SBM 21 - Loren Feldman - New Media vs Old Media

New Media vs Old Media.

In the last edition, we learned all about Julie Lopez and her trauma-informed therapy practice that broke the mold.

In this edition, we’re shifting gears to explore the journey of a journalist turned entrepreneur. 

Fast Facts:

  • The journalism industry has faced significant challenges due to the rise of digital media and declining print revenue 

  • Newspaper revenue has declined sharply, from $46.2 billion in 2002 to only $9.8 billion in 2022

  • Large newspapers have seen a layoff rate of 11% in recent years, and online publishers have reached 20% 

  • At the same time, new forms of media have thrived including newsletters, podcasts, social media and others i.e. substack creators have grown from 6,000 in 2020 to over 1 million as of 2022 

  • But only a fraction of these creators earn enough to make a living 

  • Niche media businesses that rely on other revenue streams are emerging as a viable model, focusing on specific industries or topics and creating engaged communities



Loren Feldman is a veteran journalist who has worked at publications such as Inc. Magazine, The New York Times and Forbes. 

In 2018, Loren launched 21 Hats, a media platform aimed at providing resources and community for small business owners and entrepreneurs. 

The Story:

Loren Feldman’s journey from journalism to entrepreneurship is a tale of adaptation, resilience, and seizing opportunities in the face of industry upheaval. 

With a background in economics and a passion for storytelling, Loren initially set his sights on becoming a sports writer. However, he quickly realized that the path to career growth might be faster in business journalism.

Over the years, Loren honed his craft at prestigious publications like Inc. Magazine, where he worked closely with renowned author Bo Burlingham on stories about purpose-driven businesses. 

This experience laid the foundation for his deep understanding of entrepreneurship and the challenges faced by small business owners.

As the journalism industry grappled with the disruptive force of the internet, Loren recognized the need to evolve. He embraced the opportunities presented by digital media and transitioned from print to online journalism.

In 2018, Loren took a leap of faith and launched 21 Hats, a media platform dedicated to serving the needs of small business owners and entrepreneurs. 

Drawing on his extensive network and expertise, he created a daily newsletter, a weekly podcast, and in-person events to foster a supportive community and build a business.

But media, even niche media, isn’t easy. It’s hard to get people to pay for content. One revenue stream Loren has been developing is paid in-person events with select groups of business owners. 

He facilitates them through conversations about the successes and challenges they face and creates a sense of community.

At his most recent event, many of the owners present challenged Loren to ensure his business was stable and viable going forward. While the podcast and newsletter have a sponsor and the in-person events have helped bring in more revenue, the business is still small.

That got me thinking about all the new business models I’m seeing coming out of media and which ones are the most viable. The traditional model of advertising-based media is breaking down but the new models open up a lot of possibilities.

The New Media models: 

  1. Subscription: This is the New York Times and Substack model. Get people to pay you every month for the content you produce.

    It works well for a few but I don’t see this as a viable option for most creators. This model is worse than a Pareto distribution. It seems like 1-5% of the creators make 95% of the money. 

    In newspapers, it’s only the NYTimes and Wall Street Journal that have done it successfully in the US and the number of Substack authors making 6 figures is probably measured in the 10s, not 100s.

  2. Advertising: This is the old model but a few have put in a new twist. Social media channels like YouTube do support a few creators. I certainly think new media businesses should sell advertising but as with subscriptions, only the very top people will make a living at it.

  3. Events: As Loren has found, few can live by advertising alone. A natural extension of a content business is an event business. Bring your audience together. 

    They like you and probably want to meet each other. I like this as a supplementary business. It’s normally very profitable but events wax and wane and it can be difficult to maintain them over long periods.

  4. Captive Advertising: This is a new model that I think is one of the most interesting. A company that sells another product or service builds or buys media that can add customers to its offering. It’s not the same as advertising. You can interact with potential customers in owned media in a lot more granular ways than simply buying ads. Hubspot’s purchase of The Hustle was a recent example. 

    We’ve also seen X and YouTube superstars like Nick Huber, Shaan Puri, and The Hustle founder, Sam Parr, build businesses off their social media presence. 

    Nick and Shaan received equity in an offshoring placement startup called Support Shepard and drove significant growth through their social channels. Sam Parr launched the entrepreneur community, Hampton, and drove it to 8 figures in a short period. Mr. Beast is selling lots of chocolate. This is compelling.

    The only flaw here is that it requires a huge audience usually centered around an individual creator.

  5. Data Products: This is another super intriguing model. The idea is to build niche communities through content creation and use it to collect data on that community. For example, Craig Fuller founded Freightwaves as a news site covering the logistics industry.

    Over time he has built out proprietary data products that track the cost of freight, help you model your supply chain, etc. Data products are highly valued recurring revenue streams. 

    Additionally, Frieghtwaves isn’t driven by any single creator. It takes a traditional media approach of using multiple writers to cover a variety of stories but gears the attention gathered from that towards the ultimate goal of creating and selling data products.

These models aren’t mutually exclusive. Frieghtwaves still makes lots of money from advertising and events but most of its value in any potential sale will come from the data products. Not to mention that not relying on events helped a lot during the pandemic. 

Loren's journey has hit a few of these notes. He has advertising and now events. The 21 Hats community of business owners and entrepreneurs is certainly a valuable one. Let’s see where he takes it next. He has laid the groundwork for success.

As 21 Hats continues to evolve, Loren's ability to navigate the challenges of entrepreneurship while staying connected to his journalistic roots will be key to unlocking the platform's full potential.

📅 Next Week:

Next week we are going to deep dive into Patrick Dichter, Owner of Appletree Business Services. We will explore many topics including the challenges of company acquisitions. 

Keep growing,



The most recent episode of The Small Business Mentor Podcast is live. My guest this week was Michael Greenberg, the digital operations extraordinaire. We discussed many things including how digital operations will revamp the future. 

Check it out here: 


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