Walker Stapleton’s short and winding road from business to politics

The privilege and promise of Walker Stapleton, part 2

Walker Stapleton on election night in 2016 at the Doubletree Hilton in Greenwood Village. (Photo by Evan Semón Photography)

This is the second in a four-part series about Colorado’s Republican nominee for governor. Read part one here.

Walker Stapleton cites his business success as a reason to elect him governor. “I am fortunate,” he has said, “to have had a successful career in the private sector creating jobs, balancing budgets and building a successful company.”

The focus on his business background in ordinary years would be a sound strategy for a state that has proven it likes its leaders, particularly its Republican politicians, to come with some private-sector seasoning. But it’s a harder sell when running against a Democrat who began building multi-million-dollar businesses from the ground up when he was in college.

Stapleton’s career trajectory took a winding path. Upon graduation from Williams College, a private liberal arts school in Massachusetts, Stapleton took his master’s degree in business from the prestigious London School of Economics and then headed to New York and Silicon Valley in the midst of the dot.com revolution. After four years in two different jobs, he decided to go back to school. This time, he went for even more prestige, earning an MBA in 2003 from Harvard Business School.

After Harvard, he headed to Colorado where he landed a job at Lamar Companies, a private real estate acquisitions firm with an office in Denver. The job lasted a year when Stapleton left Lamar to join what became the family business. Four years later, he was running for state treasurer.

“Until I was in my early 30s I was focused squarely on having a business background,” Stapleton said in a May interview with The Colorado Independent. “All my education — my graduate degree, my master’s degree from the London School of Economics, my graduate diploma — all were in business-related activities and not political-related stuff.”

His first post-grad job brought him to Wall Street in his early 20s where he worked from 1997 to 1999 in the technology and banking division of the investment firm Hambrecht & Quist. From there he migrated to California’s Bay Area where he went into business development for Live365, the first radio community of independent DJs streamed on the Internet, where he worked from 1999 to 2001.

Live365’s then-chief technology officer, Peter Rothman, said in an email that he can’t remember how Stapleton landed the job. Back in those days, Rothman said, “Walker was a pretty young guy. He was a fan of the Grateful Dead and jam bands, but always wore a suit. We knew he was related to the Bush family and that was sometimes a joke around the office. I didn’t find him notably interesting.”

Steve Follmer, who at the time ran engineering for the company, remembered Stapleton as “genial, thoughtful, a bit bemused, perhaps even a bit awkward in large East Coast formal shoes.” He recalled Stapleton was hired “for his own qualifications, not his family background, which I only learned about after the fact.” One office memory he has involved Stapleton relating a story about a visit to the Bush family Texas ranch, wandering down into the kitchen in his pajamas, then “beating a retreat when he realized there was a tour coming through the house.”

Stapleton ran into the law during his time in San Francisco, pleading guilty to drunken driving after a June 1999 car accident. He “smelled of alcohol,” was “loud and belligerent,” and drove away from the scene, “initially refusing to stop even after officers arrived,” according to The Denver Post, which obtained the police report from Stapleton during his first run for treasurer. A hit-and-run charge was dropped, and he eventually did community service. A decade later, he told a reporter that acknowledging his DUI during a debate felt like “being forced to eat a doo-doo sandwich.”

Stapleton told The Colorado Independent in May that although he regrets the mistake he made in his early 20s, he doesn’t consider it a political liability. “If that’s the best that they’ve got … bring it on,” he said.

After his stint at Live365, Stapleton headed back East for Harvard Business School where he earned an MBA in 2003. From there, he moved to Denver and worked for about year at Lamar Companies, a private real estate investment firm. As director of real estate acquisitions, he was tasked with finding shopping centers, office buildings and other commercial properties on the West Coast for potential purchase.  

Lamar CEO Mark Kalkus describes Stapleton as a diligent worker who found plenty of inventory, but said the company didn’t end up buying any because properties were cheaper on the East Coast. “We just weren’t getting anywhere … He was frustrated not finding projects, we were frustrated we couldn’t buy anything,” said Kalkus, who supports Stapleton and has donated to his campaigns.

In 2004, Stapleton worked as a consultant for Castle Keep Realty of Denver, a private real estate firm, according to corporate filings with the Securities and Exchange Commission. Those filings also say he was a founding principal of Convergence Capital Partners, a private real estate opportunity fund that made investments in Eastern Europe.

Not long after he moved to Denver, he met Jenna Bertocchi, a magazine marketer, at a bar during a visit to New York City. He proposed at Walker’s Point, the Bush family compound in Maine, hiring a lobster boat with a “Marry me” banner. The couple wed at the Bush property a year later, in 2006, and nearly 700 protesters showed up near the church before the service, demonstrating against the war in Iraq and then-President George W. Bush, who attended the ceremony.

By the time of his marriage, Stapleton had upped his business credentials by being named chief executive and chief financial officer of Sonoma West Holdings in 2005. His family owned nearly half the shares of the California company he often notes was publicly traded on the NASDAQ.

His father, Craig Stapleton, a prominent Connecticut businessman and an ambassador during the George W. Bush administration, had joined the board of the former dehydrated fruit business in 1995. He built up his stock as it sold off its fruit operations to focus on managing and renting a handful of warehouses and light industrial buildings in California’s wine country. As CEO, Walker Stapleton would run the company from Denver with the help of a local property manager.

When Walker Stapleton was made CEO in 2005, company directors cited not just “his family’s long-term involvement in the management of the company,” but, among other things, “his extensive experience and expertise in finance and in the real estate industry,” according to corporate filings sent to company investors. That experience spanned six years, including his stints on the West Coast and in Denver.

Stapleton started out earning $96,000 per year in salary, but ultimately earned $431,000 in 2009, including a $210,000 salary, a $185,000 bonus, and $35,000 in other benefits, corporate filings show. That year, Sonoma West posted profits of $1.9 million on revenue of just under $3.7 million, both small figures for a company with public investors.

“When we were shareholders, and Walker was CEO, (Sonoma West) was not a significant enterprise,” said money manager Kent Rowett, a Californian, whose firm Leeward Capital owned more than 7 percent of the company at the time. He described Stapleton’s father as “the real economic engine of the company.”

As Rowett tells it, Craig Stapleton invested Sonoma West’s cash in MetroPCS shares when the wireless phone service was growing rapidly. The elder Stapleton sat on the board of MetroPCS in 2004. “He seemed to be well connected,” Rowett said.

Walker Stapleton declined multiple interview requests for this story. Craig Stapleton did not return messages left with an assistant at his office.

New kid on the GOP block

Walker Stapleton was settling into life in the Denver area as a new husband, new father and new CEO when he began flirting with a run for public office in 2009. It was 17 years earlier that he had told his college newspaper of his itch to one day get into politics.

The 30-something with a double-whammy political name had joined civic groups, charities, and social circles with financiers and Republican heavy-hitters looking for winnable new leaders. The state GOP had some young rising stars on its bench, but its top-ticket candidates that election cycle ended up with serious flaws.

“We weren’t overrun with young interesting guys — or ladies, for that matter — in the Republican Party then who wanted to run,” said Sean Duffy, a public affairs specialist and former deputy chief of staff for Colorado’s last GOP governor, Bill Owens.

Stapleton was more than just a young, interesting guy. He had the name, the resume, the connections needed to be a viable candidate. The deliberative nature of the legislature wouldn’t suit his temperament, he told The Independent in May, so he eyed an executive branch role — the office of state treasurer. The job appealed to him, he said, because of his education and experience in finance. It also offered a potential launching pad; two former governors, Roy Romer and Bill Owens, had both been state treasurers.

No Republican had yet officially announced a bid to take on incumbent Treasurer Cary Kennedy, a well-respected Democrat who had shown a steady hand in protecting taxpayer money during the recession. In April 2009, Stapleton announced his candidacy, armed with a list of 30 big names and business people who supported him for the 2010 election. They included former U.S. Secretary of Veterans Affairs Jim Nicholson, El Pomar Foundation CEO Bill Hybl, and Gallagher Enterprises CEO Charles Gallagher.

Stapleton did not clear the field, and the early favorite in that year’s GOP primary race was J.J. Ament, now the CEO of the Metro Denver Economic Development Corporation. Ament had consolidated Republican establishment support as well as Tea Party backing, and he crushed it at the 2010 state assembly.

But Stapleton — who sidestepped the assembly process by paying signature gatherers to help him petition directly onto the ballot — out-fundraised Ament and campaigned hard. Stapleton’s early donors included George W. Bush and other family members, along with high-finance figures from New York to Texas, and some of his former Harvard Business School classmates. They also included heavy-hitters in Colorado. Pete Coors and John Elway chipped in. So did conservative Denver billionaire Phil Anschutz and Larry Mizel, a wealthy homebuilder and powerbroker. Robin Pringle, a vice president at Liberty Media who is now married to Democratic Gov. John Hickenlooper, was an early donor and is a close friend of Stapleton and his wife. Stapleton raised more than $500,000 and put at least $115,000 of his own money into the GOP primary race for treasurer.

He tagged Ament as a “debt-bond salesman” who was too closely tied to state government. And he cast himself as a political outsider and job-creating businessman. 

Stapleton took on water in the race when he said in a TV debate that he wouldn’t oppose voter-approved tax hikes to help shore up the state budget. Ament stuck with the party line by flat-out objecting to new taxes and fees, which stoked suspicion about his opponent’s conservative credentials. Stapleton ended up narrowly beating Ament in the primary, aided by his hard work and money, impressing fellow Republicans along the way. “Walker was in a lot of ways seen as an outsider,” said Jesse Mallory, who managed Ament’s campaign and now runs the state chapter of the Koch-backed Americans for Prosperity, a national group that is helping Stapleton’s gubernatorial bid this year.

In the general election, incumbent Kennedy hammered Stapleton with ads about his DUI, calling him “reckless” and “irresponsible.” Asked in a general election debate whether he had his sights on a higher office, Stapleton said, “I’ll never become a professional politician. I’ll serve my time, speak from my heart, and then go back to my career in the private sector.”

Stapleton narrowly ousted Kennedy in what became the most expensive race for treasurer in state history, with each spending more than $1.5 million.

It turned out that 2010 was a wave year for Republicans. Yellow “Don’t Tread on Me” flags fluttered at political rallies, part of the backlash to President Barack Obama’s first term and the advent of Obamacare. Statewide, Republicans turned out some 100,000 more voters than Democrats.

“If there was a year to run for statewide office as a Republican, 2010 was the year,” said then-Colorado Republican Party chair Dick Wadhams, who had run campaigns for an older generation of GOP bulls such as former U.S. Sens. Wayne Allard and Bill Armstrong.

Just six years after moving to Colorado, Stapleton leapfrogged to a top spot in the GOP heirarchy without tying himself to Colorado’s Republican old guard nor rising through the ranks of conservative-issue politics, local government or the legislature. He didn’t have a ready-made political base of evangelicals, gun rights groups or the Tea Party.

Call it good timing or privilege, hard work or political promise, but with a combination of all, Stapleton had made a name for himself early in Colorado.

Financial journalist David Milstead contributed to this report.

CORRECTION: An earlier version of this story misstated the location of Walker Stapleton’s first post-grad job.


  1. Yep…Ol’ Walker is the poster boy for being a Magamoron….trump proved that government, can not and should not be run like a company, nor should government be run by a greedy, and corrupt republican…just say no to any and all republicans….they are only out to destroy our way of life…

  2. Vote, folks. Mail in your ballots. A majority is not enough anymore. Colorado can show the nation that a sea change has taken place here.

    We still have some purple polka dots, but a swing state we are no longer. Coffman and Walkkker are going to be excellent examples of this new skin.

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