After selling HomeAway to Expedia for $3.9 billion, Ross Buhrdorf found himself at a crossroads. Like many founders after a major exit, he planned to take time off and finally do all the things he had postponed during years of building a company. But stepping away also created a new question: what comes next?
Ross explains that the answer wasn’t a perfectly crafted plan. Instead, it came from rediscovering a purpose that mattered to him—helping small businesses succeed. Entrepreneurship had always been part of his DNA, and he saw an opportunity to build something that could empower millions of founders.
The transition also came with real doubts. Could he raise money? Could he lead as a CEO instead of a CTO? His approach was simple: lean on the strengths he already had—communication, team building, and vision—and surround himself with great people. Sometimes the next chapter doesn’t start with certainty. It starts with stepping forward anyway.
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