Playbook Broken Podcast

Marc Sirkin
  • 5.0 (1)
  • Technology

Sharp, subversive takes on marketing, AI, and business strategy. Playbook Broken includes deep dives, interviews, and bite-sized insights for people who don’t play by the rules. marcsirkin.substack.com

  1. Apr 10 ·  Bonus

    OpenClaw meetup in Raleigh, NC

    A brief debrief from the OpenClaw Meetup in Raleigh, North Carolina on April 9th, 2026. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    2 min
  2. Technical Branding: The Discipline That Doesn't Exist Yet

    Jan 6

    Technical Branding: The Discipline That Doesn't Exist Yet

    “Stop watching gurus telling you what to do.” Myriam Jessier doesn’t ease into conversations. She’s a technical SEO strategist, co-founder of Pragm, and possibly the most irreverent voice in search right now. And she’s tired of watching marketers fail because they’re following advice that worked in 2019. “There’s best practices for SEO out there,” she tells me, “and then there’s your business reality. The stuff that actually works for you.” Here’s what she means: while you’ve been optimizing for rankings, the entire game changed. AI didn’t just speed up search. It collapsed the distance between how machines read your brand and how humans experience it. And most companies have no idea it’s happening. AI Search Isn’t a Problem. It’s a Situation. Myriam draws a distinction I can’t stop thinking about. “Do you know what the difference is between a problem and a situation?” A problem has a solution. It might be expensive, time-consuming, resource-intensive. But it can be solved. A situation simply is. GDPR isn’t a problem. It’s a legal framework. You don’t solve it. You operate within it. “Search being AI-powered is not a problem,” she says. “It is a situation.” This reframe matters because most marketing teams are still treating AI search like something they can fight their way through with better content, more keywords, smarter technical SEO. They’re wrong. “The longer we operate on this premise of ‘I have lost something and I’m upset,’ the longer we are closing ourselves off to figuring this out.” AI search is physics now. You don’t optimize for gravity. You build for it. Thanks for reading Playbook Broken! Myriam brings the heat in this post - please share it! The KGB Problem Here’s Myriam’s analogy that stopped me cold: “You as a brand should not be like the KGB bugging every single seat and trying to figure out what is going on for each person.” Traditional SEO was about control. You controlled your content, your keywords, your metadata. Google played matchmaker, but you controlled the inputs. That’s over. Now you have an AI brand ambassador showing up between you and your customer, deciding what’s relevant based on context you can’t see. Chat history. User preferences. Inferred intent. “You cannot force people to pay attention to you,” Myriam says. “You should be doing your job in a way that makes sense in the user’s context. You should be relevant in that context. The end.” This is where most brands are getting it wrong. They’re still trying to rank first for “cancer” when what they should be asking is: In what contexts does our brand actually belong? While You Weren’t Looking, SEO and Brand Became the Same Thing “If you want to get really technical about it, this is technical branding.” Myriam drops this like it’s obvious. It’s not obvious. Nobody’s talking about this. “What you are asking your SEO to do is to understand your brand DNA, and they didn’t care about it at all for years. And now you want them to pull magic. It doesn’t work that way.” Here’s what she means: AI doesn’t just crawl your website anymore. It synthesizes your entire brand presence—your PR pushes, your Reddit threads, your leaked memos, your CEO’s unhinged tweets—and creates a narrative. You don’t control that narrative. But you better understand it. Myriam’s framework has four parts: * Your Known Brand: What you put out. Your campaigns, PR, official messaging. This is what you control. * Your Latent Brand: What people say about you. If you have a subreddit called “F**k Nestle” with hundreds of thousands of followers, that’s latent brand. You don’t control it, but AI is absolutely ingesting it. * Your Shadow Brand: The stuff you know internally that hasn’t come out yet. Leaked memos. Lawsuits. That thing your CEO said in a closed-door meeting. But also—your quiet DEI programs, your sustainability initiatives that aren’t press-released yet. “Can you discreetly start feeding the LLM some information so that when ChatGPT comes up and says, ‘No, but they actually are,’ there’s data that can point to it?” * Your AI-Narrated Brand: The synthesis of all three. What the machine actually says about you when someone asks. “That’s your AI brand. It’s not what you say. It’s those three bits together.” Most brands are optimizing the first quadrant and ignoring the other three. Then they’re shocked when ChatGPT describes them in ways they’d never describe themselves. Thanks for reading Playbook Broken! Subscribe to get this in your inbox! The Practical Move Nobody’s Making Myriam doesn’t do theory without action. Here’s what she tells CMOs to do right now: Test 1: The Packaging Test Take a picture of your product packaging. Ask ChatGPT what brand it is. Ask it why someone should buy it. “If you see that it’s not answering properly, you have a problem.” Test 2: The Logo Test Upload your logo to Google Cloud Vision API (free demo). If Google recognizes your entity and says “logo of [your company],” your technical brand is working. If it doesn’t, you’re invisible to AI. Test 3: The Sentiment Test Take your product images with humans in them. Run them through Google Cloud Vision API or an LLM. Check the confidence scores on detected emotions. “If you’re looking for a fun, flirty summer dress, Zara models with resting b***h face don’t scream fun.” Test 4: The Reviews Test Take all your reviews. Feed them to an LLM. Ask for sentiment analysis. “There’s somebody in your company that knows how to do this.” These aren’t theoretical exercises. These are diagnostic tests to see if your brand actually exists in the way AI systems understand brands. If you fail these tests, your SEO team can’t save you. Your brand team can’t save you. Because the gap between them just became your biggest liability. And that gap? It’s costing you customers you’ll never know you lost. Because they’re getting a version of your brand story you didn’t write. The Cost Per Wear Problem Before we wrapped, Myriam told me something about how she forces herself to make hard decisions. She grew up in a well-off family, then became “dreadfully poor” at 18. Had to rebuild. Now she runs two agencies and speaks globally, but she can’t shake the trauma of living on $2 a day for food. So she invented a metric: cost per wear. “I can buy the $300 dress. I just have to wear it a hundred times because my cost per wear is $3.” Fast fashion that falls apart after ten wears? That’s $5 per wear even if you paid $50. The expensive dress is actually the rational purchase. “Of course I should be buying the expensive one.” Here’s why this matters for marketing: You’re making the fast fashion decision with your marketing stack. Buying tools that feel cheap but fall apart under AI pressure. Optimizing for metrics that made sense when search was about rankings. The expensive move—the one that feels irrational right now—is investing in technical branding. Building the systems that make your brand comprehensible to machines and humans simultaneously. That feels like overkill until you realize: you’re going to “wear” your brand positioning every single day for the next decade. What’s the cost per wear on your current approach? Your Playbook Is Broken SEO and brand were separate functions because the interfaces were separate. Humans experienced your brand. Machines crawled your site. You could optimize for both independently. AI collapsed that separation. Now machines experience your brand the way humans do—through synthesis, context, sentiment. And humans increasingly experience your brand the way machines do—through AI-narrated summaries, zero-click answers, contextual recommendations. The companies that win won’t be the ones with the best SEO or the best brand team. They’ll be the ones who realize those are the same team now. Technical branding isn’t a nice-to-have. It’s not a 2026 priority. It’s the discipline you should have started building six months ago. The uncomfortable question: If Myriam ran your brand audit tomorrow, what would the packaging test reveal? Don’t tell me you need better data. Don’t tell me you need buy-in from brand. Don’t tell me you’re going to wait and see. Take the picture. Run the test. Find out what AI actually thinks you are. Because your customers already did. That’s a wrap on Season 1 of Playbook Broken (the show). More posts to come while we plan season 2… in the meantime, please do share with your network! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    42 min

  3. 12/10/2025

    Your Marketing Calendar Is Dead. Here's What Kills It.

    Tejas Manohar was at Segment when it sold to Twilio for $3B. Now he’s co-CEO at Hightouch, watching marketing teams make the same mistake over and over. They’re using AI to make their old playbook faster. Wrong move. “You can’t assume that people are going to interact with your website the same way they interacted with your website a few years ago,” Tejas said. “Consumers are going to be viewing their travel planning in ChatGPT. If you’re just optimizing your website, that’s not going to work.” The marketing calendar worked when you could only ship 10 campaigns a quarter and customers had three alternatives. Now AI can generate thousands of variants and customers are researching in ChatGPT. The constraint was production capacity. That constraint is gone. March 3, 2020 Before Hightouch, Tejas built a travel company. March 3, 2020, every metric went to zero. He shut it down. “What do you want to be doing with your time? Do you want to wait out a pandemic or do you want to do something? We just had to make the decision to ignore sunk cost fallacy.” Most marketing teams are in this moment right now. Your playbook worked. You know how to execute it. You have dashboards that measure it. But every signal says it’s broken, and waiting won’t fix it. Thanks for reading Playbook Broken! I’d love it if you would share, re-stack or comment! Why Personalization Actually Failed We’ve been lying about one-to-one marketing for 30 years. CRM was going to deliver it. CDPs were going to deliver it. Neither did. “We’ve had data for a really long time. What’s really different now is understanding each customer.” Before, you dictated the rules. This segment gets the credit card offer, that segment gets subscriptions. “You didn’t have a technology that could actually look at every user and think about the individual journey for them.” AI checks a hundred times more variables than any analyst. It experiments with offer sequences, timing, amounts, ordering. It figures out whether $10 or $20 works better, and whether that varies by purchase history. The catch: “It’s a big change to go from a world where you’re releasing five, 10 marketing campaigns a week to a world where you have this huge database of content and this AI system is helping decide who to send them to.” Entirely new workflow. Entirely new org chart problems. The Conversation Nobody Wants to Have Technology is ready. Your organization isn’t. Think about Martec’s Law which I seem to invoke all the time lately. Sure, the tech is cool, but can your people and teams change fast enough to keep up? “Just having new tools that do the old process a new way doesn’t cut it. You need to get one that has a new mindset of how we can use AI in a different way.” Merchandising wants their new product pushed to everyone. Brand spent three months on messaging. The CEO has quarterly goals that require specific numbers. All of that runs into an AI that says 75% of your customers aren’t ready yet. “Your merchandising leader who is only responsible for one product, they’re not going to be happy when you’re not sending it out to all their customers. It’s a hard conversation.” This is where it dies. Not in the tech selection. In the hallway where someone tells the merchandising VP the AI overruled them. Like the Playbook Broken vibe? Why not subscribe? What’s Ready, What’s Not Tejas runs a company selling this stuff, so factor that in. But his read is right. “AI is actually really good at analysis of data and getting insights from data. That’s the functionality that is really reliable today.” Content generation? Not (quite) ready. Fully automated creative? Not (quite) there yet. But close and getting closer. But AI figuring out which customers want which offers, when to send them, how to sequence them? According to Tejas, that works now. “You shouldn’t be manually running all these queries to figure out what drives your customer to high LTV. You should be asking a system that uses AI to tell you.” And the downside is lower than you think. “Let’s be real. The current state is that you’re sending a lot of things that are likely not relevant to your customers.” 20% open rate, 1% clicks. You’re already wrong 99% of the time. It’s the Brain, Not the Interface With every new model release the picture gets clearer. These are not just “upgraded” chatbots but pieces of systems that break down problems, reach for tools, and delegate work. “It’s not just having a better chatbot interface. You need an interface where you can say a problem and it can help you break it down. It’s not the interface, it’s the brain.” The calendar is dead. The question isn’t whether AI will replace your workflows. It’s whether you’ll replace them before your competitors do. Your March 2020 moment has already happened, did you notice? This episode of Playbook Broken was previously published on MarTech.org as “The CDP fantasy is over.” Around the Town * I spent the weekend in Las Vegas and now engineering and innovation is on my mind. We did a half day at the Hoover Dam, an experience not to be missed. The engineering and scale of that project is mind-blowing. From there, we had our first “Sphere” experience, seeing Zac Brown Band absolutely crush it. The Sphere is a modern marketing marvel, truly astounding to see it in person. * Our AI for GTM even on Dec 3 was a blast! We had nearly 70 folks hang out with us from 9-5 to learn practical AI skills. Super fun. Excited to do another event. * I’m nearly done reading Neal Stephenson’s 880 page Fall; or, Dodge in Hell: A Novel which, as with all of his books, is mind-bending in all the best ways. How about a virtual world where we go to become immortal and recreate meatspace? Yea, he wrote that. Let’s see if he can stick the landing. I’m 75% of the way home! Thank you for watching, listening to and reading Playbook Broken!. If your playbook is shaking, we’re here to help rethink and rebuild it with you. —Marc This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    44 min
  4. You’re Not Data-Driven. You’re Just Scared.

    11/14/2025

    You’re Not Data-Driven. You’re Just Scared.

    I’ve spent my career trying to marry art and science. The creative and the analytical. The gut instinct and the spreadsheet. Never leaning too far in either direction because the best decisions live in that tension. So when Philip Armstrong told me most executives use “we need better data” as a stalling tactic, I immediately recognized the pattern. I’ve seen it a hundred times. Hell, I’ve probably done it myself. It’s not that they don’t trust the data. It’s that they don’t trust themselves to be wrong. No one ever got fired for hiring IBM. Philip Armstrong is ex-Nike, now SVP at Truth and Data. He’s rebuilt customer journeys inside some of the world’s best brands and messiest data orgs. And he’s seen the same pattern everywhere: companies drowning in data, starving for action. Here’s what he told me that I can’t stop thinking about. There Is No Perfect Data. Stop Pretending There Will Be. “I see a lot of people waiting for the perfect data to make decisions,” Philip said. “And there’s no scenario where you have perfect data.” Let me repeat that for the leaders hiding behind their dashboards: there is no scenario where you have perfect data. Decision-making with incomplete information isn’t a bug. It’s the job. If you had perfect information, you wouldn’t need judgment. You’d need a spreadsheet and an intern. But “we need more research” is socially acceptable. It sounds responsible. Strategic. Thoughtful. It’s actually just expensive cowardice. Your competitors aren’t waiting for perfect attribution. They’re making the call with the best data they have right now and iterating based on what they learn. You? You’re waiting for a certainty that will never arrive. Thanks for reading Playbook Broken! Subscribe to get it in your inbox! Three Conversations Beat Three Thousand Data Points Here’s Philip’s move that sounds insane until you think about it: “When you interview like three or four people, you get 90% of the most significant changes that you need to do. If you interview another thousand people, you get a long tail list of stuff that doesn’t really move the needle.” He learned while doing user experience testing for streaming services. Three interviews led to picture-in-picture play and sound-off video for social media; features that became industry standard. When he brought those insights back to leadership, they wanted statistical significance. Sample sizes. They were addicted to the massive web analytics datasets where n=100,000 feels normal. Sound familiar? Does to me. But here’s what massive sample sizes actually do: they create averages. And averages bury signal. The interesting stuff lives on the edges. In the outlier behavior. In the thing that three people said that makes you go “wait, what?” You’ve built an entire reporting infrastructure to avoid talking to customers. You know what device they use, what time they click, how long they scroll. You just don’t know why they left without buying. Three phone calls would tell you. Three! But that requires getting uncomfortable. It requires hearing things that might contradict your roadmap. It requires being wrong in front of people. Data dashboards let you be wrong in private. The Nike Lesson. Data Is a Voice, Not a Verdict Philip spent years at Nike learning something I’ve always believed but never had the right language for: data shouldn’t tell people what to do. It should give them another perspective to consider. He came from digital functions where metrics drove decisions. Then he landed at one of the most creative companies on the planet, where the brand was built by people who trusted their instincts. “You encounter people who built the business, who created the edge,” he said. “You show them a table of data and tell them to make a different decision than what their gut tells them. They laugh at you.” He tried everything to make them more “data-driven.” Better visualizations. More compelling presentations. Nothing worked. Until he reframed it entirely. “It was very important not to tell them what the data says, but really present the data as an additional opinion that now sits at your table. Here’s another expert opinion for you to consider.” Not mandate. Not truth. Just another voice in the room. “That changed the game quite a bit.” This is what I mean by art and science working together. The creative leaders at Nike had context Philip couldn’t see in the spreadsheet. They’d talked to the CEO, the competition, manufacturing. They had instincts built from years of making bets. The data gave them one more input. They didn’t always follow it. But now they were making better decisions because they had both the numbers and the nuance. That’s the balance. Data as perspective, not prescription. Instinct informed by evidence, not replaced by it. Your Problem Isn’t Data. It’s Courage. Most organizations don’t have a data problem. They have an adoption problem disguised as a data problem. You build dashboards. Nobody acts on them. You hire analysts. Nobody listens to them. You buy tools (moar martech!). Nobody changes behavior. And then you blame the data. “We need better attribution. We need real-time signals. We need AI to surface insights.” No. You need someone willing to make a call when the data says 75% but feels like 50%. You need someone willing to override the model when three customer conversations reveal something the algorithm missed. You need someone willing to say, “We’re moving forward with incomplete information because waiting costs more than being wrong.” That’s not a data literacy problem. That’s a leadership problem. And the organizations that win in the next decade won’t be the ones with the best dashboards. They’ll be the ones where leaders make decisions, learn fast, and iterate. Perfect data is a myth. Perfect decisions don’t exist. But courageous decisions with good-enough data? Those compound. If you’ve read this far, why not share this post with someone who might enjoy it? The Question If you had to make one decision tomorrow without perfect data, what would it be, and why aren’t you making it today? Not “what tools do we need?” Not “what’s our sample size?” What are you avoiding deciding because you’re scared? Around the Town * Holy cow, I’m running a conference… AI for GTM is a one-day experience, in Durham, NC, on December 3rd. As a Playbook Broken reader, I have a free pass for you, just ask. * Deep into Season 2 planning for Playbook Broken. We’re shifting to more collaborative problem-solving, less traditional interviews. If you’ve got ideas for guests I should talk to or topics that need dismantling, find me on LinkedIn. * Currently reading Enshittification by my actual favorite author, Cory Doctorow. What have we done, people, what have we done? * Also: Plur1bus is absolutely bonkers and worth watching. From the people who made Breaking Bad and Better Call Saul. Thanks for reading. If your playbook is cracked, we’re here to help rethink and rebuild it with you. —Marc This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    37 min
  5. Your Marketing Stack Just Became Obsolete

    11/05/2025

    Your Marketing Stack Just Became Obsolete

    Your marketing workflows are already obsolete. Amanda Cole, CMO of Bloomreach and Executive Board Member at MACH Alliance, drops truth bombs about AI, marketing's future, and why "ignorant thinking" might be your only competitive advantage. She admits what most executives won't: "I have no idea what I'm doing." Then explains why that's exactly the qualification needed to lead through AI transformation. ⏱️ KEY MOMENTS: [00:00:48] The Death of Workflows - Why everything you learned about marketing automation is wrong [00:14:45] "We Have to Unlearn What Feels Safe" - The vulnerability required to lead through AI change [00:17:28] "There Is NOT Another Option" - Why this isn't like Bitcoin or other tech hype cycles [00:21:20] The Religious Conversion Moment - When Amanda realized "the front end of technology doesn't matter anymore" [00:36:32] Why CMOs Should Celebrate Their Own Extinction - "The CMO role has been going away... I'm excited about that" This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    42 min
  6. AI Took Nate's Job

    10/21/2025

    AI Took Nate's Job

    In the latest episode of Playbook Broken, Nate St. Pierre told me, “The value of what I bring is approaching zero.” But don’t worry about Nate, he’s not panicking. He’s selling his replacement. Most consultants facing extinction would deny it’s happening. Nate built the thing making him obsolete, called it Youbots, and started selling it to small businesses for 10% of what they used to pay him. Then he took Wednesdays off. We get into a ton of stuff, including his journey into Hollywood, the future of AI and human creativity, ethical considerations, and tons more. It was a great hang and a great conversation. The Self-Automation Paradox In late 2023, Nate realized that 80% of his strategic marketing and development work could be automated. So he did what many would never consider: he sold access to his own replication. He called them “NateBots.” Each bot trained on his processes, frameworks, and tone. Clients stopped hiring him and started hiring the productized version of him. His first client dropped her $5,000-a-month agency two weeks later. “I just use bots now, and we do better work and more of it,” Nate said of what happened next. That experience isn’t a testimonial. It’s a market correction and a mindset shift. It’s another playbook breaking and being rebuilt. What Nate understands faster than most is that in a world where expertise can be encoded, ownership of the encoding becomes leverage. The Wednesday Problem What followed was a ton of learning and experimentation to get the platform dialed in and working right. The key? A contextually aware “layer” that helps businesses extract maximum value from Youbots without having to become prompt and AI experts. And because Nate is the first one to rip up a playbook, they don’t work on Wednesdays. Four people, one AI platform, and they go offline midweek. Their slogan: Work Less, Live More. It’s not a stunt. It’s the company’s thesis. “For fifty years we’ve been told technology would make us more human,” Nate says. “It’s been the opposite. We’re expected to do more with less time.” While most AI firms optimize for throughput, Youbots optimizes for absence. The deliberate creation of white space. Nate spends Wednesdays building a retro text RPG, using AI for the code so he can focus on story. It’s a small example of a larger shift: use machines to recover meaning, not just efficiency. But the open question remains: where does that line stop? When does “outsourcing the boring parts” become “outsourcing the self”? Thanks for reading Playbook Broken, now share it! What Agencies Are Missing Youbots doesn’t replace tasks. It wraps AI around an organization’s context. That means even a junior hire can generate director-level strategy in hours. Agencies still cling to the belief that consultative thinking can’t be replicated. Their clients are quietly disproving them. “The value they bring needs to change quickly,” Nate says. “All that front-end value—not all of it, but a lot—is replaceable.” Survivors won’t fight automation. They’ll wield it. The ones that don’t will spend the next two years explaining to clients why their retainers keep shrinking. The Next Curve This is what AI brings: a new spin for us to fully understand and incorporate. We’ve built powerful AI tools to extend ourselves, and are now just waking up to realize some of the tools no longer need us to function. What’s different this time is who holds the agency. Nate didn’t get replaced by AI; he licensed himself through it. To me, this is the essence of Playbook Broken, and it’s why whenever I talk with Nate, I feel energized, brave, and motivated to keep pushing forward. There is an uncomfortable lesson hiding in front of our faces. The future of creative work won’t hinge on resisting automation. Instead, it’ll depend on who owns the IP of their own replication and knowledge, and who embraces and accelerates it fastest. For Nate, selling his replacement wasn’t surrender. It is succession planning. Full disclosure, I’ve been informally helping Nate with product positioning, demos, and more. If you are interested in learning more, reach out. Thanks for reading Playbook Broken! Subscribe to receive new posts! Around the town, notes and musings: * The Diplomat (Netflix) is back, and OMG, it’s so good. We binged it while visiting Colonial Williamsburg and Jamestown this weekend, which gave us time to consider how far we’ve come as a nation. * I finished doing some Clay training as part of their “Cohort” program and learned a ton. It’s not a perfect platform, and it’s expensive, but it’s also wildly powerful and requires a new way of thinking. * AI slop sucks, but that doesn’t mean we can’t try to have some fun with it, too. MQL’s are for winners! * Leaving my role as CEO of Third Door Media has been agonizing but also exciting. It’s exactly like me to get to the top of the mountain and then look for something else to climb. I’m ramping up my consulting business and talking to some incredible people doing marvelous things. If you are interested in talking, reach out anytime. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    40 min
  7. From Broken Playbooks to Category Revolutions

    09/29/2025

    From Broken Playbooks to Category Revolutions

    For years, B2B growth felt predictable: run the demand-gen playbook, crank the funnel, and expand into new segments. But the moment you try to scale upmarket into enterprise? That deal is off. Or gets very, very tricky at best. What worked in SMB and mid-market stalls out at the top of the pyramid. Sales cycles balloon. Brand trust matters more than tactics. Buyers suddenly have committees. And the old “demand gen on repeat” playbook doesn’t just break, it collapses under its own weight. That’s where (and how) Ryan Nelsen built his career with huge success with Qualitrics, among other gigs. Ryan has lived through the transition from tools to platforms to revolutions. He knows what it takes to reinvent the playbook when your market shifts underneath you. Thanks for reading Playbook Broken! Subscribe for free to receive new posts and support the show! Your playbook is cracking, bruh On this episode of Playbook Broken, Ryan and I get into it: * Enterprise is not just “bigger SMB.” Moving upmarket requires a new sales motion, brand positioning, and organizational muscles. * Category beats features: Winners aren’t just building products, they’re reshaping industries. HubSpot didn’t just sell software; it created inbound (errr, Loop?). StackAdapt is doing the same at the intersection of adtech and martech. * Consolidation is coming: AI isn’t just another tool, it’s collapsing the Martech stack. CMOs don’t want 12-point solutions. They want unified ecosystems. StackAdapt’s growth exposes a hard truth: you can’t enterprise your way with mid-market tactics. What worked yesterday won’t get you there tomorrow. “There’s power in making sure you own a category. Double down on why it’s working, why there’s value, and stay consistent in your story.” - Ryan Nelsen Forcing yourself Five weeks into his new CMO role, Ryan shattered his femur in a wakeboarding accident. Onboarding while relearning to walk became an unexpected metaphor: leadership is about forcing yourself through reinvention, even when the playbook you relied on is gone. Every marketer clings to the illusion of timeless playbooks. But Ryan’s story is proof: disruption doesn’t schedule itself around your strategy off-site. It hits, it breaks your playbook, and it forces you to rebuild in real time. The real job isn’t running the play. It’s knowing when to burn it. Thanks for reading Playbook Broken! This post is public so feel free to share it. Around the town, notes and musings: * The latest season of “Only Murders in the Building” is a gas and features some wildly funny cameos. * I dragged myself up to Washington, DC for #GTM2025 and met some incredible people. The highlight for me was Will Guidara’s keynote. If you haven’t yet read “Unreasonable Hospitality,” do yourself and your team a favor and read it ASAP. I wrote about the keynote on LinkedIn. * I’m having fun experimenting with LLMs and came up with a pretty slick “Focus group idea,” check it out here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

    29 min

  8. 09/08/2025

    Why Brand Is Back and AI Is Forcing the Rewrite

    We all swore off brand. Declared it dead. Buried it under a decade of dashboards, funnels, and “growth hacks.” But the playbook we tried to shred is clawing its way back. And the irony? AI, the very force accelerating sameness, is pushing us to rediscover the one thing machines can’t fake: brand, story, and the human spark. My latest guest on Playbook Broken was Deema Tamimi, VP of Marketing at Creatopy, and I felt, a kindred spirit (shout out to Anne of Green Gables. If you know, you know). Deema lived through Xbox, YouTube, Flipboard, and Figma and is, like me, a non-profit veteran, where resources are razor-thin. That vantage point gave us a conversation that cut across AI, advertising, and why Don Draper might be a zombie worth listening to. As Deema put it: “There is this moment right now or this sort of zeitgeist… brands are going to basically come back to be so important.” The Death (and Resurrection) of Brand For years, marketers bent the knee to performance. Every campaign optimized, every click accounted for. Talk about brand in a room and you’d get eye rolls. Still do. Deema nailed the consequence: “We almost treated everything like a performance thing… so much of what’s been put out there looks like it was growth hacked.” Now, AI is flooding the zone with content stamped from the same mold. The sameness is deafening. That’s why the pendulum is swinging back. What stands out? A story. A voice. A moment that connects. Don Draper isn’t dead. He’s undead. And he’s here to remind us why ideas still matter. AI Years vs. Dog Years We used to joke that internet years were like dog years—seven to one. Deema went further: AI years are twelve to one. And accelerating. Deema’s point: “In a month or two months, it’s gonna be more than that. That’s what’s so unique and daunting about AI.” Speed matters. Playbooks don’t just get outdated; they disintegrate. What worked last quarter may already feel obsolete. But speed also opens a door. AI can crunch numbers at a scale that no team can match, giving marketers space to reclaim the creative muscle they lost when they went all-in on measurement. That speed isn’t just breaking playbooks. It’s rewriting how we think about advertising itself. Thanks for reading Playbook Broken! Subscribe for free to receive new posts and support my work. Nonprofits and the Grant Playbook Talking to Deema reminded me of my decade in nonprofit (March of Dimes, LLS, Autism Speaks). That nonprofit work adds another layer because nonprofits often struggle with design, storytelling, and even basic marketing. AI could change that. She reminded me of the grind of grant writing: “If you don’t get it exactly to the T, they’ll just throw out your application.” Imagine an AI partner turning that bureaucratic nightmare into a solvable task. If nonprofits can use AI to tell better stories with fewer resources, what’s the excuse for brands with entire departments? Slowing Down to Speed Up We closed on something personal. Deema shared the moment she forced herself to break her own playbook: slowing down. She’d been sprinting through meetings, tools, and metrics. Until she turned off the computer, went for a walk, and listened to Johann Hari talk about “stolen focus.” Her realization: “When I slowed down and allowed myself time to think deeply… I was way more productive. I was slowing down to speed up.” That may be the most radical broken-playbook idea of all. Not another tool. Not another test. Just space to think. Five Truths That Stuck * The brand playbook was never broken. We just stopped believing in it. * AI can crunch numbers, but it can’t create meaning. That’s our job. * Performance without story looks like everything else. * Sometimes the most subversive move is to slow down. Around the town, notes and musings: * I had the unique opportunity to attend and speak at Inbound (HubSpot’s big annual event). Beyond Amy Poehler, Colin Jost, and Glennon Doyle, my 4 colabs that focused on learning how to fight resistance and gain momentum were a gas to host and moderate. I’m doing a version of that same workshop on September 16th in Raleigh at the Triangle SEO meetup. You should totally come. * I’m doing my usual and reading too many books at once. I’m listening to Empire of AI on Spotify, and reading Impossible to Ignore and The Drawing of the Three on Kindle. * Attended my first-ever US Open and had the opportunity to see a big upset in person. #TEAMFELIX Thank you for reading Playbook Broken. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit marcsirkin.substack.com

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About

Sharp, subversive takes on marketing, AI, and business strategy. Playbook Broken includes deep dives, interviews, and bite-sized insights for people who don’t play by the rules. marcsirkin.substack.com

Information

  • Creator
    Marc Sirkin
  • Years Active
    2025 - 2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © Marc Sirkin
  • Show Website
    Playbook Broken Podcast