The Rebel Billionaire (2004)

In this one-season, elimination-format reality series, adventure-seeking billionaire and Virgin Worldwide founder, Sir Richard Branson, led 16 billionaire-hopefuls around the world for six weeks. The contestants faced tough business-related and physical challenges, with one ultimately proving his or her mettle as the worthy successor to Branson’s global empire. 

Editor’s note: Maclean was not available for comment. The following essay appeared in the Princeton Alumni Weekly Feb. 23, 2005:


My inner rebel: What whitewater rafting in a crocodile-infested river has to do with business — and life

By Heather Maclean ’94 

For reasons I don’t quite understand, I am a television casting director’s dream. I walk in the door, they gush over how “real” I am, and I’m cast. 

Unless you want to be an actress or a spokeswoman, this is a rather useless trait. My stints on Road Rules, STUDS, and The Price is Right netted me not-so-fabulous prizes, including a year’s supply of jam. I did get to parasail, spend a week on Catalina Island, and be the subject of an actual bar brawl in Tijuana between Navy men and my “date,” but I didn’t really learn anything about the world or myself. 

Through the years, as game shows gave way to reality television and the prizes got bigger, I have been asked by friends and family to dust off my casting costume and nab a spot. 

I knew I could never navigate the nastiness (or boredom) of Survivor. I love adventure, but not stress, so The Amazing Race was out. Everyone thought The Apprentice was a perfect fit, but I have no desire to work for Donald Trump. 

I’m an entrepreneur who left the corporate business world to drive my own destiny. Five years at Disney and two as founding partner of an Internet company cured me of my corner-office dreams. And after 9/11, I couldn’t justify leaving my two children for 18-hour workdays; I needed a job that made more of a difference in the world. In 2001, I founded Little Laureate Inc., an educational media company for young children. 

There was very little to persuade me to leave my family and business for a television show — until Richard Branson came along. 

You don’t have to be an entrepreneur to respect Sir Richard Branson, but if you are one, he is your god. There is no better brand-builder on the planet, and his philosophy that there is no “work” or “play” — only “life” — is intoxicating. 

Three months after he announced that he was creating The Rebel Billionaire: Branson’s Quest for the Best, in which he would take entrepreneurs on business challenges around the world and re-create some of his own adventures, I was on a flight to London as a cast member. All details of the show, our destinations, and even the prize, were kept secret. It seems odd to fight for unknown spoils, but that is in essence what entrepreneurs do every day. When you start your own business, you don’t know if your investment will pay off or not. It’s the risk that actually drives you, not the concrete reward. 

The cast of 16 was split into two teams and, like Donald Trump, Richard Branson eliminated someone after each week’s task. But instead of cutthroat board scenes, we had friendly competitions in which those eliminated were grateful for the experience. Branson even knows how to fire people with panache. 

In many ways, Rebel Billionaire and The Apprentice are reflections of the differences between corporate business and entrepreneurship. The Apprentice cast was given $50,000 and access to top firms in New York City to launch a brand. We were dropped in locations where we didn’t speak the language, weren’t allowed a translator, and had minuscule budgets. We were asked to be more creative with less; instead of having a big budget for an advertising campaign, we were given a couple of dollars and told to engineer a public-relations stunt for free press. When we won a challenge, there was no reward — no massage, no helicopter ride. The life of an entrepreneur is not driven by expense-account partying. Victory is celebrated with each day’s mere survival. 

Mirroring Branson’s life, our entrepreneurial tasks also had a humanistic bent to them. I was honored to be the winning team captain in Africa when we were asked to come up with business plans for sustainable development in an AIDS-ravaged village that lacked even running water. It’s hard not to be touched when you discover that you can send a child in Africa to school for a year for the price of a latte. Our business plan has since been implemented in the village, and upon my return home I spearheaded a fundraising campaign, started a pen-pal program with local elementary school children, and have sent boxes of supplies to them. 

Where The Apprentice winners had clear-cut tasks with objective requirements — whoever makes the most money wins — our tasks were more ambiguous and the judging more subjective. In Tokyo, we were given 24 hours to create a presentation for non-English-speaking Japanese businessmen. We did research and discovered that the Japanese have a less bawdy and more respectful culture than Americans do; we were advised not to rely on words because they are so easily misconstrued in translation, and to avoid a sexy sell. When our sumo wrestler presentation lost to the opposing team’s “Virgin Gives Good Bed” song-and-fishnet-stocking-strewn dance number, I was disheartened. However, this, too, is true to life. Being an entrepreneur often means being at the whim of one individual — the crazy distributor who won’t budge, or the sexist investor who calls you “little lady” but holds the keys to your financial future. To a large extent, being a successful corporate businessperson is about navigating the system, while being an entrepreneur is about managing the individual. 

I deduced that Branson planned on announcing the winner as the “next Richard Branson” — and I didn’t think he was going to tell the world that he had found his double in a Midwestern mom who makes baby videos. I correctly pegged Shawn, the spiky-haired, wild, but deeply caring founder of a company called LoveSac, to win. My goal was to make it to the Final Four and, above all, to finish better than the model who wondered aloud what “H.R.” stood for. I succeeded, and had the opportunity to visit every location (seven countries on four continents) and participate in every challenge. 

I also reclaimed my fearlessness. As any new mom can tell you, it’s easy to lose your identity and self-confidence under a daily pile of diapers. It’s heartbreakingly hard to cut your own apron strings. Still, I want my children to be inspired by me, not just view me as a chauffeur. The Rebel Billionaire was a chance to reclaim my own inner rebel. How many moms have the moxie to rappel out of a Blackhawk helicopter in a sandstorm in the Sahara, or take on Class 5 rapids in the crocodile-infested Zambezi River? 

I’m often asked if I would I do the show again. I missed my children so badly that I ached. I lost 40 pounds from poor diet. I was sick for three months upon my return with an Asian bird flu. 

I would never, ever do it again. 

Except maybe if Oprah called.

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