Content Startups

Gergé Oros is a former Uber engineering manager who left his $320-330k compensation package to build The Pragmatic Engineer, a paid newsletter on Substack about software engineering. In under a year, the newsletter grew to 189,000 subscribers (with 80,000 added in the last 90 days) and now generates more revenue than his former Uber salary, with subscribers paying for in-depth weekly content.

All the Hacks is a top-tier business podcast launched by Chris Hutchins, a former PM and founder who left Wealthfront to pursue content creation full-time. The podcast explores financial optimization, travel hacks, and life improvement through interviews with interesting people. In 18 months, it reached top 5-10 in business podcast rankings through authentic content, guest curation, and consistent weekly releases.

Lenny's Podcast is a top 10 technology podcast that launched six months before this episode with 50 episodes published, 2+ million downloads, and 40,000-50,000 subscribers across Apple Podcasts and Spotify globally. The podcast interviews world-class product leaders and growth experts on building and growing successful products, using Notion to coordinate operations and guest management.

How I AI is a new podcast launched under the Lenny's Podcast Network, hosted by Clairvaux, an AI-obsessed product leader and founder. The show features practical demonstrations of how people use AI tools like V0, Devin, and Cursor to ship faster and improve workflows, with live screen sharing and 30-minute episodes. The inaugural episode features Sahil Lavengia, CEO of Gumroad, showcasing how AI tools are enabling 40x speed improvements in feature development and driving cultural change in engineering organizations.

Ignite the Drive is a content platform founded by Garrett Dunham, a serial entrepreneur and startup advisor from Silicon Valley, after his previous accelerator Pre-Backed shut down due to burnout and a failed enterprise deal. The site shares tips, tricks, and frameworks for entrepreneurial mental fortitude through blogging and a newsletter. Currently generating revenue in the hundreds of dollars, it operates as a labor of love rather than a primary revenue driver.

Darren Rouse built Pro Blogger starting in 2002 as a personal blog, eventually consolidating 20-30 topic-specific blogs into his two main properties: Pro Blogger and Digital Photography School. Pro Blogger generates ~$4,000-5,000/month from eBooks plus six-figure event profits, while Digital Photography School reaches 4 million monthly visitors and generates over $1M annually through eBooks, affiliate marketing, and advertising. Growth is driven primarily through organic search, content marketing (7-8 pieces per week), and an email list of 950,000 subscribers adding 800 new emails daily.

Results Junkies is Paul Singh's community-driven newsletter and platform that evolved from a blog into a weekly newsletter written during his time as an investor. It's not currently a business, but rather a passion project bringing together a couple thousand founders and investors in Slack and through meetups to discuss building businesses. Paul built this after exiting Disruption Corp to 1776 and spending 30 days traveling to startup hubs globally to understand how communities grow.

Jeff Bullis built a personal brand and content empire by consistently blogging 5 times per week while working a full-time day job at a digital agency, waking up at 4:30 AM for 4 years to fuel his passion. He grew his blog to 250,000 unique monthly visitors, 70,000 email subscribers, and 350,000 Twitter followers, eventually transitioning to full-time content creation and monetization through speaking engagements ($10,000 per keynote), affiliate marketing, and digital products.

The Top is a daily 15-18 minute podcast hosted by Nathan Latka featuring entrepreneurs who are number one or two in their industries by revenue or customer base. The show focuses on extracting real numbers—revenue figures, marketing funnels, customer counts—and was inspired by gaps Nathan saw in shows like Entrepreneur on Fire, NPR/Harvard Business Review, and Tim Ferriss's podcast. Nathan built his first company, HEO, into a SaaS business generating $30k/month in the first three months with $2.5M in funding and 10,000+ paying customers.

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.

Jay Papasan and Gary Keller launched 'The One Thing' book with a concentrated, strategic month-long campaign that sold 27,000 copies in a single week, exceeding their 20,000-copy best-seller threshold. They leveraged three core channels: their internal network of 4,300 real estate agents, an email list of 35,000+ subscribers built on permission-based marketing, and 35 live training events across locations that reached approximately 16,000 people. The book achieved sustained growth year-over-year with sales up 43% in July and 26% annually, driven by word-of-mouth and timeless content strategy rather than short-term promotional tactics.

Billy Murphy built Forever Jobless into a content platform with 96,000 Instagram followers by organizing shout-for-shout cross-promotion groups and direct outreach to influencers. He converted his Instagram audience into a 26,000-person email list and launched an Instagram course at $397 one-time payment, generating $20,000-$30,000 in revenue in August alone. His strategy demonstrates how organic Instagram growth through peer promotion can be significantly more cost-effective than paid advertising.

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.

Stig Broderson left a six-figure commodities trading career in 2011 to pursue teaching and creating The Investors Podcast, inspired by Warren Buffett's philosophy of living authentically. Co-hosted with a friend in Maryland, the podcast has become the number one podcast in the world in stock investing, ranking #1 in its category with 17 competitors tracked. The show operates on a free model with no monetization yet, as Stig focuses on building value and maintaining editorial integrity.

Harry Campbell quit a six-figure aerospace engineering job at Boeing to build The Ride Share Guy, a leading content platform serving ride share drivers. Starting with a blog and podcast, he's grown to 450,000 monthly page views and 10,000 email subscribers, generating $25K/month through driver referrals, direct advertising, and an insurance marketplace.

John Lee Dumas built Entrepreneur on Fire, a daily podcast interviewing successful entrepreneurs, which generates over $300,000 annually with over 1 billion unique monthly listens. Recognizing a gap in helping his audience actually accomplish their goals (not just be inspired), he created the Freedom Journal, a physical goal-setting workbook priced at $35 with a $6.50 production cost, launching via Kickstarter with a partnership to donate $25,000 per funding level to pencils of promise charity.

Gimlet Media is a premium podcast network founded by Alex Bloomberg, a veteran of This American Life and Planet Money. The company produces high-quality narrative audio shows including Startup, Reply All, Mystery Show, Science Versus, and Surprisingly Awesome, generating over $1 million in annual ad revenue per show through CPM-based sponsorships well above industry standards ($50+ CPM vs. industry average of $20-30).

Chat with Traders is a weekly podcast launched by 25-year-old Aaron Feifield in January 2015 that interviews successful traders to help others learn trading. Starting from zero monetization but focused on audience growth, the podcast reached over 620,000 cumulative downloads in its first year with nearly 5,800 email subscribers, primarily driven by consistent weekly episodes and active Twitter engagement.

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.

Lila Zimmerman is a 19-year-old University of Maryland sophomore who built Fresh Fit and Fearless, a content-driven lifestyle brand centered on plant-based vegan eating. She grew her Instagram account from zero to nearly 15,000 followers in approximately one year (with serious effort starting at 6 months) through consistent quality content, strategic hashtags, and share-for-share partnerships. Her monetization strategy includes a $14.99 recipe e-book that has generated approximately $900 in sales, plus sponsored posts ($100 per two posts) and free product partnerships from 20-30 companies monthly.