Embracing Limitations

I would like you to create something.  Go.

Wait… What? That’s not enough?  Well, you have everything. Go!

“I cannot,” you say, “I need more information.”


Life can be a shapeless blue ocean inviting you to do something. This can be terrifying. Instead of remaining frozen, or going immediately to someone else’s prescription, a practice I find helpful is to look for limitations and then embrace them.

Last Thursday evening I visited my sixth grade daughter’s Science Fair. Interspersed throughout the school, the teachers had setup activities for families. One activity was a challenge to build the tallest snowman possible. Participants were given 3 pieces of 8 x 11.5 inch paper, a very small amount of tape, and a rule that the bottom should be the largest surface area, the middle, an in-between surface area, and the top, the smallest surface area. It was fascinating to see the kids and parents go to work within these constraints. How would you solve it? My daughters and I built one that was 40 inches tall but it looked nothing like a snowman. That was not one of the constraints. Ours had no arms and was VERY skinny… but very tall!

Business functions a lot like this for me. There are a few rules… a few limitations. I seek them out incessantly and then imagine a tall snowman with limited resources. How do I construct it? At Little Engine Ventures, I have a great number of fantastic people. Each weld tools and experiences unlike my own. How do I equip them to excel? We have a lot more capital than most people, but far, far less than many others. We have our limitations, how do we construct something magnificent with what we have? The challenge is big but the limitations are real. They’re not excuses, they are rules of play. Each of our portfolio CEOs are also given constraints. There are a few simple rules and a lot of freedom. Yesterday a friend asked me how much vacation time I give our CEOs… I don’t give them any. They take as many as they need.

I fundamentally believe that limitations are useful for the play of the game. But a number of limitations in life and business can be altered if you have a long enough timeline. In fact, some limitations are actually massive benefits. A giant cannot walk on thin ice. Embrace your smallness.

People and cash are two excuses I often hear from the sidelines of wannabe business owners. Fortunately, I learned early on to consider these limitations as moldable. They are real but not static. In 1975, Harvard professor, Howard Stevenson defined entrepreneurship as “the pursuit of opportunity without regard to resources currently controlled.” I believe the key word in this sentence is “currently.” There is an aspect of timing that cannot be ignored. I started with nothing. I literally started by by mowing grass and using the cash to buy CDs to sell on the school bus in the early 1990’s. It’s been a game I’ve enjoyed ever since.

Another way to approach limitations is to imagine them as non-existent. Over a long enough timeline there are no limitations. Today’s limitations are those you chose to accept. Choose carefully. And, attempt to turn all these current limits into assets for you to weld. If you own an illiquid long term asset and need cash, consider selling it. Problem solved. If you own nothing but have time, go to work. If you don’t have time but are alive, start cutting out time sinks, or start hiring people that have time. Don’t know how? Learn.

I didn’t know anything about starting a fund in 2015. But, I knew how to buy and run multiple businesses at a time. I am also a fast learner. My wife and I agreed to put a limit on how much cash I was allowed to invest in my next project. I embraced the limit. I cashed in on some hard earned trust from friends and family and invited them to join me. I delivered results. I invited more. Cash limit gone. (well, kind of…) At this point, I think the only limitations we have are self imposed… and there are many. One of which is my desire to be the largest single partner in the fund. It lets all of us sleep a little better. There is no reason to enforce this to the grave but it will take a special partner for me to become comfortable with allowing our center of gravity to shift so early in the building of our culture. Fortunately we are obscure enough that no giants are interested in our tiny boat in the backwoods fishing holes we frequent.

I think a true leader is someone who can select the limitations needed for positive game play. Introduce a vision or challenge. Invite people to join you and excel. Be the best version of you. Drop me a note if I can help… or if you see a massive flaw that I am overlooking an email clarifying that would be even better!