10 years ago, I quit my job at Walgreens to pursue, full-time, one of the crazier ideas a 23-year-old could come up with: launching a venture capital firm. Somehow, 10 years later, I’m 25 years older—with four children, four funds and 150 portfolio companies. The past decade brought bubbles, crashes, scams disguised as ‘democratization’ (ICOs, SPACs) and waves of true innovation (like AI). In some ways we’ve been incredibly successful, but at the same time I am simply grateful to be alive and still investing.
It’s a bit surreal to see us, two twenty-somethings with negligible VC experience, go from that tiny $1M Fund in 2015, to an $11M Fund II, to a $32M Fund III and now to a $36.5M Fund IV, in just 10 years. Our LPs are incredible and varied, from founders who’ve exited, to family friends, to some of the region’s largest institutions and fund-of-funds who have evaluated nearly every manager over the past 20 years. We’ve been some of the first checks into companies like Kin Insurance, Branch, Astronomer, Loop, and have had major exits like Glidera (sold to Kraken), Pactsafe (sold to Ironclad), Ryvit (sold to Trimble) and Avail (sold to Realtor.com). We’ve also built the region’s largest annual venture event—the Club M25 Summit—bringing together our portfolio and hundreds of VCs each year. More on Fund IV from John Pletz at Crain's Chicago Business.
There’s been a lot of maturing, growth and evolution along the way—the kind word for this is ‘learnings.’ Looking back at my first, naively written blog post a few months into M25’s launch, I’m struck by how far we’ve come, and a little anxious about how I’ll look back on what feels like ‘wisdom’ today.
For one, it is truly hard to know which company will be a winner, up until the cash actually hits the bank account. I remember a time when we were staring down the barrel of a significant liquidity event for one of our earlier portfolio companies—that we doubled down on with SPV dollars—only to see the acquisition fall apart and our position to get doused in insurmountable liquiditation preferences. On the other hand, we’ve passed on a down round in a flailing company that wiped us to 1/6th of our original position, only to see that company skyrocket in growth, what could have been a 30x was ‘only’ a 7x. The fundraising journey for both us and our founders is a constant rollercoaster. Landing a $5M commitment from an LP feels so great, but we’ve also had those verbals fall completely through when Docusigns are sent.
We’ve celebrated term sheets with our founders and seen VCs pull term sheets on our founders for unwarranted reasons (thankfully we have elephantine memories and don’t make that same mistake twice). We’ve learned to think independently and prioritize our own due diligence and decision-making. The herd mentality has bitten us in many places: we’ve been the last check in on a dying company our coinvestors encouraged us to participate in, we’ve relied on other, larger firms’ due diligence to invest in companies that ultimately proved fraudulent and we’ve seen ‘this year’s hot deal’ raise too much capital with little oversight and flounder thereafter (it is much better to invest in ‘next year’s hot deal’). Thankfully, on balance, our portfolios have performed well, buoyed by enough ‘right’ decisions that have given us the ability and confidence to write larger checks, own more and get more involved with the companies we are leading.
Now, in a time where there are fewer and fewer active VCs—particularly at pre-seed and seed stage—M25 is here with dry powder and a proven playbook to lead the first round and grow the next Midwest unicorn from a two-person team to Seed, Series A and beyond. There are a lot of reasons why M25 is still here and having a bigger impact than ever before:
My wife, Rebecca, actually encouraged me to quit my stable, secure job so I could launch a risky, time-consuming ‘startup’ and skip out on countless nights and weekends while she launched her own exhausting career (shepherding a young, growing family putting in 100+ hour weeks). I had incredible initial support from close family members, who were critical for early guidance, mentorship and financial support—Brent Gutwein, Doug Drury and Stuart Gutwein. My partner Mike, who left his own stable, secure job to dive headfirst into a chaotic trailblazing venture alongside me, has been the critical balancing force in countless tough conversations and decisions. Our newest partner, Abhinaya, who joined us in 2017 right out of undergrad, and probably didn’t know how much we were all figuring out this thing together, creatively brought so much to M25. One of my earliest venture mentors, Trey Hart, who encouraged me to participate in Kauffman Fellows (which was transformational and led to Mike and then Abhinaya also participating), ultimately became a critical anchor LP as our funds grew and matured. LPAC members Aaron Gillum and Daren Cotter, who have leaned in and provided much more than capital, challenged us as we grew and faced new problems and opportunities. Our other critical team members: Katie, who has helped define what VC Platform can be, not just for us, but for many firms. Arianna who keeps the trains running on time and enables us to host all the events we do for our founders. Sam, the workhorse, who has upped our reporting/IR, due diligence and data analysis capabilities in a big way. Ruth who brings a can-do attitude to everything and has professionalized our content, media, brand and events.
It feels good to have been ‘right’ when so many said this wasn’t a good thesis. In 2015, most VCs, LPs and even founders shrugged off the Midwest pitch, and frankly they were wrong. The Midwest, along with other non-Silicon Valley geographies, has continued to rapidly grow as a percentage of all U.S. venture deals. This was true both before and after COVID, an unforeseeable pandemic that mostly helped regions like the Midwest, in particular with easier access to capital and ability to attract talent (either remote or enabling those now willing to leave the Coasts). Now, in a post-bubble era, we’re massively benefiting from efficiency and lower input costs, closer access to customers and stronger focus on ‘Rule of 40’ growth (rather than inefficient ‘growth-at-all-cost’ mentality). Major fundraises and exits have proliferated across this region, not just Chicago, not even Columbus, Minneapolis or Indianapolis, but in smaller places like Lincoln, Columbia, Ann Arbor and Fargo. It’s a massive rising tide and we have the most enhanced infrastructure—team, brand, dealflow, reputation, capital, track record—to take advantage of it.
We’re truly in the middle of an incredible mix of people. Our founders often have a choice with who to work with and even more so, who to let on their board—and yet they chose us. Over the years, many of these relationships have turned into close friendships. I’ve traveled through Central Asia with two of them, met for early morning runs with others, slept in their guest bedrooms, gathered for family birthday parties, prayed with those going through the worst that life brings and acted like a complete fool at another’s wedding. I do what I can to help them, fundraising, hiring, board/team issues, strategic customer intros and more, but I’m always floored by how these founders turn around and support me.
More than 20 of our founders—most of which haven’t seen their own liquidity event yet—invested in our most recent fund. Dozens are constantly acting as references, both for LPs considering investing and founders considering signing our term sheet. Four of them recently joined us as venture partners. The list goes on, and ultimately, the energy I get from these incredibly intelligent, motivated individuals is among the most compelling reasons why I continue to ‘go against the grain’ and put it all on the line with M25 every day.
This all adds up to an incredible first decade of what we view as a multi-decade journey. We’ve backed unicorns from Chicago to Cincinnati. Our portfolio companies have hired thousands of people and been critical to the technology ‘boom’ across these flyover cities, but there’s still so much more to do. M25 was built with the long-term as the only guiding force—we’ve invested heavily to build this foundation to becoming a leading non-coastal VC firm, and we’re off to a great beginning. My partners and I are splitting fees on <$100M AUM across 7 different team members and a Platform effort much larger than firms 5x our size. We’re not here to get rich off the 2%. We’re here to optimize the 20% carry by generating excellent outcomes—for our LPs, our founders and their teams. So we will continue and quadruple-down on deploying on top of this robust infrastructure.
In the decades to come, M25 will continue to back the next generation of unicorns coming out of the Midwest—I expect we’ll have at least one unicorn in 10+ metros (would we be the first firm to do that?). We’re going to continue to buy meaningful ownership and increasingly add value not just with our robust capital and talent networks, but also by leaning in and getting more involved alongside the founders as a trusted board member. Our fund sizes will likely continue to grow, but we’ll stay true to our roots by being that first lead institutional check and not waiting until the Series A, B or growth rounds to get involved and put our capital at risk alongside the founders’ sweat equity. And we’ll continue to pursue consistent top quartile fund performance, appropriately stewarding the capital we’ve been given and multiplying our talents.
