21 Hats Podcast
21 Hats
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.
Episodes
Mentioned books
Mar 10, 2020 • 44min
Maybe This Isn’t the Right Job for You
Nobody goes into business because they think they're going to be really good at firing people. When you read books or magazine profiles of business leaders, you rarely hear anyone say, “You know, the one thing I've really mastered is knowing when and how to fire people.” And yet it’s something that every entrepreneur has to deal with. Even at the most successful businesses, some employees are not going to make it. In this episode, regulars Karen, Jay, and Dana answer the question: how many people have you had to fire or lay off? Plus: What do you do when you find you have venture-backed competition?
Mar 3, 2020 • 1h 2min
Special Episode, Part 2: We Want to Talk to You About the Bread
In Part 2 of our special taping in front of a live audience at Blink UX’s headquarters in Seattle, Brian Canlis talks about how he and his brother took over the family restaurant and what happened when they decided to modernize its operation: “We did lose 10,000 guests that year. And we lost money for the first time as a company ever that year. And we got three negative reviews in the paper. And we were averaging about a dozen complaint letters a week about how much they thought Mark and I were destroying a family legacy. That was a low moment.” Regulars Karen Clark Cole, Jay Goltz, Dana White, and Laura Zander join the conversation as well. Plus: how Canlis gets employees to work harder for less money.
Mar 2, 2020 • 8min
Mini Episode: The 21 Hats Business Owners Make Coronavirus Contingency Plans
In a quick update, Karen, Jay, and Dana talk about how the coronavirus pandemic has already affected their businesses and how they are planning for the future.
Feb 25, 2020 • 44min
Special Episode, Part 1: All You Have to Do Is Be Better
In this special taping in front of a live audience at Blink UX’s headquarters in Seattle, Karen, Jay, Dana, and Laura talk about the risks of fast growth and why they haven’t taken investment capital. “I was so focused on growing that I kind of blew it up. I blew the whole business up by hiring people who we weren't ready to hire for. We were probably doing $5, $6, $7 million dollars in sales. I didn't need a $90,000 a year social media person 10 years ago. I just didn't, but I listened to what other people were telling me.” Plus: Dealing with competition.
Feb 18, 2020 • 55min
We’re at the Edge Right Now
Karen, William, and Laura discuss taking investment capital, dealing with stress, and why Karen’s going on sabbatical: “I just thought, ‘Okay, okay, I'll go.’ Then of course, I'm worried, like, ‘What if everything goes better without me?’” Plus: how are you managing health insurance costs?
Feb 11, 2020 • 35min
Does Culture Really Eat Strategy for Lunch?
Jay, William, and Laura discuss whether a great culture produces a successful business or whether a successful business produces a great culture. Do you think of your employees as family? Do you have anyone working for you whom, if you had it to do over, you wouldn’t hire? Plus: do you manage your Glassdoor page?
Feb 4, 2020 • 46min
What Do I Have to Lose, Right?
Jay, Dana, and Laura talk about risking it all, figuring out digital marketing, and connecting with your target audience: “Right now, my market is predominantly African American, but we have a lot of redheads. We have a lot of women of Indian and Middle Eastern descent.” Plus: how do you know if franchising makes sense for your business?
Jan 28, 2020 • 37min
I’m Trying to Survive in Retail
Jay, Karen, and Laura talk about competing on the internet, buying a supplier, and whether to take venture capital: “Who needs to answer to somebody if you don't have to?” Plus: after the Domino’s decision, what happens if your website isn’t disability compliant?
Jan 8, 2020 • 1h 29min
Special Episode: He Patted My Hand and Told Me I Didn’t Know Anything About Business
Loren and Karen talk with four of EY’s Entrepreneurial Winning Women about opening the books, bootstrapping a tech company, selling a business for more than $100 million, competing with Amazon, hiring hard-to-get talent, and pitching investors: “I've always said, ‘I'd rather be 75 percent of a watermelon than 100 percent of a grape.’” Plus: how much of your life do you have to sacrifice to be successful?
Jan 8, 2020 • 44min
At Vanderbloemen Search, Everyone Blogs. Everyone? Everyone.
Jay, Karen, and William talk about pricing, custom manufacturing, and content marketing: “There have been people who would have been very good at a job, but they aren't willing to or able to put together content, and that just doesn't work for us.” Plus: the SEO value of an unusual last name.
