On Big Decisions


The phone rings. It's another entrepreneur. It's another pitch. It's another story. And I have a list of questions, a series of doubts and always a twinge of guilt. Why? Because even though I'm not entirely sold on this idea, entrepreneurs call me every single day - asking for advise, feedback or introductions. I'm happy to do it for each and every single one of them - if I believe their story. I feel guilty during most of these conversations because I have been through what they're going through. 

In an entrepreneur's life, there are usually 3 difficult decisions:

  1. When they give up comfort
    • Entrepreneurs are a rare breed of people - they are willing to give up everything to make themselves happy. That's the definition of an entrepreneur. They give up comfort of their current circumstances. They sacrifice relationships to form better ones. Why? Because it makes them happy. Here's the thing: for anyone to even think of these changes means that their current circumstances - professional and/or personal are wrong. But, knowing what is wrong and making the change are two different things. 
  2. When they have to ask for money
    • If you're dreaming, might as well dream big. When entrepreneurs do that, they need money - whether to pay rent or to pay salaries. You always do. And when you have to, your ego is hurt. It hurts going to people that told you once that you wouldn't make it. But, you have to put that in the rearview mirror and let it roll off of you. 
  3. When they're in an incredibly difficult situation
    • The biggest determining factor in success is making hard choices. And the only time you have to make hard choices is when you're in a difficult situation. You know what you do then? You rip off the bandaid. Just fucking do it. If you don't you're going to bleed internally. Or as Paul Graham from YC in an article perfectly titled "How Not to Die" says: "So I'll tell you now: bad shit is coming. It always is in a startup. The odds of getting from launch to liquidity without some kind of disaster happening are one in a thousand. So don't get demoralized. When the disaster strikes, just say to yourself, ok, this was what Paul was talking about. What did he say to do? Oh, yeah. Don't give up."

If you are comfortable with the 3 traits above, I'll tell you this: make the big decisions. Believe in your dream. You know why? Because no one else on this planet will. Not your partner. Not your family. Not even your employees. 

I've started a few companies. Some have liquidated. Others have not. But despite the outcome, I have yet to regret any of those decisions. Why? Because I believed in them and fought for them harder than I have ever fought for anything else. There's no point in fighting for anything UNLESS you believe that it is going to be longterm. 

And if you're not always fighting, then you're making short term decisions. Decisions for today. Not for tomorrow. And those decisions are never going to work. That's my promise.