Dolly

Chad Whitman started his entrepreneurial journey while working at a social media agency around 2012. He noticed himself spending most of his time doing Facebook analytics and reporting rather than actual social media management. The Facebook News Feed algorithm frustrated him, but more importantly, he realized existing Facebook analytics tools were inadequate. Instead of pushing for better tools within the agency, he and two co-founders—Jason Norris and Kelby Han—decided to build their own solution.

Edranck Checker took about a month or two to build the initial prototype, which attracted roughly 10,000 free users including some big brands. A more professional version launched in 2012. The team had worked on the project for about a year and a half while still employed at the agency before Chad quit his $50-60K salary to go full-time. "My boss told me I could make over a million dollars at an agency," Chad recalls, "and I said, screw that, I'm going to do my own thing."

Their first day of sales was humble: five customers at $30/month each, triggering a "cha-ching" notification sound that eventually had to be disabled because sales were coming in too fast. Within two months, they hit $20K MRR—roughly breakeven for their $25K individual salaries. They bootstrapped entirely, reinvesting revenue back into the product rather than raising venture capital.

Edranck Checker grew steadily to $60K MRR at its peak. When acquisition conversations began with potential buyers like Simply Measured and Social Bakers, Chad realized he didn't understand his own business metrics—churn, LTV, CAC. Nathan Latka's tough questioning during due diligence forced him to learn this framework, which ultimately strengthened his negotiation position. The exit math was straightforward: $60K MRR × 12 months × 4x multiple = approximately $2.8M, with a favorable churn adjustment because Social Bakers saw oscillating customers (churn-to-free-to-paid) as upsell opportunities rather than pure loss.

After the Social Bakers exit in summer 2014, Chad co-founded Dolly with the same two co-founders from Edranck Checker. Recognizing that other gig economy platforms (Uber, Postmates, Instacart) were all competing for the same drivers in the same vehicles, Chad identified an untapped asset: pickup truck owners. Dolly uses a 20% take rate model on moving jobs and has since expanded into hauling and delivery partnerships. The company raised $1.7M in seed funding and $8M in Series A (valuation ~$50M range), positioning itself as a differentiated player in the gig economy by controlling a unique labor source.