What Works for Startups Like Yours?

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.

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.

First customers: Twitter outreach and partnerships with B2B companies (Ramp, DataRails) willing to partner for free initially to build audience

Reroute Lifestyle is a lifestyle and travel blog founded by Krista Aoki that helps goal-getters achieve financial freedom through remote work and online income streams. Starting in 2017 with zero investment, Krista grew the blog to 11,000 monthly page views and $1,500 MRR in 6 months through Pinterest marketing and content-driven storytelling. The business generates revenue through affiliate marketing, product sales, and services.

First customers: Amazon Affiliates commission earned within days of starting the blog

Starter Story is a content platform that interviews and profiles founders running businesses generating $10K-$100K+ monthly revenue. Founded by Pat as a side project in 2016, it grew to include a blog with case studies, YouTube channel, community, and products by requiring founders to publicly share their revenue numbers. HubSpot acquired the company, with the deal expected to close around the time of this interview.

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.

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.

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.

First customers: word-of-mouth from listeners telling friends about quality podcast content

Rich Roll transformed from a struggling entertainment lawyer and recovering alcoholic into a lifestyle entrepreneur by launching a podcast in 2012 to continue conversations started by his memoir 'Finding Ultra.' The podcast grew to approximately 500k+ monthly listeners (90-95% audio-only) by focusing on transformational storytelling and diverse guest interviews rather than gaming algorithms. His diversified business model includes podcast sponsorships (80-85% of revenue), meal planning subscription, cookbooks, public speaking, brand partnerships, and retreats, all anchored by the podcast as the primary growth engine.

First customers: Early adopter positioning - launched podcast when there was minimal competition and high listener demand for quality health/wellness content

John Lee Dumas built Entrepreneurs on Fire as a daily podcast interviewing entrepreneurs, starting in 2012. After struggling for 13 months with no revenue, the business hit $100,000 in month 13 and has since grown to generate approximately $180,000 annually from sponsorships. He's published 101 consecutive monthly income reports, becoming a transparency leader in the online business space.

First customers: Sponsorship deals from Midroll, a podcast advertising network that approached him in 2013 because of his high episode volume (30 episodes/month)

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.

First customers: Word of mouth, advertising, and media coverage from outlets like Flavor Wire and USA Today website