Jason Sherman

In this episode of Strap On Your Boots, I reflect on turning fifty and the biggest lesson I’ve learned after decades of building startups, making films, writing software, and exploring new ideas. Experience isn’t just about accumulating knowledge. It’s about developing judgment, recognizing patterns, and connecting lessons from projects that once seemed completely unrelated. I share how curiosity, failure, and continuous learning have shaped every stage of my career, and why your greatest advantage as an entrepreneur may be the experiences you’ve already lived through.

Listen to the podcast episode here:

Get ready to strap on your boots. I’m your host, Jason Sherman. In today’s episode I’m going to talk about experience, and how it can be your most powerful advantage when running a startup. Not because I’m trying to look back at my career or become nostalgic, but because I’ll be turning fifty this year, and I’ve started noticing something that I don’t think I appreciated when I was younger. There are moments now where I’ll be in a meeting, working on one of my companies, editing one of my films, or even recording this podcast, and I’ll instinctively know how to approach a problem without really thinking about why. Then later I’ll realize that the answer didn’t come from something I learned last week. It came from a conversation I had twenty years ago, a mistake I made ten years ago, or a project that completely failed but quietly taught me something I still use today.

When I was in my twenties, I assumed every new job or project was supposed to move me toward one specific career. If I learned programming, I figured I’d spend my life programming. If I started making films, then maybe filmmaking would become my identity. If I launched a startup, I thought entrepreneurship would eventually become the thing I was known for. Looking back now, I realize I was trying to organize my life into separate chapters, almost as if one experience would end before the next one began.

It didn’t work that way at all.

The more years that have passed, the more those experiences have started blending together in ways I never expected. Programming didn’t stop being useful because I became an entrepreneur. Filmmaking didn’t replace software development. Podcasting didn’t take me away from running companies. Every new pursuit kept layering on top of the previous ones, and somewhere along the way I stopped thinking about them as separate careers. They became different tools that I could draw from depending on the problem sitting in front of me.

I don’t think I understood that while it was happening because when you’re young, everything feels disconnected. You make decisions based on whatever opportunity is right in front of you, and it’s easy to wonder if you’re moving in too many directions. I remember questioning myself more than once. Was I spending too much time making films? Should I focus entirely on software? Was I dividing my attention too much by starting another business or launching another creative project?

Those questions felt important at the time because I assumed success belonged to people who picked one lane and stayed there.

As I’ve gotten older, I’m not so sure that’s true.

I started programming in the late 1990s because I genuinely loved building things. Back then, creating websites felt almost magical. You could write some code, upload it to a server, and suddenly people anywhere in the world could interact with something you had built. That curiosity eventually became a consulting business, and before I knew it, I was working with companies in completely different industries. Every client had unique challenges, different personalities, and their own way of making decisions. Without realizing it, I wasn’t just becoming a better programmer. I was getting an education in how businesses actually operate.

At the time, I probably underestimated how valuable that was.

Writing code teaches you how systems work. Consulting teaches you how people work. Those are very different things, and I needed both even though I didn’t know it yet.

Years later, I decided to make my first feature film. From the outside, that probably looked like I was changing careers, and maybe it even felt that way to me for a little while. I had no idea how much work went into producing a film from beginning to end. Suddenly I wasn’t just worrying about technology. I was coordinating people, managing schedules, solving unexpected problems, staying within a budget, and trying to keep a project moving forward despite constant obstacles.

None of those challenges felt very cinematic while I was living through them.

They felt remarkably similar to running a startup.

Both require bringing together people with different skills. Both involve making decisions with incomplete information. Both force you to balance creativity with practical limitations. Both require you to keep moving even when you aren’t completely sure you’ve made the right decision.

I didn’t realize it then, but filmmaking was preparing me for entrepreneurship in ways I couldn’t have predicted.

Then startups entered my life.

When I started building technology companies, I naturally leaned on my programming background because that was where I felt the most confident. If there was a technical problem, I knew I could solve it. Before long, though, I found myself facing problems that had nothing to do with software. I needed to explain products to investors. I needed to understand marketing. I had to think about branding, pricing, customer acquisition, hiring, fundraising, and every other challenge that comes with building a company.

Those weren’t subjects I had studied in school.

They became subjects I studied because my companies needed me to understand them.

Looking back, I find that really interesting because none of those skills were things I intentionally set out to master. I wasn’t sitting there making a list of everything I wanted to learn over the next twenty-five years. Every new project simply exposed another area where I wasn’t knowledgeable enough yet, and my curiosity usually got the better of me. I’d start reading books, watching interviews, talking to people with more experience, and slowly adding another piece to a toolkit that I didn’t even realize I was building.

If someone had asked me twenty years ago what I’d be doing at fifty, I don’t think I would’ve come anywhere close to describing the life I have today. I certainly wouldn’t have guessed that I’d be running software companies while making documentaries, hosting a podcast, speaking with entrepreneurs every week, and finding that each of those pursuits somehow makes me better at the others.

That’s the part I’ve been reflecting on recently, because I don’t think experience works the way I once imagined it would. It doesn’t simply accumulate. Given enough time, it begins connecting, and those connections often become far more valuable than any individual skill you picked up along the way.

As I’ve been thinking about this, I’ve started wondering whether the biggest advantage experience gives you isn’t knowledge at all. I think it’s judgment.

Knowledge is everywhere now. If I need to understand a programming language, a legal concept, a marketing strategy, or even how to use a new piece of software, I can find the information almost instantly. Twenty-five years ago, that wasn’t the case. You had to buy books, attend conferences, ask people you knew, or spend countless hours experimenting until something finally clicked. Today the information itself is rarely the bottleneck.

Judgment is different.

Judgment comes from living through situations where the answer wasn’t obvious. It comes from making decisions with incomplete information and then watching those decisions play out over months or years. Sometimes you were right. Sometimes you weren’t. Either way, you carry that experience into the next decision without even realizing it.

I notice that in my own work all the time now. There are situations where someone asks me a question, and I’ll have an opinion almost immediately. It isn’t because I’m smarter than anyone else in the room. It’s because the situation reminds me of something I’ve already lived through. Maybe it’s a startup partnership that feels familiar, a customer conversation I’ve had before, or a project that’s beginning to drift in a direction I’ve seen several times over the years. I recognize patterns much earlier than I used to because I’ve simply accumulated more of them.

That’s probably why I don’t get as discouraged by setbacks as I did when I was younger.

Back then, every obstacle felt permanent. If a product launch didn’t go well, I wondered whether the company itself was in trouble. If a client walked away, I questioned everything I had done leading up to that point. A failed partnership felt like evidence that I’d made the wrong decision from the very beginning.

Now those moments still matter, but they don’t carry the same emotional weight.

I’ve seen too many situations reverse themselves over time. I’ve watched disappointing meetings lead to great relationships months later. I’ve watched products that struggled at launch eventually find their audience after enough iteration. I’ve also seen exciting opportunities disappear almost overnight despite looking incredibly promising in the beginning.

Experience doesn’t remove uncertainty.

It changes your relationship with uncertainty.

Instead of assuming today’s outcome defines tomorrow’s possibilities, I’ve become much more comfortable letting things unfold. Sometimes the best decision becomes obvious only after you’ve gathered enough information, and that usually requires patience more than brilliance.

I also think experience changes the kinds of questions you ask.

Earlier in my career, I spent a lot of time wondering whether something could be built. That was naturally where my mind went because I was a programmer. My instinct was to solve technical problems, and I found a lot of satisfaction in figuring out how to make complicated systems work.

These days I’m much more interested in whether something should be built.

That sounds like a subtle difference, but it has probably saved me years of unnecessary work.

I’ve had plenty of ideas over the years that I could’ve turned into products. Technically, they were all possible. The harder question was whether they solved a meaningful problem, whether there was a sustainable business behind them, and whether I wanted to spend several years of my life bringing them into the world.

I don’t think twenty-five-year-old Jason would’ve asked those questions.

He probably would’ve started coding.

That’s not a criticism of my younger self because that curiosity is exactly what allowed me to develop the skills I rely on today. If anything, I’m grateful I was willing to chase ideas without overanalyzing them. At that stage of my life, building was how I learned.

Now I find myself learning in different ways.

A conversation with a customer teaches me something. Recording a podcast often helps me organize ideas that have been floating around in my head for weeks. Working on a documentary introduces me to historians, engineers, astronauts, or researchers whose perspectives end up influencing the way I think about entrepreneurship, even though those subjects seem completely unrelated on the surface.

Years ago I probably would’ve viewed those as separate parts of my life.

Now I can’t really separate them anymore.

The companies I build influence the questions I ask on this podcast. The conversations I have here often shape the way I think about my businesses. Making films has made me a better storyteller, and storytelling has made me much more effective when I’m pitching a product, speaking with investors, or simply trying to explain a complicated idea to someone who has never encountered it before.

I used to think I was constantly changing directions.

Looking back, I think I was slowly building connections between experiences that didn’t seem related until enough time had passed.

I also think something else changed without me really noticing it.

For a long time, I measured progress almost entirely by what I was building. If a company was growing, I felt like I was moving forward. If I finished a film, I immediately started thinking about the next one. Even this podcast started that way. I wanted to create conversations that entrepreneurs would enjoy listening to, but once I hit publish, my attention naturally shifted toward the next guest or the next topic. I rarely stopped to think about what each project was quietly adding to me while I was busy trying to finish it.

That probably explains why, for years, I kept feeling like I was changing directions.

I’d spend several years immersed in software, then disappear into filmmaking. After that I’d find myself back in the startup world, only to spend more time speaking at events or recording podcasts. If someone had looked at my résumé during any one of those periods, they might’ve wondered why I couldn’t make up my mind.

The funny thing is that I never felt that uncertainty while I was doing the work. I was simply following whatever problem seemed interesting enough to deserve my attention.

Only now do those years make sense to me.

Working on Before the Moon is probably the best example. On the surface, it doesn’t have much to do with building software companies. One is a historical documentary about aerospace medicine, and the other involves startups and technology. They couldn’t look more different. Yet while I was making the film, I found myself using almost every skill I’d developed over the previous twenty-five years.

Running interviews reminded me of conversations I’d had with customers. Organizing years of research wasn’t much different than organizing a complicated software project. Marketing the documentary forced me to think about audiences in exactly the same way I think about launching a product. Even raising support for the film felt surprisingly similar to pitching investors. Different words, different goals, but many of the same fundamentals underneath.

I don’t think I could’ve made that film twenty years ago.

Not because I wasn’t capable of learning how to shoot interviews or edit video. I probably could’ve figured those parts out. What I don’t think I had yet was enough life experience to manage something that large without becoming overwhelmed by it.

That’s actually one of the things I’ve started appreciating about getting older.

The projects haven’t necessarily become easier.

I just don’t react to every challenge the way I used to.

If something unexpected happens, I don’t immediately assume the project is falling apart. Somewhere in the back of my mind, I know I’ve probably dealt with something similar before. Maybe not the exact same situation, but close enough that I trust myself to work through it.

That feeling is difficult to describe because it isn’t confidence in the traditional sense.

It’s more like familiarity.

You’ve lived through enough difficult weeks that another difficult week doesn’t convince you everything is headed in the wrong direction.

I also spend a lot less time worrying about whether every project fits neatly into the last one.

Years ago, I would’ve asked myself whether making a documentary was distracting me from my software companies.

Today I don’t really think that way anymore.

If a project teaches me something valuable, I trust that it’ll become useful somewhere else eventually, even if I have no idea when that will happen.

Looking back, that’s happened too many times to ignore.

The communication skills I use when speaking with investors show up during podcast interviews. The patience I developed making films helps when enterprise sales move slower than I’d like. Building startups taught me how to solve problems quickly, and that mindset has been invaluable in almost every creative project I’ve taken on.

None of those experiences replaced one another.

They quietly accumulated until they became difficult to separate.

Maybe that’s why turning fifty doesn’t feel like reaching some finish line.

It feels more like reaching a point where I can finally see the connections between things that once seemed completely unrelated. Twenty-five-year-old Jason would’ve looked at programming, filmmaking, entrepreneurship, podcasting, and writing as entirely different careers. From where I sit today, they all feel like different expressions of the same curiosity that’s been following me around since I first started building websites in the late nineties.

I have no idea what I’ll be working on ten years from now.

If my past is any indication, it’ll probably be something I can’t predict today. It’ll probably force me to learn another set of skills I don’t yet have, and years after that I’ll find myself borrowing pieces of that experience in ways I never could’ve anticipated.

That’s become one of my favorite parts of building a career.

You spend decades wondering whether all the different paths you’re taking actually connect.

Then one day you wake up and realize they already have.