Robert Frost said "two roads diverged, and I took the one less VCs travel on and that has made all the difference"...or something like that, I think?
There's a love affair with raising money. I equate this to an engaged couple over-obsessing over their wedding day. Have fun, enjoy the wedding, and then...you wake up the next day married. Many people are far too focused on the wedding and forget about the marriage.
Similarly, I find that a lot of founders romanticize fundraising and make it the ultimate startup badge of honor. I believe this is a grave mistake. They get so focused on raising that they forget they are building a company.
I'm very open about the fact that I don't ever desire to raise money for a business I launch - I'm a bootstrap guy to my core and I own it.
You know what makes doing that much more feasible? Income derived from something besides the startup. Whoa.
I don't want to over-simplify or minimize this. I know I'm suggesting that 1) You may work a lot to achieve this or 2) You may not be able to go as fast in building the startup as you'd like to. I am finding that these sacrifices allow me to increase the likelihood of succeeding at remaining bootstrapped for the long haul.
Eric Siu and Andrew Wilkinson spoke about building a "launchpad business" on a recent podcast. I suggest you listen to it, as it was a valuable conversation to sit in on. I actually engaged on a Twitter thread when Eric posted about this topic and said "Yes, exactly! I do this. Finally someone put words to what I've been trying to explain."
Having enough income to stabilize your personal financial life *outside a startup project is pure magic, and I'd like to see founders plan their endeavors around this strategy as opposed to banking on funding from an outside source.
Speaking of funding sources, I've been consuming a lot of content and thinking about non-dilutive funding quite a bit recently. Will write about that soon.