For Startup Generation, Wall Street Loses Its Luster

Wall Street’s dogma has long been that grueling hours would be matched with job security — and a fat paycheck.

Silicon Valley Innovation signage
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That’s what led Tristan Walker to the trading floor. The 27-year-old grew up on welfare in Queens, N.Y., in the shadow of Manhattan’s towering skyline. The promise of being able to get rich quick was Wall Street’s lure.

Because many banks did not recruit from Stony Brook University, Walker’s alma mater, he got his break in the back office, working in IT at Lehman Brothers during one of his first college summers.

But his eye was always on the trading floor, where Lehman moved him three years later, to trade bonds for six months in London. Upon graduation, he moved permanently into mortgage trading before helping start Lehman’s energy trading desk — then placing proprietary energy bets at competitor J.P. Morgan .

“I realized while I was on Wall Street that I wasn’t getting as much out of it as I thought I could,” Walker said in an interview. “I wanted to get as far away, both literally and figuratively, from Wall Street as possible.”

What he did take with him: The ability to assess risks, and how to manage them.

It was risky to leave J.P. Morgan and head west, where he enrolled in Stanford’s Graduate School of Business. It was also risky for him to send a blind e-mail to the founders of Foursquare, the location-based social network.

But he seems to have assessed them well, graduating from Stanford in 2010 and nabbing the role of Foursquare’s head of business development.

U.S. Army veteran Matt Thompson was already on the West Coast, working for Goldman Sachs , when the itch to ditch finance became too strong to ignore.

In the bank’s investment management unit in Los Angeles, Thompson was managing the fortunes of high-net-worth clients in order to service his own debt from Harvard Business School.

But when he got word that TroopSwap, a company he and Harvard classmate Blake Hall conceived a year earlier, closed a round of funding, he resigned immediately. The startup, which provides deals and an online home base for the military community, has now raised a total $3.6 million in total venture financing.

“As soon as I knew there was enough to support both Blake and I working full-time, I resigned,” Thompson said in an interview in the company’s new McLean, Va., headquarters. “But I wish I could get the time back that I spent on Wall Street.”

Silicon Valley, California
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Silicon Valley, California

Thompson said business school, hailed as the “farm system” for Wall Street, favored careers in finance or consulting, especially since the lion’s share of students graduate with more than $100,000 in debt.

For Robert Jones, a second-year student at Yale University School of Management, the path to Wall Street was paved by University recruiters as the path of least resistance.

“When you start as a first year in MBA, you see a lot of the structured recruiting process, especially in finance,” Jones said in an interview in New York City, where he was meeting with potential employers. “It’s just really tempting to start going right into that process.”

But after a year and half’s worth of “introspection” and decision-weighing, Jones is taking a leap of faith – choosing instead to line up a job with a New York or Silicon Valley startup.

“It was a lot of thinking about: where do I want to be in 5 years, what kind of job do I want to do, what kind of people do I want to be interacting with?” he explained.

For Jones, Walker and Thompson — and others of ‘Generation Startup’, those answers are unlikely to include Wall Street.

Follow Kayla Tausche on Twitter: @kaylataushe
Follow Jesse Bergman on Twitter: @JBergmanCNBC