Episode Details

When the Silicon Valley Bank crisis hit, Larry Roseman was en route to a tennis tournament in Palm Springs. “Literally getting on the plane and landing, and the whole thing sort of blowing up,” he tells us. What was supposed to be a weekend of matches quickly turned into a crisis response. “I was holed up in the hotel room for days,” Roseman recalls. With all of Thumbtack’s cash held at SVB, he and his team faced urgent questions around payroll and liquidity.

The experience became a turning point. “That was the catalyst for us,” he tells us, sparking a mindset shift from a revenue-growth-at-all-costs approach to one focused on profitable growth. Today, Thumbtack is EBITDA positive, reversing a -$60 million position to +$60 million within just a few years.

Roseman’s resilience is informed by a career that spans public accounting at Ernst & Young, investment banking during the dot-com boom, and operating finance leadership at eBay, where he helped spin off PayPal. These transitions taught him not just technical fluency but adaptability—especially in moving from fast-paced dealmaking to building diverse teams. “You’ve got to meet people where they are,” he says, emphasizing the importance of motivating individuals across working styles.

At Thumbtack, a nationwide home services marketplace, Roseman has scaled the finance team from five to 45 and implemented key financial sub-functions. He zeroes in on contribution margin and hire rate as core metrics—ensuring every dollar spent drives measurable value. “Ultimately, the P&L doesn’t lie,” Roseman tells us.