For Kaleigh Canavan, every great business has something in common with a great video game.
Progress doesn’t come from taking the easiest path. It comes from saying yes to challenges, learning from experience, and surrounding yourself with the right people. That’s why conversations with Kaleigh often include words like XP, side quests, and leveling up. They’re gaming terms, but to her they’re just another way of talking about business.
It’s a mindset that’s shaped both her business and her nine years with LeTip of Denver Metro, CO.
Kaleigh is the co-founder of SideQuest Events, a Denver-area event company that brings together local businesses, makers, nonprofits, artists, and families through community markets and events. Walk through one of her events and you’ll see people stopping to chat with vendors, discovering businesses they’d never heard of, and making introductions that might not have happened anywhere else. Kaleigh believes small businesses deserve more than a table at an event; they deserve an opportunity to be seen. That’s why every SideQuest market follows a category-exclusive vendor model. Much like LeTip, every business has its own place, giving vendors the chance to stand out instead of competing with someone selling the exact same thing a few feet away.
Creating those opportunities is what Kaleigh enjoys most. She loves watching conversations happen between people who were strangers just a few minutes earlier, because she knows that today’s introduction could become tomorrow’s collaboration, referral partner, or lifelong customer.
That same outlook is what has kept her involved in LeTip for nearly a decade.
When asked what LeTip has given her, Kaleigh doesn’t immediately talk about referrals. Instead, Kaleigh talks about having “a rich roster” of people she can call. Business owners with different experiences, different strengths, and different ways of solving problems. That’s one of the things she values most about LeTip. Over the years, those business relationships have grown into something much bigger. “At this point, most of my best friends are people I’ve met through LeTip,” Kaleigh says. “Being a business owner can be really lonely.” Surrounded by people who understand the challenges of entrepreneurship, she found something she wasn’t necessarily looking for when she joined: lasting friendships.
Today, Kaleigh is serving her fifth term as Chapter President across four different Colorado chapters. She’s also personally sponsored 22 members into LeTip, earning her Silver Badge and moving steadily toward Gold. Ask her what she’s learned about building a great chapter, and she’ll tell you it’s less about filling categories and more about finding the right people. She jokes that her chapter chooses members “based on vibes first, then qualifications,” but behind the laugh is a belief she’s seen proven time and again: when the culture is right, everything else has a way of falling into place.
For Kaleigh, XP has never been about reaching the next level by yourself. It’s earned by saying yes to the side quests; the conversations that turn into friendships, the introductions that open unexpected doors, and the opportunities to help someone else move forward. That’s the kind of experience she’s helping create every day, both through SideQuest Events and within LeTip of Denver Metro, CO.
