The Dave Gerhardt Show

Episode: Behind the Scenes of Drive 2025 with Anna Vermillion and Allison Saxon

Date: October 16, 2025
Host: Dave Gerhardt
Guests: Anna Vermillion, Allison Saxon

Episode Overview

This episode pulls back the curtain on "Drive 2025," Exit 5's signature annual event, featuring core event strategists Anna Vermillion and Allison Saxon. The trio delivers candid insights into planning, executing, and evolving B2B events—touching on trends shaping event strategy, the importance of authentic community, and actionable lessons from both triumphs and mishaps. This isn’t a buttoned-up interview; it’s a lively, practical conversation designed for marketers, ops leaders, and anyone seeking to create more impactful live experiences.

Main Theme

Building Community-Centric Events in the AI Era:
Dave and his team discuss how Drive evolved from a casual meetup idea into a flagship event at Exit 5, fueled by trends like post-pandemic in-person connection and the existential need for authentic relationships in a digital, AI-driven world. They emphasize that success isn't about flashy venues or endless programming, but facilitating meaningful, memorable human interactions for marketing professionals.

Key Discussion Points & Insights

1. Why Events Matter Now More Than Ever

• Context: Remote work and AI are pushing professionals to seek real-world connection.
• Dave’s Perspective:

  “In our industry… I got so burnt out on doing events… but now you have so many people who couldn’t wait to get out of their house and needed an excuse to go travel and get out there for work.” — Dave, [05:10]

• Events feed not only knowledge and skills, but genuine community—giving marketers a sense of belonging with peers who understand their world.

2. What Sets Drive Apart from Traditional Conferences

• Anna’s Description:

  “It’s not your typical, you know, B2B conference. It’s not very buttoned up. …It’s really just a place for people to come connect, meet each other offline.” — Anna, [06:40]

• Emphasis on a casual, welcoming environment—less jargon, more friendship. Real-world meetups for a niche online community.
• Allison on Learning:

  “It’s still a place where you can learn tactical things… and take back to your work team like on the next Monday when you get back from Drive.” — Allison, [07:43]

• Dual purpose: tactical value and deep relationships.

3. The Role of Online Community as a Foundation

• Dave:

  “The reason we… didn’t just start this event because we wanted to… make a bunch of money… We did this because we had this online community now dating back three, four, five years…” — Dave, [09:14]

• Drive succeeds because it taps into an existing, active community with pent-up demand for in-person connection.

4. Planning: Start with the Offer, Not the Logistics

• Allison:

  “First step is definitely just build the landing page so you can get tickets out so you can start planning the other stuff.” — Allison, [11:28]

• Focus on story and value prop before getting lost in the weeds; logistics come after the pitch is clear.
• Dave:

  “It’s the business lesson of, like, begin with the end in mind. …Start with the offer, start with the landing page… Who’s going? What are you going to learn?” — Dave, [12:38]

5. Onboarding, Teamwork & Learning by Doing

• Throwing new hires directly into event planning boosted rapid skill-building and team chemistry.
• Anna:

  “You're depending on a dozen different people to move things forward for this event… getting kind of thrown into that… was like the perfect immersion…” — Anna, [16:17]

• Allison:

  “Having to do that with her really immersed me into working with you guys and everything. …It made drive planning easier for me…” — Allison, [17:13]

6. The Power of Signature Location & 'The Third Space'

• Keeping Drive in Vermont unintentionally became a “brand” component, delivering unique vibes and differentiating from drab hotel conferences.
• Group excursions and non-programmed time—like pickleball, yoga, and casual walks—replace marathon speaker lineups.
• Anna:

  “That’s kind of what these excursions are… spaces not the conference room where… you connect with people in your world outside of that.” — Anna, [22:02]

• The “third space”—not work, not home, but a community belonging.

7. Obsessing Over Details & Product Experience

• Even small amenities (“People were pumped because we had iced coffee!” — [29:09]) make a massive positive difference.
• Dave:

  “The best marketing thing is: have a damn good product. …If you obsess over the product and you have an awesome experience… people are going to take pictures, they’re going to tell your friends…” — Dave, [29:34]

8. Lessons From Things Going Wrong

• Allison on Documentation:

  “Document everything… if you ever have phone calls with [vendors], make sure you have it in writing…” — Allison, [32:46]

• Example: a boat party date mix-up and scramble to create a new experience last-minute; turned into a highlight.
• Dave:

  “Something will go wrong. It’s a fact. …The way you all handled that was amazing. That was the big, the big fuck up. But your lesson from that is like everything needs to be in writing…” — Dave, [34:54]

9. Post-Event Work & Long Tail of Value

• The event isn’t over when it ends; content, follow-ups, sponsor fulfillment all matter.
• Anna:

  “The event isn't over whenever it ends. …We have all this content, people are waiting on the slides, people are waiting on notes…” — Anna, [36:02]

• Measure success with both ticket sales and attendee NPS.

10. Top Practical Tips for Marketers Running Events

• Stay hyper-organized (spreadsheets, weekly meetings, delegation)
• Be assertive—follow up firmly with vendors (“You need to be Bridezilla…super alpha energy during those two days.” — Dave, [40:31])
• Anticipate attendee questions with clear, timely emails and a comprehensive info doc (“Start from the back…what was the very last email that we needed to send?” — Allison, [41:06])
• Don’t over-index on programming; leave room for organic connection.

Notable Quotes & Memorable Moments

• On Brand Experience:

  “That’s a huge learning. …We’re going to spend more on this event in 2026 than we spent on the entire company payroll… just to do this event this year.” — Dave, [19:55]

• On Human Connection:

  “At Drive, you don’t really have to explain all that. Everyone, like, really gets it. …Whether you’re a CMO or someone like me, very early on in your career, it doesn’t really matter because you belong because everyone speaks the same language.” — Anna, [28:04]

• Vibe Over Polish:

  “Not being so damn serious, maybe that’s part of our brand. …Part of our brand is to be very real and authentic about things…if something goes wrong, everyone’s not like, boo.” — Dave, [46:36]

• Funniest Moment:

  “Whenever we were at the brewery that night, …I was looking down at my phone while I was walking, and there was, like, a glass door… and I completely ran into it. …But it was really embarrassing.” — Anna, [45:06]

Rapid-Fire Learnings

• Biggest Learning:
  • “Document everything…in writing.” — Allison, [32:45]
  • “The event isn’t over when it ends… the strategy following the event [is huge].” — Anna, [36:02]

Timed Highlights

• [05:10] — Why In-person Events Are Rising Again
• [06:40] — What Makes Drive Different (Casual & Human)
• [11:28] — Event Planning: Always Start With the Landing Page
• [16:17] — Onboarding by Doing: How Events Build Team Culture Fast
• [19:55] — Establishing the Venue as Part of Event Brand
• [22:02] — The “Third Space” Explained
• [29:09] — Why Little Details (Iced Coffee!) Matter
• [32:45] — Major Learning: Document Everything With Vendors
• [36:02] — The Event’s “Long Tail” (Post-event Follow-up)
• [41:06] — Pro Email & Communication Planning
• [45:06] — Brewery Glass Door Accident (Funniest Moment)
• [46:36] — Embracing Improv and Authenticity

Practical Takeaways for Marketers & Event Planners

• Start with a compelling offer and clear value proposition before worrying about logistics.
• Community roots drive event success—invest in your digital audience first.
• Meticulous documentation, assertivity with vendors, and backup plans are non-negotiable.
• Lean into “third spaces” and unprogrammed time to spark real connection.
• Post-event follow-up—content, sponsor recaps, and attendee surveys—are as critical as the event itself.
• Sweat the details (catering, amenities, environment) as much as the agenda.
• Be real, flexible, and authentic—the energy you bring is as important as the program.

Standout Moments & Shoutouts

• Boat Party Mix-up (handled last-minute, turned into a great story) [34:33]
• Excursions and spontaneous adventures (breakfasts, brewery trip, on-site yoga) fueled attendee bonding [24:09]
• Shoutouts to attendees and team—Diane from Barcelona, Chelsea, speakers like Harry Dry, and many others [49:04-51:27]
• The feeling of relief and camaraderie after packing up, tossing event debris, and finally resting [43:24]

Closing

Drive is returning for 2026 at Spruce Peak, Stowe, Vermont, with plans for even more immersive, connected experiences. The team highlights that meaningful events start with community, product-quality obsessiveness, and a willingness to do things differently—always focused on what attendees would love (and not what tradition dictates).

Pressure is a privilege. The bar is high, and the Exit 5 team intends to raise it again.

Find Allison and Anna on LinkedIn—and, as Dave notes, try to poach them at your peril! Questions or interest in future behind-the-scenes episodes? Email the Exit 5 team.

[End of summary]