21 Hats Podcast
Business & Finance
About
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
- ‘I’m Skeptical AI Is Going to Help Us’
This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends…
- Dashboard: Uber for Landscapers
When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial la…
- In Search of Companies More Interested in Being Great Than Big
Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants , Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner…
- Dashboard: Is It Still Worth Selling on Amazon?
When Eugene Khayman first got involved with Million Dollar Sellers , it was essentially a support group for entrepreneurs building businesses on Amazon. Back then, the opportunity seemed almost limitless. Today, ecommerce feels a lot more…
- When Employee Violence Walks Through Your Door
Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and drug tests. Both were considered trusted…
- Dashboard: The Anti-PE Marketplace
Hannah Sandmeyer, founder of Steward Market, explains the concept of ethical exits for ecommerce businesses. She details how her marketplace connects sellers with buyers who prioritize continuing the business's legacy over short-term profi…
- The Real Payoff May Be in Owning, Not Selling
Kate Morgan shares her evolving perspective on business ownership, suggesting that continuing to own and gradually transitioning operations to employees could be more profitable than selling, especially given lower-than-expected sale multi…
- Dashboard: Should You Pay $3,500 a Month for SEO?
Shawn Busse discusses how business owners can evaluate marketing proposals, specifically a $3,500-a-month SEO plan. The episode offers a framework to calculate the necessary return on investment and make informed decisions about marketing…
- When That Big Break Just Might Break You
The episode features Liz Picarazzi discussing a challenging Times Square installation that tested her trash enclosures, ultimately forcing business changes and innovation. It also touches on the dilemma business owners face in balancing im…
- Dashboard: Bringing a Bazooka to a Wine Fight
Keith Wallace, founder of the Wine School of Philadelphia, joins the 21 Hats Podcast to discuss a trademark dispute and legal battle with PhillyWine LLC. He shares the financial, emotional, and strategic costs of the litigation and reflect…
- There’s Scope Creep Around Every Corner
For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard t…
- Dashboard: Are We Overstating the Damage to Small Businesses?
Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year. Unemployment is low, corporate profits are hi…
- Do Small Businesses Still Need HubSpot?
Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content that his audience needed, and HubSpot h…
- Dashboard: A Different Way to Buy Marketing
Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he co-founded, offers a different path: subscri…
- How Do You Sell HR to Owners Who Don’t Think They Need It?
Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership , to bring that expertise to companies that need help. A…
- Dashboard: She Built a Business by Learning to Run Her Home
In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a pe…
- Are You Pricing for Your Clients or for Your Business?
Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks D…
- Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?
Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks an…
- Managing People Is Hard: When Does Demanding Become Toxic?
It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every in…
- Dashboard: A $2 Million Bet on Banana Ice Cream
Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he spent years searching for a business to buy—and found nothing. Th…
- It Took 25 Years to Get Here
Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In fact, Jennifer and Jaci say they’re finally climbing out of wha…
- Dashboard: The Case Against Pay for Performance
For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more. That’s how motivation works…right?This week, management consu…
- For Business Owners, It’s One Battle After Another
It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming over everything is the still-uncertain impact of artificial in…
- Dashboard: Does Entrepreneurship Have a Perception Problem?
It does in this sense, says Victor Hwang, founder of Right to Start, an advocacy group that works to expand entrepreneurial opportunity: While starting a business can be daunting, many Americans assume it’s even more daunting than it actua…
- What’s Harder Now: Getting a Job or Starting a Business?
Despite the waves of uncertainty crashing across the economy, this week we hear from three owners who feel cautiously good about how their year has started. David C. Barnett budgeted for slightly less revenue in 2026, but he’s operating mo…
- Dashboard: Can a Digital Bank Deliver for Business Owners?
In this sponsored conversation, Mike Butler, CEO of Grasshopper Bank , argues that business owners shouldn’t have to choose between speed and stability when it comes to their bank. Grasshopper has no branches, but it does offer full-servic…
- When Your Business and Your Values Collide
For the past six years, we’ve done our best to avoid talking politics on this podcast. By focusing on the business realities owners confront every day, we’ve tried to create a space where people with very different perspectives—from differ…
- We Can’t Afford to Wait on AI
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 p…
- Dashboard: Searching for Some Tariff Certainty
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 administr…
- Dashboard: Where Do You Go for Unbiased Exit Advice?
Sooner or later, most business owners run into the same unsettling question: How do I actually get out of this thing? Pass it to family? Sell to a competitor? To key employees? To private equity? To an ESOP or an Employee Ownership Trust?…
- Hot Seat: Three Owners, No Easy Answers
Sometimes the best conversations start with a simple question—and then another, and another. This week, we put Kate Morgan, Jaci Russo, and Ted Wolf in the hot seat and fire away: Are you hiring? Are you finding impressive job candidates?…
- Dashboard: Where Do You Turn When You’re Stuck?
Kelly Berry’s introduction to small-business ownership came at a moment when most new parents are focused on something else entirely. She had just come home from the hospital after giving birth when her husband handed her a personal guaran…
- We’re Trying to Outgrow the Valley of Death
Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And suddenly, the systems that got you here start to break. That’…
- Dashboard: Why Chasing Growth So Often Backfires
For most business owners, growth is the goal. More customers. More revenue. Bigger numbers. Bigger opportunities. And often, more pressure. But what if the way most of us think about growth is actually setting us up for trouble? Economist…
- I Can Help with AI. Do Owners Want Help?
Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is read…
- Dashboard: One Industry Just Got an AI Playbook for Running a Business
Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business —helping…
- I Expect to Grow This Year. Should I Hire Now?
Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hi…
- Dashboard: A Grand Experiment in Buying and Building Small Businesses
Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownersh…
- I’m Looking for an Exit
Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live.…
- Dashboard: Why 2026 Will Be a Big Year for Small Businesses
This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good things. Chief among them are a series of tax cuts that are com…
- Do Business Owners Really Want Balance?
Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena…
- Dashboard: No Text Book Can Prepare You for This
This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which yo…
- The Old Rules of Hiring Are No Longer Working
For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re fa…
- Dashboard: This Company Covers All of Its Employees’ Health Care
This week, Adam Russo, co-founder and owner of The Phia Group , explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase heal…
- Do You Have the Stomach for This? 2025 in Review, Part 2
This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell…
- Dashboard: You Can Still Save on 2025 Taxes!
This week, Gene Marks tells us it’s late, but it’s not too late to reduce this year’s tax bill. There are still steps you can take, including writing off receivables and inventory and kicking money into a retirement plan. You might even be…
- Do You Have the Stomach for This? 2025 in Review, Part 1
This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay…
- Dashboard: This Is Killing Small Businesses
As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in America. The picture John paints this year, based on his own observa…
- Three Branches, Three Brands: Anatomy of a Rebrand
This week, special guest Rich Jordan takes us inside a marketing challenge presented by his successful acquisition of home services businesses. Do you keep the legacy names of those businesses to preserve local trust—at the cost of running…
- Dashboard: Your Forecast Will Be Wrong. Do It Anyway
Most business owners know they should build a forecast for 2026. But many won’t—because it feels intimidating and time-consuming, and let’s be honest, it’s almost guaranteed to be inaccurate. This week, Tracy Bech, founder of The 60 Minute…