7 Years of Entrepreneurship - Some Lessons Learned Along the Way

Seven years ago we co-founded our first company. We have founded 5 others since. Some have struggled and others have turned into something special. With the close of last year and the start of a new one, I have been doing some reflecting on some of the lessons I've learned along the way.

1/ Have good partners. I never want to be a CEO, but I always want to be a partner.

Great partners are the best leverage for a starting business, but they are also the hardest relationships to manage, so be picky.

If you can find a good partner, odds are you’ll find success.

2/ Give credit where credit is due. Odds are your employees are the ones that make your continued success possible.

Give them the respect and credit they deserve. If you lose the people that got you here, you might lose everything else too.

3/ Just do. A founder once told me that a good way to never be become an entrepreneur is to talk about it all the time. Stop talking about it and start doing.

Once you start, you’re going to find out really quick how good your idea is. The best time to start was when you first put the business plan together. The 2nd best time is right now.

4/ Equal is the best split. I’ve done a lot of deals and the #1 thing that causes them to fail is misaligned incentives. If one group wins big the other typically loses big. Short term this might be great for the winner, long term it’s unsustainable.

5/ The best deals are the ones you didn’t do. I know that sounds cliché but my god for me it’s been so true. Don’t kill yourself about the ones that got away. You’re better off. And even if you’re not better off financially you probably learned something you can use on the next one.

6/ Never mix ignorance and arrogance. It’s ok to be arrogant (sometimes) and it’s ok to be ignorant (sometimes) but being both at the same time is a receipt for failure. Plus, you’ll just be intolerable to be around.

7/ Try to get away from selling your time. It’s the most valuable thing you have and no one is ever going to pay you as much as it’s worth. Find a way to sell your service that isn’t tied to your time. You can’t create real wealth selling your time.

8/ Knowing what you don’t know is just as important as knowing what you do know. If you don’t have the knowledge. Find someone who does. Be quick to recognize and admit that you don’t have the answers. Make this automatic with every project you do.

9/ If you haven't been humbled in business, you should try it. It’s the best thing that can ever happen to you. Stay humble.

10/ Scaling is really hard. Especially when you are bootstrapping. I wish I had all the tips and tricks to scale but I think every situation is different.

For our companies it seems like we are always slightly too slow to commit to scaling. We're trying to get better. If you feel it in your gut that it is time expand, then it probably is.

11/ Capital can make or break you.

Remember once you take someone else’s money and give them control, it’s not your company any more. You’re their employee. So plan accordingly.

Bootstrapping has always worked out better for me personally. When we raise money now we try to do it as the GP.

12/ Network with people you don’t need anything from. The most powerful relationships are the ones that you forge where there is no transaction involved.

For me those relationships end up being the ones that some of our best deals have come from.

13/ Don’t listen to the haters. They want to tell you about how hard everything you are trying to do is going to be. They want to tell you all the reasons why businesses fail and all the risks involved.

They do these things because you are doing something that they probably don’t have the courage or competence to do. Don’t listen to them.

14/ Use media. It is the most powerful tool to reach people. I know it is outside of most people’s comfort zone but in the current doom scroll culture, if you are not consistently showing up in someone’s feed you are doing it wrong.

These are just a few thoughts as the new year starts.

I am going to try and start doing more writing this year. It is not easy for me. I have always struggled with writing and I’m trying to get better and plan to continue. Hopefully you pulled something useful out of this one.

Press on.