Lessons Learned From a Life-Long Career of Start Ups and Daydreaming

Dale Russell, Talksum CTODale Russell, CTO, Talksum

All of my life, I’ve been doing things differently. Back in the 70s and 80s, this was not a trait that my teachers really appreciated. I bet I was told to stop daydreaming every half hour or so, and I’m sure my parents received a note from the principal almost every other week. Amazingly, my father, who was a rather strict man, would never say anything about it as long as I kept my grades up. He would tell me every day that my life would be a series of those dreams, that when I’d reach one dream then a new dream would form, and that when I failed, it was most important to dream yet another dream and try to reach it.

I didn’t realize until recently that it is my father’s fault that I have always been like this.

Over the years in my career, I have been very fortunate to have mentors who took the time to give me crash courses in whatever I needed to know along with the confidence to execute. A couple of months ago, I reached out to one of those mentors, who is now an Algebra teacher in Florida. I am sure he thought I was crazy, but truthfully I would not have had the same career had it not been for his mentorship. It was more than just what he taught, it was more the freedom he gave me to experiment, to fail, and to learn on my own. I mention this person because years later, in retrospect, I think he is still teaching me a lesson, or maybe I am truly so hardheaded that it took 16 years for it to sink in.

So, here’s what I have learned and what I can apply from these “lessons.” Teach and mentor, but most importantly trust your team to learn from you. In a start-up company, everyone in the company can attend an all-hands meeting at one conference table to discuss strategy. This is my greatest dream – to be a better teacher to all of those around the table. There are no simple rules of success for any start up. Most products will fail; hockey-stick business plans are useless. The ability to mentor a small group of brilliant people, and teach them what to do as you’re doing it is an imperative. If what you’re doing is truly innovative, it is incumbent upon you to impart the knowledge and confidence in them to enable them to contribute in the company’s success.