Podcast
21 Hats Podcast
Hosted by 21 Hats · EN
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.
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Episodes
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‘I’m Skeptical AI Is Going to Help Us’
Jun 200:48:31Tap to summarizeThis week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on something AI still lacks: real world experience. While AI can generate impressive images and concepts, he argues that it has no understanding of manufacturing constraints, material properties, production processes, or the capabilities of the people and machines that have to bring an idea to life. “An image of a thing that looks cool is not a design,” Paul says. “A design is a set of information that's informed by intelligence and experience.”Ted Wolf, who helps companies implement AI, agrees that AI can't replace the collective creativity and judgment of skilled people. But he believes Paul may be looking at the problem too broadly. Instead of asking whether AI can design and build custom furniture, Ted suggests breaking the workflow into smaller pieces and experimenting with targeted applications. “You know your business better than anybody else,” Ted tells Paul. “But don't look at the big picture and think that's the entire thing. There are many small pieces that people can start doing today.”The result is a thoughtful debate about one of the biggest questions facing small business owners: Is AI going to change everything, or are there businesses where human expertise will remain irreplaceable?Plus: Channon Kennedy shares what she learned from participating in a Goldman Sachs program for Black women entrepreneurs. And the owners discuss what debt can—and cannot—do for a business: “Funding does not fix a broken business model. It makes it die faster.”
Transcribe →Dashboard: Uber for Landscapers
May 2900:32:51Tap to summarizeWhen Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping business that grew to $10 million in annual revenue before eventually selling it. But even while running that business, Clayton had been thinking about another problem: why was it still so hard for homeowners to hire a reliable lawn service?Despite having no background in technology, Clayton bootstrapped a platform called GreenPal, which connects homeowners with lawn-care specialists—essentially an Uber for landscapers. Today, still entirely self-funded by Clayton and his partners, GreenPal serves more than 300,000 users nationwide. In our conversation, Clayton talks about the operational mistakes that trip up many small businesses, how GreenPal uses both incentives and penalties to improve landscaper performance, and how the company is using AI to identify contractors whose businesses may be headed for trouble.
Transcribe →I’m Not a Real CEO
May 9, 2023Tap to summarizeThis week, in episode 152, Jay Goltz, Liz Picarazzi, and Sarah Segal talk about the inherent conflicts between being an entrepreneur and being a CEO—and the different skill-sets each role requires. Does it make sense for the same person to do both jobs? Is being CEO even a full-time job? And when does it make sense to replace yourself as CEO? Liz says she’s thought about it. Jay, not so much: “Could I have found somebody 10, 15, 20 years ago who was a better manager? Sure. But it just wasn't worth it.” Why not? “It's gonna cost you $250,000 a year,” Jay says. “Is it worth paying that?” Plus: Liz and Sarah talk about positioning a company to be acquired. And Sarah proposes a PR campaign for Liz’s package bins right on the spot.
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