This Founder's Obsessive Music Habit Spun Into Three Different Businesses Don MacKinnon's love of mixtapes helped him start multiple successful ventures.
By Don Mackinnon Edited by Frances Dodds
This story appears in the December 2021 issue of Entrepreneur. Subscribe »
I have built two companies and am now growing my third, Hark Audio. Often, people wonder how serial entrepreneurs like me continually come up with new ideas, and my answer is this: Starting a business doesn't always mean starting from scratch. If you have a powerful, foundational insight about something people love, you can make a career out of building concepts on top of it.
Dennis Crowley did something like this. His obsession with location-based social media led him to form Dodgeball, which he sold to Google, and then to cofound Foursquare. Similarly, Paul Davison and Rohan Seth were passionate about finding new and more intimate ways of connecting people, which led to multiple failed startups and then one that hit: Clubhouse.
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And me? I was the kid in high school who spent hours in my room trying to create the perfect mixtape — one that could segue seamlessly from Tom Waits to Duke Ellington to the Replacements. Eventually, I realized mixtapes are more than just about music. They are a powerful format for inviting discovery and bringing people together to amplify their excitement over a shared interest. That's when mixtapes became the driving force behind my career.
I started very literally, by launching a chain of music stores called Hear Music in 1990. It was the first in the U.S. to feature CD-based listening stations for people to explore music beyond their comfort zone. We themed each station like a mixtape — Border Radio, Paris Hip Hop. We even got our favorite artists, like the Rolling Stones and David Byrne, to curate their own collections of songs they loved. Nine years later, Starbucks acquired the company and millions of new listeners discovered our 300-plus CD compilations. Starbucks even opened coffeehouse "music bars," where you could burn your own mix CDs.
Next, I wanted to broaden the concept of a mixtape to include other cultural expressions. I cofounded Milq, a platform where users could collaborate to create "mixtapes" of their favorite movie scenes, books, sports moments, and more. Brands including the NBA, Barnes & Noble, and The New York Times used Milq to engage their audiences, and the data from all this usage allowed us to train an AI algorithm for personalized recommendations. It became so strong that we spun it out as a separate business and sold it to TD Bank.
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As I thought about what to do next, I wondered how my beloved mixtape framework could be applied to today's media needs. Listeners are overwhelmed by the vast number of podcasts, with no way to search the episodes, so this spring we launched Hark — a platform where editors create "Harklists," which are collections of great three-minute moments from a wide range of shows that explore a theme. There are Harklists on everything from Prince to NFTs and from urban design to happiness. These are mixtapes of stories, ideas, and conversations. We've built an audience of podcast lovers, and brands like Starbucks, which sponsored a Harklist series on climate change, are using Hark to connect with them in new ways.
How can you find your own core concept, from which many business ideas can grow? I recommend starting with something you love and questioning exactly why you love it so much, and whether that insight can apply to other people in other situations. After all, my original mixtapes were just on cassettes — a format that has long since expired. But the idea behind the mixtape? The reason why people loved them? That has no expiration date.
