7 Things I’ve Learned About Running Events (That Nobody Tells You)

If you’d told me in late 2023 that I’d be running a multi-day conference with 100+ attendees or generating profit from events, I would’ve spit out my coffee. Up until that point my decade-long “event planning resume” was mostly casual meetups in borrowed office space and dinners where I was footing the bill.

Fast forward to March 2025, and holy cow, things look completely different. It’s been 15 months since my first profitable event, and here’s what I’ve figured out along the way:

1. The “Free Event” Problem

If you’re trying to run profitable events in the startup ecosystem, you’re competing with a bazillion free gatherings where someone donates space and another covers pizza and beer.

So your event value proposition has to answer:

Why the heck should someone pay for your event when they could network for free somewhere else tomorrow?

2. Charging a Little (Changes A Lot)

Slapping even a small ticket price on your event transforms who shows up and how they engage.

I’ve seen this time and time again. People value what they pay for.

But beware! You may get flak from folks who aren’t used to getting charged for certain types of events (that 2-hour “after work format” – I’m looking at you!)

If you’re sensitive to that, you can also try the “charge but refund upon attendance” approach. After all, people are motivated to avoid losing something they already have.

3. Be the Active Connection-Maker

A few minutes after walking into a packed FIF Collective dinner, Meg McKenna came up to me and asked point-blank:

“Who do you want to meet?”

Five minutes later, I was talking with the one person I’d been hoping to bump into. And that made my night.

Think about how you can create that kind of “Wow” connection for your attendees as well as for your sponsors.

4. Teamwork Makes The Dreamwork

Event planning and execution requires a ton of collaboration across your company. Your sales team, your ops team, and your leadership team need to be in lockstep.

What’s super cool about this is that an event helps your team bond around a shared goal and a date that typically can’t be moved. The cherry on top is the sense of accomplishment they’ll get when they’re watching attendees and sponsors enjoy the event – that they made happen.

5. Sponsors Want Their Space

For smaller events, sponsors are going to want exclusivity within their category. This shouldn’t affect your profitability but it does make your sponsorship sales process a bit more complicated.

For massive conferences, you might see multiple sponsors from the same category, but you need serious FOMO to pull that off. After all, most of us don’t have Web Summit-level pull!

6. Great Experiences != Big Budgets

Our recent Jeffersonian dinner with startup CEOs wasn’t sponsored or expensive. What made it special was bringing the right folks together around a focused conversation.

7. Document Everything

Candid moments of connection sell your next event better than any pitch deck. So make sure to snap some photos and track social media posts too—they’re public testimonials which you can point potential sponsors at when they’re considering working with you.

And yes, an iPhone camera works fine for this. But if you’re just getting started on your event journey, consider a splurge and hire a photographer to come in for an hour and take some pics. You’re pretty much guaranteed to get a few solid shots that will look great in your promotional materials.

Running a startup event you’d like to scale? Or have an event concept that might align with our community? Let us know!