The Long Story with Simon Owens

Simon Owens
  • 4.8 (28)
  • NEWS COMMENTARY
  • UPDATED BIWEEKLY
The Long Story with Simon Owens

The Long Story features the best longform journalism on the internet.

  1. 1 DAY AGO

    How The Dispatch is diversifying beyond just subscription revenue

    My newsletter: https://thelongstory.substack.com/   The Dispatch was launched in 2020 with a pretty straightforward thesis: that people would pay for quality, fact-based journalism. It certainly had a partisan lean – it was co-founded by conservative journalists Jonah Goldberg and Steve Hayes after all – but it steered clear of the wholesale rejection of reality that’s rampant in most pro-Trump media.   Flash forward to 2025, and that thesis has been vindicated. It recently crossed 45,000 paid subscribers without the help of huge VC investors. Now, it plans to diversify its revenue streams, and to accomplish that it brought on Mike Rothman, a longtime media veteran who helped build companies like Thrillist and Fatherly.   In a recent interview, Mike walked through his decision to join The Dispatch, what kind of advertising he wants to sell, and why brands are suddenly interested again in sponsoring politics media.

    58 min

  2. FEB 12

    Mill Media proved that audiences would pay for local news

    My newsleter: https://thelongstory.substack.com/ When the Manchester Mill launched in 2020, it operated on a simple theory: that local audiences would pay for news as long as it was original and differentiated. It quickly proved that model out and was able to hire its first full-time employee within a matter of months. From there, founder Joshi Herrmann decided to replicate this model across other cities in the UK, and Mill Media now runs six publications that have collectively generated tens of thousands of paid subscribers. In a recent interview, Joshi discussed why he first got interested in local news, how he decided to expand to different cities, and whether he thinks his model can be replicated by other local news startups.

    42 min

  3. JAN 30

    This Colorado food writer came up with a novel way to monetize his content

    My newsletter: https://simonowens.substack.com/   When Matthew Schniper launched his Colorado Springs food newsletter in 2023, he ran into a problem many local news entrepreneurs face: he didn’t have enough time to do his reporting and chase down advertisers.   Luckily, by that point he already had strong relationships in the Colorado Springs food scene, and so he approached 12 of his favorite restaurants with an interesting proposition: if they came on as annual sponsors, he would go above and beyond to feature them in his newsletter, and he wouldn’t allow any other local businesses to advertise. This allowed him to focus on his reporting and not waste time on sales calls. The experiment was so successful that over half of the restaurants have already renewed for a second year.   In a recent interview, Matthew explained how he came up with the idea, what services he provides for these 12 restaurants, and why he thinks his model can be replicated by other local news startups.

    1 hr

  4. JAN 23

    How 1440 scaled its newsletter to 4 million subscribers

    My newsletter: https://simonowens.substack.com/ What’s the true monetary value of a newsletter subscriber? Tim Huelskamp knows the answer to that question. As the co-founder of the 1440 newsletter, he knows how many emails the average subscriber will open, how much money they’ll generate in ad revenue, and what it costs to acquire them. It’s this ruthless approach to unit economics that allowed 1440 to grow to over 4 million subscribers, all without raising any VC investment. In a recent interview, Huelskamp walked me through the original idea behind the company, how he and his co-founders generated their first few thousand subscribers, and why 1440 is now expanding beyond the inbox into topic-based explainer content.

    56 min

  5. JAN 13

    How Scott Porch helps podcasters grow and monetize their audiences

    My newsletter: https://simonowens.substack.com/   2024 was a big year for the podcast industry. Not only were there several huge deals signed, but podcasts wielded significant influence in the US presidential election. These days it’s impossible to open YouTube, TikTok, or Instagram without coming across podcast clips, and the market is still poised for significant growth in the coming years.   But if you run a small-to-mid-sized podcast, it’s still incredibly difficult to make a living from your work. You need to join an advertising network to generate significant revenue, and most networks won’t accept you unless you meet a minimum audience threshold.   To deal with these challenges, many podcasters turn to Scott Porch. Scott runs Big IP, a podcast management company that helps podcasters grow their audiences and monetize their content. In a recent interview, he explained how he chooses which podcasters to work with, what value he brings to the relationship, and why he’s bullish on paid subscriptions for podcasts.

    1 hr

  6. 12/19/2024

    How the Money for the Rest of Us podcast built a six figure membership platform

    My newsletter: https://simonowens.substack.com/   David Stein had an innovative marketing hack for growing his investing podcast called Money for the Rest of Us. He put the names of other popular finance podcasts in his metadata, and Apple’s unsophisticated search algorithm would surface his show whenever people were searching for his competitors.   By the time Apple eventually eliminated that functionality, Money for the Rest of Us had built up a loyal audience that’s since downloaded the show over 20 million times. His audience is so loyal, in fact, that it sustains a high-priced membership community that charges $450 a year and generates well into the six figures in revenue.   In a recent interview, David walked me through how he developed his investing expertise, what he offers to paying members, and why he launched his own premium investing app.

    45 min

  7. 12/12/2024

    How Ben Cohen successfully pivoted from advertising to a subscription-based business model

    My newsletter: https://simonowens.substack.com/   In 2017, Ben Cohen was living the dream. His politics news site The Daily Banter was generating over 6 million visits a month and enough advertising revenue to support him and a small stable of writers. But then the floor fell out from under him virtually overnight; Facebook pivoted away from news and sent his traffic plummeting. Without traffic, his advertising revenue crumbled.   So in an act of desperation, Ben pivoted his entire business model into paid subscriptions. Doing so forced him to slow down his publishing schedule and focus on serving his core audience. Slowly but surely, he built up a new revenue base, and in the last few months he passed the threshold of 1,000 paid subscribers.   In a recent interview, Ben explained how he executed on his pivot and why he’s determined to never rely on a single large tech platform ever again.

    1h 4m

  8. 12/09/2024

    How Eric Newcomer used his newsletter to launch a $1.5 million events business

    My newsletter: https://simonowens.substack.com/   Like a lot of journalists=turned-media–entrepreneurs, Eric Newcomer decided to launch a paid newsletter after leaving his job at Bloomberg in 2020. That model yielded 2,500 subscribers who collectively pay over $400,000 a year to access his newsletter about startups, but that’s no longer the biggest part of his business.   Today, Eric generates over $1.5 million a year from the Cerebral Valley AI Summit, a twice-a-year conference that he monetizes through a mixture of ticket sales and premium sponsorships. In a recent interview, he explained the conference’s origin story, how he attracts the right mix of startup founders and VC investors, and why he thinks he can replicate its format across multiple tech industry niches.

    43 min
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4.8
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The Long Story features the best longform journalism on the internet.

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