What Works for Startups Like Yours?

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.

First customers: word-of-mouth

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.

Real Vision is a financial education and macro investing platform founded by Raoul Pal in 2014. Starting from Spain as a monthly macro research publication called Global Macro Investor, Pal evolved the company into a comprehensive content platform covering markets, crypto, and macroeconomics through interviews, analysis, and educational content. The platform grew significantly through content marketing and has established itself as a trusted voice in crypto and macro investing.

John Lee Dumas built Entrepreneur on Fire, a daily podcast interviewing successful entrepreneurs, which grew to over 1 million unique monthly listeners. Leveraging this audience, he launched Podcasters Paradise in October 2013, a membership community teaching podcast creation, growth, and monetization. The community has generated over $3 million in revenue with 2,500 members through strategic pricing increases (starting at $197, now $1,297) and scarcity-driven cart opens, with June 2014 bringing in over $360,000 in monthly revenue.

First customers: Email list of 4,000 subscribers built from podcast listeners directed to website via call-to-action in show intros/outros

Dory Clark is a bestselling author, keynote speaker, and business consultant who successfully diversified her revenue from consulting into a multi-stream business including book sales, speaking engagements, and coaching. Starting with her first paid speaking gig of $5,000 in 2013 for her book 'Reinventing You,' she scaled to delivering 59-61 talks annually and generating $125,000-$150,000 from speaking alone in 2015, while her books have sold over 30,000 copies (Reinventing You) and 6,000+ copies (Stand Out) within months of launch.

First customers: Referral from casual acquaintance for a speaking engagement at a large association convention

John Nastor launched Hack the Entrepreneur podcast on September 5th and grew from 2,600 downloads in month one to 56,000 in month two through aggressive content production (3 episodes/week) and strategic partnerships. He built an email list of 943 engaged subscribers and generates consistent revenue through mid-roll ad spots ($300 per episode) on Midroll.com, earning enough to support a full-time living with a team of VAs, editors, and designers. He later partnered with Copy Blogger Media to create Showrunner.fm, a podcasting course and companion podcast.

First customers: Direct outreach to potential sponsors and podcast networks

Collin Kartchner and Samir Chaudry launched the Lacrosse Network in 2011 as a YouTube channel aggregating lacrosse content. After struggling to monetize through traditional ad models, they pivoted to service work and secured live sports rights on YouTube, which attracted the platform's attention. The company was acquired by Whistle Sports in 2014 as an acq-hire. Today, they run the "Collin and Samir" YouTube channel with 813K subscribers, a seven-figure advertising-based business, and an accompanying newsletter, focusing on creator economy content and interviews.

First customers: Collin uploaded a trailer for a video about the Colorado club lacrosse team; Samir saw it and emailed him suggesting he put videos on the Lacrosse Network.

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.

First customers: Direct outreach from companies in the same space who connected with Milo and were presented with sponsorship packages

Kevin Van Trump transformed his background as a rural farm kid and commodities trader into The Van Trump Report, a farm newsletter generating $18M in annual revenue while operating with just 4 people. The newsletter provides valuable insights on agricultural markets, farming economics, and industry trends, resonating with farmers and agricultural professionals. His success inspired others, including Shaan Puri, to launch related ventures like Milk Road in the same space.

Every is a bundle of business-focused newsletters structured as a collective, founded by Dan Shipper and Nathan Baschez. The model aims to make writers happier and provide readers with better content while maintaining profitability. The founders discuss their strategy for acquiring readers and writers, and how bundling serves as a strategic approach for indie hackers.