The Dave Gerhardt Show (from Exit Five)

#372 | Dave sits down with Jay Schwedelson, founder of subjectline.com and Guru Media Hub, one of the sharpest tactical minds in email, webinars, and live content. Jay explains why so many B2B marketers get live content wrong from the very first step, and how small shifts in packaging can completely change who shows up and who doesn't. They dig into the psychology behind when people actually open and engage with email, why shorter almost always wins, and the habits that quietly keep you out of the spam folder. Jay also shares the specific email and send-day habits he swears by, a few of his go-to tricks for getting people to actually reply, and how he thinks about testing your way to what works for your own audience.
Timestamps

(00:00) - – Why "webinar" might be costing you registrations

(01:12) - – Meet Jay Schwedelson and the virtual event he built to 30,000 people

(06:26) - – A simple trick to get more people to actually show up live

(08:44) - – Why giving everything away on-demand might be a mistake

(10:23) - – The case for live, human connection in an AI-saturated world

(13:00) - – The send times most B2B marketers are sleeping on

(15:18) - – How to package and name your content so people actually want it

(22:02) - – The newsletter habit that makes people stick around

(26:09) - – Small email tweaks that quietly boost open rates and deliverability

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:
Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.
Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.
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.
Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.

***

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

#371 | Most B2B companies gate everything and hide their pricing. Funnel Leasing does neither, and grew from $3 million to $50 million in revenue anyway. Dave sits down with Alex Howe, SVP of Marketing and Growth at Funnel Leasing, to talk about how he built that growth engine with no marketing background, no paid ads, and no sales team pressure. They get into why his whole philosophy is built around being different rather than better, why ungating everything (including pricing) builds more trust than gating ever could, and how to prove marketing is working without hard metrics like a two-week sales cycle. Plus: how a background in political PR shaped his approach to getting attention, the event marketing stunts that actually got prospects talking, and why messaging should keep evolving without ever losing its core story.
Timestamps

(00:00) - - Introduction

(05:32) - - Be Different, Not Just Better

(09:13) - - Why You Should Ungate Everything, Including Pricing

(13:34) - - How to Prove Marketing Is Working Without Hard Metrics

(18:38) - - A Great Product Makes Marketing Easier

(24:54) - - Build a Point of View by Staying Close to Your Customers

(27:10) - - Creative Event Marketing Beats a Boring Booth

(31:00) - - What a PR Background Teaches You About Getting Attention

(35:59) - - Hire Specialists and Give Them Ownership

(39:00) - - Why Differentiation Matters More Than Ever in the AI Era

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:
Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.
Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.
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.
Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.

***

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

#370 | Most B2B marketers have no idea you can run TV ads for $50 a day. Dave sits down with TV advertising veteran Amit Sharan, SVP of Marketing at Tatari, to talk about this, and how to think about CTV as a B2B channel. They get into the difference between linear and streaming, why programmatic buying only reaches 15% of total TV inventory, and the case for retargeting your website visitors on TV instead of just running more ads on LinkedIn. They also get into what makes TV creative actually work, where AI fits into that process, how to measure performance without relying on last-click, and why it's worth testing a channel you've never touched before.
Timestamps

(00:00) - - Why B2B marketers are sleeping on TV ads

(01:17) - - Getting into ad tech: video advertising, Facebook, and a $450M acquisition

(07:03) - - How to cold-apply your way into a company you want to join

(09:05) - - What scale looks like for a modern TV ad platform

(11:02) - - The three buckets of marketing: demand gen, product, and corporate

(13:59) - - How to actually measure whether your brand is working

(16:12) - - Why marketers respect good marketing more than any celebrity spokesperson

(20:04) - - CTV 101: linear vs streaming, and why programmatic only touches 15% of inventory

(25:03) - - The $50-a-day move: retargeting website visitors on CTV

(28:07) - - What actually makes TV creative work

(33:42) - - Should you use AI-generated video for your ads?

(37:21) - - Measuring TV without relying on last-click

(38:19) - - Testing new channels: the case for trying something you've never done

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:
Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.
Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.
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.
Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.

***

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

#369 | It's hard to know what works and what doesn't, what's real and what's not right now. So we tapped 9 B2B marketing pros, all specialists in their area, to share one thing that's produced real results so far this year. Here's how it works: 9 speakers, one play each, two minutes on the clock. When host Dave Gerhardt hits the buzzer, it's on to the next play. The audience votes on their favorites, and the top plays come back for a second round with more detail. 60 minutes of back-to-back insights across demand gen, content, brand, social, product marketing, strategy, and more, featuring plays from senior marketing leaders at companies like Snowflake, Sprout Social, Tekmetric, Lendio, and many more.
Timestamps

(02:23) - - Nine marketers, two minutes each, one play — welcome to the B2B Blitz

(07:23) - - 6x podcast engagement with comic-style clips, Jess Cook (Vector)

(09:41) - - Adapting core messaging across different segments, Diane Wiredu (Lion Words)

(11:43) - - Turning win-loss research into pipeline recovery, Drew Giovannoli (BuriedWins)

(13:28) - - An AI-powered voice-of-customer system built from sales calls, Jonathan Rosenfeld (Hologram)

(16:09) - - Treating your internal team like a demand gen channel, Hunter Talpas (Tekmetric)

(19:23) - - A revenue-first framework for campaign planning, Hailey McDonald (Sprout Social)

(21:27) - - AI messaging tests that delivered an 8x CTR lift, Casey Patterson (Snowflake)

(23:23) - - Putting AEs in the ad to build familiarity before outreach, Spencer Rule (Lendio)

(25:30) - - Automating LinkedIn ads with Claude Code, Anthony Blatner (Speedwork)

(40:51) - - The winning play, round two: AE-led video ads in depth, Spencer Rule (Lendio)

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:
Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.
Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.
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.
Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.

***

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

#368 | Dave sits down with Jonathan Hunt, VP of Content and Media at HubSpot, to talk about what it means to run a media company inside a software company, and why that framing changes everything about how you build a content team. Jonathan runs a 70-person operation reaching 50 million people a month across 17 YouTube channels and a creator network of 150. They get into how HubSpot thinks about the three jobs of content (demand gen, influence, and earned media value), why gated PDFs are dead and what's replacing them, how Jonathan's team built an AI clipping engine in a six-week sprint, and how to tell the measurement story to a public company's CFO. Plus: what Jonathan looks for when hiring, how creator partnerships actually work at scale, and why "creative freedom" without strategy is just chaos.
Timestamps

(00:00) - - - Jonathan Hunt, VP of Content and Media at HubSpot

(03:17) - - - Running a media company inside a software company

(07:47) - - - From the HubSpot blog to a network of 150 creators

(11:22) - - - How to find creators (and the tool Jonathan recommends)

(12:39) - - - The three jobs of content: demand gen, influence, and earned media value

(17:22) - - - How to tell the measurement story to your CFO

(20:42) - - - Why gated PDFs are dead and what converts now

(24:00) - - - What actually works in creator partnerships

(31:21) - - - The AI clipping engine HubSpot built in six weeks

(45:38) - - - HubSpot's public code of ethics for AI use

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:
Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.
Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.
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.
Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.

***

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