Can I Hire Someone to Run My Startup for Me?

Wouldn't it be amazing if someone else could run our startup for us?

That's the dream, really.

We build our startups to a point where they are making money, hire some super competent person with our same kind of ambition, and just sit back and let the checks tumble in while we sip margaritas on a beach.

But there's a reason why we call it a "dream" and not a "given." It works really well in our minds, but it tends to fail miserably in reality.

Why Won't it Work?

The problem with handing over the reins isn't the immediate handoff, it's all of the little compounding problems that stack up over time. That's the part we don't see.

Imagine for a moment you were a parent with teenage kids and you wanted to go on a vacation without them. When you first leave, everyone knows what they are supposed to be doing. The house is in order, the fridge is stocked, and you have a strong game plan for how to keep tabs on things.

But each day that you're gone, there's no major event, just tiny little ones. It's a spilled can of soda, a toilet that backs up, or a lawn that didn't get mowed. By themselves, these issues aren't important. But the longer you stay away, the more these stack up, until at some point you come home to a complete shit show.

The theory of the "total handoff" breaks because we take out the element of supervision. Not just any supervision, Founder supervision. The kind of oversight that only someone who has a vested interest like no one else.

What CAN We Hand Off?

Does that mean we can't hand anything off? Of course not. We can absolutely hand off reporting duties to someone who loves managing people. We can hand over day-to-day operations to a COO who lives for progress reports and details. In most cases we can likely hand off 90% of what we do to someone else in some capacity.

What matters when we hand something off is that we have a check valve in case it doesn't go right. For example, let's say we hired a new CEO to replace us. For argument's sake, let's assume this person is perfectly qualified to do that job. Now, being qualified and doing the job well aren't synonymous, especially at that level.

If we stop there and say "Let me know how it goes," that's the problem because we don't have an adequate method to check in on what's not working. It's really easy for them to cover up the "spilled sodas and clogged toilets" if we don't have a way to look deeper into the organization to keep tabs.

What CAN'T We Hand Off?

What we can't hand off is what's most important and what gets us into trouble when we do. In my experience having dealt with this first hand and watching many Founders struggle with handoffs, there are 3 categories you have to be very careful with: Vision, Culture, and Urgency.

The vision isn't just our grand ideas, it's the spirit of how we deliver the product, how we constantly innovate, and how we never settle for "good enough." That's something we're born with, which is how we got this job. The person we just hired probably isn't, which is why they're working for us.

The culture is something very unique to the Founder. Whether it's a certain discipline or irreverence, startup cultures are rarely created by hired guns. They are almost always emanating and perpetuated by the Founder.

The last is urgency. That feeling we get when we wake up at 3 a.m. in a cold sweat over a problem no one else even realizes we have, that's urgency. You can't manufacture that and you can't hire for it. It's a fundamental DNA trait that Founders possess, and when you strip it out of a startup you're begging for trouble. It's essentially where the whole "Founder Mode" meme came from.

So We're Chained to this Thing Forever?

Definitely not. We can certainly hire that CEO, but we need to err on the side of extreme caution that just handing over the keys to the castle wholesale is a terrible idea. We want to hand over access to the keys, but we still hold the keys... just in case.

More so, we never want to take our eyes off the ball entirely. We're usually doing this because we need a significant break, and we deserve it. But that break doesn't have to be a clean break from our company. It just means we need to reduce our liability.

The goal is to give us some freedom while still ensuring we have a company to come back to.

In Case You Missed it

Investors Will be Obsolete Startups don’t need your millions anymore, AI just rewrote the rules. VCs, evolve fast or face extinction.

Why is a Founder so Hard to Replace? There are a ton of jobs we can hire for — a "Founder" isn't one of them.

How Do I Get More Equity Back? Giving equity away is easy. Getting it back is super hard. So while we can get some stock back into our coffers, we have to focus more on how quickly we give it away than how we get it back.