What happens when you mix music, creativity, and a dash of ambition? For Drew Leahy, it launched a journey straight through Ann Arbor’s creative core, across Silicon Beach, and back again. Today, Leahy empowers the next gen of Wolverines in ENTR 414: Startup Sales at the University of Michigan’s Center for Entrepreneurship (CFE).
Origin Story
Drew’s entrepreneurial spark started right here at U-M. Not in the business school, but as a musician ready to make waves.
“I was obsessed with the intersection of creativity and capital, which led to my first ‘Aha!’ moment: MyBandStock. We built a platform that allowed fans to ‘invest’ in their favorite bands—a concept that felt radical in 2007.”
This bold experiment changed Drew’s path and led to recognition.
“That experience, which earned me the 2010 Ross School of Business Entrepreneur of the Year award, hooked me on the thrill of building something from nothing.”
Startup Grind & Global Growth
After college, Drew dove deep into startup life. “From there, I moved to Los Angeles to cut my teeth in the ‘Silicon Beach’ ecosystem. That was my era of ‘The Grind,’ operating at multiple high-value creator startups.”
In 2014, Drew co-founded SnapSuits, a high-tech menswear e-retailer, with his brother.
“We bootstrapped our way to millions in revenue and an 800% ROI on ad spend. We learned the hard lessons of e-commerce, logistics, and scaling a global team.” That real-world experience was Drew’s next launchpad: “That operator experience naturally transitioned into venture capital. I joined Hawke Media to co-found Hawke Ventures, where we raised over $30M across two funds to back the next generation of MarTech and AdTech founders.”
His journey even spanned the globe. “Recently, my journey took me to the other side of the world—New Zealand—where I served as a General Partner at Hillfarrance Venture Capital. But ultimately, all roads led back to Michigan.”
Back to Ann Arbor
Today, Drew’s mission has expanded. “I’m back in Ann Arbor with a full-circle mission: I’m an active operator (Head of Sales at Klear), an investor, and most importantly, a Lecturer at the CFE. I’m using my ‘A-Z’ experience—from dorm-room founder to VC—to help U-M students navigate the same path I took.”
His connection to CFE runs deep. “I was first introduced to the CFE during undergrad in 2008. I have kept up with the staff and donors over the years since graduation. I got a pro tip about this class being available to teach: ENTR 414: Startup Sales. I jumped at the chance. Given that ‘startup sales’ is something I have done my entire entrepreneurial career, I was over the moon to get a chance to teach students the art of sales.”
Energized by Student Impact
Drew’s love for innovation and entrepreneurship aside, there’s one other thing that keeps him going.
“More than anything, I love the enthusiastic energy that students bring to the classroom and their ideas. I had instructors and mentors at the University of Michigan who changed the entire trajectory of my career. Knowing that now it’s my turn to make a difference, to help their goals, is a huge honor.”
Advice for Aspiring Entrepreneurs
Drew keeps it real for new builders and dreamers: “Ideas are cheap, execution is gold. Do it, start it, dream it. Get others involved. Ask for help—the CFE is a great resource for guidance, or introductions to UM Alumni in your field.”
Beyond the Startup
Drew’s fuel comes from creative and outdoor adventures. “Playing music, snowboarding & skiing in the mountains, summers on the Lake, and gardening” are his favorite ways to unwind and enjoy life.
Ready to Start Your Own Journey?
Drew’s story proves that entrepreneurial mindsets grow at Michigan, from every discipline, background, and creative interest. Want to try your hand at building, launching, or leading? Join a CFE course, get advising, or show up for EHour. And if sales, startup life, or music inspires you, Drew Leahy’s class is the perfect entry point.
Ready to level up? Explore CFE’s programs, connect with student stories, and launch your next big idea at cfe.umich.edu.