Content Startups

Whitson Gordon is editor-in-chief of How To Geek, having built his career from a 2009 internship at Lifehacker where he grew the publication from 4 million monthly uniques to 15 million. He attributes growth to a balance of quality content (50%) and effective marketing tactics (50%), emphasizing strong headlines, strategic linking, and multi-channel promotion. Now running How To Geek, he applies the same content-first philosophy while maintaining editorial independence from revenue operations.

Shelf Media is a digital-only publishing company founded by Margaret Brown in 2010 that creates niche magazines including Shelf Unbound (indie book reviews with 125,000 readers across 75+ countries), Middle Shelf, and newly launched Podster (about podcasts). The company generates revenue through advertising and competitions, with Shelf Unbound alone generating approximately $120,000 annually from ad sales at $20,000 per bi-monthly issue, plus $40,000 annually from a book competition with 1,000 entries per year.

Chris Guillebeau is a bestselling author and entrepreneur who has built a diversified business around content creation, books, and online communities. His book 'The $100 Startup' sold over 300,000 copies, generating multiple six figures in annual royalty income, with his total business split 50/50 between traditional book royalties and online products (membership sites, courses, guides). His primary growth driver has been relationship-building with influencers and his community of 100,000-130,000 email subscribers.

NowThis is a digital-first news and media company focused on creating short-form video content for social platforms. As of January 2016, they achieve approximately 1 billion monthly views across all channels and had just closed a $16 million funding round with a team of about 50 full-time employees. Their success comes from data-driven content optimization, particularly on Facebook video, where they've pioneered techniques like volume-agnostic videos with on-screen text and close-up interview formats designed for mobile consumption.

Gerard Adams co-founded Elite Daily, a content-focused online publication targeting millennials, initially bootstrapped with $60,000 of his own capital. The site grew to 80 million unique visitors at the time of acquisition by Daily Mail, generating approximately $20 million in annual revenue through display and native advertising. Elite Daily's growth was driven by high-volume content creation (80 articles per day), trend-based writing, and strategic use of social platforms to distribute content.

Emerson Spartz is a viral media entrepreneur who started MuggleNet at age 12, growing it to 50 million monthly page views through link swaps, content curation, and recruiting a 120-person team. He later founded Dose, a data-driven content platform that now reaches 15 million unique monthly visitors and 27 million social followers with just 6 writers and 50 total employees by leveraging machine learning algorithms (Kepler, Dante, Lindell, Lovelace, Darwin) to predict viral content and optimize headlines and thumbnails. The company has raised $35 million and monetizes through programmatic advertising while building native advertising products for brands.

Jason Hartman is a serial entrepreneur and real estate investor who has built a media empire around podcasting, most notably The Creating Wealth Show, which has over 640 episodes and reaches listeners in 164 countries with approximately 5,000 downloads per episode. His primary revenue comes from his real estate investment company that helps clients invest in properties, generating approximately $2.4 million in referral fees from managing around 500 properties annually. He leverages his popular podcast as a marketing tool to drive attendance at Jason Hartman University events and promote his real estate investment services.

Stacking Benjamins is a financial entertainment podcast launched in March 2012 by Joe Saul-Sehy that grew to 152,000 monthly downloads by featuring accessible, magazine-style money content with personality. The show generates approximately $5,500 monthly from two main sponsors (Magnify Money and SoFi) at an 18 CPM rate, operates with minimal production costs (~$480/month), and is expanding into online courses to monetize the audience attention.

Milo is a content and newsletter platform for freelancers, founders, and creative entrepreneurs, started in 2009 as a side project called GraphicDesignBlender.com. It took 4-5 years before generating meaningful revenue, but now generates $8,000/month through sponsorships from relevant SaaS companies. With 30,000 email subscribers growing by 1,500/month, Preston has built a profitable business working only 5-8 hours per week while maintaining a full-time job.

Ilias Segalexis is a former software developer who left a €40,000/year corporate job in Greece to build a media company targeting the software development industry. His network of properties (primarily Java Code Geeks) reaches over 1.5 million people per month and generated mid-six figures in 2015 with an 85% net margin through advertising, sponsorships, and lead generation partnerships.

Alex Skatell bootstrapped Independent Journal Review from a Charleston apartment in 2012 to become a top 50 U.S. website reaching 20-25 million monthly unique visitors. The company operates as a media holding company (MGA) with three branches: a newsroom (50+ reporters), a technology division building internal tools, and an agency providing audience building and analytics services. Funded by $2.5M in friends and family capital, the company remains profitable and focuses on owned distribution channels (email list of 700k, social media) rather than relying on viral traffic.

Nathan Chan launched Founder Magazine in 2015 as a digital publication featuring interviews with successful entrepreneurs. Through aggressive Instagram growth strategies (posting 5-10 times daily with a virtual assistant), he built the account from zero to 700K followers in 16 months, generating 150,000+ email subscribers. Revenue comes from multiple streams including magazine subscriptions, digital courses (Instagram course and Founders Club membership with 400 paying members), and a weekly podcast with 70,000 monthly downloads.

Ash Kumara built Trade Craft as a digital content network for millennials while generating significant revenue through book sales and speaking engagements. His book 'Confessions from an Entrepreneur' sold over 150,000 copies, generating approximately $300,000-$450,000 in revenue through a B2B approach targeting college entrepreneurship programs. By 2015, Kumara was generating approximately $90,000+ annually from speaking engagements (averaging $5,000 per speech) plus book royalties and startup advisory work.

The Slow Hustle is a long-form interview podcast launched in January 2015 by Peter Awad, who juggles podcasting alongside three other businesses (Import Auto Performance, Mission Meats food brand, and a previous failed startup). The show generates approximately 8,000-10,000 downloads per month with around 2,000 downloads per episode, and recently landed on the iTunes Podcasts homepage through authentic relationships rather than gaming the system. Peter has secured two sponsors (Iowa Startup Accelerator and a law firm) charging $3,000 per 16-episode package, generating roughly $187 per episode, covering costs while maintaining the show as a labor of love.

Nathan Latka runs a daily podcast interviewing SaaS founders about their metrics and growth tactics, having produced nearly 1,000 episodes. Facing frequent legal threats from boards demanding episode removal due to transparency concerns, he shut down the show but then pivoted to a Patreon-based monetization model. In a test of customer commitment, he raised $527 from 9 patrons willing to pay for exclusive content, validating audience demand and launching a tiered subscription offering exclusive episodes, metrics calls, and monthly data exports at $5-$500/month.

Pursuit is a daily self-development email newsletter founded by Case Kenny with 172,000 subscribers that generates revenue through brand sponsorships at $30-40 per 1,000 opens. The company made approximately $100,000 in revenue last year and is projecting $800,000-$900,000 for 2019 through a diversified monetization strategy including sponsorships, events, and digital products. With just two team members in Chicago, Pursuit maintains a 39% open rate and 2% advertiser click-through rate by strategically managing advertiser frequency and only exposing subscribers to sponsors after 28 days of engagement.

Blockworks Group, founded in 2017 by Jason Yanowitz, is a media and education company focused on blockchain, cryptocurrency, and their intersection with macroeconomic markets. The company produces events, educational content, and podcasts analyzing how monetary stimulus, inflation, and currency debasement are driving institutional and retail adoption of alternative assets like Bitcoin. Yanowitz's thesis centers on Bitcoin as an inflation hedge and alternative to government-controlled fiat currency, particularly as central banks increase monetary stimulus.

SaaStr is a SaaS community and events platform founded by Jason Lemkin in 2015, generating $25M in annual revenue through a combination of ticket sales (~$5M), sponsorships ($20M), and other revenue. The company grew from 800 attendees at its first one-day event in 2015 to over 10,000 people at its flagship annual conference, with growth driven primarily by word-of-mouth and email marketing to a curated 120,000-person community list. The business operates lean with only 10 full-time employees plus embedded agency partners, emphasizing quality over scale and community value as its core moat.

CJ built Mostly Metrics, a newsletter for CFOs launched in December 2020, starting from zero subscribers by obsessively engaging on Twitter around relevant keywords and partnering with B2B companies like Ramp and Brex. The newsletter grew to 35,000 subscribers (7,000 of whom are actual CFOs) in 1.5 years with a 46% open rate and 5-7% click-through rate, attracting sponsorships of $5-10k per post and up to $100k for bundled deals. He also launched a podcast called Run the Numbers with Turpentine Network while maintaining his full-time role as CFO at Parts Tech, planning to transition fully to media within three years.

MostlyStories.com is a content platform founded by Jeff Pecaro, a talented copywriter. The company is known for creating content for Dynamite Circle's in-person events, including their annual DC BKK gathering in Bangkok.