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16 Lessons Learned From My Entrepreneurial Journey

16 lessons learned from my entrepreneurial journey

So as we reached the sweet 16 birthday of my company, I wanted to share 16 lessons I’ve learned along the way of my journey as an accidental entrepreneur. Ready? Here we go…

If you prefer to watch instead of read, check on the video version here.
  1. If you think you aren’t ready, You’ll always be right. The only way you’ll know for sure is if you just start.

    1. In 2010 I was 30 years old, married with two kids, two cars, a mortgage and almost no savings when I decided that I should probably go into business for myself after taking a flaming parachute out of the bust. To say the timing wasn’t ideal would be a pretty serious understatement.
    2. How did I know I was ready? Well it took about a year after I started until I realized I had been able to support my family on my own and had completely replaced my previous salary as a CMO. I guess I was ready after all and it was too late to stop then.
  2. When your focus is on taking care of other people’s needs first, they’ll be there for you when you really need them.

    1. When I started my business the first people I called were all of the people I had ever worked for and most of them became my first clients. These were all people whose companies I had quit. And I still call some of them clients today.
    2. So I just follow this simple life rule – Give first, expect nothing, trust the universe.
  3. In the beginning you can and should do all of the jobs yourself, for a little while. It will help you figure out where you add the most value.

    1. Then figure out the parts that you’re not good at, and don’t like, and then hire smarter people to do them instead. It took me a few years, and I was scared out of my mind, but the first person I hired has worked for me for 12 years and now she’s my COO. Special thanks to my coach, Linda Hampton for that advice.
    2. Speaking of getting help make sure you get outside advisers to help you see the things you can’t. A coach, a peer group or a mentor – maybe all three!
  4. Spend the time to figure out what your mission, vision and values are.

    1. We sat in a makeshift kitchen & conference room with 4 people and my coach for hours and we started with 10 core values. But don’t settle working on them until they’re just right. In the end we found the 5 that have guided us for years now – Expertise, Prosperity, Innovation, Collaboration and Integrity.
    2. Once you get it right and create a culture around them, it will help your team know how to act when you’re not there.
  5. Don’t just do great work, be great to work with. Everyone in your company is in the sales department.

    1. Delivering bright ideas and brilliant results is expected. Doing it while earning trust and respect is what separates good companies from great ones. I didn’t read that one in a book. That one came from my parents. Your children are listening too.
    2. At the end of the day it doesn’t matter what you promise, it’s how you deliver and that makes every employee a part of the sales team.
  6. Not going out of business is not a business plan. Doing that leads to owning a job instead of a company.

    1. I spent the first 10 years running my company like it was an extension of me. Standing on a cliff in Positano, Italy it hit me. I realized that my business owned me.
    2. So figure out what your plan is and keep updating it as you go, but have a plan and share it. It will give you and your team a great sense of purpose.
  7. My company has grown the fastest when I have grown the most as an individual and leader. 

    1. Learn about yourself and what your strengths and weaknesses are. Then start “unlearning” what you think you are capable of. Each of us has a self imposed ceiling of what possible and it’s not unbreakable.
    2. If you need practice, go volunteer to be a leader elsewhere and bring back what you learn to your company. I have served on the board of the Entrepreneurs’ Organization for more than 5 years – and now I have the privilege to serve as my local Chapter President for 190 fellow entrepreneurs. Hey, maybe it’s just a coincidence we’ve been an Inc5000 company for the past two years.
  8. If you’re growing, there will be no shortage of problems. Just make sure you’re not working on the same ones over and over again. 

    1. Do we have issues? Oh yeah by the truckload. We started write them down, prioritize the big ones and give them back out to our team to knock them out. It’s called getting traction and there’s a great book on it from Gino Wickman.
    2. So go become an issue munching machine and create a culture that chews them up and spits them out. You’ll innovate faster and move mountains along the way.
  9. Spend the time to find great people to work for you. 

    1. Then make sure you trust them to do the great work you hired them for. One of the hardest lessons for most leaders to learn is to trust the team you rely on. Otherwise, why hire them?
    2. The lesson I continue to learn, is to spend as much time as possible to train and empower them. You’ll find yourself with the freedom to turn around and see the next mountain you need to climb together, instead of just wandering around putting out fires.
  10. The bottom line matters much more than the top line.

    1. For years I loved watching the the top line revenue of my company grow. But I realized that If you don’t take care of the bottom line first, then the only thing you’ll ever feed is your ego. Thanks to Greg Crabtree for that nugget.
  11. Being decisive means you’ll make a lot of decisions and most will be easy, but don’t avoid the difficult ones.

    1. Many decisions can be made that provide winners on both sides but some are just impossible to reconcile. When I’ve been faced with those I trust my instincts to tell me the right choice.
    2. When you have to communicate a difficult choice, first get clear about how your ego wants to take over and just check it at the door. It still won’t be an easy conversation but at least you won’t be fighting with yourself also.
  12. Be great at something, but not everything.

    1. In the words of Harvard Business School professor Dr Frances Frei, when you focus on being great at one thing and you can afford to suck at something else. Try to be great at everything and no one will remember you.
    2. Once I got clear about what we were great at it also made it much easier to say what we were willing to not be great at. We created LocalLight, a new division of our company around this very idea.
  13. Don’t bother making a one year goal unless you also have a 10 and 25 year goal.

    1. Nothing crystalized what I should be working on each day better than when I created a 10 year vision for my life. It underlined my purpose and made daily choices far easier. If a new opportunity presents itself, I just hold it up to the 10 year plan and see if it’s part of that vision or not.
    2. The next milestone that blew my mind was to seriously think of my life in 25 year timeframes and to create goals, informed by my values, that made me realize I was still playing too small today.
  14. Getting clear about Why I was in business has helped me make better decisions everyday. What’s your purpose?

    1. Simon Sinek nailed it with his TED talk, it starts with Why. The most valued brands in the world figure out there Why? before they think about the How and the What. We help brands shine. Everyday and we can do that forever. We’re passionate about it, it’s in our DNA.
    2. But it’s more than just your company’s why. It’s about YOUR why. Why are you alive? What’s your one purpose? Mine? To Be of Service and to add Value.
  15. A business is just about numbers. I’ve always preferred to run a company, which is all about people.

    1. The numbers are there so we can keep score in the game. It’s still the players on the field, the coaches with the plans and the fans in the seats that all make the game worth playing. Winning a Best Places to Work award was the single proudest moment I’ve had in 16 years as an entrepreneur.
  16. Never stop learning and being curious about life.

    1. All of this has led me to realize that there’s no end to what’s possible for myself and my life. That is unless I stop asking the question that has guided me my whole career… What if? I can’t say I have all the answers, but I’m willing to learn and share.
If you’re keeping count we’ve reached sweet 16. To be honest, I don’t know that I’ve shared anything particularly new here. But who knows what ideas it might spark in you. So I want to know the best lesson you’ve learned along the way. Please share yours and let’s see what’s possible together!
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