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The Enemy of Who Not How - Overcoming Entrepreneurial Arrogance

Updated: Feb 1

(This is the third lesson in my series "The Rise & Fall of My Flipping Company")

Who Not How is a groundbreaking book for many entrepreneurs.

When we hear the concept of finding a “who” instead of figuring out a “how”, it’s music to our ears right?

Well then why is it so damn hard to put this into practice for many of us? Enter entrepreneurial arrogance.

It rears its ugly head in the face of every entrepreneur I’ve ever known in one way or another. So what does it mean, and how do we overcome it?

What is entrepreneurial arrogance?

When we start a business we wear a lot of hats. It’s part of the fun, and it’s part of the challenge.

We’re both the manager and the employees of each department - R&D, marketing, sales, finance, operations, and IT are all in our purview. Usually this is because we don’t have the money to bring in this team, and even if we did we wouldn’t know what to do with it!

So we get scrappy. We figure it out. We create chaos, we live in chaos, and we simplify our chaos by adding our own routines, “systems” (loosely stated), and processes.

Our business looks like a raggedy old beat up car. The mirror is taped on, the passenger door doesn’t open, the trunk is bungeed shut, and you have to kick the right tire 4 times while reciting Hemingway in order to get the damn thing to start.

But it’s ours, and because we’re used to this version of chaos we convince ourselves that we’re doing it the best way possible.

We then have a hard time bringing someone else in the business because it’s far too much work to teach them how to properly recite Hemingway and kick the tire properly, when instead they’d just fix the damn car.

That’s entrepreneurial arrogance.

What do we do about it?

Stop me if you’ve heard this before…the first step is awareness.

But really, it is.

Realize how ludicrous we sound when we say that we can’t hand off pieces of our business to professionals in that area because we’re better at it. What???

I don’t know about you, but I don’t have an accounting degree and I’m not a professional bookkeeper. I’m just a detail oriented control freak. Who’s going to do a better job managing my books?

Ok I get it’s a lot easier to say than to put into practice. So where to start?

Choose one area. Where are you currently operating outside of your zone of expertise? Or where do you spend far more time than you think you should?

Usually we experience one of two outcomes (and sometimes both)...

  1. We’re only performing at 40-60% on a given task, meaning that the finished product is mediocre at best

  2. Our finished product is great, but it takes us 2-5x the time it would take a professional to do the same thing

Look for those examples and indicators in your life and your business.

Now you’ve created awareness. Then what?

Baby steps!

For most of us, going cold turkey and handing over full control is too much to ask. So don’t! Start with a baby step.

Start documenting the outputs of what you do and some of the things that only you know right now. Let’s use bookkeeping as an example.

Is a certain credit card or account only used for a specific property? Do you typically buy supplies in bulk and use them across multiple projects that will need to be tracked? Do you have a certain way you like to look at your books every month or quarter?

This creates the framework for someone else to step in take over. They’ll have their own way of doing the work, and it’ll probably be better than you imagine. But if you can provide them with a picture of what you want the final product to look like and what’s important to you, they now are set up for success and the burden comes off of you ever so slightly.

Is it easy? Hell no. I still struggle with it. But without awareness and baby steps, nothing will change.

Do what the pros do

Henry Ford was once asked a number of questions about history and culture in an effort to prove his ignorance. His response shows a deep understanding of the importance of delegation:

“Tell me why I should clutter up my mind with general knowledge, for the purpose of being able to answer questions, when I have men around me who can supply any knowledge I require.”

He knew that he needed to stay in his zone of genius and do what was most important for him to move the Ford Motor Company forward.

And I guarantee that meant he didn’t bother with his own bookkeeping.

The best leaders surround themselves with the best talent. Why aren’t you and I doing the same??

So let’s take action! Post a comment or tag @investdgp on Instagram with some activities you’ve identified that you need to delegate out!

Let’s get out of our own way so we can spend our time focused on our most important work!

If you want help implementing anything here, reach out to me! Contact me on the website, book a discovery call, or send an email to


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