The Dave Gerhardt Show · 1 Oct 2026 · From the week of 28 September
Dave & Dasha Live from Drive: Beating Brain Rot, Burnout, and Boredom After 15 Years in B2B
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Dasha, co-host of the show, interviews Dave Gerhardt, founder of Exit Five, live at the company's Drive event in Vermont. Dave covers how Drive started as a small first event, why the Vermont venue matters to the brand, and how he wrote his own opening keynote after an AI-built outline lacked soul and Harry Dry pushed him toward a personal story about connection. The conversation also covers how that process changed his feedback to the team, his view that most of the business's problems are who-problems rather than how-problems, and how the newsletter was rebuilt.
For founders
- Drive started as a first event at a Burlington, Vermont venue with a 200-person maximum, booked for roughly $1,500 on a credit card, with speakers the team already knew.
- Dave says event location is part of the brand, and that he nearly moved Drive to Boston before finding a Vermont resort venue.
- Dave says an AI-built talk outline had no soul, and that the talk only worked after a human storyteller pushed him to build it around one core idea.
- Dave says most of the business's problems are who rather than how problems, and that hiring, firing and onboarding have been painful and hard.
- Dave says Exit Five is a media company whose events and sponsorships are paid for because content is the product.
For revenue leaders
- Dave says last year's event sold 200 tickets with about 150 people on the waiting list, and this year's sold out at over 400 attendees.
- Dave says he now gives feedback by pointing to concrete examples and explaining the change he wants, rather than rewriting team members' drafts himself.
- Dave says founder feedback carries so much weight that a suggested headline can be read as the only acceptable one.
- Dave says the newsletter was first built from his LinkedIn posts, readers stopped loving it, and the team rebuilt it around other people's voices through podcasts and webinars.
- Dave says engagement has been off the charts since the content process was rebuilt, though he gave no figures.
What was said 14, most useful first
Feedback works better when it points to concrete examples than when the manager rewrites the draft. Listen
After working with Harry Dry, Dave says he now gives his team show-don't-tell feedback, pointing to specific examples such as a named place or story and cutting unnecessary material. He says he used to rewrite team members' drafts himself, and now explains how he wants it to look and lets them make the changes.
“I think I try to rewrite things too much for the team.”
Most business problems are who-problems rather than how-problems. Listen
Dave says Exit Five is a simple business that produces content, and that the team's ideas cannot be executed without the right people. He says hiring, firing and onboarding have been painful and emotional, and that the current nine-person team is really good, as each iteration of the team should be better.
“most of the problems with the business is mostly who not how problems.”
A first event can be tested in a small venue for roughly $1,500 in booking costs. Listen
Dave says Drive started at Hula, a Burlington, Vermont event space with a 200-person maximum, where booking cost about fifteen hundred dollars, though he said 'something like that.' The team picked speakers they already knew and did not run a large production. He says the first day's buzz from people meeting in person led them to take the event more seriously each year.
“Basically, you know, put fifteen hundred bucks on your credit card and, like, you can host an event here.”
Listen to the episode Pipeline & demand generation Link to this
Last year's event sold 200 tickets and left about 150 people on the waiting list. Listen
Dave says demand outgrew the Hula venue, which led the team to look for a bigger space. This year's event sold out, with capacity for over 400 attendees, and he says some people doubted the sellout was real.
“We sold two hundred tickets. Like, a hundred and fifty people on the waiting list”
Listen to the episode Pipeline & demand generation Link to this
The customer is not always right, which Dave considers a myth. Listen
Dave says he is very close to feedback as a marketer, but does not think customers are always right. He decided to host an event after enough of the right people said they would attend, which he describes as de-risking the decision.
“I don't think the customer is always right. I think that's a myth”
Event location can be part of a brand, not only a logistics choice. Listen
Dave says moving Drive to Boston would have made it just another event, and that the Vermont setting is central to the brand's identity and success. He points to the resort's pool, hot tub and hikes as making a big difference, and says the Vermont venue is expensive but a great place compared to what an event in Boston would cost.
“I think this event being in Vermont is such an important part of the brand and identity.”
A keynote outline generated with AI had no soul, so Dave had to rewrite it. Listen
Dave briefed Claude with a brief, examples and screenshots, had it build the outline, and drafted from it, but the draft had no soul. He says he then asked Harry Dry for help, and Harry told him to put Claude away and write the talk himself.
“Time to put away Claude and get into your own head.”
A story needs conflict, and a talk without tension does not hold attention. Listen
Dave says Harry Dry's core thesis from his previous Drive talk was that the key to a great story is conflict, and Harry judged Dave's draft as lacking it. Dave recalls a hook from Harry's talk, Usain Bolt chasing a tiger, and illustrates tension with Dasha driving down from Canada for her first Exit Five team meetup and finding the border closed late at night.
“Story, the key to telling a great story is conflict.”
A talk improved when it was narrowed to one core idea drawn from the speaker's own experience. Listen
Harry Dry helped Dave narrow his talk to connection, drawing on his experience moving from an in-office company at Drift to remote work, where AI tools reduced conversation further. His final slides are photos from his camera roll over ten years, and he says it is the best thing he has written because it is a real story.
“Harry helped me position my whole talk down to like, connection.”
Founder edits carry so much weight that a changed headline can be read as the only correct version. Listen
Dave says he learned at his last company that founder or CEO words carry a lot of weight, so when he changes a headline the team may take it as the one answer. He now says there are multiple ways to win and that the team's version does not have to be his.
“I think the founder words have a lot of weight.”
The newsletter was rebuilt around other people's voices after readers stopped responding to the founder's repurposed LinkedIn posts. Listen
Dave says the newsletter began by turning his LinkedIn posts into issues, which was okay, but readers eventually stopped loving it. The team brought on two content people, built a new process, and shifted toward podcast guests and webinars, which he describes as production work.
“eventually people were, like, not loving our newsletter.”
Exit Five charges for events and takes sponsors because its product is content. Listen
Dave says the company has always called itself a media company, and that it charges for events and takes sponsors because content is its product. He says the last year was the first in which he felt it was a serious media company, and that this raised the quality bar and the investment he wants to make.
“The reason we charge money for our events, and we have sponsors is because, like, that is our product is content.”
Dave expects a business with a distinct personality to matter more as AI spreads. Listen
Dave says there is a lot of nonsense around AI and business books, and he wants Exit Five to be a quirky, cool business with personality. He points to Ben & Jerry's as a brand that stayed true to itself while making money, and says that is how he thinks about the next Exit Five.
“I wanna have like, a quirky cool business that is, like, injected with personality. I think that's gonna be more important than ever”
His book was produced through a weekly editing process rather than ghostwriting. Listen
Dave says his book Founder Brand was done with a ghostwriter who was more of an editor, with a two-hour call every Tuesday for about six months. The editor helped piece together sections and pushed for more specificity, but Dave said he ended up writing much of the book himself.
“and we would do every Tuesday for, like, six months, two hours on the phone.”