Episodes

  • Dashboard: Where Do You Go for Honest Exit Advice?

    Dashboard: Where Do You Go for Honest Exit Advice?
    Feb 20 2026
    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.
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    36 mins
  • Hot Seat: Three Owners, No Easy Answers

    Hot Seat: Three Owners, No Easy Answers
    Feb 17 2026
    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.
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    53 mins
  • Dashboard: Where Do You Turn When You’re Stuck?

    Dashboard: Where Do You Turn When You’re Stuck?
    Feb 13 2026
    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.
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    33 mins
  • We’re Trying to Outgrow the Valley of Death

    We’re Trying to Outgrow the Valley of Death
    Feb 10 2026
    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.
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    47 mins
  • Dashboard: Why Chasing Growth So Often Backfires

    Dashboard: Why Chasing Growth So Often Backfires
    Feb 6 2026
    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.
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    31 mins
  • I Can Help with AI. Do Owners Want Help?

    I Can Help with AI. Do Owners Want Help?
    Feb 3 2026
    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.
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    51 mins
  • Dashboard: One Industry Just Got an AI Playbook for Running a Business

    Dashboard: One Industry Just Got an AI Playbook for Running a Business
    Jan 30 2026
    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.
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    42 mins
  • I Expect to Grow This Year. Should I Hire Now?

    I Expect to Grow This Year. Should I Hire Now?
    Jan 27 2026
    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.
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    46 mins