Why We’re Retiring Drive (Plus Dan’s Learnings From 3 Years As Exit Five CEO)

Over the past three years, 800 people flew to Vermont from as far as Hawaii, India, and Israel for a conference about B2B marketing. That is not normal. The first year sold out in 24 hours, and we grew from 100 people to 400 this year.

We’re retiring it anyway. I know, I know. Haven’t we read the business books? Double down, keep the main thing, the main thing. Dan and I are always passing business books back and forth, and one that’s stood out is Ben Horowitz’s The Hard Thing About Hard Things. Just because something works doesn’t mean we should keep doing it, and retiring Drive is one of those hard things. Here are the three reasons we made the call.

1. We Want Our Best Work In Front Of You All Year, Not Just Three Days In Vermont

Putting on an event like Drive is candidly a lot of freaking work. It becomes a year-round, full-time job for a bunch of the team (ask Dan, Allison, and Anna). It’s basically like planning a wedding for 400 people every year. You’re juggling speakers, sponsors, travel, contracts, venues, dietary restrictions, AV, and the crazy Frenchman who wants to bring a local jazz band to his keynote at the last minute (True story. We love you, Louis). We carry that stress 300 days out of the year.

We’re still doing events. But we asked ourselves a question: what if we applied that same level of effort to smaller, more frequent events across the country? Our mission is to be the number one resource for B2B marketing teams and CMOs. That can’t only happen at a three-day event in Vermont. And since we never raised $10 or $20 million in venture capital, we have to pick and choose which initiatives we carry out.

2. Turning Drive Into A Trade Show Would Kill The Magic

After Drive this year, we realized we were at a crossroads. Drive was stuck somewhere between a community meetup and a trade show. We had all the ingredients to make it 600 people, then 1,000 the year after. But after some introspection, we realized that a trade show is not the thing we want to build.

On the pod, Dan said he can’t say exactly where an “un-conference” ends and a trade show begins, but he knows the difference the second he walks in the room. At a 1,000-person event, you meet someone once and probably never see them again. At an Exit Five event, we want you to run into the same person a few times and get to know them. Once you get much bigger than a few hundred people, you lose that.

3. Instead Of Asking You To Come To Us, We’re Coming To You

We’re a community business, which means we’re a people business, something Dan often reminds the team. So we’re rebuilding our event strategy around hub cities like Boston, New York, San Francisco, Toronto, and Austin (I can already hear you in the comments about Chicago and the UK. We’ll get there). You’re welcome at any of them, even if you don’t live there.

Here’s what our events might look like in 2027:

• A happy hour with 100 marketers from our community on a spring afternoon in Boston.
• A morning breakfast in New York for CMOs on AI transformation.
• An off-the-record half-day working session in Austin for B2B marketing leaders. No video and no AI note takers, just what’s really going on inside their companies.

We got a preview of this last month in New York (and recorded a live podcast with Varonis’ CMO Rob Sobers). It was a huge hit. We looked around and thought, why don’t we do this five or six times a year?

Live from NYC: 100 B2B marketers joined us for networking and an exclusive live podcast recording with Rob Sobers, CMO of Varonis.

Then there’s our Marketing Leadership Retreat, March 1-3 in Scottsdale. It brings together 150 in-house marketing execs, with peer-led breakouts matched by role, company size, and go-to-market motion. Keynotes are Alice de Courcy (CMO, ZoomInfo) and Ethan Braden (CMO, Texas A&M), and our guy Dave Kellogg (EIR, Balderton Capital) is coming back.

So for 2027, it’s more cities, more often, closer to home. We’re retiring Drive partly because of how much work it was, and now that I’ve written out the 2027 plan, there’s no way this is going to be less work. We’ll figure it out. Thanks for the memories, Drive. See you on the road next year.

Marketing Leadership Retreat is back on March 1-3, 2027 (Scottsdale, AZ)

Bonus: Dan’s Top 5 Lessons As Exit Five CEO

Since I had Dan on the pod, I made it a two-for-one and put him in the hot seat. He came to Exit Five as a former VP of Marketing, joined what was supposed to be a nice little lifestyle business, and became CEO about a year ago (not on his bingo card, he told me). Here’s the rapid-fire version of what he’s learned running the business.

1. Give big initiatives a fun name to fire up the team.

Our annual KPIs are called the Five Card, and the pitch competition at our upcoming Miami offsite is the Five Fund. Once something has a name, it becomes a real thing people get behind.

2. No recurring one-on-ones.

Mondays and Fridays are for meetings. That leaves Tuesday through Thursday for deep work for everyone, Dan included.

3. Plan for how fast your buyers are changing.

Progress moves slower than you think, especially in B2B. Two years ago, everyone was nervous that marketing jobs would be gone within 18 months. Instead, our job board and executive community are busier than ever, and we doubled our team this year.

4. Wherever your feet are, be there.

Dan has a 2-year-old and a 10-month-old. Mornings are for working out, the workday is for work, and evenings are for his kids. Strong tie in to one of our favorite Exit Five Leadership Principles here: Work to live, don’t live to work.

5. Lightning round

(not a lesson but just things I want to know):

• Typical breakfast: Black coffee.
• Best book lately: Very Good Copy by Eddie Shleyner. We sent it to the whole team.
• Pet peeve: Parents speeding down his street past the elementary school. After a run, he stands in his driveway in his sunglasses with his dog (who looks like a police dog) and stares them down.

Three years ago, I asked Dan for one year at Exit Five. Now he’s angling for a lifetime contract, because, as he put it, “we’re married to this business.” I’ll have to check with the board. Thanks for the last three years, Dan. Here are the official Drive announcement and YouTube episode if you want to check them out.