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“5 Things I Wish Someone Told Me Before I Became the CEO of Expressway Cinema Rentals” With James Madison

Finding good people is hard, but you have to find good people. We have a really strong culture at our company and we care deeply about the people that work here, but that extends to people who suck too. And that has been a steep learning curve. I always want to give people the benefit of […]

Finding good people is hard, but you have to find good people. We have a really strong culture at our company and we care deeply about the people that work here, but that extends to people who suck too. And that has been a steep learning curve. I always want to give people the benefit of the doubt, but that can really hurt you if you are not strict enough with performance expectations. We had a bookkeeper that I really tried to help through his onboarding. I did not feel like what I was asking was too hard for someone with experience to understand, but he continually had problems for months and I continually propped him up in hopes that we could make it work. I started to question whether I was asking too much until one day he really messed things up and I finally had to let him go. It was very difficult, but in taking so long to make that decision, he had really messed things up even worse than I had understood originally and it took a while to come back from that after I let him go. I ended up really distracted and involved n the minutia of his job and then afterward I was really tied up in fixing it. It cost me hours days and months of my life. The point is, you really need great people, especially in key positions and you can’t compromise. If someone isn’t hacking it, let them go and fast and start over before its too late. I have replaced him since and our bookkeeper is amazing and I am free to do my actual job now and grow the company.


I had the pleasure to interview James Madison. James is the co-founder and CEO of Expressway Cinema Rentals: Philadelphia’s leading camera and lighting rental company for the film and video production industry. James is also a recovering film producer, ping pong champion and avid Eagles fan.


Thank you so much for joining us Jason! Can you tell us the story about what brought you to this specific career path?

As a young filmmaker in Philadelphia, my business partners and I did not have the resources or infrastructure that we needed to flourish in this competitive industry. It wasn’t really a young filmmaker problem, but a more systemic and regional issue that affected the city as a whole. But as young filmmakers, we were at an especial disadvantage. As a creative community, we were and sometimes still are presented with a very upsetting ultimatum to compromise our creativity and subscribe to mediocrity or move to a more accommodating market. Expressway was our answer to that ultimatum. We love this community and we do not accept mediocrity. So we took it upon ourselves to build the infrastructure we needed and thus, Expressway Cinema Rentals.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

I should have taken business courses in college. That would be the most glaring challenge. In all things in this world, structure and finance are what make the wheels turn. We all thought we were artists and business was someone else’s business, but that is not true in any industry. Having a healthy understanding of business and entrepreneurialism is so essential to success in this economy. You are dead in the water without it. We were aggressive and brave and bold and that covered for our shortcomings as business operators in the early years, but as we expanded, we went through our share of growing pains. Knowing when to make key hires and being brave enough to spend the money on them was a learning curve. Accounting and QuickBooks was a whole other hurdle.

What are some of the factors that you believe led to your eventual success?

We were aggressive and brave and bold. Even in learning how to run a business, we just dove right in. We had lots of help. Everyone needs help, but you have to be bold enough to go out and seek help. Find help wherever you can and be brave enough to ask the right questions and aggressive enough to implement the answers. I identified peers that I felt comfortable talking to about my problems, they talk to me about theirs and we learn from each other. I joined organizations to help me learn and I took classes. Wherever I could find help. I joined Goldman Sachs 10,000 Small Businesses program and graduated in the 8th cohort. That was a great program that was really validating and I made a ton of relationships that have lasted and continue to be helpful. You have to put yourself out there and seek the help you need.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

  1. Finding good people is hard, but you have to find good people. We have a really strong culture at our company and we care deeply about the people that work here, but that extends to people who suck too. And that has been a steep learning curve. I always want to give people the benefit of the doubt, but that can really hurt you if you are not strict enough with performance expectations. We had a bookkeeper that I really tried to help through his onboarding. I did not feel like what I was asking was too hard for someone with experience to understand, but he continually had problems for months and I continually propped him up in hopes that we could make it work. I started to question whether I was asking too much until one day he really messed things up and I finally had to let him go. It was very difficult, but in taking so long to make that decision, he had really messed things up even worse than I had understood originally and it took a while to come back from that after I let him go. I ended up really distracted and involved n the minutia of his job and then afterward I was really tied up in fixing it. It cost me hours days and months of my life. The point is, you really need great people, especially in key positions and you can’t compromise. If someone isn’t hacking it, let them go and fast and start over before its too late. I have replaced him since and our bookkeeper is amazing and I am free to do my actual job now and grow the company.
  2. Accounting is hard and taxes are unreasonable. That’s a transition from the last segment. Get help early if you need it and make sure it is good help. It took us years to unravel the QuickBooks from our startup years. I self-taught myself QuickBooks and eventually I was able to right ship. But we also found a good accountant and he was instrumental in helping me with that. Once things go sideways in your books, its tough to get it back to square one. There was a lot of fixing. If you are not equipped for bookkeeping, don’t try to do it yourself. Get help and get help early. If you are going to take on the challenge like I did, make sure you educate yourself fast. As a CEO it is important to understand accounting even if you don’t do the bookkeeping yourself. Also, make sure you have a good accountant to check your work. Also, taxes are unreasonable, but get used to it and be ready to deal with it.
  3. Being an Entrepreneur is exciting and rewarding, but it is also terrifying at times and you will find yourself alone. You will need an outlet for your anxieties. I am a creative person from a creative industry and I find a lot of gratification in the work I do as a CEO. I find it to be very creative. There are so many ways to build a company. There is no right or wrong way, only what ends up working and what doesn’t. That is what is so exciting and also terrifying. You get to decide your own destiny and you can make other people’s lives better based on your decisions. The flip side is that people’s lives depend on you, and that is a heavy burden. There are times when that weight can feel debilitating and you will need objective help from people who do not depend on you. I highly recommend regular therapy or at the very least, find peers you trust that do not work with you that you can vent to. Having an outlet is extremely important.
  4. Be really good to your employees, but beware of bonuses. You need good people and when you have them, make sure you are good to them, but be careful of incentive programs. Make sure they are really flushed out and sustainable or they will quickly become a disincentive. It is understandable to want your employees to share in the success of your company. I believe that is a strong motivator for most small business owners, but remember that the long term financial health of the company has to be considered as well. If the company struggles, there will be no bonuses to give out. That can be a sore subject and tough waters to navigate. I advise against traditional bonuses. They will eventually backfire. Instead, make sure your employees feel valued, by being fair and focusing on their long term success and opportunities for growth.
  5. Work-Life Balance is hard, but it really matters if you are truly going to be successful. I have two children and a beautiful wife who do not get nearly enough of my attention. I do not have the answers for Work-Life Balance yet, but you should start thinking about it and build it into your business model early. Me and my business partners are workaholics and that can be unhealthy. It got us to where we are now, but I would have done things a little differently if I knew then what I know now. I am much more balanced than when we started these companies and even compared to a few years ago. It is hard to set boundaries when the expectations and stakes feel so high. It is easy to get baited into long hours when you care so deeply about your business but you have to find a way to strike a balance. It takes a conscious effort. You have to work at it and commit to a schedule that allows you to enjoy the fruits of your labor.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Find a physical outlet. Any sports or exercise you can stick to consistently will be very important for your mental stability. You have to exercise or you will go crazy. Also, see a shrink. There is no shame in it and you probably need it even if you think you don’t.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

There are so many people who have helped along the way, but my wife has been the most supportive and most integral to our success. When we finally decided to make this thing a real business, before we had any track record of success at all, she loaned us our first $10,000 to buy our start-up inventory which really sparked the whole thing. It turned our company into more than an idea, we had products, there were bills, we had debt, there were stakes, it was a business. We weren’t even married at the time. She didn’t have a lot of money, the country was in a recession and I can’t for the life of me remember how we convinced her it was a good idea, but she believed in us for some reason. It was just what we needed to get started. Everything after that just built off that momentum and it all snowballed. Also, she is a Daisy Award winning nurse at Children’s Hospital, which technically makes her the best nurse in the world. It has always been calming and reassuring to know that the greatest nurse in the world is in my corner.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

I want more than anything to live up to the expectations of our employees and of the partnership. We have such a great team and we are working tirelessly to provide them with the opportunities they deserve for upward mobility. Growth has always been a responsibility we take very seriously at Expressway. Our next move will be a big move and we are very excited for what it will mean for our staff. Can’t say much right now, but stay tuned.

Personally, I am still working toward that Work-Life Balance.

What do you hope to leave as your lasting legacy?

When the time comes, I hope to leave Expressway in good hands. Expressway has become a brand that people care about and that cares about the people it serves. It has become the epicenter for video production in Philadelphia and a steward of the community. I hope that we have done a good enough job instilling our culture into our staff and into our operations that Expressway will live on and grow for generations after I have relinquished my CEO position to someone smarter and handsomer than me. That’s a tall order, so we’ll just have to wait and see.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

I think we have done that at Expressway. We have made the industry better, we have built a better infrastructure, we have enhanced the creative capabilities of the region, we have created a more competitive market and we have made people’s lives better. I just hope to build on that progress and I hope that we can continue to expand our influence and our culture in Philadelphia and eventually have a similar impact in some new markets. We have a long way to go still.

How can our readers follow you on social media?

You can look us up on instagram and facebook and you should go to our website www.expresswaycine.com and subscribe to our blog. Our staff regularly publishes amazing articles about industry news and technology that are extremely educational and entertaining.

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