Take the barbell strategy — make sure to exit any less liquid investments (e.g. stock), and then extract capital from the bubble by raising money. When the market crashes, use your cash to purchase cheap assets and/or failing companies, and then work towards profitability.
Absolutely do not: become a VC, work for a startup, or place your capital into some kind of ‘growth’ fund indexed to tech. Don’t buy real estate in urban areas and don’t borrow.
Raising money in the bubble doesn’t do anything if you can’t liquidate from the company with good terms and you’re paid a startup founders salary right?
WeWork begs to differ - get the highly funded startup to purchase your own property/contracts to extract the value out of the startup and into your own pockets. Then when the economy/startup tanks, leave and let somebody else pick up the pieces.
In a bubble, your terms and leverage as a founder are better, including self-comp, voting shares, and funding runway. Raising money is always risky (hence the barbell), but you have unlimited optionality compared to a desk jockey.
Absolutely do not: become a VC, work for a startup, or place your capital into some kind of ‘growth’ fund indexed to tech. Don’t buy real estate in urban areas and don’t borrow.