Why Tundra Angels Invested in Cylerity

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This is the story how Tundra Angels invested in Cylerity.

Sometimes, deal flow surprises you at the most unexpected times.

In August of 2024, I attended a Midwest Founders Community event at a yacht club in Milwaukee.

As an aside, some VCs own yachts. Other VCs have friends that own yachts. Me? I just show up at an event and pay for a Chardonnay just to be near the yachts. 😉 

On a more serious note, I’m also grateful that Angela Damiani, Amanda Daering, Nick O’Brien, and the entire Midwest Founders’ Community team put these events together!

While at the event, I met a University of Wisconsin-Madison student, Aaryush Gupta.

Aaryush was about to graduate from UW-Madison with a double major in Computer Science and Data Science, and a minor in Business. Over drinks, he described the AI-enabled projects he was working on. He shared that he had been working with a company in the healthcare space that processes Medicare, Medicaid, and commercial health insurance claims; that the CEO was a repeat founder; and that they had recently graduated from CDL (Creative Destruction Lab) Risk Stream. He said they were finishing up their institutional fundraise.

As an investor, deal flow sometimes surprises you at the most unexpected times. This was one of those moments.

I was immediately intrigued and I said, “Wait, what’s the name of that company?”

“Cylerity”

I had never heard of it. “And where are you located,” I asked.

“We are in Madison.”

The thought that a repeat startup founder with healthcare experience who had a round closing in was what I needed to learn more. I exchanged business cards with Aaryush and asked to be connected to Ryan Wheeler, Cylerity’s CEO.

How Cylerity’s Initial Email Set the Tone

The first email from Ryan was well choreographed. In his intro email accepting the intro from Aaryush, Ryan’s also sent a longer narrative that was broken down into a few headings with details underneath. It gave a brief overview of the company in bullet point form:

• Problem:

• Solution:

• Headline Numbers: (featuring product traction, customer traction, and fundraise traction with specifics from specific investors)

• Economic model:

At the end, Ryan then threw out some times that he was available to meet via Zoom.

His email had this “no frills” feeling to it and got right into the meat of the company. I liked it a lot.

As an investor, when I look at a pitch deck, or had a passing conversation with an employee in this case, my understanding of what the startup’s current state of play may have embedded assumptions. Assumptions that often times are incorrect, except the investor do not distinguish what is truth and what our minds believe to be true. The email grounded me in the facts of what the company was doing, as well as further heightened my intrigue in the company and previewed the credibility of the founder.

At it’s core, Cylerity helps healthcare providers get paid faster. Their tech platform ingests Medicare, Medicaid, and commercial health insurance claim data, verifies the accuracy of the claims, and underwrites against the claims to advance working capital to the healthcare provider cash within 36 hours. 

Ryan and I proceeded to have a number of Zoom conversations. I then invited him to pitch to the Tundra Angels group. There was strong interest at the pitch. We then ran our due diligence process, took commitments, and invested in the company. Cylerity is our 20th company that Tundra Angels has invested in to date!

Primary Reasons Why Tundra Angels Invested in Cylerity

Non-Obvious Insight: Turning Medicare, Medicaid, and commercial health insurance claims into an asset that could be precisely valued and lent against.

Exceptional founders start with the problem and work backwards. Ryan looked at the facts: