6 Years and Lessons of Entrepreneurship

This month, I celebrate six months of full-time entrepreneurship as I started iThemes in January 2008.

I thought it was time for some reflection on what I’ve learned so far and to update some thoughts.

Here are 6 some lessons I learned from 6 years of entrepreneurship:

  1. Be relentless about your own happiness — AND those on our team and in your community. There was a season of time where I thought working anywhere else on the planet would be better than being at iThemes. But after a few months of misery, I vowed never to be that miserable again and I took action. Today, I’m more focused and driven than ever before to ensure long-lasting health and happiness for myself, our team, our customers and our business. I won’t let anyone or anything get in the way of this. I am the guardian and the protector of our happiness.
  2. Your success can make you afraid of heights — Like many other businesses, we’ve won awards, gotten accolades, been patted on the back a number of times. For the first five years, I just had my head down, pounding away, building the business … and then last fall I felt like we had been on this rocket ride of a journey for a long time and finally looked down to see how far we had soared. And it scared the crap out of me. For a time, I lost my confidence and boldness. I got afraid of heights. I got afraid of our own success. It can make you scared and insecure because there is more at stake now. One of my mentors challenged me to embrace our success, not run from it. We got here because we stepped into the unknown void and created our future. We didn’t let it come to us. We didn’t wait for someone else to hand it to us. We got here because we embraced the uncertainty and the challenge. We ran into it, not away from it. So after I wallowed in my fear for a time and got lost in it, I stopped looking down … and simply looked ahead, again, to the stars, the sky, the future. And I got my confidence and boldness back. I got my energy and enthusiasm back. I saw our future and it is bright and beautiful because I know we’ll go as far as we’re willing to go. So no looking down anymore. We have an uncharted territory to pioneer and a future to create for ourselves.
  3. The best reward from entrepreneurship isn’t money, it’s STILL the people — I would do it all over again to work with the awesome people who got us here. I would do it all again just to work alongside them and see their greatness blossom. The richest reward of my life has been the relationships I’ve gained and grown through this business. The solid gold people who love and care about you, who commit their time, talent, and support to the mission make you so much better. In fact, sometimes I want to tell people I’m really a fraud … the amazing people around me make me look better than I really am. The sum of our group’s efforts and talents is bigger and better than any individual. At the end of the day, we GO FAR TOGETHER. #BOOM
  4. Always be experimenting and taking little bets — If we hadn’t taken a couple of bets four years ago, we would not be here today. Some might call them risks. If anything, they are calculated risks. We took some bigger ones last year and we’re taking more this year. But I know the day we stop experimenting and taking little bets, trying new things and learning, is the day we start the slow decent into failure or worse, mediocrity. I’d rather fail than be mediocre. 
  5. Good partners who share your values, vision and purpose are invaluable — Almost all of the partnership stories I hear from other entrepreneurs are negative and typically have horrible endings. Each year for 6 years, my partners in so many words and actions have reassured me why they are the best partners I could have ever asked for. They are cheerleaders, encouragers and helpers. They are enablers. They want us to go far. And without them, I wouldn’t be here today. When my personal life had cratered a few years back, they were some of the first to be there for me as friends first. Now as I’ve experienced some of the great joys in life (like a son), they are the first ones to rejoice with me. They prefer to be rather anonymous, so I’ll say my thanks to them in person at lunch soon I hope.
  6. If my head ever gets too big, I hope my people (and they know who they are) pop it quick — I haven’t arrived and hope I never do. I hope I never start believing the awesome things people may say about me (however, grateful I am for their kind words). I’m still learning and growing, every day. I’m not the entrepreneur I want to be today. I’m not the leader, or the man, or husband or father or brother or friend, I want to be. I’m working toward being better and better. I’m not satisfied. I’m not content to stay here. The saddest thing I’ve seen is when people start believing the press and vapor about themselves. It’s the quickest way to loneliness. And success without people to share it with, who love you just for you, isn’t actually success. It’s an illusion of success … it’s a prison cell that’s filled with things that rot and rust but that can’t reach out and touch you, and hold you, and listen and with a mere glance say “I cherish you for you.” I choose people and love and life. 



2 replies on “6 Years and Lessons of Entrepreneurship”

Great insights Cory.

I can really relate to #2 and #4. I’m far from reaching the level of achievements you and your team have. But I’m farther ahead than where I was 3 years ago. I do find that today I’m slower to act and make bold (risky) moves than I used to be. But I have to remember it was the bets I made early on that got me here, and I have to continue to make bets and big moves if I’m going to reach the next level.

Thanks for the awesome posts lately. Lots to think about 🙂

Thanks man! High compliments coming from you.

Those two probably got compounded for me when we had our first child. 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *