Brynn Michelich

Growing company culture is an essential mission for any business. 2020’s rapid change to work-from-home due to COVID-19 has presented itself with so many extra challenges, even companies with great work culture reputations find themselves in a tough spot to keep the team together. Chicago-based Jellyvision is one of those businesses known for great office…

Jason Fried

Email is not a new thing, but what’s really changed since Gmail launched in 2004? Not much, says HEY Email founder and CEO Jason Fried. Instead we’ve seen basically the same variations of email products ever since, but with more and more stuff that doesn’t mix well together. Ads, newsletters, personal and business emails blending…

Ben Preston

CMO of Gearflow. It’s 2020, everything is supposed to be online..and you’ll still be surprised how many functions of our society are still on the outside looking in at E-commerce. Construction, an essential business these days, is no exception and Ben Preston and his co-founder Luke Powers saw a huge opportunity to address a major…

Bryce Conlan

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…

John Wallace

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…

Dave Bowen

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…

Steve Beauchamp

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…

Brian Barnes

CEO of M1 Finance. Ever since being introduced to a brokerage as a kid by his parents, Brian Barnes loved the idea of investing. The concept of putting your money to work for you, making a high conviction bet on a company producing something in a complicated marketplace and watching it grow got him hooked.…

Darren Guccione

With our lives so dramatically increased remote and online due to the pandemic, cyber security has never been more tested. Our friend Darren Guccione from Keeper Security joins the show to tell Scott how they have seen huge spikes in cyber attacks, including ransomware and phishing attacks since we’ve all moved indoors. Darren says that…

Marie Trzupek Lynch

President & CEO of Skills for Chicagoland’s Future. Marie Trzupek Lynch knows job placement – or just getting a job in general – is tougher than it it should be for employers and prospective employees. The pandemic has only further put a spotlight on glaring holes in the job market – namely: there isn’t much…