Jason Sherman

In this episode of Strap On Your Boots, I explore how artificial intelligence is transforming entrepreneurship by making it easier than ever to turn an idea into a working product. Drawing from my early experiences building Gugo, Picklify, and Instamour, I reflect on the years when launching a technology startup required expensive developers, complicated programming, and months of work. Today, tools like Cursor, Claude, and ChatGPT can help entrepreneurs build functional applications in days. But while the technology has changed dramatically, the biggest challenge remains the same: finding customers who actually want to use what you’ve built. I explain why building a community, getting your first 100 users, collecting feedback, and learning how to market your product are more important than ever.

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’s changed dramatically since I first started building technology companies, and that’s how easy it’s become to turn an idea into an actual working product. I look at what people are doing today with artificial intelligence, tools like Cursor, Claude, and ChatGPT, and I’m genuinely amazed by how quickly somebody can build something that would have taken me months, sometimes even a year, to create when I was first getting started. And I’ll admit, I’m a little jealous of the younger entrepreneurs who have these tools available to them because I remember how incredibly difficult it used to be.

Back in the late 1990s and early 2000s, I was already building websites, working with computers, and learning different technologies. I could put together HTML websites, design pages, and figure out a lot of the basic things that people needed on the internet at the time. But there was an enormous difference between building a website and building an actual software platform. Once you started talking about databases, user accounts, transactions, messaging, and all the functionality that makes a modern application work, things became considerably more complicated.

I remember taking a PHP and MySQL course because I wanted to understand how to build database-driven websites. I was interested in creating something closer to an e-commerce platform, where users could interact with information and actually do things rather than simply read a webpage. And even after taking that course, I still couldn’t completely wrap my head around how everything worked together. I understood pieces of it, but connecting those pieces into a functional product was another story.

Around 2005 or 2006, when Facebook was starting to become popular, I already had ideas for what would eventually become Instamour, my video dating platform. I could picture what I wanted the product to do, and I had a pretty good understanding of how I wanted people to interact with it. The problem was that I couldn’t build it myself. I tried learning more programming, taking courses, and experimenting with different tools, but the technology was a major obstacle.

And when I think about that today, it’s incredible how much has changed. Somebody can now describe an application to an AI coding tool, explain what screens they want, how users should interact with it, and what functionality they need, and within minutes they can have something that actually resembles a working product. Obviously, there’s still work involved in making something reliable and ready for real customers, but the difference in getting started is enormous.

I remember a particularly frustrating experience around 2010, right after I finished making my film The Bucks County Massacre. Someone who had worked on the movie wanted to continue collaborating with me, and we eventually connected with a programmer who was interested in starting a technology company. I still had my video dating idea, but the other guys wanted to build something different, so we started working on a social platform called Gugo, which stood for Get Up, Go Out.

The concept was that groups of friends could organize activities, go places together, and earn points that could eventually be redeemed for discounts. We thought of it as something of an alternative to Facebook because we wanted people to spend more time actually doing things together in the real world. Facebook was becoming such a dominant part of people’s social lives, and we thought there was an opportunity to create something that encouraged people to get out of the house.

But even getting that idea off the ground was incredibly complicated. The movie The Social Network had recently come out, and everybody was suddenly concerned about the legal side of starting a company. We were talking about lawyers, contracts, ownership, and all these things before we had even finished building the platform. Meanwhile, I was trying to figure out how to design the interface.

At the time, I was still using programs like Dreamweaver. I could design websites, but building an entire social platform with all those different screens and interactions was beyond what I could comfortably do myself. I ended up hiring a development company in India to help with the design, and the whole process took weeks of communicating back and forth, reviewing screens, and trying to get everything looking the way I imagined.

Today, I could open Cursor or Claude, describe that same interface, and probably have a pretty impressive first version within minutes. I could make changes simply by explaining what I wanted, rather than spending hours adjusting code or sending revisions to somebody on the other side of the world.

And that was only the design. Back then, once you had something that looked good, you still had to figure out how to make it function, connect everything to databases, and find servers to host the application. Every stage required another level of technical knowledge, time, and usually money.

Looking back, I think that’s what made starting a technology company so intimidating. You could have a genuinely interesting idea and still spend an entire year just trying to get something functional enough for people to use.

And that’s exactly what happened with Gugo. We spent about a year trying to get the company off the ground, dealing with development challenges, disagreements about the direction of the business, and all the other complications that come with starting something from scratch. Eventually, we went our separate ways, but I learned a tremendous amount from that experience. I learned about working with cofounders, trying to manage developers, and how difficult it was to get a technology product built when you didn’t have a lot of money or the technical expertise to do everything yourself.

After that, I moved on to another idea called Picklify, which was an e-commerce platform that I started working on around 2011. I had been looking at companies like eBay and Craigslist, and I thought there was an opportunity to create something that worked a little differently. Instead of sellers listing products and buyers competing to purchase them, I wanted buyers to be able to tell the marketplace what they were willing to pay. Sellers could then decide whether they wanted to accept that price. It was essentially a reverse auction marketplace.

I also wanted to make the experience much more social. At the time, buying something on Craigslist was relatively anonymous, and even on eBay, you didn’t really know much about the person on the other side of the transaction. With Picklify, I wanted people to have actual profiles, with photographs, biographies, links to their social networks, and the ability to chat directly with each other. I thought that if people could learn more about who they were buying from or selling to, it might create a more personal experience.

This time, I found a local developer who was incredibly talented, and we were actually able to build the platform. The reverse auctions worked, people could buy and sell things, and the functionality we had envisioned was there. I remember how exciting that was because after struggling for so long with previous projects, I finally had a real application that people could use.

But then we ran into the problem that has followed me through almost every startup I’ve ever built. How do you get people to actually use it?

We didn’t have a substantial marketing budget, so we did what we could. We attended technology meetups, talked to people at colleges, and tried to introduce the platform to anybody who might be interested. We could explain how it worked and demonstrate the features, but convincing people to sign up and become active users was an entirely different challenge. And with a marketplace, you have the additional complication of needing both buyers and sellers. Somebody might love the concept, but if there aren’t enough products available, there’s not much reason for them to keep coming back.

I think about that experience whenever I see somebody today announcing that they’ve built an entire application over the weekend using artificial intelligence. I’m genuinely happy that people can do that now. I wish those tools had existed when I was struggling to build Gugo and Picklify. It would have saved me an enormous amount of time and money, and I probably could have tested a lot more ideas without having to spend months finding developers and figuring out the technology. But I also wonder what happens after that weekend.

You’ve got your application running. You’ve designed a nice interface, connected a database, and maybe even integrated payments. You can show it to your friends, post screenshots on social media, and tell everybody that you’ve launched a startup. That’s exciting, and I don’t want to diminish that accomplishment because creating something from an idea is always rewarding.

But now you need people to use it. And that’s where I think the difficulty of entrepreneurship hasn’t changed nearly as much as the technology has.

When I was building companies fifteen years ago, we needed investors to help us pay for development, hosting, and everything else involved in getting a platform launched. We’d put together pitch decks, attend meetings, and try to convince people that our ideas were worth funding. And even back then, investors wanted to see traction. They wanted evidence that people were interested in what we were building, and ideally that there was some potential to generate revenue.

Today, development is considerably more accessible, but those questions are still there. If somebody can build a prototype in a weekend, that’s fantastic. But can they convince a hundred people to try it? Can they get those people to keep using it? Can they learn enough from those first users to make the product better?

And I think that’s where I would encourage younger entrepreneurs to spend a lot more of their time. Because now that the technical barriers have come down, the opportunity to experiment is incredible. You can build something small, release it, and start learning from real people much earlier than I ever could.

If I were starting my first technology company today, I would probably approach it very differently than I did fifteen years ago. I would still spend time thinking about the problem I wanted to solve, and I’d still want to build something interesting. But knowing what I know now, I would put just as much effort into finding my first hundred users as I would into developing the product itself. Because those hundred people can teach you an enormous amount about whether you’ve actually built something worthwhile.

And I’m talking about people who genuinely want to use your product. People who have the problem you’re trying to solve and are willing to spend time testing your solution. Ideally, they’re excited enough about what you’re building that they want to see you succeed. They’ll tell you when something doesn’t work, they’ll suggest improvements, and they’ll come back to see what you’ve changed. Some of them might even start telling their friends about it.

I’ve always believed that building a community around a product is one of the most valuable things an entrepreneur can do. And now that technology is so much easier to create, I think that community becomes even more important.

Let’s say you’ve got an idea for an application. Maybe it’s something that helps people organize their lives, manage a business, or connect with other people who share their interests. You could spend a weekend building the first version with AI, and by Monday you’ve got something functional enough to demonstrate. That’s an incredible opportunity compared with what I went through with my early startups.

But rather than immediately spending the next six months adding features, I’d start figuring out where the people who need that product are spending their time.

Maybe they’re on Reddit discussing the problem. Maybe there are Facebook groups dedicated to that particular subject. Maybe there’s an existing community on LinkedIn, Discord, or another platform where people are already talking about the challenges your application is designed to address. I would start participating in those conversations, learning what people are struggling with, and introducing the product when it’s relevant.

And I would do some of that before the product was even finished. I don’t see any reason to wait until launch day to start building relationships with potential customers. You can show people early designs, ask questions, and find out whether they’re interested in testing something. By the time you’re ready to release a beta, you might already have a group of people who are waiting to try it.

That’s a much better position to be in than spending months building something and then wondering where you’re going to find customers.

Once I had my first hundred users, I would spend time talking to them and understanding their experience. I’d want to know what they liked, what confused them, whether they were coming back, and what would make the product more useful. Then I’d take that information and improve the platform.

After that, I’d work toward five hundred users. And then a thousand. And eventually five thousand, ten thousand, and hopefully considerably more.

Those numbers aren’t magic milestones, and every business is different. A company selling enterprise software might have a very successful business with twenty paying customers, while a consumer social platform might need hundreds of thousands of active users before it becomes financially sustainable. The important thing is that you’re gradually expanding your audience while learning from the people who are already using the product.

And you have to learn how to market it. I know a lot of technical founders don’t particularly enjoy that part of entrepreneurship. They would rather spend their time programming, designing interfaces, and creating new functionality. I understand that because I’ve spent plenty of time doing exactly the same thing.

But learning how social media works, understanding advertising, participating in online communities, and figuring out how to explain your product to potential customers are skills that every founder should develop. You don’t necessarily need to become a professional marketer, but you do need to understand how people discover products and what makes them interested enough to try something new.

And if you eventually want to raise venture capital, having a growing community of active users can make a tremendous difference. Investors hear ideas all day long. They see pitch decks, prototypes, and demonstrations of products that might become successful someday. But if you can show them that a hundred thousand people are actively using your platform, or that you’ve built a business with meaningful recurring revenue, you’re having a very different conversation.

Of course, a large user base doesn’t automatically guarantee funding. Investors will still want to understand your business model, retention, growth, and whether the company has the potential to become profitable. But you’re giving them something concrete to evaluate instead of asking them to believe that people might eventually want what you’re building.

And that’s what I find so exciting about the technology available today. I remember struggling with Dreamweaver, trying to understand PHP and MySQL, hiring developers, and spending months attempting to get relatively simple ideas off the ground. Now somebody with very little programming experience can experiment with an idea and potentially have something usable in front of customers within days.

I would encourage anybody who’s been thinking about starting a company to take advantage of that. Build the prototype. Experiment with the tools. Find out whether you enjoy the process of creating something.

But while you’re doing that, start finding the people you’re building it for. Get them involved early, listen to what they’re telling you, and give them reasons to stick around as the product improves.

Because when I look back at all the companies I’ve started, the technology has changed enormously, but the challenge of getting people to care about something new has been there every single time. And if I were starting over today, that’s where I’d be putting most of my attention.