How Rationality F’s up your B2B Strategy

How Rationality F’s up your B2B Strategy

How do you balance rationality and irrationality as a business leader? How do you position your company and product to disrupt the market? Kipp and Kieran go on a deep dive on how playing it safe is actually hurting your business, how to know when to hire a head of marketing vs. a product marketer, using emotions to position your product, and more! Plus, We answer one of YOUR questions. Shoutout to Fanny Kuhn for leaving their review! Do you want to be the next featured listener question? Leave your questions in the reviews and we may feature you next. Links Mentioned: Loom https://www.loom.com/ Sapiens by Yuval Noah Harari https://www.ynharari.com/book/sapiens-2/ The Hard Things About The Hard Things by Ben Horrowitz https://a16z.com/book/the-hard-thing-about-hard-things/ Hooked by Nir Eyal https://www.nirandfar.com/hooked/ Rework by Jason Fried https://www.amazon.com/Rework-Jason-Fried/dp/0307463745 The Platform Revolution https://www.amazon.com/Platform-Revolution-Networked-Markets-Transforming/dp/0393249131 Stratechery https://stratechery.com/ Not Boring Newsletter https://www.notboring.co/ The Hustle Newsletter https://thehustle.co/ Milk Road Newsletter https://www.milkroad.com/ Positioning The Battle for your Mind by Al Ries https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 Ready Player One by Ernest Cline https://www.amazon.com/Ready-Player-One-Ernest-Cline/dp/0307887448 Principles for The Changing World Order by Ray Dalio https://www.amazon.com/Changing-World-Order-Nations-Succeed/dp/1982160276 Shoe Dog by Phil Knight https://www.amazon.com/Shoe-Dog-Memoir-Creator-NIKE/dp/1471146723/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=1654105299&sr=1-1 Direct Mail Copy That Sells by Herschell Gordon Lewis https://www.amazon.com/Direct-Mail-Copy-That-Sells/dp/0132147505/ref=sr_1_3?crid=2544SEVJ4RL7Q&keywords=Direct+Mail+Copy+That+Sells&qid=1654105342&s=books&sprefix=direct+mail+copy+that+sells%2Cstripbooks%2C68&sr=1-3 On Writing Well by William Zinsser https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/ref=sr_1_1?crid=30RQWSPYFT6FV&keywords=on+writing+well&qid=1654105374&s=books&sprefix=on+writing+well%2Cstripbooks%2C78&sr=1-1 New Rules of Marketing PR by David Meerman Scott https://www.davidmeermanscott.com/books/the-new-rules-of-marketing-and-pr The Rational Optimist by Matt Ridley https://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068 Twitter Blue https://help.twitter.com/en/using-twitter/twitter-blue 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 If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. We really appreciate your support. 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 The HubSpot Podcast Network // Produced by Darren Clarke.

Episoder(384)

The Brand NEW AI Marketing Strategy for 2025

The Brand NEW AI Marketing Strategy for 2025

Want our free Loop Marketing Prompt Library (with 100 prompts)? Get it here: https://clickhubspot.com/kcl Ep. 362 Did you know that 58.5% of Google searches now end without a click? Kipp and Aja Frost, Sr. Director of Global Growth at HubSpot, dive into how AI has fundamentally changed the marketing landscape—and what you can do about it. Learn more on why old-school tactics like linear funnels and basic personalization are outdated, how “loop marketing” can future-proof your strategy, and which AI-powered tactics drive explosive growth when traffic and attention are harder than ever to capture. This episode was recorded at HubSpot’s Inbound 2025.  Mentions HubSpot Inbound https://www.inbound.com/ Aja Frost https://www.linkedin.com/in/ajafrost/ Claude https://claude.ai/ Perplexity https://www.perplexity.ai/ Breeze Assistant https://knowledge.hubspot.com/ai/use-breeze-assistant Gemini https://gemini.google.com/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

16 Sep 32min

This is How the Top 1% Marketers are Using AI

This is How the Top 1% Marketers are Using AI

Want 22 ChatGPT Marketing Agents to handle your work? Get it here: https://clickhubspot.com/bpg Ep. 361 Marketing is only limited by your own creativity and ambition right now. Kipp and Nicholas Holland, Head of AI, SVP Product at HubSpot, dive into how the world’s top 1% of marketers are deploying AI for explosive growth. Learn more on why context is the most important word for AI in 2026, the rise of agents and assistants for every marketing use case, and how today’s marketers can 10x their creativity by practicing and pushing past the limits of what’s possible. Mentions Nicholas Holland https://www.linkedin.com/in/nashvilleholland/ HubSpot Breeze https://www.hubspot.com/products/ai ChatGPT https://chatgpt.com/ Gemini https://gemini.google.com/ Nano Banana https://nanobanana.ai/ Google Veo https://deepmind.google/models/veo/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

11 Sep 26min

I Stole Microsoft CEO’s 4 Most Powerful AI Prompts

I Stole Microsoft CEO’s 4 Most Powerful AI Prompts

Want Kieran's 4 AI prompts that drive big results? Get it here: https://clickhubspot.com/uph Ep. 360 Did you know the CEO of Microsoft, just gave away his four most powerful daily AI prompts for boosting productivity and leadership? Kieran dives into how you can swipe, upgrade, and use the very same prompts Satya Nadella relies on every single day. Learn how to prep smarter for every meeting, get real-time project status updates, check if you’ll hit your deadlines, and analyze exactly how you’re spending your time.  Mentions Satya Nadella https://www.linkedin.com/in/satyanadella/ Microsoft https://www.microsoft.com/en-us/ Microsoft Copilot https://copilot.microsoft.com/chats/HATNMvfutDfR73T3acuz1 Claude https://claude.ai/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

9 Sep 15min

Marketing is Broken - This is the Future of Conversions (Loop Framework)

Marketing is Broken - This is the Future of Conversions (Loop Framework)

Want our NEW Loop Marketing Prompt Library? Get it here: https://clickhubspot.com/lmp Ep. 359 Did you know that 60% of Google searches now end without a single click? Kipp and Aja Frost, Sr. Director of Global Growth at HubSpot, dive into why traditional marketing is broken and what the future of conversions looks like in a world dominated by AI. Learn more about how AI is upending search and website traffic, why the future belongs to marketers who can personalize experiences at scale, and the brand new Loop Framework that will transform how you drive results in 2024 and beyond. Mentions Aja Frost https://www.linkedin.com/in/ajafrost/ HubSpot Loop Marketing https://www.hubspot.com/loop-marketing ChatGPT https://chatgpt.com/ Claude https://claude.ai/ Perplexity https://www.perplexity.ai/ Quora https://www.quora.com/ Reddit https://www.reddit.com/ Discord https://discord.com/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

4 Sep 27min

The Startup Letting 99% of People Build Apps Without Code

The Startup Letting 99% of People Build Apps Without Code

Want our complete app-building guide + $25 Lovable credit? Get it here: https://clickhubspot.com/fkw Ep. 358 10% of all new sites on the internet in June were built with Lovable Kieran dives into Lovable, the fastest-growing app in Europe, with its co-founder Anton Osika. Learn more about the implications for marketers and founders, how distribution and audience-building are evolving, and how to adapt your team and mindset to thrive in the era of AI-generated software. Mentions Anton Osika https://www.linkedin.com/in/antonosika/ Lovable https://lovable.dev/ Eoghan McCabe https://www.linkedin.com/in/eoghanmccabe/ Y Combinator https://www.ycombinator.com/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

2 Sep 34min

How the Top 1% Use AI to 10x Their Productivity (Before Lunch)

How the Top 1% Use AI to 10x Their Productivity (Before Lunch)

Want Kieran's AI Executive Team Stack? Get it here: https://clickhubspot.com/kfv Ep. 357 Did you know 95% of all AI pilots are failing, according to a recent MIT study? Kieran dives into how the top 1% of executives, leaders, and founders are using AI to 10x their productivity—before lunch. Learn more about how to use AI as your Chief of Staff to eliminate blockers and prioritize your day, streamline your executive updates and communications, and leverage AI as a strategic thought partner to sharpen your critical thinking and problem solving. Mentions MIT https://www.mit.edu/ ChatGPT https://chatgpt.com/ Custom GPT https://customgpt.ai/ Genspark https://www.genspark.ai/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

28 Aug 22min

Inside the $130M AI Startup Growing Faster Than ChatGPT

Inside the $130M AI Startup Growing Faster Than ChatGPT

Want Elena's AI Tech Stack that helped grow her startup? Get it here: https://clickhubspot.com/fkv Ep. 356 Did you know Lovable is the fastest-growing AI app on the planet—scaling faster than ChatGPT? Kieran dives into what it takes to succeed in today’s AI-native startup world, with growth leader Elena Verna revealing how Lovable is changing the game for building and scaling tech companies. Learn more on why traditional management roles are disappearing, how end-to-end ownership and autonomy are driving insane speed at Lovable, and how the growth playbook is transforming for a generation of AI-powered products. Mentions Elena Verna https://www.linkedin.com/in/elenaverna/ Lovable https://lovable.dev/ Cursor https://cursor.com/ Miro https://miro.com/ SurveyMonkey https://www.surveymonkey.com/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

26 Aug 45min

The New Marketing Playbook: Identity Over Algorithm

The New Marketing Playbook: Identity Over Algorithm

Want our Vibe Marketing Playbook to resonate with your audience? Get it here: https://clickhubspot.com/wua Ep. 355 Is the era of "who publishes the most content wins" over? Kipp, Kieran, and Alex Lieberman, co-founder of Morning Brew, dive into why marketers need to shift from churning out content to building a resonant brand identity that stands out in a crowded landscape. Learn more on why taste and speed—not just algorithms—will define marketing winners, the four moats shaping both software and content businesses, and how network effects and data are giving companies an unbeatable edge. Mentions Alex Lieberman https://www.linkedin.com/in/alex-lieberman Morning Brew https://www.morningbrew.com/ Zapier https://zapier.com/ OpenAI https://openai.com/ Claude https://claude.ai/ Get our guide to build your own Custom GPT: https://clickhubspot.com/customgpt We’re creating our next round of content and want to ensure it tackles the challenges you’re facing at work or in your business. To understand your biggest challenges we’ve put together a survey and we’d love to hear from you! https://bit.ly/matg-research 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/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg 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   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. 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.

21 Aug 12min

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