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

At 21 Hats, we’re not going to tell you how to run your business. But we are going to publish news articles, Q&As, webinars, and podcasts that feature business owners speaking frankly about what it takes to build a business.

By Loren Feldman

Our mission is to build a community of business owners who compare notes, share their wins and losses, and learn from each other.

Here’s what we offer:

  • A daily email newsletter that Inc. magazine called the best newsletter for business owners. It combines our own articles, interviews, and analyses with the most important news of the day for owners. We scour the web so you don’t have to — and deliver the highlights right to your inbox first thing every morning.
  • A weekly podcast that has been tracking the journeys of a group of business owners since before the crisis. Every week we moderate a conversation among three of the owners, who discuss what’s working, what’s not, and how they see the challenges all owners confront.
  • A monthly mastermind session for Founding Members. This forum meets the second Wednesday of every month at 12 ET over Zoom, where we compare notes, make connections, and discuss the kinds of issues you read about in this newsletter.


  • In May, 21 Hats held its first in-person event in Chicago. Limited to 20 business owners/CEOs, the event started with dinner on Wednesday, May 17, and ran through lunch on Friday, May 19. It featured lots of opportunities to compare notes with other owners on similar journeys, as well as a chance to interact with five of the 21 Hats Podcast regulars, ​including ​Paul Downs, Jay Goltz, Liz Picarazzi, Dana White, and Sarah Segal. We also taped an episode of the 21 Hats Podcast, toured Jay Goltz’s retail and manufacturing operations, took an architectural cruise on the Chicago River, and made connections that will last a lifetime. We plan to do two similar events in different cities in 2024.

Here’s what people are saying about us:

“I absolutely love 21 Hats. The morning newsletter is phenomenal. I consume news for a living and nearly every day you post a story or an angle to a business issue I wasn’t aware of. This past year the podcast has been a real lifeline for me. As a small business owner I went through such an extreme range of emotions dealing with the pandemic, listening to your show and relating to and identifying with nearly everything Dana, Paul, Jay and the rest talked about made me feel so much better. Just wanted to say thank you. I introduced my Vistage group to the podcast and everyone was floored.” — Dan Kahn, Kahn Media

“The 21 Hats Podcast has been a master class in small business decision making. I highly recommend it to anyone running or considering a small business.” -— Harry Elston, CEO, Midwest Chemical Safety

“This is gold! Loren Feldman, you’re providing fantastic resources for business owners to learn and grow. Subscribing to the 21 Hats newsletter is like taking a masterclass in entrepreneurship.” — Nikki Barua, Beyond Barriers

“I’m addicted to The 21 Hats Podcast. I almost wish it was a daily show.” — Jim Kalb, CEO, Triad Components Group

“As a small business owner, I’m devouring The 21 Hats Morning Report, which is chock-full of resources and helpful news.” — Jean Chatzky, CEO, Hermoney

“Damn it, Loren. I’m really busy and I always want to read your report.” — Rob Levin, CEO, RSL Media

“If you’re a business owner and haven’t subscribed to the Morning Report email newsletter, what are you waiting for?” — Charles Gaudet, CEO, Predictable Profits

“Listening to The 21Hats Podcast is a therapeutic ritual while cooking dinner on Wednesday nights. It’s the only podcast I listen to religiously.” — Liz Picarazzi, Citibin

“I don’t feel I have much time to read—yes, personal challenge—and yet taking a few minutes to read your newsletter grounds me in what is and what’s possible. Thanks for assembling solid, pertinent information that helps me feel more confident as a leader.” — Chris Hutchinson, CEO, Trebuchet Group

“How do I start my morning? With a cup of coffee and the 21 Hats Morning Report, of course.” — Barbara Taylor, Allan Taylor & Co.

“I was like, had I not read the Morning Report, how would we have found this out otherwise?” — William Vanderbloemen, CEO Vanderbloemen Search Group

“Loren has been on the cutting edge of small business reporting for 20 years — with a tremendous breadth of knowledge and insights. I have really benefited from his Morning Report and podcasts this year.” — John Arensmeyer, CEO, Small Business Majority

“One of only three newsletters that I read religiously. Always worth reading.” — Steve Krull, CEO, Befoundonline

Here’s how we got here:

For almost 20 years, I’ve been part of the senior editorial staff covering entrepreneurship at Inc.The New York Times, and Forbes. At each of those publications, I learned important lessons and I’m now bringing them together at 21 Hats. One early lesson, for example, came to me years ago when I was conducting a focus group of business owners. We asked one what he hoped to get out of the business publications he read. “I’ll tell you what I don’t want,” the owner responded. “I don’t want to be told how to run my business by a 23-year-old journalist working for a money-losing publication.”

Point taken! Our goal at 21 Hats is to offer owners and entrepreneurs the insights, lessons, and stories that come from the people who live them. In other words, at 21 Hats, we’re not going to tell you how to run your business. But we are going to publish news articles, Q&As, webinars, and podcasts that feature a range of voices speaking frankly about what it takes to build a business—and what to do when success is elusive. That means no five-easy-steps-to-better-SEO or 12-businesses-you-can-start-in-your pajamas articles – but lots of engagement among actual owners.

Throughout my career, I’ve been fortunate to work with some very smart journalists and entrepreneurs. At Inc., I edited Norm Brodsky’s column when it was nominated for two National Magazine awards, including one for a remarkably forthright series on his efforts to sell his business. I also worked with author Bo Burlingham, editing pieces like his cover story about a business owner, Jay Goltz, who learned the hard way that the hype that surrounds business growth can be misleading. At The Times, where I created the You’re the Boss blog, Jay became one of our regular contributors. Another, Paul Downs, started blogging when he thought his company was headed for bankruptcy and then took us along for the ride as he turned his business around. He kept writing and sharing his experiences even when he made a big mistake on his pay-per-click advertising campaign that again threatened his business’s survival.

At Forbes, Bo and I created the annual list of Forbes Small Giants, businesses that are more focused on being great than being big. The companies we picked had to be closely held, leaders in their industry, leaders in their community, and profitable. We also looked for businesses that had blazed a fresh trail. For example, we picked Zulu Alpha Kilo, which figured out that it could build a successful advertising business without playing by the industry’s standard rules of giving away its best work trying to win accounts in beauty contests. We picked Missouri Star, which was started by a family that went from food stamps to a $40 million-a-year quilting business. And we picked SRC Holdings, which pioneered open-book management, adopted employee ownership, and managed to turn factory workers into millionaires while topping $600 million in annual revenue.

My hope is that 21 Hats will offer the best of all of the above and more. Don’t want to miss anything? Easy. Just subscribe to the 21 Hats Morning Report. Got a question, suggestion, or concern? You can always email me: loren@21hats.com. You can also follow me on Twitter or connect on LinkedIn. — Loren Feldman, 21 Hats, Founder, Editor-in-Chief

We would love to hear from you
Ask us anything
Or suggest a topic for a podcast, an interview or a blog post