Leadership & Productivity

US election: Four business leaders who ran for political office like Donald Trump

11 min read

07 November 2016

Former editor

With Donald Trump asking for the vote in the US election based largely upon his business acumen, we look at five other individuals who started in business before trying out politics.

US Election Michael BloombergMichael Bloomberg

As far as business leaders who tried their hand at politics go, Bloomberg is probably the most well-known and successful examples – albeit without running for president in a US election. The man behind his self-titled financial data and media company made billions of dollars before taking the view that politics was the logical next step.

Having started at a Wall Street investment bank, he used a hefty redundancy package to set up a business called Market Systems – looking to provide the New York money men the financial data he knew they were in need of.

That company became Bloomberg in the late 1980s, after which the likes of Bloomberg News, Bloomberg Message and Bloomberg Tradebook were set up.

Bloomberg’s first dabble with politics came in 2001 when looked to take over from incumbent New York mayor Rudy Giuliani, who was unable to run again after two terms in office. Voting in the primary for the Republican party nomination began on September 11, 2001, but was suspended because of the terror attacks. Having beaten Herman Badilo to the nomination, he received 50.3 per cent of the public vote – preventing Mark Green from winning for the Democrats.

Four years later and Bloomberg won the right to serve another term, this time upping his popular vote to 58.4 per cent – a 20 per cent margin. Such was his confidence as mayor of New York that he looked to extend the city’s term limits law and run for a third term in 2009. This effort was successful, and based largely on his claim that a man with business experience was key to helping the city through the aftermath of the financial crash.

When he finally gave up office in 2013, 12 years after first taking up the role as mayor, he left a $2.4bn budget surplus, a city reported after the 9/11 terrorist attack and 2009 financial meltdown and a reduced crime rate. However, the homeless population had grown, salaries had not tracked the increased cost of living and the tension between the city’s police force and minorities was beginning to pick up steam.

There had been speculation that Bloomberg would run in the US election for president in 2008, and again in 2012 and 2016. However, he has moved to reject such rumours each time and has subsequently backed Democratic nominee Hilary Clinton for president.

Keep reading to find out who else has tried to make it in politics, with varying degrees of success.

US Election Meg WhitmanMeg Whitman

With stints as CEO of eBay and Hewlett-Packard on her CV, Whitman has perhaps more right than most to declare her business and leadership experience puts her on solid footing when it comes to political roles.

Whitman joined online auction website eBay in 1998, when the business was only three years old. Spending a decade there as president and CEO, she oversaw growth to $8bn in revenues, the acquisitions of PayPal and Skype and recognition from the Financial Times as one of the 50 faces that “shaped the decade”.

Three years after stepping down from eBay, Whitman became a director at Hewlett Packard. A promotion to CEO came less than a year later. However, her achievements at HP are widely believed to not match those at eBay. She still sits as CEO of the newly-created HP Enterprise business, but her time there has been dogged by a falling share price and the highly-contentious acquisition of British company Autonomy.

Perhaps wanted to prove herself outside of the business arena, Whitman had made a move to become governor of California in 2010. Paying for the campaign personally, she spent nearly $150m in a failed campaign.

She came under fire after revelations showed she hadn’t voted in 28 years and for reportedly hiring an illegal worker as her housekeeper.

Perhaps stung by failing in the political arena, Whitman has not attempted to run for any other public office since – preferring instead to move back into the world of the CEO.

Despite previously backing Republication presidential candidates in the US election, despite her patchy voting record, Whitman has come out in public to support Hilary Clinton and donated to her campaign.

Keep reading to find out who else has tried to make it in politics, with varying degrees of success.

US Election Mitt RomneyMitt Romney

A prominent figure in the US private equity community, Romney has successfully run for governor of Massachusetts and unsuccessfully (twice) for in the US election for president.

A well-known Morman, Romney started his life after university by serving as a missionary in France. Having returned to the US he joined Boston Consulting Group and then Bain & Company. This experience in the management consulting world saw him move into private equity, with Bain & Company spin-off Bain Capital.

While he initially focussed on venture capital-type deals, it was his move into leveraged buyouts that characterised his time in private equity and provided fuel for critics when he did run for political office.

His first dabble in politics came in 1994 when he took on Ted Kennedy for a position in the US Senate. While he was successful in becoming the Republication candidate for Senator, he ultimately failed to beat a “vulnerable” Kennedy by only polling 41 per cent of the vote.

A stint as the CEO of the Salt Lake Organizing Committee for the Olympic and Paralympic Winter Games of 2002 was next on the CV for Romney, taking it from in a position of struggling to raising enough money to being with a surplus of $100m.

Back on the political track in 2002, when he took advantage of scandals involving the acting Republication governor Jane Swift to run unopposed for the position.

After four years as governor of Massachusetts, he decided to step up and challenge for the highest political position in the US – president. Going up against John McCain, Mike Huckabee and Ron Paul, Romney finished second in the primaries and had to put his presidential ambitions on hold.

After McCain failed to beat Barack Obama in the 2008 US election, Romney was back at it again in 2012. This time successful in the Republication primaries, he took on Obama – who was after a second term in office. Like Donald Trump has done during his campaign, Romney leveraged heavily his business experience at at time when the US was still recovering from the economic crash of 2009. While running Obama close, he only secured 47.2 per cent of the popular vote and again had to step back from politics.

Keep reading to find out who else has tried to make it in politics, with varying degrees of success.

US Election Carly FiorinaCarly Fiorina

Another new entry to the world of politics, Fiorina is the second in our list to have been CEO of Hewlett-Packard. She was there before Whitman, and was at the helm for six years until 2005.

Prior to that she had been a senior vice president at AT&T and a member o the US Space Commission. Upon leaving Hewlett-Packard, because of a forced resignation, Fiorina entered the political sphere and became part of Republication presidential nominee John McCain’s team in 2008. Her role centred mainly on fundraising, but she had to take a less public stance when she said on radio that none of the presidential candidates running for president in the US election were experienced enough to run a major corporation like Hewlett-Packard.

Leaving enough time between her chastening experience as chair of the fundraising committee, Fiorina rejoined the political sphere again in 2010 when she announced a bid for the Senate. As the candidate for California, she received endorsements from the likes of Sarah Palin and took on incumbent Barbara Boxer. She eventually lost by ten percentage points to Boxer, having contributed around $6.5m of her own money to the campaign.

Another four years passed before Fiorina was at it again, this time joining a swollen list of Republication candidates for the presidential US election. She used an appearance on Good Morning America to formally announced her candidacy, immediately going after Hilary Clinton.

However, her lack of appeal meant she never made it onto the prime-time debate slots, instead taking part in a separate one featuring outsider challengers. In March, Fiorina suspended her campaign and backed Texas senator Ted Cruz – after which it was announced she’d be his vice president running mate in a US election if he won the Republication nomination.