2019 was the hardest year of my life.
Prior to founding Tundra Angels, I was a startup founder.
Until that point, I had spent five years building a financial technology startup with my father, Jack, as my Co-Founder. We built out a software product for the bond market. We raised venture capital from FIS, a $10 billion company on the Fortune 500. I pitched around the country to angels and venture capital investors. I fully lived the founder side of the table.
Unfortunately, my startup didn't pan out.
My father, who was my co-founder, got hit with cancer in late 2018.
This was actually my father’s third cancer diagnosis, having previously been diagnosed with cancer in 2009 and then a second time in 2014.
He didn’t recover from his third round of cancer.
✅ I found myself losing my father and a company at the same time. ✅
My family and I lost him six months later in June 2019.
(If you have gone through a family loss like this, you can resonate that there is so much wrapped up in experience just by itself. I will share more in the future, but it has certainly taken years to unravel from this.)
But… a light emerged, which opened up my next professional step.
Me, my son, and my father, about a month before he passed.
Where Tundra Angels Started
✅ Although my personal life was falling apart, my next professional steps were coming together. ✅
It started with a phone call.
I got connected to the Greater Green Bay Chamber in April 2019, two months before my father passed away.
Through the Chamber’s their Economic Development Strategic Plan, they were looking to build out a pre-seed capital source for Northeast Wisconsin. I took the initial meeting in and met Kelly Armstrong, the VP of Economic Development at the time. That's the conversation that started my next chapter.
They decided that I was the person to build out this pre-seed capital source - five years of pitching investors, a venture round closed with FIS, the kind of scars you only get from the founder seat.
The Chamber initially imagined that I would raise a venture fund. From my founder experience, I knew that Northeast Wisconsin certainly needed capital infrastructure, but I was not convinced that Northeast Wisconsin needed a fund.
TitletownTech, a VC firm with a $25M fund anchored by the Packers and Microsoft, had just come online that same year in 2019. Also, there were various other angel investor networks and VC firms around the state.
✅ I noticed that Northeast Wisconsin was missing a context for individual wealth capital to connect directly with high growth startup deals.
Not via a fund, but direct access such that investors have the control to make their own individual decisions. ✅
Back in 2019, there was no collective infrastructure in Northeast Wisconsin for individual investors to write checks into VC-level deals directly.
That's what Tundra Angels is.
Three Paths to Investing in Startups
There are three major contexts to invest in high growth startups:
A direct connection to invest individually. This is where the investor happens to know a few founders in their own personal networks. They write checks based on personal relationships. Historically, it is the way most people in this region have lost money in this category. (More on that in a future issue.)
A venture fund. This is where the investor commits a chunk of capital, typically $250K-$500K over three to five years. The fund manager, not you, decides which companies get your money. You are a passive LP. This is a great option if you trust the manager's thesis and want a hands-off "set it and forget it" allocation to the asset class. That is how arguably the majority of investors get exposure to venture capital deals.
An angel investor network. (That's us - Tundra Angels). You pay an annual membership fee of $3,000 annually to get access. I as the Manager act as the gatekeeper and heavily vet startups on the front end, only selecting those who are legit to pitch for the group. The fundamental experience is the quarterly pitch meeting where investors see the startup pitches directly, meet the founders, and discuss with other investors who are experts in different industries (see picture below). When it comes time to invest, you decide deal by deal whether to participate, and at what check size. The members have the control. Not a manager.
Peeking behind the curtain of a Tundra Angels pitch meeting
The difference between option 2 and option 3 is who's making the decisions.
In a fund, the fund manager picks. In a network, you do.
That's the structural shift of a venture fund vs. an angel investor network. For a business owner that is used to running their own P&L and making their own calls, it tends to be in line with how they already run their lives and their businesses.
The return potential in an angel investor network tends to be greater, as you will see in a future article.
It also tends to be WAY more fun, in our opinion.
Six Members to Fifty-Five
We started July 2020 with six members. Six became twelve. Twelve became eighteen. Now we're at around 55 members and continue to grow.
We’ve invested in 24 startups, soon to be 25. About $6 million deployed. Being transparent here, we've had four shut downs, which is part of the nature of the space.
However, the valuation markups many of other portfolio companies are very attractive.
In 2025, our portfolio companies raised over $71 million in venture capital last year.
What Tundra Is Now
Tundra Angels became independent from the Chamber in mid-2022. The Chamber seeded Tundra and then Tundra graduated. The model proved demand was real in that enough investors in Northeast Wisconsin wanted to participate in this asset class that the network could stand on its own.
Somebody recently asked me what Tundra is, and I gave a longer answer than I usually do. We're a few things at once:
An investment company. ~160 startups across my desk per year. ~15 pitch the group. ~5 we invest in. Highly curated, Wisconsin-only deal flow.
A social network. 55 business owners and executives who hadn't necessarily known each other before, who now see the same deal flow, conversations, and importantly, the expertise in the network helps de-risk our investment decisions.
A media company. This part I'm still growing into. For startup founders, those who Tundra Angels looks to fund, I also write a weekly newsletter wiht insider tactics as an investor that I wish I would have known 10 years ago as a founder. Each time we invest in a startup, I write a "Why We invested" email. This goes out to over 8,000 founders and VC investors. Sometimes those emails get investment into our companies as well. I sent one about a "Why Tundra Angels Invested in Cylerity," one of our portfolio companies. A fund manager in the Twin Cities read it, took a meeting with the founder a month later, and joined the round with a $750,000 check. That happened because of one email!
An educational company. Honestly, this is the thing I most want to grow into. Investor education is the gap. This newsletter is one piece of closing it.
If you've built a business in Wisconsin and you're sitting on capital you'd like to deploy beyond real estate or the public markets - curious about venture but not sure how to enter - then this newsletter is for you. Or if you've thought about angel investing before and walked away because the deal didn't make sense or you didn't know where to start, I am also writing to you.
Most of what's published about venture capital has a lens of Silicon Valley. But, it doesn't connect to here, that is, greater Green Bay and broader Wisconsin. The dynamics in the state are different from the dynamics there, and the opportunities require translation. That's the work I want to do.
If you want Wisconsin near the top of where innovation happens, I want you in the room with us. This newsletter is the first step toward that conversation.
Closing Thoughts
I wouldn’t have chosen my father’s decline and death as the catalyst for me to eventually have the opportunity to found Tundra Angels.
But failure, pain, and passing through the fire is a teacher unlike any other.
And, in a strange but real way, without that part of my story, individual investors in Northeast Wisconsin and around the state wouldn’t have the access and context to invest in world changing Wisconsin startups, be part of an incredible local network, and catalyze real change from a personal financial standpoint as well as a broader societal standpoint.
When I was losing my father and a company at the same time in 2019, I didn’t realize what I, our investors, and Northeast Wisconsin would later gain - an exclusive room of angel investors where the future is built.
See you next Wednesday.
-Matthew Kee