21 Hats Podcast

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 actually is. For six years, Victor and his organization have tried to address that concern by removing barriers to entry and spreading awareness of entrepreneurial opportunities. In this episode, Victor discusses the progress Right to Start has made, including significant recent steps in Oklahoma. He also has big plans for the 250th celebration of what he likes to call America’s startup.

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 more efficiently and expects to turn a bigger profit. Jaci Russo is hitting her revenue projections—and after implementing a profit-first accounting system, she says the results have been “eye-opening.” And while Lena McGuire isn’t quite on track to meet her aggressive goal of doubling her business this year, she’s doing far better than she did a year ago.Along the way, we talk about getting runaway software subscriptions under control, figuring out how businesses get discovered in an AI world, and why Jaci’s health plan charges almost three times as much to cover female employees as it does comparable male employees. And we consider a question that might have sounded ridiculous not long ago: Has it become harder to get a job than it is to start a business?

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-service lending — with the quick decisions you might expect from an alternative lender and the rates you’d expect from a traditional one.Butler also explains how the bank is using AI to simplify everyday tasks — like finding a specific transaction in seconds instead of digging through statements — and we talk about a question many owners still wonder about: Do you lose something when you give up the local banker relationship? Along the way, we discuss which businesses are the best fit for Grasshopper, what customers actually value most, and why Butler decided to merge the bank with a larger company, Enova.

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 different industries and different parts of the country—can still learn from one another. That’s something we take seriously. But we also live in the real world. And lately, the real world has been making that separation harder.On this episode, Paul Downs, Kate Morgan, and Liz Picarazzi talk about those moments when business and personal beliefs collide—and when staying silent may not feel like an option. They’ve each faced uncomfortable questions: What do you do when an employee says something you find objectionable? Are there customers you simply won’t work with? How do you stay true to your values without putting your company at risk? There are no easy answers here. And not everyone will agree on where the line should be drawn. But as always, there’s real value in seeing how other owners handle tricky situations.

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.

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? Or maybe just shut it down?There’s no shortage of advice—but almost all of it comes with strings attached. Most advisors know one path best, and not coincidentally, it’s the path they’re paid to promote. Sorting through the options on your own can feel overwhelming, expensive, and risky. What if there were a place to get an honest, apples-to-apples comparison—one that looks at your specific business and lays out what really fits?That’s the problem Sonali Kothari is trying to solve with Zolidar, a startup she co-founded. In this episode, she explains how the company is building a tool to help owners think clearly about their exit—and why that process shouldn’t start five years too late. You can even test-drive it yourself with Zolidar’s free 10-minute Day Zero Guide for a preliminary assessment.

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? What was the worst job you ever had—and did you learn anything from it? Have you bought crypto? If you had $10,000 a month to spend on marketing, where would it go? Should a marketing agency ever turn its marketing over to another marketing agency? What’s holding you back? What’s the simplest thing you’ve never quite figured out how to do?None of these are trick questions, but they don’t necessarily have easy answers. Kate admits she’s never opened her accounting software. Jaci says one of the best things that ever happened to her was getting fired. Ted recounts losing 40 percent of his company’s revenue in a single weekend. Running a business means living with trade-offs, uncertainty, and the occasional punch to the gut. As Jaci reminds us, it usually works out—one way or another. But that doesn’t mean the answers are simple when you’re in the middle of it.

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 guarantee to sign. He had quit his job to start a business.“So if this fails,” she said, “you’ll be unemployed and we’ll be homeless?”“Yep,” he replied.That moment made the risks of entrepreneurship very real—and it helped set Kelly on the path she’s been on ever since. She went on to earn her MBA, work with economic-development organizations, and eventually launch her own business running peer groups for business owners. Her focus has always been the same: helping owners navigate the challenges they face—together.In this week’s Dashboard, Kelly shares what she’s seeing on the front lines of small business, why peer groups can be so powerful, and how she’s working to bring that support to owners in rural communities who may not have access to in-person groups. She also talks about what it takes to build her own business along the way. And if you’d like to explore whether a peer group might be right for you, you can start with a short quiz she’s created.

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’s where Liz Picarazzi finds herself right now. “We’re in the valley of death,” she says. “And we really need help.” Liz’s company, Citibin, made the most recent Inc. 5000 list, but Citibin has also hit that dangerous in-between stage—too big to run on improvisation, too small to have put in place all of the processes it needs.So Liz is trying to grow her way out of the valley. She’s hired a marketing agency. A growth consultant. And two AI advisors. She’s testing new domestic fabricators. And she’s rebuilding her website from the ground up—because right now, it’s generating no more than 10 percent of sales, and she knows it can do better. The site hasn’t kept up with her expanding product line, and it isn’t even optimized for search engine discovery, let alone for generative AI discovery.Talking it through with Paul Downs and Jaci Russo, Liz confronts some uncomfortable questions: How much copy is “enough” for AI? How transparent should pricing be—especially for a premium product whose prices could scare away some customers? And who has a better feel for the company’s story—the owner who’s lived it or the agency that has more experience helping businesses connect with customers? Not surprisingly, Liz and Jaci have different instincts on that one. What follows is a candid look at what it takes to rebuild a growing business at the dawn of a new era.

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 Gary Kunkle has spent years studying what really drives business performance. Not in headlines or case studies—but in large sets of real-world data. And what he’s found is that fast, aggressive growth often creates risks that owners don’t see until it’s too late.One reason is this: His research indicates that in most companies, about 20 percent of customers generate almost all of the profit. Most of the rest barely break even. And a surprising number quietly lose money. So when you chase growth, you’re often just adding more of the wrong customers—more complexity, more strain, more work, and less margin. In this conversation, Gary explains why steady, disciplined growth tends to outperform flashy expansion—and how understanding your own numbers can help you avoid the traps that derail so many otherwise strong businesses. Want to learn more? You can go to Gary’s website or email him directly: gmkunkle@yahoo.com.

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 ready to listen. “I don’t know if you’ve seen Don’t Look Up,” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here—or just a lot of interest and polite nodding? And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch. This 21 Hats Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.

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 them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly because it offers a practical, step-by-step playbook that helps owners think through pricing, staffing, cash flow, and growth decisions, using AI to guide—not replace—their judgment. This week on Dashboard, Ryan walks us through what happens when one industry gets an AI playbook for running a business—and why landscaping may be an early glimpse of what’s coming for a lot of small business owners.

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 hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off people she cared about—and she’s determined not to repeat that experience. But if she waits and the clients do sign, she risks something else: overloading her existing team, burning people out, and falling behind before she can recruit and train new hires. The pressure is even higher because Sarah has already set an aggressive revenue goal for 2026.Plus: Jaci Russo explains why she’s adopted a different approach to planning and budgeting. Instead of guessing how much she can afford to spend, Jaci is changing the order of the math. After revisiting Mike Michalowicz’s Profit First—prompted by a story highlighted in the 21 Hats Morning Report—she’s begun setting profit targets first and forcing every other decision, including hiring, to fit around them. It’s only been a few weeks, but Jaci says the shift is already changing how she thinks about risk, growth, and what she can actually afford.

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 ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employee retention. This week, Michael Brown, co-founder and CEO of Teamshares, returns to the podcast at a pivotal moment. Teamshares is preparing to go public—a move that raises obvious questions for a company built around long-term ownership and patient capital. We talk about what Teamshares has learned about buying businesses from aging owners, what employee ownership really changes inside a company, and what is likely to happen when an experiment like this collides with the public markets.

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. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believes a strategic sale makes the most sense, and she’s working her network to find the right buyer. This week, she talks through her plan with David C. Barnett and Ted Wolf, two owners who—unlike most—have actually sold businesses and lived with the consequences. They push Kate to think carefully about her options and the pitfalls that trip up so many owners.Plus: One reason Kate is ready to sell is that she’s recently published a book, and she’d like to devote more time and energy to accepting speaking opportunities. As it happens, Ted has written two books that he’s trying to figure out how to get published. Kate and David compare notes on the very different paths they’ve taken—David self-publishing through Amazon, Kate paying a big fee to work with Forbes Books. Both are quite happy with the choices they made.

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 coming on line and that are likely to provide more stimulus than many people are expecting. He also expects inflation to moderate and interest rates to fall enough to help out the housing and construction industries. Plus: What business owners need to know about the new tax rules governing over-time and tips.

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 McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re supposed to want. “I gotta tell you,” says Mel, “I just don't know if people were really honest that they'd say that they'd be one to spend their time at their kid’s parent-teacher conference.” Lena stresses that it’s not about right or wrong. It’s about owners making the choice that’s right for them. “You have to make yourself happy first,” she says. “It’s kind of—we always use that, ‘Put your oxygen mask on yourself first, and then you can help others.’” The owners agree that there’s a seasonality to entrepreneurship. There are periods when the business demands more, and owners have few real options. That pressure can intensify when a company is struggling—but, intriguingly, it can be just as intense when the business is growing fast. Of course, all businesses endure periods of crisis. But what if the crises never end?Show Notes: Here's the Josh Patrick column we discuss. It's well worth the read.

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 you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by her advisory board, which wanted her to reduce expenses and headcount.But Karla chose a different path.

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 facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former pastor, “is candidates are more fickle than ever, and owners need to realize that.” Paul Downs says he’s trying to figure out what’s gone wrong with his hiring process: Is it the way he uses Indeed? The way he approaches candidates? Or the differences between hiring white-collar and blue-collar employees? Jaci Russo believes companies should always be marketing their brand as an employer and always be on the lookout for good people—even when they’re not actively hiring. Plus, in a wide-ranging, end-of-year discussion recorded in December, the three owners talk about whether they hit their numbers in 2025, whether they use a formal budgeting process, what they expect in the year ahead, and how far out they can realistically see when they try to plan for the future.