Evan Frank, the new CEO of Context Travel, embarks on the latest of his entrepreneurial endeavors. After successfully scaling onefinestay, which was sold in early 2016 to AccorHotels for $170 million, Frank has joined Context Travel - a company that specializes in deeply researched tours in cities around the world.
Born with an entrepreneur spirit and having lived through various entrepreneurial ventures throughout his life, Frank decided it was time for him to start another venture. He shared how he wanted to marry career progression and fun, stating that working at board meetings in Barcelona and Berlin was much more enjoyable than working in Pittsburgh. This experience helped him understand the financing of startups.
Frank’s first attempt at a startup was BOX, a verticalized e-commerce brand selling men’s underwear, shirts, and socks. Though he eventually shut down this business, it brought him together with Greg Marsh, who had started another company called onefinestay. Frank agreed to join the company as its last co-founder.
onone of the largest antique markets in the world. The company would go on to raise about $81 million across several rounds of venture capital. It sold to AccorHotels, and Frank took the CEO position for a year during the acquisition and integration process.
Context Travel had been on Frank’s radar since 2010, as they had partnered with onefinestay recommending customers local tours in cities like Rome. After meeting Bennett and understanding the business better, Frank decided to join Context as its CEO while Bennett returned to his love of sailing.
Frank believes that starting a company and joining a bootstrapped one have different challenges. He explains that when you start a company, you own it or share ownership with your co-founders. However, there are serious challenges like not knowing whether the business is working during multi-year periods. On the other hand, leading a formerly bootstrapped business has taken enormous risk and time out of the business.
Frank considers himself two parts entrepreneur and one part operator, playing both roles in Context. He builds an executive team while learning about interesting places all around the world. His five-year-old self would likely approve of his current entrepreneurial journey.
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