Opening up a skate shop in 2000 without any prior work experience at all, or an idea about how to manage supply or turn a profit.
Being headhunted by Facebook for a job before it was a huge evil company (I didn’t get it).
Founding a digital product design studio Superawesome, and somehow keeping it afloat ever since 2007.
Funding and building a digital product people were willing to pay for. It was a freelancer's CRM/gig management tool called Funnel, and later sold it.