FreightCaviar Podcast: Michael Sachaj of Hyde Park Angels (First Investor in FourKites)

Today, we sat down with Michael Sachaj, Senior Principal at Hyde Park Angels, a leading early-stage investor in Chicago. He brought us behind the scenes of the investing world, shared his views on the future of AI and what the tech holds for brokers, plus talked about the value HPA Member Eddie Leshin brings to the company.

We started off our conversation by discussing Michael’s start in the venture capital world—from launching a few companies in high school and college and attending all the classes he could about startups at Northwestern University, Michael ended up at Hyde Park Angels thanks to a friend and has worked there for more than a decade.

Throughout his career, Michael has seen many companies come and go, so it’s only natural that he knows a good start-up when he sees one—in his opinion, it is better to invest in a co-founding team than a solo founder—having multiple co-founders who are bringing different things to the table is better than having one solo founder.

We brought up the topic of AI and being careful where you invest your money—Michael emphasizes the fact that “If you’re invested in a part of the industry where in three to five years, AI will completely replace what they're doing, then that company from day one better be thinking and managing to that AI strategy.” Of course, there are parts of the industry, such as maintenance and repairs, AI can’t replace that. When asked what he could see being replaced by AI in the future, he replies: customer service. In terms of quicker response time and more dynamic responses, we will see AI being used all across the industry very soon.

Michael also touched on the subject of API calls and the element of trust—he believes that phone, text, and e-mails will make a comeback the more AI is used. Of course, only time will tell how everything will play out over the next decade or so, especially in such heavily regulated industries, such as healthcare, that deal with personal data. This is where the element of trust comes into play, he says.

He also credits his mentor and HPA Member, Eddie Leshin, whom we interviewed back in September of 2023, with helping HPA make great investments in companies such as ShipBob Inc. Thanks to Eddie’s great insights, they were able to tell which investments they should make and which ones they should pass on.