Hi, I'm Winston Faircloth

I help business owners and visionary executives like you multiply your Alignment, Breakthroughs & Capabilities;  Discovering your pathway to greater time freedom and financial margin

Are you ready to experience FULFILLMENT in business

beyond what you have already achieved?

Are you ready to create a business that is the PERFECT FIT for you, meeting all of your needs and brings you incredible joy. Many people do CREATE the business of their dreams when they start connecting the dots of their life experience in new and powerful ways.  

Deep down, did you always KNOW you were an entrepreneur? When others were working for an hourly wage as a teen, you saw something you could do or sell that made more money in a FRACTION of the time. Perhaps you saw a need that no one else was meeting and it brought you such joy to serve others in a creative and novel way.

Me, too! That’s why I set out to create mentoring and group coaching programs that help people see new possibilities and radically shift their mindset about change so they could live the lives of their dreams.  

Over the decades, I’ve completely reinvented my career multiple times: moving from an executive in a locally known non-profit, to founding a multi-seven figure technology social enterprise, to joining an equity-backed technology startup.  Each and every experience has stacked, one upon another, to equip me for the next season of my career to equip you as a #Future7FigureCEO.

You too can take ALL of your life experiences and transform them into the business of your dreams.  Your transformational journey will go much more smoothly with a teammate, and I’m ready to walk alongside you. As your coach, I will guide you through a process of discovery through a series of questions and exercises designed to bring clarity and direction. And as your mentor, I will share my decades-long journey of transformation in business, in finances and in faith.  

Romans 8:28 is a verse that has brought me comfort and extra courage in the midst of significant seasons of transformation.

“And we know that God causes everything to work together for good of those who love God and are called according to his purpose…”

Your transformation begins with a decision to take action.

"Several months ago, my career was at a crossroads. I was facing a big decision about whether to pursue an opportunity for promotion when our CEO announced her pending retirement. It is not too often that internal candidates ascend into the CEO position in nonprofit organizations. Working with Winston as my career/business mentor gave me new insights and conviction to pursue my dream role. His style is encouraging and action oriented. I was able to grow as a leader and learn from Winston’s wealth of knowledge in both the nonprofit and for profit sectors. Winston’s innate capacity to listen deeply then provide feedback in a nonjudgmental way, allowed me greater clarity. And now, I have the honor of leading our community's United Way as their new CEO. I highly recommend working with Winston as a mentor. P.S. Winston is also an incredible friend! "

Michele Anderson
CEO, United Way of South Hampton Roads

So why choose me as your coach and mentor?

Faith is at the center of our work together.  Transformation can be challenging, so let’s invite the Ultimate Mentor into our work. With all of my VIP 1:1 clients we open our sessions in prayer, inviting God to bring clarity and conviction into our conversation. Matthew 18:20 promises “for where two or three gather together as my followers, I am there among them.”

Investing in your success never ends.  You get the benefit of my tens of thousands of dollars invested in personal development training for a fraction of the cost and time. I constantly invest in my own high-level coaching, conferences, masterminds and courses to bring you the best insights and questions to help you grow.

My experience in leading people and teams for more than three decades brings a unique perspective to our work together. 

As an executive in the non-profit, social enterprise and venture backed technology realms, I’ve experienced almost every work situation imaginable.



But more importantly, I’ve been able to leverage each experience to create new roles/responsibilities each time to help me grow in my career.  

Some examples include:

  • College costs were paid 95% through on-campus leadership roles in the residence dorm programs and summer sales positions. 
  • First job out of college resulted from conducting informational interviews with leaders in a field I was considering.
  • First promotion to Vice President at age 24 developed from taking my boss to lunch, requesting challenging new projects.
  • First CEO roles came from a deep desire to be responsible for all facets of an organization (sales, product, support, promotion) after achieving groundbreaking results in my prior roles.
  • Founded a technology social enterprise born out of our need for commercial level technology support with an organization that had a heart for non-profit mission.  Solving my “own itch” met the need of thousands of others with an identical need.
  • Founded information/technology consulting practice providing business process outsourcing and strategic fundraising assistance.
  • Following a prompting to leave the social enterprise and two years into my consulting career, I attended an industry conference where I “coincidentally” ran into a former mentor.  In the following weeks, we co-created a new division with P&L responsibility for 25% of the overall venture equity-backed technology company.

Preparations for Business Mentorship & Strategic Advisory

  • 15 years of executive leadership positions in three United Ways
  • Founder of technology social enterprise, growing from zero to $4.5 million in annual revenue
  • Officer in venture equity backed technology firm providing SaaS solutions for CSR and non-profit fundraising services solutions
  • The Strategic Coach Signature Program Member (Chicago)
  • Diamond Member of Brooke Castillo's Self Coaching Scholars
  • Eaglepreneur Mastermind, hosted by Dan Miller
  • Magnify Mastermind, hosted by Sara Anna Powers
  • James Wedmore’s Business By Design & BBD Live
  • VIP at Unleash the Power Within, Tony Robbins (San Jose)
  • VIP at Business Mastery, Tony Robbins (Las Vegas)
  • VIP at Date with Destiny, Tony Robbins (Palm Springs)
  • Keynote for multiple national technology webinars for United Way
  • Board chair for Lexington Children’s Theatre, successfully completing $3 million HQ capital campaign
  • Instructor/course designer for National Academy for Voluntarism (Alexandria, VA)
  • Bachelor of Arts degree: double major in Government & Philosophy from the College of William & Mary in Virginia



Until you can believe,
Believe that I believe in you.

Together, we will seek answers

 develop solutions, build accountability and chart your transformation

--- drawing upon our faith in God for His provision and protection.

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