I’ve been active on HN almost as long as you. It’s not 2006 anymore. I would still follow the same career path based on what the world, HN and Silicon Valley were like in 2006. I wouldn’t based on 2020 world, HN and Silicon Valley. Would you?

Rents are astronomical. Startup math has worsened. FANG math has improved. In fact only the G in FANG even resembled the FANG of today. FANG has done a great job figuring out the innovator’s dilemma, making disruption in all their verticals much more challenging. The low-hanging fruit problems are gone so there aren’t really any two engineers in a garage problems that someone well capitalized can’t quickly copy. You now need generalist engineers, designers, AL/ML/DS engineers, hardware people, etc. on a founding team, meaning that you need to take on sizeable VC money before building IP equity and getting product market fit.

Startup risk is way way worse these days.