My Vision for 21 Hats

The time has come. With much excitement and more than a little trepidation, I have an announcement to make.

Those of you who have been reading the Morning Report and listening to The 21 Hats Podcast know that I’ve been giving much thought to how I can turn 21 Hats into a sustainable business that actually generates revenue. After weighing lots of smart advice from many of you and after a little too much foot-dragging, I’m ready to proceed.

My vision is to build 21 Hats into a community where real business owners—those who bootstrap, who borrow against their homes, who create something out of nothing, and who nonetheless are all-too-often ignored by mainstream publications—can compare notes, share their wins and losses, and learn from each other as we proceed on our journeys. Along with the Morning Report, the fully realized 21 Hats community that I envision will feature multiple podcasts, sharp analysis, spirited advocacy, topic-based online forums, mastermind groups, regional events, an annual summit, and annual awards for the best privately owned businesses—the Top Hat Awards, complete with a 21 Hat Salute.

To make that vision a reality, I need the wisdom and energy of the 21 Hats community. Today, I’m here to share my monetization plan and ask for your support.

Step one: Attract sponsors. Happily, this is underway. I want to feature one sponsor each week on the podcast and five in the Morning Report, one for each day. If you or someone you know might be interested, please let me know. That said, my goal is for 21 Hats to be supported by its sponsors but driven by its readers, the people who derive value from it. That’s Step Two.

Step two: As of today, I am asking you to join the cause of giving real businesses the attention and support they deserve. Please select one of the following subscription options, Paid Subscriber or Founding Member.


Here’s what you get:

  • The 21 Hats Morning Report, which saves you time by scouring the web for the most important news of the day for business owners and delivering highlights straight to your inbox first thing every morning.

  • The 21 Hats Podcast, which has been tracking the experiences of eight remarkably transparent business owners since before the pandemic in weekly conversations. I’m not sure you can find such an honest and open peer-group discussion anywhere else.

  • The 21 Hats Conversation, a monthly webinar featuring insightful, news-making entrepreneurs. You can attend the webinars live and participate, or you can watch/listen later on demand.

  • You also get to participate in our ever-expanding community features, such as Jay’s Tips, contributor pieces, crowdsourced Q&As, and subscriber Spotlights.

  • Most important, you get to be part of a group that understands why you do what you do.

Here’s what a paid subscription costs: $14 a month or $140 a year.


Here’s what you get:

  • All of the same great features that Paid Subscribers get.

  • Plus the opportunity to be part of a monthly mastermind group where we get to know each other, share experiences, plot the future of 21 Hats, and engage with guest speakers. I’ve been sounding out members of the 21 Hats community, and I know this will be an impressive group. Enrollment will be limited.

Here’s what being a Founding Member costs: $480 a year, which is less than 3 percent of a Vistage membership. I’m just saying!

Full Disclosure: This is a test. I’m not going to put up a paywall for now because I want new readers and listeners to be able to try out the Morning Report and The 21 Hats Podcast for free. I want the community to keep growing, and I want us to be in a position to support and engage with as many owners as possible. The more people we bring into the conversation, the more we will all get out of it. But again, this is a test. If I don’t get enough voluntary signups, I will acknowledge my naivete and put up a paywall.

One way or another, I’m confident this will work: At Inc, Forbes, and The New York Times, I tried out versions of 21 Hats for almost 21 years. Now I’m bringing together all I’ve learned. I know there is an unmet need for genuine, street-smart, hype-free coverage of entrepreneurs and their privately owned businesses. And the emails I get every week reinforce this. For example:

“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

Let’s do this. I’m committed to making 21 Hats an increasingly valuable resource for you and your fellow entrepreneurs. And I’m confident that, thanks to the community we are creating, no matter which subscription option you choose, the return on your (tax deductible!) investment will be epic.

Thanks for reading this, and thanks for your consideration.

Loren Feldman