Behind the Scenes of Angel Investing

March 19, 2025

Behind the Scenes of Angel Investing

It’s a lot less glamorous than TV portrayals, but it’s meaningful work, writes Groove Capital’s Mickayla Rosard.

Let’s play a game. I’ll say a word, you say the first thing that comes to mind.

First word: “angel.”

Next word: “investor.”

OK, now what pops into your head when you hear “angel investor”?

If you’re like most people, you’re probably thinking of Shark Tank or maybe a scene straight out of Mad Men. These pop culture portrayals—albeit entertaining—don’t quite capture the reality of an angel investing. So, let me give you a peek behind the curtain of what it is like as an early-stage investor.

Drowning in Jargon: Welcome to Angel Investing

Angel investing borrows vernacular from Venture Capital, private equity, and, of course, whatever industry the startup is in. That means so much jargon—you quite literally cannot escape it. Despite your best efforts, you will find yourself googling terms along with the rest of us (circle back once you’ve grabbed that low-hanging fruit).

The Theatrics 

To be a founder, you have to be at least a little delusional. The sheer audacity required to start and scale a company demands it. Investors, in turn, want to see founders who dream big and who aren’t afraid to swing for the fences (because, let’s be honest, investor returns depend on it). Your job as an early-stage investor? Suss out the donkeys from the unicorns.

Due Diligence: AKA “Snooping With a Purpose”

Due diligence, stated more simply, is research on a company you’re considering investing in. This can take many forms: internet sleuthing; calling up former employees or customers; running a background check; digging through financial information (hockey stick, anyone?), etc.

Despite what you see on Shark Tank, most angel investors aren’t making split-second offers over dramatic music. The real work happens behind the scenes, and trust me—it’s a lot less glamorous than TV makes it seem.

The Power Struggles

The best approach to angel investing? Be fair, transparent, and surround yourself with people who share those values.However, be prepared to see some power plays like:

  • The co-founders and early team members fighting for ownership and titles like it’s an episode of Game of Thrones
  • The consultant “helping” the founder, but whose terms are predatory
  • The investor who suddenly thinks their check made them co-CEO

This is not to scare you away, but rather make sure your eyes are wide open. It’s a winning strategy to learn to stay above the fray and practice fair dealings.

So Many Coffees, Parties, and Happy Hours 

Angel investing is a relationship business. That means showing up and getting to know people—go to local pitch events to find new deals, grab coffee with founders you’ve already backed, and build relationships with other investors and those in the ecosystem. But as your network (and portfolio) grows, so do the invites. We’re talking launch parties, holiday galas, speaking engagements, meetups to “pick your brain,” and so much more.

“Hey mom, look at this” Moment 

There is an incredible amount of pride and excitement seeing one of your early-stage investments out in the wild. I love telling my friends and family the stories behind the brands, startups, and founders I’ve backed. You better believe every time out-of-state family visits, I’m serving up Nordic Waffles.

At its core, angel investing is a thrilling mix of strategy, intuition, and relationships. It’s not all Shark Tank theatrics or champagne-soaked celebrations—most of it is careful diligence, navigating personalities, and playing the long game. But for those willing to embrace the ups-and-downs, learn the lingo, and build real connections, the rewards go far beyond financial returns.