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Ami Kassar on how to avoid paralysis.
Embracing the Uncomfortable

Pushing your business to the next level often involves difficult choices. Do you know everything you need to know?

About 21 Hats: What We Do. What People Say. How We Got Here

Have you read our testimonials? At 21 Hats, don't tell you how to run your business. But we do publish news articles, Q&As, webinars, podcasts about what it takes to build a business.

SVB Will Not Crash the Banking System

But it might bridge the divide between Main Street and Silicon Valley.

What Would You Do: Sell Equity? Or Bet the House?

It is possible to get an SBA loan for a projection-based startup. But you need a sound business plan, and you have to be prepared to kiss a lot of frogs and for the process to take as long as nine months.

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Episode 154: ‘What Doesn’t Keep Me Up at Night?’
‘What Doesn’t Keep Me Up at Night?’

This week, we did something different. We recorded this session in Chicago at our very first 21 Hats in-person event. In May, some 20 impressive entrepreneurs from around the country, from different industries, with businesses of different sizes and stages, gathered to talk shop for three days. The last thing we did was to record this episode in which we gave the participants the opportunity to ask the podcast regulars anything they wanted. Those regulars included Jay Goltz, Sarah Segal, and Dana White, and the questions addressed everything from hiring to motivating to delegating to pricing to coping with stress to what they wished they’d figured out sooner and to what still keeps them up at night. And when there were no more questions, I asked those who attended the Chicago event what I could have done to make it better. That I would invite criticism in a conversation being recorded for a podcast audience, took some of the participants by surprise. But, as you’ll hear, it worked out pretty much the way I hoped.

Top Podcast episodes
Should You Be in a Business Group?

This week, Sarah Segal, Jay Goltz, and special guest Leo Bottary have a hype-free conversation about why peer-advisory groups like Vistage, YPO, and EO can be life-changing for business owners and why they’re not for everyone. Sarah has been wondering if they’re for her. Jay, who’s been in six different peer groups, says it can be worth the price of admission just to see how other owners run their businesses—but there are reasons he keeps leaving the groups he joins. And Leo is a former Vistage employee who has written multiple books on peer groups and has built a related consulting practice. Surprisingly few business owners belong to a peer group. Are they missing out? All three of my guests suggest questions to consider before deciding for yourself.

Successful Raise, Fast Growth, Mental Health Issues

This week, Hans Schrei tells Shawn Busse why this has been a difficult year at Wunderkeks—despite many outward signs of success. It has to do with buying into the need to raise money and shoot the moon. It has to do with accepting the accolades that come with entrepreneurial achievement and then questioning your own self-worth when those accolades stop coming. It’s what Hans calls, “the miracle worker complex.” Hans and Shawn also discuss what it means to rely upon a sales platform like Amazon. Do you own the customer or does Amazon? And Shawn explains the biggest takeaway from his most recent Vistage meeting.

Bonus Episode: Seth Goldman Brews Another Ice Tea

This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the sale, what it was like being a Coke employee, what he’s been doing since leaving, how the beverage industry has evolved, and whether he’ll end up selling this business to Coke, too.

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Never miss a 21 Hats Podcast episode
The Changing Face of the Yarn Industry

For many, knitting may still conjure an image of a grandmother in a rocking chair, her cats sleeping and her doilies taking shape. In recent years, however, the quiet industry of tiny neighborhood yarn shops scattered across the U.S. has become an unlikely cultural battleground. It’s been divided by charges of racism and cultural appropriation that have erupted in a series of social media firestorms, prompting some owners to close, sell, or rebrand their businesses. It may seem surprising that such a quiet pursuit could produce so much conflict, but it’s really not all that different from the fissures afflicting the country as a whole. In this conversation, we meet three women who were not content to stick to their knitting: Adella Colvin, whose business, LolaBean Yarn Co., is a prominent independent dyer based in Grovetown, Ga.; Gaye “GG” Glasspie, a leading yarn industry influencer whose signature color is orange and who is based in Clifton, N.J.; and Felicia Eve, who owns String Thing Studio in Brooklyn, N.Y., one of the few Black-owned yarn shops in the country. The video offers our entire conversation. You can also listen to a slightly edited 21 Hats Podcast version of the conversation wherever you get podcasts.

What’s Wrong With Small Business Marketing?

It’s not always about marketing. Sometimes, the real issues go deeper. Sometimes, before you can figure out how to sell, you have to figure out who you are.

What’s in It for the Owner? A Skeptical Conversation about ESOPs

Both Jeff Taylor and Jim Kalb run companies with employee stock ownership plans. Jay Goltz is thinking about implementing one — but he’s got questions, such as: Where does the money to buy the company come from?

A Business Owner Dares to Start a Real Conversation About Race

White owners often ask Mel Gravely, CEO of TriVersity Construction, what they can do to help. He’s got an answer for them, which he offers in this interview and in his challenging new book, ‘Dear White Friend.’

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