Jason Sherman

In this episode of Strap On Your Boots, I explore why marketing a technology startup can be so much harder than promoting a movie. Drawing from my experiences building Instamour, Spinnr, Vengo AI, and Campus Pixel, I explain how changing products, shifting customer markets, and evolving business models can make startup marketing a constant challenge. I also share how I marketed my documentary Before the Moon, combining grassroots community outreach, social media, local publicity, and targeted advertising to sell out an 850-person premiere. Whether you’re launching software or promoting a creative project, understanding your audience before spending money on marketing can make all the difference.

Listen to the Podcast:

Get ready to strap on your boots. I’m your host, Jason Sherman, and today I want to talk about something that I’ve been dealing with for pretty much my entire entrepreneurial career, and that’s marketing. Specifically, why so many startups struggle with marketing, even when they’ve built something that they genuinely believe people are going to love. I’ve built a lot of technology platforms over the years, and I’ve also made several feature films, and one thing I’ve discovered is that marketing a movie is a million times easier than marketing a technology startup. And I think understanding why that’s the case can teach us quite a bit about how we should approach building and marketing our companies.

When I launched Instamour back in 2013, I didn’t really have a traditional marketing strategy. I knew that online dating was broken in a lot of ways, and one of the biggest problems at the time was catfishing. People were creating profiles using pictures that weren’t theirs, and you could spend weeks talking to somebody without knowing whether they were actually the person in those photographs. Video wasn’t really being used in dating apps yet. Vine had launched right around the same time as Instamour, within weeks of each other, so short-form video was just starting to become something people were familiar with on their phones.

My thinking was pretty straightforward. If people could create video dating profiles, they would have a much better idea of who they were talking to. You could see somebody’s personality, hear their voice, and get a sense of what they were like before deciding whether to meet them. That was the problem I wanted to solve, and it gave me something very specific to talk about when I started introducing the app to people.

I went to local colleges with my prototype and started getting students to try it. I wasn’t working with some enormous marketing budget or a sophisticated advertising agency. I was physically going out and talking to people about the product. I created college competitions where students could make video profiles, and we offered prizes like cash, gift cards, and video game consoles. I printed flyers and used social media to spread the word. I was also speaking at colleges about entrepreneurship, analytics, and what it takes to build a startup, which gave me another opportunity to introduce people to what I was working on.

Looking back, I think what helped was that I could explain the problem immediately. People understood what catfishing was. They understood why photographs weren’t always reliable. I didn’t have to spend twenty minutes educating somebody about why video dating might be useful. They could make that connection pretty quickly, and then the challenge was convincing them to actually try the app.

Now, that doesn’t mean having a good pitch automatically makes a startup successful. I’ve learned that plenty of times. You still need people to keep using the product, and you have to figure out whether there’s a business model that can support it. But at least I had something that resonated with the people I was trying to reach.

Over the years, Instamour eventually evolved into Spinnr, which focused on helping people make friends through video. And when we started incorporating artificial intelligence into Spinnr, something interesting happened. We had created an AI friend and helper that could assist people with navigating the platform, but also give them somebody to talk to. People in our community became interested in having their own version of that AI, and that feedback eventually led us to create Vengo AI.

Initially, we built Vengo as a consumer product because that’s where the demand appeared to be coming from. We had people telling us they wanted it, so we listened and built around that interest. But once we got further into the process, we started discovering that businesses were much more interested in using the technology commercially.

That changed everything about how we approached the company, including how we marketed it.

We moved from a consumer product into business-to-business software, then into a SaaS model targeting small businesses, and eventually toward enterprise customers, including Fortune 500 companies. We also developed Campus Pixel for universities. Each time we changed direction, we had to rethink who we were talking to, what problems we were solving, and how we explained the value of the technology.

And that’s something I don’t think people appreciate enough about marketing a startup. Sometimes you’re trying to promote a product while you’re still discovering what the product is ultimately going to become.

And every time you make one of those changes, you’re almost starting over with your marketing. The messaging that worked when we were talking to consumers about having an AI friend wasn’t necessarily going to work when we started talking to business owners about using AI to engage with their customers. And once we started pursuing larger enterprise clients, we were having completely different conversations. These companies have different expectations, different budgets, and different reasons for wanting the technology. So even though the underlying product had evolved from the same original idea, the way we presented it had to change considerably.

I think that’s one of the reasons founders get frustrated with marketing. They might spend months creating a website, developing their branding, writing social media posts, and trying to build an audience, only to discover that they’re targeting the wrong people. Then they have to go back and change everything. I’ve been through that process multiple times, and while it can be exhausting, I also think it’s a necessary part of figuring out where your product belongs in the market.

And this is where I always come back to talking to customers. I don’t think you can sit in a room with your cofounders and decide what everybody else is going to want. You can certainly come up with an idea based on a problem you’ve experienced yourself, and that’s usually a good place to start. But then you have to find out whether other people have that same problem. I spend time talking to people, looking at discussions on Reddit and Facebook, and paying attention to what people are complaining about. Sometimes you’ll discover a problem that people have been dealing with for years because nobody has come up with a particularly good solution.

Once I find something interesting, I want to test whether people actually care enough to use a product that addresses it. And ideally, whether they’re willing to pay for it. That’s an important distinction because I’ve built plenty of things that people thought were interesting, but getting somebody to say they like your idea is very different from getting them to become a paying customer.

That’s also why I don’t believe you should spend a year building an enormous platform before introducing it to the market. I’d rather build a small version that demonstrates the core value, get people using it, and start asking questions. What do they like? What confuses them? What would they pay for? Are there things they expected the product to do that it doesn’t do yet? Those conversations help me understand what I’m actually marketing, and they also help me figure out what I should be building next.

But something else I’ve discovered through all of this is that I approach marketing very differently when I’m making a movie.

With my films, I usually start by researching a subject that already has an established community around it. Take my documentary Before the Moon, which tells the story of the Johnsville Centrifuge and the people who helped prepare astronauts for spaceflight. I knew there was an enormous community of people who love NASA, space exploration, astronauts, rocket launches, and aerospace history. These are people who spend their free time watching launches, visiting museums, reading books about space, and learning about the history of the space program.

So before I even finished making the movie, I had a pretty good understanding of who might want to watch it.

That makes a tremendous difference when you’re trying to market something. I don’t have to convince somebody that space exploration is interesting if they’ve already spent their entire life being fascinated by it. I just have to introduce them to a story they might not have heard before and explain why I thought it was worth making a documentary about.

And because it’s a movie, I have a finished product that I can promote consistently. I can create a trailer, show people photographs, share clips from interviews, and talk about the history behind the film. The story doesn’t change every few months because I’ve decided to target a different customer segment or introduce a new business model.

When I was preparing for the premiere of Before the Moon, I could spend my time figuring out how to reach that existing audience. And the approach I took was surprisingly old-fashioned in a lot of ways, especially considering how much of marketing today revolves around digital advertising.

I started promoting the premiere by doing a lot of the things I had done when I was marketing my early startups. I created social media videos, photographs, graphics, and flyers. I printed stacks of those flyers and started distributing them throughout Bucks County. I went into local businesses, attended events, mailed flyers to people, and tried to make sure that wherever somebody might hear about the film, there was an opportunity for them to learn about the screening.

I also submitted the event to local newsletters and community calendars, including Visit Bucks County. I reached out to journalists, and we ended up getting some articles published about the documentary and the premiere. All of those things helped build awareness, and I think people sometimes underestimate how effective local community marketing can be. Everybody talks about social media advertising, but there’s still something valuable about physically showing up in the community where you’re trying to sell tickets.

Before I spent any money on advertising, I had already sold around 300 tickets. That was pretty encouraging because it showed me that the interest was there. People were responding to the subject matter, the story, and the opportunity to attend a screening at the actual location connected to the documentary.

Then I started running Meta ads, primarily through Facebook and Instagram, and that’s when ticket sales really accelerated. We eventually sold out the premiere with approximately 850 people attending. It was an incredible experience, especially because I had spent about a year making the film and was now seeing hundreds of people come together to watch it.

And I think there’s an important marketing lesson in how that happened. The advertising helped tremendously, but I had already spent months building awareness, connecting with the community, and giving people reasons to care about the film. I also had a specific event, a location, and a date that people could make plans around. That’s very different from asking somebody to sign up for another software platform that they may or may not need.

With technology, the marketing never really ends. I have to keep finding customers, improving the product, fixing bugs, adding functionality, and explaining why somebody should choose our platform. With a movie, once I’ve finished it, I can concentrate on reaching the people who might enjoy it. The film itself stays the same, and over time I get better at explaining why people should watch it.

Of course, marketing films has changed dramatically since I started making them. Back around 2010, and really up until the pandemic, I relied much more heavily on film festivals, in-person screenings, and traditional distribution. Those opportunities still matter, but now there’s a much greater emphasis on building an audience online.

Today I maintain a website where people can buy merchandise, and I continue organizing screenings because those can generate revenue directly. I also spend a tremendous amount of time creating social media content, sharing clips, posting photographs, and engaging with people who are interested in the subject. And when a distribution company evaluates a film, having an existing audience that wants to see it can make the project more attractive.

The interesting thing is that I’ve learned to apply some of those same principles to my technology companies, even though the marketing is considerably harder.

I want to know where my potential customers are already spending their time. I want to understand what they’re talking about and what problems they’re trying to solve. And I want to be able to explain what I’ve built in language that makes sense to them. If I’m talking to a university about Campus Pixel, I need to understand the problems universities are facing. If I’m talking to an enterprise company about Vengo AI, that conversation is going to be completely different.

And sometimes the product I personally want to build isn’t necessarily the product the market wants to buy. I’ve had to accept that over the years. I love coming up with new ideas and creating things, but many of those ideas would require an enormous user base before they could generate meaningful revenue. Getting a million people to use a platform is incredibly difficult, and investors generally want to see evidence that the business can eventually make money.

That’s partly why I continue making films alongside my technology companies. Filmmaking gives me an opportunity to pursue stories I’m passionate about, while my technology businesses require me to pay much closer attention to what customers are willing to purchase.

I recently had a woman come up to me after a screening of Before the Moon and tell me how much the film meant to her. She talked about the importance of preserving these stories and how much she appreciated the work that went into making the documentary. Those conversations remind me why I enjoy filmmaking so much.

But whether I’m making a movie or building software, I still have to understand the audience. I can be passionate about something and spend an enormous amount of time creating it, but that doesn’t automatically mean other people will care.

So when I think about why startups struggle with marketing, I keep coming back to the research that happens before the marketing even begins. Have I found people who genuinely need what I’m building? Have I spent enough time talking to them? Do I understand how they describe the problem? And can I explain why my product is worth their attention?

Those are questions I still ask myself with every company I build. Because even after all these years, I’m still learning what works, and every new product gives me another opportunity to figure it out.