Angel Investing: who is on the sidelines that ought to be in the game?

I started working at gener8tor just over 4 years ago. In the time since, we’ve worked with nearly 1,500 startups. It’s a lot of dealflow, but I make an effort to read most of the monthly updates that come through my inbox (founders, we really do read these!)

Separate but related, every few weeks I check in with a good friend of mine working in venture and startups. We discuss interesting patterns we’re seeing, ideas for collaboration, the Packers, usual talking points. About a month ago on one of these check-ins, he says: “We’re going to pull together an angel syndicate for one of those companies you sent. Know any angel investors that would want to get involved?”

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Oh man, I love it when a plan comes together.

But then I paused, I guess I don’t know many angels?

None that are already angels at least. There are plenty of angels and groups active in the Milwaukee area, or elsewhere across Wisconsin, or clustered around other states or alma mater. Sure I could (and probably should) get more involved in these groups for the future, but this startup is raising now, opportunity is knocking and I’m a huge believer in the team, their product and growth.

Then the question became: who should get involved?

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While there is a lack of venture capital investment in places like Wisconsin, there’s no lack of smart people. These smart people work in real estate, traditional finance, logistics, healthcare and the other bedrock industries in the midwest. You wouldn’t associate them with being angel investors, but at the same time has anyone really asked?

So what the hell, let's give it a shot. Reached out to a short list of contacts that checked both boxes of being accredited and having argued together about go-to-market strategies on Shark Tank. I shared details with 9 friends, and while most passed on the specific syndicate that started this journey I noticed an interesting pattern across the group.

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Everyone wanted to see more. And these folks were way more familiar with startups than I had previously thought. No’s were thoughtful and well-researched, yesses were measured with detailed questions on the product and customer success strategies. I had to clear up terminology here and there, but I was impressed by the openness and understanding of the bet (and odds) in front of them.

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These weren’t Patagonia wearing finance bro types, they were some normal young professionals peppered around the Rust Belt working in the industries we take for granted. They were thrilled that someone was trying to get them off the sideline and open the door into the world of startups.

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This experience was specific to the situation. 

A syndicate I’ve known for years, a startup I’ve followed for just as long. It was as good of a starting point as could be. But the point remains – who is on the sidelines that ought to be in the game?

‍Jake Westreich is Director of Partnerships at gener8tor, a venture firm and accelerator with operations across the Midwest and beyond, including multiple global programs. Based in Milwaukee, he has been an entrepreneur and small business owner as well as working for EatStreet, one of Wisconsin’s most successful startups.

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