Improvising Some Important Lessons About Entrepreneurship
Entrepreneur Office Hours - Issue #274
This week, I had a friend and mentor visit one of my classes. He’s a wildly successful entrepreneur — someone who’s been building incredible companies since I was in high school. Naturally, you’d expect him to come in and share war stories about raising capital, scaling businesses, and navigating the ups and downs of startup life.
But that’s not what happened.
Instead of talking about entrepreneurship, he spent the entire class leading my students through improv games.
At first, they were confused. A few laughed nervously, probably thinking, Wait, isn’t this supposed to be an entrepreneurship class? But within minutes, they were all in — on their feet, reacting in real time, embracing uncertainty, and, most importantly, having fun.
While watching them, I found myself thinking: This is entrepreneurship.
Entrepreneurs and improv performers play by the same rules. They both step into uncertain situations without a script. They both have to react quickly, adapt to unexpected challenges, and make the most of whatever is thrown their way. And, most critically, they both have to keep moving forward — even when they don’t know exactly where things are headed.
That’s why one of the golden rules of improv is “Yes, and…” Instead of shutting down ideas or resisting what’s happening in the moment, you accept what’s in front of you and build on it. That same principle applies to startups. Markets shift. Customers behave unpredictably. The best entrepreneurs don’t fight that uncertainty — they lean into it, using every unexpected twist as an opportunity to build something better.
Another lesson? Let go of perfection. In improv, if you pause too long trying to craft the perfect response, you kill the momentum of the scene. In entrepreneurship, if you hesitate because you’re waiting for the perfect plan, you’ll never launch. Success comes from making bold choices, trusting yourself, and being willing to adjust as you go.
And maybe most importantly, don’t be afraid to look ridiculous. The best improv performers aren’t the ones who play it safe. They’re the ones who take big swings, commit fully, and embrace the absurdity of the moment. Entrepreneurship is the same way. If you’re too afraid to fail — or too worried about what people will think — you’ll never take the risks necessary to succeed.
So while my students expected to hear a lecture on business strategy, what they got instead was something even better: a real-time demonstration of what it means to think, act, and adapt like an entrepreneur.
And why am I sharing this story with all of you? Honestly, it’s because every entrepreneur might benefit from spending a little time exploring improv. It’s going to teach you to spend less time obsessing over perfect plans and more time practicing adaptability. It’s going to teach you to embrace uncertainty instead of fearing it. And it’s going to teach you to say “yes, and…,” a skill that’ll open the doors to unexpected opportunities, trusting that you’ll figure things out as you go. Because the truth is, success in startups — just like success in improv — doesn’t come from having all the answers in advance. It comes from being willing to step into the unknown and play the scene anyway.
-Aaron
This week’s new articles…
What if Running Out of Money Isn’t Really What Kills Startups?
Even though money is ultimately important for startups, but it’s definitely not the most critical thing.
It’s Time to Fix the Most Misunderstood Word in Entrepreneurship
You’re going to hear lots of entrepreneurs using the same word, but they’re using it in a way that could ruin your startup.
Office Hours Q&A
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QUESTION:
Hey Aaron,
I’ve been working on my startup for a while, and I’m realizing that getting customers is way harder than I expected. I thought if I built something great, people would just find it, but that hasn’t been the case. I don’t have a background in marketing, and honestly, I don’t even know where to start.
So my question is: How does a first-time founder without marketing experience figure out the best way to get their first real customers?
Appreciate any insights you can share.
- Albert
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Congratulations! You’ve just stumbled into one of the biggest oh crap moments every first-time founder faces: realizing that having a great product is meaningless if nobody knows it exists.
I get why you thought people would just find it. That’s how it feels when you see other successful companies — you assume their products just took off naturally. But, in reality, behind every “overnight success” is an exhausting, messy, and deliberate effort to make customers show up.
A good starting point is talking to your existing users or potential users. If you have even a handful of people using your product, ask them:
How did you first hear about us?
What made you decide to try us?
Where do you normally look for solutions like this?
Those answers will tell you where to focus your marketing efforts. If they found you on Reddit, maybe you should be answering questions there. If they follow specific industry blogs, that’s where you should try to get featured. If they heard about you through a friend, maybe word-of-mouth referral incentives are the way to go.
If you don’t have customers yet, go where your potential users already are — join their online communities, answer their questions, engage with them in a way that feels natural. The best marketing at this stage isn’t about selling; it’s about getting your product in front of the right people and making them realize they need it.
The last thing I’ll mention is don’t overcomplicate things. Marketing isn’t some mystical art. It’s just a process of testing different ways to reach people, seeing what works, and doubling down on that. Try something small — post in a forum, cold email 10 potential users, run a small experiment. If it works, do more of it. If it flops, tweak it and try again.
Great marketing isn’t about knowing the perfect strategy from Day 1. It’s about experimenting your way to what works. The sooner you start testing, the sooner you’ll figure out what sticks.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.