What's Really an Entrepreneur's Most Important Job?

Entrepreneur Office Hours - Issue #275

Photo by Magnet.me on Unsplash

A strange thing happens every time I post a video that goes viral from one of my classes. No matter how positive the overall reception, I’m always greeted with a small but vocal wave of outrage in the comments. People accuse me of exploiting students, wasting tuition money, or using the classroom as my personal content farm. And no matter how many times I explain it, they just… don’t get it.

What they see is a professor filming in a classroom, and their minds fill in the rest. They imagine the class is some required intro-level course students have to take to graduate. They imagine the students are being forced to participate. They imagine I’m prioritizing TikTok views over lectures on the quadratic formula.

What they can’t imagine is the class is an elective. It’s about social media. My students chose it. And on the first day, we talk about how we’d be creating content together so they could understand what it means to build a social media brand. In fact, many of the videos I post are ideas that they pitch and ask to participate in. They’re not being taken advantage of. They’re learning — by doing exactly what the class was designed to teach.

Still, people don’t — or can’t — wrap their heads around that. They don’t know the full context, so they insert their own, and that’s the lesson I want to highlight — not just for professors on the internet, but for entrepreneurs everywhere.

This same phenomenon happens all the time outside of social media. When you pitch your startup to customers or VCs, they’re not just evaluating your words. They’re interpreting your pitch through the lens of their own experiences, biases, expectations, and assumptions. They don’t know what you know. They don’t have your context. And unless you give it to them, they’ll supply their own, which is why your most important job, as an entrepreneur, is to supply context.

You need to understand this because it’ll help you learn to stop assuming people will “get it.” Instead, you start assuming they won’t. You learn to anticipate the narratives they might bring with them, and you get ahead of those narratives. You clarify. You contextualize. You explicitly say, “This is what you might be thinking — but here’s what’s actually happening.” That’s not over-explaining. That’s good communication.

It’s frustrating when people misunderstand you, especially when your intentions are good. But as an entrepreneur — and really, as anyone building anything in public — your job isn’t just to build the thing. Your job is to help people see the thing clearly, on your terms. If you don’t, they’ll create their own version, and it probably won’t be the one you intended.

-Aaron

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This week’s new articles…

Is it Really Possible for Entrepreneurs to Work too Hard?

Entrepreneurs are some of the hardest working people on the planet, but what if that’s killing your startup?

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The Naive Pricing Mistake Every New Founder Makes

Pricing is one of the hardest things for inexperienced entrepreneurs to get right because the best strategy isn’t obvious.

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Office Hours Q&A

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QUESTION:

Hi Aaron,

I love all you social media videos. It always lights up my day when you appear in my feed. So thank you for that.

I feel like I have a question you could be great to answer. I’ve been hearing a lot about how important storytelling is for fundraising, pitching, marketing—basically everything. You always talk about it too. But not all of us are natural storytellers. I have no idea what part of my story people even want to hear.

How do I figure out which parts of my personal story are worth telling. And also, how do I make sure it actually connects with the people I’m trying to reach?

Thanks,
Krissa

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First off — thank you! I love hearing that my videos are showing up in your feed and bringing a little light with them. That’s… umm… kind of the goal. =)

Now onto your question, which I love even more. You’re absolutely right: storytelling is everywhere in entrepreneurship. Fundraising? You’re telling a story. Pitch decks? Story. Website copy, onboarding flow, job postings, investor updates? Story, story, story, story.

The good news is storytelling isn’t about being a “natural.” It’s also not some magical gift you either have or don’t. It’s a skill, and just like any other skill, you can get better at it — especially once you realize the most powerful stories aren’t about being the loudest or most dramatic or most polished. They’re about being honest, specific, and useful.

So, how do you know which part of your story people actually want to hear?

Start by flipping the question: What does your audience need to understand in order to trust you?

If you’re talking to investors, they need to know why you are the right person to solve this particular problem. If you’re pitching a product to customers, they need to know you get what they’re struggling with. If you’re hiring, your team needs to know why this mission matters to you — and why it should matter to them.

Simply put, it’s answering the question: What problem do you care about, and what happened in your life that made you care about it enough to build a business around it?

That’s it. That’s the story people want. And it doesn’t have to be epic. You don’t need to have overcome tragedy or have climbed Mount Everest. It just needs to be true and relatable and help your audience understand why this thing you’re doing isn’t just a business — it’s personal.

As for the second part of your question — how do you make sure it connects?

There’s a simple trick: make your story about them. Tell your story in a way that helps your audience see themselves in it. Highlight the parts that reflect a struggle they know. Show them the turning point where things started to make sense. Keep it simple, don’t try to impress. Just focus on making them feel understood.

If they nod along while you’re talking, if they feel like you get them, they’ll trust you. And if they trust you, they’ll listen. That’s how storytelling works. Not by dazzling people, but by making them feel seen.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.