How we designed an owned event series that generated $880K in pipeline

Chili Piper has ChiliPalooza. Drift has Hypergrowth. Every SaaS CEO not-so-secretly wants their own version — a flagship event with their name all over it. Josh was no different. The problem? Me.

A 5,000-person conference felt a little ambitious. And the Slack community Josh wanted to go alongside it? That's a full-time job nobody had time for.

Josh didn't get his ChiliPalooza.

But we found our version of it. Specifically: a private dinner, a haunted walking tour, and $880K in projected pipeline.

In this episode of This Meeting Could've Been a Podcast, Josh and I break down how the Ghost Tour Tour came to life — the strategy, the budget, and yes, the T-shirt drama.

What you’ll learn 

• The case for small, repeatable events over big owned conferences
• Why community is a retention play not a growth play
• The Ghost Tour Tour concept and why only Vector could pull it off
• The invite request strategy and why it worked
• The outreach playbook: why I sent every single invite one by one — and would do it again
• How I built the landing page in one evening with Claude
• Why events are one of the easier channels to measure — and what our numbers look like

TOP THREE TAKEAWAYS

Takeaway 1: Community is a retention play. If you're in growth mode, events win

Josh wanted a community. He'd even run a poll, and customers were asking where they could talk to other users. The demand felt real. The timing didn't.

Because a community done badly is very public. And the pitch fest problem is real — the second it starts happening, you can't pull it back. You're left holding something that very visibly didn't work. If you can't put a full-time person on it to own the content, moderate the conversations, and keep the wolves out, just don't do it yet.

But the resource question wasn't even the biggest thing for us. It was the stage. Where are you in your journey, and what does success look like right now? For us, growth is the goal. New pipeline, new conversations, new customers. Community is powerful, but it serves the people you already have. Right now, we need events to put us in front of the people we haven't met yet.

Community will happen. Josh won't let it not happen. But right now? Retention or growth. Start there.

Takeaway 2: Some things aren't meant to scale. Do them anyway

The outreach for the Ghost Tour Tour was strictly one-to-one emails from our Google accounts.

Kelly took the senior demand gen folks, I took the CMOs and VPs. Personal, considered, and yes — completely unscalable.

And I'd love to tell you there's a smarter way to fill a 20-person event with exactly the right people. I’ll get back to you on that one. You're not trying to reach thousands of people. You're trying to get a very calculated balance — people who are already at a conference, already fielding four other dinner invites, and fully weighing up whether DoorDash to the hotel room is the move.

It is, by the way. You can order way more food than is socially acceptable, and nobody knows.

So you're competing with that. Nobody wants to be the person at a conference with no dinner plans — but they also need a reason to pick yours over the open bar at the Marriott. A mass email doesn't give them that reason. A personal one from the right person just might.

Not everything needs to be a scalable system. And if filling a room with the right people means sending emails one by one from your Google account at 11 pm? That's just Tuesday.

Takeaway 3: $45K in. $880K out. Events are one of the easier things to measure

Compared to most marketing channels, events are refreshingly simple to track. Someone was at the dinner. Then they booked a demo. You know exactly where that came from.

For the Ghost Tour Tour, the math looks like this. Out of the twenty people in the room, around twelve are prospects, the rest are Vector employees and customers. If six of those twelve book a meeting, that's $220,000 in pipeline per stop. Across all four events, we're looking at $880,000 in projected pipeline total.

And I think we might even surprise ourselves. Because when the experience is fun rather than a thinly veiled pitch, people leave wanting to know more. The follow-up feels like their idea. The demo request lands in your inbox, and it doesn't feel transactional. It’s the natural next step after a really good night out with people you liked.

Haunted walking tours have been known to have that effect.

Catch the full episode (and subscribe to This Meeting Could’ve Been a Podcast) on YouTube or your favorite podcast platform.