When life changing money, isn’t…
Wil Reynolds

Great post, and I agree with a lot of it, but the parts I disagree with are going to keep me up at night so I feel compelled to make a few quick points (and then go back to fixing some bugs):

  1. Creating options for yourself doesn’t mean that you’re going to use those options in toxic ways. My guess is that compared to where you were before, you can afford to do a lot of things — like eating out every night. But you don’t do them. Why? Because that’s not who you are. Even if you put a bunch of money in your pocket, it doesn’t necessitate you stop being who you are.
  2. How many startups have you come across that you would have loved to support and invest in? Turns out, having money allows you to do that — and it’s both gratifying and fun.
  3. I’ve probably talked to over a hundred entrepreneurs at this point. I don’t think I’ve ever come across one that had exactly one idea and one company and would never do anything beyond that idea/company ever again. And, most of them loved what they were doing and the company they had.
  4. Like you and me, there are many people that have hit their “enough” point a while ago. Yet, they keep pushing. They’re not all money-hungry schmucks. They’re not all trying to put points on the money scorecard. There are other possible reasons — one just being raw impact.
  5. I’m in full support of having a team of people around you such that you are not the final escalation point. As it turns out, becoming part of a larger company increases the chances of that happening, in most cases.
  6. Distributing ownership interest across your team is a great idea. Not doing so is one of the many mistakes I made in my first startup — but fixed at HubSpot. Pro tip: Profit-sharing is not the same as actually distributing equity. There’s a psychological difference, and it’s an important one.

I commend you on your self-awareness. But, recognize that false dichotomies are exactly that: false. Most of the areas you’re exploring are not simple, binary choices. It’s not: a) you are either content with what you have or b) You’re a scoreboard slave. It’s not quite that simple — few things are.

Having said that, I have the problem that so many others have: I tend to rationalize my own choices. The only difference is, I’ve done it for a lot longer, so I’ve had more practice. :)

Onward and upward, my friend, for your own definition of upward.


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