Anne Weiler.

At first glance one might think a tech startup and a feature film are worlds apart. Yet, as it happens, bootstrapping and building a tech company and producing an independent feature film are surprisingly similar. This was something that surprised me as I pivoted from startup CEO to movie producer.

What can you learn from this? Your skills may be more transferrable than you thought, grit matters a lot, as do equal doses preparedness and luck.

Years after co-founding Wellpepper, a digital health startup, I produced This Bloody Country, an independent feature film, and I had expected the two experiences would be completely different.

At their core, both start with a unique idea and a small team, naïve and determined enough to believe they can pull it off. The risks are high and many never make it. However, it turns out a surprising number of the fundamentals are the same.

It all starts with an idea. Every startup and every film begins with a spark. For a startup, it’s a problem worth solving. For a film, it’s a story that needs to be told.

At Wellpepper, the spark was helping patients manage care outside the clinic. For This Bloody Country, it was creating a Western from a perspective that hadn’t been seen before: a religious family of mostly women and children defending themselves in 1860s Utah Territory.

You build a founding team. The best early teams have some relevant skills and just enough hubris to believe they can figure out the rest.

For Wellpepper, the founding team was CTO Mike Van Snellenberg and me. Neither of us came from healthcare. We were technologists who believed we could apply product and design thinking to improve patient experiences. That outsider perspective became an advantage when we asked naïve questions, challenged assumptions, and moved faster than people who “knew” how things were supposed to work.

For This Bloody Country, the founding team was writer/director Craig Packard and me. We didn’t have studio backing, but we had a shared creative vision and the stubborn optimism to figure it out as we went. We had an award-winning script, written by Craig. We sought out diverse opinions on the characters, setting, and historical period, and pressure tested how the page would translate to screen by putting ourselves in the eyes of the audience.

In both cases, we started by ideating on how to make the idea real — sketching, testing, and adjusting until we found something that resonated. Then we needed to figure out how to get it done with a business plan that was encapsulated in a pitch deck. Next step was to find people who believed in our shared vision and were willing to invest. While Wellpepper was a C-corp, and the movie an LLC, both were designed as investment vehicles with cap tables.

In startups, you’re promising a future that doesn’t exist yet. In film, you’re selling a story that hasn’t been made. The ability to convey “why this, why now, and why us” determines whether you find your first investors.

You need to be ready to take advantage of luck. Luck is when preparation meets opportunity, and we had early lucky encounters with both projects.

For Wellpepper, we met Dr. Terry Ellis from Boston University when all we had was a prototype. Dr. Ellis, an expert in Parkinson’s disease, was studying how care outside the clinic could help slow the progression of the disease and became one of our first research partners. That collaboration resulted in two randomized controlled trial studies (one also in collaboration with Dr. Jonathan Bean from Harvard), and publications in peer-reviewed journals — powerful validation that our product actually improved outcomes.

For This Bloody Country, our lawyer’s extended family happened to serve on the board of Deer Springs Ranch in Kanab, Utah — which became our primary filming location. The incredible vistas offered million-dollar backdrops to our movie. We also could not have made the film without the help of his extended family: our lawyer’s sister-in-law, an expert in period costumes, was our costume designer, and his brother-in-law served as armorer, art department, and even played a bandit.

Sometimes good timing and luck show up disguised as coincidence. What matters is being ready to recognize opportunity when it knocks.

On the set of This Bloody Country. (Photo courtesy of Anne Weiler)

Beginner’s mind helps you recognize patterns. Many people in both industries told me it couldn’t be done. In healthcare, experts warned that startups couldn’t navigate the complexity of clinical systems. In film, veterans said making an independent feature wasn’t anything like running a startup.

They were right — and wrong. The details are different, but the patterns are the same. Both require solving complex, human problems with limited resources and incomplete information.

Approaching each challenge with a beginner’s mind — curious, open, and unconstrained by “how it’s always been done” — was essential. The key is not assuming you know the answer but recognizing familiar shapes in new contexts: building a vision, assembling a team, creating a project plan, and delivering a product to a customer or audience.

In both startups and films, you must hire quickly, fire carefully, and align people around the mission. You look for collaborators who can thrive in ambiguity, bring specialized expertise, and check their ego at the door. Whether it’s an engineer or a cinematographer, success depends on people who believe in the vision and are willing to do what it takes to get the job done.

The ability to translate experience across domains — without assuming they’re identical — is what made both ventures work. You can’t import the playbook, but you can import the mindset.

Bootstrap before you scale. It’s often said that a CEO needs to wear all hats before they hire them, they won’t be the best at the role, but will lead better when the role is filled by an expert. In a startup or indie film, founder or producer; you’re the marketer, accountant, and sometimes the one hauling gear or answering the tech support hotline.

You learn to do more with less, to make trade-offs, and to keep momentum alive even when there’s no money left in the budget. You’ve got to be okay asking for favors and negotiating. In general, people want to help, and you’d be amazed at what you might get if you ask.

Iteration, testing, and refining. There’s a saying in startups that if you’re not embarrassed by your first product release, you waited too long to ship. The same can be said for getting a rough cut of a film in front of trusted viewers.

For both though, you have to be strong in your vision to explore any feedback that indicates that there may be a problem. In both the startup and the movie if something was confusing to the end-consumer, that was an indication that we needed to iterate and provided the north star for making changes.

From the film This Bloody Country.

Headwinds vs Tailwinds. As Mike Tyson said, “Everyone has a plan until they get punched in the face.” Both paths are defined by risk, and can benefit from, or be challenged by factors outside of your control. Competitors get press or funded, a very similar film or genre succeeds or flops. Regulatory changes offer benefits or drawbacks. Wellpepper was helped by value-based care initiatives which provided tailwinds. The film faced some additional costs due to Covid-regulations while we were screening. You wake up every morning knowing the plan may not survive the day. Being able to pivot and having resilience are key to getting it done.

It’s harder to do it in Seattle. When we started Wellpepper, we were turned down by a lot of VCs because we weren’t in Silicon Valley. There were essentially only 2 VC firms in town. We were told to move. We didn’t, and that probably made it harder, but it also paved the way for many more digital health startups in town. Similarly, it probably would have been easier to get a movie made in LA where the primary industry showbiz, but we found a small, committed group here (shout out to our executive producers and camera department) and quietly made something outside of the system.

What founders and filmmakers can learn from each other

**Don’t index on the outliers. **We’ve all heard the overnight success stories: the film that had a bidding war at a big festival, the startup that came out of nowhere and was aquired by a big tech company. The reality is that most people toil for a long time before you hear of them. That film script might have been on the shelf for years. The startup might have pivoted from something you hadn’t heard of. Build what you believe in for the customer you want to serve, and try not to pay attention to the seemingly quick wins others are getting.

Think about distribution from the beginning. How is your product going to get to the customer? How will they hear about it? Where will they get it? Putting an app in the app store or a video on a streaming platform is really only the first step of distribution. While most film is now digital, there are still distributors that facilitate getting the content to all the places it can be streamed (which often have different format requirements or submission guidelines). While there are outlets such as FilmHub that enable self-distribution, rising above the noise often requires help from a third party, just like software.

**Build a team for the long run. **The team will make or break your project, and while we all like to think success will be quick, you may be working with these folks over a long period. You’re going to be having long nights, and need to pull off miracles with this team. Hire people that you would hire again and again whether that’s for your next creative project, your next startup, or building a team within a big company if you decide to go that route.

**Learn how to tell stories. **Storytelling coupled with passion convinces people. Whether pitching investors or distributors, clarity and emotional resonance are your most powerful tools. When this comes through in your product or your film, it connects with your users and audiences. Start measuring early whether that’s clicks, social media mentions, Kickstarter supporters. Showing that there is a market for your product or for your film requires data. Data is a key part of the storytelling that convinces people.

Be ready for luck. Be prepared (or know when to drop everything to prepare) to take advantages of opportunities when they present themselves. Getting more traction than you expected is a solvable problem. Don’t be afraid to scale.

Creating something out of nothing is an act of optimism. Sticking with it is an act of grit. The data back this up: roughly 90% of startups fail, and about 97% of independent films don’t recoup their investment. Wellpepper was among that small group of startups that achieved a successful exit when it was acquired in 2020, which gave me the confidence to take on the film challenge. This Bloody Country has not finished its journey yet, but it has been picked up by Quiver Distribution, is receiving audience praise, and is available to buy and rent on most streaming platforms.

At the end of the day, both journeys are about creating impact, whether for a patient empowered to manage their own health, or an audience thrilled and moved by a story. And in both worlds, the real victory isn’t just the exit or the box office it’s gathering an incredible group of people to build an idea into something tangible to share with the world.