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

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 recently said is 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 ten 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. See recent examples.

  • Frequent webinars that introduce business owners to new voices and concepts. You can attend live and bring your own questions, watch the video at your convenience, or scan an abridged transcript. For example, here’s a recent conversation with two owners who share a smart approach to marketing. Here’s another conversation with two CEOs who run ESOP companies and a third who is interested in going ESOP but has lots of questions.

  • The opportunity to share insights with other smart owners. Here’s a recent thread where we asked 21 Hats subscribers what they would ask a world-class board of experienced entrepreneurs if they could ask just one question. Here’s another thread where we asked subscribers to tell us what they do and how it’s going. We expect to add additional opportunities for 21 Hats to engage with each other – maybe even in person! – in the near future.

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.

-- Loren Feldman, 21 Hats, Founder, Editor-in-Chief

Subscribe to The 21 Hats Morning Report

We scour the web to highlight the most important news of the day for business owners. Handcrafted daily by entrepreneurs for entrepreneurs.


Loren Feldman
For 20 years, I've been covering entrepreneurs for Inc., Forbes, and The New York Times. Now I'm building the 21 Hats community for business owners.