The Innovation Challenge provides students with a unique opportunity to collaborate with local businesses or non-profits, addressing real-world issues and presenting innovative solutions. This year, the challenges are focused on SidelineSwap, an online marketplace for sporting equipment co-founded by Holy Cross alumnus Brendan Candon ’10. In a recent interview with Maeley Nakamura ’26, Brendan shared his journey from a political science major at a liberal arts school to becoming the CEO of SidelineSwap and how his experiences at Holy Cross shaped his entrepreneurial success.
MN: As a political science major at Holy Cross, how did your liberal arts education contribute to your entrepreneurial success?
BC: “As an entrepreneur, there’s no blueprint. You’re constantly problem-solving and learning across a broad surface area. And the learning is often self-directed. There’s no better foundation for entrepreneurship than liberal arts because you learn how to learn and you have an opportunity to study a broad range of subjects – from economics and accounting to political science and psychology.
Majoring in political science helped prepare me for an environment where the right answer is often far from obvious. I learned to think critically, consider multiple perspectives, understand multiplayer strategy, and communicate persuasively.
In both politics and business, it’s up to the leader to ask the right questions, distill the information at hand, make the best decision possible and influence their teams to pursue that plan of action. As a political science major and history minor, I had an opportunity to study these dynamics through history’s most challenging conflicts and greatest leaders, and I think that prepared me well for life as an entrepreneur.”
Long before Brendan founded SidelineSwap, he had a history of starting businesses and talks about his successes and failures along the way, and the story of how SidelineSwap started.
MN: Did you always know that you wanted to be an entrepreneur?
BC: “Kind of. I’ve been starting businesses since I was a little kid. It just always came naturally to me. First, there was the legendary Candon Lemonade Stand. In high school, I started a lacrosse stick stringing business (success!) and a surfboard company in high school (failed!). There were some other projects (not quite businesses) while I was on campus.
My dad owns a State Farm insurance agency, so we talked a lot about that in car rides and at the dinner table as I was growing up. His love for entrepreneurship had a big impact on me.
But when I graduated, I didn’t set out to start a business. I had interned at a law firm and investment bank during college, but didn’t love either so I took a job working for my dad after school. While I was working there, a friend of mine mentioned the idea for SidelineSwap and I did what was natural to me – I started building. For the past 10+ years, we’ve been building that company. Through that, I’ve realized that I love building businesses and taking ideas from 0 to 1. I don’t think I’ll ever do anything else.”
Brendan pointed to his experience as a 4-year starter and captain on the Lacrosse team as a crucial part in shaping his leadership skills and his connection with Division 1 lacrosse players played a critical role in launching SidelineSwap in the lacrosse market.
He mentioned his continued involvement with Holy Cross Lacrosse and expressed his excitement for the future of lacrosse and the Ciocca Center.
Through SidelineSwap, Brendan and his team have put nearly $600 million back in the pockets of sports families by helping them resell last season’s gear and save on next season’s gear.
BC: “We hear from customers all the time about the impact we’re having, and it’s the best part of my job. By helping more people access sports, we’re increasing access to all the benefits that come from an active life and being a part of a team.
We’re also supporting entrepreneurs with used sporting goods businesses who use SidelineSwap as their primary e-commerce platform. It’s been so cool to see some of them turn a side hustle into a full-time job. Combining my love for sports and entrepreneurship has been incredibly rewarding.”
Brendan spoke highly of the Holy Cross community, describing it as tight-knit and supportive. He emphasized the value of connections made during his time at the college, which have been instrumental in his career.
MN: How does the Holy Cross alumni network influence your life, and what sets the Holy Cross community apart?
BC: “The Holy Cross community is tight-knit and looks out for each other. I made many of my best friends on campus and connected with some of my most helpful mentors. I’ve written many cold emails with the subject line “Holy Cross Entrepreneur seeking advice” which led to warm responses and fruitful conversations. Most importantly, I’ve consistently found that the people you meet through the Holy Cross community are genuinely good people who are eager to pay it forward.”
Brendan offered advice to current students, encouraging them to enjoy their time at Holy Cross and invest in relationships with people from diverse backgrounds and interests.
MN: What advice would you offer current students in making the most of their Holy Cross experience? What on-campus organizations, events, etc. would you recommend joining or participating in?
BC: “First, enjoy it. Four years goes by fast. The sooner you realize that, the fewer regrets you’ll have.
Second, invest in relationships with people on campus who have a diverse set of interests. These connections will be the foundation of your network going forward. Many of them will go on to do incredible things, and they’ll be the first people you turn to when you need help.
Most importantly, remember that how you do anything is how you’ll do everything. Build good habits, be a positive influence on the community, and develop a personal brand you’re proud of. All of this will pay dividends later.
And of course, take advantage of all the amazing resources available at Ciocca Center!”
When asked what his favorite Memory at Holy Cross Brendan replied “I plead the fifth”.
