Marketing Against the Grain

25 episodes scanned. 76% of ad slots promote the show's own products.

Recent Episodes

1. I Automated 90% of My Content Creation with Claude (Copy My System)

   Nov 3, 2026

   Saj Adib, the founder behind Skill Leap AI, walks through several custom apps he built with Claude over about two weeks. These include a YouTube Shorts production system that edits videos through Adobe Premiere, a live command center, and a personal 3D virtual world built in Blender. He also describes Futurepedia 2.0, an AI tool directory expanded into personalized workflows and use cases, and the episode closes with his advice on using AI more creatively.

2. We’ve Spent 20+ Years in Marketing. Here’s What We Learned

   Oct 29, 2026

   Hosts Kipp Bodnar and Kieran Flanagan walk through six lessons from classic marketing books, including Direct Mail Copy That Sells, Tribes, How to Win Friends and Influence People, Obvious Adams, and Reality in Advertising. They focus on verisimilitude in copy, drawing inspiration from outside your industry, building the right audience, and writing well instead of relying on AI and trending tactics. The episode also includes HubSpot sponsor segments.

3. You're Not Behind Yet: Learn 97% of Claude (From an AI Expert)

   Oct 27, 2026

   Ruben Hassid, known as the "Claude guy" and author of the newsletter and book "How to AI," joins Kipp Bodnar and Kieran Flanagan to discuss how AI is changing marketing and writing. The conversation covers why AI-generated writing style and heavy context files can work against originality, why writing is tied to thinking, and how Claude's settings, memory, and connectors have simplified over time. It also touches on agents, the future of software, and the role of human connection in business.

4. How Marketers Can Make $20K/Month With Tiny Apps

   Oct 22, 2026

   In this solo episode, Kieran Flanagan lays out a "microbehavior business formula" for marketers to build small, niche AI-built software products. He walks through case studies such as Launch Fast, Sync 2 Sheets, and Blog to Pin, and demonstrates a prototype built for traveling tattoo artists. The episode focuses on distribution and marketing as the main competitive advantage now that AI has commoditized software building.

5. The Marketing Teams Of 2027 Will Look VERY Different...

   Oct 15, 2026

   In this solo episode of Marketing Against The Grain, Kieran Flanagan argues that AI is changing which roles modern marketing teams need, and he outlines three hires he would prioritize: a growth producer, an internet comedian, and a creator dealmaker. He illustrates each role with examples from Ramp, Muse, CapCut, and ClickUp, and describes how AI-driven research shifts growth work toward awareness. The episode also covers how to vet creator audiences for fake engagement and why creator programs need incentives beyond fees.

6. Marketing Experts Turn GrokBot Into an AI Content Team

   Oct 13, 2026

   Kieran Flanagan hosts this solo tutorial episode, in which he builds a multi-agent AI content team in Grok Bot. The team monitors YouTube channels, generates and ranks content ideas, runs research, and drafts a YouTube transcript. He also covers connecting the bots to external tools through Monit, tuning each agent to a file describing the audience and the show's point of view, and choosing different AI models for different steps.

7. How to Turn Instagram Into a Sales Machine With Muse AI

   Oct 8, 2026

   Kipp Bodnar presents a solo episode on Meta's Muse AI assistant as a tool for growing an Instagram audience and turning engagement into revenue. He demonstrates Muse generating an audience and growth strategy for the Marketing Against the Grain Instagram account, then pulling a spreadsheet of likers' public contact details from a clip post. He argues this lets marketing and sales teams follow up with people who engage with specific content, tying social activity to pipeline.

8. We Tested What AI Personal Assistants Can Actually Do

   Oct 6, 2026

   Kipp Bodnar and Kieran Flanagan explore the explosive rise of personal AI agents like Meta's Muse, Instinct, and Grokbot, demonstrating how these tools are fundamentally changing consumer buying behavior and making traditional marketing strategies obsolete. They showcase live examples of AI agents autonomously researching, comparing, and purchasing products, then outline how marketers must shift from demand capture to brand awareness, prioritize proof over positioning, and ensure transparent pricing and information online to remain visible to AI buyers.

9. HubSpot Execs: What Marketing Teams Look Like in 2027

   Oct 1, 2026

   HubSpot marketing executives Kipp Bodnar and Kieran Flanagan discuss the future structure of marketing teams in 2027, challenging the narrative that teams are shrinking. They present three core components: AI-native "zero-to-one" generalist marketers with personal AI stacks, domain experts who provide depth of craft in specialized areas, and a pod-based organizational model inspired by product and engineering teams. The hosts outline how token costs should be budgeted alongside headcount, how sprints and outcome-focused work prevent AI waste, and propose an exploratory team model where generalists test new opportunities before specialists scale winning initiatives.

10. Train Your AI to Write Like a Human With Just 3 Files

    Sep 29, 2026

    Kieran Flanagan demonstrates how to build a Creative Context OS—three simple markdown files that teach AI to write like you. He covers the core problem: AI models are excellent at creating content, but produce commodity content that lacks individual perspective. By creating a creator.md file (how you think), audience.md file (who you write for), and taste.md file (what you consider good), marketers can use AI as an ideation and editing partner rather than a content generator, ensuring their voice remains distinctly theirs.