TGM Classic | Alana Winter | Born To Be An Entrepreneur

In today’s episode of The Greatness Machine, Darius chats with Alana Winter, serial entrepreneur, creative thinker, founder of MI6 Academy and Stiletto Spy School and guide on the path to self-aware leadership. Her journey has taken her from university admission at 16 to simultaneously being fired by her dad and set up in her own business. Following a string of challenges and feelings of burnout, she sold her business in 2006, leading to some powerful questions: “Who am I now? What do I do with my life?”

In this episode, Alana and I talked about:

  • Alana’s background and unusual upbringing, and why she was literally born to be an entrepreneur
  • How her father helped her start her first business… by firing her
  • The challenges she faced in that early business, such as burnout, employee theft and even embezzlement from a business partner
  • Why she believes that a lack of passion and misalignment set the stage for the challenges she faced in her early entrepreneurial career
  • How she navigated “the void” after selling her first business with no plan for the immediate future
  • And other topics…

Meet Alana:

Alana Winter is a serial entrepreneur, creative thinker, and guide on the path to self-aware leadership. A master at helping others unearth their roadblocks, Alana runs retreats, workshops, and one-on-one trainings to help transform the lives of business leaders and their teams.

Meet Darius: 

Darius is your host of The Greatness Machine. Darius is a mad scientist, high-growth CEO, serial entrepreneur, author, conscious capitalist, speaker, and entertainer. Darius is on a quest to create 1,000,000 Core Value Driven Organization by 2030. He is calling this “The Core Value Revolution.” Darius is an alumni of the Birthing of Giants Entrepreneurial Program at MIT and Stagen Integral Leadership Program. Darius’s accolades include being ranked #9 Top Rated CEO in America on Glassdoor, has won numerous Stevie Awards, and has founded and grown organizations that have been ranked #40 in the Inc. 500 and were ranked #3 Best Places to Work By the San Francisco Business Time. He is all about the P’s: Passion, Pizza, Puzzles, and, especially, Pink Unicorns. His book, The Core Value Equation, is an Amazon #1 Best Seller and is available at

The Greatness Machine shares lessons on how to framework your drive for results, create limitless space, and win the war on talent.

My team and I are on a mission to help YOU create a cultural revolution. I want to teach you how to build a core value driven organization. 


Make Greatness Happen!



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Twitter: @kingdarius

LinkedIn: @dariusmirshahzadeh


Don’t let your Core Values become a company artifact!  Learn how to make Core Values the language of your organization.  Pre-order my book The Core Value Equation found at the link below 

The Core Value Equation




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