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Matt Castellini works as a Senior Associate at Lakeshore Ventures, which is part of Alumni Ventures Group. He will be graduating from Booth in June 2022. You can find him on Linkedin or Twitter. This is a condensed version of an interview originally published in October in Chicago BusinessChicago Booth’s student-run newspaper.
The easy answer is that both my dad and brother attended Booth and have not stopped talking about it for my entire life. I am pretty sure I had Chicago Booth onesies as a toddler...
But what drew me to Booth ultimately was the storied nature of the university's economics department and the incredible course offerings and resources dedicated towards venture capital. I have loved economics ever since my senior year of High School. I majored in econ at Notre Dame, so I could not pass up the opportunity to learn at the institution that has fundamentally shaped modern economic theory.
I also knew I wanted to pivot into venture capital, and I could not think of a better place to do so than Booth. I researched the career paths of many VCs in the Chicagoland area and saw that a large number of them went to Booth. I also noticed Booth alumni went on to some of the best VC funds in the world. Finally, I knew I would receive an excellent education that I could directly apply to my internships (and soon full-time role) in venture capital.
Tell us about how you got started on your podcast?
I always knew I wanted to start a podcast. I have listened to podcasts daily ever since college. When I realized the venture capital ecosystem is littered with podcasts, I decided to combine my hobby with my career interests.
The decision to base it around Chicago developed during the Chicago VC Trek that the Built@Booth club hosted last year. I was amazed at how impressive and approachable the VCs were who came and spoke with us. They each had incredible backgrounds and insightful comments about different markets and trends. I found it fascinating these highly competent and successful people built their successful VC funds right here in Chicago. After that Trek concluded, I knew I had found the perfect subject matter to tap into: venture capital and entrepreneurship in Chicago.
Let's talk about the beginnings of your podcast – was it easy to invite VCs to speak with you?
Yes, incredibly. The first VC I reached out to was Lance Dietz at KB partners. He's a Booth alumnus, and he spoke to us at the Chicago VC Trek. We immediately hit it off during the trek, as we both have a passionate interest in Duke Basketball. I decided to email him a month or so after the Trek to remind him who I was and ask him to come on the show. He accepted instantaneously.
Following Lance, I emailed all of the VCs involved in the Trek, and they all replied yes. At that point, I had filled out 8-10 weeks of programming. In my mind, I officially had a podcast.It's funny to think about now, but I legitimately thought I would only be able to get my dad to say yes to coming on the show. I even prepared a whole agenda for what we would talk about.
I cannot stress enough how wonderfully surprised I was at the beginning of this process. Every Booth alumnus, and for the most part every Chicago-based VC, said yes. I probably should not have expected anything different, but it's something I will never forget and still makes me proud to be a part of this ecosystem today.
What is your long-term vision for Chicago Capital?
We are very interested in expanding the show beyond the geographical limits of Chicago. There are so many MBA and undergraduate students who take the lessons they’ve learned here in Chicago and started companies or funds elsewhere. We think the community is much larger than just the city of Chicago, so we are actively looking to interview all guests with a connection and a special place in their hearts for the Windy City.
Will you share some nuggets of wisdom that have stood out to you as you have interviewed VCs?
Learning to double down on your strengths and outsource your weaknesses is truly a superpower.
Any career pivot is possible if you give yourself the proper runway and strategy.