10 Crazy Things I Did to Bootstrap My First Company

Nicolas Cole

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Jul 30, 2020 · 2 min read

Short post:

10 things I did to get Digital Press off the ground (eventually growing to 20 full-time employees, 60+ clients, and 7-figures in revenue):

1. I paid my co-founder a salary for 5 months so he could quit his job and take the leap with me (he’s since paid me back).
2. I ghostwrote 5–8 articles per day for various freelance clients, 7 days a week, for those 5 months — to make sure we both could eat.
3. I flew from Chicago to Atlanta once or twice a month for a year straight, so my co-founder and I could work together in the same room (and he flew to Chicago just as often).
4. I slept on couches in Los Angeles so I could be exposed to what “entrepreneur life” was like out there (I have since moved to LA).
5. I offered my services as a writer for free to as many big-name business leaders as I could get in contact with, even when I was already charging a premium for my writing services. Many of these free deals ended up leading to clients or massive opportunities for the business.
6. I invested a significant amount of time, energy, and money into building my personal brand online, and said yes to every single podcast request, guest blog request, and speaking opportunity, regardless of how packed my schedule was and how small the podcast or site was. (These efforts are a big reason why the SEO for my name is so ridiculous — sooooo many backlinks.)
7. Even after we landed our first few clients at Digital Press, I continued investing hours into writing my own content and building my own personal brand. To date, we still haven’t spent a single dollar on paid advertising — my personal brand drives more than enough opportunity.
8. My co-founder and I built our entire internal culture and workflow around lessons I’d learned playing in some of the most competitive World of Warcraft guilds in North America (Slack = guild chat). This allowed us to stay entirely remote, keep overhead costs low, but recruit really talented people from anywhere in the world and allow everyone to live that “laptop lifestyle” while still feeling engaged and part of a tight-knit company.
9. I packed up all of my belongings and drove 2,000 miles to Los Angeles to be part of a more competitive entrepreneurial ecosystem than Chicago (I love Chicago but LA is on a different level). That move has since catapulted both the business and my own growth as an entrepreneurial.
10. I spent 4 years building a personal brand that allowed me to start a company and immediately be able to make it profitable and successful.