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

‘Mom, I Am Not Taking the LSAT’

5 days ago | 21hats.com | Loren Feldman

Introduction:This week, in Episode 249, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses.
How Big Do I Want My Business to Be?

1 week ago | 21hats.com | Loren Feldman

Introduction:This week, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership.
We Get Paid to Judge People

2 weeks ago | 21hats.com | Loren Feldman

Introduction:This week, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices.
I Recently Decided to Change My Business Support Group - 21 Hats

3 weeks ago | 21hats.com | Loren Feldman

I couldn’t sleep the night before I made the switch, but I’m confident it was the right decision. By Ami KassarI am a huge proponent of peer groups. Over the last decade, I have been in two different Vistage groups and am now in my second Entrepreneurs’ Organization forum. I found my home when I joined EO seven years ago, and next month I will wrap up my term as president of the EO Philadelphia chapter. Recently, though, I decided to switch forums after being in one group for more than six years.
‘I’ll Tax Your Seat’

3 weeks ago | 21hats.com | Loren Feldman

Introduction:This week, we meet special guest Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer.
Maybe Earnouts Aren’t as Bad as You Think

1 month 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

1 month 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?

1 month 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

1 month 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.

1 month 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.