Startup Diaries: Incredible Life (and Business) Lessons I Learned in My 20’s

In my twenties, I learned several things about life (and business) that all entrepreneurs can benefit from.

I look back on my twenties with no regrets. There was no shortage of good times, but like many of us I made a lot of boneheaded mistakes. I believe all experiences, good or bad, happen for a reason. People come into and out of our lives for a reason. Yet it has only taken me about 30 years to figure out that the reason is simple: Everything happens so that you can grow as a person.

Yet, our instant gratification culture has made it easy to forget that who you are isn’t an instant thing, but a long evolution of learning who you can become as a person over the passage of time. In my twenties, I learned several things about life (and business) that all entrepreneurs can benefit from:


  • Stay in constant pursuit of mind blowing experiences.

    It wasn’t until I had the honor of being a godfather that I realized this important lesson. For example, my goddaughter is now a few months shy of 2 years old, and when she walks into a room she always has an expression of pure awe on her face. It’s like she’s thinking, “What amazing things can I learn about in here?” Then again, she could be just wondering if I have animal crackers.

    Yet, I’ve found that I too want to learn something every single day. I want to meet other entrepreneur’s with life and world changing ideas and enough passion and ability to actually execute it. I want to travel the world and embrace other cultures. I want to share amazing experiences with the people I care about, experiences that can only be described as mind blowing.

  • Relationships are everything.

    I grew up hearing “You’ll get more done on a golf course than you will in a board room,” and it has always stuck. I’ve learned that things — whether in business or in life — get done because you have a relationship with someone. You treat them as a partner. Sometimes you have to give before you get. But you work with each other because you’ve found a common bond that brings you both together.

  • People are just people.

    I’ve had the opportunity to do some pretty cool things so far in my life. For example, I helped start an arena football team, worked five years in the Kansas City Power & Light District entertaining thousands as a DJ, and helped start Think Big to change the way people build companies. Through all of this I’ve gotten to meet so many different people, from many different walks of life.

    However, I’ve learned that no matter the wealth, fame, social status, etc., people are essentially the same. Everyone is worried about the same things — family, money, jobs, and relationships. They want to fit in, feel cool, and be important. People all have anxieties, stresses, and insecurities that plague them. People are just people, not any better (or any worse) than the rest of us.

  • Don’t waste time on people who don’t treat you well.

    People are just people, but don’t tolerate people who don’t treat you well. Period. Don’t tolerate them for financial reasons. Don’t tolerate them for emotional reasons. I’ve learned that good relationships are hard to come by, but there’s still no shortage of people to meet and friends to be made. There’s no reason to waste our time with people who don’t help us on our life’s path.

  • You should definitely take risks.

    Unless you are already dead  —  mentally, emotionally, and socially  —  you cannot anticipate your life five years into the future. It will not develop as you expect. So just stop. I’ve learned that taking a risk is a powerful thing. If an opportunity presents itself you should take it. If you’ve been dreaming of starting a business you should just do it. Whatever the risk is, the worst thing that could happen is you fail and don’t learn from your mistake.

  • Money shouldn’t drive you — experiences should.

    Sure, money makes the world go round. And when it comes down to it I want to make a lot of it. But to me, money is just a means to experience and create more opportunities for them. Personally, I’m more interested in shared experiences I can have with others than material things. For instance, have you ever gone on a trip with someone and had one of those mind-blowing experiences that nobody would get unless they were there? You could go years without talking to that person, then meet up and it’s like you never skipped a beat.

    I want more experiences like that, with more family, and more friends. As an entrepreneur, I want to make money so that I can fund more businesses. There is nothing like being a part of building a product or service that impacts millions of people’s lives every day. But I’ve learned that money is a means. If you can make it while doing what you love you should do so. If what you love just so happens to create once-in-a-lifetime experiences, you should do more of it.

  • Never stop asking questions.

    Can you believe that people actually thought the world was flat? How about that Pluto used to be a planet? These were universal truths that everyone believed as fact. It turns out not all facts are actually true. We know that because people kept asking questions and challenging common beliefs. I’ve learned that to really grow and evolve as a person you must always ask questions. You can never stop challenging your assumptions about how things “just are.” And you must learn to accept that sometimes things just change and you have to grow with it.

  • You need to take care of yourself.

    Four years ago I weighed 208 pounds. I was fat and I hated who I had become. I was always tired and sick, but also sick and tired of being this way. So, I made a decision that year for a life change. I figured if you can’t have control over this one thing in your life — yourself and how you feel about yourself — then how do you expect to be a leader and help others? I needed a lifestyle change.

    I needed an attitude change. I’ve lost almost 50 pounds since then and learned that if I want to achieve the things I desire, and help others, it all starts with me. And taking care of yourself, both mind and body, plays a major role in that. Quit making excuses about why you can’t make it to the gym or why you’re eating poorly. Your body is a machine and you should treat it that way.

Turns out that the common thread that holds all of these lessons together is to never stop learning. So, here’s to the next 30 years.


This article has been edited and condensed.

Blake Miller is a Partner and the Director of the Accelerator at Think Big Partners where he focuses on helping entrepreneurs build, launch, and grow their company. He specializes in Growth, UI/UX, Innovation and connecting the dots. A version of this post originally appeared on Medium. Connect with @ImBmills on Twitter.


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