21 Hats

21 Hats is a digital community designed for entrepreneurs. The name reflects the many roles that business owners take on while growing their ventures. Not all of these roles fit perfectly, and that’s where we come in. If you're feeling uncertain or need direction, the 21 Hats community is available to support you.

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Articles

Maybe Earnouts Aren’t as Bad as You Think

1 week ago | 21hats.com | Loren Feldman

Introduction:This week, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model.
Big Changes Are Coming to the SBA. That’s a Good Thing

2 weeks ago | 21hats.com | Loren Feldman

Yes, getting an SBA loan will get more difficult, but the long-term viability of the agency will be protected. By Ami KassarThe Trump Administration has moved quickly to make changes to the Small Business Administration. As I have written before and as I testified before Congress, significant changes were made to the SBA during the Biden Administration, which strove to open up SBA lending as much as possible.
Dear ChatGPT: What Are My Blind Spots?

2 weeks ago | 21hats.com | Loren Feldman

Introduction:This week, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback?
An Entrepreneurial Community Built on Grit

3 weeks ago | 21hats.com | Loren Feldman

Late one night, I started a WhatsApp group for Entrepreneurs’ Organization members having a tough time. Slowly and steadily, an engaged community has taken hold. By Ami KassarAbout eight months ago, I was getting frustrated. We were getting more and more calls at MultiFunding from business owners and entrepreneurs who we couldn’t help with financing because their profitability and cash flow were upside down.
I’d Love to Manufacture in the U.S.

3 weeks ago | 21hats.com | Loren Feldman

Introduction:This week, Liz Picarazzi tells Sarah Segal that she’s taking another pass at finding a domestic fabricator. Maybe it’s wishful thinking, Liz says, but she’s hoping that now that her business is more established, she just might find an American factory that wants to partner with a growing business and would be eager to help her re-shore her manufacturing.
The Hidden Cost of Bad Hiring

1 month ago | 21hats.com | Loren Feldman

Introduction:This week, Jay Goltz and Lena McGuire talk about an expense a lot of business owners may not even realize they’re paying. When former employees collect unemployment, they get a check from the government, but then their former employer gets docked. It can add up to real money, and that’s likely to become a bigger issue if the economy deteriorates. Of course, as Jay and Lena discuss, one way to keep your unemployment insurance as low as possible is to do a better job hiring.
The Economic World Is Shifting Once Again

1 month ago | 21hats.com | Loren Feldman

Trade wars may be beyond the control of business owners, but there are things owners can control. By Ami KassarThe speed of change over the past few months has been hard to comprehend. The many changes will have different impacts on different businesses. As always, there will be some winners and some losers. Meanwhile, many entrepreneurs are lying awake at night trying to figure out what it all means and what, if anything, they can do: Should they try to change suppliers?
The Tariff Bill Arrives

1 month ago | 21hats.com | Loren Feldman

Introduction:This week, in a conversation recorded on March 27—shortly before Liberation Day, the day Donald Trump announced his so-called reciprocal tariffs—Liz Picarazzi told Shawn Busse and Jaci Russo what it was like to get her most recent tariff bill for a shipment of trash enclosures from China. “I knew what it was going to be, because I had calculated it,” she says, “but to actually see it on paper was terrifying.” And of course it’s only going to get worse now.
‘At 5 O’Clock, I’m Going to Send Everybody an Email’

1 month ago | 21hats.com | Loren Feldman

Introduction:This week, Paul Downs tells Jaci Russo and Sarah Segal about laying off a third of his workforce. “Here’s the problem in a nutshell,” he says. “Last year, January to March, we sold $1.356 million. This year, January to March: $680,000. March is on track to be the worst month I’ve had since I started taking records.” Paul also tells the owners that he used to have a rainy-day fund for such occasions, but he used it to renovate his house.
Launching Lyx: ‘Gatorade for Dogs’

1 month ago | 21hats.com | Loren Feldman

Introduction:In this week’s bonus episode, special guest Dylan Jones shares his entrepreneurial journey, which includes serving in the Air Force, a Master’s degree in business analytics, a failed software business, and a brand new consumer packaged goods startup that draws on his knowledge of military working dogs—most importantly that it can be a challenge to keep military dogs (and pets) hydrated.