Overcapitalization

You raised too much cash.

How can that be, and/or why is that bad? Well, investors were willing to value your sleep-improving hardware and software company at $22 million, pre-money. They were all set to give you $6 million, for a post-money valuation of $28 million. The $6 million would last you 2 years, at which time you thought you would then raise $15 million, and that would be enough to get you to profitability (or at least close). The dilution on this first raise then would be such that you had sold 6/28ths of your company to outside investors.

But no. You got nervous. You listened to your Nervous Nellie parents who had no faith in the world. So instead of rolling the dice, you raised $22 million, selling half your company and raising massive amounts of capital. With employee stock option and other dilution along the way, you ended up owning 10% of your company when it sold for $180 million. After tax, your $18 million was about $10 million. It was just enough to buy a 3-bedroom ranch house in Palo Alto. You're not rich by Silicon Valley standards, but you did just fine. Had you not listened to your parents, not overcapitalized yourself early, only raised the minimum cash needed, you'd have had closer to 30, maybe 35 percent of your company when it sold for $55 million, to net $35 million, at which point you could have retired.

That's what you get for letting your parents get under your skin. Now enjoy working the next 20 years.