Lessons Learned After 20 Years of Entrepreneurship

Entrepreneurship is an extraordinary journey. The ups, downs, and everything in between often determines where your ventures go and how well they succeed.

In this edition of Venture unscripted., podcast host Josh Barker sits down with longtime entrepreneur and filmmaker John Pottenger to talk about what a 20-year career in entrepreneurship entails and the lessons John has learned along the way.

Listen to the podcast below or keep scrolling to read the podcast recap.

Podcast Recap

Entrepreneur Extraordinaire 

John started his first business 20 years ago and has since launched a couple more businesses. His first? A wedding videography company that he evolved over the years. 

“I fell into it because people were asking me to photograph and film their weddings, but I’m like ‘I don’t do this, I don’t know what you’re talking about,” John explained. He started with a scrappy camera and a very low price point. 

Today, John doesn’t take many snapshots anymore. His company, Coastline Studios, is more in the business of video production. And the company has been called on to capture some of the big weddings in the region — six and seven-figure weddings — as well as smaller, much more intimate events. It’s a broad range and the variety is only possible with the right team. 

“When I was in photography, it was all about me and what I can do,” John explained. But with a team behind him, he could lower the stress of the work and infuse much more fun into the experiences. 

But as John’s business took off and his reach expanded throughout several different networks, he realized that he would need to adjust to some of the pains of growing a business. 

The Growing Pains

John learned a lot with his first business venture and even made some mistakes. And at the end of the day, sometimes unfortunate incidents happen — and as an entrepreneur and business owner, you’ll need to protect yourself. 

At this point, lessons learned for John meant creating contracts. “I can tell you that most contracts out there are probably built from something bad that happened,” John explained. 

But with the right contracts in place, he was able to avoid some of those potential problems. 

However, the growing pains don’t stop there. As companies grow, services expand, and perspective shift — updating pricing comes into play. 

John took a look at what other people in the industry were charging, whether they were on top of their game or totally green. He used that information to determine the starting point and then where he needed to raise his prices. And that’s not always easy. 

John’s advice is to charge what you’re worth and what your experience offers. That doesn’t always happen upfront because it sometimes takes time to build up confidence and resume. But eventually, your work’s worth will speak for itself and your ideal customers will pay the price you set. 

Figuring Out The Right Direction

New business growth isn’t sustainable long term and once your business hits a certain point, you need to assess your goals and figure out the right direction. 

After about three years of working full-time and running a business on the side, John was feeling overwhelmed and needed to reevaluate his goals. After getting laid off from his day job, he had no other option than to turn his side hustle into a sustainable business.

After about six years since the start of Coastline Studios, John decided he needed to cut photography, leaning fully into video production. 

➡️ Listen in to hear John’s take on the Hedgehog Principle and how it can help you figure out what direction to take your business.

But don’t forget, figuring out business direction is almost never a linear process. 

When Things Don’t Work Out…

John admits that not everything has worked out perfectly in his career as an entrepreneur. For example, in 2008, he launched an idea to bring video production to real estate in an innovative way. Then the Housing Crisis of 2008 happened and real estate took a major nosedive. John’s venture never really took off as planned. It was a great idea, but the wrong time. 

But how did he know when to call it quits? Despite people loving his idea, they couldn’t afford it. With this in mind, he was able to shift gears. John was able to look at his opportunities through a slightly different lens. 

After 10 years in the game, he received more and more video requests for corporate commercial work, which didn’t fit into the wedding genre of his business. It wasn’t John’s niche, but he tried it out, even when he didn’t have the staff to do so.

Some people might consider that a setback. But John saw an opportunity to start another company — Match Frame Creative. It started through a partnership with a friend and it’s been thriving with projects from Steelcase, Amway, and other large corporations. But despite the success, John says that entering into a partnership is one the best ideas someone can have, but also one of the hardest things someone can do.

“Partnerships are good if you find the right partner because then you’re not alone,” John explained. “You don’t have to have the pressure of making your own decisions. If something bad happens, you’re not shouldering it all yourself. If you get stuck, you can work it out together.”

But we’re human and we are far from perfect. You have to enter into partnerships cognizant of your selfishness and John says you have to be completely self-aware. If you’re not — the worst of people will come to the forefront. 

“I always say to people who are thinking about being in a partnership, just know, you’re basically getting married. You’re going to need to find a way to communicate. You’re going to have some fights. If you’re not willing to work on yourself as a partner, it’s not going to work. You have to have humility and be willing to admit you’re wrong.”

Finding the Right Partners

John found his first business partner through his network. They worked together on an alumni film board for a film school and even worked on some freelance projects together. It was clear to John that they had strengths that complement each other well. Plus, they both had a sense of integrity between them that made it easy to embrace their differences. 

But the most important aspect of finding the right partner is trust. “Our specific value systems are similar and we know that we could trust each other.”

Finding the right partner also means finding the right companies to help push the envelope as well. More recently, John has been able to invest money into other opportunities and explore a very different venture — an app for doctors called Sanotrek. The app allows doctors to keep their patients engaged throughout their healing journey. Building on this new idea and creating this app has been a three-year process for John, and he needed the right partner to see it through (that’s us). 

Unlike the normal path that we advise, John didn’t start with market validation or experimentation. He already had a tangible app in hand when he started working with City Innovations. However, he is still in a position to test and reassess to better understand who his app is for and how to best target that audience. 

Lessons Learned

John has learned a lot through his 20-year career as an entrepreneur. From John’s perspective, the most important thing you can do as an entrepreneur is validate your idea. Don’t spend a ton of money — find out first if your idea has any legs to it. Figure out if your idea is worth moving forward, pivoting, or quitting entirely. But keep going and persevere. 

Always reevaluate what you have to see where you can capitalize on what’s working and what could be even better. For example, John opened up his company’s studio space to other start-ups and organizations in need of a physical space to create content. He already had the space and now he’s putting it to use in more ways than one. 

And when it comes to new ideas — John says don’t be afraid to scratch that itch. Most entrepreneurs have the urge to constantly start new things or coach people and help them start new things. 

➡️ Click here to listen in for a recap from John on some of the innovative new ventures he’s involved in. 

And after 20 years, John states three things that everyone should consider before embarking on the journey of entrepreneurship. Number one: Hire the right people. Getting the right people on your team is crucial, whether they’re partners, team members, or even employees. Number two is to learn from your mistakes and know where you can protect yourself. And finally, number three would be to remember that the short-term pain will often pay off with long-term gains.

Continue Learning

Listen to the full story and gain even more advice for entrepreneurs by checking out to the podcast video below. 

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