Substack Startups

Ariel Helwani transitioned from being an ESPN employee to building an independent media business focused on MMA journalism. He leverages multiple content platforms including YouTube, Substack, and merchandise (BreakingT) to drive revenue and audience growth. His strategy emphasizes niche expertise, audience building through controversy, and diversified monetization channels.

Lenny Rachitsky built a 1M+ subscriber newsletter and top 10 tech podcast that generates revenue through a freemium model on Substack. The content focuses on interviews with world-class product leaders and growth experts, offering concrete, actionable advice for building and growing products. He discusses the journey from starting the newsletter to adding a paywall and maintaining weekly publishing cadence.

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.