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I quit my job to start a startup while having a family and kids and I consider it a mistake. I’m not sure it would have changed the outcome (successful exit) but it caused a lot of extra stress, and I can safely say that I didn’t quite know what I was doing and it would have been better to have a stronger plan (especially marketing), a longer runway, a more complete prototype, and more evidence of a market, before I took the leap and quit my job. All those things can be done on the side while holding down a job, even with a family. (As long as the job is closer to 40 hours a week than 60 or 70...) $1M is a nice runway, but most people don’t have that, and even with it, the more you have locked down before you quit your job, the better.



I think more than just money, you have to account for your "mistakes runway".

You WILL make mistakes - a lot of them if its your first business.

When you are 25, you just have a lot longer runway to make those mistakes.

At 35 with a wife and kid, you have limited time to make mistakes and learn from them


Absolutely true. I heard that before starting and (of course) didn’t understand what it meant. And we were optimistic, so we discounted it, assuming we were starter than the average Joe, so we wouldn’t make as many mistakes. Nope, we made mistakes that could be counted in units of years and hundreds of thousands of dollars. And broadly speaking, yeah, nearly everyone does when building companies. The thing that never occurred to me that you put nicely is that you have a finite mistake budget, and you don’t know what it is.


Amen.

I think your story is important and why I think we should be pushing people more to this sort of arrangement.

Even VCs will never give you a penny without first quitting your job, but honestly some of the seed stuff I don’t see why one couldn’t do both if there is promise.


Speaking of VCs, part of not knowing what I was doing before I quit my job was not understanding how VCs worked, and how much evidence they need before investing. They spend a lot more money on companies that have $1M/month income than on seeding unknown first timers, even seed funds. There are too many misleading stories of cash being thrown at startups with nothing more than an idea. Maybe it happens once or twice in a blue moon, but the reality is that they prefer a sure thing and don’t often fund companies with no traction. It took a lot longer to raise money than we expected, even after we had what we thought seemed like good traction. And when it takes longer to raise, it means you need a longer runway. It took longer to build than we thought too. I was very lucky to have a couple years’ runway, and it still wasn’t nearly enough, I should have planned on 3 or 4 times as long.




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