Train The AI To Recommend You – with Andy Crestodina | S6 E35

Send us Fan MailAI is quietly rewriting the rules of marketing, not by “changing SEO” but by changing how buyers choose. When a chatbot can shortlist vendors in a single conversation, visibility is no longer the finish line. Recommendability is. I sit down with Andy Crestodina, co-founder and CMO of Orbit Media, to unpack what it takes to earn AI recommendations and what most brands are missing when they chase rankings without understanding the visitor. We get practical about how AI search optimization is really the overlap of SEO and conversion rate optimization. Andy explains why prompts are longer and more personal than classic queries, how that extra context reveals real decision criteria, and why your website still matters because it is the place you control the depth, proof, and sales answers. We also dig into why AI-sourced visitors can be far more qualified, why traffic growth is a shaky North Star, and how to stop being silently excluded by publishing the questions prospects actually ask before they will take action. Then we go deeper on content strategy in an era of infinite “average” content. Andy makes a clear case for the formats AI cannot truly replicate: thought leadership with a strong point of view and original research rooted in real data. We also talk prompt engineering maturity, from ad hoc prompts to reusable prompts to custom assistants and tools, and what separates the revenue accountable CMO from someone who just manages AI outputs. This episode was recorded through a Descript call on August 3, 2026. Read the blog article and show notes here: https://webdrie.net/train-the-ai-to-recommend-you-with-andy-crestodinaIf you care about B2B marketing, lead generation, buyer intent, and building a brand that gets chosen, this one will sharpen your playbook. Subscribe, share this with a marketer who needs it, and leave a review with your biggest takeaway...........................................................................Metricool is a new official podcast partner of Web3 CMO Stories in 2026. Metricool helps marketers and creators bring structure, clarity, and consistency to their social media workflows through analytics, planning, and reporting. Listeners can try Metricool Premium for free for 30 days using the coupon code JOERI.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailInstitutions finally got their Bitcoin ETFs, then many proceeded to buy the top and sell the bottom. That one detail says a lot about how unprepared “professional” money can be in a cyclical crypto market and why investors need a better model for crypto wealth management than a couple of regulated wrappers.I’m joined by Frank Hepworth, founder of New Market Trading, who went from advising major crypto exchanges inside a top securities law firm to building an on-chain digital asset management approach where clients keep custody of their own funds. We break down the three tiers most people confuse: big banks with limited offerings, crypto exchanges with broader access but still mostly off-chain, and the blockchain layer where the full on-chain economy actually lives. If you’ve wondered why tokenized real world assets and tokenized stocks haven’t shown up in your portfolio, Frank’s answer is blunt: tokenization is not the real bottleneck when your investment account still runs like a private spreadsheet.From there we get practical about infrastructure: account abstraction, programmable investment accounts, and how limited permissions can let you combine self-custody with professional management. We also talk regulation and mandates, why institutions wait for products like the Bitcoin ETF, what investors miss when they stay passive, and how to think about scams, transparency, and third-party audits in a world full of hype.This episode was recorded through a Descript call on July 27, 2026. Read the blog article and show notes here: https://webdrie.net/your-assets-went-on-chain-your-account-didntIf you want a clearer view of on-chain investing, tokenized assets, and the future of programmable finance, listen now, then subscribe, share the episode, and leave a review to help more people find the show........................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailYou can chase every new AI tool on the timeline and still end up further from what your customers actually want. After going back to a 2019 interview with Canva Co-Founder & CEO Melanie Perkins, I’m struck by how little the core principles have aged and how much they explain the best AI products and the best marketing today.We talk about Canva’s vision of helping people take an idea and turn it into a finished design with as close to zero friction as possible, then connect that directly to what generative AI is supposed to deliver: intention to outcome, not more dashboards. From there, we unpack one of Canva’s most important values, "make complex things simple," and why it’s becoming the dividing line between AI that feels magical and AI that feels like homework. If your customer needs a 20-minute explanation to understand your value, we explore why the problem may be your story, not their attention span.Then we go deeper into something most growth teams avoid saying out loud: incentives. When a platform succeeds, do its users succeed too, or do their goals start to diverge? We look at alignment, community, trust, and why this question is becoming unavoidable across social media, creator ecosystems, and AI platforms. We close with the quote that still sticks with me years later: "You can only grow as big as your dreams," but you also have to take the first small step, then the next.If you care about AI marketing strategy, product philosophy, and building brands that last, subscribe, share this episode with a friend, and leave a review. What’s one principle you want to keep stable while everything else changes?This solo episode was recorded via  Descript on July 26, 2026. It also includes audio from my interview with Melanie Perkins, recorded on November 5, 2019, during Web Summit in Lisbon.Read the blog article and show notes here: https://webdrie.net/canva-co-founder-ceo-melanie-perkins-you-can-only-grow-as-big-as-your-dreams.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailMost founders do not “build something no one wants” on purpose. The more painful truth is that a lot of smart, hardworking people build something useful, then watch it stall because the market never hears the story in a way that makes action feel obvious. Anna Bravington joins me to unpack the real reasons products do not sell and how to fix them without panic-rebuilding everything from scratch. We walk through Anna’s simple diagnostic of three leaks: offer, visibility, and clarity. If you are getting attention but no sales, clarity or offer is often the culprit. If no one is finding you, visibility is the job. We talk about how to use data, customer interviews, and lost-deal follow-ups to locate the real blockage, and why founders need to distance their ego from their product so feedback becomes useful instead of personal. We also zoom out on competition: your rivals are not just direct competitors, but also imperfect workarounds and the biggest competitor of all, doing nothing. Then we get into AI voice-of-customer research and synthetic customers: where AI can surface language and insights humans miss, and where it can turn into a convincing echo chamber if your prompts bake in assumptions. We finish with a theme that hits home for a lot of technical and introverted builders: visibility feels uncomfortable, but hiding is often the fastest route to failure. Anna shares practical advice on becoming comfortable with being uncomfortable, and how accountability and community can make the hard parts doable. This episode was recorded through a Descript call on July 17, 2026. Read the blog article and show notes here: https://webdrie.net/building-sht-no-one-wantsIf this resonates, subscribe for more Web3 and founder marketing conversations, share the episode with a builder who needs it, and leave a review if you want to help the show grow...........................................................................Metricool is a new official podcast partner of Web3 CMO Stories in 2026. Metricool helps marketers and creators bring structure, clarity, and consistency to their social media workflows through analytics, planning, and reporting. Listeners can try Metricool Premium for free for 30 days using the coupon code JOERI.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan Mail93% of LinkedIn company pages didn't grow last year. That headline sounds like an algorithm problem. I see something more interesting: a belief problem. When personal profiles earn roughly the same impressions as company pages yet drive 63% more engagement, the platform is confirming what buyers have been signalling for years. People don't build relationships with logos. They build trust with humans who have a point of view and a track record.In this solo episode, I walk through the evidence from the new Metricool x Favikon playbook, LinkedIn in 2026, and connect it to what AI is changing in marketing right now. AI made publishing radically easier, which means posting more stops being a durable advantage. At the same time, visible engagement is falling while real engagement rises, because clicks are up and buyers decide silently. If you still judge LinkedIn by likes and comments alone, you're measuring applause while your buyer is watching quietly.Then it gets practical: where does belief actually come from? I break down the three circles of growth, starting with employees, expanding through customers and partners, and only then layering in external creators. You'll hear why scripted employee posts backfire, why ending every post with a question lifts comments by 77%, and why creator campaigns don't land on top of an empty trust layer.Download the Metricool x Favikon playbook >>One question to bring to your next marketing meeting: if your company page went silent tomorrow, who would still be talking about your brand?This solo episode was recorded via Descript on July 13, 2026. Read the blog article and show notes here: https://webdrie.net/linkedin-in-2026-why-people-not-pages-will-build-the-next-great-brands/.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailRegulation is supposed to slow you down, right? We argue the opposite: in Web3, regulation can be the advantage that makes you hard to copy and easy to trust. I sit down with Butch Takaoka from the RYO Project, a veteran of traditional finance who came into crypto as a sceptic and quickly realised the real story is not hype, it’s utility, credibility, and execution. We get specific about Japan, one of the most regulated markets in the world, and why a compliance-first approach can act like a long-term moat. Butch explains why consumer protection is not a constraint on innovation but proof you’re ready for the mainstream, especially after industry blow-ups that damaged public confidence. We also dig into what actually blocks adoption today: not just a lack of knowledge, but a lack of trust, plus the need for infrastructure people can see and touch. Then we zoom out to the bigger shift. AI makes it easier for both builders and bad actors, which means “looking real” is no longer enough. What can’t be faked is a proven track record of doing what you said you’d do, paired with simple user experience that feels familiar. We close with a clear view of the end game: Web3 becomes mainstream when people stop calling it Web3 and just use it in daily life, from wallets to payments to remittance. This episode was recorded through a Descript call on July 3, 2026. Read the blog article and show notes here: https://webdrie.net/the-real-barrier-isnt-technology-its-trust/If you know someone curious about crypto, trust, and Japan’s approach to innovation, share this conversation, subscribe to the show, and leave a review so more people can find it........................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailStarting a new domain can feel like shouting into the void, then waiting months for Google to believe you are real. Alex Drew, founder and CEO of Odys Global, shares a different approach: use aged domains with real history to accelerate domain authority, earn trust faster, and generate leads while your brand catches up.We dig into what still holds true after 15+ years of shifts in online business: quality matters, but networking and sales, as relationship-building, often decide who wins. Alex explains why Odys moved from a marketplace into done-for-you services and hybrid partnership models, especially in brutal, high-competition industries like iGaming where ranking speed and volatility change the rules. We also explore Blue Ocean strategy as a company policy: invest in R&D, test aggressively, and aim for breakthroughs that competitors cannot easily copy.Then we zoom out to the new reality of AI search and LLM marketing. When AI becomes a layer between users and brands, authority and reputation shift toward brand mentions and established signals, not just links. Alex breaks down how to separate valuable domain history from dangerous history using backlink analysis and archive checks, and why offline events, mentors, and trusted communities may become even more important as trust grows scarce.This episode was recorded through a Descript call on June 18, 2026. Read the blog article and show notes here: https://webdrie.net/great-products-dont-win-trusted-networks-do-alex-drew-odys-global/..........................................................................Metricool is a new official podcast partner of Web3 CMO Stories in 2026. Metricool helps marketers and creators bring structure, clarity, and consistency to their social media workflows through analytics, planning, and reporting. Listeners can try Metricool Premium for free for 30 days using the coupon code JOERI.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailDeFi isn’t just battling UX problems or chasing more liquidity, it’s quietly fighting the limits of the machine it runs on. I sit down with Joao Garcia from Cartesi to unpack a topic that rarely gets the spotlight but shapes everything you feel as a builder or user: the execution environment. If smart contracts behave like basic calculators, what happens when financial apps need deep math, big state updates, and predictable costs during market stress?We explore why “Linux on-chain” is more than a slogan. Most of the world’s software infrastructure already runs on Linux, and that history matters because it brings decades of proven tools, patterns, and libraries. Joao explains how enabling familiar environments and languages like Python, along with access to databases and file systems, can reduce the need to reinvent core financial logic in Solidity. That shift can lower gas pressure, reduce complexity, and make it easier to prove correctness using tried and tested components.From bonding curves to congestion risk, we map the difference between gas-optimised finance and computation-driven finance, plus why application-specific rollups can protect critical actions from being priced out by unrelated hype. We also get practical about trust: research-backed design, robust fraud-proof thinking, and settling on Ethereum as a dependable foundation. Then we connect the dots to AI-assisted development and spec-driven workflows, where better documentation and standard tooling make AI pair-programming far more effective.This episode was recorded through a Descript call on June 15, 2026. Read the blog article and show notes here: https://webdrie.net/what-if-defi-was-built-for-finance-firstIf you care about the next phase of Web3 infrastructure, DeFi scalability, and building trustworthy on-chain applications, hit subscribe, share this with a builder friend, and leave a review so more people find it. What part of the DeFi stack do you think is most underrated right now?.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailAI can generate a flawless post, a flawless pitch, even a flawless brand voice. So what do people trust when everything looks “perfect”? I sit down with Pierre Lindh, co-founder and managing director of Next.io, to explore why the most credible signal left might be the simplest one: real humans in the same room, having real conversations.Pierre takes us back to the story that shaped his entire career in community and events, starting with an 18-year-old running a poker club in Sweden and getting raided by police. From there, we trace how that early experience evolved into building large iGaming conferences that many delegates describe as “a room full of friends you haven’t met yet”. We get specific about what that takes at scale: designing networking that works for introverts and extroverts, creating side events that fit different energy levels, and giving first-timers structured ways to meet the right people without forcing awkward small talk.We also zoom out to the future of trust in a world shaped by AI and algorithms. Pierre explains why capital is flowing into live events, how AI can actually make conferences more purposeful through better matchmaking, and why authenticity and transparency become the marketing moat when “Apple-quality” campaigns are suddenly cheap. We finish with a deep dive into prediction markets, the wisdom of crowds, and why purpose may be the difference between a fringe category and a lasting industry.This episode was recorded through a Descript call on June 15, 2026. Read the blog article and show notes here: https://webdrie.net/a-police-raid-started-his-event-career-with-pierre-lindh-next-ioIf you enjoy conversations about Web3, AI, digital leadership, marketing, community building, iGaming, and the future of live events, subscribe, share this with a friend, and leave a review with 5 stars. What part of the trust puzzle are you wrestling with right now?..........................................................................Metricool is a new official podcast partner of Web3 CMO Stories in 2026. Metricool helps marketers and creators bring structure, clarity, and consistency to their social media workflows through analytics, planning, and reporting. Listeners can try Metricool Premium for free for 30 days using the coupon code JOERI.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................

Send us Fan MailCompetition is loud right now. AI tools are everywhere, content is infinite, and customer acquisition costs keep climbing. So what still works when everyone can publish, target, and “optimise”? Joeri Billast sits down with Valentina Diaco, founder and strategic business advisor in iGaming and tech, to get concrete about the lever most teams forget: the emotional driver behind why people choose you and stay with you.We talk about what Valentina sees across industries, from luxury to entertainment to iGaming marketing, and why retention is the profit engine when acquisition gets expensive. We also unpack how she designed AIMatch Sessions as a curated, non-transactional networking experience, built from real attendee challenges around AI adoption. The goal is simple: create the right conditions for meaningful conversations that turn into ideas, partnerships, and real business outcomes.Then we go deeper on AI strategy and digital leadership. “AI is not a crystal ball, it is a mirror” becomes a practical framework for keeping humans in the loop, building a living knowledge base, and orchestrating AI agents without surrendering judgment. We also explore the shift from CMO to Chief Value Officer, the balance of performance marketing with trust and responsibility in regulated markets, and blue ocean strategy for creating new categories instead of battling in crowded spaces.This episode was recorded through a Descript call on June 12, 2026. Read the blog article and show notes here: https://webdrie.net/ai-is-not-a-crystal-ball-its-a-mirrorIf you care about AI marketing, brand strategy, customer retention, and building trust in the Web3 and iGaming world, hit play. Subscribe, share this with a friend, and leave a five-star review if it helps you grow...........................................................................Metricool is a new official podcast partner of Web3 CMO Stories in 2026. Metricool helps marketers and creators bring structure, clarity, and consistency to their social media workflows through analytics, planning, and reporting. Listeners can try Metricool Premium for free for 30 days using the coupon code JOERI.......................................................................... 📘 Read The Future CMO: Amazon 👥 Join the Future CMO Community 🌿 Explore Sintra Synergies Retreat 💼 Connect on LinkedIn..........................................................................