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).…
CEO of Proxfinity. Proxfinity, like almost all companies in the event space, got slammed by the consequences of the COVID-19 spread. However unlike most other event companies, Proxfinity had an existing product, their wearable tech badge that lights up when around people with like-minded interests at networking events, that they could reimagine to help achieve…
Founder of Narrative Advantage. Bryce Conlan and Scott share something of a kindred spirit, cleverly termed the “unemployable”. That’s not to say anyone is actually unemployable, but there’s a certain type of a person that naturally gravitates towards new ideas, better ways to perform a service and work independently to do so that doesn’t always…
CEO and COO of Pear Chef. Founder Danielle Drabkin and COO Jennifer Wei join the show to catch up with Scott about the growth of Pear Chef, a private-chef service amenity serving fresh meals and drinks. Pear Chef provides weekly menus to buildings that residents can order from on the Pear Chef site, made on-site…
Founder of ExpandHR. Ben Schack of BMO Harris and Shayna Atkins of ExpandHR join the podcast with Scott to talk about what founders truly need from a program and how this partnership evolved into the female-founder driven program it is today. Chicago is a growing fintech city with a solid foundation to launch new companies…
Co-Founder of SportBLX. Ever thought as a fan how a team or player should be paying you for all the time you invest watching them play? It’s a level of engagement that was previously unheard of. Now, SportBLX is pioneering a way for you to do that by investing in the teams and players themselves.…
CEO of Industrious. Jamie Hodari, co-founder and CEO of Industrious, joins the show to talk with Scott about the rapid change in office space and why momentum was already turning towards increased remote work pre-COVID. The days of centralized headquarters with hundreds of employees are dwindling, with teams expanding globally and the need for smaller…
CEO of Workbox. There’s been a saturation in the tech incubator space for years now, and unfortunately the pandemic has provided somewhat of a reckoning. Without the ability to host events or provide workspace, the value for founders to join these programs has declined. John Wallace saw an opportunity to improve on the co-working accelerator…
CEO of Purchasing Platform. Dave Bowen is what Scott likes to call a “refounder”. Dave was at the end of an earn out period from the acquisition of his previous business when he got approached by the Purchasting Platform team for help. Pretty quickly they mapped out the mistakes that were made and realized they…
CEO of Paylocity. It’s easy to overlook how important HR, payroll benefits, compliance etc are what really make you standout to hire – and keep – top tier talent in your company. Paylocity’s all-in-one software platform helps HR pros achieve their best with automation, data-driven insights & engagement. Steve Beauchamp joins the show to talk about how…