Running The Wrong Playbook

Try to imagine the dumbest rebrand a marketer can do. You can (and we will) cover some of the classic blunders too – like New Coke, the Amazon Fire Phone, or Gap’s logo no-go. But just like it’s useful to play a good idea forward, it can be equally useful to play a bad idea forward.

Let’s work through it together.

It’s all based on the principle of variance. Variance is a fancy way to say “risk” cuts in both directions. You can (and should, and we will!) use this mirror to your advantage.

If the math-speak intimidates you, think of it like this: if you can’t figure out a really good idea, you can always figure out a really bad idea and do the opposite. Not so bad, right? And, fortunately, the framework we’ve been playing around with, of how LESSS is More and Marketing is Sales at Scale give us a great sandbox to dream up anti-examples in.

What if… an Enterprise B2B company marketed themselves as a Boutique B2B company? It’s the bespoke trap.

Think about Salesforce. They sell a computerized rolodex to companies, with sales forces, who could use computerized rolodexes. While the product has some customizable features, the only way it works, from a profitability standpoint, is if a big company can roll their mostly uniform product out to an army of active users. Compliance helps a lot here. Both in terms of tracking and monitoring for quality control, and the willingness to use the system regularly and deeply.

If I can pitch Salesforce on a really bad idea for a moment – imagine me telling them, “You should make the product way more customizable. Boutique level. I want to see it bespoke. I want you to make the exact right rolodex for each end user so they think it’s magic, just for them.”

If Salesforce forgot they were Enterprise B2B and deluded themselves into thinking they should provide an artisanal solution to each end user, they'd destroy their profit margins and betray their core promise. They'd shift from offering a logical transformation – data tracking at scale – into a status-sexy one: bespoke magic, just for you. Never trust an institutional solution that promises that. It's still just a big, boring rolodex pretending to be a Rolex.

Example from the history books: Amazon and the Fire Phone.

A company who’s all about security (they are always there, and always ready to deliver) attempted to roll out a product to compete with Apple/luxury/status-sexy phone providers that people would show off owning. Not only did people not care – they couldn’t imagine Amazon that way.

There were no “Prime vs. XYZ” cultural moments presented in the way Apple built status-sexy through the “Mac vs. PC” ads. Marketing will tell the story, and will be a common thread here. Amazon couldn’t be status-sexy in smartphones because that’s not the transformation people already trusted them for - they were trying to sell a status upgrade they didn’t own. Bezos did (ingeniously) immortalize the mistake to shareholders by saying, “If you think this a big failure, we’re working on even bigger failures right now,” to cover the misstep. They are and were a growth company, after all, but this was an easily avoidable transformation mistake.

Back to variance, too – because if you want to win bigger, it helps to also know how to fail bigger. You have to at least respect the risk Amazon was willing to take, even if it was poorly chosen.

What if… an Enterprise B2C company marketed themselves as a Boutique B2C company? It's the artisanal delusion.

Think about Netflix. They sell stories, as a subscription, to millions of people, the world over. The transformation they offer is emotional. We subscribers “need” something to watch – to laugh, to cry, to keep us from sitting alone with our emotions (Ok, I know that’s less than generous, but it’s true), OR (more generously) to help us process and articulate what we're feeling. We return to their product for an emotional fix, because it works.

Netflix is Enterprise B2C at its finest: narrative plus performance channels moving behavior at volume.

Now imagine if Netflix decided to go in an different direction. What if I pitched them, terribly (is it bad that I’m good at bad advice?), with, “You know what? We're going to hand-curate queues for a tiny set of users, ONLY. Most of these people have terrible taste and we should subtly, or not so subtly, call them out on it. We’ll re-educate and save some people in the process too. We'll do it by not worrying about feedback anymore. If the modern world is increasingly devoid of art, we can make Netflix the modern art-house cinema!”

If Netflix forgot they were Enterprise B2C and deluded themselves into thinking they should provide an artisanal, hand-crafted experience to each subscriber, customer acquisition costs would explode. They'd never reach the scale needed for original content budgets, global licensing rights, or keeping the lights on. They'd destroy the unit economics that make the whole thing work. And worse – they'd shift from offering an emotional transformation (connection, escape, processing feelings) into something logical to shareholders (“we know best”), and status-sexy to the very small number of users who they would hit the bullseye for, if anyone (Fire Phone all over again).

Example from the history books: New Coke.

In the 1980s, Coca-Cola ran one of the most famous campaigns in advertising: “I'd like to buy the world a Coke.” In the middle of the decade, they shifted. “We’ve got a taste for you,” and “America’s Real Choice.” Those slogans didn’t last, and by the late ’80s they ran, “When Coca-Cola is a part of your life, you can’t beat the feeling.” What happened in the mid-’80s? New Coke. A classical betrayal of the emotional transformation – the brand identity of connection, belonging, warmth – for a logical and paternalistic decision of declarative authority with no room for individual comfort.

Coke briefly forgot they were selling feelings and rituals, not lab-tested taste upgrades. They'd treated an emotional enterprise relationship like a logical product improvement problem, and the backlash was swift.

If you're running an Enterprise B2C play, don't fall in love with personalization. Don't try to hand-craft your way to success. The math doesn't work, and you'll kill what made the thing special in the first place.

What if… a Boutique B2C company marketed themselves as an Enterprise B2C company? It's the algorithm trap.

Think about Louis Vuitton. For decades, they've sold status-sexy. A “look what I bought myself,” or “look what someone gave me” brand. The transformation is specific (and really important to recognize, with all things luxury): whoever gets the item also gets a story to tell about it, usually including from who, when, and why. It’s an ultimate word-of-mouth flex. That storytelling is what great boutique marketing always generates. The brand lives in the narrative people tell others about owning it.

Now imagine if Louis Vuitton decided to go mass-market. Here’s bad strategy Mat’s worst take: “You know what, folks? We want sales, so what if we flood Amazon with discounts? We can crank out way larger volumes, yes, with less profit margin, but still way more than anybody else can get for similar goods. And then, once we have more data on our buyers in these new spaces, we can optimize for conversion and CAC going forward, to keep reaching more people, faster – just like the best Enterprise B2C companies do.”

The transformation doesn't survive that. I’d kill Louis Vuitton if they tried that for more than a month. Because more exposure is the antithesis of status-sexy. Status-sexy requires an understanding of scarcity. More reach, in this sense, doesn't mean more storytelling. The more you optimize for algorithm and volume, the less special it inevitably feels. You can make it secure by being ever present, or you can make it logical by being the rational choice, but you will lose all of your status-sexy in that crossover.

The fewer people actually talk about the product, and the more people who talk about where they got a deal on the price, the faster the valuable word of mouth would dry up. The sick part here is that even though the product hasn’t gotten any worse – the distribution method just destroyed the feelings of rare, referable, and IYKYK recognizable where all the margin lives.

You never want to turn a boutique relationship (scarcity, story, you “know a guy”) into a commodity play (discount codes, blasted ads, everyone has one/can get one). There’s no mid version of status-sexy.

Even at smaller scale, this happens all the time. Think about a neighborhood restaurant that's famous because it's “hard to get a table.” Imagine you’re cool, and the owner knows you from way back, and loves how you’ve discovered how great that spot is. Every time you walk in – there’s a special nod and excitement. But then, the owner decides to expand, opens three more locations, starts talking franchise money, optimizes the menu for mass appeal – like adding kids menus and featured apps, all of which run Facebook ads now across the whole region. Every successive location is a little less special. The story gets diluted, and like the food, becomes blander and blander. People stop talking about it because it's… just another restaurant now.

Or think about a creator who goes viral for something weird and specific, then chases virality harder – more content, more algorithms, more optimization. The weirdness was the point. The specificity was the magic. Niches, by definition, are weird! And the internet makes more weirdness reachable than ever. But once you start stretching for more awareness, once you start searching outside the niche, you start optimizing for reach, and you optimize away the thing that made people care in the first place.

Example from the history books: The Gap logo redesign.

In 2010, Gap decided they needed a rebrand. Keep in mind, this was in the wake of the Global Financial Crisis, the US consumer was not in good shape, and the much-loved mall-based retailer was hurting in a bad way for reawakening their business. It’s easy to forget that they’d been present in mid-tier American life for decades. The Gap was a fixture, a reliable option, a piece of countless middle class middle school wardrobe history, across more than one generation.

The brand had weight because it had been there across so many Americans’ lives. The crisis and ensuing recession threatened the continuation of the Gap story. Competition intensified. They felt pressure to signal “new, modern, cool” to draw people back to them. So they hired a design firm and rolled out a new logo, with a clean, minimal, corporate, generic, “did you make this in Microsoft Word” vibe. All of a sudden The Gap could have been any other brand.

The backlash was immediate and fierce. Customers didn't recognize it. Social media mocked it. Loyal buyers felt betrayed. The decades of presence got erased by a logo that signaled nothing. It didn’t help that Gap spent $100 million on the rebrand and reversed it in six days. Maybe I really should think about this bad strategy role a bit more seriously. That’s a good payday, but – I couldn’t live with myself.

What happened was Gap confused its relationship. They had a boutique-feeling brand – emotionally tied to belonging in people's lives across decades. But they tried to execute it like enterprise: optimize for modernity, signal “we're still relevant.” They weren't trying to make it secure or logical or status-sexy with any clarity either. They just tried to make it new. And in doing so, they broke the thing that actually worked.

Remember when the preppy kid became a goth kid over the summer? This was kind of like the reverse of that. Everybody thought it was weird, said, “Please stop,” and at least The Gap listened in this case.

If you're running a Boutique B2C play, don't chase the algorithm. Don't optimize away the weirdness, or at least the specialness of your relationship with your customer base. Don't try to make it for everyone, just bank on the somebodies who you need to remind to keep coming back. The moment you do, you lose the reasons people actually return to you.

What if… a Boutique B2B company marketed themselves as an Enterprise B2B company? It's the premature scale trap.

Think about a specialist advisory firm. Small, focused team. They work with a very specific kind of client on a very specific kind of problem. The transformation they offer is logical and emotional combined: “We see something in your situation nobody else sees, and we'll help you act on it.” One delighted client becomes three more via a case study, a reference call, a “you should talk to them” email. There’s a sense of reference at scale – where it’s not based on leverage or volume alone. This type of word of mouth doesn't happen by accident, or by pure status-sexy signaling, it happens because the work is so specific and the relationship so trusted that clients can't help but evangelize.

Now imagine if that specialist firm decided to go enterprise. Here's one more bad pitch from yours truly: “You know what you guys could do here? I think you need to professionalize. We need a more predictable pipeline to drive this next wave of growth. We need to crank cold outbound, build our funnel metrics, get our sales cycle documented, run performance on ad spend, optimize our messaging for broad appeal. If we do that, we can be more like Salesforce and less like one-referral-at-a-time. Private Equity will be banging down our door with a fat check within 2 years.”

The moment they take this advice, the thing that originally made them valuable dies. The PE reference at the end – there are too many real examples of this (and some counter examples, but let’s be real). Boutique B2B doesn't win on reach or volume or scalable playbooks. It wins on the specific insight, the trusted relationship, the fact that you're weird in exactly the right way for your niche, with a quality aspect over a luxury angle. The more you chase outbound volume, the more you optimize for funnel metrics, the less weird and referable you become. Your best clients – the ones who know you're the only people who understand their specific problem – start to sense they’re leads in a CRM instead of “our people.” The personalization that made them want to work with you gets systematized. The trust gets replaced with process.

And here's the resultant doom loop: the referrals slow down. The word of mouth that used to fill your pipeline dries up because you've signaled (loudly, through your actions) that you're chasing everyone now, not just the right fit. So you double down on cold outbound. You hire new (and less experienced) salespeople. You build a lead scoring model. You spend more on ads to replace the organic growth you just killed. Your margins compress. The firm that used to run at 70% margins because clients came in warm, via referral, now runs at 40% because you're buying volume at scale. And you're still not winning against actual enterprise firms who have 1,000 salespeople and a real product.

Your precious little professional practice officially becomes the worst of both worlds. You find yourself paying enterprise cost of sales without enterprise leverage or scale. You have the overhead of a big firm without the unit economics that make it work. You’re a runt boxing heavyweight and your constant headaches constantly remind you of how you used to feel like a contender, and you daydream why you don’t anymore. If only you could see, it’s who you’re competing against once you trade in your transformation.

Real-world example: any specialist agency or boutique consulting firm that got addicted to pitch decks and “business development” instead of protecting the referral core.

It really does happen constantly. I’ve seen it too often in my corner of professional services. A small firm does great work for a tight niche. Then they hire a VP of Sales who says, “We need to systematize this. We need repeatable processes. We need to go after bigger clients.” They build a playbook, hire junior consultants, start chasing volume. The work gets diluted because you're now serving clients who aren't quite the right fit. The best people leave because the work isn't as focused anymore. The firm that was known for being weird and specific becomes known for “oh yeah, they do consulting.” The referrals were paying for everything - now you're paying for everything.

The specialist firm wins because it's not trying to be enterprise. The moment it tries, it loses the only advantage it had. It’s great if you’re trying to exit, re: sell to a larger, more economically aware buyer who wants to sell security, but it’s terrible if you’re trying to keep earning your margin on work that both makes sense and provides a genuine, human connection (logical + emotional).

If you're running a Boutique B2B play, protect the referral core. Don't confuse “growth” with “more.” One reference call that leads to three more is better than a hundred cold emails that lead to ten mediocre conversations. The math might feel worse at first, but the margins, the predictability, and the quality of work tell a very different story.

With my bad strategist hat as far away from my head as I can throw it – allow me to wonder out loud about what I’m trying to not screw up. The clearest paired example I can definitely talk about publicly is probably the differences in two of my podcasts, Excess Returns and Just Press Record.

Excess Returns is about a logical transformation. It’s investor education, and it most rhymes with an enterprise to consumer / B2C distribution framework. If I think about the best media examples of this, I think about news and sports content. I think about how the audience has sub-categories they associate with, like political parties and teams, and how their inherent emotional affinity gets reframed into a logical argument they feel smarter about consuming.

We’d go wrong with Excess Returns if we put emotional first. We’d definitely get a subscriber bump by going straight doomer, but – that’s also not who we are. That would be a betrayal of the niche that got us this far. Likewise, security via our presence is a sub-category of what we do, but not the value transformation we’re offering. And as for status-sexy, podcasting is officially the lowest status job so, I can’t imagine that’s even on our bingo card.

If Excess Returns is to focus on anything in 2026, it’s how to make sure the audience knows we are offering a logical transformation in an emotionally charged world, and subscribing will help keep them on topic and on track.

Just Press Record is a totally different beast. Which is part of the fun of running three podcasts side by side, because I can play with the breadth of this framework. The Intentional Investor sits somewhere between these two - in the way that it's got the emotional connection of JPR but the logical clarity of Excess Returns. JPR being a 2-guest show makes it totally different from the slightly more standard interview show format that Intentional Investor inhabits.

The idea of networking as forming an actual, genuine, emotional connection with a stranger is in short supply. It’s very boutique business to customer, by design. Kind of an anti-LinkedIn in many ways. Very much an old school matchmaker or yenta situation.

We’d go wrong with Just Press Record if we put logical first. There’s not a clean logic or “learn these lessons” formula here. It’s too unpredictable. The same goes for security. Yes, the show reliably shows up, but the guest pairings are so niche and, again, unpredictable, that there’s no way my personal flavor of ADHD is going to have mass appeal.

As for status-sexy, there is an element of that for the guests, but it’s only valuable if the attention on me, as host, grows. Right now, nobody really cares who I am, except for a handful of people. I have a reputation as a connector, but it’s truly word-of-mouth only. If at some point me pairing you becomes a more desirable status symbol, then I can lean harder on this transformation, but as of now, my gut says the emotional aspect is stronger.

If Just Press Record is to focus on anything in 2026, it’s how to make sure the guests who come on know my goal is to facilitate a genuine connection with another authentic individual I believe, at an emotional level, will be valuable for them to know going forward. Saying yes to being a guest will get them that connection. Watching from home will offer the audience an example of who these people are, and with my Grow Your Network posts on each guest, hopefully inspire them to reach out.

I used these examples because I want to showcase the differences in strategy for two projects I’m running in real time. Excess Returns lives and dies on logical clarity. Just Press Record lives and dies on emotional authenticity. If I run the Excess Returns playbook on JPR, I kill the thing that makes it work. If I run the JPR playbook on Excess Returns, I end up as a niche podcast that reaches 12 people and never scales enough to serve anyone.

My favorite part about applying this framework isn't exclusively thinking about worse vs better, or worst vs. best. The power of the framework is in having a system to work out which playbook you should be running plays from, and then to have the discipline to not switch midstream just because one feels easier or more scalable than the other, especially if it comes from some outside consultant pitching a complete makeover.

This post started with variance and I hope these examples remind you of the reality of variance. All business is taking risk. Risk always cuts in both directions. Now you can see how big businesses are running these frameworks, and how I am, too.

It’s officially your turn – how are you analyzing whatever business + transformation type you’re running?