エピソード

  • Dashboard: The ESOP Risk Nobody Talks About

    Dashboard: The ESOP Risk Nobody Talks About
    2026/07/31
    ESOPs are often presented as one of the best ways for a business owner to exit. You preserve your company's independence, reward the employees who helped build it, and create a retirement benefit that can be life-changing for the people who stay with the business. What gets less attention is that ESOPs are still businesses. They can lose customers. They can hit hard times. And because employees' retirement savings are often tied to the company, the stakes can be even higher than they are at a conventionally owned business.This week, Roland Burdett tells the story of Miklos Systems, a Virginia defense contractor that became an ESOP in 2006 and spent nearly two decades building an ownership culture in which employees truly thought and acted like owners. Then came the pandemic, the Great Resignation, and, most recently, the uncertainty created by DOGE and deep cuts to federal contracting. Suddenly, Roland found himself worrying not only about his employees' jobs, but about their retirement savings as well.Rather than continue rolling the dice, Miklos made the difficult decision to sell itself to a larger defense contractor. Roland takes us inside that process—from explaining the decision to employee-owners, to working with an outside trustee who ultimately had the authority to approve the deal, to the surprising complexity of unwinding an ESOP after 20 years. Along the way, he offers a refreshingly candid look at both the strengths and the limitations of employee ownership, and why, in the end, protecting the people who had helped build the company meant giving up the independence they had worked so hard to preserve. This episode is brought to you by Grasshopper Bank.
    続きを読む 一部表示
    40 分
  • ‘I Want My Employees Building My Business, Not Theirs’

    ‘I Want My Employees Building My Business, Not Theirs’
    2026/07/28
    Side hustles have gone mainstream. More employees than ever are starting businesses of their own—sometimes to earn extra income, sometimes as insurance against layoffs, and sometimes because they dream of becoming entrepreneurs themselves. But what does that mean for the businesses they already work for? If you invest months in training an employee, isn’t it fair to expect that person to devote their best energy to helping your company grow? That's not an immediate concern for Lena McGuire, who's still a solopreneur. But as she prepares to hire and train her first employees, she worries about investing in people who ultimately may see her business as a stepping stone. Sarah Segal isn’t as concerned, but she does want her employees to view their jobs as careers, not placeholders. And then there's Channon Kennedy. While working full time at Silicon Valley Bank, Channon invented a woodworking tool, got it manufactured, landed national distribution, and traveled the country to trade shows—all, she says, without letting her day job suffer. And that’s what she expects from her employees with side hustles.

    Meanwhile, both Lena and Sarah are wrestling with another challenge: finding the right home for their growing businesses. Lena needs a showroom but doesn't want to sink money into leased space—and she can't find a building to buy. "I'm missing out on growth," she says. "I feel like I'm stalled." Sarah has opened a second office in Silicon Valley, but she's wondering whether it's time to leave her quirky “starter” office in San Francisco for something that better reflects where her business is headed. Buying would be ideal, but that's easier said than done in San Francisco these days.

    Plus: Sarah recently did something she hadn't done in almost a decade as a business owner—she turned on an out-of-office message and actually unplugged for a vacation. Spoiler alert: there was only one real crisis.
    続きを読む 一部表示
    51 分
  • Dashboard: Why Open Books and Employee Ownership Aren't Enough

    Dashboard: Why Open Books and Employee Ownership Aren't Enough
    2026/07/24
    One thing I've noticed over the years is that business owners love talking about employees who think like owners, who take initiative, solve problems, and don't wait to be told what to do. The harder question, of course, is: How do you actually build a company that encourages people to behave that way? My guest this week thinks most businesses actually encourage people to do the opposite.Dean Meyer is an executive coach who specializes in organizational transformation, and he believes that employee engagement has a lot less to do with perks, personalities, or motivational speeches than it does with the way a business is designed. His core idea is deceptively simple: Every manager should run a business within the business—with customers, responsibilities, and the freedom to figure out how to deliver results. It's a different way of thinking about organizational structure, and as you'll hear, it challenges some widely accepted ideas, including what employee ownership and open-book management can—and can't—accomplish on their own.Along the way, Dean explains why he says he can predict where conflict exists just by looking at an organization chart, why he believes founders become the biggest obstacle to growth once a company reaches a certain size, and how one entrepreneur used these ideas to build a company that became better at innovating, integrating acquisitions, and attracting talent. Whether you agree with Dean or not, I think you'll find that he offers a fresh perspective on a question every growing business eventually confronts: How do you build an organization that doesn't depend on the founder to make everything happen? This episode is brought to you by Grasshopper Bank.
    続きを読む 一部表示
    36 分
  • Would You Rather Own a Business in the U.K. or the U.S.?

    Would You Rather Own a Business in the U.K. or the U.S.?
    2026/07/21
    Nearly 10 years ago, Simon Bedding, who owns a manufacturing company in England, picked up a copy of Boss Life, Paul Downs' memoir about running (and almost losing) a manufacturing company in Pennsylvania. Simon liked the book enough to email Paul. Paul wrote back. And over the years, they've kind of stayed in touch. This year, as we mark the 250th anniversary of the United States spinning off from the United Kingdom, we thought it would be illuminating to get these two business owners together to compare notes. After all, their countries started with the same language and much of the same legal tradition, but two and a half centuries later, running a business on opposite sides of the Atlantic can feel very different.

    In this conversation, Paul and Simon compare taxes, regulation, hiring, health care, government support, and what it's like to build a manufacturing business in their respective countries. Along the way, there are plenty of moments when one of them can't quite believe how the other has to operate. Wait—you can't fire an employee without going before a tribunal? Wait—you have to spend a week every year figuring out health insurance? Wait—your employees don’t have employment contracts?

    And yet, for all of their differences, Paul and Simon also discover something else: Whether your factory is in Pennsylvania or southeast England, some challenges are universal. It's hard to find great people. It’s hard to fight city hall. In short, it's hard to build a successful business. And, as Paul puts it, "You're always going to learn something by talking to other business owners." This episode is brought to you by Grasshopper Bank.
    続きを読む 一部表示
    1 時間
  • Dashboard: Why Do People Keep Starting Businesses?

    Dashboard: Why Do People Keep Starting Businesses?
    2026/07/17
    Small business owners have plenty to worry about these days. According to John Arensmeyer, founder and CEO of Small Business Majority, his organization's surveys show optimism is slipping as owners grapple with soaring health insurance premiums, rising energy costs, and the higher price of imported goods. And yet, the wave of entrepreneurship that began during the pandemic hasn't faded. In fact, it's still growing. So what's going on? Why are so many people choosing this moment to start businesses? What do they think they're seeing? And perhaps the more important question: What can we do to improve their odds of success? Along the way, John also makes the case that one of today's politicians understands the needs of small businesses better than most. You may be surprised by who he names. This episode is brought to you by Grasshopper Bank.
    続きを読む 一部表示
    20 分
  • I’ll Deal with Succession Next Year

    I’ll Deal with Succession Next Year
    2026/07/14
    If you’ve owned a business for any length of time, you’ve probably told yourself some version of this: I'll deal with succession as soon as I solve whatever crisis my business is confronting right now. The problem, of course, is that there's always another crisis to solve or opportunity to pursue, and time has a way of passing.

    Jay Goltz has spent decades building a collection of successful businesses in Chicago. He knows he needs a succession plan. He knows that if something happened to him tomorrow, there’d be chaos. And he'd very much like to leave the business in the hands of the employees who helped build it. Over the years, he's considered the usual options—selling to a bigger company, to a few key employees, to an ESOP, even to an Employee Ownership Trust. But every option comes with compromises. And so, year after year, it’s been easier to focus on challenges that seem more urgent—until this past April, when Jay turned 70. "I realized," he says, "I can't kick this down the road much further."

    This week, Jay sits down with David C. Barnett and Mel Gravely for an unusually candid conversation about what makes succession planning so difficult—even when you understand how important it is. Jay explains why he has no interest in selling, why money isn't really the issue, and why he still loves going to work every day. Mel, meanwhile, offers some tough love, suggesting that if protecting Jay's family and employees really are his priorities, then something else must be holding him back.

    Mel also shares an unexpected twist in his own succession journey. After stepping away from the CEO role two and a half years ago to become executive chairman, Mel found himself pulled back into operations this spring—a reminder that even well-designed succession plans don't always unfold as expected. And along the way, David offers a blunt explanation for why many aging business owners overestimate what their companies are actually worth. The episode is brought to you by Grasshopper Bank.
    続きを読む 一部表示
    52 分
  • Dashboard: You're Probably Not Spending Enough on AI

    Dashboard: You're Probably Not Spending Enough on AI
    2026/07/10
    There have been a lot of stories lately about companies getting hit with surprisingly large AI bills. They start using platforms like ChatGPT or Claude, usage grows faster than expected, and suddenly they're spending far more than they ever imagined. Should small businesses be worried? I invited AI consultant and longtime business owner Alan Pentz back on the podcast to find out. His answer may surprise you: for most small businesses, he says, runaway AI costs aren't the problem. If anything, he thinks they're spending too little.That led us into a wide-ranging conversation about why Alan has changed his thinking on how owners should approach AI, why today's pricing is effectively subsidized for smaller businesses, when it does—and doesn't—matter which model you're using, why mastering prompt writing is becoming less valuable than many people assume, and what happens when the companies behind the large language models finally have to start making real money.
    続きを読む 一部表示
    31 分
  • What Do You Owe Your Employees?

    What Do You Owe Your Employees?
    2026/07/07
    Most business owners hope to reach the day when someone offers to buy their business. If that day comes, the payoff isn't just financial. It's validation for years of risk-taking, sleepless nights, personal guarantees, and sacrifices that most employees never see. But that success can raise an uncomfortable question: What exactly do owners owe the people who helped them get there? Should employees share in the proceeds when a business is sold? Does an owner have an obligation to find a buyer who will protect the culture and the jobs that have been built over the years? Or is the owner's responsibility fulfilled by paying people well, treating them fairly, and creating a great place to work so long as the business is theirs to run?

    This week, Jay Goltz, Liz Picarazzi, and Ted Wolf wrestle with those questions—and not always from the same perspective. They agree that employees deserve respect and appreciation. But they also point out that employees weren't the ones who pledged their homes as collateral, absorbed the losses, or spent years wondering whether the business would survive. In other words, where should owners draw the line between gratitude and obligation?

    Plus: As Liz expands Citibin beyond New York City, should her marketing reflect that shift? Or should she lean into her hometown roots and emphasize that if her trash bins can make it there, they can make it anywhere? Liz also explains her plan to capture some recurring revenue.
    続きを読む 一部表示
    52 分