21 Hats Podcast

Lena McGuire, CEO of Spoka Kitchen and Bath, shares insights on the benefits of buying commercial real estate for her growing business. Jay Goltz, a retail expert, emphasizes the long-term value of property appreciating beyond business worth. Liz Picarazzi discusses navigating supply-chain challenges and tariffs while showcasing an AI tool that streamlines her sales process. They delve into strategic considerations like financing, location over price, and adapting to market uncertainties to ensure longevity in their respective industries.

Greg Shugar, owner of Beau Ties and co-founder of The Tie Bar, dives deep into how tariffs threaten U.S. manufacturers. He explains the irony of needing imported silk while being a domestic producer. A possible 100% tariff looms large, complicating his business planning and profitability. Shugar discusses stockpiling strategies, the challenges of small business lobbying in Washington, and the mixed reception from lawmakers. He passionately argues against offshoring production, emphasizing the impact on brand identity and U.S. jobs.

This week, in episode 267, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boatload of cash.” Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money? Also, when valued employees get an offer, do you counter-offer? And if they leave, do you tell them they can always come back?

Join Jay Goltz, a seasoned entrepreneur and CEO of The Goltz Group, David C. Barnett, a business broker and advisor from Canada, and Kate Morgan, CEO of Boston Human Capital Partners. They dive into the struggle of crafting employee career paths while staying true to company goals. Jay highlights the importance of letting employees experiment, while David warns that businesses risk obsolescence without evolution. Kate shares her experiences of stress during rapid growth, touching on employee retention and the art of thorough onboarding.

Ted Wolf, experienced entrepreneur and co-founder of GuideWise, shares insightful AI strategies for businesses of all sizes. He discusses the common pitfalls of AI pilots and emphasizes the importance of partnership and governance. Ted offers practical steps for small businesses to start their AI journey, including using ChatGPT for immediate SWOT analyses against competitors. He highlights the vital role of training and trust-building to overcome employee resistance while cautioning against sharing sensitive data on public platforms.

This week, in episode 264, David C. Barnett and Jennifer Kerhin say they’re already making plans for next year: adjusting pricing, conducting employee reviews, and setting budgets. In the past, Jennifer has chosen to restrain growth to give her employees and her processes a chance to catch up. But this coming year? She says she’s ready to “unleash the hounds.” And for the first time, she’s planning to budget for profit first and then force her expenses to fit her margins. Unlike Jennifer, who conducts employee reviews throughout the year, David saves his evaluations for the end of the year. As he looks forward, he’s trying to figure out what the economy means for his business. He’s seeing more companies in distress, but also more opportunities to help people with severance packages who decide to buy businesses. Plus: David and Jennifer share how they’ve each been experimenting with ChatGPT of late.

This week, Kurt Wilkin discusses what he’s learned about selling businesses and how he’s thinking about what he might do next. An entrepreneur, an investor, a mentor, and a former business owner who recently sold a recruiting firm, Wilkin tells us why his acquisition of the firm didn't work out the way he hoped and how he managed to turn it around and sell it. Part of the problem, Kurt says, was that he jumped back into the game too quickly after selling his previous business. It’s a mistake he’s not going to repeat this time.

This week, in episode 264, Mel Gravely brings closure to a story he’s been sharing in pieces over the past year. You may recall that he bought a facilities maintenance company a couple years ago that he was convinced he could scale—only to discover that it was hemorrhaging money. Mel dug in, diagnosed the problem, fixed it, bought out his partners, turned the company profitable—and then decided to shut it down. Why close a business that’s making money? Mel explains the surprising answer, along with three lessons he says he learned. He also joins Jay Goltz in a candid discussion of the painful flipside of hiring: When, and how, does it make sense to lay off employees? As Jay points out, it’s far easier to find advice about adding people than about letting them go, even though it’s a calculation many owners are facing today. Plus: A would-be entrepreneur preparing to launch a business with two friends admits he’s feeling scared. He wants to know whether that fear ever goes away. Mel and Jay think he’s asking the wrong question.

Cameron Madill, an entrepreneur and former CEO of Pixelspoke, shares insights from his research on married entrepreneurial couples through the Happy Couples Project. He discusses the fine line between healthy and unhealthy passion for work, revealing its significant impact on relationships. Cameron also highlights common conflicts couples face, like work-home boundaries and financial pressures, while offering strategies to balance business and marriage. Listeners will find practical advice and surprising findings from his research, making this a valuable conversation for entrepreneurial couples.

This week, in episode 263, we bring you another 21 Hats Brainstorm. Elan Daniel, who started a small-batch hummus business inspired by a memorable experience in Israel, is trying to figure out his best path to long-term viability. So far, he’s been selling at farmers markets and direct to consumers, making all of the hummus and all of the deliveries himself. Since February, his sales have been growing between 5 and 10 percent a week, but his growth is constrained by his refusal to use preservatives, which adds flavor but limits the product’s shelf life. So how should he proceed: Should he sell to speciality markets and restaurants? Should he try to sell to Whole Foods? Should he open his own hummus restaurant, or hummusiya? Should he try to introduce his hummus to the uninitiated or should he focus on connoisseurs? To help Elan think through his options, we convened a panel of 21 Hats Brainstormers and recorded this podcast episode. It’s brought to you by New Bridge Studios, which helps companies, creators, and causes connect their story to the bottom line. And by the way, if you have a challenge you’d like to put before a panel of business owners in our next Brainstorm, shoot me an email: loren@21hats.com.