Marketing Against the Grain

Recent Episodes

1. Zero-Click Marketing: How to Win When Google Stops Sending Traffic

   Sep 17, 2026

   Amanda Natividad, founder of Zero Click Marketing and co-author of the forthcoming book Zero Click Marketing, joins hosts Kipp and Kieran to discuss the seismic shift in search behavior: 68% of Google searches now end without a click. The episode covers how this trend has accelerated over the past decade, what it means for businesses dependent on organic traffic, and the five rules of zero-click marketing strategy needed to succeed in this new landscape.

2. Dharmesh Shah: “The New AI Era Will Create Millions of One-Person Businesses

   Sep 15, 2026

   Dharmesh Shah, co-founder of HubSpot, discusses the evolution of AI from large language models to agentic reasoning systems and introduces YouSpot, a CRM and 'second brain' platform purpose-built for one-person companies. He explores how AI reasoning improvements since November 2024 enable agents to handle complex, multi-step tasks, and how persistent memory systems can amplify AI capabilities. The conversation covers the explosion of solopreneur businesses (86% of new US company formations expected to remain solo), agentic harnesses as the real leverage point in AI, and practical use cases from domain investment tracking to recruiting and prospecting workflows.

3. I Spend $400K/Day on Meta Ads. Here's What's Working Right Now

   Sep 10, 2026

   Danny Yeung, CEO and co-founder of IM8, discusses how the supplements brand scaled from $0 to hundreds of millions in revenue in 20 months by allocating 80% of ad spend to Meta. He reveals his creative-first playbook for Meta ads, emphasizing content diversity over targeting, and shares how his 70-person team manages production of 50-60 core creative assets with weekly testing of 500+ ad variations. Yeung details his approach to leveraging AI tools, offline brand activations at major sporting events, and the importance of product quality in driving organic partnerships with athletes and celebrities.

4. Is the CMO Role About to Disappear Forever?

   Sep 8, 2026

   Kipp Bodnar and Kieran Flanagan, hosts of Marketing Against the Grain, debate whether the CMO role is dying. They examine data showing a 10% decline in B2B CMO positions, explore why founders are restructuring marketing (splitting brand/product into product org, growth/demand into sales org), and discuss the root cause: a talent pipeline mismatch where founders now demand world-class expertise across both technical growth and creative brand disciplines—skills rarely found in a single person. The hosts propose alternative hiring strategies, including hiring multiple specialists, taking bets on emerging talent with advisory mentorship, and building long-term relationships with potential marketing leaders.

5. I Built a $120K/yr Social Media Funnel w/Claude (Full Demo)

   Sep 3, 2026

   Sabrina Ramonov, founder of Blotato, demonstrates how to convert social media engagement into revenue through DM automation and strategic funnel design. She breaks down how a single Instagram Reel with 200,000 views generated $120,000 in annual recurring revenue, and walks through building automated DM workflows using Claude AI that capture leads, nurture followers, and drive monetization across owned channels like email newsletters.

6. How I Turned Codex Into My Personal Research Assistant (Matt Wolfe)

   Sep 1, 2026

   Matt Wolfe, founder of Future Tools, demonstrates his custom AI research dashboard built in Codex that automates newsletter reading, brand mention tracking, and industry news aggregation. The system uses RSS feeds, website sitemaps, and AI filtering to surface relevant information across tech news sources, newsletters, and social media, saving hours of weekly consumption time. Wolfe discusses the implications of AI-powered information curation on content creators and media consumption, shares his open-source GitHub implementation, and walks through how anyone can build their own personalized AI research assistant.

7. Claude vs. Human Marketer: Which Is Actually Better?

   Aug 27, 2026

   Kieran Flanagan tests whether agentic AI marketing systems can truly replace human marketing teams by running a real-world audit and campaign development for 1Mind, a fast-growing AI sales agent company. Using an open-source GitHub-based marketing system with Claude and ChatGPT integrations, he evaluates the AI's output across website audits, copywriting, product positioning, competitive analysis, SEO/LLM visibility, and email campaign creation. The episode demonstrates that while AI systems can produce above-average marketing work suitable for solopreneurs and small teams, they require strong context files, expert human judgment, and cannot yet match world-class marketing strategy.

8. How to Stop AI from Killing Your Critical Thinking w/ David Epstein

   Aug 25, 2026

   David Epstein, author of three New York Times bestsellers including Range and the upcoming Inside the Box, discusses how AI is creating "slop marketing" and explores frameworks for protecting critical thinking in an automated age. The conversation covers the power of constraints, the think-slow-act-fast principle, and practical strategies for defining problems clearly before execution—from Pixar's story development process to NASA's resource-constrained innovation.

9. How I Run a $1M/year Marketing Agency With 0 Employees

   Aug 20, 2026

   Barbara Jovanovic, founder of Startup Cookie, returns to discuss how she scaled her one-person marketing agency 5x in one year using agentic AI systems, particularly Claude. She walks through her complete process for building founder-led content at scale, including how to structure context documents, set up multi-agent workflows, and avoid AI content quality issues. The episode includes a free downloadable skill that enables marketers to replicate her system for creating high-quality LinkedIn and X content.

10. Automate Boring Marketing Work With This Claude System

    Aug 18, 2026

    Kieran Flanagan, an engineering-background marketer at HubSpot, breaks down how to build an AI-powered marketing system that automates repetitive work and scales individual productivity. He presents a starter stack organized in layers—an intelligence context layer, scaling skills, better thinking frameworks, product story tools, and daily workflow automation—with a single prompt that marketers can use to build their own V1 system in Claude or ChatGPT.