Hi friends - Happy Sunday! This is another revamped piece from 2024. I’m building on my original framework and bringing it up to speed for today’s market, because conferences are having a comeback.
AI is pushing people back into rooms with each other.
Don’t get me wrong. I think AI is amazing in so many ways, and I use it every single day. But it’s also made a lot of us feel more disconnected.
Inboxes are flooded with AI-written outreach. LinkedIn feeds are full of posts that all sound the same. So many marketing efforts feel less and less human. And when everything digital starts to blur together, a real conversation over coffee (or a glass of wine 🍷) stands out more than ever.
The data backs this up:
In-person is winning on effectiveness. B2B marketers rated in-person events the most effective content distribution channel (52%), and events and experiential marketing are the second-biggest planned budget increase for 2026, right behind AI tools (Content Marketing Institute).
Face time builds trust. 77% of attendees say they trust a brand more after an in-person interaction (B2B Events Intelligence Report 2026).
So yes — in-person events are a real GTM lever right now. But they’re also one of the fastest ways to light money (and your most precious resource, your time) on fire.
The test I use with every founder is simple: if you can’t realistically generate 5x what it costs you to go, don’t go. First, I’ll walk you through the ways to stack the odds in your favor. Then we’ll run through the math.
Let’s dig in.
Build your conference calendar all at once (not one event at a time)
Most founders evaluate conferences one by one, as the invites and FOMO roll in. That’s how you end up at three mediocre events and less than desirable ROI.
Instead, here’s the process I run with the startups I work with — once a year, ideally in Q4 for the year ahead:
Make a list of every conference you could plausibly attend this year. Industry events, the shows your ICP goes to, regional events in cities where your customers cluster. Cast a wide net — you’ll cut it down later.
Identify which ones have an open call for speakers. Many do, and the deadlines often close months before the event. Track every deadline so you don’t miss them.
Submit for every speaking opportunity that fits. Panels, keynotes, workshops, moderator slots. Recycle your best pitches — one strong talk idea can be tailored to five events.
Collect the answers in one place. Who accepted you? Is speaking free, or does it require a sponsorship to get on stage? Which organizers offered a roundtable or a dinner slot instead? Which ones will share last year’s attendee list?
Prioritize based on visibility and impact. Now you’re comparing real options, not hypotheticals. Rank each event by where you get maximum visibility (stage time, a hosted room) or maximum impact (density of your ICP, meetings you can book) — then run your top picks through the 5x rule (more on that below). Before you finalize, gut-check the list with your customers and partners (more on that below).
Collecting all of this data up front is a game-changer. You stop reacting to whatever lands in your inbox and start choosing the handful of events that will actually move pipeline.
Land the speaking slots
You can get added to a panel as a speaker or moderator more often than you’d expect — yes, sometimes even without sponsoring. Organizers always need more speakers, and often more diverse panels.
Want better odds? Don’t just pitch yourself — pitch a whole panel. Propose the topic, line up two or three panelists from your network or customer base, and bring the organizer a finished package. That makes their job easier, and you become the moderator by default. Shoot your shot. 🎯
One talk becomes a LinkedIn post, a blog, a clip, and a reason to reach out to every attendee. The same is true with podcasts, here’s my PR playbook for podcasts and earned media.
Ask your customers and partners which events are worth it
Before you make your final picks, run your list past the people who know your buyers best: your customers and partners.
Send them the list of conferences you’re considering and ask:
Have you been to any of these?
Any feedback on the audience, the content, or the format?
Which ones do you think are actually high value — and which would you skip?
Are there any events missing from this list?
This one-to-one diligence with your network is gold. Your customers are your ICP, so their take on where their peers actually show up beats any sponsorship deck. Partners often know which events are packed with decision-makers and which are mostly vendors selling to vendors.
And it’s a win win: it’s a genuinely useful reason to touch base without sending another “just following up” email. People love being asked for their opinion. You’ll often find out who else is going (hello, built-in meetings and dinner guests), and you strengthen the relationship in the process. It’s another GTM multivitamin.
Should you sponsor? Skip the booth, buy the stage
If you’re seed-stage, the answer to conference sponsorship is almost always no. Series A+, maybe — and it depends entirely on what you’re paying for.
Candidly — if you’re paying just for a booth, I’d skip it in most cases. A booth puts you in a sea of other booths, waiting for foot traffic and scanning badges from people who wanted the free socks. That’s where trade show ROI goes to die.
But if you’re paying to get on stage, host a roundtable, or host a dinner, those are opportunities I’d consider — as long as they clear the 5x threshold.
The difference? A booth makes you wait to be found. A stage, a roundtable, or a dinner puts you in front of a curated audience as the expert in the room. It brings people to you.
Whichever you choose, the same 5x rule applies — but now you’ve got your day rate PLUS the sponsorship cost to multiply. Be damn sure you can hit it before you spend the time and money.
And if you’ve never been to the event, attend once before you sponsor. Scope out the quality of the room first.
How to research a sponsorship before you buy
Email the event producer something like this:
“Hi [Name] - I’m considering sponsoring this event and need a bit more information to build a business case. Can you share:
Who normally attends (titles), and the size or profile of their companies? Could you share last year’s attendee list for illustrative purposes?
What sponsorship packages are available, and what does each include?
Are there speaking, roundtable, or hosted dinner opportunities?”
Almost always in my experience…they’ll send you last year’s attendee list.
That list usually includes only company names and titles (not names, for GDPR and privacy reasons). But you can enrich it using Apollo or Clay, and boom. You’ve confirmed whether it’s the right audience AND built a target list of people to reach out to before the event.
Host your own dinner or happy hour (no sponsorship required)
Even better than paying the organizer for a dinner slot? Hosting your own. This is the play I’ve seen work again and again for the startups I work with: skip the booth and host an intimate dinner or happy hour around the conference.
You don’t need the organizer’s permission or a sponsorship package. The conference already did the hard part — it flew your ICP into one city for a few days. All you have to do is invite them somewhere better than the expo hall.
Let’s do the math:
Booth: ~$20,000+ for a few days of standing on a carpet square, hoping the right person wanders by.
Dinner: ~$2,500 for 10 hand-picked buyers, customers, and partners around one table for two to three hours.
That’s an eighth of the cost (or less) — and I’d bet on the dinner every single time. That intimate, face-to-face time goes so much further in your sales process. Nobody remembers the 40th booth they walked past. Everyone remembers the founder who hosted a great dinner and actually listened.
How to make it work
Keep it small. 8–15 people is the sweet spot. Big enough for good energy, small enough for real conversation.
Curate the guest list. Mix prospects with a few happy customers and friendly partners. Your customers do the selling for you (and it’s far more credible coming from them).
Invite early. Send invites 3–4 weeks out, right alongside your meeting outreach. Over-invite — some people will drop.
Pick a venue with a private room or a quiet corner. You want people talking to each other, not shouting over a DJ.
Don’t pitch. Host. Make introductions, ask good questions, and let the business conversations happen naturally.
Follow up within 48 hours. A personal note referencing something you talked about, then book the next meeting.
Can’t swing a dinner? A happy hour works too — possibly lower cost, a looser vibe, and easy to co-host with a partner who shares your ICP and splits the bill. Win win.
For more on running intimate events, check out my IRL events playbook and these ABM plays that work with zero ad spend.
Say you’re going before you decide to go
Here’s a move most founders don’t think of: you can announce that you’re attending a conference before you’ve committed to going.
Tell people you’ll be there — in your marketing, on LinkedIn, in your outreach to prospects and customers. Then try to book meetings around the event.
If you book enough meetings, you go. You’ve just pre-loaded your ROI before buying a plane ticket.
If you don’t, you don’t go. Plans change. Let the people who did book know something came up, and offer to meet virtually instead — those are still warm conversations, and you’ve lost nothing but a few emails.
The rule of thumb: don’t get on the plane unless you have at least one of these three things locked in —
A speaking opportunity
A curated, intimate event (your dinner, roundtable, or happy hour)
Enough booked meetings to clear your 5x bar
No stage, no room, no meetings? Stay home and spend those three days on your warmest sources of pipeline instead.
Want help booking the meetings?
Booking meetings before a show is real work: building the attendee list, finding the people who actually fit your ICP, writing outreach that doesn’t sound like everyone else’s, and chasing replies onto calendars. It’s also the work that gets skipped when your team is busy.
That’s exactly what my friend Dan does at Turnout. His team finds the right attendees, runs personalized outreach, qualifies the replies, and puts meetings on your reps’ calendars before the show even opens — so you land with a full calendar instead of a cold list. They can also help you host intimate dinners and side events around the show. They recommend starting 4–6 weeks out.
If you’ve got a conference on the calendar, connect with Dan and tell him I sent you. 🙏
Should you attend as the founder? Run the 5x event ROI rule
Your time as a founder is your highest-value asset. Full stop.
You have limited time and limited money to 1) survive and 2) grow. Make decisions about where you spend both accordingly.
Ask yourself these questions before you commit to any conference:
Is the primary audience your ICP AND your buyer persona? Will your actual decision-makers be in the room? (If you’re fuzzy here, start with how to properly define your ICP.)
Can you deepen relationships with existing customers there?
Is there a speaking opportunity?
Can you host (or co-host) an intimate dinner, roundtable, or happy hour around the event?
Add it all up: can you realistically generate a 5x ROI from attending?
Say your “day rate” for being out of the office is $5k, and the conference is 3 days. Can you reasonably expect to generate $75k in closed-won deals ($15k × 5)?
Or, can you expect to generate 5x your ACV in net new pipeline?
Don’t waste your time if you can’t answer yes to at least questions 1 and 5.
And here’s the reality: questions 2–4 are usually what get you to question 5. That’s why the 5x question comes last. Walking the floor alone rarely hits 5x. A stage, a curated room, or a calendar full of booked meetings is what does. That’s exactly what everything above is designed to get you.
Should your sales team attend?
If your sales reps want to go to a conference, make them run the same exercise.
They should submit a business case detailing how they’ll generate a 5x ROI — which events, which accounts, which meetings.
One founder I know requires his reps to book at least 20 meetings before he approves the travel expense. Brilliant. Make them earn it. (And if they need help getting there, see Dan above. 😉)
Final pro tip: you don’t always need a ticket
I know plenty of founders who fly into the conference city without buying a ticket and post up in the hotel lobby or a nearby coffee shop to take meetings.
Sometimes you don’t need to be in the room to capture the ROI — just in the vicinity. 💡
Where to start
Here’s your homework for this week:
Let AI do the legwork. Use an AI tool with web search (Claude, ChatGPT, or Perplexity) to build your long list and fill in the details for you. Ask it for: every conference your ICP attends next year; dates, city, and ticket cost; typical attendee titles and company sizes; who spoke last year (so you can see what kinds of speakers and topics get picked); call-for-speakers deadlines; and sponsorship options. Try a prompt like: “Find the top 20 conferences my buyers attend in 2027. For each one, list the dates, city, ticket price, typical attendee titles, last year’s speakers and session topics, whether there’s an open call for speakers and its deadline, and what sponsorship options exist.” Drop the results into a spreadsheet.
Calendar or track the deadlines. Put every call-for-speakers deadline on your calendar so none slip by.
Gut-check with your network. Send the list to three customers or partners and ask which ones are worth it.
Run the 5x rule. For every event that survives, do the math before you book anything.
That’s it to start. You’ll make far better decisions with the full picture in front of you.
Once you’ve picked your events, the companion articles from 2024 walk you through the rest: how to prepare for a conference to win, what to do IRL at the conference, and what to do after the conference.
See ya next week!
With love and gratitude -
If you want to learn more about working with me directly…
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