The Not-So-Thin Line Between Leadership and Entrepreneurship
Entrepreneur Office Hours - Issue #327
Inside the Office
If you spend as much time teaching entrepreneurship as I have, you eventually run into a strange scenario where someone asks you to speak about leadership… because you’re an entrepreneur.
That happened to me again this past week. A student came by my office to invite me to speak at her organization’s leadership conference. When I asked why she thought I’d be a good fit, she responded: “Well, you’re an entrepreneur and you teach entrepreneurship, so you must know a lot about leadership.”
On the surface, I suppose it’s a reasonable assumption. For starters, both words end in “-ship.”
However, despite some superficial overlaps, “entrepreneurship” and “leadership” are not synonyms.
Entrepreneurship is about starting things — spotting opportunities, taking risks, building something from nothing. It rewards speed, independence, and a willingness to act before you have all the information. Leadership, in contrast, is about aligning people, supporting them, managing them, and, often, stepping back so they can do their best work.
Those are very different skill sets.
In fact, the more time I spend around entrepreneurs — and the more entrepreneurial work I do myself — the more I find myself believing that leadership is one of the hardest transitions founders face. Entrepreneurs love doing and building and solving and creating. In contrast, we don’t naturally gravitate toward organizing teams, managing performance, or navigating the messy interpersonal dynamics that come with growth.
But that’s exactly the kind of work you have to do when you’re scaling a company. At that point, the thing that made you successful early on — your ability to do everything yourself — becomes the bottleneck as the job shifts from doing the work to building the system that gets the work done.
That shift is where leadership begins. And, to be clear, it’s a transition lots of entrepreneurs struggle with. It’s also why so many founders either step aside or get replaced as their companies grow. Sure, they might have been great builders, but the role changed into something fundamentally different when they had to become leaders.
None of this is to say entrepreneurs can’t be great leaders. Many are. But it’s definitely not automatic. It’s a completely separate skill that has to be learned, practiced, and, in many cases, actively chosen.
That distinction matters more than we tend to acknowledge because, when we blur the line between entrepreneurship and leadership, we create unrealistic expectations for founders. We assume that because someone can start something, they should also be able to scale it, manage it, and lead a growing team. And when that doesn’t happen — when a founder struggles with hiring, delegation, or team dynamics — we frame it as a personal failure instead of recognizing it as a predictable obstacle when transitioning into a fundamentally different role.
It also matters for entrepreneurs themselves. If you believe entrepreneurship and leadership are the same thing, you’re less likely to recognize when your job has changed. You’ll keep trying to solve problems the way you always have — by doing more yourself — even when the real work requires you to step back, empower others, and build systems that don’t depend on you.
I realize understanding this gap doesn’t make the transition easy. But I wanted to share this little story just to make the issue more visible. Too many entrepreneurs assume a core part of their job is to scale their companies to billions of dollars and thousands of employees. While that goal isn’t inherently wrong, it also doesn’t have to be your goal, particularly if you enjoy building more than you enjoy managing.
Remember, there’s no shame in being a builder, and being a builder doesn’t mean you have to be a leader. Both are important roles, and some people can succeed being both, but confusing the two is where things tend to break.
-Aaron
Worth Your Time
This week I’m recommending the same book I suggested to a student who asked me to share my favorite book about entrepreneurship. To be fair, I’m not sure this is my *favorite*, but it’s definitely somewhere near the top.
The book is Kathryn Schulz’s Being Wrong. And the fundamental idea behind it is that we spend most of our lives believing we know things, when in reality, much of what we “know” is actually belief.
For entrepreneurs, this is a superpower if you can learn to leverage it. Specifically, building anything new requires constantly separating what you know from what you merely believe, particularly as it relates to your customer, your market, your product, and your strategy. And the founders who succeed are the ones who are most willing to question their own assumptions and update their beliefs when reality disagrees.
Also, as a bonus, Schulz is amazing to read. She writes in these long, flowing sentences that somehow feel like entire paragraphs — layered, thoughtful, and surprisingly conversational. It’s the kind of prose that makes you see just how poorly ChatGPT writes with all its short, choppy sentences and recycled structures. You won’t find any of that in Schulz, which, alone, is worth the extra time to dig through her words.
Tools We’re Tinkering With
Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.
One of the biggest upgrades to my weekly routine has been using AI tools to help me make slides. I have a lot to say (apparently…), but I’m no graphic designer, so being able to turn my ideas into compelling visuals has saved me (1) a ton of time, literally a day a week and (2) so much angst trying to get things pixel perfect.
My current go-to tool for content-heavy presentations is Gamma, a software one of my colleagues highlighted in a previous issue. BUT Gamma can sometimes feel a bit too… Gamma-y? And the images tend to have that AI-generated je ne sais quoi…
So when I want my slides to sing, I have been turning to Beautiful.ai. It’s giving keynote, TedX, main stage energy. All of my slides for my Narrative Design course were created with Beautiful.ai, as were the slides I used for a recent TedTalk-esque event at Duke, where everything needed to look *chef’s kiss*. If Gamma is the blue jeans of slide creation, then Beautiful.ai is the tailored suit. Don’t make me choose just one!
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