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Tuesday, August 9, 2022

Short Life Lessons From Kirk Drake

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Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Southern California and my dad moved his company to Oregon when I was 14.

My parents were mostly working and weren’t around much – I spent a lot of my childhood meeting neighbors and starting small businesses.

My parents were not very good with money and I constantly felt like I couldn’t rely on most of the adults around me. It caused me to drive for stability and financial freedom from as early as 7 or 8.

What is something you wish you would’ve realized earlier in your life?

I wish I had learned how to know when to gracefully end things and how to have hard conversations much earlier.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

In 2013 we lost our largest client – 40% of our business – went under overnight. A few years earlier we had done an owner-financed acquisition. The seller flipped out and called the note when the client went out of business. I spent the next 2 years unwinding all of the “spinning plates” or “hairy deals” that I had done and began to focus on building a really “good” organic business with a great value proposition.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Every dollar I have spent on coaching, leadership, emotional intelligence, and personal growth has been returned. I don’t believe you can invest too much money or time in developing your skills.

What is your morning routine?

I wake up at 5:30 am, go to Orange Theory Fitness. It’s a twenty-minute drive – I make a call to someone on my team and catch up. Then I work out and join the morning huddle as I walk out of class. When I get home – I shower, eat, and head to the office.

On Friday night I use the productivity planner and plan the entire week in advance and block out my schedule. I use the book “When” to determine which work I do at which part of the day.

What habit or behavior that you have pursued for a few years has most improved your life?

Once a quarter I sit down and spend time determining what is working, speculative, and isn’t working. I ruthlessly kill off things, pet projects, interesting things, etc. I try to always be weeding and getting more focus.

What are your strategies for being productive and using your time most efficiently?

  • Productivity Planner
  • Pomodoro
  • Timeboxing
  • Blocking off time on my calendar
  • Assistant Playbook
  • $100, $1000, $10000 time assessment

What book(s) have influenced your life the most? Why?

  • Double Double by Cameron Herold was the first book I read a few years after becoming an entrepreneur. It helped me identify as an Entrepreneur as well as has a ton of great business wisdom.
  • Pumpkin Plan by Mike Michalowicz is a great book on focusing on the 20% that is the 80% of your business. It was helpful in moving from every customer being a good customer to really knowing how to find the right fit.
  • First Break All of the Rules by Marcus Buckingham – was the first management book I read after becoming a manager. Its insights into managing people and building great teams helped me figure out how to connect and lead a team.
  • Influence by Robert Cialdini – the Psychology of Persuasion was a great marketing book

Do you have any quotes you live by or think of often?

  • “Fail fast, fail forward, and fail cheaply.”
  • “There’s no shortage of remarkable ideas, what’s missing is the will to execute them.” – Seth Godin
  • “80% of success is showing up.”



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