Are You Prepared for the Real Costs of Being a Startup Founder?

It’s more expensive than you think

Aaron Dinin, PhD
The Startup
Published in
4 min readNov 17, 2022

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Photo by christopher lemercier on Unsplash

I’ve got a friend who’s in an on-again/off-again relationship with a woman he’s been dating since college. It’s a never-ending source of drama for him, but a wonderful source of entertainment for me. Unfortunately, it’s also a constant reminder of my own tumultuous relationship. The relationship isn’t with my wife, with whom I’m coming up on a happy 13th year anniversary. Instead, my tumultuous relationship is with entrepreneurship and building startups.

Every time I finish working on a startup — whether because of a successful exit or an epic failure — I’m liberated. It’s as though I’ve had an enormous weight lifted off my shoulders, and the feeling of being free of all the stress and drama is incredible. In that moment of relief, I act exactly like my friend every time he escapes his toxic romantic relationship; I promise myself I’ll never do it again.

But, also like my friend, it’s never true for me, either. I’m too addicted to the drama of building startups, and the drama eventually sucks me back in.

At first, the temptation is subtle. I’ll be happily enjoying my startup-free life when I accidentally notice an interesting problem or a cool new technology. As soon as I do, the familiar entrepreneurial…

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Aaron Dinin, PhD
The Startup

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com