How to Manage an Entrepreneur The Right Way

Man holding sign saying "entrepreneur for hire" with graphic title of "How to manage an entrepreneur"

This is an orientation letter for any of my future bosses. I know it’s tough to manage an entrepreneur, but I promise, if done right, you’ll get more out of us than anyone else you work with.

Please don’t hear me wrong…I’m not being a hotshot or putting on airs when I call myself an entrepreneur. To me, being an entrepreneur is not a skill…it’s a condition. Let me explain…

Being an entrepreneur doesn’t imply that you’re good at anything. It’s more of a personality trait than it is a talent. I realize that in today’s world, we might think of an entrepreneur as someone who possesses the skills necessary to launch a new venture, but you can look up the definition in as many online dictionaries as you want and you’ll find that the criteria for being in the club is not measured in success…it’s measured in risk and taking ownership.

“A person who organizes and manages any enterprise, especially a business, usually with considerable initiative and risk.”

So, in my case, how this plays out is that my work-life takes on two distinct characteristics:

#1 – I Want to Work on My Own Ideas

Scratch that…I need to. No, scratch that…I’m going to, one way or another.

It’s not a vanity thing. It’s not like I just “march to the beat of my own drum”. I just can’t get invested fully if I’m working on someone else’s idea. I can’t take ownership of it, and that means the end result would be a half-hearted attempt at best.

Now, you might think this makes it impossible for me to work for someone, but actually I’ve proven to be a tremendous asset to anyone I work for, provided they learn how to manage an entrepreneur.

For the record, after freelancing for the first 8 year of my career, I’ve spent the last 7 working for two different companies as an employee. Both companies have gotten the best out of me. Any good manager I’ve worked for eventually figured out the simple truth that I don’t like being simply told what to do or how to do something…rather, I need to be told what the desired outcome is or what the goals are. If you let me tackle the problem in my own way, while trying to achieve an agreed upon result, you’ll find that I do exceptional work.

Does that mean I’m not collaborative? Not at all. I’m quite flexible with my ideas. For example, typically when my boss brings a particular challenge to the table, I go work on it and bring him back more than one solution. He then asks questions and makes suggestions to improve it and we often end up with an improved solution that we both like. It’s not a compromise for me. It’s still my idea in the sense that I believe in it, but sometimes I get it wrong on the first pass and you can easily convince me that my idea is wrong (or at least flawed) with data. I’m more and more data-driven each passing year, as experience has taught me that gut instincts, while they have their place, can drive you to build things that don’t work because you didn’t do the proper diligence.

So, I like to work on my own ideas but you can turn that particular character flaw into an asset if you manage it right. However, there’s another characteristic that goes along with it:

#2 – I Love Starting Things

Here’s the deal…I love working on new things because it’s about the unknown. It’s about the risk involved. No, not financial risk necessarily. I’m actually personally very conservative financially. The risk I’m talking about is how the market will receive it.

When I’m starting something, whether it’s a new business or a new product offering for the company I work for, I have no idea how the market is going to respond to what I’m creating. There’s a lot at stake when you’re solving problems in business and make no mistake, the validation of your solution comes from the market. This is where you need a true entrepreneur…one who actually wants to boldly put their ideas out there to be judged by the market. Not everyone wants that kind of pressure…but true entrepreneurs do. The healthy fear of it will drive them to do their best work.

But there’s a catch…as soon as the market has responded and validated the idea, I want to do something else! I love starting things, because that’s where the risk is. Take away the risk and I’m not having fun anymore. I can build the train and get it going down the track, but I can’t keep it running after that. Frustrating, isn’t it boss?

Entrepreneurs Don’t Compromise

I’m sure by now you must be thinking that hiring an entrepreneur is more trouble than it’s worth, but nothing could be further from the truth.

The truth is, you want entrepreneurs on your team. If you’re trying to, as Steve Jobs would say, “put a dent in the universe”, then entrepreneurs are the people who are going to do it. When challenged, they work harder than everyone else and perhaps most importantly, they don’t compromise.

See, the trouble with teams in business is that sometimes in order for everyone to get along, everyone has to have an equal say. This is great for relationships, but it can be horrible for business. If there are 5 different ideas in the room, the answer it hardly ever a combination of the best parts of each one. That’s called compromise. In other words, a camel (horse built by committee). Nobody takes ownership of a compromise, so it always produces and inferior outcome.

Entrepreneurs are the ones who are going to protect the integrity of your project and stop it from becoming a camel. They will be the guardians of a singular path forward. They’re not people pleasers, they’re problem solvers. Their religion is the market and the only real truth for them is what the market says. Yes, it can be frustrating to manage an entrepreneur, but they’ll run through walls for you. Other people might help you keep the status quo, but entrepreneurs are the ones who will move your company forward.

How to Manage An Entrepreneur

My encouragement to you is to learn how to manage people like me. The biggest advice I can give you is to clearly identify what you are trying to accomplish. When I bring back my best ideas, if you feel they need more work, ask questions, point out problems, and keep preaching the goals. Try not to tell me how to do it as you’ll risk losing my interest. Use phrases like “I’m concerned this isn’t going to get us to where we want to be because of…” or “Do you believe this solution will achieve the results we’re looking for?”

If you have your own idea about how to tackle the problem, and you feel fairly strongly about it, don’t ask me to tackle it. Get someone else for that particular project. Otherwise it’ll just be frustrating for the both of us.

Other Tips

Another piece of advice: have us train our own replacement if we tend to lose interest right after a project is stood up. That will often give us just enough “newness” to keep us interested a little bit longer.

Also, don’t be intimidated by us. I’ve been told a couple of times that I’m intimidating or too opinionated in a meeting. For sure, that means I’ve needed to address my body language and tone, but please understand, it’s passion more than anything. I’m actually glad to be on the team and want to play my part. So if I’m pushing too hard, speak to me privately and let me know that while you want my input, I have to temper how I communicate it.

Finally, if one of your entrepreneurs is not expressing his opinion as much in meetings, then he’s disinterested. You need to act quickly if you don’t want to lose them. I think I’ve proven to my bosses that I have no problem following their leadership in the end. However, I view my value to the team is offering my opinion passionately right up to the moment that the leader decides which way we’re going to go. Once that decision is made, even if it’s against my idea, I fall in line immediately. If for some reason I think we’re still way off, I don’t work against them. I confront them privately and hash it out until I feel I’ve been heard so I can buy-in. A quiet entrepreneur is not healthy. Make sure your company culture is a healthy one for the entrepreneurs on your team.


I hope this gives you some insight into how to manage an entrepreneur. I’d love to hear your input or experiences! Feel free to leave a comment below so we can engage or contact me directly!