Making Sense of Martech

How to Be an Unhinged $1.4B Unicorn

"People respond to people. It's worked really well for PostHog to lean into the personalities of the people who build the company. We're being authentic, we're being honest, being unfiltered. And I think that's refreshing." — LottiePostHog built a $1.4 billion company on a single thesis: stop guessing, measure everything.So why is PostHog's own brand, the hedgehog, the chaos, the weirdness people fight for in Slack, measured mostly by gut feeling and good vibes?In this episode, Jacqueline sits down with PostHog's marketing lead Joe Martin and lead graphic designer Lottie Coxon to pull apart what actually makes a bold brand stick at scale. Together, they've spent years keeping PostHog weird, and they have the campaigns to prove it.This one covers brand autonomy, the real ROI of mascots, why AI has data but not instinct, what it actually costs to hire for taste, and why a data company running an A/B test on its own illustrations is both perfectly on brand and, in hindsight, exactly the wrong call.PostHog sells tools that optimize the B2B playbook. Their own brand is allergic to it.Timestamps00:00 — A $1.4B analytics company whose most-loved asset is governed by feel, not metrics.08:05 — A teacher told Lottie she wasn't good at art. That summer she practiced every day — not to prove anyone wrong, but because she discovered she could get better.09:35 — Lottie didn't iterate toward a visual ideal. She iterated toward a feeling: the hedgehog had to channel the specific personalities of the people building the company.17:20 — PostHog shipped a competitor comparison chart that crossed from knowing sarcasm into mean-spirited. Pulled within two days. Intent was right. Execution landed wrong.24:15 — PostHog's original marketing font was Lottie's actual handwriting, turned into a typeface called "Loud Noises" so the whole team could write in hedgehog speech bubbles.36:20 — PostHog's hiring test isn't about polished proposals. It's about whether a candidate can decide what to do and then actually do it.43:34 — Joe ran an A/B test replacing brand illustrations with product screenshots, found marginal differences, and concluded the test itself was the wrong call.50:28 — PostHog's brand works because it reflects the actual personalities of the people who build it. Authenticity isn't a strategy. It's what happens when you stop performing one.52:50 — AI can approximate taste but has no genuine intuition. It produces the average of everything else.57:52 — Knowing when not to measure something is a more sophisticated form of data literacy than chasing every metric.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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You're Getting Gouged on Compute with Luke Ambrosetti

2w ago00:30:02Tap to summarize

"APIs led us to data silos. MCP could lead us to context silos, and that's why I'm hoping people will be a bit more restrictive about where they hook up MCP." — LukeLuke Ambrosetti has spent a decade arguing that the data warehouse should sit at the center of every enterprise martech stack. Now, as Databricks plants its CDP flag and Snowflake expands into AI decisioning, the architecture he championed is either winning or getting absorbed into something bigger. In this episode, Luke, principal industry architect for marketing and advertising at Snowflake, joins Jacqueline to unpack whether warehouse-native has become a genuine foundation or just another vendor checkbox.They cover the full arc: why schema ownership beats security as the real argument for warehouse-native, how SaaS vendors have quietly marked up compute and resold it back to brands, and what the explosive growth of MCP servers without governance infrastructure actually means for enterprise martech teams.This is a conversation about structural power in the stack, who controls the serving layer AI operates from, and whether innovative challengers or deep-pocketed incumbents walk away with the next decade.Timestamps03:39 — Resist Buying Anything First: When building a martech stack from scratch, Luke's instinct is to resist purchasing any tool for as long as possible and start with a business conversation instead, a direct challenge to the tool-first culture of the industry.06:30 — The Warehouse as a Serving Layer for AI: Every major platform is racing to become the governed, AI-ready data layer because whoever owns that foundation wins the next generation of martech. Luke explains why that race matters more than the CDP wars ever did.09:29 — Warehouse-Native as a Checkbox Feature: Luke names the single most common architectural mistake he sees: brands going warehouse-native in name only, with vendors attaching the label without committing to the underlying architecture.11:55 — Vendors Are Gouging You on Compute: Martech vendors have historically marked up cloud compute and storage and resold it to brands as SaaS fees, and warehouse-native flips that dynamic by forcing vendors to compete on actual differentiated functionality.14:44 — Schema Ownership as the Underrated Benefit: Luke argues the most overlooked advantage of warehouse-native is not security or cost savings but owning your own definition of what a customer looks like, so you are never force-fit into a vendor's data model.17:40 — Brands Failing Publicly With AI: Luke argues that brands that experiment with AI and fail publicly deserve more credit than those that stay too conservative; visible failure is evidence of a culture willing to learn.26:40 — The Self-Referential Nature of Big AI Deals: Luke calls out the circular dynamic of major platforms paying each other billions in AI arrangements, while still affirming that real brand-level results keep him from writing it off entirely.28:30 — Who Wins, Innovators or Incumbents: Luke gives his personal read on where the real competitive advantage sits as every tool races toward becoming every other tool.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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Stop Ignoring the $1.3 Trillion Gap with Sarah Gallardo

3w ago00:52:10Tap to summarize

"If I could live through accessibility audits and not have someone say, 'but we have alt text,' I would feel like I just entered a new realm of the world." — SarahEmail accessibility (a11y) is broken, and the industry largely knows it.77% of brands say accessibility is a priority. Only 8% follow best practices. Only 0.1% of HTML emails actually meet the standard. That's not a resource problem; it's a myth problem, a status quo problem, and in some cases, a willful ignorance problem.The industry talks endlessly about inclusion while locking out 1.3 billion disabled people worldwide, who collectively control over $1 trillion in annual disposable income.Sarah Gallardo has spent over 12 years building email campaigns for Fortune 500 companies, earning her CPACC and Trusted Tester certifications along the way. She now audits enterprise email programs for accessibility, and in this episode, she brings the receipts on an industry that talks inclusion and consistently fails to deliver.Timestamps00:42 — The 77% vs. 8% Chasm: The industry says accessibility matters. The data says otherwise, and the gap isn't malicious; it's a myth. Either way, disabled users pay for it.07:15 — The $121 Billion Case: Inaccessible digital experiences cost an estimated $121 billion on Black Friday 2021 alone. The ROI argument isn't theoretical; it's already been paid for.16:45 — Why the Big Platforms Are Still Behind: Legacy code, slow feedback loops, and architecture built before accessibility was a priority. Sarah explains why the tools millions of marketers use every day haven't caught up.20:55 — AI Can't Audit This, Yet Don’t Chase 100%: 60–80% of WCAG criteria can't be evaluated by any automated checker. A perfect score from a tool isn't a finish line; it's barely a starting point.26:44 — How Misinformation Survives at Scale: At large companies, bad accessibility advice spreads quietly through dev teams. Only certifications, reputation, and leadership backing earn advocates enough authority to push back.31:00 — The Alt Text Myth That Won't Die: Alt text isn't the finish line marketers think it is. 25% of disabled users aren't using screen readers at all, including people with dyslexia, relying on tools that block images outright.38:55 — The Moment Stakeholders Stop Arguing: Nothing converts a skeptic faster than hearing a screen reader try to read a broken email out loud. Sarah's go-to move in the room.43:30 — Audits for Lawyers vs. Audits for People: Some companies run accessibility audits to build a legal paper trail, not to fix anything. Sarah's real job is turning that defensive instinct into actual change.49:30 — The Misinformation Loop Nobody Talks About: Bad accessibility advice gets copy-pasted across the industry until it's baked into real codebases, quietly undermining the very users it claims to help.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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AI Was A Waste of Time, Until It Wasn't with Megan Boshuyzen

4w ago00:47:36Tap to summarize

"You should be layering AI on top of what you're already doing to make you more efficient. It should not be doing the bulk of the work. It should just be making you faster." — MeganEmail development has long been the graveyard of good design intentions where beautiful mockups meet the harsh reality of Outlook's rendering engine, dark mode disasters, and code that would make any web developer weep. But while most of the industry gets swept up in AI hype promising magical solutions, actual email developers are quietly discovering what works, what doesn't, and what's dangerously oversold.Megan Boshuyzen, development lead at Inbox Army, brings a rare combination of technical depth and real-world perspective to the AI conversation. A graphic designer turned email developer, she's witnessed the evolution from Vertical Response in 2010 to today's complex email design systems. Her journey through MailGun, Email on Acid, and now agency-side development gives her insights few possess about where AI genuinely helps and where it spectacularly fails.This is not a hype episode. It's a field report from someone doing the work and telling the truth about it.Timestamps04:35 — AI Saved a Complex Liquid Build: When a client prohibited storing product data in a CRM, Megan used AI to work through intensive if-else Liquid logic, dynamically matching product data loaded into the email with conditional display in the ESP.06:10 — ESPs Must Own Accessibility: Email service providers and drag-and-drop editors bear the primary responsibility for making their code accessible, not individual marketers who can't edit it — and many of the required fixes are not significant engineering lifts.13:45 — The Photographer Analogy for Email Developers: AI democratizes email creation the way smartphones democratized photography, but just as professionals still get hired for what matters, skilled email developers will remain essential at the enterprise level.19:07 — Building an Email Design System at an Agency: Megan breaks down the real complexity of building a multi-client email design system at Inbox Army, why e-com layouts demand more than she anticipated, and how Claude Code is helping her manage the JavaScript as it scales.26:21 — From "AI Is Useless" to Cautiously Bought In: Megan traces her own two-year shift from dismissing AI entirely to finding genuine, specific use cases and explains why she still refuses to call it a magic bullet.36:25 — AI Creates Mediocre Code: AI accelerates the creation of mediocre email code through a lowest-common-denominator approach, similar to how engineers encounter inefficient AI-generated code solutions.44:35 — Build the Foundation Before AI: Developers who master coding fundamentals first and then layer AI on top will outlast those who build AI-dependent workflows because when something breaks, you need a foundation you actually understand.46:55 — Quietly Terrified of Code: A large, silent portion of the email and martech industry is anxious about AI and code. This episode is designed to help them feel grounded and less alone, not more panicked.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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Ticket Taker vs. Problem Solver: Be Irreplaceable with Darrell Alfonso

Jun 2400:54:52Tap to summarize

"I really think that most companies' problem isn't efficiency, oftentimes. It's just like a lack of direction, strategy, or, you know, bad leadership practices." - DarrellThis spring, commencement speakers were booed off the stage for telling graduates that AI is their future. Meanwhile, marketing ops teams are getting leaner, and job listings are down. The people who built careers on technical fluency are wondering if it's still enough.Darrell Alfonso has lived on both sides of this. He led marketing ops at AWS and Indeed, wrote the book on the field (The Martech Handbook), and built a following with his newsletter, The Marketing Operations Leader, then got laid off himself last year.In this episode, Darrell and Jacqueline pressure-test the AI-replacement narrative: what's actually driving layoffs, where AI can't replace human judgment, and why the cost-saving pitch is shakier than executives want to admit.This is the hallway conversation the industry keeps having after the conference session ends.Timestamps04:34 — AI Won't Fix Bad Leadership: Most AI use cases are internal efficiency plays. The real problem is usually a lack of direction or poor leadership, and AI can't fix that.11:50 — Elevating the Ops Professional: AI disruption changes the climate, not the mission. Great ops professionals are problem solvers first.17:03 — Layoffs Are the New Normal: Layoffs no longer signal a red flag on a resume. Hiring managers have had to catch up to that reality.23:45 — The Future of Execution Roles: AI is pushing execution-layer work up the abstraction ladder toward strategy. Ticket-takers are already being displaced.28:36 — AI Is Only Cheaper 23% of the Time: MIT found AI is only cheaper than humans for 23% of tasks. Uber's CTO burned through the entire 2026 AI budget in four months on tokens alone, and the cost story is messier than the pitch.38:42 — The Personal Cost of a Layoff: Darrell on what the layoff cost him emotionally, and how reframing it as a signal instead of a failure changed his trajectory.43:45 — Ops Is Creative Work: Ops is system design and problem-solving from scratch. That reframe changes how ops professionals should present themselves.51:28 — Golden Age or Tipping Point: Darrell's answer: tipping point. The professionals who understand both the tech and the strategy will define what comes next.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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Martech Tools Should Serve, Not Dictate with Bree Graham, ex-CashApp & Afterpay

Jun 1700:58:05Tap to summarize

Most marketing teams have more tools than strategy, and now they're layering AI on top of that mess. When you scale fast in the wrong direction, fixing it requires more than just throwing AI at your existing martech sprawl. It demands architectural thinking, data governance discipline, and genuine cross-functional partnerships that most organizations simply haven't built yet.In this episode, Jacqueline Freedman sits down with Bree Graham, who spent seven years leading growth and marketing platform transformation at Afterpay, designing the composable infrastructure that powers engagement and retention across a multi-brand global system. Bree scaled Afterpay from siloed, manual execution to hundreds of millions of hyper-personalized customer communications per month.From AI decisioning that broke every hypothesis her team had to why procurement might be your most underrated strategic partner, Bree makes a compelling case that the stack mirrors the org chart, and until you fix the ownership problem underneath, no tool can save you. This episode is equal parts architecture lesson and leadership playbook.Timestamps05:12 — AI Should Be Invisible: AI shouldn't be a buzzword in every conversation; it should be embedded deeply enough in the product that you never need to mention it. The real test is whether the functionality speaks for itself.11:00 — The Best Martech Leaders Were Marketers First: The sharpest martech leaders have lived on the marketing side first. They relate to the full customer journey and bridge tech architecture with real campaign needs.20:52 — AI Found What We Missed: When Bree's team fed lifecycle data into an AI decisioning model layered on their warehouse, the outputs broke from their original hypotheses because the model had context their CRM tools never did.27:43 — Who Owns the Connective Tissue? The hardest unsolved question in AI-augmented martech isn't which tools to buy. When it's unclear who's accountable for making sure they work together, integration silos form by default.39:12 — Data Governance Belongs Everywhere: Governance-first thinking shouldn't be reserved for regulated industries. Any brand that collects customer data has a privilege and a commitment to protect it, whether you’re in finance or fast food.46:43 — The Power of Saying No to Vendors: A healthy vendor relationship requires the ability to say no.50:52 — It's Not About the Tool: A tool can be excellent and still wrong for the job if it doesn't serve the experience you're building. The question is never which tool is best; it's what system best serves your customer.53:29 — Tools Should Serve You: For years, vendors dictated how teams used their tools. Composable architecture flips that marketers now make tools conform to their business, not the other way around.SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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It's Just Marketing Ops With Better PR with Sara McNamara

Jun 1001:05:53Tap to summarize

"SaaS companies are systematically undervaluing marketing ops professionals by rebranding their work with trendy titles while taking their contributions for granted until everything breaks.” — SaraSara McNamara has spent her career building go-to-market systems at companies like Slack, Salesforce, and Cloudera, the unglamorous, essential work that makes revenue teams actually function. As the revenue operations and go-to-market lead at Vector, she has a thesis about where ops is headed that challenges how many see their own roles. While AI rewires what ops teams actually do, she argues that strategic operations practitioners aren't becoming obsolete, they're becoming more essential than ever before.In this wide-ranging conversation, Sara unpacks the marketing ops erasure problem plaguing SaaS companies, explains why attribution will never be a perfect science, and shares specific AI workflows that are actually working in her day-to-day operations. She makes the case that ops professionals need to upskill now or risk having engineers and upskilled marketers fill the strategic vacuum they leave behind.Timestamps03:45 — Building Ops at Vector: How Sara approaches go-to-market operations at a Series B company and the unique challenges of scaling ops infrastructure07:20 — Career Journey Through Big Tech: From Slack to Salesforce to Cloudera, the lessons learned building revenue systems at enterprise scale10:15 — Marketing Ops Erasure Problem: SaaS companies are systematically undervaluing marketing ops professionals by rebranding their work with trendy titles while taking their contributions for granted until everything breaks18:25 — Ops Must Upskill or Lose Ground: Operations professionals need to actively learn AI tools now, or risk having engineers and upskilled marketers fill the strategic vacuum they leave behind19:15 — AI Pricing Will Follow Uber Model: AI companies will likely subsidize usage initially to create dependency, then dramatically increase pricing once users are locked in37:53 — AI as Data Hygiene Assistant: Use AI for observability and anomaly detection in your CRM rather than giving it permission to make changes45:30 — Ops More Essential Than Ever: While there's consolidation pressure in ops, strategic ops practitioners who act as the 'adult in the room' for go-to-market are becoming more valuable, not less59:00 — Attribution's Real Purpose: Attribution should be used directionally for channels and campaigns, not as a perfect science01:02:40 — AI Will Amplify Marketing Chaos: AI will create more marketing 'slop' and turbocharged outreach, making attribution even murkier while elevating the importance of relationships and event marketingSponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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Why Scott Brinker Says AI Can't Pick Your Tech Stack

Jun 300:34:53Tap to summarize

"Most of marketing is not a verifiable domain. You can't outsource it to the agents. You need the humans." - Scott BrinkerScott Brinker, creator of the Martech landscape and former VP of Platform Ecosystem at HubSpot, joins Jacqueline for a no-holds-barred conversation on AI's real limits in marketing, and why the industry's confidence in what AI can do may be its biggest liability. This is a genuine stress test of some of marketing technology's most popular assumptions: that AI can replace human judgment in vendor selection, that content governance is someone else's problem, and that consolidation is always the safe bet.The episode opens on the concept of synthetic certainty: AI outputs that feel authoritative but can't actually be validated, and builds from there into a broader argument about why marketing, as a non-verifiable domain, is more defensible than people fear. Scott draws a sharp line between tasks AI can handle reliably and decisions that require taste, context, and stakes. The stakes get real when he calls out the single most dangerous assumption in martech right now: that full-stack consolidation is the goal. Spoiler: handing your entire marketing operation to one vendor isn't simplification. It's surrender.Timestamps00:57 — Synthetic certainty unpacked: why marketing is not a verifiable domain like software engineering and what that means for job security04:57 — Where AI actually breaks down: a vendor evaluation scenario and why attribution models are "delusional"12:33 — The AI content governance gap: 103 of 163 respondents doing zero verification, and whether this becomes an industry credibility crisis22:59 — The three-bucket theory of marketing roles and which bucket AI is about to crush entirely26:42 — The most dangerous assumption Martech operators are making: why full vendor consolidation is a trap, not a goal33:46 — Seventeen years of mapping the landscape: what the 2011 version of Scott would find shocking about vendors, brands, and the future of martech researchSponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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Why Everyone in Martech Feels Behind Right Now with Scott Brinker

May 2700:40:09Tap to summarize

"Content was king. Now context is the monarch." — Scott BrinkerScott Brinker has been mapping marketing technology longer than most practitioners have been in it. In this Hot Seat episode, Jacqueline puts the godfather of Martech in the chair to pressure-test the 2026 State of Martech Report, and what emerges is a surprisingly honest reckoning with where AI in marketing actually stands. The landscape has hit a historic plateau, the stack is stratifying into competing gravitational layers, and the organizations holding it all together are marketing ops teams that didn't sign up to be system administrators in the first place.The conversation moves from the chrysalis metaphor anchoring this year's report – AI everywhere, integrated nowhere, necessary mess – to the bifurcation Scott predicts between infrastructure consolidation and an explosion of ephemeral, app-like software. From content marketing's category collapse to Salesforce and HubSpot's reluctant pivot to headless architecture, this episode maps the strategic fault lines every B2B and B2C martech practitioner needs to understand. It closes on a tension Scott can't fully resolve yet: synthetic certainty, and why the most dangerous problem in the stack may be the one nobody has named.Timestamps02:05 — Rapid fire: first martech tool, what's overrated, and one word for martech in 202609:12 — AI everywhere, integrated nowhere: the chrysalis metaphor and the messy middle16:10 — The landscape plateau: less than 0.1% growth after 15 years of expansion: pause, peak, or bifurcation?21:00 — Content marketing's category collapse and why the first wave of AI-native tools was always going to burn fast27:19 — Pace layering, composability, and how to make stack decisions when the ground won't stop moving32:56 — Stack stratification: the battle for the center of gravity between SaaS incumbents (Salesforce + HubSpot), data warehouses, frontier labs, and the multi-front war for the center of gravity38:14 — MCP's rise and the governance problem nobody is solving yet44:44 — Synthetic certainty and the unnamed problem to be discussed in Part 2SponsorBrought to you by Hightouch, the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at hightouch.com/msom.Brought to you by Bloomreach’s Innovation Fest on June 3. A 60-minute live virtual event built around one idea: value before volume. While the rest of the market races to announce more AI agents, they're making the case for fewer, better ones — agents actually held to a standard of moving revenue numbers. Worth attending if you're tracking where agentic AI in commerce is actually going. Sign up here!Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.

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