Wise Up: 12 Lessons Learned From a 2011 Entrepreneurial Journey

Yesterday I posted a long commemoration of my entrepreneurial journey in 2011. Buried at the bottom of the post were 12 lessons learned from the last year. A few friends recommended I repost them as a separate post in order to properly highlight them. Here they are in case you didn’t catch them.

Every experience holds both positive and negative. The last year had many successes but also many tough times. At some point over the last year, around May or June, I reached a point of stability and confidence in my own ability and identity that even the negatives times started to be seen as opportunities for growth, rather than maladies to be avoided. Setbacks were simply feedback on my performance, fodder to improve next time, not an indicator of self-efficacy or self-worth. But even when I learned my lessons, the new performances were always less then perfect. This fallibility needs to be accepted.The cycle never stops. There is always more to learn.

Before I close, I wanted to share a few more lessons learned from the experiences of the past year.

Lesson 1: What are you going to be when you grow up?

We experimented with so many different ideas and approaches over the last year. I feel like I learned the discovery process inside out. It’s a very important and valuable process, but I think the possibility space is a lot more constrained than people’s intuition lead them to believe. When starting something new the possibilities for what the project could become seem infinite, but ultimately there are a limited number of models that can scale into something with high impact. However, if you’re willing to entertain building something niche, there is access to the much wider possibility space along the long tail. Given our mission of finding a scalable way to increase the success rate of startups, there were really only 4 viable, scalable ideas that we uncovered: A Software Company, an Investment Fund, an Educational Media Company and a Research Institute. Bjoern and I decided to the Software Company.

When I see nascent ideas now I almost always ask myself, “from the viable models I’m aware of, which one could this project be when it grows up?

Lesson 2: Patience—Don’t Bite Off More Than You Can Chew

It’s important to have a big vision, but it’s equally important to get started right away. Creating something from nothing is really, really hard. When you have as little resources and as limited time has startups do, it  requires extreme focus. All of the big things you want to do can be done eventually as you get more momentum and resources. But that will only happen if you focus successfully first.  If you do it right eventually, your baby will eventually grow into the world as an organism with a life of its own, with the power and energy to pursue crazy ideas like Space Elevators and Autonomous Driving Cars. But that takes time.

“A man who is a master of patience is master of everything else”

“Patience is not about how long one waits; patience is about how well one behaves while they wait”

Lesson 3: Entrepreneurship as a means of Self Expression

Entrepreneurship is not for the faint of heart. It is a life encompassing sport full of trials and tribulations. But if you dare to embark on the perilous journey you will find an opportunity like little else for authentic self expression, self discovery, and world altering impact. Commit to preparation, commit to learning, and when the time is right, don’t forget to leap.

Lesson 4: The Power of Ideals and Vision

Blackbox as an idea and ideal was something that was very powerful and resonated with a lot of people. Its descendant projects possess the common thread of passion for empowering entrepreneurs, belief in the power of data to improve decision making, and a desire to maximize human potential.

Lesson 5: Startups Are Not Efficient

Startups do not run like a well oiled machine. They stop. They start. They break. You have to find new parts. Those parts end up being out of stock and you have to make them yourself.

This requires a lot of patience, perseverance and expectation management. If you expect to hit cruising altitude right away you will just become frustrated and demoralized.  It’s rare a founding team has everything they need to start firing on all cylinders right away. The process is much more like jumping off a cliff and assembling your parachute on the way down. Despite all this inefficiency startups can be very effective, because they have something other organizations don’t: Freedom.

Freedom from conventional thought. Freedom from bureaucracy. Freedom to explore and create their iconoclastic vision of the world. And the vision doesn’t need to be perfectly realized right away, just getting something working is often enough to begin drumming up the support, momentum and resources necessary to accelerate into maturity.

Lesson 6: Don’t Project Your Ambitions on to other People

Founders have to be irrationally optimistic and their enthusiasm often inspires other people to want to join them, and for them to want to include many people in their vision. They need to be careful not to project idyllic views on other people, and expect them to live up to unrealistic expectations. There will just be hurt and disappointment on both sides.

Lesson 7: Select The People You Want To Work With Carefully

Only select people who you believe are great now and have potential to be even better in the future. Don’t hope that a B or C player will grow into an A player. You only want A players who can become A+ players.

Lesson 8: If Your Startup Is Done Right Your Cofounders Will Become Your Best Friends

You don’t have to start out as best friends but it should emerge over the first year of working full time. If you’re doing your startup right you will inevitably create a stronger bond with your cofounders than any of your friends. You have to put everything on the line to succeed. Not only do you burn all your boats at the shore, but you are dependent on high performance from your cofounders to survive. This requires an enormous amount of trust to be able to march ahead confidently. Over the last year Bjoern and I lived in the same house and spent almost every waking hour together and discussed nearly everything on our minds, from personal to professional. I wouldn’t recommend it any other way.

Lesson 9: Don’t Work with People Who Can’t Evaluate Their Own Value

If they can’t evaluate their own value they won’t be able to evaluate your value or anyone else’s. Whenever pies are split or credit is taken, there will inevitably be conflict.

Lesson 10: The Learning Curve For New People is Longer than You Expect

Expanding the team can accelerate growth, but there are very high initial costs. When you add someone you will probably move slower for the first weeks, maybe even first few months. It takes time for them to get acclimated with the project and your working style. Take on your first few people slowly, and know you will lose more than you gain if they don’t stay long term.

Lesson 11: Success Carries a Burden of Responsibility

The more momentum you gather and the more success you have, the more responsibility you carry for others. People put their faith in you, users rely on you, and employees depend on you. This burden of responsibility should not be underestimated. Living with integrity is all the more important.

Lesson 12: Having the Flexibility to Let Go

In the course of starting a company many projects and directions are explored. It is as important to have the ability to let go as it is to be able to persevere.

In Finale… I Would Stand In Line For This

I write this from The Glint looking out over the expansive San Francisco skyline and can’t help but get excited about what 2012 has in store for us all. It’s going to be a big year. Happy New Year my friends, stay hungry and make the most of it. This is just the beginning.

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Related posts:

  1. The Disbanding of Blackbox And The Birth Of The Startup Genome: Lessons Learned From A 2011 Entrepreneurial Journey
  2. Reflections On Finding My Passion And Early Steps In My Entrepreneurial Journey