Reflections of a Former Child Entrepreneur
Ten Business Lessons That I Still Carry With Me
My first foray into entrepreneurship came at the age of 11. With some sort of innate drive to want to solve business problems while also making money, I transformed my trading card and collectibles hobby into an actual business while I was still in elementary school. Nurtured by a mother who was a home-based publicist for small businesses, I caught a bug that has lasted for a lifetime. Over a decade that stretched into my junior year of college, I grew Ron’s Cards & Memorabilia from a sports card and political button retail business into the New England Non-Sport Co., which specialized in vintage (i.e. older than I was) non-sport trading cards. I bought and sold cards myself at regional sports card and collectible shows that were held at hotels and convention centers, as well as through magazine advertising-based mail order (pre-eBay). I would ultimately organize the first-ever show held in New England bringing together buyers and sellers of exclusively non-sport collector cards. That show was successful enough that I grew it into a two-day event that I ran annually over six years.
Although this time of my life seems like ancient history now, I did learn many early business and entrepreneurial lessons that have stuck with me until today. Here are ten highlights:
Follow your passion and “you’ll never work a day in your life” as they say… I got into trading cards simply because I wanted to and I had a lot of fun with it. One gets into a state of “flow” (losing track of all time) when you’re doing something that you passionately enjoy. As a pre-teen and teenager, for me it was all about buying and selling vintage trading cards. I would read all of the relevant publications (Beckett, Sports Collectors Digest, Non-Sport Update, etc) cover to cover because I had a hunger to know what was happening in the business. Without that level of self-driven commitment, there will always be someone else out there who is willing to work harder and be better at this than you will be. If you dedicate yourself to doing something, you’d better do it to the best of your ability and that will only happen if you truly love what you are doing.
Opportunity recognition and adaptation. If you’re going to start a business, make sure you are clear about what problem or need you are solving for. If it turns out that the initial strategy is difficult to execute or to expand, stay alert to how you might pivot that business into something that is tangential but where a bigger gap exists that a clever entrepreneur can seize upon. For me, this meant shifting from a focus on baseball and other sports trading into non-sports trading cards. While a narrower niche, non-sports cards gave me a leg up in that there was less competition, but still a sufficiently large and growing market of potential customers. I quickly realized that I could become a bigger fish in a smaller pond by having this focus. It helped too that I personally found that diversity of subject matters covered by non-sports cards to be more fascinating than just sticking within the realm of essentially four major sports (baseball, basketball, football, and hockey).
Trusting your instincts when trying something new. Entrepreneurship is all about trying things that are innovative or simply haven’t been done before. Otherwise, it’s simply “small business ownership” which is not quite the same thing as being a true entrepreneur. For someone who likes to experiment, tinker, and of course take measured (or sometimes, not so measured) risks, there is no better path than being an entrepreneur who controls one’s own destiny. One has to accept some level of risk if you don’t want to be constantly second guessing yourself. It’s fine to be insecure about decision-making. That is natural and human. However, sometimes entrepreneurs need to throw caution to the wind and simply trust their instincts and go for it. I did this when I decided to organize the first dedicated non-sport trading card show ever to be held in New England. From having seen events like this work in New Jersey, Pennsylvania, and Illinois, I had a suspicion that it would work in the Greater Boston area too. So I rented out a function room at the Marriott Hotel in Newton, Massachusetts (my hometown), not knowing what to expect. When I opened the door at 9am to let collectors come into the hall, I found a line of people snaking all the way to the main hotel lobby, and it was then that I knew my instincts had been right. I made a bit of money that day, but more importantly, it gave me the confidence boost that I needed to feel like entrepreneurship was something that I should continue to lean into.
Having the chutzpah to build a personal brand. Developing a competitive edge takes effort. To stand out in any industry requires developing a brand for yourself and your company. By becoming an authority in a subject matter, one can find resources and tap into opportunities that might not otherwise be transparent. In the collectibles business, this means that people think of you first when they are buying or selling. For me to do this as a younger teenage entrepreneur, I had to hustle and think creatively. One way that I did this was through the non-sport trading card shows that I organized in the Boston area. However, to build a name nationally and open more doors for myself, I decided to take a shot at writing articles about non-sport cards for one of the national trade magazines, the now long defunct Card Collector’s Price Guide (“CCPG”). In the pre-digital age, print publications were the lifeblood of the industry and was how enthusiasts found one another. Despite only being a high school freshman, I reached out to the editors of CCPG and asked if I could submit a written article for publication. Seeing nothing to lose, they said yes and accepted my first piece. They offered to continue paying me 10 cents a word to submit articles monthly (and sometimes even more frequently). Some of my articles even appeared as the magazine’s cover story for a particular month. In pre-web search days, all of the research and writing was my own, but I worked hard to research my subjects and write something that I thought would be interesting for readers. I kept doing this for a few years until I finally had a chance to meet the editors in person at a large card convention. Imagine their surprise when they discovered how old I was. My age was not something that had ever come up and they had no idea they’d been dealing with “a kid” all this time. Sometimes you just need a little chutzpah (one of my favorite Yiddish words) to go out and make things happen.
A relentless focus on the customer. I learned a lot about dealing with customers at such a tender age. If I can boil it down to one phrase, it would be “The customer is NOT always right, but they should at least get the benefit of the doubt.” It is helpful to have empathy for one’s customer. Treat them respectfully, although realize that in a business that involves haggling, the seller too needs to know what is negotiable and where the limits are. There were definitely some unscrupulous individuals in the trading card hobby of my day, but most dealers and collectors were kind, fair, and motivated by the same passions as everyone else. Trying to put myself in the shoes of my customers generally was a principle that served me well.
Understand the challenges of scaling. It didn’t take me too long to understand the difference between a "lifestyle" business and a “scalable” one. Most businesses have challenges that eventually limit pathways to growth, but mine was especially the case. I simply didn’t have the margins to expand into selling more valuable products, hiring a team, opening physical retail locations, or organizing shows across more collector verticals or geographies. That’s fine. Many business owners don’t have the ambition to hyperscale nor should they. Sometimes local, small, and “niche” are perfectly appropriate business models. They can pay the bills and come with a lot less stress or risks than trying to create a Fortune 500 empire. Even by the time eBay came along to demonstrate how a collectibles trading platform could scale and become extremely valuable, there were also many others who tried and failed to generate such results. Sometimes the best moat is a well-run sole proprietorship or family-owned business with a strong reputation based on the strength of personal relationships. To build a large, scalable empire requires a very different mindset and resources.
Select the right business partners. I made several attempts during my card business side hustle to work with business partners (i.e. co-owners/managers). I ran shows with friends. I started an association and a trade newsletter with a relative who shared my industry interests. None of these worked out particularly well. While sometimes it may seem that bringing on a business partner would result in only having to do half the work or have half the responsibility, the truth is that partnerships can be a double edged sword for any type of business. Personalities can conflict and interests can become misaligned due to issues in style, strategy, ambition, communication, or any number of unforeseen circumstances. I became much more cautious over the years about how to think about partners, co-founders, and collaborators. This is not at all to say one shouldn’t partner with likeminded, talented friends. However, one should enter a business partnership only after careful consideration about how each partner’s skills, responsibilities, and goals will align with the other’s. Think of it as entering a marriage, because it’s very likely the one could actually be spending more hours of the day with a business partner than with a life partner. Just because two or three people make for good friends does not mean that they will be complementary or synergistic collaborators in running an organization.
It takes a village. Legendary bodybuilder-turned-Hollywood megastar-turned Governor Arnold Schwarzenegger likes to say that it’s ok to call him by many different names, but one thing he does not take well to is being called a “self-made man.” Even those who are the very best at what they do reach that point only thanks to the support, tools, and good fortune that they have enjoyed in life. Obviously hard work, intelligence, and resourcefulness make it easier to find luck, good fortune, and serendipity. However, all of this is enabled by other people who nurture the creativity and innate savvy that successful entrepreneurs and leaders often possess. In my case, my parents played the biggest role by not just allowing me to go off and spend time on my business as a teenager when I probably should have been studying or doing more traditional after school activities. They went out of their way to schlep me in their car within them to trading card shows all around New England and beyond, consuming countless hours of their own lives. I also benefited from the support of friends and mentors within the trading card hobby who encouraged me to keep building, as well as some progressive teachers and other adults in my life who felt what I was doing was unique and even educational and worth nurturing.
Tradeoffs and time management. Even small “side hustle” businesses take time and time is one thing that can’t be manufactured. So lessons in time management become critical. What sort of tradeoffs is one willing to make when stepping into running a business. If it’s driven by passion, it is easy for an entrepreneur to get into that state of “flow” that I noted earlier, where time passes in the blink of an eye. Does time spent on a business mean less time spent on school work or a day job? Is it less time with family and friends? Does it mean sacrificing other projects, hobbies, and interests? Or perhaps sleep, exercise, or simply downtime? These are all considerations one must think about. For me, in hindsight, as a high school student, I gave up some elements of social life, club activities, and probably a little bit too much of my academic work. I recognize that I did not achieve to the level of my capabilities, because I simply leaned into spending time on my business while neglecting the subjects at school that I found less exciting. I recall that a local journalist once wrote an article about me and my budding small business. She asked me if I was an honor roll student, and I had to simply reply candidly that I was not. Slightly embarrassing, but truthful. It took me well into my college career before academics really started becoming a priority for me. I had to play catch up and managed to graduate Babson “cum laude” by the skin of my teeth. Now, it is well known that academic achievement does not necessarily directly correlate with entrepreneurial or other kinds of success. This has proven particularly true for those with certain types of neurodivergence such as autism, ADHD, and dyslexia. However, thinking hard about tradeoffs in life and understanding that leaning into one area could result in sacrificing another is critical for being honest about one’s goals and the personal risks that are entailed in achieving them.
Developing a pathway toward the future. My final reflection as I look back three decades since my active days as a collectibles wheeler dealer is that this all laid the groundwork for a future that I could not have clearly predicted. These early experiences certainly reinforced to myself that I was a business-oriented person who believed strongly in entrepreneurship as a force for both wealth generation and as a vehicle for positive societal change. I knew I was a capitalist and would spend at least the bulk of my career pursuing profit. However, I couldn’t really wager a guess as to what industry I would be in and what the ultimate “dream” would be. I thought perhaps I would be the CEO of an airline, or a manager of a mutual fund, or even a serial entrepreneur who hopped from creating one successful business after another. In any case, I feel the most important lesson is to keep an open mind while pursuing personal passions that could turn into successful professional pathways. There is so much luck and serendipity in life, as well as unexpected challenges and setbacks. By staying focused on aligning life goals with personal interests in setting into a career, one is already positioned to succeed. Reflecting on how that past can inform the future is something we all ought to be doing from time to time to make sure we are finding fulfillment in our daily lives and keeping the right aspirations for the future.
I remember well those early days of your trading card business. I was in law school in Boston and when your mother would invite me for Shabbat dinner, you would be preparing for a show. I loved that you had your own business cards!
Your insights into entrepreneurship are spot on! They track closely with Brad’s experiences in a very different area, speaking to the validity of what you identify as being universal to entrepreneurs.