Jason Sherman

In this episode of Strap On Your Boots, I share one of the biggest mindset shifts I’ve had as an entrepreneur: why I stopped searching for the perfect co-founder and started focusing on building the vision first. Looking back at my early startups, I realized that talented people alone aren’t enough if everyone has a different picture of where the company is headed. I explain how building prototypes, attracting early users, and creating momentum on my own helped me find teammates who believed in the vision instead of helping define it. If you’ve been waiting for the right partner before getting started, this episode may change how you think about launching your next company.

Listen to the Podcast:

Get ready to strap on your boots. I’m your host, Jason Sherman. Today I want to talk about something that has come up in conversations with my peers lately. I honestly wish I had understood this years ago, because it would’ve changed the way I approached almost every software company I’ve built.

For most of my career, I believed that building the product was going to be the hard part. That probably sounds obvious because, at the time, it really was. Software took a long time to develop, hiring engineers wasn’t cheap, and getting an idea from a whiteboard into the hands of real customers could take months or even years. If you could successfully launch something that actually worked, you felt like you’d crossed the biggest hurdle.

Somewhere along the way, that stopped being true.

I don’t remember exactly when it happened because it wasn’t one dramatic moment. It was something I slowly noticed after building more companies and watching the startup ecosystem change around me. Every year it became easier to create software. Better frameworks appeared. Cloud infrastructure became more accessible. APIs eliminated problems that developers used to spend weeks solving. Then no-code platforms arrived, and now AI can generate working applications from a prompt that would’ve required an entire development team not very long ago.

I actually think that’s one of the best things that’s happened to entrepreneurship. More people have the opportunity to build something than ever before, and that’s exciting because good ideas shouldn’t be limited to people who know how to write code.

What took me longer to appreciate was that lowering the barrier to building products also raised the difficulty of getting anyone to notice them.

That’s the tradeoff I don’t think we talk about enough.

When I launched some of my earlier companies, competition certainly existed, but it felt manageable. Today it seems like every problem already has dozens of solutions. If you’re building productivity software, there are hundreds of productivity apps. If you’re creating marketing software, there are countless marketing platforms. Even highly specialized industries now have startups focused on solving problems that would’ve seemed too small ten years ago.

I don’t say that as a complaint. It’s simply the reality of building businesses today.

The part that surprised me wasn’t seeing more competition. It was realizing that building a better product didn’t automatically make customer acquisition any easier.

I’ve experienced that firsthand.

Getting a product into the hands of the first few customers has never been the part that kept me awake at night. Between people I know, conferences, partnerships, referrals, social media, and simply reaching out to businesses directly, you can usually find those early adopters. They’re willing to try something new, give feedback, and help you improve the platform.

The challenge always seemed to begin after that initial momentum wore off.

That’s where I started asking myself a different question.

Why is it that getting the first twenty customers feels achievable, but getting the next thousand feels almost impossible?

The more I thought about that question, the more I realized I had been looking at the problem from the wrong angle.

For years I kept asking myself how I could make the product better. I’d think about new features, a cleaner interface, additional integrations, improvements to the user experience, or ways to simplify the onboarding process. Those are all worthwhile things to focus on because every product should continue improving. But eventually I had to admit that those improvements weren’t solving the problem I was actually facing.

The challenge wasn’t that people disliked the software.

The challenge was getting enough of the right people to see it in the first place.

Those are completely different problems.

I’ve seen founders spend months debating features that maybe five percent of their users would ever notice while almost no time is spent discussing how they’re actually going to reach the next thousand customers. Looking back, I’ve been guilty of that myself. It’s much easier to spend another week refining a product than it is to put yourself out there, start conversations, hear objections, and figure out why someone would choose your platform instead of the dozens of alternatives they already know about.

That’s probably one of the biggest changes I’ve noticed over the last decade.

The bottleneck isn’t usually technology anymore.

It’s attention.

People have more choices than they’ve ever had before. They have more software, more content, more emails, more advertisements, and more people asking for their time every single day. Even if your product genuinely solves a problem, you still have to earn enough attention for someone to give it a chance. That’s becoming harder every year because everyone else is competing for the exact same thing.

I experienced this with SaaS products over and over again.

The subscription model sounds fantastic when you first hear about it. You imagine building software once and collecting recurring monthly revenue while continuing to improve the platform over time. Investors love recurring revenue because it creates predictable income, founders love it because customers can stay for years, and on paper the math looks incredibly attractive.

Then you start living that reality.

Getting ten paying customers feels exciting because every new signup is proof that someone sees value in what you’ve built. Reaching fifty customers feels like real momentum. Somewhere after that, though, the pace often changes. Growth slows down, marketing becomes more expensive, and you start discovering something that isn’t obvious when you’re drawing financial projections on a whiteboard.

Every month doesn’t begin at zero.

It begins with customers deciding whether they’re going to stay.

Some continue because they genuinely depend on your platform. Others cancel because they found another solution, their priorities changed, budgets were cut, or they simply stopped using the product. Whatever the reason, you’re constantly balancing two goals at the same time. You’re trying to bring new customers into the business while also keeping the existing ones happy enough to remain there.

That dynamic changes the way you think about growth.

It’s no longer enough to attract attention. You have to keep earning it month after month, and that usually requires a level of marketing, customer support, product development, and communication that many founders underestimate during the early stages of a company.

I know I underestimated it.

There were times when I’d look at the number of people signing up for a platform and feel encouraged, only to realize later that maintaining steady growth required far more than simply having a good product. It required consistent visibility. It required ongoing marketing. It required reaching people who had never heard of us before while continuing to deliver enough value that existing customers never felt the need to look elsewhere.

That’s a difficult balance, especially if you’re a small company competing against businesses that have raised millions of dollars.

I don’t say that because I think venture-backed companies have an unfair advantage. Raising money creates its own pressures and expectations. But having access to significant capital absolutely changes what’s possible from a marketing perspective. If a competitor has the resources to hire large sales teams, invest heavily in advertising, sponsor conferences, produce constant content, and acquire customers at a loss while they’re growing, they’re playing a very different game than a bootstrapped startup trying to fund everything from revenue.

Eventually I stopped asking myself how I could outspend companies with much larger budgets because I already knew I couldn’t.

Instead, I started asking a different question.

What if I stopped trying to compete in exactly the same market?

That question ended up changing the direction of my company more than any feature we ever built.

At first I thought the answer might be finding an even smaller niche. I’ve talked about niche markets for years because I still believe they’re incredibly important. Trying to build software for everyone usually means you end up building something that doesn’t deeply solve anyone’s specific problem.

This time, though, the realization went a little further.

It wasn’t only about choosing a niche.

It was about choosing a completely different customer.

That distinction turned out to matter much more than I expected.

Once I started looking at the problem through that lens, I realized I had been making an assumption that I never really questioned.

I assumed success meant convincing thousands of customers to pay a relatively small monthly subscription.

That’s the model we hear about all the time. Build a SaaS platform, charge somewhere between thirty and a hundred dollars a month, keep growing your customer base, reduce churn, and eventually reach the scale where the recurring revenue becomes meaningful. It’s an attractive model, and there are plenty of companies that have executed it incredibly well.

The problem was that I kept looking at those success stories without fully appreciating what it took to get there.

Behind every company with ten thousand paying customers is an enormous amount of sales, marketing, advertising, partnerships, customer support, and brand recognition. It isn’t simply the product that got them there. It’s everything surrounding the product that most people never see.

As I started looking more carefully at our own business, I found myself asking a question that seemed almost too obvious.

If I need one thousand customers paying fifty dollars a month to reach my revenue goals, why am I assuming that’s the only path available?

What would happen if I found one customer willing to pay fifty thousand dollars instead?

That sounds like a completely different business, and in many ways it is.

Instead of asking thousands of small businesses to justify another monthly subscription, I began talking to organizations with much larger problems to solve. Universities and enterprise companies weren’t looking for another inexpensive tool to experiment with. They were looking for solutions that could be integrated into their existing operations, customized for their specific needs, and supported over the long term.

That changed almost every conversation we had.

We stopped leading with price and started talking about outcomes.

We spent less time explaining individual features and more time understanding the problems each organization was trying to solve. Those meetings became much more collaborative because we weren’t trying to convince someone to click a “Start Free Trial” button. We were discussing whether our technology could genuinely become part of their organization.

I also discovered that enterprise sales require a completely different kind of patience.

With consumer software, people often make decisions in minutes. They land on your website, compare a few products, maybe start a free trial, and either subscribe or move on.

Large organizations don’t work that way.

A conversation today might lead to another meeting next month. Then legal reviews the agreement. Procurement gets involved. Department heads want demonstrations. Budgets have to be approved. Sometimes a board needs to review the decision. It can feel painfully slow if you’re used to the pace of startup life.

Earlier in my career, I probably would’ve found that frustrating.

Now I understand that’s simply how large organizations manage risk.

When a company is investing tens of thousands of dollars into a platform, they should ask difficult questions. They should evaluate alternatives. They should involve multiple people in the decision. If I were sitting on the other side of the table, I’d probably do exactly the same thing.

Ironically, once I accepted that slower pace, the entire process became less stressful.

I stopped measuring progress by how quickly contracts were signed and started measuring it by whether we were building relationships with organizations that genuinely valued what we had created. Those relationships took longer to develop, but they also tended to be much stronger because both sides invested significant time understanding whether we were the right fit.

I don’t think this means enterprise software is the right answer for every startup.

It certainly wasn’t the right answer for every company I’ve built.

What changed was my understanding that business models aren’t one-size-fits-all. Sometimes entrepreneurs spend years trying to force a product into a market that simply isn’t the best match for it. The product itself may be valuable. The customer may simply be someone different than the person you originally imagined.

Looking back, that’s probably the biggest lesson I’ve taken away from this entire journey.

For a long time, I believed differentiation came from building better technology.

Today I think differentiation often comes from understanding your customer more deeply than your competitors do.

Technology is important. Product design matters. User experience matters. But none of those things exist in isolation. A great product still has to solve a meaningful problem for someone who’s willing and able to pay for that solution.

Once I started thinking that way, I stopped obsessing over whether our software had every feature a competitor offered. Instead, I became much more interested in whether we were solving the right problem for the right customer.

That shift changed the conversations we were having, the products we were building, and ultimately the direction of the company.

I don’t know what building software will look like another ten years from now. Technology is changing too quickly for anyone to predict that with confidence. What I do believe is that differentiation will probably become even more important than it is today. As the tools for creating software continue improving, more people will be able to build impressive products, and that’s something I genuinely think is good for entrepreneurship.

It also means founders will need to spend even more time understanding who they serve and why those customers should choose them over every other option available.

That’s the part I wish someone had explained to me much earlier in my career.

Building the product was never the finish line.

It was simply the beginning of a much longer conversation with the market, and learning how to listen to that conversation has probably been one of the most valuable skills I’ve developed as an entrepreneur.

I’d love to hear what you think about this topic. Feel free to write a comment below and tell me your thoughts.