One night in late November 2021, Jay McKee, CEO of real estate tech platform Lessen, hosted 80 real estate VIPs at his home in Scottsdale, Arizona, for an annual soiree. He had something special to celebrate: his company's new $1.1 billion valuation. Sometime between the unveiling of grand cru wines, Pappy Van Winkle, and visits to the cigar cabana, McKee approached SMS Assist founder Mike Rothman, whom he'd known for 10 years. Reveling in Lessen's rapid growth, McKee blurted out, half in jest, "What if I buy your company?" Rothman laughed. "Jay," he said, "our revenue is 10 times yours. We buy you."
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