The small-event strategy that outperforms $60k sponsorships

Here's the thing about events: you can plan everything perfectly, and it still won't go according to plan.

Four months of planning. A five-star restaurant. Seventeen carefully selected prospects and customers. A $15k investment. Everything was set for Thursday night.

Then Wednesday afternoon. Mid-breakout session. A contract mix-up. The boat cruise date was wrong. Our dinner? Had to be tonight. In three hours.

Cool cool cool. 

It’s-so-not-cool.

In the Season 2, Episode 3 of This Meeting Could've Been a Podcast, Josh and I walk through how we pulled off one of our most successful events ever—with almost no notice, a frantically rewritten seating chart, and zero time to spiral. 

Okay, we had three hours.

What you’ll learn

• Why small, intimate dinners beat massive trade show booths (especially when you're not Hubspot)
• How to reverse-engineer an anonymized attendee list into actionable prospect data
• The power of strategic customer seating—and why letting them do the selling is way more effective than any pitch
• What to do when your meticulously planned event gets blown up three hours before go-time
• Why authenticity beats perfection, and how a chaotic scramble truly made the night better

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TOP THREE TAKEAWAYS

Takeaway 1: Only sponsor the big events when someone would notice you're missing

When I looked at the Drive sponsorship options, there was no way we were going for a $60k title sponsorship. That's just not where we are as a company.

The only way I'd ever want to show up in full force at a massive event is if we had such an enormous, well-known global brand that it would feel wrong if we weren't there. Someone would notice we were missing.

At this stage? A booth at a giant conference feels like lighting money on fire.

So we went small. Intimate. A 20-person dinner at Drive. A co-hosted event with UserGems at Inbound. Events where we could actually build relationships, not just hand out stickers.

Small doesn't mean less effective. It means strategic. Pick the events where you can own the room—not rent a corner of it.

Takeaway 2: Let your customers sell for you—it's way more authentic

Here's what happened when we brought our customers to our dinner: we didn't talk about Vector the entire night.

Josh and I barely had to say a word. I know, crazy for us. We'd walk around and hear our customers talking to prospects about what they're doing with us, how they're using Vector, what's working.

And it was so much more authentic than if we'd stood up and pitched.

Natalie Taylor from Capsule taught me this: bring customers to your dinners and seat them strategically. Let them tell your story. It's more credible, more genuine, and way more powerful.

If a customer shows up to your event and willingly talks about your product? That says everything.

Takeaway 3: Selling less = selling more (when authenticity leads)

The world is hungry for authenticity. That's why small-format events work. That's why dinners work. That's why our chaotic scramble worked.

We brought marketers, not sellers. We had real conversations about families and weird documentaries, not product roadmaps. We didn't force a pitch. We just let the night unfold.

And by selling less, we ironically sold more.

Nearly 100% conversion in pipeline opportunities came out of that dinner. The follow-up was effortless—just LinkedIn DMs saying "thanks for coming" that turned into demo requests.

When you stop trying to control every moment and just create space for authentic connection, people want to work with you more.

The best $15k that we’ve ever spent

Yes, we had to pull this off in three hours. Yes, nothing went completely to plan. And yes, not everyone came (turns out – they weren’t ever there).

But the chaos made it better.

The vibe wasn't stiff or formal—it was "we're all figuring this out together." People gave us brownie points for executing under pressure.

And honestly? I want the boat mix-up package at every event now. It's worth the heart palpitations.

And maybe one day Josh will see Vector’s name in lights.

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