We were lucky to catch up with David Berkowitz recently and have shared our conversation below.

Alright, David thanks for taking the time to share your stories and insights with us today. Can you tell us a story about a time you failed?

Failure’s a recurring theme. I run two professional communities, Serial Marketers and AI Marketers Guild, both of which I sold to Marketecture Media this year. Beyond having similar infrastructure, they share something in common that not everyone knows: I started both of them after getting laid off from two different companies five years apart. It’s quite likely that neither community would have launched if I wasn’t forced out to fend for myself. And how did I spend a lot of that time and energy fending for myself? By bringing people together. In hindsight, that looks like a more obvious straight line, but it wasn’t so obvious when I started each one.

What was more obvious while starting the communities is that when you’re out on your own, you can take more risks. You don’t have to ask permission. If you have an active client or you’re in the interview process for a job, you have to make some calculations, but there are kinds of freedom you have when you’re out there making your own luck and your own buck.

The odds were better than not that each community would fail. And I tried all kinds of initiatives for my communities that failed — member directories, paid upgrades, research studies, even a custom cryptocurrency (the $CMO Coin). But a lot of that failure, I think, showed my community members that I continue to care. And some of the experiments worked; they worked enough that Marketecture saw there’s some untapped value, and we can build something stronger together.

You know what my main benchmark was for Serial Marketers once it got going though? I’d wake up, log into Slack, and say to myself, “The community’s not dead yet.” Failing to die is the best kind of failure.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m a marketer’s marketer, the Serial Marketer. I thought after graduating college that I’d become a teacher, and I still can’t stop sharing whatever I learn. I also wanted to try my hand at writing, but I didn’t know how I’d do so. Twenty-five years after graduating, I finally published my first book — after writing thousands of columns, newsletters, and other pieces.

My work includes fractional CMO work, usually for earlier stage or smaller B2B businesses striving to stand out in crowded fields. Along the way, I’ve built two communities, Serial Marketers and AI Marketers Guild, that I now run under the Marketecture Media umbrella. My book, “The Non-Obvious Guide to Using AI for Marketing” (Ideapress, 2025) has led to more speaking and training opportunities where I help professionals and businesses at all kinds of stages make sense of how to apply AI for marketing.

Someone recently called me and said they were looking for a speaker, and they had three criteria: a futurist, a practitioner, and someone who isn’t full of it. I was the one person they thought met all three. I want to put that on a business card or some other collateral because I take a lot of pride not just in ideas but in being able to get things done, and being as unapologetically real as I can, whether it’s on a client call, on LinkedIn, or on stage. Apparently, some people still think all that matters.

We’d appreciate any insights you can share with us about selling a business.

I sold both of my communities that I built. I was never actively shopping them around but had three opportunities to explore it.

The first time, when I just had one community, I was having lunch with a publisher friend and was talking about my work situation. I said it was going fine, but I’d love to put more resources into the community somehow. He said maybe he could make that happen, and we discussed terms with a broad brush. I even met more of the team to explore it, but the financial situation wasn’t right for them at the time, and it didn’t go anywhere. It was still helpful for me to start thinking about how that all could look.

The second time was a longer process that arose where selling the communities came up as part of a job opportunity. Nearly six months into the process, it looked to me that while we were close to making something happen, the terms were different from what we had in writing before, and the updated terms weren’t to either side’s advantage. It was an offer I had to refuse, and it was tough. It would have been very helpful at a time where I was dealing with a lot of uncertainty professionally and personally. Many people who are way smarter than me probably would have accepted the changes and found a way to make it work. Even after I knew that walking away was the right thing to do, it stung for a while.

But getting back in touch with an old friend led me to Marketecture, with much different terms — I was still maintaining my consulting portfolio even while gaining a title with their team. What I lacked in the presumed predictability of a full-time job (which, of course, is hardly guaranteed to be long-term, especially these days), I gained in the confidence that Marketecture was setting these communities up for long-term success. The process from the first conversation to the deal closing took less than a month. And everyone who’s on their team and in their orbit is someone I respect so much both as professionals and people.

There’s no magic formula here. It’s possible that door #3 wouldn’t have been the right one, or it never would have opened at all, and I’d have had to wait for another. Or maybe door #2 could have worked out, and I could have played my hand differently and been writing about a success story from a different vantage point. Unless you’re traveling across the multiverse as in a Marvel movie, there’s no way to know. But it is important to factor in not just the terms but how you feel. Your gut matters.

Have any books or other resources had a big impact on you?

There are lots of them. I still often refer back to “Management of the Absurd: Paradoxes in Leadership” by Dr. Richard Farson, one of the pithiest books I ever read. One of his great lessons, for instance, is that we don’t learn from failure; we learn from our successes but the failure of others. And there are so many gems in there that I can’t do justice to. And then there’s the master work from behavioral psychology, “Thinking Fast and Slow” by Daniel Kahneman, based in part on all the research he did with his long-time collaborator Amos Tversky. It’s all a master class in how people act and think. Then there’s Brene Brown who said, “Solitude is not the reward for great leadership. It’s the path to great leadership.” For a borderline extrovert like me who grew up as an introvert, those words are so comforting.

But a lot of my influences come from literature and poetry and works of fiction. Reading Ogden Nash growing up, it opened my eyes to ways that you could challenge structure and defy the expected. Then there are many works by my favorite author, Philip Roth. In his first book, the collection “Goodbye, Columbus,” there’s a short story about a religious school student who asks questions that make others around him uncomfortable, and it’s a sign of how brave it can be to toss out seemingly un-askable questions. And, heck some influences can even come from comic books, like Miss Marvel who said, “Good is not a thing you are. It’s a thing you do.”

Behind me in my office, I have even more varied sources. There’s a three-volume Hebrew Bible set with commentary by Robert Alter sitting right next to Shel Silverstein’s work “Where the Sidewalk Ends,” with “The Complete Far Side” anthology by Gary Larson on the shelf next to it. As a Calvin and Hobbes book title goes, “There’s treasure everywhere.”

Granted, the book title that I think of most often is one Al Franken wrote long before he got into politics — but it’s a satire about him running for president. And that title is, “Why Not Me?” Not sure you’re the right person to start something or take something on? It’s a great question to ask yourself. And it’s led me to take a few risks that wound up working out.

Contact Info:

• Website: https://www.serialmarketer.net
• Linkedin: https://www.linkedin.com/in/dberkowitz
• Youtube: https://www.youtube.com/@aimarketersguild
• Other: https://www.amazon.com/Non-Obvious-Guide-AI-Marketing-Guides/dp/1646871863/