21 Hats Podcast
21 Hats
The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
Episodes
Mentioned books
10 snips
Apr 3, 2026 • 35min
Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?
Shawn Busse, CEO and founder of Kinesis who helps small businesses with marketing and strategy, discusses AI reshaping content marketing. He talks about AI changing search habits, the winners and losers in traffic, authenticity versus SEO tricks, and new distribution tactics like workshops and storytelling on social platforms.
8 snips
Mar 31, 2026 • 50min
Managing People Is Hard: When Does Demanding Become Toxic?
Ted Wolf, CEO of GuideWise, brings AI and metrics-driven management; Jennifer Kerhin, CEO of SB Expos and Events, shares hands-on staffing and service leadership; Jay Goltz, serial entrepreneur, offers decades of small-business management. They debate when high standards slip into toxic behavior. Short, candid takes on yelling, hiring versus systems, handling brilliant jerks, and knowing when to let people go.
9 snips
Mar 27, 2026 • 39min
Dashboard: A $2 Million Bet on Banana Ice Cream
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.
11 snips
Mar 24, 2026 • 50min
It Took 25 Years to Get Here
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.
9 snips
Mar 20, 2026 • 45min
Dashboard: The Case Against Pay for Performance
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.
11 snips
Mar 17, 2026 • 46min
For Business Owners, It’s One Battle After Another
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.
10 snips
Mar 13, 2026 • 22min
Dashboard: Does Entrepreneurship Have a Perception Problem?
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.
9 snips
Mar 10, 2026 • 43min
What’s Harder Now: Getting a Job or Starting a Business?
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.
14 snips
Mar 6, 2026 • 32min
Dashboard: Can a Digital Bank Deliver for Business Owners?
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.
9 snips
Mar 3, 2026 • 42min
When Your Business and Your Values Collide
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.
