Jason Sherman

In this episode of Strap On Your Boots, I reflect on how startup culture shaped my view of entrepreneurship and why I recently found myself questioning one of my own assumptions. After learning about entrepreneurs who buy existing businesses instead of building companies from scratch, I began wondering whether we’ve become too attached to a single version of what entrepreneurship is supposed to look like. I share lessons from my own journey building startups and explore why sustainability, execution, and long-term value creation may deserve just as much attention as innovation and growth.

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Lately I’ve been thinking about something that caught me by surprise because it forced me to reconsider an assumption I’ve probably been carrying around for most of my adult life.

A few weeks ago, I came across several discussions about entrepreneurs who were choosing to buy existing businesses rather than start companies from scratch. At first, I didn’t think much of it. It seemed like an interesting trend, but not necessarily something I would spend much time thinking about. Then I noticed my reaction to it. For some reason, buying a business felt less entrepreneurial to me than building one. The moment I recognized that reaction, I became more interested in understanding where it came from than in the trend itself.

After all, if you really think about it, purchasing a successful business can be an incredibly entrepreneurial decision. You’re taking on risk, investing capital, accepting responsibility for employees, customers, operations, and future growth. None of that sounds particularly passive. Yet somewhere in the back of my mind, I had apparently developed the belief that entrepreneurship was supposed to begin with a blank page.

The more I sat with that realization, the more I started tracing it back to my own experiences and the environment that shaped my understanding of business.

I’ve spent most of my professional life creating things. Whether it was building startups, launching mobile apps, producing documentaries, hosting podcasts, developing software products, or working in AI, the common thread has always been the same. I enjoy taking an idea that doesn’t yet exist and turning it into something real. There’s a creative process involved in entrepreneurship that has always appealed to me, and I suspect that’s true for a lot of founders. The challenge isn’t just building a company. It’s imagining a future that doesn’t exist yet and then spending years trying to bring it into existence.

When I first became interested in entrepreneurship, the stories that captured my attention almost always involved founders creating something new. The internet was transforming industries, technology companies were growing rapidly, and startup culture was becoming increasingly visible. Every article seemed to focus on a founder with a big idea. Every conference featured people discussing innovation, disruption, growth, and scale. Every success story followed a familiar arc in which someone identified an opportunity, built a product, and eventually created a company that became larger than anyone initially expected.

Looking back, I can see how much those stories influenced me.

At the time, I wasn’t consciously deciding what entrepreneurship meant. I was simply absorbing the examples that surrounded me. The founders receiving attention were building startups. The entrepreneurs appearing on magazine covers were launching companies. The people being interviewed on podcasts were talking about growth, funding, product development, and expansion. Without realizing it, I started associating entrepreneurship with a very specific type of journey.

What’s interesting is that I never stopped loving that version of entrepreneurship. Even today, I find it exciting to hear about ambitious founders pursuing difficult problems. I still enjoy building things. I still enjoy the process of creation. I still find myself fascinated by new technologies and new opportunities. None of that has changed.

What has changed is the way I evaluate businesses.

When I was younger, I was often captivated by potential. I wanted to know how large a market could become, how quickly a company was growing, and whether a new idea might completely reshape an industry. Possibility itself was exciting. The future always seemed more interesting than the present.

Over time, though, experience started shifting my attention toward different questions. Instead of focusing exclusively on growth or visibility, I became increasingly interested in sustainability. I wanted to understand whether customers continued coming back, whether the company was generating consistent revenue, whether the economics actually worked, and whether the people running the business had built something capable of surviving difficult periods rather than simply thriving during favorable ones.

I don’t think that change happened all at once. It probably developed gradually through years of building companies, watching startups succeed, watching startups fail, and learning that reality is usually more complicated than the stories we tell about it.

One of the things entrepreneurship teaches you fairly quickly is that ideas are only the beginning. Most of the work happens after the excitement of the idea has faded and you’re left with the responsibility of making something function in the real world. Customers don’t care how innovative a product is if it doesn’t solve their problem. Employees don’t care how ambitious the vision is if the business can’t support itself. Investors eventually want results. Markets eventually reveal weaknesses. Assumptions eventually get tested.

That doesn’t mean innovation isn’t important. It absolutely is. But after you’ve spent enough time building things, you start developing respect for businesses that consistently create value year after year, even when they aren’t attracting headlines or generating excitement.

In fact, some of the most impressive entrepreneurs I’ve met weren’t running companies that most people would recognize. They weren’t speaking at major conferences or appearing on podcasts. They weren’t announcing funding rounds or discussing disruption. They were focused on serving customers, improving operations, maintaining profitability, and building organizations that could continue functioning long after the initial excitement had passed.

I don’t think I fully appreciated how difficult that was when I was younger.

Part of the reason is that startup culture naturally gravitates toward stories about beginnings. We celebrate founders because beginnings are exciting. We celebrate launches because launches are visible. We celebrate rapid growth because growth creates momentum and attracts attention.

What we don’t talk about nearly as often is the challenge of maintaining a successful business over long periods of time. There’s nothing particularly glamorous about delivering value consistently for twenty years. There’s no dramatic announcement attached to it. There’s no viral moment. Yet when I think about it honestly, that accomplishment may be far more difficult than many of the entrepreneurial achievements that receive significantly more attention.

And I think that’s where this business acquisition trend started becoming interesting to me.

It wasn’t because I suddenly wanted to buy a business.

It was because it revealed how much my own perspective had evolved.

The younger version of me would have looked almost exclusively at the creation story. The version of me sitting here today finds himself increasingly interested in what happens afterward.

The more I thought about it, the more I realized that this wasn’t really a conversation about buying businesses. It was a conversation about how experience changes the way we look at opportunity.

One thing I’ve noticed over the years is that entrepreneurship often gets presented as though there is a single path that ambitious people are supposed to follow. You come up with an idea, build a product, grow a company, and hopefully create something valuable along the way. There’s nothing wrong with that path. I’ve spent a good portion of my life pursuing it. But the older I get, the more I realize that entrepreneurship is much bigger than the startup ecosystem that most of us are exposed to.

I think part of the confusion comes from the fact that startup culture is incredibly visible. The stories are easy to tell. There’s a clear beginning, a clear mission, and usually a founder at the center of the narrative. It’s naturally compelling because people enjoy stories about creation. We like hearing about someone who starts with an idea and turns it into something real.

What we hear much less about are the businesses that quietly become part of the fabric of everyday life. The company that has been serving customers for thirty years doesn’t generate the same excitement as a startup that launched six months ago and just raised a few million dollars. Yet if you think about it for more than a few seconds, the older company has accomplished something remarkable. It has survived changing markets, economic downturns, new competitors, technological shifts, and all the unpredictable challenges that come with running a business for decades.

I don’t think I fully appreciated that when I was younger.

When you’re first getting started, it’s easy to focus on what could happen. Possibility is intoxicating. You look at a blank page and imagine all the different ways a business could grow. You picture the customers you’ll attract, the products you’ll launch, the opportunities you’ll create, and the impact you might have. That optimism is one of the things that makes entrepreneurship possible in the first place. If founders spent all their time focusing on the odds against them, most companies would never get started.

At the same time, there’s a difference between appreciating possibility and overlooking reality.

One lesson I’ve learned repeatedly throughout my career is that building something is often very different from imagining it. The idea stage feels exciting because everything still exists in its ideal form. Once you move into execution, you’re dealing with real customers, real constraints, real competition, and real problems. Every entrepreneur eventually discovers that the business they imagined and the business they actually build are rarely identical.

I’ve experienced that myself more times than I can count.

There have been projects that looked incredibly promising on paper but turned out to be much harder than expected. There have been ideas that seemed relatively straightforward until real customers started interacting with them. There have been opportunities that appeared insignificant at first and eventually became far more valuable than I anticipated.

If there’s one thing entrepreneurship has taught me, it’s humility.

The market has a way of correcting your assumptions.

Customers have a way of revealing flaws in your thinking.

Reality has a way of exposing weaknesses that enthusiasm alone can’t overcome.

And honestly, I think that’s one reason my perspective has evolved over time.

When I was younger, I often admired entrepreneurs for their vision. Today I still admire vision, but I also have enormous respect for execution. Building a sustainable business requires a completely different set of skills than simply identifying an opportunity. It requires patience. It requires consistency. It requires making good decisions over long periods of time. Most importantly, it requires continuing to create value long after the excitement of the original idea has worn off.

That’s why I find myself looking at businesses differently today.

When I hear about a company, I’m less interested in the story that got it started and more interested in how it functions now. I’m curious about what keeps customers coming back year after year. I want to understand why employees stay. I want to know how the company adapted when circumstances changed. Those details tell me much more about the quality of a business than a press release ever could.

Maybe that’s just a function of age.

Or maybe it’s what happens when you’ve spent enough time around entrepreneurship to recognize that longevity is its own form of achievement.

I’ve also started thinking differently about risk.

When I was younger, risk usually meant taking action. Starting a company felt risky. Launching a product felt risky. Leaving a stable situation to pursue an uncertain opportunity felt risky.

I still believe those things involve risk, but I’ve come to realize that there are different kinds of risk that receive far less attention.

There’s risk in assuming growth will eventually solve problems that exist today.

There’s risk in ignoring fundamentals because you’re focused on future potential.

There’s risk in chasing opportunities that look exciting while overlooking opportunities that are already creating value.

There’s even risk in becoming too attached to a particular vision of what success is supposed to look like.

That last one is probably the most interesting to me.

When I look back at different stages of my career, I can see how much my definition of success was influenced by the environment around me. In startup circles, success often meant growth. In technology circles, success often meant innovation. In media circles, success often meant visibility. None of those things are inherently wrong, but they can become limiting if they’re the only metrics you pay attention to.

What I’ve discovered is that some of the happiest entrepreneurs I’ve met aren’t necessarily the most visible ones. They’re not constantly chasing the next thing. They’re not trying to impress anyone. They’ve simply built businesses that align with the lives they want to live.

That realization sounds obvious when you say it out loud, but I don’t think enough people spend time thinking about it.

A business is ultimately a tool.

It’s a tool for creating value, generating income, solving problems, supporting employees, serving customers, and ideally creating a life that feels meaningful to the person running it.

And the more I think about that, the more I wonder how many opportunities people overlook because they become attached to a particular image of what entrepreneurship is supposed to look like.

What I’ve come to appreciate over time is that entrepreneurship is much broader than the stories that receive the most attention. Every community has business owners solving problems, creating jobs, supporting families, serving customers, and building organizations that become part of people’s everyday lives. Many of those companies will never be featured in a magazine article or discussed on a podcast, yet their impact is very real.

I think that’s one reason this topic stayed with me longer than I expected. It reminded me that opportunity often exists outside the places where everyone is looking. Sometimes we’re so focused on the exciting path that we overlook the practical one. Sometimes we’re so interested in what’s new that we fail to appreciate what already works.

If I were giving advice to a younger entrepreneur today, I don’t think I’d tell them which path to choose. I wouldn’t tell them to build a startup, buy a business, become a consultant, create a media company, or pursue any specific model. What I would encourage them to do is spend more time understanding themselves before deciding what success is supposed to look like.

The reason that’s important is because every path comes with tradeoffs. Every opportunity requires sacrifices. Every business eventually asks something of the person running it. If you’re chasing someone else’s definition of success, those sacrifices can start feeling heavier over time. When your goals are aligned with who you are and what you genuinely want from life, the difficult parts of entrepreneurship tend to make more sense.

Looking back, I don’t think I would’ve made completely different decisions. I’ve enjoyed building things too much for that. The process of creating, experimenting, learning, and solving problems has shaped a huge part of my life. At the same time, I think I would’ve worried less about whether I was following the “right” entrepreneurial path and spent more energy understanding why certain opportunities appealed to me in the first place.

Anyway, those are some of the thoughts that have been bouncing around in my head lately. If nothing else, this whole topic reminded me that entrepreneurship is far more diverse, flexible, and personal than I once believed. The path that makes sense for one person may be completely wrong for another, and that’s probably a good thing. It means there are more opportunities available than we sometimes realize.

Thanks for listening, and I’ll see you in the next episode!