Brian Acton lost a small fortune in the dot-com bust and was rejected for jobs at Twitter and Facebook.
Now, the friends behind the hot mobile messaging startup WhatsApp are the newest tech industry billionaires.
Facebook this week bought WhatsApp in a stock-and-cash deal worth up to USD 19 billion and gave Koum a seat on the social network's board of directors.
Koum signed the Facebook takeover contract at the unused building where he and his mother once queued for food stamps in the Silicon Valley city of Mountain View, where WhatsApp is located, according to Forbes Magazine.
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His father did not make it to the United States, where the family sought to escape anti-Semitism and oppressive tactics of secret police.
"Jan's childhood made him appreciate communication that was not bugged or taped," Sequoia Capital partner Jim Goetz said in an online post.
"When he arrived in the US as a 16-year-old immigrant living on food stamps, he had the extra incentive of wanting to stay in touch with his family in Russia and the Ukraine."
A self-described trouble-maker at school, Koum had a job sweeping the floors in a grocery store. After his mother was diagnosed with cancer, they got by on disability payments, Forbes reported.
Koum learned computer networking from manuals bought from, and eventually returned to, a used book store, according to the account.
He enrolled in a state university in Silicon Valley and was working on the side with a computer security firm when he met Acton while on assignment at Yahoo in 1997.
Koum eventually chose Yahoo over college. When Koum's mother died of cancer in 2000, his mentor Acton stepped in with support.
Acton, meanwhile, reportedly lost millions investing during the famous dot-com boom that ended with an infamous dot-com bust.
Acton and Koum left Yahoo in 2007 and took a year off, exploring South America and playing the sport of Ultimate Frisbee, according to Forbes.