I started a company, failed miserably, but it was easy to get a well-paying job with a salary and a lot of stock when I did. And the company I'm at now I joined long after product-market fit. I was still ahead in my career of people who were in the same place but didn't start a company. And I paid myself slightly less but still well enough to get by, so the only painful part was the transition between jobs. If you're a talented engineer you'll be just fine. I've probably had a job offer per week since then, too.
Now I've Saved up enough money, and I'll make another go. If I fail? Back to the same pretty-damn-good default position.
Your anecdotes are not an indication that the risk is overstated. Who knows what factors decreased the risk for you, and while you attribute it to 'engineering talent', it's far more likely to be something like more skill at using the network of connections you've established (most jobs are still filled this way).
Whatever that factor is, it isn't necessarily a common skill.
I ran a remote company once before. I'll never do it again.
Similarly, if you're doing startups, failure doesn't go on your permanent record and you can try again. These career fields are about choosing your priorities in life, that's how you choose one path or the other.
It's up to me to learn and find a better way.
Assuming he only does it because he's an investor is assuming the worst. He can probably only invest in a half dozen companies per year, so encouraging everyone he meets to start companies would be a very indirect Nd unnecessary way of filling the top of that funnel.
Assuming you live in SV or NYC
It is also good to think about alternatives to the typical startup vs corporate dilemma. For example, securing a job and working on side projects until there is a signal they can be something more.