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.