Today Hyde Park Venture Partners celebrates raising a $100M Fund III (read our press release here), with an amazing cadre of investors and dedicated entrepreneurs as our partners. We are deeply aware of the responsibility that we bear to both of these constituents.

When we finished raising our $65M Fund II in 2016, I spoke about the importance of a VC’s own fundraising cycle in driving humility and empathy towards entrepreneurs in theirs. There is nothing like laying your wins, failures, and heart bare to dispassionate analysis to remind us investors of what our entrepreneurs experience with us and for us. Three years later, this is still true, and we see growing parallels as our maturing fund steps through these milestones, much as our companies do their Series Seed, A then B:

Our $25M Fund I was much like a startup’s Seed-stage financing. We had some relevant experience, a good idea, proof of concept (our local angel investments) and an incomplete team. The equivalent of friends, family, and local angel investors bet on us and the idea. For our $65M Fund II — much as in a startup Series A financing — we could show that we were doing what we said we would do, had early proof points and numbers and had rounded out our team… but yet without longevity or consistency. Now with a $100M Fund III, we have even better numbers but also consistency in performance and team. These are analogs to the scalability that investors look for in a Series B stage startup. But also like a Series B startup, we still have MUCH left to prove, and we are excited to do so. Like our Series B companies, we are largely illiquid!

We’ve also learned as startups do that the forge of fundraising makes you stronger and sharper. It reminds us that we need to be constantly ready to answer the questions “What is your strategy?”, “Why you?”, and “What do you do differently?” It’s easy for investors in less trodden regions (like our mid-continent) to get lazy about their answers because very few opportunities are actually competitive at the stage we invest. Some are, however, and all of them will become more competitive if they go well, leaving us to earn the room we so desire in a follow-on round. So what are our answers for investors and entrepreneurs?

Our strategy: We strive to be the go-to early-stage software investor in the mid-continent, the one that everyone has heard of and is willing to meet with when they want to raise a $1–8M seed to Series A financing.

Why us: This is a more personal question — smart entrepreneurs know to ask this of the specific investor who is courting them and not the firm. In our partnership, the answer ranges from, “I was a CxO that co-led a company from $50 to $400M in revenue” to “I will always respond immediately, be honest and direct and provide multiple perspectives on a problem. This sounds like bull, so talk to the entrepreneurs I work with.”

What do you do differently: The essence of our difference is our regional focus and where it allows us to excel in finding the best companies and helping them. While there are other funds in the mid-continent, none of our stage/size is so laser-focused on the contiguous region around the great lakes. The startup game is local, and these local networks are connected. This allows us to play a focused ground game to find great companies and the talent to help them grow. It also allows us to be local curators for the myriad coastal funds who now want to invest here at later stages. Our consistent relationships with a number of these firms helps our companies. While this wouldn’t be a differentiator in CA, it is here.

So that’s the story we told, and that’s what we execute on every day.

Of course, that sounds very simplistic, glib even. It reminds me of our recent annual meeting speaking with one of our most successful CEOs. I congratulated him and thanked him for a terrific 2019. He said that he appreciated it, but that when you look at the up-and-to-the-right curve with a magnifying glass, you’ll see lots of ups and downs, growing pains and hard problems to solve. Certainly, when a startup goes from 10 to 400 people in 5 years, the only constant is actually change, and change is hard.

Venture funds don’t change quite as quickly as a scaling startup, but when you look from our day one to now — 2 to 10 people, 150 sq ft shared office to our own 3,200 sq ft buildout, 0 to 50 portfolio companies and $25M to 200M in assets — we have changed plenty. When you’re such a small firm, each new team addition re-invents us. Sometimes in big ways and sometimes in small ways. In that sense, we have been reinvented eight times over. Likewise, every startup team we partner with teaches us something new, tests our assumptions and makes each day we wake new and unscripted. That’s what makes it fun.

Know any great startups? No scripts required.

‍