Are events worth the cost? (Dave’s Newsletter)

ARE EVENTS WORTH THE COST?

The Real ROI of Events (It’s Not What You Think)

I’ve spent the last six years working from home. And I’m finally ready to admit something:

It gets lonely.

There’s something that just feels off about spending the whole day on video calls, messaging apps, and talking to AI assistants (hi Claude, if you’re listening).

I close my laptop at the end of the day and feel… empty.

But last weekend we had all of our neighbors and their kids over for brunch. Spent two hours laughing and trading stories around the kitchen table. And I felt this buzz afterwards that I couldn’t quite explain. There’s something about making eye contact, reading body language, and just being in the same room with people. We were wired for it.

Do you know what I mean? I can’t be alone here. The computer just doesn’t feel the same as being in-person.

And I think this directly relates to why events are such a powerful marketing channel right now.

People are craving real connection. And the companies that figure out how to create it are going to build something their competitors can’t copy.

At Exit Five, we went all in on events this year. We’ve now run our flagship event, Drive, twice — sold out both years. We’re doing it again in September 2026, same venue in Vermont, scaling from 250 to 400 people. Plus we’re running dozens of smaller events around the country.

We’ve made a lot of mistakes along the way and you know that events can be incredibly stressful and agonizing. But after two years we’re starting to build a real events playbook, and we thought it would be fun to share some of our biggest lessons in this week’s newsletter.

Here are six things we’ve learned from a year of running events.

1. Start With the Landing Page, Not the Logistics

This might sound backwards, but we start every event with the landing page. Before the venue, before the speakers, before any of the logistics.

It’s an incredible forcing function. Starting with the landing page forces you to answer the hard questions first: What is this event? Who is it for? Why should a senior marketer take two days out of their calendar to be there? What will they walk away with that they can’t get from a podcast or a Slack thread? What’s the headline here?

If you can nail that messaging on the page, everything downstream gets easier — speaker selection, session format, pricing, all of it. The landing page becomes your north star.

2. Treat Your Event Like a Product, Not a Campaign

This is the mental model shift that changed everything for us: we stopped treating Drive like a one-off campaign and started treating it like it’s own product.

Campaigns end. Products iterate.

After Drive 2024, we surveyed every single attendee. Not a two-question NPS form — a real survey asking what worked, what didn’t, and what they’d change. Then we read every response. All of them. Even the painful ones.

The feedback was specific. People wanted more unstructured time to connect. They wanted smaller group formats. They didn’t want to sit in a conference room for eight hours.

So we rebuilt Drive 2025 around that input. We added structured small group sessions of 8–10 people. We built in long breaks. We added a golf outing, hiking excursions, and axe throwing — not as filler, but as environments designed for real conversation.

That’s the product loop: ship, get feedback, improve, repeat. It compounds. Each year the event gets meaningfully better because it’s built on real data from the people who were actually there.

3. Design for the Conversations That Happen Between Sessions

The best moments at Drive didn’t happen during the keynotes or panels. They happened at breakfast. At August First - the coffee shop around the corner. At the hotel bar at 11 PM.

We call these “third spaces” — not the stage, not the breakout room, but the informal gaps where people actually talk to each other without an agenda.

Once we realized that, we started designing for it on purpose. Long breaks. Meals that aren’t rushed. Opt-in excursions where people spend two or three hours together doing something that has nothing to do with marketing.

One attendee told us she made three close professional connections on the hike — people she’s still talking to weekly, six months later. You can’t force that outcome. But you can create the conditions for it. We’re building Drive 2026 around this idea and being much more intentional with it.

4. Your Attendees Can Provide Better Content Than Your Speakers

We had great speakers at Drive. Panels, fireside chats, the whole lineup. But the most valuable sessions were the small group discussions where 8–10 marketers sat in a room and worked through real problems together. If I had hair I would be pulling it out. We spent all this time sweating the speakers and the agenda, and the big ROI came from connection.

The breakouts had no slides. No presentations. Just a VP of Marketing at a Series B company saying “We’re trying to figure out attribution and nothing is working” and six other people in the room who’ve actually solved that problem sharing what they did.

That format was the highest-rated part of both years. If you’ve curated the room well, your attendees are the most valuable content asset in the building. Your job is to facilitate the exchange, not broadcast at them.

5. The Event Doesn’t End When You Leave The Venue

One thing we learned after the first year of the event was just how much “post” event work we needed to do. There’s all the content from the event, the follow up emails, surveys. You come off the high from the event and immediately are behind on work again. So for Drive 2025 we had a better plan for follow up heading into the event.

We captured professional photos, video clips, and recap content at Drive — and pushed it out the same day. Not a week later. The same day or the next morning, while the energy is still real.

This matters more than people think. Wait a week and your attendees are back in their inboxes, buried in Slack, moving on to the next thing. Hit them while the experience is fresh — with content they want to share, tag themselves in, and forward to their boss as justification for next year’s ticket.

We also make introductions during the event, deliberately. “Hey, you’re both running demand gen at companies doing $20M ARR — you should talk.” That’s not small talk. That’s part of running a great event.

6. Community Is the Real ROI

Events are expensive. They’re operationally complex. And if you’re trying to measure ROI purely in pipeline sourced and deals closed, you’re going to have a hard time making the math work.

But here’s what I’ve seen after two years of running Drive: someone met their next hire there. Someone else found a mentor who helped them navigate a career transition. A third person closed a six-figure deal with someone they sat next to at dinner.

That’s the real ROI. Not a scan at a booth. Not a MQL in your CRM. Relationships that compound over years.

And it goes back to that feeling I had at the kitchen table on Sunday. We were wired to connect with people in real life. The companies that build events around that truth are going to win.

We had no clue what we were doing in year one. We figured it out by doing it, getting honest feedback, and iterating. If you’re thinking about running events for your company, just start. The playbook builds itself once you’re in motion.

– Dave

P.S. Are you running events at your company in 2026? I want to hear what’s working, what’s not, and where you’re investing. Hit reply and tell me about your event strategy.