21 Hats Podcast

Chris Campbell, a serial entrepreneur who built and sold multiple businesses, launched Banana Daddy, a bold banana soft-serve concept backed by a $2 million opening bet. He talks about pivoting from buying to starting, intensive product testing including an Art Basel truck, and surprising demand like morning ice cream and long lines that required crowd control.

Jackie Russo, a Louisiana marketing CEO, talks branding, trade-show prep, AI and a shocking gender gap in employee health premiums. Jennifer Caron, an events operator, shares lessons on scaling, systems, and avoiding growth mistakes. Paul Downs, a longtime custom-furniture maker, covers manufacturing, Google-driven sales, and multi-decade growth challenges. They trade fast, practical takes on tradeshow ROI, trademarks, and long-term survival.

Kelly Allen, a management consultant steeped in W. Edwards Deming’s methods and board advisor at the Deming Institute, challenges common pay-for-performance beliefs. She explores why incentives can distort behavior and prompt metric gaming. The conversation highlights system-focused fixes, real-world examples of removing commissions, and practical steps for leaders to experiment with alternatives.

Ted Wolf, CEO of an AI implementation firm, Jay Goltz, veteran Chicago entrepreneur, and David C. Barnett, business broker and advisor, discuss how rapid AI adoption, rising energy and tariff risks, lenders demanding AI plans, and sales-tax surprises are reshaping owner decisions. They explore quick-payback tech investments, lending risk shifts, and spotting opportunities when competitors falter.

Victor Hwang, founder and CEO of Right to Start, fights to expand entrepreneurial opportunity across the U.S. He discusses how starting a business seems scarier than it is. He contrasts easy digital tools with systemic frictions like healthcare and payroll. He describes redefining startups as gradual side hustles and highlights policy wins such as Oklahoma’s reforms and growing state momentum.

Jackie Russo, CEO of Brand Russo, a marketing agency leader; Lena McGuire, CEO of Spoka Kitchen & Bath, a home remodeling operator; and David C. Barnett, a business broker and advisor, discuss running businesses today. They cover Profit First accounting wins, using AI and SEO for discovery, trimming costly software subscriptions, health insurance pricing disparities, and whether launching a business beats finding a job.

Mike Butler, CEO of Grasshopper Bank and a digital-banking veteran, explains a branchless bank that offers full-service lending. He discusses fast digital onboarding, using alternative data and AI to speed lending and find transactions, balancing bank-like rates with quick decisions, and the strategic merger with Enova to scale digital deposits and lending.

Liz Piccarazzi, CEO of CityBin, talks hiring immigrants, installer travel safety, and balancing employee welfare with business needs. Kate Morgan, CEO of Boston Human Capital Partners, covers workplace values, confronting racist conduct, and when owners refuse clients. Paul Downs, CEO of Paul Downs Cabinetmakers, discusses client choices, company culture, and how values shape business decisions.

A lot of business owners are taking a wait-and-see approach with artificial intelligence. They’ve heard the hype—but they’ve also heard about the slop, the hallucinations, and the research suggesting many AI projects fail to deliver. For plenty of owners, that’s reason enough to assume this might be another passing obsession—like Y2K, Clubhouse, or the metaverse—and to sit back until the dust settles.But not these three owners: David C. Barnett, Jaci Russo, and William Vanderbloemen have decided that waiting is the bigger risk. They’re taking courses, they’re teaching courses, they’re building agents, and they’re rethinking processes and workflows—all in search of an edge that may not be available forever. And they’re already seeing results.In this episode, they share what’s actually working so far, including some early experiments that could reduce their reliance on Google AdWords. They also talk candidly about what they won’t do with AI, how they sidestep the slop, and why each of them believes this is one of those rare moments when experimentation isn’t optional.

Yes, says Gene Marks in this week’s Dashboard, the Supreme Court’s tariff decision, while correct, has created a mess. No, you shouldn’t make any plans to spend your tariff refund money. And no, there’s no telling where the Trump administration might be heading. But he does offer this one shred of certainty: For many businesses that have been paying the so-called reciprocal tariffs, if they plan for a 15-percent tariff rate going forward, they’ll probably be in reasonably safe territory.