Longform interviews with media entrepreneurs

This is an ongoing repository of my case study interviews. I’m compiling it to make it easier for new subscribers to access older case studies.

Link: How a former travel journalist built a paid membership community for the PR industry

Kelsey and Derrick Ogletree designed Pitchcraft to serve as a liaison between PR consultants and journalists.

Link: How Living Cozy leveraged product reviews to build a successful ecommerce business

Founder Ash Read explained how he built up search authority in a crowded content niche.

Link: How Freetrail carved out a media niche for one of the country's fastest-growing sports

Ultra marathoner Dylan Bowman grew a highly diversified company on the back of his personal brand.

Link: How the Sunday Long Read newsletter built a thriving membership by curating longform journalism

Don Van Natta Jr. and Jacob Feldman grew the newsletter to over 25,000 subscribers.

Link: How the GameDiscoverCo newsletter launched a data product for game developers

Simon Carless carved out a niche in the gaming industry by tracking the metrics around game releases.

Link: How the Tangle newsletter reached 77,000 readers and $624,000 in annual revenue

Isaac Saul wanted to create an antidote to the hyper partisan media ecosystem that dominates the web.

Link: This local news outlet carved out a lucrative niche by targeting Indianapolis women

Leslie Bailey explained how Indy Maven grew from a weekly newsletter into an events and coworking company.

Link: How Oovvuu grew its video platform to over 400 million streams per day

Ricky Sutton co-founded the company to help publishers claw back advertising dollars from the Google/Facebook duopoly.

Link: How a blog about the VC industry generated over $1 million from online courses

John Gannon built an audience with VC job postings and then monetized through a mix of online courses, productized services, and sponsorships.

Link: How a B2B outlet that covers the corporate travel industry built up a loyal subscriber base

The Company Dime mostly eschewed sponsorship revenue and focused instead on delivering high-quality journalism.

Link: How Man of Many grew into the largest men's lifestyle media outlet in Australia

Frank Arthur and Scott Purcell realized early on that content consistency was paramount.

Link: How two graduate students launched the leading biotech publisher in Europe

Co-founder Joachim Eeckhout explains how Labiotech.eu filled an information gap for Europe's fast-growing biotech scene.

Link: How a kids-focused podcaster reached 1 million monthly downloads

Jim Jacob accidentally stumbled upon a huge market opportunity when he launched Kids Short Stories.

Link: How investment newsletter The Daily Upside reached 300,000 subscribers

Founder Patrick Trousdale explained his growth and monetization strategies.

Link: How a former Cosmo editor built Australia's largest women-focused media company

Mia Freedman started Mamamia as a one-person blog and bootstrapped it into a multi-media outlet that reaches 7 million people.

Link: How a college student launched one of the most influential B2B sports media companies

Adam White explains how Front Office Sports grew from a college project into a media powerhouse.

Link: How a podcast for entrepreneurial parents generates $200,000 a year

Sarah Peck explains why she didn't chase scale when building her Startup Parent podcast.

Link: How Starter Story grew to 1.4 million monthly visitors and $500,000 in annual revenue

Founder Pat Walls discussed how he automated his process so that the site now operates as a sort of flywheel.

Link: How Big Cabal Media became one of the fastest-growing news outlets in Africa

CEO Tomiwa Aladekomo walked me through the company’s origin story, explained why he joined in 2018, and outlined its monetization strategy.

Link: How an interest in whiskey birthed a thriving media company

The Whiskey Wash capitalized on the rise of craft distilleries and is almost entirely funded through digital advertising.

Link: How Maria Brito used Instagram to build a 7-figure art consulting business

She eventually grew her audience to over 200,000 followers across Instagram, Facebook, Twitter, and email.

Link: How an engineering student accidentally started a thriving science news site

Hüseyin Kilic grew Interesting Engineering into a media behemoth with over 15.5 million social media followers.

Link: Was Randy Cassingham the first member of the Creator Economy?

In 1994, he launched This is True, one of the first email newsletters, and grew it into a thriving business.

Link: How ScoopWhoop became one of India’s most viral publishers

The BuzzFeed-like site has built two popular channels on YouTube, one of which serves as a counterbalance to partisan TV news.

Link: Judd Legum proved that investigative journalism can thrive on Substack

The former ThinkProgress editor has over 150,000 signups and at least 7,500 paying subscribers to his newsletter.

Link: Can a hit YouTube channel thrive after its founder departs?

The King of Random had 8 million YouTube subscribers when Grant Thompson suddenly decided he didn't want to create videos anymore.

Link: How Taegan Goddard built a thriving paid membership for Political Wire

He already had a robust advertising business, but he wanted to foster a deeper connection with his audience.

Link: This YouTuber built a massive following with pop music guitar lessons

A lot of people conduct searches for instructions on how to play their favorite songs.

Link: How Josh Spector monetizes his 25,000 newsletter subscribers

Through a mixture of consulting, advertising, and paid subscriptions.

Link: How The Discourse scaled its business model to 34 local news sites

The media startup developed a membership model that involves asking the audience what news should be covered.

Link: Daily Detroit is proving there’s a market for local podcasts

Jer Staes monetizes his podcast through a mixture of local business advertising and paid memberships.

Link: How a VC investor grew her newsletter to over 100,000 subscribers

Codie Sanchez finds interesting ways to make money and then reverse engineers them for her audience.

Link: Inside the career of a successful ghostwriter

Jonathan Rick’s writing appears in hundreds of mainstream publications, but it rarely includes his byline.