Would You Invest All Your Money at This Price?

If I handed you the cash equivalent of your vested equity today — two million dollars, or whatever crazy number the last valuation of your company would imply — would you turn around and put all of it back into the current Series D?

Maybe you’d rather spread it out among the three other well-funded competitors who are all doing the same thing—infrastructure for agentic e-commerce or fully automated AI-driven GTM?

If you’re a founder, the amount of money is probably 10x that or more.

Very few people would say yes and nobody would deliberately build the portfolio you're already sitting on.

Maybe the company IPOs big and you feel lucky.

What if it doesn’t? Would you regret not diversifying?

If your equity is options, you don't own anything yet — you own the right to buy something. Converting paper into anything sellable means writing a check. Sometimes a big one. For an early employee, often an engineer, at a company that's marked up a few times, the exercise cost alone can rival a down payment on a house.

Then, there’s taxes.

Exercising ISOs on a company that's appreciated triggers AMT on the spread between your strike and the current 409A — a tax bill on paper you can't yet turn into cash. If the company IPOs, fine, you cover it. If the company drifts and your shares end up worth less than what you paid the IRS for the privilege of owning them, congratulations, you got hammered on a bet that didn't work.

This happens to people. Regularly—and it’s becoming more of an issue as AI defines what the market is looking for in both an employee and a founder.

Take engineering. The engineering role gets redefined every decade. Mathematicians in the fifties. Craftspeople in the seventies, writing elegant systems by hand. Hackers in the eighties who could ship. Architects in the nineties managing complexity. Web generalists in the 2000s moving fast. Specialists in the 2010s, deep in cloud, mobile, SRE.

In the last eighteen months it happened again, faster this time.

The scarce thing right now isn't code. AI does that. It's judgment — what to build, what to kill, what "done" actually means, the ability to see the whole system at once.

Being an IC these days is feeling a lot like being a founder of your own mini-company.

So why not run your own company instead of doubling down on expensive equity someone else controls?

The engineers who got dramatically more valuable in the last two years are the ones who compose systems, not the ones who type fast. The engineer you want at employee #7 today is the same person who could ship a business with a laptop and a Cursor subscription—only before, starting a company came with a lot more risk and overhead.

Plus, managing employees. Ew.

I hear both sides of this constantly. Solo economics have never been better — one strong engineer with good taste can build a cash-flowing company that used to require a team, a round, and eighteen months of management.

Yet, employee #60 at Cursor just bought a boat.

The upside got bigger everywhere at once—and there’s never been more fear that it might all come crashing down.

If the current wave is turning you into someone who could go start their own thing, then the opportunity cost of your position in someone else's company is bigger than it was two years ago. You're taking concentration risk right when you're turning into the person who could walk.

Plus, there's a whole ecosystem of secondary funds, family offices, and syndicates that want to buy private-company shares off early employees and investors. Some are excellent and price fairly. Some are vultures. Most need the company to sign off, which drops the whole thing back on the founder's desk.

If you're that founder: are you going to let people take money off the table? Real tension here. Enabling secondaries keeps good employees from leaving purely for liquidity and admits that a ten-year run to IPO is a big ask. It also sets a price on your own paper, moves your next round negotiation, changes your ISO strike, and messes with the head of every employee who doesn't sell. Not free. Not automatic. Not something to figure out for the first time when a key engineer walks in with a resignation letter and a lawyer.

None of this is Google-able. Situations differ. The tax code punishes bad timing. The wrong move turns money you thought you'd found into money you actually lost.

Sometimes you should sell. Sometimes you shouldn't. If you haven't sat down and figured out what your equity is actually worth, what routes exist to get at any of it, and whether you'd deliberately construct this position from scratch today, you're letting the situation decide for you.

That’s why I'm doing a webinar on secondaries and employee equity with Qapita. Both audiences welcome — engineers who own the paper, and founders deciding what to do about the people who own it.