Whether you are an investor, a founder seeking advice, a business owner, or someone working through a city to encourage economic growth, we can be certain that you engage with people who are entrepreneurial. Certain of that, having read the body of works about entrepreneurship, the studies about entrepreneurs, and even the psychological works related to entrepreneurial people, we can also be certain that you are likely struggling with such people.
Particularly if you’re an employer, the entrepreneurs in your employ might seem difficult to work with, distracted, or difficult to manage. Entrepreneurial people are unusual.
“Wait a minute though Paul, what do you mean entrepreneurs working for an employer, aren’t entrepreneurs people who start their own businesses?”
In fact, no. So, before we explore how you might better engage entrepreneurs, let’s define our terms so we’re clear about who we’re talking about and how we can get more out of them, by slightly changing the way we work.
Entrepreneurship doesn’t mean starting a business. That’s easily defined as “starting a business,” and such people are business owners or founders. Entrepreneurship is the set of activities undertaken by an entrepreneur. Now, bear with me, I spent years in debate; we can’t define something by using the same word, which is sort of exactly what I just did… I have a point though – entrepreneurship isn’t starting businesses, it’s how entrepreneurial people behave. Which means what?
“Entrepreneur” is a personality trait, characterized as someone who takes personal risks, professionally, to improve things at their own expense. The word should be used in the same sense that you might call someone introverted, adventurous, or flirtatious; it isn’t something someone decides to be, rather, it defines who they are. A recent study of 22,000 startups uncovered that about 8% of the population is what you might consider entrepreneurial: these people have a need for variety and novelty, reduced modesty, an openness to adventure, and heightened energy levels.
Often entrepreneurs start businesses, because that’s a logical outcome of their behavior, but it is inaccurate to describe entrepreneur as a mere business owner nor is it accurate to say business owners are entrepreneurs. Some are. Most aren’t. This is an exemplary causation vs. correlation scenario – the word entrepreneur has been associated with business owner because of the high correlation. Entrepreneurial people are found in every walk of life, including not working – because entrepreneur doesn’t have anything to do with work, explicitly, it’s HOW some people work.
Let’s use an example that I expect everyone can relate with, drawing from your own experiences: school. I expect you can think of a teacher you had or know, who is a great teacher, they do the job, they love their kids, and they love teaching. I expect you can also imagine a teacher who does things differently than most… they try different things, they’re changing it up, they often don’t go along with the curriculum, or they don’t care about the school policies. BOTH are great teachers, being an entrepreneur in no way makes someone better or worse; the second though, is who we’d define as an entrepreneurial teacher.
Article Highlights
Entrepreneurs Do, Often Without Permission, Resources, or Approval
That might be the distinguishing characteristic of an “entrepreneur” and though I led that heading with the word “do,” the distinguishing characteristic is that it’s a personality trait, not an action – they are driven to, seemingly fixated with doing things differently, and so they stand out because they will do things even without permission, without resources, and even often when they’re told they can’t.
Want to motivate an entrepreneur? Tell them they can’t, that they’re not allowed, even though it’s certainly possible that they can.
Literally, if there was one single simple word that would describe an entrepreneur from a founder, business owner, working professional, dentist, PTA board member, city politician, stay at home dad, serial Quora answerer, or TikTok influencer, it’s “DO” because they can’t not.
Now, obviously I don’t mean that people who aren’t entrepreneurs don’t do something and that only entrepreneur do. The entrepreneurial person behaves differently; their mindset is different, and indeed, even Personality Profiles from psychologists associate certain personalities with entrepreneurship – it isn’t a job, role, career, or decision, it’s who they are.
See the sidebar for some insight into Personality Profiles that are considered Entrepreneurs.
Jean Baptiste-Say noted that, distinct from other people working or starting/running businesses (as identified by Adam Smith in Wealth of Nations), the “entrepreneur” is that adventurous personality found in SOME. The entrepreneur is the type of person who can’t help but see gaps/problems/opportunities and NEED to do something about them.
Entrepreneurs are less concerned with determining “the right way,” they don’t ask for permission as much, they aren’t concerned whether they have the right permits, certifications, or approvals.
They just DO it. And figure out the formalities later.
Because of this there is a genuine challenge and concern that should be more recognized about entrepreneurs… these are the people who make what appear to be mistakes and who struggle most with mental health issues. Why? Because they’re willing to just put themselves at risk, put their money to work, to TRY and improve something.
Side note: “appear to be mistakes” because you perceive their action and failed outcome as a mistake – entrepreneurs don’t see it that way! It was a lesson, and the attempt made to try and make it better.
Most of the time they’ll be wrong. They’ll fail. They’ll lose money. This will frustrate people. This tendency is naturally met by most people who will tell them, “No,” “bad idea,” or “won’t work.” and when those efforts fail as they mostly will, those people will have a smug “told you so” kind of reaction that makes it even harder for entrepreneurs.
So, how might we better connect with, inspire, and engage such people? YOU DO.
Personality Profiles and Entrepreneurs
Myers-Briggs
ENTP (“The Debater”)
ENTJ (“the Commander”)
ESTP (“The Entrepreneur”)
INTJ (“The Architect”)
Enneagram
Type 3 (“The Achiever”)
Type 7 (“The Enthusiast”)
Type 8 (“The Challenger”)
DISC
High D (Dominance)
HIGH I (Influence)
Did you catch that? Myers-Briggs literally refers to a specific personality profile as The Entrepreneur: ESTP
Big Five
Openness to Experience
Conscientiousness
Extraversion
Low Neuroticism
StrengthsFinder
Strategic
Activator
Self-Assurance
Ideation
Woo (Winning Others Over)
- Accomplish something and involve them
- Set the meeting, agenda, and details, and simply tell them
- Ask specifically for who you want to meet or what you need done, don’t ask if they “can help”
Better engagement from entrepreneurial people comes from providing them with the action to take rather than asking if they can or by being flexible. Of course, they can… but while you’re working out the details, they have a need to be getting shit done.
Little is more frustrating to an entrepreneurial person than meeting someone else who says they’re an entrepreneur, or that they want to be an entrepreneur, only to learn that what that person really wants is a job, money, or direction. In the same breath, that person has said they are an entrepreneur and yet they aren’t reflecting any of the traits that would define them as such. As an entrepreneur, you’d be getting those things. You’re going to turn off the entrepreneur from helping because entrepreneurial people don’t waste time on misinformation and hurdles, we’re too busy getting things done.
If you’re seeking advice, help, resources, or a job, lead with that and characterize yourself accordingly. An entrepreneur will act to help, but only when it is clear how and that their help will actually be impactful to everyone involved.
Likewise, when a genuine entrepreneur shares what they are DOING and the audience is NOT entrepreneurial, they get turned off and frustrated by MORE WORK being created for them from people who aren’t just getting it done. The secret is in accomplishment not discussion.
Some approaches that you should avoid with entrepreneurs:
- “Can we meet?”
- “Can I pick your brain”
- “Would you be able to participate in…”
- “What works best for you?”
Notice how these seemingly supportive or open-ended opportunities that sound positive to you, are actually turn offs to entrepreneurial people. You’re not providing the action to take, having taken action yourself – in the mind of an entrepreneur, you’re already wasting our time.
Again, we can look at it from another perspective. If you reply to entrepreneurs in the following ways, you’re going to lose them. This time, I’ll explain:
- “How can I help?” – You’ve just had a good meeting, it was productive, and then you ask the entrepreneur, “how can I help?” Seems positive, doesn’t it? But the mind of an entrepreneur is now thinking, “What do you mean how can you help? What are you doing or going to do?”
- Better: Tell me what you’re going to do and do it so we can go back to what we’re doing.
- “Well, I’d love to stay connected and keep me in the loop about how it’s going.” – okay…. We’ll add you to the email list to which I might send out a newsletter someday. Again, what you might perceive as being encouraging, removes you from an entrepreneur’s peer group.
- Better: Set an expectation of accomplishment, explain why you want that done, and ask to be told when it is finished. Done!
- “If I can ever do anything to help, let me know!” – We’ll try to remember you among the thousands of other people offering to help with anything.
- Better: You know yourself; we need to get things done, and you’re telling us to come up with something ideal that you should do for us. You can help, just do something.
- “Are you interested in being involved?” – This also comes across in the form of a sales pitch, funding pitch, or idea pitch that you might have just discussed. Don’t end with that question! – We’re doing a million things and you’re not asking explicitly we can help do what you need while offering why and what’s in it for the entrepreneur. Entrepreneurs are interested in being involved in everything; that’s kind of what it means… now you’re making us figure out what that involvement in your thing would be?
- Better: Here’s what I need from you… here is why I need that from you… and here is what it would look like for you. Great! I’m in.
- “Well, let me tell you what I do and how I can help.” – This is a tricky example because it probably sounds to some of you like you saying that, to an entrepreneur, is what I’m actually advising you say. Here’s the thing… As an entrepreneur, I’m not hiring, I’m not seeking help, and I don’t want your proposal. So don’t tell us how you could help, do it.
- Better: be direct – I will close that deal for but I’m a sales professional, so I’d want 40% commission.
It is critical that you distinguish roles (CEO, Sales, Developer, Investor, Advisor) from personality (extroverted, music-lover, entrepreneur) because efficiency in your communication draws from both targeting the role AND the personality. As a CEO I operate one way. As an investor I operate with people a different way. As a mentor and provider, I engage still another way. But as an entrepreneur? We have s*** to do and want to get it done so if you’re not helping that, you’re slowing us down.
Interesting, thanks for the response. Never thought about it this way, but some of it makes sense.
Absolutely. It’s always easier to ask for forgiveness than to ask for permission.
Made me stop, read, and think. Thanks for sharing.
The world since the beginning of time has been 98% bullshitters and 2% doers.
There are doers who “do” within existing structure and there are doers who create the structure within which they do.
Startup world likes to think it invented business and/or sex. They did not.
Back when I got an MBA in the 1970s the focus was on finance and I never heard the word “entrepreneur.”
I was already one before I was first confronted by that word in the context of the startup culture.
When the buzzword “entrepreneur” first came about, corporate America made up its own word — “intrapreneur” — to compete with the allure of the “e” word. It was intended to afix the same hot take to being a corporate innovator. Sort of a head fake. There’s no real risk in corporate America.
In fact, much of what you describe — the cool teacher — is simply innovation rather than entrepreneurship.
It really doesn’t matter because it’s only words.
The world is still 98% bullshitters and 2% doers.
The successful entrepreneurs are the guys who live in the big houses.
Merry Christmas to all!
Interesting. It’s hardly a buzzword, “entrepreneur” was first used in 1755 by Irish-French economist Richard Cantillon in his book Essay on the Nature of Trade in General. The word originally comes from the combination of two Latin words entre, to swim out, and prendes, to grasp, understand, or capture. In the year 1800, French-Irish Economist Jean-Baptiste Say popularized it further to reinforce that it has nothing to do with business, inventing business, or corporate. Long time between 1800 and corporate America affixing itself to it.
I’ve never met someone in startups who thinks they invented business. Do you have some references to articles that claim as much?
Not sure how I might follow that much of what I’m describing is innovation, I’m talking about people and communication. Innovation is the practical implementation of an invention through goods or services. Perhaps you could elaborate on how an entrepreneur and their behavior is simply innovation.
Very informative
Paul O’Brien
Reading comp problem — I was clearly addressing the teacher example you offered. That teacher was not an entrepreneur; she/he was an innovator at best.
There is no “risk” in teaching. Risk is the lingua franca of entrepreneurship.
There were startups since the beginning of business, but the startup world as we know it today began with the creation of venture capital pools of money that trolled for investment. The term “Silicon Valley” entered the lexicon in the 1970s.
When I moved to Austin in 1980 there was not a single VC fund in town until Jack Crosby, et al, formed Rust Ventures. RV became Austin Ventures. The rest is history.
The etymology of a word is not the same as its widespread usage that morphs over time. The word “enterpreneur” was not widely used until the advent of VC.
I did not say that an “entrepreneur and their behavior is simply innovation.” I said that in the instance of the teacher, that was innovation.
Not every innovation is entrepreneurial; nor is every entrepreneurial endeavor innovative. They are different concepts.
I think you have commingled the concepts and that is a flaw.
You seem wildly thin skinned whenever anyone comments on your postings. You OK?
Merry Christmas
Jeffrey L Minch I’m okay, I just find it interesting that your approach to public discussion of things includes insulting people.
Adam Grant highlights the importance of fostering creativity and innovation in any role.
Encourage entrepreneurial thinkers by providing autonomy and recognizing their unique ability to solve problems.
Create environments where they can thrive, setting clear goals and celebrating achievements.
This approach not only harnesses their potential but also drives meaningful progress.
A nice collection of all Entrepreneurship mannerisms, philosophies, and behaviors! Great job! Thanks and Happy Holidays!
This is an engaging, articulate read. Thank you for sharing Paul O’Brien
This is a great article Paul!
Great read by Paul O’Brien
My favorite excerpt:
“Entrepreneurship has been misunderstood. It’s not about starting businesses—it’s about a mindset, a personality trait that compels someone to act, innovate, and take risks to improve things, often without permission or resources. Entrepreneurs exist in every walk of life: as teachers, employees, dentists, or stay-at-home parents. They do, often because they can’t help themselves.
But here’s the rub: entrepreneurial people can be frustrating. They don’t wait for approval, they’re fixated on outcomes, and they’re wired to take risks—traits that can lead to tension, failure, and even mental health struggles. Yet, they’re the ones who drive real change.”
Entrepreneurs aren’t just defined by their actions; they’re driven by a mindset that thrives on risk, creativity, and an obsession with improvement. Yet, labeling them solely as ‘doers’ oversimplifies their role. I’d argue it’s not just about what entrepreneurs do but why they do it.
Carlo Rivis agreed.
I’m trying to fight the incessant use of the word entrepreneur to define business owners. That lack of distinction causes so much strife: mismatch, bad advice, and failure.
Entrepreneur != Business owner != Startup founder
Thank you for agreeing, Paul O’Brien! Distinguishing between a business owner and an entrepreneur is crucial, as it shapes expectations, advice, and the mindset required to succeed. Entrepreneurs innovate and disrupt, while business owners manage and grow what already exists.
This is inspiring!! Entrepreneurship is a compulsion!
Briana Johnson-Sims yes! It’s a natural tendency, not a learned skillset. I love that notion, it’s a compulsion.
This resonates hard with me:
“How can I help?” – You’ve just had a good meeting, it was productive, and then you ask the entrepreneur, “how can I help?”
Like, I just spent 30 minutes sharing goals and objectives, and THAT’S your question?
It signals unseriousness.
I just spent 5 minutes with a founder in Dallas, sharing inside stories about how the accelerators didn’t do squat for him, and we wrapped by making meaningful introductions to others for one another.
This isn’t hard. Help or get out of the ecosystem