Jason Foodman

Jason Foodman is an Entrepreneur and CEO with experience operating companies globally. A frequent Board member and advisor, Mr. Foodman also is a writer, author, and member of the Forbes Business Council. He has been a leading participant in the software and payment industries for decades, founding one of the early software e-commerce systems, RegSoft.com. Later, Foodman introduced the notion of a “Backup CD” for software e-commerce via SwiftCD.com, a company he founded. SwiftCD was ultimately sold to Digital River, and Foodman started FastSpring, which became a leader in the software e-commerce space. Following the sale of FastSpring to Pylon Capital (and then Accel KKR), Foodman was President of Global Delight and interim-CEO of PayPro Global. In October 2020, Foodman assumed the role of President at Rosy Salon Software, a Fullsteam.com portfolio company. Mr. Foodman’s most recent Board experience was as Chairman of the Supervisory Board at asknet AG, a German-based payments company specializing in ESD and Academics.

Since 2010, Jason has been a Merchant Marine, holding a 100-ton Master Captain’s license from the United States Coast Guard and a U.S. Coast Guard Auxiliary member.

What is your typical day, and how do you make it productive?

I try not to have a typical day because I would be sitting on calls all day long. Instead, when possible, I schedule my days to have a relaxed start and spend quiet time reading and responding to news, emails, and notifications that came in overnight (before getting into a meeting cycle). I do it this way to ensure I remain responsive and on top of things. I usually have numerous video calls throughout the day, but those are interspersed with scheduled gaps, so I can continue to respond to incoming requests relatively quickly. Lunch is a priority for me, even if it’s quick a few minutes ‘away from keyboard’ help me clear my mind. Generally speaking, I never miss a meal (my last name is fitting in that regard). In the evenings, I typically spend a few hours tying up loose ends from the day that I couldn’t get to. This kind of schedule is not for everyone, obviously. I’m admittedly a bit of a workaholic, but when you enjoy what you do, it really doesn’t really feel that way. My style is to operate in a fairly relaxed way, minimizing stress and chaos, even though it means using some evening and weekend hours.

How do you bring ideas to life?

My challenge has never been a lack of ideas or bringing them to life; the harder part is figuring out which ones are good and which are terrible (and likely to fail). For me, bringing an idea to life normally starts by identifying and convincing others to join me, specifically those who can bring key success ingredients to the new business. If I were to plot the companies I’ve started, for the most part, the more partners I’ve had the more ultimate success the business has achieved. So a key aspect of bringing ideas to life, for me anyway, is finding people I trust who believe in the idea and have complementary skills – and convincing them to join me on the adventure.

What’s one trend that excites you?

I hate to say AI because it seems like everyone is talking about it, but there are some good reasons why. My Master’s Thesis (in Computer Science) at UNC Charlotte was focused on genetic and evolutionary programming, an approach within the overall concept of machine learning. So naturally, I’ve been excited to follow the evolution of AI and the new ideas and capabilities around it. Looking forward, I believe that many of the things we do today, online and also offline, how we do them and how we experience and process information in general, will be heavily impacted by AI over the next decade. When you think about information, how it is computed and used, and what it drives, the possibilities are endless. That said, I also have concerns about where all this is going, some of which I outlined in a recent article on Forbes titled Artificial Intelligence Is Changing The World And Your Business.

What is one habit that helps you be productive?

In a word, organization. I methodically organize all of my files in folders, and I manage all of my emails in a similar fashion. I’m also hyper-disciplined with my calendar, maintaining an organized calendar is essential for my productivity. I use Slack and other tools to store business discussions and enable fast and efficient communication with partners. My passwords are all organized into folders in a password keeper, and I keep meticulous notes about crucial conversations. This level of organization, in turn, helps me be much more proactive and efficient because I can quickly find, review, and use material, emails, and information with minimal effort.

What advice would you give your younger self?

It’s easy to say, ‘If I knew then what I know now,’ but life unfortunately doesn’t work that way, and (so far) there’s no going back. As a result, I try to learn from the past but stay very focused on the future. That said, when I reflect back and think about what matters in life, the reality for me is that it’s people. So my advice to my younger self would be to spend more time with your grandparents; you may not understand them or feel that you relate to them at a young age, but take the time to – they won’t be around forever.

Tell us something you believe almost nobody agrees with you.

Banana pudding. It’s so delicious and has bananas in it, so it must be healthy.

What is the one thing you repeatedly do and recommend everyone else do?

Laugh. I really believe laughter is tremendously beneficial for your health and relationships but also in business. I often start a meeting with an attempt to get everyone laughing, especially when it’s meeting with people for the first time. Laughter and joy are tremendous tools for dissolving tension, creating positive energy, and increasing productivity.

When you feel overwhelmed or unfocused, what do you do?

If I’m truly overwhelmed, which thankfully doesn’t happen often, I try to step back from the big problem or challenge and go into problem-solving mode. I pick one issue or task and focus on just that problem. Once accomplished, I shift to the next problem again with complete focus. On the one hand, it’s good to understand the big picture and goal, but if in the moment it’s overwhelming, rather than accomplish nothing I break the problem down into smaller problems and focus individually on those.

What is one strategy that has helped you grow your business or advance in your career?

Maya Angelou said, ‘At the end of the day, people won’t remember what you said or did; they will remember how you made them feel.’ I feel like this is so true, so spot on, that it’s essentially a strategy for growth (personal and professional). When I’m interacting with employees, customers, vendors, partners, or really anyone, I think about how I am making them feel with my words and actions. It’s human nature; people like being around and doing business with people they trust, who make them feel confident, happy, safe, appreciated, and valued. Although I can’t claim to be perfect at it, I think that by trying to be a mensch and making people feel happy and valued, my business and career have benefited significantly.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

Back when software came in boxes in retail stores, I had the idea of creating low-cost, low-quantity, highly professional boxes (because, at that time, for most, creating boxes meant a big investment and ran in the thousands). I spent a year developing proprietary processes, working with an offset printer and creating a website and materials. Once ready, the launch was at a software industry trade show, with a fully staffed booth and tiny software boxes filled with mints as a giveaway. It was absolute crickets; the level of interest was somewhere between zero and less than zero. After investing more than a year into the project, I remember sitting on the plane ride home and thinking carefully as to whether there was a viable pivot. I got home and immediately killed the business.

Frequently, I have seen entrepreneurs clinging to something that is so very clearly a failure, but they have become emotionally invested in it and are simply unable to walk away. I learned two lessons from my box business failure. The first lesson was that no matter how confident I am about a new idea, some amount of research and validation is a good idea. The second lesson was sometimes, unfortunately, you have to throw in the towel. It happens to everyone, especially serial entrepreneurs, so pick yourself up and try again with even more passion the next time.

What is one business idea you’re willing to give away to our readers?

If you look at the history of major social sites and search engines on the internet, all those sites and brands that today we look at and view as unstoppable forces basically replaced similar unstoppable forces twenty or so years ago. They may totally dominate their space today, but it’s quite likely one or more of them will be replaced by new solutions that start from scratch. Without naming names, I’m thinking about online retail, search engines, social sites, payment solutions, etc. For example, I believe there is room for an entirely new type of search experience that melds various forms of media and information together in a very different way than how it works today. In my opinion, the engines today have become very good at analysis and comprehension, but they are still lacking in terms of how they present a summary of information about a query. I have long imagined a new type of experience, a much more media-rich, diverse collection of information stitched and presented together. A future version of the encyclopedia of old, not just a list of URLS or images or News. I can sketch out what I have in mind, but hey, your reader has to do some of the work here!

What is one piece of software that helps you be productive? How do you use it?

I rely very heavily on four pieces of software: Thunderbird, Slack, Dropbox, and Zoom. I’m unsure I could narrow it down to one, as each is essential to my productivity. For the purposes of this article I’ll focus on Thunderbird. Mozilla Thunderbird, originally called Minotaur, is a free and open-source cross-platform email client. I started using it in 2003 on Windows 95, long before it even hit version 1.0. At that time I imported email from 1997 into it. Fast forward twenty years and it has grown into a very robust email, news, RSS and chat client. I love it because I know every nuance and I have every email since 1997 in there, all organized and quickly searchable. In general I try to use the best technology available to solve any given problem, without bias of platform, history, popularity, etc. When it comes to email, for me that’s Thunderbird.

What is the best $100 you recently spent?

Taking my wife Julia and our kids out for a nice dinner. I work hard so that I can enjoy time with the people I love. Plus, I also love food. So it’s a win-win.

Do you have a favorite book or podcast from which you’ve received much value?

The world has gotten more and more complex in the last five years. In the past, I was so busy and not so interested as to try and understand geopolitics at any depth. In 2019, I started listening to Peter Zeihan, a well-known geo-political expert. Peter produces content nearly every day, I consume it primarily on Youtube. Most mornings I begin with my black tea, a light breakfast and Peter’s daily video. His fifty-thousand-foot analysis has given me a much better understanding of what is happening in the world, where, why, and what it likely means for everyone’s future.

What’s a movie or series you recently enjoyed and why?

My wife and I have very much enjoyed watching Only Murders in the Building. It’s quirky, funny, and at times serious. Each season centers around a murder mystery, as the show has an overall detective theme. On a recent trip to New York, we even took the time to visit the building near Central Park used for the external shots. Pro tip: they don’t let you into the building unless you live there!

Key learnings:

• In business, don’t give up unless it’s truly time to give up, in which case, do so quickly.
• Being an entrepreneur requires hard work, dedication, and passion – there’s no short cut. But don’t forget to also enjoy life; you only get to do live it once.
• Take the time to get organized. You’ll save much more time than you spend doing so.
• In business, try some big swings; they don’t always connect, but every so often, one does.
• Surround yourself with amazing people, and you are far more likely to do amazing things.