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“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Adam Boeselager founder of Legacybox

As an entrepreneur, the breadth of experiences and skill sets that I’ve had to learn quickly far surpass anything I experienced in a traditional 9–5 job. I was forced to wear a lot of different hats and balance all aspects of a business — from learning, managing and scaling Facebook advertising campaigns, and re-configuring production plants and […]


As an entrepreneur, the breadth of experiences and skill sets that I’ve had to learn quickly far surpass anything I experienced in a traditional 9–5 job. I was forced to wear a lot of different hats and balance all aspects of a business — from learning, managing and scaling Facebook advertising campaigns, and re-configuring production plants and workflow, to ensuring our finances were GAAP compliant. You also have to learn to make the hard calls. It’s all strategic and it’s all on you. The cost of mistakes meant failure and since there’s really no safety net you learn quickly to become a fantastic decision maker because the stakes are just so high.


As part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Adam Boeselager. Adam is an entrepreneur, investor and founder. In high school, when most of Adam’s peers were buying cars, Adam was saving his money and pitching his parents for a business micro-loan. Then armed with a website and a toll-free number that forwarded to his cell phone, Adam’s first company was born. In college, Adam founded Legacybox, a direct-to-consumer e-commerce company, in his garage. The company would lay the foundation for what is now the world’s largest digitizer of home movies and photos. Legacybox has 600,000 customers, has digitized 3-million videos and serves customers all over the country. The company has 150 employees, two Tennessee based offices, and a 52,000-square foot production facility. In his fleeting free time, Adam enjoys boating on the Tennessee River, traveling to exotic locations, reading business gurus’ biographies and consuming large quantities of good coffee. Adam lives in Chattanooga with his lovely wife and their daughter.


Thank you so much for joining us Adam! What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

The first “ah ha” moment was after I saw the first online order confirmation email in my inbox. I remember that customer like it was yesterday, from New York City. This was in the early days of e-commerce, and I was fascinated by the fact that a complete stranger, hundreds of miles away who I had never met, just purchased the service that I was offering. They simply trusted a website that I spent several weekends building and I was so inspired that I wanted more of that feeling.

There is no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I don’t think I’ve ever been much of an ‘idea’ guy. I love thinking, dreaming, considering the ‘what-ifs’, but there was always this voice inside my head that would say talk is cheap. I always felt that if the idea someone was pitching truly was amazing and world changing, why were we still talking about it and not doing it? I wanted to be a doer. I wanted to prove that my ideas had merit and would work, and the best proving ground was the real world. So that’s what I did. I sought the approval of customers from day one, and they voted by choosing to buy what we were selling. I never saw it as a challenge, but just understood that was the way the world worked. Otherwise, I wouldn’t have an actual business.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

When you truly love the hobby or pastime you’re doing, you ask yourself why you would ever want that to change? I read The E-Myth Revisited by Michael Gerber early in college, and it left a lasting impression on me. I realized that making the leap from turning a pastime into a living meant that I would have to start wearing multiple hats and that I’d have to challenge myself to learn all the roles required to run my business. You can’t stay in the role that started as only a hobby.

My advice for someone considering taking the leap would be to do some serious soul searching: are you ready to expand your responsibilities beyond what you love to do to create a revenue model, understand accounting, navigate legal situations and so much more? Are you ready to learn how to manage your business? The risk you’re taking is that if you do well, you probably won’t do as much what you currently love because you’ll have to take on new roles and responsibilities, but the reward might be that you’ll find fulfillment in new places and discover that you’re much more capable than you ever thought.

How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

In the early days of our business, we were intentionally selfish in the rare moments that we could be. For years we did everything that was required of us, and more, but when we had the opportunity to delegate, we passed off the tasks we had mastered on to other team members. Of course, we held on to some tasks that we didn’t always enjoy because we knew they were critical to growth and later we had to hand off even the things we did enjoy because the growth of our company required that we learn more in different areas. My business partner had to stop doing graphic design and I had to step back from aspects of our production plant so that other talented members of our team could lead those areas and we could focus on what was next. We keep it enjoyable by pushing ourselves to be ready and open for the next challenge.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Entrepreneurs get to make their own ideas and dreams a reality, while 9–5 jobs often feel siloed. Being an entrepreneur makes you feel like your influence is so much broader and more impactful. The biggest perk though: experiencing the reward of seeing your dream become reality. It’s addictive to have an idea and then see it be executed quickly and efficiently. Seeing it fail is hard, but you learn to channel it into a driver for the next winning idea.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

As an entrepreneur, the breadth of experiences and skill sets that I’ve had to learn quickly far surpass anything I experienced in a traditional 9–5 job. I was forced to wear a lot of different hats and balance all aspects of a business — from learning, managing and scaling Facebook advertising campaigns, and re-configuring production plants and workflow, to ensuring our finances were GAAP compliant. You also have to learn to make the hard calls. It’s all strategic and it’s all on you. The cost of mistakes meant failure and since there’s really no safety net you learn quickly to become a fantastic decision maker because the stakes are just so high.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Being an entrepreneur is willingly signing up for an emotional roller coaster ride. One day you feel like you’re conquering the world and the very next morning you feel like you’re putting out fires. I’ve learned that in order not to burn out emotionally, you have to take a step back and celebrate the day-to-day wins, tackle the crisis of the moment, but remember to look at that within the context of how we are doing this quarter, or this year. Perspective will bring sanity. I think I’ve always enjoyed being an entrepreneur, so there was never a fall back plan. I never considered getting a real job. I was going to go down with the ship per se, and if that happened, I’d pick myself up and begin again.

Can you share the most interesting story that happened to you since you began leading your company?

When we started off we were small. At first it was me and then it was me and my business partner. It took years for us to make our first million in revenue and then things really started to take off. But in those early years, we’d introduce ourselves and explain what we do and maybe we’d get a nod or a confused look. People were certainly skeptical so we had to explain what we were doing or try to convince them of the validity of our business. After a while we stopped explaining and had to rest on our own confidence in our business model and plan. Now, in a complete reversal, when we walk into meeting we meet people that have seen our ads on Facebook or have used Legacybox themselves. It’s crazy how big our reach has expanded and how our brand recognition has grown.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In the early days, myself and my co-founder Nick would take every call from customers. It was a way to keep a good pulse on what customers were thinking, what tweaks to the service or website were required and frankly we didn’t want to pay someone take calls. Customers kept asking us what these DVD duplicates were that we were selling and we’d have to explain that they were copies of their own DVDs that they could make for family and friends. After answering this question probably fifty times we changed the website copy to reflect the language our customers were using, not the technical industry terms. It totally worked! Sales quadrupled on that product and customers stopped calling with that question. We’ve learned from that lesson and regularly use customers as inspiration for copy and branding touch-points.

How have you used your success to make the world a better place?

It’s an honor that so many families have trusted us to digitize their important family memories. As a team we’re privileged to do such meaningful work every day and I am confident that we’re making the world a better place, one customer at a time. We’ve digitized tens of millions of videotapes and photos for customers and reading the reviews and getting feedback is so meaningful for myself and everyone at Legacybox. We’re really just getting started.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Marketing is key. Life is so much easier when you have sales rolling in. It creates new problem of course, but it opens the door to so many other options.
  2. Don’t go it alone. It can be lonely at the top. There’s so much pressure and anxiety and it can be hard to manage. For me, that meant going on the journey with a co-founder and even the two of us weren’t enough. We spent several years trying to find the right advisers and when we finally did, it was a big breakthrough.
  3. Revenue is the lifeblood of a company. I wish I would have focused on that earlier on. Revenue isn’t won by hustling 80 hours a week and though that might be required. Often I’ve found our biggest wins have come from maximizing a small opportunity or finding the one detail that really makes something work. You must guard against burn out and give yourself space to think so you can be ready for that one moment where you have a chance to secure a partnership or nail down a marketing strategy.
  4. Be patient and give it time. Success doesn’t come overnight. It’s built from a series of small, right decisions and the key is to stack one hundred of these great decisions together.
  5. Get ready to wear multiple hats. Being in business means that all responsibility is now on you. From trash to taxes and finance to benefits. You get the burden of creating and managing it all. Which is amazing, but a tall task. Just know what you’re signing up for.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I’m a super fan of entrepreneurship, especially at the small business level. I think so much good work comes from people sticking their necks out, taking risks and asking their fellow consumers: will you buy this good or service that I’m providing? And when they say yes, that’s the magical moment. The free exchange, the place where two people in the world agree that they are better off trading their resources or goods with each other. Those repeat themselves day after day, and that collaboration, those intersection points, those incentivized alignment of resources make everyone better. I’d want to inspire more and more small businesses, more entrepreneurs, and more local commerce to take a chance on themselves.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Benjamin Franklin is quoted saying, “Don’t put off until tomorrow what you can do today.” I’ve adapted that and often say that in our company days are weeks, weeks are months, and months are years because we’re growing and changing so rapidly. When someone says they can do something next week, I always recoil a bit because in my mind I’m hearing that they’ll do it in a month. I think when the task at hand is clear, there’s no point in waiting. You get so much done so much faster just by being a person of action.

Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why?

I’d want to sit down with someone who is a visionary and dreamer. In college that would have been Steve Jobs, but I think the person that has picked up his torch and has intrigued the world with his vision of the future now is Elon Musk. I love that he leads the dialogue about innovation and he truly has captured our imaginations.


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