By Vanessa McCrann & Margaret Hedderman
Events are a big part of Startup Colorado’s work, from our monthly Lean Coffee networking series to in-person extravaganzas like West Slope Startup Week. All our events are designed with a clear goal: to connect entrepreneurs with the resources and people they need to grow their businesses.
When done well, events are powerful tools for building strong startup communities. Our Community Director, Vanessa McCrann, leads the charge, bringing events like the Startup Colorado Roadtrip to life. As she gears up for another busy year, we grabbed some time on her calendar to learn her top tips for planning effective community events.
Thinking about hosting a startup event in your town? Read on for Vanessa’s best advice and learn how to do it the “Startup Colorado Way.”
Margaret Hedderman: How can community organizers utilize networking events to drive startup ecosystem development?
Vanessa McCrann: Rural Colorado has a robust support system for entrepreneurs. At any given time, there are dozens—if not hundreds—of events and programs designed to help entrepreneurs and small business owners succeed. It’s remarkable. The challenge, however, is ensuring these resources reach the people who need them most. Entrepreneurs are busy launching businesses—and sometimes working a “real job” while they do it—so how can we make our programming worth their while? How do we make sure they know about—and see the value in—showing up?
The answer: networking events!
People attend networking events if they look exciting, relevant, and a good use of time. A well-organized event brings together the right mix of stakeholders—founders, funders, mentors, service providers, and business support organizations. When balanced correctly, these gatherings foster collaboration, surface challenges, and lead to real solutions.
MH: Before you start planning an event, why is it important to first determine the purpose and desired outcomes of your networking session?
VM: A good event serves the audience, not the organizer. The first rule is to ensure your event is worth your audience’s time (and money!). To do that, start by defining the event’s purpose—what should attendees gain? Is it new peer connections, a cost-saving legal strategy, hands-on experience with an AI tool, or training to apply for funding?
Once the purpose is clear, weave it into every aspect of planning—from pre-event communications to seating arrangements to your closing notes. When your goal is baked in from the get-go, it naturally shapes the entire experience, making everything more valuable and impactful for attendees.
For example, at West Slope Startup Week in Durango, our goal is to help founders connect, expand their networks, and access the resources they need to start and grow their businesses. Although the event isn’t until October, we’re embedding this purpose into every stage of planning.
Since last December, I’ve been hosting monthly meetups for our volunteers in Durango—events like a Christmas cookie contest, a book swap, and intention-setting sessions. These gatherings build relationships and create a strong sense of community early on, ensuring that the energy and connections carry through to the main event.
MH: How do you ensure attendees—even introverts!— make meaningful connections at your networking event?
VM: Yay for introverts! I can answer this in three words: lightly structured networking. Emphasis on both “lightly” and “structured.”
It’s a Goldilocks situation—too much structure feels forced and no one’s having any fun, but just enough helps strangers start meaningful conversations. The right balance encourages strangers to talk and that’s the sweet spot!
At the end of the day, some structure is essential. I can’t tell you how many people complain about open-ended networking events—like happy hours with nothing but a charcuterie board and no real programming. People dreaded these unhappy hours before the pandemic, now they flat out avoid them. A little structure makes networking far more inviting and enjoyable.
MH: How do you choose the best event structure for your desired outcomes?
VM: Choosing the right event structure depends on several key factors:
- Desired Outcomes – What do you want attendees to walk away with?
- Organizer Bandwidth – How much capacity do you (or your team) have to plan and execute? (In my case, I’m often working solo.)
- Venue or Platform Limitations – What constraints does the space (physical or virtual) impose?
The goal is maximum impact with minimal effort—ensuring the event is both effective and sustainable if it gains popularity.
For my monthly Rural Women in Entrepreneurship (RWE) virtual meetups, I want each attendee to feel supported, less isolated, and connected to a new person or resource. Ideally, I’d extend these sessions beyond an hour, but I know people won’t commit to longer online events. That’s a constraint. Likewise, there are limitations to connection-building in a Zoom format, so I make the most of our time with founder spotlights, mini workshops, and breakout rooms.
Follow-up could be another challenge. I could easily spend a week facilitating individual connections after each event, but with other projects on my plate, that’s not feasible. Instead, I compile key takeaways and shared resources into a follow-up email, trusting attendees to engage when they’re ready. The proof that it’s working? Women tell me when they’ve made valuable connections—and they bring new friends to future sessions. That’s how I know the structure is effective.
MH: Startup Colorado offers both in-person and online networking events. How do you structure these two different formats to facilitate meaningful connections?
It’s funny how different online and in-person networking events can feel. Online events allow you to achieve more with your programming due to a captive audience, but in-person gatherings tend to foster more open, authentic conversations. My first two years in this role were during the pandemic, so most of my networking events were online. Now, it’s closer to 50/50, which feels like the best balance. Here is an example of each format:
Online: Lean Coffee is a flexible, discussion-based format where anyone can contribute, ask questions, or share insights. Each month we feature a different co-host with a new story or resource to share. This works great as my monthly networking event format, as it accommodates the natural ebb and flow of attendance.
For larger turnouts, I use breakout rooms to encourage more spontaneous, authentic connections. And to make the space welcoming for everyone, I also offer a low-pressure option—if you’re an introvert or just juggling a lot, you can DM me, and I won’t call on you during open discussions. This way, both extroverts and introverts can engage in a way that feels comfortable.
In-Person: Networking Bingo has been a recent hit for in-person networking. The structure is familiar—everyone knows bingo and everyone loves prizes. But instead of just filling in squares, the bingo cards are designed to serve as conversation starters and follow-up tools.
Each participant collects signatures on their card, and when they take it home, they have up to 16 new connections along with built-in talking points for future outreach. This structure makes networking less intimidating, especially for introverts, because the card acts as a natural icebreaker. Plus, the energy in the room is fantastic—it’s always fun to hear someone yell, “Bingo!”
MH: Every event manager has at least one horror story. What’s one lesson you learned the hard way?
I’ve learned plenty of small lessons along the way, but my biggest horror story was in June 2023. It looked like West Slope Startup Week (WSSW) in Durango might not happen. The event was only two months away and we’d already experienced two lead organizers picking it up and dropping it. Time was running out. In the final hour, I was asked to step in and make it happen. At that point, there was no agenda, only 27 speaker submissions, and no real plan.
Somehow, we pulled it off—WSSW23 ended up with 81 sessions and 350 attendees.
The biggest lesson I learned? Large events have hard deadlines you can’t get around. I worked every night and weekend for eight weeks, losing my entire summer to a computer screen and nonstop phone calls (gratefully, from helpful people). When I wasn’t glued to my desk, I was running around town, personally asking founders to attend.
The stress took a toll—I had two panic attacks, and it affected my husband too. Honestly, I’m glad I didn’t have a dog yet; it would have been stressful for him as well. I’m happy to report, I’ve never experienced that level of stress at WSSW—or any other event—since then.
Now, I plan far ahead, and the more lead time I give myself, the better I feel. In the past, I’ve said yes too quickly. I’m learning to ask myself:
- Do I have time for this?
- Could we extend the timeline to plan it properly and get it on everyone’s radar?
WSSW23 was worth it in the end, but I’ll never attempt a large event on that short of a timeline again. Any event expecting more than 150 people should have at least a full year to be planned and anticipated. (Feel free to quote me on that!)
In addition to West Slope Startup Week, Vanessa is currently leading the Startup Colorado Roadtrip. This statewide event series brings essential funding resources and education to founders in rural communities. Learn more and sign up here.
Join us in empowering rural entrepreneurs and ecosystem builders to achieve even more in 2025. Contributions of any amount directly power our mission to build a sustainable statewide network of resources supporting rural entrepreneurs, so that people and places can thrive and chart their own futures! Will you help us?
