How I Took a Vacation and Launched a Company

Andy Hill went on vacation in Cuba in 2018, and while the beaches were great, he’s not one to lounge. Instead, Hill went around saying “¡Hola!” and–with the help of a friend who actually speaks Spanish–peppering locals with questions about business opportunities. He is, after all, a guy who has founded 12 companies since his college days. (He also runs those startups while holding down a day job as chief revenue officer for City Furniture, a nearly $1 billion company near Fort Lauderdale, Florida.) All of which explains why, after he kept hearing “software engineering” in Cuba, Hill launched a firm to staff U.S. companies with Latin American software engineers. He named it Siono, riffing on a recurring–and somewhat rhetorical–question from that trip: “Want another beer? ¿Sí, o no?” The refrain has become central to the company’s growth culture, with Hill and team continually asking, “Are we the best partner they’ve ever had? ¿Sí, o no?” With $5.5 million in revenue in 2021, the Delray Beach, Florida, company appears to have its answer. –As told to Steven I. Weiss

Others have hobbies like skiing; I start companies. I devote 50 hours a week to my full-time job, but I have breakfasts, I have dinners, I have weekends, and that’s when I grow my company–that’s my hobby. I build companies because I just can’t not. I know there are better ways to make money, have a stronger work-life balance, or leave a more lasting impact. But for me, I love bringing things into the world and empowering my team to grow. That’s what drives me.

My second startup ended poorly. When I was 23, I left a job to launch a social-good startup that got through a seed round and a Series A round, but then the Series

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