There is a special place in my heart for community events, particularly startup-related events because that’s the primary community I’d consider myself to be a part of.

Community, especially in the lonely space of entrepreneurship, is such a critical part of growth and connection. My belief is that the best way to grow is to simply get in a room with other like-minded people building cool shit as often as you can.¹

So for the past few years a few founder friends and I have been hosting community events for startup founders in Minnesota. Our most recent one was a MN Founder’s Pickleball Tournament + Happy Hour held at Minneapolis Cider Co last week:

Forty or so founders showed up to compete in a friendly single-elimination pickleball tournament. The conversation was great, connections were made, lots of laughs, and rave reviews all around. We heard the same thing 5-6 times from founders after the event: When are we doing this again?

That was really cool to hear. And tbh it’s become a bit of a trend over our last few events; for some reason, people have really loved them, we can’t seem to do enough of them, and they’ve grown relatively organically.

So I figured it would be good to sit down and dissect a bit, to codify the art & science that goes into good, attendance-worthy events, that feel like community.

I’ll also admit that hosting events is purely a passion project for me - I have no agenda, just genuinely enjoy bringing people together. So this guide will focus on how to host good events on minimal time/budget. I’d say all in I generally spend less than 2 hours total prepping and organizing an event.

And while the events I’ve hosted have generally been startup-specific, this framework should work for any type of community event — welder’s union, citizens of Faribault Minnesota, Tulane university alumni, Tetris enthusiasts, mothers against teen drinking, whatever. Just replace ‘founders’ with your community niche and follow the instructions below:

1. Define Your Community First

The single most important decision you’ll make is who your event is actually for. This seems obvious, but it’s where most community events fall apart before they event begin.

When we started our founder events in Minnesota, we made an intentional choice: these would be genuinely "by founders, for founders." This wasn't just a cute tagline – it was a strategic decision.

Why? The startup ecosystem is filed with events that claim to be for founders, but end up attracting everyone except actual founders. They become dominated by service providers (lawyers, accountants, consultants, etc.) circling like sharks looking to hand out business cards. Real founders quickly learn to avoid these because they are purely transactional.

We decided to take a different approach:

• Explicitly marketed as “Founder-only” events

• Kept messaging focused on peer-to-peer connection, not networking

• (Gently) vetted attendees during registration

Now, this doesn’t mean you need to ‘ban’ non-founders; some lawyers and investors are truly amazing community members and startup supporters. BUT by setting the expectation that this is a founder-centric space, you naturally discourage people who are just showing up to sell.

I think this same principle applies regardless of your niche - whether you’re buidling a community for woodworkers, new parents, crypto enthusiasts, idk - just get crystal clear on WHO IT’S FOR, and protect that focus. A room full of the right people is a million times more valuable than a room full of just anyone.

2. Choose the Right Type of Event

Next, the format actually matters more than you think. After several iterations, I've found that good events must have some purpose other than merely networking. TLDR; certain event styles consistently create better connections than others, here’s what works:

• Competition-based gatherings win: Activities like pickleball, cornhole, shuffleboard, or beer pong tournaments create natural mixing that happy hours just can't match

• Keep it low-pressure: Classic networking events make people anxious; games give everyone something to focus on besides awkward small talk

• Avoid pure "networking" events: When the stated purpose is just "come network," you end up with people scanning badges and handing out business cards rather than making genuine connections

• Balance competition with inclusivity: Choose activities that don't require specialized skills but still offer fun competitive elements

What's magical about game-based events is the self-selection factor. The people who show up are already demonstrating they're open to meeting others and willing to participate - exactly the kind of community members you want.

3. Pre-Event Setup (2 Hour Prep)

The secret to running the events without spending weeks of your time prepping is to establish a few systems that work for you while you sleep. Here’s how I keep my prep time per event under 2 hours total:

Build an Automated Distribution Engine (30min set-up)

• Create a simple landing page with email signup form

• Start a LinkedIn group for your community (Facebook works too)

• These two assets will become your automatic lead generators

• When planning a new event, you'll already have your audience ready

Event Planning Checklist (45min)

• Host events on weekday evenings (Tuesday-Thursday, 4-8pm works best)

• Find a venue that fits your activity (breweries and outdoor spaces are gold)

• Create a Google Form for RSVPs (don't overthink this with fancy platforms)

• Design a simple single-elimination bracket template you can reuse

• Secure simple funding (small corporate sponsor or minimal $20 ticket fee)

Promotion Strategy (45 min total)

• Announcement email (2-3 weeks before)

• 1-week reminder

• Day-before reminder

• Day-of final details

Day-Of Materials (15min Target Run)

• Name tags ($8, crucial for first-timers)

• Basic signage ($30, plan to use them every time)

• Portable microphone ($60 rental)

• Small trophy or prize ($25, makes the event feel ‘important’)

3. During the Event: The Flow Formula

The key to a great event is creating natural mixing opportunities. Here's the template I follow for event run-of-show:

• First 30-60 minutes: Check-in period, casual mingling

• Formal kickoff: Brief welcome, explain the format, set the tone (keep it under 3 minutes)

• Tournament structure: Use random pairings for the first round if people come solo - this is your secret weapon for forcing new connections

• Keep it moving: Single elimination tournaments maintain energy and prevent dragging, also still leaves plenty of room for casual happy hour convo’s

• Create moments: Award small door prizes throughout (we gave out jars of pickles for things like ‘best dressed’ and ‘best team name’ at our last event)

• Capture everything: Take tons of photos or hire a photographer (worth the investment, pro photos can make even a bad event seem awesome)

• Closing ceremony: Crown winners, thank everyone, and most importantly - announce the next event date if possible

One thing that makes our events special is how we handle solo attendees. Instead of letting them awkwardly find partners, we deliberately pair them with other founders they haven't met. This forced randomization creates connections that would never happen organically and becomes a highlight people mention after almost every event.

4. After the Event: Crucial Follow Up

The real community-building happens between events. Here's my post-event ritual:

• Same-day social posts: Upload the best photos and tag everyone while energy is high

• Thank-you email: Send within 24 hours with photo links

• Community cultivation: Use this moment to invite new attendees to join your email list and LinkedIn group

• Plant seeds for next time: Mention the approximate date of your next event to build anticipation

Why This Actually Works

What separates good community events from great ones isn't budget or production value - it's the genuine connections. The competitive tournament format creates shared experiences that bond people far more effectively than standing around with drinks.

I remember at our last pickleball tournament, two founders who had never met were randomly paired together. By the third round, they were like old friends, and by the end of the night, they'd discovered a new business idea they tried launching later in the year. That team didn't win the tournament, but they both left with something more valuable (#goalz)

The trophy and prizes add a fun element, but they're honestly just excuses to get people in the room. The real magic is in designing an environment where connections happen naturally.

The Real Secret: Consistency Trumps Perfection

Don't overthink it. A decent event that actually happens is infinitely better than the perfect event that never materializes because you got lost in the details.

Start small, create systems that make organization nearly automatic, and focus on bringing good people together around a simple activity. The community will build itself if you just create the space consistently.

And remember, the best community events aren't about you - they're about creating moments where others can connect. Focus less on impressive production and more on removing barriers to genuine interaction.

As founders, we're often so focused on scaling our businesses that we forget the importance of scaling our support systems too. Community isn't just nice to have - it's essential for the long, often lonely road of entrepreneurship.

Peace,
Ramsey

1  I owe this worldview to a few people in particular: Sean Gilfillan who taught me it as a marketing consultant while I was working on Uptrends, and Nick O’Brien who is an incredible startup community advocate - he also introduced me to the book Bowling Alone which really crystallized the community-centric worldview for me.