Originally published in Twin Cities Business Magazine on 3/23/25.
If you’re older than 30, you likely have distinct memories of making mixtapes or burning CDs. And if you do, you remember the joy of finding a new favorite song, sharing beloved artists with friends, or—better yet—receiving a mixtape. Mixtapes were an expression of yourself and a glimpse into someone else’s world.
So how is curating the perfect playlist similar to angel investing? Let me show you.
It Starts with a Theme
Every great mixtape had a cohesive theme. Before you could start on an epic mixtape, you needed to know why you were creating it. Was this the creation of “new favorites,” a “chill mix,” “breakup ballads,” or “pump-up songs”?
This is what angel investors call their investment thesis. It sets the guardrails of what to invest in, and why. An investment thesis becomes a unique initial screening tool and blueprint for decision-making.
Finding the Needles
After identifying a theme, it’s time to start hunting for the best songs. For those born in the MP3 era, space on these mixtapes was limited. You had room for about an hour’s worth of bangers, tops.
In the world of angel investing, this is called deal sourcing: scouting out the most compelling startups to potentially invest in.
Curate The Mix
As with a portfolio of investments, each song in a mixtape needs to both stand on its own and fit the broader theme. With limited space, every song has to undergo its own version of a cost-benefit analysis. Sounds a lot like due diligence and portfolio strategy, if you ask me.
Play It Out!
At this point, you would share the mixtape with friends or family. There was a ritual of getting “social proof,” or peer validation, of the music you curated, even if you were testing the boundaries.
In angel investing, once you’ve decided to write a check, it is common to share the opportunity with others in your network who you think might be interested in the deal. We call this syndication, and it’s an important step that shouldn’t be overlooked.
Let It Stand the Test of Time
Ever find one of your old mixtapes and give it a listen? Which songs do you still know all the lyrics to? Which ones didn’t age well and maybe made you cringe a little? The reality of angel investing is your portfolio will include both timeless hits and some duds. Upon reflection, you can make whatever adjustments are needed to continue your hunt for the next star performer.
The Epilogue
So while I know this isn’t a perfect analogy, there are some parallels to help simplify the key principles of angel investing. In the end, it is a self-reflection of the things you care about and your biggest ambitions for the future.
