Playbook Broken Podcast

About Playbook Broken Podcast

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 (https://marcsirkin.substack.com?utm_medium=podcast)

Publisher

Marc Sirkin

Category

business · technology

Language

en

Explicit

No

First episode

17 Apr 2025

Latest episode

6 Jan 2026

Latest episodes

16 episodes in the feed.

1. 

   6 Jan 2026

   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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

2. 

   10 Dec 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 (https://chiefmartec.com/2013/06/martecs-law-technology-changes-exponentially-organizations-change-logarithmically/) 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 (https://martech.org/the-cdp-fantasy-is-over/) 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 (https://www.amazon.com/Fall-Dodge-Hell-Neal-Stephenson/dp/006245871X) 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

3. 

   14 Nov 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 (https://www.linkedin.com/in/philipjarmstrong/) 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 (https://www.eventbrite.com/e/ai-for-go-to-market-gtm-tickets-1967729360487) 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 (https://www.linkedin.com/in/marcsirkin/). * Currently reading Enshittification (https://www.versobooks.com/products/3341-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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

4. 

   5 Nov 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

5. 

   21 Oct 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 (https://youbots.ai/), 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 (https://www.clay.com/university/cohorts)” 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! (https://www.linkedin.com/posts/marcsirkin_gtm-sales-marketing-activity-7384636280111788034-5zlV) * Leaving my role as CEO of Third Door Media (https://marcsirkin.substack.com/p/if-youve-ever-led-through-chaos-you) 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

6. 

   29 Sept 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 (https://www.linkedin.com/posts/marcsirkin_gtm2025-activity-7377329865890500608-bGi9). * I’m having fun experimenting with LLMs and came up with a pretty slick “Focus group idea,” check it out here (https://www.linkedin.com/posts/marcsirkin_ai-focusgroup-gtm-activity-7377711133622738944-mim8). 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

7. 

   8 Sept 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 (https://www.inbound.com/) (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. (https://www.meetup.com/triangleseomeetup/events/310614036/) * 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 (https://www.usopen.org/en_US/news/articles/2025-08-30/felix_augeraliassime_upsets_alexander_zverev_with_2025_us_open_masterclass.html) 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

8. 

   24 Aug 2025

   The Funnel is DEAD. Pipeline is a Lie. SaaS is Next.

   If you're still bragging about MQLs, SQLs, and pipelines, Sangram Vajre (https://www.linkedin.com/in/sangramvajre/) thinks you should be fired. If you're still running 20-step nurture campaigns, he thinks you're stuck in 2012. And if you're still clinging to a SaaS business model? He says you're the next Blockbuster. According to Sangram, the sacred cows of marketing are getting slaughtered, and it's about damn time. In this episode of Playbook Broken, Sangram Vajre (co-founder of Terminus, GTM Partners, and author of MOVE) didn't just challenge the status quo, he torched it. What emerged from the ashes is a blueprint for what comes after the funnel, after pipeline worship, and after SaaS itself. Spoiler alert: Most of us are still fighting yesterday's war with tomorrow's buyers. Thanks for reading Playbook Broken! This post is public so feel free to share it. The Funnel Fantasy is Over Remember when drip campaigns worked? When buyers politely followed your 12-step nurture sequence like good little prospects? When organic reach on social media was a thing? Today's buyers don't drip. They binge. They see something interesting, research everything available, and often make decisions within 24 hours. They leverage SEO, GEO, Reddit, and their own networks of contacts. Sangram told me a story that should terrify every marketer still obsessing over pipeline volume: A CMO proudly posted on LinkedIn about generating $20M in pipeline. The comments were full of fire emojis and "crushing it" reactions. A week later? She was fired. Why? Because pipeline volume divorced from business outcomes is just expensive theater. If it's not tied to customer retention, net revenue retention, or profitable unit economics, it's vanity wearing a business suit. "Pipeline without profit is just activity," Sangram explains. "And activity without outcomes is what gets you replaced." Stop celebrating how much pipeline you've "generated." Start asking whether it's the right pipeline. GTM Doesn't Belong to Marketing Here's where things get uncomfortable for everyone involved with and responsible for driving revenue. Sangram and his team interviewed dozens of C-level leaders. The pattern was brutal: * Every CEO said: "I own go-to-market." * Every CMO and CRO said: "I'm not sure who owns it." That disconnect is killing companies. Go-to-market isn't just campaigns or product launches. It's the entire business strategy. Where to expand geographically. What products to build next. Which companies to acquire. That's CEO-level decision making, not departmental execution. In my own experiences, this rings incredibly true. Third Door Media has run hundreds of lead generation, brand, and activation campaigns for companies large and small We consistently get the sense that internal silos are creating challenges for how our customers are executing their GTM efforts. In the past few months, I’ve spoken to multiple executives about disconnects between marketing automation platforms and sales-owned CRMs, between departments, and in messaging disparities that confused and confuddle prospects and customers. Teams may mean well, but too many of them are operating in silos, using vanity metrics and not focusing on the business, as Sangram points out. Thanks for reading Playbook Broken! Subscribe for free to receive new posts and support my work. SaaS is the New Blockbuster If that wasn’t enough fire, here’s where Sangram went nuclear. The SaaS model, with $100K annual contracts, multi-year lock-ins, and armies of SDRs cold-calling, is cracking under its own weight. Why would any CEO sign a 3-year deal for software they might not use, then hire staff just to operate it? Instead, smart leaders will pay $10K/month for services that deliver guaranteed outcomes. Software becomes the invisible backend. Services become the customer-facing front. "The future isn't Software-as-a-Service," Sangram predicts. "It's Services-as-Software." And most SaaS companies are about to get Netflixed. Breaking Your Own Playbook If your marketing teams are still worshiping the funnel and bragging about MQLS, it’s time to wake up. To some (and believe me, I get it), it still feels safe because it once worked. But safe is what gets you disrupted. Sangram's challenge to every leader reading this: Kill the funnel. Stop bragging about pipeline. Think like a business owner, not a marketer. Admit when ego is driving your decisions. Because in the end, the only playbook that matters is the one that works for the buyers you have today, not the ones you had five years ago. Want more conversations that challenge everything you think you know about marketing? Subscribe here on Substack and watch the full episode where we torch the playbooks that no longer work. Around the town, notes and musings: * I’m reading Salt: A World History by Kurlansky, and it’s honestly fascinating. Many of the lessons apply to modern-day GTM. For example, distribution beats product. Just like SaaS founders today obsess over features, while Sangram reminds us that GTM is the business itself. * What do you call a “Swifty” that gets 3 out of 15 in Name That Tune? My daughters would have gone 15/15 and will be shamed forevermore (see what I did there?) Who’s ready for T12? Anyone buying her limited edition cassettes? Talk about a unique GTM approach. She’s a master. * I’m thinking a lot about adaptive reluctance as I plan a workshop I’m doing at Inbound Sept 3-5 in San Francisco. If you're going, look me up, let’s get coffee. Better yet, attend one of my 4 “colabs!” Thanks for reading and watching 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

9. 

   13 Aug 2025

   Playbooks Don’t Scale. Frames Do.

   We’ve spent the last decade duct-taping marketing tech stacks together, trying to run faster while seeing less. Every quarter, someone yells, “We need a better playbook!” But what if the playbook was never the problem? The frame’s freaking busted, bruh. In this episode of Playbook Broken (S01E05), I talk with Ed See, Chief Growth Officer at Zeta Global and a former McKinsey partner who has advised the world’s top CMOs. Ed doesn’t just look at marketing data; he weaponizes it. And what he says will either punch you in the gut or wake you up: “The job of marketing is to deliver profitable customers. That’s the frame. Everything else? Tactics.” Playbooks are great for scale, until the world changes. And guess what? The world has most certainly changed. Search is different. Personalization is different. Measurement is different. The buyer journey? Shattered. AI isn’t just a new tool; it’s new physics. Old systems built for linear funnels and static dashboards can’t keep up with real-time learning loops, autonomous agents, and precision at scale. It’s a good bit of madness right now, innit? The result? Most marketing orgs are still optimizing for the wrong outcome. They're running the play instead of remembering why they’re on the field. In this conversation, we break down: * The three R’s of modern marketing: Recognize, Reach, Relevance * Why AI makes old attribution models meaningless * How to future-proof your org with frames that outlast tools * The CMO’s new mandate: befriend your CFO, fast Ed also drops what must be the hottest, most dooziest take on Playbook Broken yet: “I didn’t get into marketing to be sexy. I got in to clean up waste. Marketing is a waste management business.” If that line doesn't mess with your head a little, you’re not listening hard enough. Thanks for reading Playbook Broken! Subscribe for free to receive new posts and support my work. Around the town, notes and musings: * I’ve been thinking a lot about frame vs. function, especially in brand messaging. If you can’t say why your company exists in under 10 words, you probably don’t have a real frame. Cough, cough: Third Door Media connects brands to marketing buyers. Check! * 12. Amiright? If you know, you know. * Over on MarTech.org, we’re testing “MarTech Live!” (most) Fridays. Casual, fast, and full of unfiltered takes. Join us. (https://www.youtube.com/playlist?list=PLKMjqoaBW16WK9-ZoNJssTkUViCO06dxa) * We scrambled and pulled off a terrific Live with Search Engine Land featuring some of the brightest, best minds in SEO and AIO. Check it out here. (https://searchengineland.com/seo-geo-generative-ai-future-search-engine-land-live-460481) * I’m halfway done reading Harold S. Kushner’s “Conquering Fear: Living Boldly in an Uncertain World,” which is both scary and incredibly empowering. * Mickey 17 is one hell of a watch. 5 stars, would watch it again. Thanks for reading and watching Playbook Broken.If your playbook is cracked, we’re here to help break it wide open. Thanks for reading Playbook Broken! This post is public so feel free to share it. 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

10. 

    3 Aug 2025

    The internet’s unspoken deal is DEAD.

    For 20 years, we operated under an unspoken agreement: create great content, get traffic in return. That deal is dead. Search engines built billion-dollar empires on it. Publishers structured entire business models around it. But now, LLMs are devouring content, serving up answers, and bypassing the creators who made them. Referral traffic is falling off a cliff. The old “SEO-for-traffic” equation isn’t just eroding — it’s being rewritten in real time. AIO? GEO? SEO? Regardless of what we end up calling it, this is disruption in real time. But this shift isn’t limited to media. It’s a direct hit to the way businesses build, manage, and scale their playbooks. You know the ones. Those frameworks and formulas were designed to deliver predictable results, but AI doesn’t care about your playbook. The cycle time between “best practice” and “obsolete” has shrunk from years to months, sometimes weeks. In some cases, overnight. In this episode of Playbook Broken, I talk with Will Allen, VP at Cloudflare, to unpack this collapse. Will’s not just another exec waving an AI banner. He’s on the frontlines, building products that challenge how content creators and AI companies interact — and more importantly, how value will be exchanged in the future internet. We talked about why repetition is a leadership superpower, how AI agents will outnumber human users, and why blocking crawlers isn’t a strategy — it’s a countdown clock. If you’re still measuring success by pageviews, or if you think your current playbooks will carry you through the next cycle of AI-driven disruption, you need to hear this conversation. The deal has been broken. The question is — what are you going to do about it? Thanks for reading and watching Playbook Broken! Subscribe for free to receive new posts and support my work. Around the town, notes and musings: * I'm still experimenting with TikTok (https://www.tiktok.com/@playbookbroken). I've been told my vids are good, but they need work. “Mid,” as the kids say. Or in other words, “6-7.” * I’m reading The Dutch House (https://www.npr.org/2019/09/23/762888874/motherless-children-make-their-own-family-in-the-dutch-house) by Ann Patchett not only because she’s amazing (she is!) but because when my daughter gives me a book recommendation, there is a reason. It’s so good. * Over on MarTech.org we’ve been trying a live stream on Fridays to talk marketing, martech, and to connect with smart people. Check out the episodes (https://www.youtube.com/playlist?list=PLKMjqoaBW16WK9-ZoNJssTkUViCO06dxa) and clips on the YouTube channel. * If you have read this far, let me just say “Thank you” and that I hope you are safe and okay. 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

11. 

    20 Jul 2025

    The Playbook Is Dead. Long Live the Feedback Loop.

    That’s the biggest takeaway from my recent conversation with Zach Vidor, CEO of Octave, on Playbook Broken. We covered a lot of ground, but one theme kept circling back: the old go-to-market (GTM) playbooks aren’t failing because they were bad. They’re failing because the game changed, and we’re still pretending the field looks the same. Octave’s philosophy that “outbound isn’t broken, your playbook is,” isn’t just a cheeky line. It’s a diagnosis. The explosion of generative AI, the collapse of traditional moats, and the accelerating entropy in tech markets have outpaced how most companies align teams, build messaging, and respond to signals. Zach calls it Generative GTM — a rethink of how core messaging, ICP definition, and positioning are created, not just executed. The goal isn’t automation. It’s contextual intelligence. An always-on feedback loop between what you say, who hears it, and how they respond. A few things stuck with me: * Growth isn’t easy — and never will be. The promise of “easy button” AI is seductive, but dangerous. Strategy still matters. Judgment still matters. And storytelling? Still king. Growth is harder than ever. Get over it. * The battlefield has shifted. Feature moats are gone. Everyone has access to the same code, same tools, same speed. Your story, how you explain what you do and why it matters, is now the primary differentiator. * Marketing and sales must operate like SEAL Team Six. No more annual kickoffs with quarterly updates. We need integrated, real-time feedback loops across the funnel. A single, fluid team. Get it together, people! * Metrics don’t tell the full story anymore. Execs don’t need more dashboards. They need synthesized signals: what personas care about, how narratives are landing, and what needs to change. And they need it fast. This isn’t about hype. It’s about adaptation. Most companies still measure the world with yesterday’s tools, while their buyers move faster, are harder to reach, and expect more precision. If we want to survive the coming wave of agentic workflows, synthetic buyers, and infinite niche competition, we can’t just retool the old playbook. We have to rebuild the operating system. And we have to do it now. Curious to hear your take: Are you seeing the same breakdown in traditional GTM mechanics? What’s your version of “SEAL Team Six” internally? #marketing #sales #ai #gtm Thanks for reading Playbook Broken! I’d be ridiculously grateful if you shared it. Playbook Postscript * This is season 1, episode 4 of Playbook Broken, a part of MarTech.org and republished here on my personal Substack. Portions of the post were created through Human-AI collaboration, and the episode was recorded in Vimeo and edited (by me, a human!) in Descript. * I’m doing an experiment in storytelling on TikTok (https://www.tiktok.com/@playbookbroken) and LinkedIn (https://www.linkedin.com/in/marcsirkin/recent-activity/all/), find me there and see what I’m up to. I’m having fun with it. 10,000 hours, right? * Here are some book, TV and music recommendations: * Book: The Children of Húrin (https://bookshop.org/p/books/the-children-of-hurin-j-r-r-tolkien/9106332?ean=9780618894642&next=t&utm_source=google&utm_medium=pmax&utm_campaign=gift_cards&utm_content=6443417794&gad_source=1&gad_campaignid=16235479093&gbraid=0AAAAACfld41NsuiKw10XtXObbDdy750Ol&gclid=CjwKCAjwp_LDBhBCEiwAK7Fnkg-sLw7uDAW1vqMRbhlaGFseykzWVN85BIG1xhgKPZmQNktnn59xNxoCInQQAvD_BwE) is one of the three 'Great Tales' of the Elder Days from J.R.R. Tolkien's The Lord of the Rings universe. This book takes place in Middle-earth thousands of years before the events of The Hobbit and The Lord of the Rings, and was a ton of fun to read. * Book: Do not sleep on reading Orbiting the Giant Hairball (https://bookshop.org/p/books/orbiting-the-giant-hairball-a-corporate-fool-s-guide-to-surviving-with-grace-gordon-mackenzie/12814980?ean=9780670879830&next=t), which is not to be missed. It’s a joyful, frustrating, and important book for anyone seeking to live a creative professional life in a big corporation. I wrote about it on LinkedIn, but the algorithm didn’t love my post, and no one saw it. Here’s your chance. (https://www.linkedin.com/posts/marcsirkin_my-new-friend-myriam-jessier-suggested-i-activity-7349887858893025280-PeJr?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAAEH8IBwcpVmGhZmlz6dWl3DIEVNu5JK2g) * TV: The Gilded Age is deliciously ridiculous and fun. Carrie Coon reading a dictionary would interest me at this point. * Music: I’m told the new Justin Bieber album is good but I haven’t tried it. Instead, I’m hooked on the 502s (https://open.spotify.com/artist/4sIuoDOzSlBqeiNJl631zX?si=Hg9SpP1VQPWIxF3kag1FDA). Thanks for reading Playbook Broken! Subscribe for free to receive new posts! 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

12. 

    13 Jul 2025

    Playbook Broken Season 1, Episode 3: Hyper Adaptive

    In this episode, we dive headfirst into the rapidly changing landscape of marketing, driven by AI and automation. Featuring Melissa Reeve, a 25-year marketing veteran and co-founder of the Agile Marketing Alliance and Marketing Frontier.ai, the conversation explores the concept of 'Hyper Adaptive' organizations. Melissa discusses her upcoming book, organizational restructuring, and the need for dynamic governance over static playbooks. She also shares insights on the importance of AI literacy, social learning, and how to prepare for an AI-native future. Tune in to uncover how leaders can navigate this chaotic yet exciting new world. 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

13. 

    18 Jun 2025

    The Search Traffic Playbook Is Dead. Now What?

    For years, the SEO game rewarded volume. Loosely researched blog posts. Light rewrites of existing content. Top-10 lists with no real perspective. That era is over. On Playbook Broken, I talked with Matthew Kay, Head of Search at ActiveCampaign and one of the creators of the Tech SEO Connect (https://www.techseoconnect.com/), about what’s breaking in search and why traffic is drying up across the board. “You go look at the traffic of some of these sites… one click in 90 days. It might be indexed. But no one’s reading it.” We covered the slow death of MQLs, the false promise of performance marketing, and why SEO might’ve always been more brand than funnel. The new playbook? Start with a strong point of view. Create for humans. Build outside of Google. And stop doing work no one will ever see. I’m a week behind and about to fall even further behind… but worry not, followers, more content is on the way! 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

14. 

    5 Jun 2025

    Social Selling, AI Sanity, and the Death of the Marketing Middleman

    If you’re still trying to sell the way you did five years ago, here’s the truth: you’re not just out of touch. You’re in the way. In this first episode of Playbook Broken, I brought on one of the sharpest minds I know. She’s a creative strategist, media whisperer, and ex-AI skeptic turned power user. My guest is Molly St. Louis, co-founder of Mosaic Group Media. Molly doesn’t pull punches. She also doesn’t waste time defending broken tactics. Molly brought real talk, sharp takes, and challenged me to rethink a few things myself. What We Got Into: Social Selling Isn’t About You AnymoreMolly laid it out: buyers want real talk, not sales decks. They’re gathering in private communities — and they don’t want marketers in the room. As someone who’s built their career in B2B, this hit me hard and true. “I want to talk to a real customer. And no, you can’t be there.” That’s what today’s buyers are saying. They want access to people like them, not polished pitches. Communities are winning because they’re honest. Your job? Learn to influence without inserting yourself. Brand Has Been Beaten to Death by Performance MetricsWe talked about how brand has gotten swallowed up by metrics and why that’s a mistake. ChatGPT didn’t flatten your voice. You did. You did it by feeding it the same stuff everyone else did. The fix? Treat brand like what it really is: a reputation insurance policy, not just a pretty logo or a top-of-funnel tactic. AI Can’t Think for You. But It Can Punch You in the Brain.Molly was skeptical about generative AI. So was I (just a bit). But she forced herself to dive in and came out on the other side smarter, sharper, and more efficient. Now she uses AI like a mirror and a mental sparring partner. Also, she made a collage of ChatGPT smoking a joint made out of The New York Times. That pretty much says it all. Five Truths That Stuck With Me: * Communities are the new sales decks. * Thought leadership isn’t about being known. It’s about being different. * Brand without teeth is just a press release in a $10,000 suit. * AI won’t kill your job. Your sameness will. * Talk like a person. People are tired of being pitched at. Guest Link:→ Molly St. Louis / MosaicGroupMedia.com (https://mosaicgroupmedia.com) Talk to me! What part of your playbook is broken? What’s the most human thing you’ve seen in marketing this year? Drop a comment or hit me up on LinkedIn (https://www.linkedin.com/in/marcsirkin/). Playbook Broken is a MarTech.org (https://martech.org/topic/conversations-with-martech/) production. 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

15. 

    29 Apr 2025

    Barcelona Broke Me Free. Outsourcing Your Imagination

    Snatching my wallet back in Barcelona — and what it taught me about complacency. Building from scratch at the Semrush AI Hackathon. Why executives must stop outsourcing their imagination. Lessons from friction, failure, and unexpected wins. How curiosity, not strategy decks, fuels real innovation. First-place finish, but a bigger personal victory. The future belongs to builders. Here’s how I rejoined them. 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

16. 

    17 Apr 2025

    Creative Play in the Digital Sandbox

    Those AI-generated figurines flooding your feeds? I think they're vital. When we prompt, manipulate, and iterate on these digital sculptures, we're not just creating tchotchkes, we're building mental models of AI behavior. It's finger-painting with neural networks. Messy but developmentally essential. Yes, they're overhyped and derivative. But dismissing them misses the forest for the AI-generated trees. Like toddlers stacking blocks before designing architecture, we're developing AI literacy through play. My hot take? Make your figurines unapologetically. This seemingly shallow pool is where we're learning to swim in the sea of generative AI. Here’s one of many variations of this prompt you can try out: Create a realistic, modern action figure of me (YOUR NAME HERE!) based on everything that you know about me from our previous conversations, sealed in its original packaging. The action figure should look like a toy with clearly visible plastic joints, slightly exaggerated proportions like classic action figures, and realistic facial features resembling me. The packaging design should be bold and colourful, with clear text and fun descriptions that reflect my personality, profession, and skills. Include 2 or 3 small accessories that match my daily work or hobbies (e.g., laptop, microphone, coffee mug). Make sure the packaging includes my name, a catchy, age rating, and playful copywriting on the box that reflects who I am. The entire image should look like a product photo of a sealed toy, clean and well-lit, with the full figure and accessories visible inside the plastic casing. You SHOULD experiment with this, change it, mold it, and play with it! 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 (https://marcsirkin.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

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