David McFarland

When David McFarland was got a job as an actuary out of college, he was working at an insurance firm where he first saw how data wasn’t being optimized. Later after working alongside Kyle Nakatsuji at auto insurtech company ClearCover, he saw how Kyle’s model could apply to all of small businesses and more importantly,…

Aaron Letzeiser

CEO of Obie. Insurance tech has been an industry ripe for disruption with a slew of companies like ClearCover, CoverWallet, Kin and Vouch making waves recently. Obie, a combo insurance brokerage and risk management platform is geared to join the fray by focusing on serving real estate investors from multiunit to single family residences (SFRs).…

Travis Hedge

Cofounder of Vouch Insurance. Insurance is one of the less sexy parts of running a company — and that’s especially true when working with the legacy companies that are far removed from the startup way. Newer business models often don’t neatly fit into traditional insurers’ outdated categories. Sometimes plans need to be patch worked and…

Sean Harper

Chicago Entrepreneur Scott Kitun and Kin founder Sean Harper tackle why many startups from the Midwest keep getting burned by similar startups from the coasts (hint: it’s not a talent issue). Kin is a fast-growing, tech-first, property insurance company co-founded by Sean Harper. Harper goes into the weeds when it comes to finding what impacts…