so much traffic to our website that it broke and at the end of the year, we faced a ~$50k hosting bill.
By this time, people were asking me lots of questions about building websites and apps. So I founded Joan, a product design and research agency.
While we loved working with clients, my co-founders and I dreamed of having customers and building out own product. After a couple of false starts, we eventually came up with Tiller. A hardware and software solution to improve time tracking for agencies which was funded on Kickstarted and shipped around the world in 2019.To pay for the bill, I started Sex, Drugs & Helvetica. A single day design conference. I rented a conference room and divided the number of seats by the hosting bill. People loved the conference and we continued to run it for five years.