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Entrepreneur. Business Leader. Philanthropist. Angel Investor.

Click here to read Sandy’s story, told in her own words.


Sandy Cleary,  a.k.a. The High-Heeled Investor®, has taken a nontraditional path to reach the top pinnacles of business. After growing up as the youngest of four kids in a lower income neighborhood in Boston, Sandy went on to get a degree in space physics at the Florida Institute of Technology. After obtaining her degree, she moved to Southern California and started her career designing and building guidance systems for ballistic missiles. 

In 1993, Sandy endured the devastating loss of her brother. Before his passing , he told her, “If you do what you love, you will always succeed.” Sandy loved to cruise. She would take at least one weekend cruise a month, and it truly served to de-stress her.

So, she took that advice to heart and in 1995 after her father also passed away, she decided to move back home to Boston to follow her passion for cruising while taking care of her ailing mother. 

Sandy set up shop in her mother’s basement for her next venture in life – CruCon Cruise Outlet -- an online travel agency focused on selling cruises. At that time the Internet was very young, but as a space physicist, she was familiar with it and its potential. She also knew that her strict, Irish mother would NEVER let strangers come into her home, so her business would need to be Internet based. 

After accidentally setting her mother’s kitchen on fire while toasting a pop-tart during a sales call, she decided it was time to take up actual office space in Boston. Within the first year, it was a $1M company and making waves in the travel industry. By 2004, Sandy opened a satellite office in the unlikely location of Moultonborough, New Hampshire, and by 2005 the satellite office was CruCon’s primary headquarters.

Sandy grew CruCon Cruise Outlet from a small online travel agency into one of the largest sellers of cruises in North America with more than $135 million in annual cruise volume. She then sold the company to Travel Leaders Group, a $24 billion dollar travel powerhouse and moved on to her next passion project -- helping other entrepreneurs.


In 2017, Sandy founded SLC Group Holdings with the charter to partner with entrepreneurs and small businesses needing funds to grow their companies and help them bring their products to market to propel them faster on the road to success.


To this end, Sandy has been working hard on developing a series of services, workshops, educational conferences, webinars, podcasts and blogs -- all with a focus on entrepreneurship, business development, business management and leadership. 

Sandy partnered with HSN, as a featured speaker at HSN’s American Dreams Academy, sharing her journey from the basement to the boardroom with the participating entrepreneurs. After also sitting on the American Dreams pitch panel as an angel investor, alongside HSN and QVC, she has now invested in several of the entrepreneurs she met through the Academy.
Sandy knows that a business’s journey should not simply begin and end with its own balance sheet. Sandy also believes that businesses should give back to the community. She has donated millions to charitable organizations, largely focusing on those that support youth and families of New Hampshire.   
Sandy has won several awards including Business Leader of the Year for 2018 from Business NH Magazine, the CLIA Hall of Fame Award for Lifetime Achievement in the cruise industry, and the Women of Achievement Award from Girls, Inc. 

Follow Sandy Cleary™ on LinkedInInstagram and Facebook 

Sandy Cleary_At the office_burgundy top


  • HSN American Dreams Academy

  • International Home + Housewares Show

  • The National Hardware Show, 1st Annual Women’s Empowerment Series

  • Pickler & Ben show

  • SEE Science Center Evening of Discovery & Giving 

  • Woman to Woman: Shooting for Greatness  

  • NH Business Review: Powered by Women Event

  • CASA Cares Fundraising Galas

  • HSN on-air appearance


Business Leader of the Year Award 2018,
  • Business Leader of the Year 2018, Business NH Magazine

  • Lifetime Achievement Award 2018, CLIA (Cruise Lines International Association)

  • Business of the Year Award 2017, Business NH Magazine

  • Torch Award for Marketplace Ethics 2017​, Better Business Bureau

  • Outstanding Women in Business 2014, NHBR & Centrix Bank 

  • Outstanding Women in Business Award 2014, NH Senate

  • Community Pride 2014, Meredith, NH Chamber of Commerce 

  • Business Excellence Award 2014, NH Business Review

  • Appreciation Award for Fundraising Efforts, United Way 2011/2012 

  • CASA Deepest Appreciation Award for Commitment to Improving the Lives of NH Children 

  • Intriguing Women Leaders 2013, Business NH Magazine 

  • Top Women-Led Businesses 2013, Business NH Magazine 

  • Golden Hammer Award 2014, Lakes Region Chamber of Commerce 

  • “Beautiful Award”, Wolfeboro Chamber of Commerce, making the Wolfeboro area attractive for the benefit of the community 

  • Centrix Bank “C-Beyond” Award


  • Entrepreneurship

  • Business Development

  • Business Management

  • Leadership

  • Start-Ups

  • Existing Businesses

For more information on these services, click here and fill out the Contact Form.


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