“Small Business” can be a bit of a misnomer.
On this week’s episode of The Upswing, WTMJ’s Jeff Sherman was joined by Pat Miller from the Small Business Owners Community to talk about the unwritten rules for small business owners and Koss Corporation’s Martin Moore to discuss the latest with Starbucks, AI and more.
Jeff Sherman first went over a few big business headlines from the week:
- Pete’s Pops announced that it would be opening a new location in Grafton. Jeff previously spoke with Pete’s Pops current owner Ian Robinson last October which you can listen to below.
- Jeff also went over the latest housing market numbers in southeastern Wisconsin outside of Milwaukee, including Mukwonago, Cedarburg, New Berlin and Slinger.
Jeff Sherman was first joined by Pat Miller, founder of the Small Business Owners Community to talk about the do’s and don’t’s of owning a small business.
“Imposter syndrome is the grim reaper of small business owners,” Pat told Jeff.
They also talked about the current challenges of small businesses, whether that’s supply chain issues for those that sell goods to finding clients for service providers.
“People who trust the process go out of business.” “the spoils go to those who hustle.” He also recommended that rising entrepreneurs should surround themselves by other business owners to help find success and having a coach.
Jeff asked Miller about his upcoming webinar on April 29th on doing business better. Plans for it had shifted due to huge economic fluctuations that occurred throughout the beginning of 2025. Keynote speakers at the webinar include best-selling author and entrepreneur Seth Godin, productivity expert Julie Miller Davis from Captivate.fm founder Mark Asquith.
When asked by Jeff Sherman to define success, Pat Miller answered, “freedom of time and freedom of money.”
Jeff Sherman was then joined by his Future of Almost Everything in Wisconsin co-host Martin Moore. They talked about the return of baristas customizing doodles on cups for every customer. Similarly, they talked about the challenges of creativity-focused careers and how artificial intelligence affects those careers. They also talked about social media platform Bluesky introducing their own verification process and a new art installation coming to Wauwatosa.
The Upswing is presented by Horicon Bank.
