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June 11, 2019

Why I took the Leap Into Venture Capital

Why I took the Leap Into Venture Capital

If I’m being honest, it’s still a little surprising, even to me, that I now work in venture capital.

Telling people what my new job entails feels a little like new shoes that don’t fit quite right — but you know will be comfortable favorites with a few wears. After all, my background is decidedly not financial — I’ve worked in big consulting, the mayor’s office, and yes — a few startups. So, why did I take this leap? Well, for a few different reasons.

A belief in the investment thesis.

I’ve lived in the Chicago area since 2005, and in that time, I’ve grown a deep-seated belief in the opportunity of the Midwest. I graduated a couple of times from schools in the area, and saw friends leave for the coasts, and looked at them like they were crazy — with incredible companies here, a lower cost of living at a high quality, and a deep base of diverse talent, I have always felt strongly that the opportunity to grow my career and build my life in the Midwest was right for me. Hyde Park Venture Partners shares these ideas and is working every day to grow the Midwest technology ecosystem so that this rings true for many more people. When I was interviewing, a friend suggested that just looking for startups in the Mid-continent would feel restrictive, but I feel invigorated by the idea, and knew that the right firm for me would feel that way too.

An opportunity to grow my career in a new direction.

Over the last few years, I’ve found myself scouring BuiltInChicago, ChicagoInno, 1871 events, and more to see what was new and cool in tech in Chicago. I found myself getting very excited about the new ideas I was seeing, and the people that were founding them, and wanting to learn more — just like I’ll be doing as I source companies for potential investment. I was working at one of those companies myself and saw the opportunity to take a broader view of the ecosystem but as my full-time job. In addition, one of my favorite parts of my most recent job was the role I played in planning the future strategy of the company, including poking at the new ideas my colleagues were bringing forth to see how we could make them better. It felt a lot like the diligence work I’ll do now on future HPVP investments. In short, I was and continue to be excited about learning the day-to-day work and growing my skills in a new direction.

Their belief in me, as me.

At this point in my career, I’m fortunate to feel like finding a new job is a two-way street, which meant that I knew my next job had to share my values and encourage my ideas — and I could honestly do the same. I had to make sure the HPVP team liked the everyday version of myself, not just the on-my-best-behavior interview self — and wanted to make sure I felt the same way about them. The questions I asked during the interview process — “Will finding diverse founding teams be a priority?” (definitely), “How do you feel about Govtech?” (pro — with a lot of room for me to advocate), got at the heart of what I care about — and the genuine enthusiasm of their responses demonstrated we were on the same page. Each answer they gave confirmed both that I wanted to join the team, and that I was the right fit for them.

I’m ready to dive right in.

What I’ll be looking at going forward

Like all members of the HPVP team, I’m looking forward to investing in a breadth of tech-enabled companies, but there are a few areas that are very close to my heart. My experiences founding Flag Analytics — which enabled police departments to use data science to evaluate their officers, helping fix Healthcare.gov while at Accenture, and working inside the City of Chicago Mayor’s office highlight the intersection of three things I care about — enabling governments to use technology better, healthcare, and data science. In particular, I think the time is right for a new set of companies to dramatically improve how government services constituents, whether that’s enrolling in benefits programs, paying parking tickets, or contacting elected representatives.

So, if you have a technology solution for a government-related problem (or any other problem!), and are based in the mid-continent, find me at allison@hydeparkvp.com. I can’t wait to hear about it.

Written by
Allison Weil
Allison Weil
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