Oliver Wiener is an entrepreneur and financier with expertise in the digital realm. He is the Founder and Managing Partner of Kensington Merchant Partners, an investment firm in the evolving financial and technological ecosystem. He was formerly a Portfolio Manager at Standard Investments and a founding partner at BTIG, and is the founder of The Association of Digital Asset Markets. He graduated from UW–Madison with a dual major BA in International Relations and Political Science. He now sits on the Technology Entrepreneurship (TEO) Advisory Board and the College of Letters & Science Board of Visitors.
We asked Wiener five questions to learn about his career journey and get his advice for entrepreneurs who also want to be leaders.
What is your personal journey through entrepreneurship and where are you today?
I started my first company on campus in the summer before my sophomore year, in the mid-90s, called Wiz Kidz. There were a bunch of older kids in my social circle that were running small businesses. One was doing laundry, one was doing Culligan water bottles. I loved the idea of having a small business, and they inspired me, but my friend and I were more technologically inclined. At that period of time, students had just started to bring personal computers to campus, and they were really expensive. Kids would move in with a multi-thousand dollar-Dell computer in boxes. Nobody really knew how to use them, but we did. And so we would set up people’s computers when they moved in.
The school also had a CD-ROM that you would buy called WiscWorld which had the TCP/IP packet to install. It was like $20 or $25 at the bookstore. But the license said that once you had it, you could install it for free multiple times. We would charge people for our install services and give them WiscWorld for free. There’s nothing like buying something for $25 and charging $20 to install it. At a similar time, there were a couple of other college campuses where similar businesses were born: one was called Geek Squad, which eventually sold to Best Buy, and one was called Firedog, which sold to Circuit City. We did not have such luck. We could never figure out how to scale. And that was the end of that entrepreneurial journey, but it was innate in me to start that entrepreneurial experience in Madison and go through trials and tribulations.
Today I run a small business that is not in that same ecosystem. But the reason I ended up here—and a lot of my career experience—has been about taking the entrepreneurial operator step, about walking off the edge of a cliff, about having the risk and taking that desire to not just have a job, but to be building a company while I’m building a career.
What drew you specifically to being involved in leadership of TEO at UW-Madison?
The inspiration from Tom Erickson, former founding director of the School of Computer, Data & Information Sciences, and Ian Robertson, the former Dean of the College of Engineering (CoE), who both helped create TEO as part of the drive to bring NSF funding and other programming to campus. I saw that as the gateway to supporting a larger entrepreneurial environment—as we’ve now birthed, as Dean Ranjan has come in, and the staffing of TEO with Bonnie and team. There’s a lot that we produce at WARF and in the research university, but there’s also an entire ecosystem of undergrad entrepreneurialism that exists. And it’s the matching of the two in support of those journeys, which was reflective of my own journey that I saw echoes of, that I was excited to support and be a part of. No corollary story is the same, but to bastardize Twain: history doesn’t repeat, but it sure does rhyme.
As an advisory board member, what is your role? What do you enjoy most about your involvement with TEO?
The board has evolved, the program has evolved, our experience and responsibilities have evolved. The evolution continues because Dean Ranjan is new, the School of Computer, Data & Information Sciences (CDIS) launching is new. Those movements are changing our roles in a number of ways. Regardless, I enjoy working with TEO’s programming team, the support staff, and the other colleagues for sure. The people.
From your own experience, what was the most valuable lesson you learned that you now bring to your leadership?
In entrepreneurialism and leadership, in my opinion, it’s about passion. You can’t teach somebody the desire to be entrepreneurial. It’s not necessarily an innate trait—and maybe it has to do with some level of unintelligence because you crave the danger of it, the excitement. I tell people I have lots of days that are twos and lots that are eights. You can’t convince somebody to want to live like that.
With leadership specifically, my father used to say that sometimes—or many times—it is actually the person who speaks the quietest that gets the room to listen. I’m a fairly large personality who speaks with a big booming voice, and he used to remind me that sometimes you just have to speak quietly so that people around you get quiet to listen to hear you speak. But it’s not just about getting people to hear you, but getting them to listen to you. That is how you become a leader. There are many other traits that it takes to be a great leader, but that is one that resonates with me right now that I will pass on.
If you could give one piece of advice to aspiring entrepreneurs starting their journey, what would it be?
Don’t be afraid to hit the floor and get up. It’s all about how you rebound. That’s generally just a life thing, but in an entrepreneurial life more so than anything else, you will get hit and you will hit the ground and you do need to stand up and dust yourself off.
There are also a lot of amazing entrepreneurial resources across campus in different ways. As Dean Eric Wilcots (L&S, now interim Chancellor) has recently said, “There are a lot of doors on campus. You just need to start opening some of them.” It’s a big place, and it’s daunting for people, but know that you can just start walking in places and opening doors.
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Featured image: Oliver Wiener, Founder and Managing Partner of Kensington Merchant Partners and TEO Advisory Board member.
Written by: Bri Meyer