The chapter starter—Candice Carpenter Olson

Part of the business owner to business owner series, ‘Flight paths’

See why Candice chose entrepreneurship over corporate life

Candice began her career as a mountaineering instructor. This may have helped her keep a cool head as she faced large-scale business risk, years later. When Candice applied to graduate school, her leadership roles on extreme wilderness expeditions helped secure a place at Harvard Business School. A corporate marketing job followed, where she climbed, again—up the ranks.

In 2000, Candice became one of the first women to lead an IPO1 as one of the founders of Today, she’s thriving in Colorado running Local Coffee House, alongside her daughter's design business.

Candice is one of the entrepreneurs who shares her story with us for our special video series, 'Flight Paths." Watch highlights from her interview.

How to approach risk: Don't look down

Career milestones

Graduates from Stanford in 1975

Becomes full-time wilderness and mountaineering instructor

Harvard B-School leads to Wall Street  

Rises to VP of Marketing in strategy division

Gets hired by a mentor and media titan 

Learns how to build companies

Gives birth at age 42

Welcomes daughter, launches cable network

Helps start in 1995

Becomes one of the first women to lead an IPO, chairs private school board1

Thriving is a family affair

Opens popular coffee house in Aspen with her daughter

I’m not a big believer anymore in ‘just have an idea and jump.’

At one point in her career, Candice started calling on famous media titans and visited five of them. One hired her. With an executive coach’s help, she left her job on her own terms with an excellent reputation and a significant exit package. She was beginning to understand how to navigate her chapters.

Deliberate on how you’re living in each chapter, and know what should change with the next chapter.

One day, Candice realized she had become an “Upper East Side society lady” and felt horrified. She shed that role and “detoxified” by ghost-writing a satirical novel. At the same time, she earned a Master’s degree at Teachers College of Columbia University. With that, and her entrepreneurial skills, she helped co-found a school that now serves over 3,000 students.

A change of heart brings a change of strategy

Why growing quickly can be a curse

Learn more from the entrepreneurs of ‘Flight paths’

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