The Doyle Report: Whatever Happened to the Class of 2008?

Ten years after the Great Recession began, we take a look at the careers of professionals it affected.


April 12, 2018

16 Min Read

As a young man growing up in Michigan, Aaron Leveston dreamed of better things. One of seven children, Leveston wanted a nice car, a fine home and a family that enjoyed the carefree life of financially secure people.

More than simply pine for better things, Leveston put a tangible plan in place to attain them. He worked hard to achieve good grades. He saved money, volunteered and helped around the house. After being accepted to Western Michigan University in Kalamazoo, Leveston arrived on campus determined to make his mark. There, he zeroed in on the major that he believed had the potential to provide him everything he dreamed of — finance.

As he entered his junior year of college, Leveston imagined himself trading futures at the world-famous Chicago Mercantile Exchange. As 2007 gave way to 2008, everything seemed to be going according to plan. But life intervened. Six hundred miles to the east in New York, trouble was brewing on Wall Street. A crisis in the housing market revealed massive exposure to subprime loans by securities brokers and wealth-management firms. In March, the fabled trading house of Bear Stearns collapsed. Next fell Lehman Brothers. More banks and mortgage underwriters followed.

By the end of the year, it was clear the U.S. economy was heading into a deep, prolonged recession. Its ultimate toll was staggering: 2.5 million businesses collapsed, 4 million homes fell into foreclosure and 8 million jobs were lost.

As for Leveston, his dream of making a nest-egg in securities cracked the moment “finance” became a dirty word. While his plan unraveled, his ambitions remained intact. Instead of finance, Leveston eventually found his way to technology, where he works today. It was a circuitous route to success that he hadn’t planned on taking. But 10 years after graduating at one of the most inopportune times in American history, Leveston believes his career is better for it.


Aaron Leveston

Aaron Leveston

So do many others from the era. The long route to success, they say, taught them grit, humility and patience — qualities that have made them better professionals than what they might have otherwise become.

This is the story of the Class of 2008 and 2009. It chronicles how several young men and women of that era fared after joining the tech industry 10 or so years ago. While their experiences differ, they tend to agree on one thing above all else: For all the talk of being pampered millennials, they share a bond knowing that they endured one of the toughest job markets in U.S. history. Plan B for them wasn’t a consequence of misdeed or missed opportunity, but a harsh reality foisted upon them by the misfortunes of others.

Here’s how several coped in the aftermath to become the next generation of young tech standouts.

From Special K to 401(k)s and Beyond

People react differently when their dreams fall apart. Disappointed that finance was a dead end in 2008, Aaron Leveston took at job Kellogg’s in Battle Creek, Michigan. His first assignment was with the food giant’s Diversity and Inclusion team. Promotions quickly followed.

As much as he valued Kellogg’s, Leveston didn’t see himself spending his career selling Special K. Unsure what to do next, he took off nearly an entire year of work to help raise his two daughters. Fortunately for he and his family, his wife, Alisha, had a well-paying job working as an engineer in Chicago. Instead of rising the corporate ladder, Leveston soon found himself climbing the one at the local playground instead.

With his girls, Leveston played with dolls, watched Barney and read countless bedtime stories. While he enjoyed his time spent working as “Mommy Dad,” he longed to put on a suit and return to the business world. When the time was right, Leveston started applying for jobs. His first gig: selling 401(k) retirement plans to small businesses for John Hancock Life Insurance Co. While he hated the insurance racket, Leveston discovered that he loved sales.

Out of the blue, Leveston received a job offer from Oki Data. The Japanese tech giant wanted him to sell its multifunction printers. At the time, Leveston knew next to nothing about office technology, but the pay was better. Once he signed on, he proved to be very adept at winning over customers. Recognizing Leveston’s superior people skills, his boss purposely assigned him to regions where Leveston, a young black man in his late 20s, stood out. Think Kansas, Nebraska, South Dakota and more.

“Oki Data at the time had a U.S. market share in the single digits,” Leveston recalls. “My manager figured that we had to stand out somehow, so I fit the bill.”

Everywhere Oki Data sent Leveston, sales and market share grew. It happened in small towns, school districts and old-line businesses in places like Kansas City, where sales were conducted over a steak and a glass of bourbon. Leveston was all for it. He found that once he talked about business efficiency and customer service, cultural differences with his clients faded away.

After nearly three years with Oki Data, Leveston pined for more. That meant cloud, AI and other innovations more sophisticated than printers. About that time, RingCentral, a provider of cloud-based unified communications services, came calling. While Leveston didn’t necessarily understand the company’s technology right away, he absolutely knew it could help small businesses improve their competitiveness.

Since joining RingCentral as a regional channel manager in October 2015, Leveston has made the company’s coveted “Presidents Club” for top salespeople and been promoted to the position of national accounts manager. He achieved success, in other words. Leveston now drives an Audi and sends his daughters to a private school. He’s also become a sought-after speaker. (In addition to helping out with the Channel Futures Think Tank, Leveston is one of the founding members of Channel Next, a new outreach group for young workers set to debut at the Channel Partners Conference & Expo, April 17-20 in Las Vegas.

Today, Leveston is as interested in giving back as he is in moving up. Since 2015, he’s served on the board of the Open Door Health Center, an Elgin, Illinois-based care provider that serves underprivileged communities in the Fox Valley, Illinois, area. He has also worked with a local chapter of the NAACP and a local economic empowerment group known as Advance Together.

When he stops and ponders his fate, Leveston feels blessed, even when it comes to the disruption and disillusionment he felt at the time of the recession.

“I have no doubt I’m a better man for it. I remember how hard I worked after it hit, and how much I struggled,” he says. “One of the things it taught me was gratitude. Take my former manager at Oki Data. We’ve lost touch a bit. But I’ll never forget the doors he opened and the lessons he taught.”

After the Bow Breaks

If you ask technology business owners what they struggle with most today, many will tell you it’s an inability to find enough skilled workers to keep up with demand for their services. Today, there are thousands upon thousands of open positions in technology, despite the industry’s latest hiring binge. In the past 12 months, 194,000 new jobs were added in tech, according to CompTIA’s 2018 Cyberstates study. For perspective, the figure is more than the total number of people who work in steel and aluminum production in the U.S. combined.

But it’s only a fraction of the number of positions that the industry will need to fill.

“When factoring in the need to replace retiring or career-change workers, the total potential tech workforce need will exceed 1.2 million through 2026,” says CompTIA.

That’s a far cry from a decade ago when the wheels of the tech economy started to come off. By the time the market stabilized, Hewlett-Packard was a fraction of its size, Dell and EMC were struggling and Cisco was shrinking by the quarter.

Channel companies were similarly hard hit. Estimates vary, but thousands of channel companies are believed to have succumbed to the downturn. Though the industry fared better than housing, banking, tourism, real estate and other industries, it struggled to hire workers for the opposite reason that it does today. Back then, there were simply too few jobs to go around.

At the height of the recession, there were as many as 23 million U.S. workers looking for jobs. This includes 12.3 million that were out of work altogether, and 8 million-plus who were underemployed, according to the Economic Policy Institute.

What made things acutely painful for the graduates of the classes of 2008 and 2009 was the amount of student debt they had racked up while pursuing their studies. Millions of students had debts accruing interest by 2009, some topping more than $100,000.

Thanks to student debt, members of the millennial generation buy fewer homes and cars than generations before them. They also tend to open new businesses at lower rates. Among millennials I spoke with, most expect the ripple effects of crushing debt to stay with them for years to come.

That said, they have had to go on with their lives just the same, albeit with the burden or sense that they were misled about the Great American Dream. Go to school, find a job, buy a house, get married and have children? That’s not exactly the path that many members of the classes of 2008 and 2009 could pursue, at least not at first.

Picking Up the Pieces

“It does feel like there were promises made to my generation that didn’t come true. But you still have to make best of what you get, and that’s what we are doing.”

The above quote comes from Rory Jackson, a 2009 graduate of ITT Technical Institute. Jackson lives in Las Vegas, one of the cities hardest hit by the Great Recession.

When Jackson completed his bachelor’s degree in 2009, the best tech job he could find in Las Vegas paid just $2 more per hour than the service job he held before racking up $50,000 in student debt. With the Las Vegas economy reeling, Jackson moved from tech job to tech job until he was hired by Business Continuity Technologies (BCT) of Las Vegas in October 2013. BCT is a managed services provider that has served greater Las Vegas and beyond since 1984.

At BCT, Jackson found a professional home. Since joining the company, he has poured his heart into his tech career. In addition to serving as the manager of technical services for BCT, Jackson has also served as an executive council member for Association of Information Technology Professionals and vice chair for the Future Leaders Executive Council Member at CompTIA.


Rory Jackson

Rory Jackson

Still, Jackson occasionally wonders about what his life would be if the bottom hadn’t fallen out of the economy in 2008. Prior to joining the technology industry, for example, he worked in the hospitality field, which had been booming. By now, Jackson says, he would likely be working as a hotel manager making nearly as much money as he does today.

“The only difference is I wouldn’t have racked up the $50,000 in debt that I did studying information security,” he says.

Though not bitter, Jackson does think about the “road not taken” now and then on his weekly motorcycle rides up Mount Charleston on his Harley-Davidson Road Glide.

Another channel professional who sometimes ponders his journey is Bryan Reynolds.

Like Jackson, Reynolds graduated a year into the recession in 2009. A music major and University of Illinois band member, Reynolds dreamed of teaching music. But job openings for would-be teachers were few the year he wrapped his studies.

After applying for several jobs, Reynolds landed a part-time position in a small Illinois town. To make ends meet, he worked as a substitute teacher and as a cashier at a local Walmart. As much as he loved music and teaching, he found the ordeal a grind. So in 2013, Reynolds moved to Chicago and resigned himself to take whatever job he could find.

That led him to TBI, a master telecom agent steeped in telecommunications sales. At the time, Reynolds had little idea what the channel was or how it functioned. But the company liked his energy and people skills, so it assigned him to roll cold calls from within its call center. Reynolds concedes he was terrible at the job. But a manager recognized that his communications skills could be put to greater use. He tasked Reynolds to help on-board new agent recruits. While it wasn’t music, the job did require a lot of educating.


Bryan Reynolds

Bryan Reynolds

Reynolds took right to it. He has worked at TBI ever since, serving in a variety of roles after several promotions. When he reflects on his career, he doesn’t focus on the negatives. He notes that he can still play music whenever he wants; plus, he can now pay his bills to a degree that simply was not possible before.

As for his friends, fewer than half, he says, work in their chosen field. And only a fraction of his former bandmates have full-time jobs in music. One turned to banking. Another does social-media work for corporations.

“It’s not the dream we were sold or even the one will eventually pay for. But I am very happy with the people I work with,” says Reynolds.

A Shark in a Pink Bow

In addition to those who found stable careers at growing tech companies, the class of 2008 and 2009 produced a number of entrepreneurs who decided to put their careers into their own hands. Take Dani Miles, founder and CEO of Impressi Marketing, a marketing services company that works with the likes of Dataprise, a Rockville, Maryland, managed service provider (MSP), among others.

Midway through her studies at the University of Miami, the downturn seized control of the economy. At the “U,” the economy soon pervaded almost every aspect of campus life before graduation. It influenced how much students spent on clothes, cars and apartments. It curtailed some partying and spring-break vacations. It also influenced which majors students pursed.

With influence from her parents, the dance-loving Miles ditched any flirtations with the arts and humanities. Instead, she followed in the footsteps of her brother, who graduated from the University of Miami. Despite widespread layoffs on Wall Street, he landed a job at Goldman Sachs. Hoping for similar luck, Miles chose finance as her major.

With pluck, Miles landed a part-time job after graduation at Convergent Wealth Advisors, an investment advisory firm based in Washington, D.C. Hoping for something more stable, Miles lobbied hard for a full-time position, though Convergent had no openings. She recalls practically stalking the company until it created a job for her.

“I’ve been told that I am a shark with a pink bow. I come off as nice girl, but if I want something, I will try my hardest to get it,” she says good-naturedly.

After four years at Convergent, Miles began to ponder new horizons. Having lived on the East Coast her entire life, she looked west to Los Angeles. After a year there, she accepted a position as marketing manager at Sony Pictures Entertainment in Culver City, California. Miles joined the production house immediately after the massive North Korean cyberattack against the company, which was launched in retaliation for the release of the film, “The Interview,” starring James Franco and Seth Rogen. The film parodied the relatively new administration of North Korean leader Kim Jong Un, and the North Koreans were pissed.

The cyberattack ground Sony Pictures Entertainment to a near stop — so much so that Miles had no idea if she had a job after accepting the company’s initial offer. In the days leading up to her start at the company, no one responded to Miles’ email inquiries or phone calls.

Hoping for the best, Miles showed up to work on time on her first day. From the get-go, it was apparent that the company was in the throes of chaos. The period of tumult turned out to be a blessing in disguise. Instead of spending hours toiling away on low-level projects and email, the curious circumstances demanded that she spend time talking to peers and bosses with whom she ordinarily would have had limited interaction. She gleaned a great deal about the entertainment industry as a result, and corporate bureaucracy too. Along the way, she learned volumes about herself.

“Who else can claim to have benefitted personally from the regime of the North Korean dictator?” she jokes.

While Miles appreciated her time at Sony Pictures Entertainment, she found the workplace political and somewhat stifling. Itching for more control over her life, she decided to launch her own marketing-services company. After a year of planning, Impressi Marketing made its debut. Initially, Miles offered clients a standard set of marketing services, but then she recognized an opportunity to differentiate her firm. Rather than offer a traditional package of marketing services for a monthly fee, Miles positioned her company as a media connector that would only bill clients when it garnered them media attention. The move proved to be a shrewd one that no business owner could say no to.


Dani Miles

Dani Miles

With momentum building, Miles persuaded her husband, Larry, an L.A.-based business owner, to move to Park City, Utah. Park City is a destination resort with a bustling tech community. It’s also a place where Miles visited time and again on vacation with her family during her youth. (Full disclosure: I live in Park City and have met Miles and her husband socially.)

Today, Miles and her extended network of marketing pros have as much as work than they can handle (though they are always looking for more). In addition to her tech clients, Miles helps restauranteurs, insurers, construction companies and health-care providers boost their image.

While Miles enjoys the success she has attained, she has not forgotten early years of sacrifice. For four years after graduating from college, she lived at home with her mother in Bethesda, Maryland. She worked long hours and saved as much money as she could. So did her friends and peers. Some worked nights in restaurants. Some worked mornings as baristas. Unable to find meaningful work, others returned to school for additional study.

For all the jokes and doubts thrown their way, the millennials, Miles says, are good stewards of the economy. And they are grittier than they get credit for. When they entered the workforce beginning in the late oughts, for example, the up-and-coming millennials stepped into many workplaces that were deep into decline or disarray. The first jobs many held demanded that they navigate the workplace without advice or instruction due to workforce reductions, management crises and strategy shifts. Miles recalls being forced to make decisions that ordinarily would have been made by managers five or 10 years older than her. But because many were laid off in cost-cutting moves, she and her peers were drafted into decision-making roles at an early age.

Snowflakes? Slackers? Lifestyle junkies? These descriptors don’t ring true to Miles, or many from her generation. Not now, anyway.

“Millennials are known to prioritize ‘happiness’ and other factors when choosing a career. But that’s often after putting in time in the workforce. When many of us began our careers, we took jobs that were tough, often above our heads, and that involved cleaning up messes that were not our making. We did our best. We worked our butts off. And the economy prevailed. Was it us? Not entirely. But we played more of a role than people know,” Miles says.

About the Author(s)

Free Newsletters for the Channel
Register for Your Free Newsletter Now

You May Also Like