Envy all the way up

Justin Mares (my Traction co-author) wrote a post a few weeks ago entitled Entrepreneurship and Envy on how when you are starting out in startups "it can be easy to occasionally feel envious or jealous of others' success." He then goes on to explore a lot of mitigation factors that have worked for him, and I really encourage you to read them.

There are many levels of success (across any definition of the term), and there will generally always be people more successful than you in any endeavor. Successful startup founders are still not Mark Zuckerberg. Successful VCs are still not John Doerr
What's not obvious is that as you become more successful you actually increasingly meet and become friends with even "more successful" people. As a result, envious feelings can still easily become an issue after having a successful exit, and more generally they can occur all the way up the ladder.

I find that people who focus on money have a much harder time with this issue. It's too easy to measure against, whereas more holistic success is more subjective and as a result less comparable. The broader version includes lifestyle choices, what your day-to-day is really like, and overall happiness (both short and long term).

Of course money is naturally at the center of the startup ecosystem, so it is easier said than done.

ChuckMcM had a great comment on this subject on Hacker News a while back, talking about how for serial entrepreneurs, money buys fearlessness. Here's an excerpt:

A number of people I know seem to have various milestones for fearlessness, but they roughly correlate to:

1) they own their house free and clear,
2) they have enough money set aside for their kids educations,
3) they have enough money set aside to keep them in Ramen indefinitely.

Each level brings its own level of fearlessness.

Without the cushion from my last startup, I know I wouldn't have been fearless enough to do DuckDuckGo in its current form. At the very least, I wouldn't have been able to stomach going without salary for five years.

If you can re-frame the money portion of success into goals, then I think you can focus on those goals and less on other peoples' success. It also enables you to think more broadly about startup exit paths.

One problem with this approach is that as you move up, you can keep moving the goal posts. There are indeed more levels of fearlessness that generally require more and more money. The question is do you really need to get there and how much money does it actually take to get to some of these places.

I've talked a bit about my history of money, and I wish more people would as well so that these levels would be more transparent to people when considering exit scenarios.

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I'm the Founder & CEO of DuckDuckGo, the search engine that doesn't track you. I'm also the co-author of Traction Book, the book that helps you get traction. More about me.

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