In this episode of the No Days Off podcast, host Brian Gubernick draws on lessons from his long‑time business coach, Vietnam‑veteran Mike Fleming, to explain the military concept of flanking and how it can be translated into business strategy and personal life. Flanking—attacking an opponent from the side rather than head‑on—is illustrated with the World War II Battle of the Bulge and General Patton’s maneuver. Brian then outlines concrete ways entrepreneurs can “flank” competitors: targeting underserved market niches, expanding into geographic areas where rivals are weak, differentiating products, employing flexible pricing, leveraging emerging technology, and forming strategic partnerships. He cites Apple’s iPod launch and Tesla’s early electric‑vehicle focus as classic business flanking examples. Finally, he shares a personal parenting anecdote where bringing in a third‑party to teach a lesson mirrors a flanking tactic, and encourages listeners to consider side‑attack approaches in both business and life to gain momentum before confronting competition directly.
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Thank you for joining me today. It's Brian Gubernick, and welcome to the No Days Off podcast, where we believe that every single day brings a new opportunity to get better. I have a business coach. I've mentioned him many times here at No Days Off. His name's Mike Fleming, and I've been working with Mike for 10, 11, 12 years. Mike is a Vietnam vet, a military buff, grew up in a military family, not only experienced military battle, war firsthand, but, but has studied it for years and years and years. And a lot of what Mike shares with me are his experiences in leading troops, uh, being in combat, the strategies. I mean, a lot of it Well, I hate to make comparison. A lot of what he experienced translates into the business world. So, what Mike shares with me, you know, are his experiences. And we talk quite a bit around things that occurred in the military. Now, I did not serve, but I can learn a ton from a guy like Mike. And so, one thing that Mike's always talked to me about is this strategy known as flanking. Strategy known as flanking. Now, what is flanking? Flanking is a military concept. That involves attacking the enemy from the sides rather than head-on. And the objective is to gain a strategic advantage. Flanking maneuvers are designed to surprise, designed to overwhelm the opponent by targeting their weaker or less defended positions. And it ends up disrupting the opposition's formation and you gain a tactical edge in doing this. I started thinking about this because I was watching something. Documentary, documentary recently on World War II, and it talked about the Battle of the Bulge. If you went to any high school history class, you probably heard of the Battle of the Bulge. I won't get into too much of the specifics, but basically it was Hitler's last stand. And General Patton, representing the Allies, he pulled off this flank maneuver, and in doing so, he marched his troops like 90 degrees north from where the battle was to occur in these completely adverse, like terrible weather conditions, and he ended up attacking Hitler's army from its— from weaker positions and really disrupted everything and led— it was one of the things that led to the conclusion of that war. So I was watching that, I was thinking about it, and it reminded me of all the conversations Mike and I have had about flanking. Now, when Mike's talked about flanking with me, this military concept We were generally taking that concept and we were applying it to business, to the things I was working on. In business, the concept of flanking can be applied in several ways in order to gain a competitive advantage. Here are some strategies. I want to talk some strategies with you for using flanking in a business context. The first place, uh, where my head goes is in identifying market niches, right? So instead of competing directly with an established competitor or player, instead look to identify underserved or maybe overlooked market segments. Maybe offer specialized products or services that cater to the unique needs of these, these market niches that I'm describing. Bottom line, instead of attacking a player head-on, an established player head-on, Look for something that's underserved or overlooked. This is how we would flank in business. Now, this kind of leads me to geographic expansion. If you're looking to expand your business, expand into a geographic area where competitors maybe have a weaker presence or no presence at all. This can help you establish a strong market position without facing intense competition. I guess a good example of this— well, I get it, we're still proving it out, but you're all listening to the No Days Off podcast, you're on this journey with me. Recognize that, you know, part of the reason we run a podcast that is 8, 9, 10 minutes in length, 12 minutes in length, uh, is because, well, a lot of business podcasts and entrepreneur podcasts, personal growth podcasts, they're long form, you know, they go 30, 40, 60 minutes, some are an hour and a half, 2 hours. And for me, you know, we thought, let's run something shorter that's different. This would be my attempt to flank, in that I'm not going after those that have a stronger market position where there's intense competition. Instead, I'm looking for space or a niche where others are not. And so this would be a flanking maneuver. Next area, or next thing I'm thinking about, is product different— differentiation. So introduce something innovative, like an innovative feature or a variation of an existing product that addresses specific customer pain points. This in turn can attract customers who are not, not fully satisfied with the current offerings in the market. So what can you bring to the table that isn't presently out there right now that would attract people to you, attract people to your product or your service? This is you creating something different, which leads me to even flexible pricing strategies. Offer more flexible or competitive pricing options. Maybe it's tiered pricing or subscription model or bundled services. This attracts price-sensitive customers away from your competitors. This would be flanking. Maybe you can leverage technology and that improves efficiency and improves the customer experience and you're doing it before your competition does. This creates this unique selling proposition and it differentiates you and your business from the competition. Last thing I'm thinking around, strategic partnerships. If you form alliances or partnerships with other businesses to enhance your offerings or enhance your reach, you are in fact flanking. This could help you enter new markets, improve your value proposition without having to deal with what I would say is direct competition. Now, a couple examples, a couple examples of, of flanking in business just to kind of demonstrate this. The first one that comes to mind for me, and we use Apple quite a bit, but frankly, it's because they do so many things right and have over the years, especially when Steve Jobs was in, in the leadership seat. But the iPod— when Apple introduced the iPod, it did not aim to compete directly with existing MP3 players based solely on price or storage capacity. Instead, Apple focused pretty much on a superior, superior user experience and the ease of the use of iTunes and the sleek design. This was a flanking maneuver that targeted consumers who valued these things and maybe didn't even know they valued them. This allowed— this is one of the things that allowed Apple to begin to dominate the market. So again, they didn't attack MP3 players head-on. They instead, you know, went after, you know, a flank in that the user experience and ease of iTunes and things like that, and the design was appealing. Tesla. Tesla's a good example. Tesla flanked traditional automakers. They flanked Ford and, and GM and Chevy. They flanked these guys by focusing on high-end electrical vehicles, right? There was no competition in the electric vehicle market. They offered innovative technology, they offered a superior experience and performance, they had a strong brand, they had Elon. And so Tesla established a strong foothold before any of the traditional car makers could respond. So Apple and Tesla are some really, really good examples of flanking in business. So the thought for you, I guess the focusing question for you, whereas we traditionally look to go head-on and attack our competition, because call it what it is, like, you know, in business we are battling it out and we, we go head-on sometimes. But what I want to challenge you on, or what I want to get you thinking about, is how you could gain market share, grab market share you know, earn more customers by instead of going head-on, attacking from the side? How can you attack weaker positions or grab market share that, that comp— that, that primary competitor is not even thinking about? How can you gain momentum, increase revenue, and over the course of time, as you gain a foothold, then potentially look to attack head-on? But only once you've established a position. How could you flank? Now, as crazy as it sounds, I've talked about flanking with Mike in my personal world as well, and I'm gonna give you a really good example. I talk about parenting quite a bit. It's kind of a strange pivot, but, you know, Mike had said to me, you know, how do you plan on teaching your kids ABC, whatever this, that particular subject is? and in some cases, maybe my kids are going to hear from me, right? They're going to respect what I'm saying, they're going to listen. But there's a lot of things that I want to teach my kids that they're just not going to listen to that. So Mike would say, well, how would you go about flanking? And the answer oftentimes is, who can I bring in and teach that lesson that's not me? Who can I bring in, put it in front of the kids manipulatively? And I'm not using that— manipulative is not a bad word here. But how can I get the message across without it having to come from me? How can I convey a message and it's coming from somebody else that they'd rather hear it from? Many of you running businesses have this experience where you teach something to your team or your people and it doesn't seem like it resonates or hits, but then somebody else comes in, says the same thing you said, and now it's suddenly heard. That would be a flanking maneuver if you were purposeful in doing that. Follow me? So again, you don't always have to attack head-on. I think if you're a savvy business owner, savvy entrepreneur, or business person, you are always looking for ways to accomplish the mission. And oftentimes accomplishing that mission means to attack from the side or from different angles versus head-on. How might this apply in your world, both business and personal? A lot to think around. That's all I have for you today, the No Days Off podcast. Thank you so much for listening, and remember, every single day brings a new opportunity to get better. So let's get after it.
