Starting My Company: Fear-Setting & Asymmetrical Risk

Fear-Setting & Asymmetrical Risk
(Reading Time: 3 minutes)

My positioning & strategy consultancy, Three Deuce Branding, turns 23 today.

I started it from the second bedroom of my Cincinnati condo in 1997. I run it from the second bedroom of our Chicago condo today. Progress!

Back then, going solo was less common than it is today. “I can’t believe you’re doing this” was a typical response – not always in a flattering way.

Some people even said I should try it part-time first, as if that were an option. (“I can help solve your strategic challenges, but only after 6pm.”)

I was all-in from the get-go. Today, I’m sharing some background on how I chose self-employment over a steady paycheck, since this is a question I get often. Fun fact: I made this decision in about 24 hours.

Continue reading “Starting My Company: Fear-Setting & Asymmetrical Risk”

12 Important Things I’ve Learned in 20 Years as a Soloist

(Reading Time: 6 minutes)On June 16, 1997, I declared myself “open for business” as a soloist and a brand strategy consultant.  I did this from the desk in my spare bedroom.  I don’t recall thinking, “I’ll be doing some version of this 20 years from now,” but here we are.

I’m very happy with how things have turned out, and I’m proud to have reached this milestone.  Below are 12 things I’ve learned along the way.  I hope they may be of benefit to those of you who are considering working for yourself, or are new to the game. Continue reading “12 Important Things I’ve Learned in 20 Years as a Soloist”