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In Her Shoes

RoAnn Costin

RoAnn Costin is the founder and president of Wilderness Point Investments.

RoAnn Costin, a former two sport Collegiate All-American in swimming and rowing, is the founder and president of Wilderness Point Investments, a private equity company that focuses on investing in early and expansion stage consumer non-durable product and retailing companies.

Q: How do you define success?

A: To have a life filled with purpose and passion that gives back to family, friends, and community and that insome small way makes the world a better place. 



Q: If you could walk in any woman’s shoes, whose would it be?

A: Since childhood, I have been inspired by the life of Helen Keller who accomplished so much despite her physical challenges from birth of not being able to see, hear or speak. I followed her footsteps to Radcliffe College and am currently a Trustee at the Perkins Institute working to ensure educational and job opportunities for physically challenged individuals who, like Helen Keller, can and want to contribute to society.

Q: What is your favorite beauty product you conquer the world in?


A: All women have a best feature. I am fortunate to have inherited my mother’s smiling, blue eyes. Lancome’s Le Stylo waterproof eyeliner helps keep my eyes alive from dawn to dusk. 

Q: Which shoe from the collection best works with your daily routine and why?


A: Between meetings for my investment firm, board commitments for my portfolio companies and non-profit institutions, my daily schedule is usually booked from early morning till late in the evening. As such, I often need footwear that can take me through breakfast meetings, airport runs, and elegant dinner events. Sarah Flint’s Alexandra boot offers me the comfort of a slipper, the support of a running shoe and the elegance of my favorite SF heels. 

Q: Where do you like to unwind and unplug?

A: Anywhere near the water. Having grown up by the ocean and swimming competitively BC (before children), I love to sit by the ocean at the end of the day with a glass of good wine and great friends.

Q: Who was the first woman or women you looked to for inspiration?

A: Brilliant, bold and beautiful, my mother put herself through college, graduated Phi Beta Kapa, raised six children and ran her own healthcare company while finding time to serve on political and philanthropic boards. She taught me the importance of education and a strong moral compass to find purpose and success in business and life. 

Q: What’s the most important lesson you’ve ever learned?

A: In business: Go out and get the facts and then face the facts.
 In life: Our lives will be enriched not by material possessions we accumulate but by the love we give and the friends we gather.

Q: Flats or heels?

A: Flats for work and heels for dancing!



Q: What is your hidden secret power?

A: Perseverance. Where there is a will; there is a way.

Q: If you could give the next generation of women one piece of advice, what would it be?


A: Trust yourself and make tough decisions with determination, courage, compassion, and integrity. 

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