Episodes
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Today, the personal finance content niche is absolutely ginormous. You can’t open up YouTube, TikTok, or Instagram without encountering an influencer who gives advice on how to make and save money.
Today’s guest Philip Taylor anticipated this content explosion all the way back in 2011. That’s when he launched FinCon, a conference specifically designed for personal finance content creators. That first year he attracted around 250 attendees, but over the next decade it grew into the largest conference in this niche, attracting over 3,000 attendees a year.
In our interview, Philip walked us through how he got into the personal finance space, his strategy for growing the conference, and his ambitions for launching similar conferences in other niche categories.
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I’m sure just about everybody has had the experience of looking at a celebrity memoir and wondering: did they actually write that? In many cases, they didn’t, at least not by themselves. There’s actually an entire shadow economy of ghost writers who do the bulk of the work on these books – not just for celebrities, but all kinds of public figures ranging from big-name CEOs to politicians.
But how does one go about hiring a ghost writer? And what’s it like to work with one? To answer these questions, I turned to Dan Gerstein, the founder of Gotham Ghostwriters, an agency that specializes in connecting clients to professional ghostwriters.
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Ben McCarthy didn’t set out to create a media company focused on Salesforce, he just began blogging about his use of the product as a way to document the various use cases he encountered. As it turned out, there were thousands of other people who were encountering those same use cases, and via Google searches they began landing on Ben’s blog posts.
Fast forward 10 years, and he now runs a 20-person media company that generates over 1 million pageviews per month and is the most authoritative resource for Salesforce customers.
In our interview, we discussed why there’s such a huge audience for Salesforce content, how he monetizes with webinars and white papers, and whether he wants to launch more media outlets centered around other cloud technologies.
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When Joe Pulizzi launched The Tilt in 2021, he already had a pretty good idea of how to build a successful media company. Back in 2017, he had sold his previous media startup, The Content Marketing Institute, to one of the world’s largest event conglomerates.
Joe ran The Tilt with a very similar playbook – first starting with a weekly newsletter, and then expanding into an in-person conference called The Content Entrepreneur Expo, or CEX. The venture was so successful that he sold it to Lulu Press in 2023.
In our interview, Joe talked about his newsletter growth strategy, what it takes to put on a successful conference, and why he prefers the term “content entrepreneur” instead of “creator.”
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When it comes to knowing all the intricacies of real estate investment, few are more knowledgeable than Brad Hargreaves. In 2015 he founded Common, a company that manages rental properties and consults with real estate investors on building design.
And then in 2022 Brad decided to begin sharing his knowledge through a paid newsletter called Thesis Driven. Within a matter of months, it was generating six figures in revenue, and he decided to step down from his role at Common so he could focus on building out a data platform geared toward real estate investors.
In our interview, we talked about why he launched Thesis Driven as a paid only newsletter, how his content is differentiated from most other real estate journalism, and why he think there’s an opportunity to build a Bloomberg Terminal for real estate investors.
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I spend most of my time on this show interviewing entrepreneurs who founded English-language media outlets – mostly because that’s the only language I speak – but that doesn’t mean I’m not interested in the media ecosystems from other regions in the world. That’s why I was super excited to talk to Andreas Sator, the host of one of the most popular podcasts in Austria.
Andreas got his start at a major newspaper, and after a few years at the outlet, he got to experiment with writing an explainer journalism column about personal finances. He found this sort of reporting to be much more enjoyable, so in 2018 he launched a podcast that roughly translates to “Explain The World to Me.”
In our interview, we discussed the Austrian podcast market, how he monetizes the podcast, and why he decided to launch a new show about climate change.
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Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump into the comments section of the post and ask me any questions they have about the media industry or creator economy.
Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.
We answered questions on a range of topics like:
Which media companies are succeeding with native advertising
The best ways for media outlets to run live events
How to grow your audience in a world where Google and Facebook are sending less and less traffic
What a Substack advertising platform would look like.
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Before William Knight launched Early Morning Media, he had worked for years at a company that specialized in sending press clippings to corporate clients. While these services were mostly utilized by a client’s internal communications team, William realized at some point that these same news curation practices would be appreciated by an external audience.
So in 2011, he launched B2B newsletters covering multiple industries. At first, these newsletters were monetized mostly through paid subscriptions, but as the company expanded he began to roll out free, ad-supported newsletters as well. Today, Early Morning Media operates over a dozen newsletters that are read by 500,000 industry professionals.
In our interview, William discussed the company’s origin story, its method for curating news, and the decision process for launching a new newsletter.
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The rise of cloud computing introduced all sorts of benefits for the enterprise software space. Not only could license holders access their accounts from virtually anywhere, but it also allowed the software companies to issue updates on a more regular basis. But this also made the sector a lot more complicated and created a need for more experts who could educate cloud software customers about the intricacies of the tools.
Tom Arbuthnot is one of those experts. For over a decade, he’s been a Microsoft MVP and Microsoft Certified Master, and he spent a significant amount of time in the early 2010s educating the public about these products through blogging and conference talks. But then in early 2022 he realized that there was a market opportunity for a media company to cover these products. That year, he launched Empowering Cloud, an online community that produces a mixture of videos, live calls, and other educational materials centered around Microsoft’s cloud technology.
In my interview with Tom, we talked about the site’s launch, how he finds sponsors, and why he decided to lock most of the company’s content inside a community platform that requires a login.
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I think everyone likes to think of themselves as being financially savvy, especially if, like me, you write about business topics, but how many of us truly understand finance terms that are bandied about like gross profit and lifetime value. Like we may know that the term EBITDA stands for “earnings before interest, taxes, depreciation, and amortization,” but how many people actually know how to calculate it?
CJ Gustafson knows. After a decade in finance, he’s mastered all the accounting jargon, and a few years ago he realized that there was a market need for someone who could explain these terms in a way that’s both entertaining and informative. So he launched Mostly Metrics, a Substack newsletter about finance, strategy, and operations at startups.
CJ’s since grown the newsletter to over 42,000 subscribers, all while holding down his day job as a CFO at a tech startup. In my interview with him, we talked about why he launched the newsletter, how he balances his day job work and writing, and what his longterm plans are for the newsletter.
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My newsletter: https://simonowens.substack.com/
For most of Instagram’s existence, it wasn’t thought of as a platform for distributing news, but a growing number of media entrepreneurs have figured out ways to leverage its photo and video features to deliver engaging news digests.
One of those entrepreneurs is Sam Koslowski. Back in 2017, he and his co-founder launched The Daily Aus, a social first news outlet that’s grown its Instagram account to over 500,000 followers. As it ramped up its audience on the app, it began to diversify its content offerings across newsletters, podcasts, and YouTube.
In my interview with Sam, we discussed why Instagram was the ideal platform for launching the company, how it monetizes its content, and where he hopes to expand in the coming years.
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Ask about just any media executive, and they’ll tell you that the year 2023 was not a good one for the advertising business. A combination of high interest rates and an uncertain economy made companies extremely skittish, and that caused them to pull back on their marketing spend.
There’s some recent signs that advertising spending is picking up in 2024, but it’s still too early to know how it will shake out.
But what about newsletter advertising? It’s seen some strong growth in recent years and brands have reported higher than average ROI due to the strong engagement that’s seen in the inbox. Has it suffered from the same macro economic forces that battered the larger ad industry?
To answer that question, I turned to Ryan Sager, the co-founder of Who Sponsors Stuff, a data platform that tracks sponsorships across hundreds of newsletters. Ryan dove deep into his own data to determine which sectors are investing big in newsletter ads and whether they’ve seen any slowdown in growth.
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By the time Riad Chikhani was 16 years old, he had already built a hugely successful online community for gamers and then sold it for a healthy sum. Two years later, he founded the company that would eventually become GAMURS Group, and while it took far longer to gain traction, it eventually grew into one of the largesting gaming media companies in the world, with outlets that include Dot Esports, Gamepur, and Gamer Journalist.
In my interview with Riad, we talked about his early business pivots, why he invested big in esports, and how he drives synergies between 17 different publications.
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Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump in the comments section of the post and ask me any questions they have about the media industry or creator economy.
Several of you did pipe in with some amazing questions. I then invited on Alexis Grant, the founder of They Got Acquired, to help me answer them.
We answered questions on a range of topics like
How to monetize newsletters on LinkedIn
How we’d go about launching a local news outlet from scratch
The future of paid newsletters
How The Messenger should have spent its $50 million in VC cash.
This Q&A episode is actually part of an ongoing series. Every single month I’ll allow my subscribers to submit questions, and I’m going to do my very best to answer at least one question from every single subscriber. The only way to submit questions is by becoming a paid subscriber to my substack newsletter.
Subscribers also receive a calendly link from me that allows them to book a half-hour introductory phone call. Many of my subscribers use it as an opportunity to tell me about their own media businesses and pick my brain on strategy.
To subscribe, go to https://simonowens.substack.com/
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My newsletter: https://simonowens.substack.com/
When Jack Karmer and Nick Martell launched their daily newsletter Market Snacks in 2011, they kept their names off the publication so that it wouldn’t jeopardize their finance day jobs. But once the newsletter started to attract readers and sponsorship revenue, they decided to come clean. Luckily, their bosses let them continue on with their side hustle.
Flash forward about a half decade, and Market Snacks had gained enough traction that they both decided to go to business school so they could learn to scale the company. Around that same time, they teamed up with a large podcast network to launch a daily companion show, and almost immediately it was featured on the Apple Podcast app.
This success didn’t go unnoticed. Robinhood, which at the time was a fast-growing stock trading app, came on at first as a sponsor, but a few months later decided to outright buy Market Snacks to leverage it as a marketing channel for the app.
Jack and Nick continued to host the podcast while managing the rest of the Market Snacks team, and then in 2022 they went to the Robinhood executive team with a radical proposition: they wanted to spin off the daily podcast and acquire it from Robinhood. Amazingly, their bosses went for it, and that year they renamed the podcast to The Best One Yet.
In my interview with Jack and Nick, we discussed how they came up with the idea for the newsletter, why Robinhood allowed them to take the podcast back, and what they’ve done with the company ever since they became full owners.
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It’s no secret that local journalism has struggled since the Great Recessions, with hundreds of newspapers shuttering and thousands of reporters losing their jobs. Over the past few years, entrepreneurs have launched dozens of local news startups to help fill in the gap, but there’s still an ongoing debate as to whether local news should be a for-profit or nonprofit industry.
Berkeleyside is one of the few organizations that has tried both models. For the first several years of its existence, it was a for-profit entity, but then in 2019 its founders switched it over to a nonprofit model, and it’s since expanded into three separate verticals that cover the bay area, with a fourth launch planned for 2024.
In an interview, co-founder Lance Knobel walked me through how Berkeleyside came to be, why it switched to a nonprofit model, and how it generates revenue through a combination of grants, memberships, sponsorships, and large donations.
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Lucas Grindley knows something about building sustainable revenue streams for media companies. When he was hired to Here Media, a network of LGBT news outlets, it was losing money, but over a period of six years he nurtured it back to profitability.
Now he’s the executive director of Next City, a 20-year-old nonprofit magazine dedicated to urban policy and equitable cities. When he first joined, the publication was almost entirely reliant on large grants, but he’s since diversified its revenue by building up its ad sales and small-donor memberships. Recently, it crossed the threshold of 1,000 paying members.
In a recent interview, Lucas walked me through his successful tenure at Here Media and explained how he’s brought a similar playbook to Next City.
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It’s been nearly five years since Spotify announced it would diversify its audio offerings beyond music streaming, and while it spent most of that time building its podcast capabilities, it made no secret that it eventually wanted to get into audiobooks.
Then in 2022 it made its first move into the industry by acquiring an audiobooks distributor called Findaway. Later that year, it launched the ability to purchase audiobooks through spotify. And then finally in late 2023 it rolled out audiobook streaming as part of its paid subscription.
There’s been one group that’s watched these developments closely: audiobook authors. They’re understandably nervous about how Spotify’s bundled offering will affect their own income, and many are deeply skeptical of the company’s intentions.
So will Spotify’s audiobook streaming be good for authors? That’s a question I put to Jane Friedman, the writer behind the publishing industry newsletter The Hot Sheet. She walked me through the current landscape of digital audiobook sales and explained how Spotify’s revenue sharing arrangement works.
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There are plenty of popular politics newsletters out there, but none with the kind of unique origin story of Wake Up to Politics. It was started by Gabe Fleisher when he was only 9 years old. While the early editions were sent out by a Gmail account and only read by his mom, Gabe kept at it, waking up early every day before school to write the newsletter. Flash forward about a decade, and he’s now a senior at Georgetown and Wake Up to Politics has close to 50,000 subscribers.
In my interview with Gabe, we talked about what kept him motivated all these years, how he monetizes the newsletter, and what he plans to do with it once he graduates.
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Subscribe to my newsletter: https://simonowens.substack.com/
Earlier this month, I sent a newsletter to my audience with the subject line: “Ask me a question.” Basically I told everyone to jump in the comments section of the post and ask me any questions they have about the media industry or creator economy.
Several of you did pipe in with questions, and so I spent a few hours jotting down notes and then recording this episode you’re about to consume.
I answered questions on a range of topics like the difference between a creator-led company and traditional media outlet, non-traditional media business models, my advice on launching a media business in 2024, and how long it takes to build a media business from scratch.
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