Time Slips

Mitch Russo founded Time Slips in 1985 with a partner, both in their mid-to-late 20s. The original concept was straightforward but soon became obsolete: create time tracking software that would let users deduct detailed records from their taxes. Both founders had quit their jobs and shut down other businesses to focus on this venture, betting everything on the idea. But shortly after launch, the IRS relaxed its rules on contemporaneous record-keeping, destroying their entire market overnight. They had a brand new product, zero customers, and no plan B.

Rather than fold, Russo and his partner pivoted. They realized that while tax tracking was dead, every business still needed to track time—especially knowledge workers like lawyers and accountants who bill hourly. They transformed Time Slips into time tracking and billing software. The pivot took three months, and the product was ready the day before Russo left to walk the floors at Comdex. This wasn't a polished launch; it was scrappy distribution.

At Comdex, Russo handed out the program to as many people as possible. This direct, physical distribution at a major trade show became the engine of early growth. Word spread through the accountant and legal community—industries where time tracking was painful and necessary. The product solved a real problem for their users, and the channel proved effective for reaching this niche.

The time tracking pivot worked. Russo grew Time Slips to $5.6 million in revenue by 1994, when Sage (a much larger software company) came calling. Russo faced an interesting choice: one buyer offered the asking price of $9 million with no strings attached; another offered half that but promised double the upside and a move to Dallas (tax-free Texas). Russo chose the latter, taking the deal at $10.5 million—exactly 2x his top-line revenue, which was unusually rich valuation for the era. He moved to Texas to run the division under Sage, and the business continued to grow, reaching $10.5 million in annual revenue by 1998. The tax calculation was tricky: Massachusetts considered it an installment sale, so Russo paid roughly $500,000 in taxes to the state even while living in Texas on his earn-out.

By 1998, Russo had transitioned out of Time Slips and decided Sage wasn't a fit for his style. He left operational software behind, moved back to Massachusetts, and pursued other ventures—VC investing (which failed during the 1999-2000 dot-com crash), furniture e-commerce (which collapsed in 2002), options trading, and eventually partnerships with Tony Robbins and Chet Holmes. Decades later, Russo returned to his roots in 2012, building a new SaaS company: an accountability platform to help people complete the training programs they buy. This time, he invested about $100,000 of his own capital and was preparing for beta launch.