I lost about $300k (opportunity cost) bootstrapping a startup over almost 3 years. I burned up about $100k of savings (finance jobs before that) and was, at the end of it, about $15k in debt and, psychologically, in a really bad place. (It's actually pretty amazing that I didn't fall harder or sooner, living in NYC on about $3k per month.) Can't recommend that. Oh, and because I was the first to leave (because I literally ran out of money) and eat blame, the CEO refused to let me open-source the work I'd done, out of spite. Two years of what was then cutting-edge Clojure code (that was one awesome thing about the experience, being an early-adopter in Clojure) gone. (Most of it would be out-of-date now; the language has made impressive strides.)
Oh, and that Valhalla where after failing at a bootstrapped startup, you get hired as a Staff SWE at Google or an EIR at a venture firm? Doesn't fucking exist. Most startups leave your career in worse shape than you'd be in had you gotten a decent big-company job. (Emphasis on decent. Yes, bad big-company jobs waste your life and career and reputation, but so do bad startups and those are quite common.)
The second startup where I worked was VC-funded and paid a low but acceptable (savings-neutral) salary. I was there for 3 months. Hired as VP/Eng but disallowed to use the title (first warning sign) until 6-month point. Asked to sign bogus performance reviews against early joiners with "too much" equity. Refused to do it. Got fired. No severance (I was an idiot and failed to take pictures of the documents I was asked to sign; had I, I'd probably be a half a million richer). Credit card debt. CEO spent months trying to destroy my reputation. (Combining that with my accurate but politically unwise public commentary about experiences at Google, I had some interesting job interviews.) Ultimately that CEO failed (like at everything in life, except for pulling family connections to raise money for bad ideas) to ruin me and I'm fine now, but I've been through hell.
Observation: in the bootstrapped world, you risk savings. This is not be taken lightly. It's not "just money". The temptation to quit too late might land you in credit card debt or fuck up your family life or something else. Really dangerous. I like the idea of bootstrapping, but I can't advise it unless you're rich enough to be a genuine angel investor (because that's what you are). Getting to that point, savings-wise, usually requires climbing a corporate ladder anyway; at that point, the bootstrapped startup is just a victory lap.
In the VC-funded world, on the other hand, you risk reputation. (Whether savings or reputation is worse to lose depends on one's personal circumstances; there's no globally valid comparison there.) The VCs have set up a tight-knit and utterly feudal reputation economy that exists in spite of its many violations of law, at least in spirit if not in letter (the note-sharing and co-funding culture is fundamentally collusive). VCs won't go after your house or your car, but if you cross them, they'll destroy your career and reputation. Morally speaking, that's even worse.
Maybe the truth is that this startup crank being peddled is, to paraphrase George Carlin, Bad for Ya. Or maybe I'm just a dinosaur at the ripe old age of 30. I don't think so. I've seen a lot, I understand technology at a deep level, and I think the startup game is extremely dangerous and the risks are often intentionally hidden. At a Series D startup, you'll get some pathetic 0.02% slice because "the business is de-risked". It's true that a startup will never have a true "layoff" (for image reasons, it must appear to be expanding) unless in dire straits, but phony "performance" firings (no severance, and feces all over the target's reputation) to hide layoffs are extremely common. Not fucking de-risked at all.
People are waking up to the evil of the VC-funded world and its disgusting good-ole-boy network, and the way forward is going to involve bootstrapping. I just don't want people to think it's a panacea. Like gambling, bootstrapping will not fuck up your life if you can contain your impulses... but if you keep burning savings because "this month is going to be the month I hit" then you can wreck your life even harder than a VC can. Frankly, I'd rather get a bad reputation in VC-istan (there are other options) than end up $50k in credit card debt.