The Dave Gerhardt Show
Episode: Dave Answers 15 Questions About Work and Life from the Exit Five Team
Date: October 27, 2025
Host: Dave Gerhardt
Episode Overview
In this solo episode, Dave Gerhardt, founder of Exit Five and former CMO, sits down to answer 15 wide-ranging questions from his team about work, life, marketing, reading habits, pet peeves, and more. With his characteristic candor, humor, and off-the-cuff style, Dave offers insights into his creative process, personal routines, and philosophies shaped by years in the marketing world.
Key Discussion Points & Insights
1. Dave’s LinkedIn Content Creation Process
Timestamps: 01:55–06:00
- Dave keeps a backlog of ideas in Apple Notes, posting once daily, ideally in the morning (6–9am ET).
- He prefers off-the-cuff writing over formulaic content and avoids over-scheduling posts due to lower engagement.
- Notes the increase in AI-generated content, and how he leans into authenticity and his own voice for differentiation.
- Quote:
“I think the way that I write is very not AI. And so I've been trying to lean into that and write more.” (04:50)
2. Checking Slack & Email
Timestamps: 06:01–08:10
- Admits to checking email less, as Slack is essential for team communication.
- Treats Slack as his main inbox, aiming for two main sweeps per day.
- Recognizes the need to limit screen time and “let things solve themselves.”
- Quote:
“The most important people that I can be responding to are my team, which is in Slack.” (06:35)
3. Reading & Listening Habits
Timestamps: 08:11–13:10
- Reads multiple books at once; no guilt in quitting books partway.
- Prefers a mix of business and pleasure reading, now including Harry Potter (inspired by his daughter), Project Hail Mary, and golf books.
- Audiobooks help him read more; credits Kindle and whisper sync for faster progress.
- Podcast recommendations: “No Laying Up” (golf) and comedian Theo Von.
- Quote:
“No one has ever gone broke from buying a book. And so if it's $12, $20, doesn't matter, I will buy it.” (09:34)
4. The Perfect Day
Timestamps: 13:11–15:30
- Fitness first: wakes around 5:30am, gym and rucking/hiking by 9am.
- Family time and 1–2 productive work tasks define a successful day.
- Stresses simplicity and routine over hustle-culture tropes.
- Quote:
“Physical activity makes me feel amazing, reduces stress, reduces anxiety, improves my mood, just makes me feel good.” (14:33)
5. Life Story in Four Minutes
Timestamps: 15:30–16:55
- Born in Worcester, MA; played baseball in college; career span includes PR agency, Constant Contact, Privy, HubSpot, Drift, and founding Exit Five.
- Family moved to Vermont in 2020.
6. Most-Desired Quality or Ability
Timestamps: 16:56–20:20
- Wishes for more patience, less impulsivity — both a gift and curse as an entrepreneur.
- Struggles with caring about others' opinions online; working on “not engaging.”
- Reflects on the impact of social media discourse.
- Quote:
“A wise man once told me, don't argue with fools because people from a distance can't tell who is who.” (20:06, quoting Jay-Z)
7. Most Embarrassing Work Memory
Timestamps: 17:44–18:30
- At 24, accidentally farted loudly during an open-office meeting — broke the ice with a “Whoops.”
- Emphasizes that embarrassing moments humanize us.
- Quote:
“I go up and I just let out the loudest accidental fart of my life. I can't believe I'm sharing this...” (17:47)
8. Favorite Book
Timestamps: 18:31–19:30
- No single favorite; most-gifted: The Daily Stoic by Ryan Holiday.
- Recently loved Paper Tiger by Tom Coyne (golf memoir).
9. Best Career Advice
Timestamps: 19:31–21:15
- From David Cancel at Drift: double down on your strengths vs. obsessing over weaknesses.
- Cites Managing Oneself by Peter Drucker.
- Quote:
“It's better to find something that you're good at and try to become one of the best in the world at that... versus trying to round yourself out.” (20:11)
10. Regaining Motivation When Unmotivated
Timestamps: 21:15–22:10
- Leans on gratitude and perspective, citing a friend who served in Afghanistan as motivation during tough work moments.
- Quote:
“Anytime, like, anything in my job is really not...not even a sliver as hard as that is. And so I try to have that mindset.” (21:25)
11. If You Could Transform Into Any Animal
Timestamps: 22:11–22:58
- Would pick a lion or cheetah for their power or speed; also jokes he’d be his dog, a Bernadoodle, for a cushy life.
12. Proving He's Human (Not AI)
Timestamps: 22:59–23:46
- Would rely on his humor and unique writing quirks; “AI is incredibly corny and strange.”
- Quote:
“My writing is very clearly not AI for some reason. By the way, what a diss today for someone to be like that. That's AI and you're like, no, no, I actually wrote that.” (23:30)
13. Biggest Pet Peeves
Timestamps: 23:47–24:56
- Lack of self-awareness, people who can’t read the room, and those without empathy.
- Light-hearted annoyance: “crusty old man” pointing over the glass at Chipotle.
- Quote:
“People who can’t read the room, people who don’t have empathy for others. There’s many ways that plays out, but self-awareness is the one.” (24:07)
14. Swapping Lives with a Team Member
Timestamps: 24:57–26:15
- Would choose Anna (24, for “youth”) or Dan (parent to younger kids).
- Nostalgic for simpler times, but grateful for current life.
15. Go-To Karaoke Song & Alternate Careers
Timestamps: 26:16–28:52
- Could rap “Forgot About Dre” perfectly, though unlikely to perform it.
- Dream jobs: DJ, golf announcer (“on course”), but if serious, would return to being a CMO or head of marketing.
Memorable Quotes
-
On LinkedIn & Authenticity:
“There's a lot of AI slop there and I think the way that I write is very not AI.” (04:50)
-
On Screen Time & Priorities:
“The most important people that I can be responding to are my team, which is in Slack.” (06:35)
-
On Reading:
“No one has ever gone broke from buying a book.” (09:34)
-
On Routine & Well-being:
“Physical activity makes me feel amazing, reduces stress, reduces anxiety, improves my mood, just makes me feel good.” (14:33)
-
On Career Growth:
“Double down on your strengths versus trying to round yourself out.” (20:11)
-
On Caring Less About Opinions:
“A wise man once told me, don't argue with fools because people from a distance can't tell who is who.” (20:06, quoting Jay-Z)
Tone & Style
Dave’s answers are conversational, candid, and frequently self-deprecating. He mixes practical marketing wisdom with personal anecdotes and humor, often poking fun at himself or common industry foibles. There’s a steady undercurrent of gratitude—for his work, team, and family—that tempers his venting about online drama or pet peeves.
Timestamps for Important Segments
- 01:55 – LinkedIn content creation
- 06:01 – Slack and email usage
- 08:11 – Current reading/listening
- 13:11 – Perfect day
- 15:30 – Life story
- 16:56 – Desired qualities, opinions, and patience
- 17:44 – Embarrassing work memory
- 18:31 – Favorite book(s)
- 19:31 – Best career advice
- 21:15 – Regaining motivation
- 22:11 – Animal transformation
- 22:59 – Proving humanity over text
- 23:47 – Pet peeves
- 24:57 – Swapping lives with team
- 26:16 – Alternate job/karaoke
Summary
For marketers, entrepreneurs, and fans of Dave’s “real talk,” this episode delivers laughs, relatable moments, and actionable career wisdom in equal measure. The AMA-style format pulls back the curtain on both the daily habits and deeper motivations of one of B2B marketing’s most recognizable personalities—complete with fart stories, Jay-Z wisdom, and yes, musings on what animal he’d be.
