Q&A With Jack Gordon

Starting up and running company is hard enough. But for Jack Gordon, that’s just a starting point. Jack is mostly known for running WebRecon, a litigious debtor scrub that has become an important risk management product for companies in the accounts receivable and contact center industries. But Jack also runs FDCPA Certifications, a training and knowledge management service, Cheaper Booths, a tradeshow design service, and more. Harnessing the entrepreneurial spirit and developing a spidey sense for good ideas is a skill Jack has honed over his years in the business. Read on to learn more about how Jack comes up with his ideas, and what to do when those fleeting flashes of brilliance appear.

Mike Gibb: You seem to be consistently rolling out new products and companies. Have you always been so entrepreneurial?

Jack Gordon: No! I spent my teen years working a series of odd jobs (first job was at a comic book store when I was 11), then a summer job at college turned into a 12 year corporate stint. I never even thought of being entrepreneurial in any kind of a serious way until my early thirties.

Mike Gibb: Now that you’ve started, you can’t seem to stop. From where do you get your ideas?

Jack Gordon: Honestly, it’s a skill that I don’t know how to turn off. I just keep my eyes open to the world around me and when a problem becomes apparent that I think I can solve, it nags at me. If it is a powerful enough idea, I can’t shake it. That’s when I know I have to follow it.

WebRecon was like that. FDCPA Certifications was too. Our newest launch is an online training platform that solves a lot of the problems we’ve run into over the years running the compliance course at FDCPA Certifications. We needed something that better addressed our needs than what was out there, so we built it.

Mike Gibb: That seems very subjective. Do you think that’s how most successful businesses are started? More art than science?

Jack Gordon: I’ll admit that I am pretty ADHD. I probably follow my gut more than I should, and it has not always led me to success. But as long as I am winning more than I am losing, I’m pretty happy with that.

I don’t think my process is right for everybody, but I also know that there are an awful lot of people who are just like me. I see them all over the entrepreneurial groups on social media.

Mike Gibb: Do you think the ARM industry is one that embraces entrepreneurs? We don’t see a lot of new start-ups normally.

Jack Gordon: I think the regulatory environment around the collection industry certainly discourages entrepreneurial innovation. But that is a challenge to be embraced by strong people with good ideas. Nothing about entrepreneurship is easy. I think many of your readers understand that viscerally. When I started WebRecon out of my basement 13 years ago, nobody was asking me about network security or PII controls or policies and procedures. Of course today everything is different. We expend an inordinate amount of resources to satisfy today’s requirements. I may have been among the last of the entrepreneurs in this industry to get away with bootstrapping a company that utilizes sensitive consumer data.

Mike Gibb: If entrepreneurial spirit is a challenge to be embraced, how do you recommend developing a set of eyes through which opportunities can be spotted?

Jack Gordon: I have actually thought quite a bit about this. To put it into near-universally understandable comic book terms, I think of it as developing a “spider sense”. When Spiderman senses danger, his whole body reacts, telling him something is about to happen. Now substitute danger for opportunity. When I see a problem, my first instinct isn’t to complain about the situation, it is to think of how it can be improved. Quickly followed by wondering if I am a good choice to be the one to offer a solution. And if those two parts come together, it takes over in me. Once I started looking at the world around me that way, it was a bit of a revelation. This is what I was referring to earlier when I said I can’t turn it off now.

Mike Gibb: Unless you believe in the multi-verse, there is only one Spiderman. Can anyone — especially those in the ARM industry — hone similar skills? If so, how? Find a radioactive arachnid?

Jack Gordon: I’m confused. You say “unless you believe in the multiverse” as if it isn’t a fact. There are many different Spidermen (not to mention Spiderwomen, Spiderpigs, etc). But you don’t have to be bitten by a special spider to develop an entrepreneurial spider sense.

Here is a quick roadmap for anyone who feels like this is a direction they would like to explore.

1. Make a choice that you would like to begin seeing the world around you as a series of problems worth solving.
2. Drop the toxic people in your life who would be just as happy to see you fail and make new friends who are already doing the things you would like to be doing. This could be as simple as joining new social media groups.
3. We all have flashes of brilliance – usually fleeting. When it happens, commit to holding on to them by any means necessary. Carry a notepad, record into your phone, etc.
4. Do something – anything – to start following up on some of your best ideas. You don’t have to hit a homerun right away, just commit to exploring something small, testing the viability of an idea, testing a market, even just writing a unique report that would be useful to some group of people and giving it away. Start small and build the habit. Those skills are stackable and when the big idea hits, the more you have exercised them the more prepared you’ll be.

Mike Gibb: I saw a meme recently that said something along the lines of: if you hang around with five intelligent people, you will become the sixth. I think that really helps as well. There are some really bright people in this industry and exposing yourself to them helps a great deal in identifying ideas worth pursuing. The one difficulty I have had is letting go of ideas you think are good, but really aren’t. Just because you have an idea doesn’t automatically make it a home run. Is that something you have experienced, too?

Jack Gordon: I think that’s actually the norm and the homeruns are the exception. To extend the metaphor, swinging for the fences is rarely going to be a successful strategy in my experience. Keeping your head down, experimenting and failing, a focus on creating extraordinary value, practicing patience – those are the much more common ingredients that can come together and make something that connects.

Most of my business ideas have fallen flat for one reason or another, but enough of them have worked that it balances everything out.

Two parting thoughts on this subject. First, I’ve found that nobody really remembers you for the failed ideas. And second, all it takes is for one idea to work to make a difference in the world. I have been extraordinarily fortunate to find a handful of those.

Mike Gibb: What about the future of the ARM industry excites you?

Jack Gordon: One of my mantras is that there is opportunity in doing hard things. In my mind, there is still a lot of opportunity to innovate here, and the people with good ideas who are willing to work hard and navigate the regulatory morass have a fair shot at succeeding.

Personally, I am excited to dramatically expand our collector-level training offerings in 2022. We have spent years serving many hundreds of companies with our FDCPA training. With the Reg F launch date on us, we just recently introduced a great Reg F training for collectors that has been wildly successful. I attribute that success to two main factors: first, the urgency of the problem and the timeliness of our solution came together very nicely. But that wouldn’t have meant much if I hadn’t spent the last 13 years building a name and reputation for delivering quality products and services to this industry through both WebRecon and FDCPA Certifications – as well as the project we collaborated on – Collector.Live!

It hasn’t always been easy, but when you invest so much in an industry and build a good reputation, it is very gratifying that so many customers are willing to pay attention and give you the benefit of the doubt when you come to them with something new. I think it’s important to add that I am very protective of that reputation, and that causes me to also be very selective about the things I am willing to put my name on. You could spend 13 years building something special and lose it all in a week with poor judgement. That prospect is always weighing on me.

Mike Gibb: I share that same fear. It doesn’t take much to lose all the goodwill that you spend a career building up. Looking back, are there decisions you made not to do something — because of that fear — that you wish you had done differently?

Jack Gordon: Not really. I have been approached countless times to collaborate on “joint ventures” that were really thinly disguised reseller plans for someone else’s products and services. That is not interesting to me.

How about if I answer a question that is more interesting to me? Let me tell you about the one that got away. Many years ago I had dinner with a well respected leader from a major industry data provider who had a somewhat competitive product to WebRecon. I was just beginning to build a good reputation with WebRecon, but it was still early days. I went into the dinner hoping to get a strategic partnership with this company, but that wasn’t in the cards and I quickly discarded the idea. The dinner evolved into a freewheeling conversation about the industry, trends, opportunities and business in general. Near the end of the evening, before picking up the check, this person gave me a hot tip about what he saw as the next big thing, and that if I applied the WebRecon formula to it I could own it before anyone else got a foothold. That next big thing was active military scrubs for the Service Members Civil Relief Act. Not as sexy as litigious consumer scrubs perhaps, but it was a solid need that was about to take off. I didn’t have the resources at the time to start up a whole new dev process, so I didn’t pursue it. Within a couple of years, a half dozen or so companies sprang up to fill the need. If I had followed that advice and done it first, I believe I could have dominated that niche alongside litigious consumer scrubs and it would have been a very successful complementary product. That person I had dinner with is still a dear friend today and someone I am eternally grateful to for his graciousness in making me feel like a peer that evening, long before I felt like I had earned it.