Hiring when it's your own money

I've now run two companies without outside investment, and I've made the same hiring mistake in both. I'd like to write it down while I'm still in the middle of making it, rather than describing it in the past tense later as a lesson I learned.

The mistake is that I under-hire, consistently, and I've been calling it discipline.

What it actually is#

When the money is yours, a salary doesn't feel like an investment. It feels like an expense, and specifically like a personal expense — the same category as rent, coming out of the same place.

That's not an economic judgment. It's an emotional one, and it produces decisions that look prudent and aren't:

Roles stay open for months that should be filled in weeks. Not because I'm being selective. Because every week the role is open is a week I don't have to write the check, and the discomfort of the open role is diffuse while the discomfort of the salary is sharp and monthly.

I hire cheap when I should hire right. The differential between an adequate person and a very good one is real money per month and it's obvious in the offer letter. The differential in output is larger and shows up nowhere I can point at. So I've repeatedly bought the cheaper one and then paid the difference in my own hours and in things not getting done.

I do the job myself instead. This is the one that hides best, because it looks like founder commitment. It isn't. It's me choosing to spend a resource I don't count — my time — because it doesn't hit the bank account. At Exposely I did the marketplace matching by hand for two years and told myself it was staying close to the customer. It was partly that. It was mostly that a hire was expensive and my evenings were free.

Why the funded version doesn't have this#

I want to be careful not to romanticize the other side. Funded companies over-hire routinely and the damage is real — teams that outrun their product, people hired for a scale that never arrives, layoffs that were predictable a year earlier.

But they don't have my failure mode. When the money came from somewhere else and was explicitly raised to be spent, a hire is an allocation against a plan. That's a different mental operation than taking money out of your own account, and it produces better decisions in this one specific area even when it produces worse decisions elsewhere.

The bootstrapping literature is all about the discipline you gain. Nobody writes about the specific tax it puts on hiring, which is where I've lost the most.

What I'm trying#

Deciding the hire before I look at the money. Answer "does this role pay for itself in a quarter" as an analysis. Then execute it. The failure happens when the two questions get merged, because then the answer is always "not this month."

Counting my own time at a real number. Not as a philosophy — as a line item, at what I'd have to pay someone to do the thing. Most of the work I've absorbed becomes obviously uneconomic the moment it has a price on it.

Noticing when "I'll just do it" repeats. Once is efficient. The third time is a role I've decided not to fill without ever deciding it.

The thing I actually believe#

Bootstrapping doesn't make you disciplined. It makes you feel the money, and feeling the money is not the same as being right about it. It improves the decisions where the emotional signal points the same direction as the analysis, and it corrupts the ones where it doesn't.

Hiring is the main place it doesn't. I've known this for a while and I'm still doing it, which is roughly where I am with most of what I've learned.