Marketing Against The Grain

Latest Episodes:

Dharmesh Shah: “The New AI Era Will Create Millions of One-Person Businesses Sep 15, 2026

Show notes

[Free guide] build your second brain with AI: https://clickhubspot.com/efeg

To get started with YouSpot, go to https://youspot.com/pricing/pro?promo=BRAINTHEGRAIN You'll then see the coupon code automatically applied on checkout.

Ep. 453

Did you know that 86% of all new companies started aren’t expected to hire any employees?

Kipp, Kieran, and guest Dharmesh Shah (Founder of HubSpot) dive into the rapidly growing world of one-person businesses and how AI is fueling a new wave of solopreneurs. Learn more on the evolution of the "second brain" for entrepreneurs, how agentic AI harnesses are changing the game, and why rethinking CRMs for solo operators is unlocking new levels of productivity.

Mentions

Dharmesh Shah https://www.linkedin.com/in/dharmesh/
Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
YouSpot https://youspot.com/
Agent.ai agent.ai
SecondBrain https://youspot.com/about/secondbrain
Obsidian https://obsidian.md/
Fable 5.1 https://www.anthropic.com/claude-fable-and-mythos-5-1

Go to YouSpot.com and use code BRAINTHEGRAIN at checkout for the special Marketing Against the Grain price.

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

I Spend $400K/Day on Meta Ads. Here's What's Working Right Now Sep 10, 2026

Show notes

Free Meta Ad Creative Prompt Pack: https://clickhubspot.com/prgl

Ep. 452

Could your company grow to $20M in revenue in just 20 months by focusing 80% of your ad budget on a single channel?

Kipp, Kieran, and guest Danny Yeung (CEO and co-founder of IM8) dive into the marketing strategy behind the explosive growth of IM8 and how Meta became their powerhouse for customer acquisition. Learn more on how to master Meta’s platform with creative-first tactics, build a high-performing marketing team for rapid scale, and leverage offline strategies to make your brand unforgettable.

Mentions

Danny Yeung https://hk.linkedin.com/in/dyeung22
IM8 https://im8health.com/
Prenetics https://www.prenetics.com/
Allianz https://www.allianzlife.com/
Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book

Ask Kipp and Kieran a question!

https://form.asana.com/?k=U4n5W_3WC2SkQO1bwK8Xzg&d=8587152060687

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

Is the CMO Role About to Disappear Forever? Sep 08, 2026

Show notes

Build your AI marketing department with this Claude skill: ⁠https://clickhubspot.com/rlcb⁠

Ep. 451

Is the CMO role dying?

Kipp and Kieran dive into why marketing’s highest seat is under pressure and what founders and marketers should do about it. Learn more on why the expectations for marketing leaders are higher than ever, how the evolution of marketing skills and AI are shaping the talent pipeline, and what strategies companies can use when they can’t find the perfect head of marketing.

Mentions

Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
LinkedIn https://www.linkedin.com/

Ask Kipp and Kieran a question!

https://form.asana.com/?k=U4n5W_3WC2SkQO1bwK8Xzg&d=8587152060687

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

I Built a $120K/yr Social Media Funnel w/Claude (Full Demo) Sep 03, 2026

Show notes

Turn social comments into leads with Claude + Blotato: https://clickhubspot.com/rkhv

Ep. 450

How can one Reel drive $120,000 in annual recurring revenue for your business?

Kipp, and guest Sabrina Ramonov of Blotato dive into how high-performing social content and automated DMs can be seamlessly converted into real revenue and loyal customers. Learn more on building viral social funnels, the power of DM automation for lead capture and monetization, and why treating short-form video as advertising for your long-form brand is the ultimate growth strategy.

Mentions

Sabrina Ramonov https://www.youtube.com/@sabrina_ramonov
Blotato https://www.blotato.com/
Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
Claude https://claude.ai/
ChatGPT https://chatgpt.com/

Ask Kipp and Kieran a question!

https://form.asana.com/?k=U4n5W_3WC2SkQO1bwK8Xzg&d=8587152060687

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

How I Turned Codex Into My Personal Research Assistant (Matt Wolfe) Sep 01, 2026

Show notes

*Build your AI Research Desk in Codex:* https://clickhubspot.com/inyh

Ep. 449

Is informational content on the internet dead?

Kipp, Kieran, and guest Matt Wolfe (Future Tools) dive into how you can reclaim hours each week by automating newsletter reading, brand mentions, and industry news updates with your own personal AI system. Learn more on building a custom info dashboard with AI agents, the future of media consumption and creator-business relationships, and how you can leverage open-source tools to create a second brain for your work and life.

Mentions

Matt Wolfe https://www.youtube.com/@mreflow
Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
GitHub https://github.com/
Gemini Omni 1.1 Flash https://blog.google/innovation-and-ai/technology/developers-tools/build-with-gemini-omni-1-1-flash/
Codex https://chatgpt.com/codex/
Claude https://claude.ai/
Obsidian https://obsidian.md/

Ask Kipp and Kieran a question!

https://form.asana.com/?k=U4n5W_3WC2SkQO1bwK8Xzg&d=8587152060687

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

Claude vs. Human Marketer: Which Is Actually Better? Aug 27, 2026

Show notes

Build your AI marketing department with this Claude skill: https://clickhubspot.com/uyon

Ep. 448

Can you really fire your entire marketing team and replace them with AI?

Kieran dives into the reality behind agentic marketing systems by putting an AI-powered marketing “team” to the test for a fast-growth AI company. Learn more on how AI audits and rewrites website copy, tackles product positioning, competes in search and LLMs, and whether these emerging systems can actually outperform the average marketer or just generate average results.

Mentions

Open Source GitHub system https://github.com/Yuzzyuk/marketing-os
Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
Claude https://claude.ai/login
ChatGPT https://chatgpt.com/
Ramp https://ramp.com/
1Mind https://www.1mind.com/

Ask Kipp and Kieran a question!

https://form.asana.com/?k=U4n5W_3WC2SkQO1bwK8Xzg&d=8587152060687

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

How to Stop AI from Killing Your Critical Thinking w/ David Epstein Aug 25, 2026

Show notes

Get our anti-AI slop checklist: https://clickhubspot.com/lhug

Ep. 447

For most people, AI is making your marketing worse. For a select few, it's making it 10 times better.

Kipp and guest David Epstein (author of Range (#1 NYT bestseller) and the new Inside the Box: How Constraints Make Us Better (May 2026)) dive into why AI is creating a wave of “slop marketing” and what marketers can do to protect—and strengthen—their critical thinking in an age of automation. Learn more on proven frameworks for defining the right problems, the power of independent team thinking, and how cutting through complexity helps you deliver clear, remarkable marketing.

Mentions

Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
David Epstein https://davidepstein.com/
Inside the Box: How Constraints Make Us Better https://a.co/d/0dSEv0R5
Nest https://home.nest.com/
Scite https://scite.ai/

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

How to Run a Marketing Agency With 0 Employees ($100k to $1M) Aug 20, 2026

Show notes

Free: build a Claude-powered content engine https://clickhubspot.com/mslb

Ep 446

What does it actually take to 5x your solo marketing business in a year using AI?

Kipp, Kieran, and guest Barbara Jovanovic (Founder of Startup Cookie) dive into how top solo marketers are scaling agencies with agentic AI systems, and why most automated LinkedIn content totally misses the mark. Learn more on how agentic systems drive efficiency and scale for one-person teams, the difference between building a real content workflow versus relying on prompts, and why authentic insights—not just automation—are the secret to standout founder-led growth on LinkedIn and X.

Mentions

Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
Barbara Jovanovic https://www.linkedin.com/in/barbara-startup-cookie
StartupCookie https://startupcookie.com/
Claude https://claude.ai/
ChatGPT https://claude.ai/
ChatGPT Codex https://chatgpt.com/codex/
Granola https://www.granola.ai/
Buffer https://buffer.com/
Wispr Flow https://wisprflow.ai/

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

Automate Boring Marketing Work With This Claude System Aug 18, 2026

Show notes

Ep. 445

Everybody online is telling you that the only marketers who will survive in the AI era are systems builders. But what does that even mean—and how do you actually build your own AI-powered marketing system?

Kieran dives into the essential starting stack every marketer can implement to become a systems builder and thrive with AI. Learn more on the key layers of a marketing AI system, how to create a personalized intelligence layer that powers your skills and plugins, and the tools you can use to automate your workflow, scale yourself across your team, and stand out with a differentiated product story.

Mentions

Loop: Outlearn. Outmarket. Outgrow https://www.hubspot.com/loop-marketing-book
Claude https://claude.ai/
ChatGPT https://chatgpt.com/

Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt

Resource

[Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip

We’re on Social Media! Follow us for everyday marketing wisdom straight to your feed

YouTube: https://www.youtube.com/@matgpod

Twitter: https://twitter.com/matgpod

TikTok: https://www.tiktok.com/@marketingatg

Thank you for tuning into Marketing Against The Grain!

Don’t forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934

We really appreciate your support.

Host Links:

Kipp Bodnar, https://twitter.com/kippbodnar

Kieran Flanagan, https://twitter.com/searchbrat

‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by Hubspot Media // Produced by Darren Clarke.

How Top 1% Marketers 10X Their Memory With AI Aug 13, 2026

Show notes

Build your AI knowledge base (template + kit): https://clickhubspot.com/fhfs

Ep. 444

Stop outsourcing your intelligence to AI assistants—build your own personal intelligence layer instead!

Kieran dives into how to construct your own marketing intelligence layer that you can plug into any AI assistant for a serious competitive edge. Learn how to capture and structure career learnings, keep your intelligence portable and up-to-date, and turn your unique insights into the biggest differentiator in the age of AI.

Mentions