https://simonowens.substack.com/

I just passed my one-year anniversary of launching my paid newsletter, so I decided to dive into some of the biggest lessons I learned during that time.

If you review Kevin Jones’s resume on LinkedIn, it’s easy to see why he ended up founding a sports podcast network. He’s worked in virtually every sector of the sports media industry, from creating content for pro football teams to reporting for traditional radio stations to writing for sports news sites. He also launched Striking Gold, a 49ers-focused podcast that eventually accrued several thousand listeners.

But Kevin wasn’t content with simply being a podcast personality. Back in 2018, he began to notice that there were a lot of people like him -- podcasters with extremely passionate fan bases but no way to convert that fandom into actual revenue. So he began pitching them one by one on joining Blue Wire Podcasts, a network that would help them produce their shows and sell advertising in exchange for a cut of the revenue.

Flash forward two years, and Blue Wire has since taken on several million dollars in investment, is now producing narrative documentary podcasts, and recently signed a huge deal with one of Las Vegas’ biggest hotels.

I recently sat down with Kevin to discuss how he convinced podcasters to join his network, his approach to working with talent, and why he’s doubling down on longform narrative series.

Over the past year, thousands of journalists have announced the launch of their paid newsletters, which are often hosted on platforms like Substack. Writers with already-existing large audiences have seen immense success with this strategy, pulling in six figures incomes within weeks of debuting their new newsletters.

But the vast majority of writers don’t have huge Twitter followings to promote their newsletters to. For them, growing a sustainable media business can take years of work, and many don’t have enough savings in the bank to hold out for that long.

That’s why we’re seeing a new trend in which writers team up to launch bundled subscriptions. This approach allows writers to cross pollinate their audience growth and ramp up content production to make a subscription much more worthwhile. Publications that include Defector, the Discourse Blog, Brickhouse, and Every have seen tremendous success with this model.

To understand how these writer cooperatives work, I spoke to Mark Stenberg. Stenberg runs his own Substack newsletter and has spent the last few months reporting on the creator economy for Business Insider. He recently moved over to Adweek to cover the media beat.

The last 15 years have not been kind to the local news industry, with thousands of newspapers either reducing staff or closing down entirely. But not all newspapers have been affected equally, and some of the hardest hit chains were owned by hedge funds and private equity firms that had no actual interest in investing in journalism.

Family-owned newspapers seemed to have fared better, and that seems to be the case for Forum Communications, a chain of newspapers and other media outlets situated in the midwest. A few years ago, the company’s newspapers rolled out a digital subscription model, and so far it seems to be performing above expectations.

I recently interviewed Stephanie Schroeder, Forum’s Chief Digital Marketing Officer, about the gargantuan amount of work that went into this pivot and what strategies resulted in the most success.

According to some estimates, corporations across the world spend upwards of $42 billion a year on content marketing, and they do so with the philosophy that by acting like media companies, they can engender trust with potential customers and drive sales.

One of the people who helped sell the corporate world on this marketing philosophy is Joe Pulizzi. In 2007, Joe founded the Content Marketing Institute, and through its constellation of articles, videos, courses, and conferences, it convinced thousands of executives that the frictionless distribution of the internet allowed virtually everyone to become a media company.

I recently interviewed Joe about his journey. We discussed whether freelance journalists should take on content marketing gigs, which companies have been particularly good at content marketing, and whether we’re currently in a content bubble.

Like a lot of people on the political Left, Geoff Sharpe grew frustrated by how successful conservatives were on Facebook. For years, he watched as right leaning conservative groups built huge Facebook followings, which allowed them to promote their highly partisan views to millions of Canadian citizens.

So Geoff and his colleagues decided to do something about it. They initially launched their own left-leaning Facebook page, growing it to hundreds of thousands of followers. But they then wanted to pivot to something even more ambitious: a standalone website that published original content from leading progressive voices.

To do this, they launched a crowdfunding campaign, and over the last year they’ve rolled out a membership offering that helps generate recurring revenue. I interviewed Geoff about why the political Right does so well on Facebook, how he designed the membership program, and what impact his site has had on Canadian politics.

There’s a common misperception that many non-lawyers have about how legal contracts are written. Most people probably assume that a lawyer writes each contract from scratch, but in reality the lawyer is most likely copy and pasting clauses and sections from already-existing contracts and modifying them for their particular client.

One of the resources lawyers often turn to for this is Law Insider. Founded in 2010, Law Insider indexes the millions of contracts that have been uploaded to the SEC website by publicly traded companies. It generates over 4 million monthly pageviews and has over 250,000 registered users, about 5,000 of which pay $30 a month to access its archives.

I recently interviewed the site’s co-founder Preston Clark about how he and his partner came up with the idea, what they did to build up its massive audience, and why they’re expanding into a full-fledged media company that produces everything from articles to YouTube videos.

Over the past year, dozens of writers have left their mainstream media jobs to launch their own standalone newsletters and publications. In almost every case, the writer monetized his content through paid subscriptions, usually with a tool like Substack.

Rick Ellis never bothered with paid subscriptions. Instead, his website AllYourScreens.com generates so much traffic each month that he’s able to make a good living mostly through programmatic advertising.

Ellis has been operating AllYourScreens.com off and on since the early 2000s, but a few years ago he decided to abandon traditional media completely to focus on the site full-time. I recently interviewed him about how he found his audience, what his weekly writing schedule looks like, and why he has no interest in building out a paid subscription business.

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Max Rofagha didn’t have a background in media prior to launching Finimize. He also didn’t have a background in finance for that matter. It was while conducting research on how to manage his own investments that he saw an opportunity for a daily newsletter aimed at helping millennials become more literate in finance.

Flash forward four years and Finimize now has over 1 million subscribers, a staff of financial analysts, and a worldwide community of young professionals who often meet up for in-person events.

I recently interviewed Max about his early audience development strategy, how his subscribers organize their own in-person events, and why he decided to launch a subscription-funded mobile app.