21 Hats Podcast

21 Hats
  • 5.0 (32)
  • 创业
  • 一周一更

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.

  1. 2天前

    Dashboard: Tracking the Entrepreneurial Economy

    This week, Brandon Gray, a partner with CRI Simple Numbers, talks about how his firm tracks the performance of what he calls the entrepreneurial economy. As we all know, what’s happening on Wall Street doesn’t always reflect what’s happening on Main Street, which is why Simple Numbers tracks the performance of 100 smaller businesses. Right now, Brandon says, the performance of those businesses isn’t looking great, which doesn’t necessarily bode well for 2026. How should an individual owner make use of that information? Brandon has some suggestions.

    33 分钟

  2. 5天前 · 附赠内容

    Best of: We Charge What We Need to Charge

    This week, we’re replaying one of my favorite conversations of the year, a Q&A session we recorded in May at our 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of Zingerman’s Community of Businesses. If you’ve already listened to our conversation with Ari, I encourage you to listen again. It’s worth it. And if you haven’t heard it, well, you’re in for a treat. Much of the discussion focused on a topic that haunts just about every business owner, and that’s pricing. Specifically, Ari talked about how he learned to charge enough to run a healthy business and why he’d rather go out of business charging what Zingerman’s needs to charge than go out of business never knowing whether customers would have paid the true cost of great food and great service. (Spoiler alert: They have not gone out of business.) Not surprisingly, the 21 Hats Live participants had lots of questions for Ari, including how he and his partners decide whether to launch a new business, how he and co-founder Paul Saginaw have maintained their partnership for more than 40 years, how he and Paul are approaching succession, and whether he thinks of himself as successful, which prompted Ari to share that his mother never stopped pleading with him to take the LSAT. You know, just in case. We’re re-playing the episode in part because we took Thanksgiving week off from recording but also because it offers a little taste of what it’s like to attend a 21 Hats Live event. As you may have seen in the Morning Report, I’ve just announced that our fourth annual in-person event will take place in Cincinnati in May. Once again, it will be a terrific opportunity to connect with others who understand what it takes to build a business. If you’ve ever wished you could spend more time with people who really get what you’re going through, this is your chance. We will have peer group conversations on topics you help pick. We’ll get VIP tours of iconic local businesses. We’ll eat good food. We’ll build relationships. And we’ll leave inspired. But spots are limited. For more information and to register, please check the newsletter I sent out on Sunday. Or shoot me an email, and I’ll make sure you get the invite. You can reach me at loren@21hats.com.

    59 分钟

  3. 11月28日

    Dashboard: Finding Employees Is Harder than Finding Customers

    This week, Rob Levin, who is co-founder of WorkBetterNow and who has just published a new book, the “New Talent Playbook,” talks about what he considers to be a talent crisis for small businesses. As Rob points out, you might think hiring would be easy these days given all of the recent corporate layoffs—but the people leaving big businesses are probably not the right hires for smaller businesses. Instead, Rob offers a step-by-step approach that emphasizes building a healthy culture where people want to work.

    31 分钟

  4. 11月25日

    I Have to Figure This Sh*t Out

    This week, in Episode 272, Liz Picarazzi and Jaci Russo compare notes with Ted Wolf on their very different journeys to integrate generative AI into their businesses. For Liz, it’s been frustrating. She resisted AI at first—but while she’s ready to go now, her COO, who also happens to be her husband, still isn’t there. That’s one reason Liz says she feels as though she’s been spinning her wheels. Jaci’s path couldn’t have been more different. She jumped in more than two years ago, took every course she could find, and now has custom GPTs talking to custom GPTs talking to custom GPTs. The AI tool she built delivers 10 fresh, fully vetted prospects to her inbox every morning. “It will find the person in charge of marketing,” she says. “It will find their LinkedIn profile. It will find the company website. It will find their competitors.” And it has already produced two new clients. Plus: As this especially challenging year winds down, Liz, Jaci, and Ted reflect on where their businesses hit expectations and where they fell short. Jaci notes a sales hire that failed. “I would have liked to have not spent the money on that person and had this epiphany without the pain,” she says, “but I think those two things just go hand in hand.” Liz cites her $400,000 tariff bill: “It really hurts, and it makes me angry,” she tells us. “But in terms of revenue, we’re doing well, I gotta admit. Thank God for New York City rats and trash.”

    49 分钟

  5. 11月21日

    Dashboard: Want More Domestic Manufacturing? Think Small

    That’s the conclusion of Ilana Preuss, who is founder and CEO of Recast City and who believes that the way to bring back America’s Main Streets, downtowns, and local economies is through small-scale manufacturing. While traditional economic development focuses on what Preuss calls big-game hunting--recruiting big, established companies--she favors looking for ways to support even the smallest of businesses. How can a community do that? Step one, she says, is to find local manufacturers, talk to them, and find out what they need. Go figure!

    33 分钟

  6. 11月18日

    She Still Packs Every Order as if It’s a Gift

    This week, in Episode 271, we welcome another new voice to the podcast: Channon Kennedy, who takes us inside the side hustle that’s become her second full-time job. Channon is the inventor and patent holder of the Morgan Square, a clever measuring tool—here’s a demonstration—that’s racking up awards, expanding its distribution, and carving out space for a woman founder in a traditionally male-dominated industry. This is a true bootstrap story. Channon’s numbers are modest enough that she still does most of her own fulfillment at night after her day job as a banker—and she loves it. “Every time I get an order,” she says, “I feel like I'm wrapping a Christmas present. I'm just so excited that somebody wants something that I've created.” Plus: Paul Downs checks in with an update. After posting his best year ever in 2024, he was blindsided when sales suddenly stalled earlier this year, forcing him to lay off a third of his employees. Sales have since rebounded, but now he’s staring at a backlog and a different dilemma: Does he hire aggressively to meet the higher demand—or play it safe until he sees how 2026 begins?

    45 分钟

  7. 11月14日

    Dashboard: Seeing Past the Workslop and Hallucinations

    Yes, says Gene Marks, it’s easy to make fun of all of the ways in which AI chatbots can fail (don’t even think about asking them to create an image of a Yorkshire Terrier hitting a homerun), but that’s no excuse to sit on the sidelines. Get the paid version. Get some training. Get your employees some training. And get to work. On what? Gene gives some examples of his favorite use cases.

    30 分钟

  8. 11月11日

    Welcome to Employee Ownership! (Without the Hype)

    This week, in Episode 270, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings, a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally change the risk profile of a business. And perhaps the most under-discussed challenge of all: not all employees embrace employee ownership. Some see it as little more than a glorified retirement plan. And here’s the thing: an ESOP can be a far riskier retirement plan than many understand. They differ from 401(k)s in that there's no regulation requiring an ESOP to sequester its employees’ retirement funds. If the company fails—and like all businesses, ESOPs do fail—those nest eggs can vanish. Kris and Justin explain how they’ve addressed these issues and what they might do differently if they were starting over. They also emphasize an important point: Not all ESOPs are created equal. “If you’ve seen one ESOP,” Justin likes to say, “you’ve seen one ESOP.”

    46 分钟
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关于

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.

信息

  • 创作者
    21 Hats
  • 活跃年份
    2020年 - 2025年
  • 单集
    487
  • 分级
    儿童适宜
  • 版权
    © Copyright 21 Hats
  • 节目网站
    21 Hats Podcast

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