Entrepreneur Vivek Ramaswamy announced Tuesday he’s running for the Republican nomination for president in 2024. The “Woke, Inc.” author joins a field that already includes former President Donald Trump and former Gov. Nikki Haley, R-S.C. The 37-year-old Ohio-native has never been elected to office but has founded a lucrative biotech firm. Ramaswamy laid out an agenda of decoupling from China, dismantling the “new climate religion” and repealing affirmative action laws. He’s not the first to attempt an official transition from business to the nation’s highest office. Here are some others who tried to move from the C-suite to a suite in the White House in this week’s Five for Friday.

#5: Andrew Yang

Andrew Yang received a surprising amount of attention during the 2020 Democratic Primary after appearing on high-profile shows and podcasts including the Joe Rogan Experience and the Breakfast Club. His campaign was energized through the use of memes and social media mobilizing his supporters, known as the “Yang Gang.” A key pillar of the Yang campaign was a universal basic income (UBI) of $1,000 per month. He said UBI would help as jobs were lost due to an increase in automation. All of the hype didn’t result in many voters though and he dropped out after two primaries. Yang went on to endorse Joe Biden.

#4: Carly Fiorina

Former Hewlett-Packard CEO Carly Fiorina gained some momentum in early 2016 Republican debates. The field was large, featuring governors, senators and another person from the business world that went on to become president. Fiorina had hoped her business acumen would make her standout from the field, despite being forced to resign her position at HP in 2005. But the early momentum stalled and she dropped out after poor showings in Iowa and New Hampshire. Fiorina also has the distinction of shortest vice presidential candidate in modern history after joining Sen. Ted Cruz’s campaign a week before he called it quits.

#3: Tom Steyer

It may be easy to forget about Tom Steyer’s 2020 bid for the Democratic nomination for president. The hedge fund manager turned climate activist was never able to gain traction despite sparring with Joe Biden and Bernie Sanders on the debate stage. Steyer technically survived four primaries but received no delegates before suspending his campaign. He spent around $250 million of his own money to fund the campaign, but at a current net worth of $1.5 billion, it was just a drop in the bucket.

#2: Ross Perot

The 1990s were a unique decade, and billionaire businessman Ross Perot was indicative of the quirky time period. In 1992 Perot launched an independent bid for president, facing off with Bill Clinton and George H. W. Bush. Perot ran on balancing the budget and an opposition to the North American Free Trade Agreement (NAFTA). He didn’t win any electoral votes in the election but is widely seen as one of the most successful third-party candidates of all time after receiving 19% of the popular vote nationwide. Perot’s persona also spawned arguably one of the best Saturday Night Live impressions of all time. He made another run for the White House in 1994, but couldn’t recreate the magic.

#1: Donald Trump

From the moment real estate mogul Donald Trump descended on a golden escalator to announce his candidacy for the Republican presidential nomination in 2016, he changed the landscape of the race. On packed debate stages, he pressed established politicians like Jeb Bush and Marco Rubio. He ended up running away with his party’s nomination and defeated Hillary Clinton in the general election. He was impeached twice during his time in office but not removed. He lost his reelection bid to Joe Biden in 2020 and is running for a third time in 2024.