Bootstrapping on the side is the best way to do it, so you can survive financially. I live off previous projects and consulting work while I try new side projects.<p>It sucks that you can afford less time on the side projects that way, but at least it's viable...
I think that unfortunately, the answer to this question is: it depends!<p>My $0.02 is that it depends really on the market size (based on your startups focus) and its growth. If you are early to a space then trying to grow your startup full-time will burn you out, and similarly if it is a large market that is not growing much you might need to work on it with a team full-time and put in a lot of effort to get market share.<p>My bias is to keep it on the side until you have a certain amount of product/market understanding. Doing that and having enough insights about your industry can take time once you start playing in it. Once that happens, and if you can make it happen, do a pivot as needed and double down.
I really hope you can bootstrap on the side, cuz that's what I'm doing and hoping for success. I am adding some extra probability for failure by tryin to do it 100% by myself. We'll see if i end up outsourcing, contracting or getting a partner, but for now, bootstrapping while being employed is proving to be a possible success for me.
DHH later responded to this post on Twitter:
<a href="https://twitter.com/dhh/status/1074688850054733824" rel="nofollow">https://twitter.com/dhh/status/1074688850054733824</a><p>He said:<p>> "Is it possible to build a startup on the side?” The answer is clearly YES. If you ask, is it possible for swans to be black, you just need one black swan to answer affirmative. And there are tons of built-on-the-side startup swans. The same with “is it possible to grow a startup on a sane 40h workweek”, the answer is again overwhelmingly YES. That’s completely irrefutably true by lots of examples. The only question is do I want to bootstrap as a side business? Do I want to have healthy work habits?"<p>Jason Cohen did a podcast interview after this article came out:
<a href="https://www.productpeople.tv/97" rel="nofollow">https://www.productpeople.tv/97</a>
<a href="https://www.productpeople.tv/98" rel="nofollow">https://www.productpeople.tv/98</a>