57-Year-Old Proves It’s Never Too Late to Work for a Start-up

Published: May 18, 2015

Topics: Finance Job Search Technology Workplace Issues

Not all start-up employees are unshaven twenty-somethings who wear T-Shirts, sneakers, and jeans to the office. In fact, some are unshaven fifty-somethings who wear T-shirts, sneakers, and jeans to the office.

One such employee is Jerry Weiss, a former Citi and JPMorgan Chase banker who, at 57, is by far the oldest—and most experienced—employee of a New York-based start-up called Bond Street.

Through three decades, Jerry Weiss wore coats and ties to the offices where he managed credit risks at the nation’s biggest banks—a 50-story Citigroup tower in Queens and the 60-story Chase Manhattan Plaza in Lower Manhattan.

Now Mr. Weiss, who is 57, works out of a tiny two-room office in the Flatiron district, home of the start-up small-business lender he joined last year, where his younger colleagues make fun of his New Balance sneakers and “dad jeans.” His bosses at the start-up, Bond Street, are a pair of apple-cheeked Harvard graduates; and the average age of his seven colleagues is 28.

Weiss is no consultant or board member; he’s an essential employee of Bond Street, “one of 25 digital small-business lenders that rely heavily on data analysis in making decisions, aiming at a market with $300 billion in outstanding loans.” He was brought in for his vast experience that no one in his or her twenties or thirties could possibly have: Weiss has worked through numerous ups and downs in the economy. Here’s more of what he brings:

Weiss is bringing a distinctive quantitative approach to alternative lending. He has helped design Bond Street’s loan approval process to reflect automated inputs from credit bureaus, bank accounts, tax filings and QuickBooks online financial statements. The process also includes targets like expected profits of 1.2 times debt service.

Though a bit older than his colleagues, Weiss actually fits in well with the firm’s casual, laid-back culture.

[Weiss] attended Reed College in Portland, Ore., acquired a taste for the Allman Brothers Band and the Grateful Dead, and later earned a business degree at New York University. Though he wears T-shirts and sweaters to the office, as his colleagues do, he does have a thick gray beard. [And] Weiss has thrown himself into team building, manning the grill at a cookout to celebrate Bond Street’s first loan, arranging for water-skiing at the firm’s first off-site meeting at a borrowed Hamptons rental house last summer and helping with a recent paintball event.

Other start-ups take note: although there’s nothing quite like the youth and energy of a twenty-seven-old fresh out of one of the world’s top graduate schools, there’s also nothing quite like the wisdom and experience of a 57-year-old fresh out of one of the world’s largest corporations.

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