The Dave Gerhardt Show (from Exit Five)

#362 | Dave sits down with Eddie Shleyner, founder of VeryGoodCopy.com, to talk about why great marketing copy can't be generated — it has to be written. They get into why AI writing feels flat, what separates copy that moves people from copy that just fills space, and why the process of writing is where the real work happens. Eddie also shares how he accidentally built one of the most-read copywriting newsletters on the internet and what he's learned about writing for humans after years of studying what makes people take action.

Timestamps

(00:00) - - - How Eddie accidentally discovered copywriting while writing job ads

(02:58) - - - Why marketers are starting to push back on AI-generated content

(02:59) - - - Why the best copy gives readers less — and makes them feel more

(03:04) - - - Marketing is a human profession because empathy can't be prompted

(03:13) - - - Where AI actually helps: research, not writing

(03:17) - - - How VeryGoodCopy started as a private Google Doc no one was supposed to see

(03:22) - - - Why AI writing tells you how to feel instead of letting you feel it

(03:23) - - - The experiment: Eddie wrote the same story as AI, word for word, to prove a point

(03:25) - - - What inspired writing has that AI writing doesn't

(03:31) - - - Why shortcuts in the writing process produce worse work, not faster work

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

#361 | In this episode, Matt Carnevale, Head of Community at Exit Five talks with three marketers doing impactful work in AEO. AI search is changing how buyers find products, and most B2B teams are still figuring out where to start. In this session, each marketer shares what's working and wins they’ve experienced — from earned media and technical audits to homepage fixes and tracking AI visibility. Whether you call it AEO, GEO, LLMO, or EIEIO – this one’s for you. This session features guests Matt Dzugan, VP of Data Intelligence at Muckrack, Brett Bernath, Director of Product at Webflow, and Jess Joyce, Founder of Inbound Scope – an SEO and AI Search consultancy.

Timestamps

(00:00) - - - Why 80% of CMOs say AEO is a top priority — and most don't know where to start

(02:48) - - - How Muckrack used original research to get cited in ChatGPT before their product launch

(02:50) - - - Why top-of-funnel content is getting eaten by AI — and where to focus instead

(02:53) - - - Quick win #3: authority — how to show up in Reddit and third-party platforms

(02:56) - - - The sleeper tip: Bing Webmaster Tools is already giving you first-party AI data

(03:07) - - - How to handle competitor comparison content without verifiable claims falling flat

(03:23) - - - The four-bucket AEO maturity model: content, technical, authority, measurement

(03:24) - - - Why your homepage is your worst-performing page for AI discoverability

(03:27) - - - Quick win #1: technical hygiene — schema, meta descriptions, and structured data

(03:28) - - - How to identify which journalists get cited most by AI in your niche

(03:29) - - - Quick win #2: are you actually answering what your customers are asking?

(03:34) - - - Why 1 in 3 B2B SaaS sites have technical blockers killing AI discoverability

(03:36) - - - Why original research is the single best content type for earning AI citations

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

#360 | Dave sits down with Ishveen Jolly, founder and CEO of Open Sponsorship, to talk about what influencer and athlete marketing actually looks like for B2B brands — and why it's more accessible than most marketers think. Ishveen breaks down how a $5K March Madness campaign outperformed traditional ads, why your first influencer deal will almost certainly miss on the offer, and how to think about sports sponsorships without a Tommy Fleetwood budget. They get into audience-fit versus story-fit sponsorships, why the goal should never be a landing page click, and why most B2B teams are applying the wrong success metrics from the start. If you've ever wondered how to get into influencer or sports sponsorship marketing without a Fortune 500 budget, this is the episode.

Timestamps

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

#359 | Dave sits down with Casey Patterson, Director of ABM at Snowflake, to talk about what ABM actually looks like inside one of the biggest companies in enterprise software. Casey breaks down how she cold LinkedIn messaged her now-boss Hillary to get her ABM decks reviewed before ever working together, why ABM works best when marketing stops thinking about credit and just focuses on helping sales get into accounts, and how she's thinking about the shift from traditional ABM plays to agent-driven ABM. They also get into geo-fenced out-of-home advertising, one-to-one field marketing plays, and why the future of ABM looks more like Netflix than a campaign calendar. Plus a surprisingly good tangent on finding mentors and how to actually get one.
Timestamps

(00:00) - - How Casey cold LinkedIn messaged her way into a mentorship

(08:42) - - What a mentor actually is and how to find one

(15:41) - - Why delusional confidence is underrated in marketing

(20:12) - - The crux of ABM: sales alignment or nothing

(23:19) - - ABM is not running digital ads to a list of accounts

(28:44) - - How Casey thinks about running a team of 23 ABM marketers

(31:39) - - A real ABM play: field event, OOH, gifting, and email at once

(40:52) - - How to figure out the right number of accounts to target

(45:53) - - Agent ABM: the three phases Casey is building toward

(49:09) - - The future of ABM: reaching people in their preferred channels

(51:11) - - How Dave uses AI to write his newsletter

(57:54) - - The bull case for marketers in the age of AI

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more

#358 | Ben Wallis (Customer Lifecycle Manager, Quo), Jaina Mistry (Director of Brand and Content Marketing, Knak), Kremi Mestanova (B2B Content and Growth Strategist, Kremi Marketing), and Tyler Cook (Head of Email Marketing, Hypermedia Marketing) join Dave for an Exit Five live session on what's actually working in email right now. Ben shows how Quo built a Spotify Wrapped-style year-in-review campaign with fully personalized GIFs and real usage data for every customer. Jaina makes the case for why B2B newsletters are one of the most slept-on trust-building channels in marketing, and breaks down the operating model that makes it sustainable. Tyler Cook shares his five-step AI-powered newsjacking system that goes from trend to sent email in under an hour, including a real example that got a 67% open rate. And Kremi walks through how she restructured email programs for two very different B2B brands and cut unsubscribe rates by 20% while lifting click-through rates by 40%.

Timestamps

(00:00) - - Intro

(06:53) - - Ben Wallis: personalized year-in-review email campaign for every customer

(17:22) - - Jaina Mistry: why B2B newsletters are the most slept-on trust channel

(30:25) - - The operating model that makes publishing 52 newsletters a year sustainable

(30:45) - - Tyler Cook: the AI-powered newsjacking system that goes from trend to sent in under an hour

(42:27) - - Kremi Mestanova: restructuring email programs for two very different B2B brands

(51:45) - - Live Q&A

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. 

Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn more at vector.co, and get their new MCP server by clicking here. 

Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.

Visit hatch.fm to learn more