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If you ask Dave Anderson what he does for a living, he’ll probably tell you he’s retired, but that’s not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of people want to tap into his insights gleaned from 20 years working in the tech industry, including over 10 at Amazon.

In a recent interview, Dave discussed the newsletter’s origin story, how it found its audience, and why he doesn’t have any ambitions to scale it into a larger media company.

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Andrew Fogliato never set out to be a marketing consultant. He was simply trying to succeed as a real estate agent and began creating local online content to promote his listings. His colleagues at RE/MAX quickly noticed that his marketing savvy gave him an edge, and soon he was training other agents across Canada. Eventually, he left RE/MAX to launch his own marketing agency, where he built a strong business helping agents run Facebook ads.

In 2022, Andrew saw an even bigger opportunity. He purchased Real Estate Magazine, Canada’s largest industry trade publication, and immediately began expanding its online presence. In a recent interview, he discussed why he bought the magazine, his approach to monetization, and why he isn’t in a hurry to expand into the U.S. market.

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SailGP is only a little over five years old, and yet the competitive sailing league has already built out a substantial fan base all across the world. Not only are its competitions broadcast on linear TV channels, it also produces an impressive amount of content that includes YouTube videos, social media clips, and podcasts. In 2022, it hired Melissa Lawton, a longtime sports broadcast producer, to run its content operations, and she’s invested heavily in everything from live streaming to highly-produced docuseries.

In a recent interview, Melissa explained how SailGP’s media operations fit within its larger business and walked through her team’s approach to producing both shortform and longform content.

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When Eli Woolery and Aarron Walter launched the Design Better podcast, they did it on behalf of InVision, a tech platform used by designers and other creatives. Aaron was the head of content at the company, and the goal of the podcast was to educate the designer community while also raising awareness of the InVision brand.

But when InVision decided to wind down its content operations, Eli and Aarron negotiated to take over Design Better, and now it’s a thriving standalone business. In a recent interview, Eli talked through everything from the evolving format of the show to how it became an independent media business to its current monetization models.

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When Kevin Raposo launched KnowTechie in 2014, he had no idea it would grow into a thriving tech news outlet – he just wanted journalists to answer his emails. He was working as a PR consultant and figured reporters would be more receptive to his pitches if they considered him to be one of their peers.

But after three years of running the site, its audience blew up, and Kevin was able to hire several writers to expand its coverage. And while the rise of generative AI has eaten into its traffic, KnowTechie continues to drive meaningful revenue.

In a recent interview, Kevin walked me through his accidental entry into content marketing, his strategy for growing KnowTechie’s audience, and how running the site impacts his day job as a tech PR consultant.

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By the time Amy Wilson and Margaret Ables came together to launch a parenting podcast in 2016, both had already achieved some mainstream success in traditional Hollywood. Amy landed multiple roles in TV sitcoms and Margaret had worked for several years as a senior writer at Nickelodeon. They teamed up on the podcast, which is called What Fresh Hell, because it offered them more creative freedom and ownership over their work. Within years, advertisers were beating down their door to reach their enormous audience, which mostly consists of moms. In 2022, they leveraged that success to launch Adalyst Media, a podcast network that sells ads for other shows targeting female audiences.

In a recent interview, Amy walked me through why she left traditional Hollywood, their decision to launch a network, and how she thinks the podcast industry will evolve in the coming years.

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Spencer Macnaughton doesn’t believe there’s a lack of LGBTQ-focused journalism in the mainstream media; as a former producer for both 60 Minutes and the Wall Street Journal, he saw a willingness from these outlets to cover anti gay and trans hate movements. He launched Uncloseted Media last year, though, because he thinks there’s a need for more concentrated, investigative reporting on this type of discrimination, and he convinced several wealthy donors to contribute hundreds of thousands of dollars to help him get it off the ground. Today, it publishes up to two investigative articles per week and has been syndicated by some of the world’s largest media outlets.

In a recent interview, Spencer walked me through how he pitched these donors, why he went the non-profit route, and how he works with other news outlets to amplify his team’s reporting.

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You’ve probably seen headlines by now declaring 2024 to be the podcast election. It certainly did seem like a breaking out point that established podcasts as important messaging vehicles for any future presidential candidates.

But back in 2015, podcasts had far less clout, and most of the political shows that did gain traction were produced in DC and New York. That didn’t stop Sarah Stewart Holland and Beth Silvers, two Kentuckians with very little media experience, from launching Pantsuit Politics, a show that quickly amassed an audience of listeners that were spread out all across the US. They eventually built out a well diversified business that includes advertising, paid subscriptions, and live events, and they’re now trying to expand their reach on YouTube.

In a recent interview, Sarah and Beth explained how they came up with the idea for the show, where they found their audience, and why they don’t host their events in large cities.