Planning Events That Inspire Attendee Connections

I spent $25K on a dinner last Tuesday. The $10 name tags generated more ROI than any marketing campaign we’ve ever run. We gave out metal name tags. Custom-engraved. Nothing fancy. I almost died of anxiety getting them shipped in time. But by Thursday, people were still wearing them around San Mateo. At totally different SaaStr events. That’s when I knew this wasn’t just another founder dinner. It was something people wanted to be identified with. No RSVP forms. No sales pitch. Just 90 hand-picked founders and product leaders packed into a single restaurant. And here’s what happened organically: - Small-group conversations spilled outside the restaurant until 10pm - A founder told me they solved a product problem during a chat at the bar - Two partnerships were formed between attendees who’d never met before Here’s what we learned about building genuine connections in an industry drowning in “networking events”: 1/ Create a momentary escape We rented out the entire restaurant. No outsiders. No agenda. Just a space for authentic conversation. 2/ Curate ruthlessly We personally invited those who would make the evening better for everyone in the room. 3/ Design for post-event connection Those engraved name tags became conversation starters days later. “Hey, weren’t you at the Recall.ai dinner?” Traditional marketing tracks every dollar. But building genuine community means letting go of immediate attribution. Three different attendees DM’d asked, “When’s the next one?” That’s the kind of community equity you can’t measure on a dashboard. What’s the most meaningful connection you’ve made at an event that wasn’t trying to sell you something?

MEMBERS ONLY: a new interview series by me, exploring the minds behind the world’s most sought-after experiences. My friend Molly Bridges is making the case for a role most events completely overlook: A dedicated host. As a master of experience design and the Senior Director of Events & Experiences at Bilt Rewards, Molly is behind some of the best events in NYC and SF. But it’s not just good taste, it’s strategy. She engineers these gatherings with a mix of psychology, hospitality, and her background in education, making sure every detail is designed for connection. We got deep into the nuances of event design and how Molly applies Maslow’s Hierarchy of Needs to design experiences that actually make people feel something. At the core of Molly’s approach is a simple truth: Adults are a lot like kids. We crave routine, structure, and clear expectations, and if those things aren’t in place, no amount of fancy decor will save your event. The Five Needs to Address for a Well-Designed Event 1️⃣ Physiological Needs (The Basics) If your guests are texting you day of asking what to wear or where to go, you've already lost them. Great events start before they even show up, with clear, actually helpful communication. Tell them what to wear, where to go, when to arrive, and make it easy. Email marketing isn’t just for hype; it’s there to eliminate confusion. If people are second-guessing the details, the event is already off to a bad start. 2️⃣ Safety (Feeling Comfortable & Welcome) First impressions set the tone. Signage should be obvious, ppl should never feel lost in the space physically and they should feel connected emotionally. That means a host that knows their name, greets them at the enterance. Take a page from Anna Wintour, who has an assistant at every event whispering key guest intel in her ear. A great host isn’t just friendly, they’re prepared. Know people's names, greet them like they matter, and watch how the energy of the entire event shifts. 3️⃣ Love & Belonging (Fostering Connection & Community) Smart seating makes or breaks a room(see my Members Only on Jake Sacks). Structured intros cut the awkwardness, and intentional space design, cozy nooks, group seating, natural gathering spots, does the rest. No forced networking, just effortless conversation. 4️⃣ Esteem Needs (Ensuring People Feel Seen & Valued) An event should exceed expectations. Deliver what you promised…Did guests meet someone interesting? Did they gain what they came for and more? Whether it’s networking, learning, or community-building, the experience should feel intentional and worth their time. 5️⃣ Self-Actualization (Scaling Magic While Keeping It Personal) Anyone can pull off one great event. The real challenge? Scaling experiences without losing intimacy. A strong brand identity and structured playbook ensure that every gathering feels personal, even at scale. 🔹 🔹 🔹 If you’re not already following Molly Bridges, you should be.

See One. Do One. Teach One. I was watching Grey’s Anatomy (don't judge) when a line jumped out at me: “See one. Do one. Teach one.” It was Dr. Webber's mantra for medical training: observe a skill, try it yourself, then pass it on. It's also the perfect blueprint for event engagement. Most events get stuck at “see one.” Attendees listen to keynotes, sit through panels, watch demos. They see a lot, but if that’s where it ends, the knowledge fades almost instantly. The next level is “do one.” Give attendees space to try what they’ve learned, through hands-on workshops, scenario labs, role plays, or even a 10-minute exercise in the room. This helps the ideas move from theory into muscle memory. But then there's “teach one.” Create moments for attendees to share their perspective. Whether it’s a micro-discussion at their table, a peer-to-peer breakout, or a post-session “lightning share” where they explain what they learned to someone else. When people teach, they anchor the learning in their own words, and engagement skyrockets. What if designing events around this mantra could transform attendees into contributors? They stop being passive listeners and start being co-creators of the experience. Maybe that's what engagement is meant to be, after all. 

🚀 After my post yesterday, the leadership of VRMA reached out—and I’m excited to share what’s next! 🚀 In my previous post, I pointed out how VRMA, while being an essential event for our industry, didn’t fully help foster the level of collaboration and conversation needed to drive us forward as a community. It’s fantastic to see that the leadership of VRMA is listening and is eager to make improvements. Here are a few suggestions I believe could enhance the event and encourage more meaningful connections: • Booth positioning: To create better engagement and visibility, I suggest booths be placed along the edges of the hall, next to the surrounding walls, with another row of booths and one row facing the stage. Between the booths and the stage, there would be tables all around, allowing for natural interactions and conversations throughout the event. This setup ensures that most attendees are in the same hall at the same time, fostering more engagement and visibility for sponsors and exhibitors, with the entire convention happening in one hall, except for small educational sessions. • Round tables with rotating attendees: Assigning numbers to each attendee and rotating tables twice a day to encourage new connections and engagement. This setup would help foster collaboration and ensure everyone meets a wider variety of industry peers. • Logistical improvements: Simplifying equipment handling, especially when it comes to moving in and setting up booths without unnecessary restrictions. • Better connection opportunities: Reducing the division created by badge colors or property counts and instead fostering more organic conversations across the board. Ultimately, I believe the value VRMA should aim for is to foster collaboration, conversation, industry knowledge, and inspiration. In this post, I’ve focused specifically on collaboration and conversation, as these are crucial for creating a more connected and stronger community. By making these adjustments, we can ensure that every attendee has the opportunity to engage, share insights, and build lasting relationships, which will help drive the industry forward. Now, I’d love to hear from you! If you’ve attended the event, what frustrations or suggestions do you have for improvements? Let’s come together as a community and share our insights so we can make the next event even better for everyone involved. 💬 Drop your thoughts and suggestions below! Together, we can create an event that not only highlights our industry but also strengthens it. 💪 #VRMA #VacationRentals #CommunityGrowth #IndustryFeedback #EventImprovements #Collaboration

𝗣𝗮𝗿𝘁𝘆 𝗣𝗹𝗮𝗻𝗻𝗲𝗿 𝗯𝘆 𝗗𝗮𝘆, 𝗩𝗖 𝗯𝘆 𝗡𝗶𝗴𝗵𝘁 Venturing in Public 5/13/25 One of the most underrated skills in venture? Event planning. I never realized how integral events would be to the profession. Over the years, I’ve hosted hundreds of gatherings—from roundtables and salons to founder dinners and even meditations. Behind the scenes, I’m grateful for a stellar Ops Team at Founder Collective who have built systems to operationalize our dozens of events each year. A few lessons I’ve learned the hard way: 𝘞𝘩𝘰’𝘴 𝘪𝘯 𝘵𝘩𝘦 𝘳𝘰𝘰𝘮 𝘮𝘢𝘵𝘵𝘦𝘳𝘴. It’s not just about getting big names—it’s about the right mix of people around the right theme. 𝘛𝘩𝘦 𝘴𝘦𝘢𝘵𝘪𝘯𝘨 𝘤𝘩𝘢𝘳𝘵 𝘮𝘢𝘵𝘵𝘦𝘳𝘴. Don’t let all the extroverts cluster on one side. Try to find commonalities for people sitting next to each other but don’t make it all one type either. 𝘖𝘱𝘦𝘯 𝘸𝘪𝘵𝘩 𝘢 𝘨𝘰𝘰𝘥 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯. It should be easy enough to answer in one sentence but interesting enough to spark a story. A great ice breaker goes a long way! 𝘈𝘤𝘰𝘶𝘴𝘵𝘪𝘤𝘴 𝘣𝘦𝘢𝘵 𝘢𝘦𝘴𝘵𝘩𝘦𝘵𝘪𝘤𝘴. As I’ve gotten older, I care more about this. I don’t want to lose my voice talking nor strain to hear my neighbor over the music. 𝘛𝘪𝘮𝘪𝘯𝘨 𝘪𝘴 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨. Earlier than you think often works - e.g. 6p dinners, even in NYC! Breakfasts are often well received. Also be mindful of school holidays, big conferences, and summer Fridays ;) 𝘍𝘰𝘰𝘥 𝘴𝘩𝘰𝘶𝘭𝘥 𝘣𝘦 𝘵𝘩𝘰𝘶𝘨𝘩𝘵𝘧𝘶𝘭 𝘣𝘶𝘵 𝘶𝘯𝘧𝘶𝘴𝘴𝘺. Always have vegetarian options. No one wants a 12-course tasting menu when they come to connect. But a crappy meal will also be remembered ;( 𝘚𝘮𝘢𝘭𝘭𝘦𝘳 𝘪𝘴 𝘰𝘧𝘵𝘦𝘯 𝘣𝘦𝘵𝘵𝘦𝘳. But big events with the right format can work too - especially if trying to make lots of connections across different sectors. When it works, something special happens: real conversations, shared vulnerability, and people later meet up for coffee or a meeting without us. That’s a real win. There’s one thing we still haven't really figured out, which is how to measure the ROI of events. We track attendance and we track sectors, but we have yet to figure out how to truly measure the impact of our events. I suppose that’s because its hard to measure the ROI of a human connection! Still, I'd love to get better ... I'm curious if others have a better system for measuring the effectiveness of their events? Also curious to hear from others: what’s the best founder/investor event you’ve ever been to—and what made it work?