Making the Pitch for Chicago Tech: A Conversation with Hyde Park Angels’ Pete Wilkins

What is your role at HPA?

What really first got me involved as an angel investor was the opportunity to help build a strong tech ecosystem in Chicago. And the way that I see it now, as opposed to when I started ten years ago, is that not only can we build a stronger ecosystem, but we can invest in some of the best companies in the country, which will be a benefit for investors, companies, and the community.

Do you have any examples of portfolio companies, or other startups, who use/used PR very effectively?

All venture capital firms are in the process of trying to uncover great opportunities. It helps to look at companies disrupting large markets and innovating large concepts. What PR does is provide context as to how these startups are disrupting industries, which then generates interest.

What do you look for in potential portfolio companies? How can entrepreneurs make a successful pitch?

Ultimately, if you are pitching an investor, you have to identify and talk about the problem you’re solving or the opportunity you’re creating for consumers or businesses. You have to show that there’s a strong need for a solution there, and that consumers or businesses will be compelled to take advantage of the solution you intend to create.

In terms of structuring a pitch, is there anything specific you look for?

The one thing that I would tell people is that what we’re evaluating is less about every word you’re saying, and more about your logic. For example, your financial model will never be 100% accurate — I know that. But the logic of how you’re thinking about getting to your financial goal is something that we’re evaluating. You could spend 15 days figuring out the perfect 10-year model, but it doesn’t mean anything if your baseline logic is incorrect. So really what venture capitalists are doing is trying to test your logic of how your business will work, knowing that there’s going to be a lot of evolution in the way that you are able to deliver, market, and help grow.

What trends are you noticing in Chicago tech?

The trend that is starting to emerge is that we’re being able to parlay our success both through traditional and startup businesses to grow out industries. If you look at what’s going on in the logistics industry, we have a bunch of established players, but we also have new startups that are able to harness the same talent and infrastructure to grow. If you look at artificial intelligence and IoT, we’re able to harvest companies that are traditional players (like Gogo, Caterpillar, etc.) and emerging companies like Uptake and Catalytic. We’re seeing industries like farming and B2B Marketplaces grow, and we’re able to see how Grubhub and Groupon have created new marketplaces, so I think the biggest trend is that we are moving in the evolution of our ecosystem from being immature to mature, and, as a result, we are seeing a variety of different industries flourish.

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