Why This Guy Gave Up His $500,000 Paycheck to Found a Startup

Ray Gillenwater and Adam Herscher have never met. But the two men are inextricably linked by a generational trend that will change the workplace forever. A shorter version of this story was posted on Inc.com: http://www.inc.com/cameron-albert-deitch/how-millennials-are-changing-the-workplace-permanently.html

Image: Courtesy Subject

To Adam Herscher (right), leaping from a corporate salary to bootstrapping your own business is more of an emotional risk than anything else–and that’s where millennials thrive.

Ray Gillenwater isn’t crazy for quitting a job where he earned $500,000 a year. He’s just a millennial.

Like others of his young, wide-eyed generation–those born between 1980 and 2000–work isn’t just about a paycheck. It’s also about constantly challenging yourself to make a tangible impact, says the now 29-year-old who left his job at BlackBerry two years ago to launch a startup.

“I look at what motivates me in a role as three main components,” says Gillenwater, who co-founded the San Francisco-based SpeakUp in August 2013 to help foster positive communication and collaboration in the workplace. “I always have to be learning new things. I have to feel like I’m making some sort of tangible impact; that I’ll be spending the majority of my waking hours on this mission to accomplish these things for this company, whether it’s my own or someone else’s. Because if I’m not, I feel like I’m wasting my time. And then the third thing is that I don’t really want to have to worry about money.”

Image: Courtesy Subject

Ray Gillenwater

So it’s hard to say his choice was easy. In 2007, when Gillenwater started at BlackBerry (after a day job with Verizon and night school at Cal-State Fullerton), his new boss told him if he performed well over the next few years, he could get placed anywhere in the world he wanted. That’s exactly what happened: After almost three record-setting years in regional sales, Gillenwater moved to Singapore, where he was able to expand BlackBerry’s annual revenue from $30 million to $1 billion in 18 months, the fastest growth in company history, he says. A year in, he took his boss’s job, managing distribution across Southeast Asia–but that only lasted eight months, he says, because he was promoted again to director of the Philippines. And eight months after that, he earned a double promotion, becoming managing director of Australia and New Zealand. He quit only four months later.

Even Gillenwater thinks his rapid ascent is unreal. “A lot of the time, it felt almost unwarranted. It almost felt like I was just getting lucky,” he says. But this isn’t a story about how to rise quickly in the corporate world (brutal honesty and good old-fashioned hard work, Gillenwater says). It’s about why a man who spent 180 nights of his first year in Asia at the Ritz-Carlton in Jakarta, a man who lived in a four-bedroom condo with a view of the Marina Bay in Singapore for over $7,000 USD per month, a man whose three-bedroom condo in Australia overlooked the Sydney Opera House on one side and Hyde Park on another would willingly leave that all behind.

Psychologists say it’s because this generation is so incessantly optimistic. As journalist Abby Ellin phrased it in a March 2014 Psychology Today article: “Millennials are simply trying to do better.” Other startup watchers suggest it has more to do with young people having fewer attachments than older entrepreneurs. In other words, they can risk launching even when 3 in four startups fail–because they don’t have a mortgage to pay or little mouths to feed. “A 20-year-old versus a 50-year-old has less financial risk,” says Chris Heivly, managing director at The Startup Factory, an accelerator in North Carolina. “So if I get a mortgage, two car payments, a couple kids, the financial risk of maybe not taking a salary for a year to do my startup is a much heavier burden than a 20-year-old who probably has a few grand stashed away.”

Some of it, according to Heivly, is a symptom of the entrepreneurial spirit. “The other part of why he did this is because he has to,” he says. “There’s not a choice. It was bubbling in him and he’s got to go do this. And whether that’s the desire to captain your own ship, to have the entire burden of the company on your shoulders, some of us enjoy that. I want to take this blank sheet of paper and make something amazing out of it.”

“I have to feel like I’m making some sort of tangible impact. Because if I’m not, I feel like I’m wasting my time.” — Ray Gillenwater

That’s something 33-year-old Adam Herscher, who wrote a LinkedIn post about why he left his $250,000 job at Microsoft in April 2014 to found a startup, can agree with. There are obvious reasons, Herscher says, for staying in a secure, high-paying job. Name recognition, for one, is powerful. Last year, at a restaurant, a waitress saw him using a beta pre-release version of a Windows phone. She freaked out, explaining that she loved her Windows phone and asking to see the new version (Herscher, though flattered, had to say no).

But during his time at Microsoft, Herscher kept noticing disconnects between product development and customer experience. Developers in Seattle never really communicated directly with customer service representatives in Manila. His friend in software engineering, Sean Andersen, noticed the same thing. But where some would have tried to fix the problem from within, the two men saw a broader market. Their startup, HasMetrics, was born.

The story of SpeakUp is similar. The higher Gillenwater rose at BlackBerry, the more he found his title was ostracizing. “When I first went into my role as managing director in Australia, part of the team was nervous to talk to me–and they didn’t even know me. It was just based on my title and the power that I had over their careers,” he says. This was problematic; Gillenwater needed as much feedback as possible to make an educated decision. He reached out to people he trusted, sharing the idea of software that could capture and curate employee input for ideation, and it particularly resonated with his eventual co-founder, Keith Barney.

Their parents would never do this. That’s the biggest proof that millennials are changing the workplace. Eli Herscher has dealt with 33 years of adrenaline spikes as his son made career choices he never would have dared. Where Eli went straight through college, graduate school and rabbinical school, Adam dropped out to work for two years without a degree. Where Adam has forgone job security and a healthy paycheck to chase that ever-elusive goal of making a bigger impact, Eli has been a rabbi at the same temple in Los Angeles for nearly 40 years. Eli’s jaw dropped when he read the oft-cited statistic that the average 26-year-old has changed jobs seven times since age 18. “If you’ve moved around seven times in 40 years, then people would wonder if you’re capable of holding onto a job,” he says about his generation. “They would think something’s wrong with you.”

Even coworkers only a few years over the millennial line find it difficult to fathom. Charles Chung, a telecommunications consultant whom Gillenwater brought over to BlackBerry from T-Mobile in 2011, is 37 years old, three years short of being a millennial. “I grew up with the mentality of get a good job, and obviously if you’re making a ton of money at this job, just baby it. Baby it and milk it and live the American Dream,” Chung says. “Ray is definitely from a different mentality where it’s not about the money. It’s not about the title. It’s about doing something that you’re passionate about, and the money will eventually come.”

It seems that passion outweighs the paycheck–particularly in the absence of risk. Herscher suggests that starting up is more of an emotional risk–and that, he says, is where millennials thrive.

He’s right. For all of the talk of a lazy and entitled generation, Gillenwater believes the easiest way isn’t always the best way. The man who would book business class flights with fully lie-flat seats now shares an apartment with his brother, drives a Toyota and has put himself on an international travel ban for the rest of the year. “I wondered how well I would deal with it,” he says. “And actually, I really enjoy my lean lifestyle.”

Then there’s Herscher, who seems incapable of living lavishly. His original intention when he quit Microsoft wasn’t to immediately jump into the startup game; he wanted to take six months to travel and clear his head first. After three weeks, his hands were shaking and he couldn’t sit still. “The idea of taking time off is really, really appealing,” he laughs. “But it doesn’t work for me.”

Both Gillenwater and Herscher want to create environments where millennials can experience stability and meaning. “One thing that still needs to be solved properly is how to make a big company operate efficiently and not like a big company,” Gillenwater says. “The challenge for me as the CEO of SpeakUp is when this company becomes massive and our employee base grows, how do I invent new processes and approach managing a team and a business operationally in a way that is conducive to the way people want to work, keeps people fired up and emotionally engaged in their job, and is an awesome place to be?”

Herscher’s goal with HasMetrics is almost identical. “I have to believe that there is a way to build a company culture that can give you that ever-exponential learning curve,” he says. “That can make it so that you don’t ever level out, so that you constantly are getting new experiences.”

It seems that passion outweighs the paycheck–particularly in the absence of risk. Leaping from a $250,000 salary to bootstrapping your own business is, of course, risky–or as Herscher says, “Irrationally so.” But to him, it’s the mindset that’s risky, not the action itself. In other words, if you think something is dangerous, it’ll feel dangerous. After all, even the most seasoned entrepreneurs experience failure along the way to success. Herscher suggests that starting up is more of an emotional risk–and that, he says, is where millennials thrive.

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