Drip Startups

A productized service (SWaS) business launched around the Drip email marketing platform, founded by Jeff Pecaro in response to a Twitter call from the Tropical MBA hosts who needed expert help implementing Drip. The business model capitalizes on the gap between Drip's power and the high learning curve that prevents many users from adopting it.

Brennan Dunn built Double Your Freelancing as a content marketing initiative to support his struggling project management SaaS (Planscope), but the educational content about freelancing business fundamentals exploded in success. The business now generates $900k+ annually (on track for $1.5M+) through high-volume, one-off course and workshop sales powered by personalized content marketing and sophisticated website personalization that adapts messaging based on visitor profiles.

ProdPad is a product management tool built by product managers for product managers. Founded in 2010 as an internal tool and launched publicly in February 2013, the company bootstrapped to ~$30K MRR through content marketing and organic search. After hitting a growth plateau in 2015, Jana and her team focused intensely on improving free trial-to-paid conversion by shortening trials from 30 to 7 days, gamifying onboarding with time incentives, and personalizing email flows—increasing conversion from below 3% to approximately 10%.