VP of East Operations | Partner

Chicago, IL

Simone Ashkar

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Expertise Areas

  • Financials

  • Leadership

As a successful entrepreneur-turned-Advisor, Simone Ashkar is good at taking big goals and whittling them down into bite-sized tasks. After years of translating theory into practice and distilling information into actionable form, Simone now helps other entrepreneurs do the same. 

Before Simone started with Cultivate, she owned a residential service franchise. Over seven years, her business grew from operating one unit to managing over 60 units throughout the Midwest. Simone’s knack for simplifying goals and her ability to work with her team in a subjective and needs-based manner translated perfectly into her role at Cultivate.

Simone Ashkar
As an Advisor, Simone provides more than a tutorial on best business practices. Relatability and genuine informed guidance from someone who has experienced business highs and lows are benefits she offers. She often works with clients who are looking to transfer their time and needs to the next layer of leadership and growth. Typical client concerns include: navigating the ownership learning curve, building out systems, hiring and exit timing
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Watching owners conquer and win is Simone’s ultimate victory. She wants them to see that the ownership journey is not linear and having an empathetic Advisor can help them adjust, solve problems and stay focused. Simone helps owners refine their perspective and become better leaders, all within the big picture and owner’s unique vision.

Simone doesn’t just advise owners; As Partner and Vice President of Operations at Cultivate, she has helped lead dozens of advisors. She excels in connecting leadership teams and culture, while growing the next layer within a business. Like all entrepreneurs, she started with a big vision. By focusing on the mechanics of the business, she went on to connect the vision to micro-steps and operational daily success.

Being part of Cultivate Advisors has enriched Simone with a learning-hungry community of like-minded entrepreneurs. At home in Chicago, she also enjoys exploring Barbados (and other warm climates) whenever she can. Paddleboarding, surfing poorly, enjoying the ocean, and being with family and friends are her favorite down-time activities.

As an Advisor, Simone provides more than a tutorial on best business practices. Relatability and genuine informed guidance from someone who has experienced business highs and lows are benefits she offers. She often works with clients who are looking to transfer their time and needs to the next layer of leadership and growth. Typical client concerns include: navigating the ownership learning curve, building out systems, hiring and exit timingAs an Advisor, Simone provides more than a tutorial on best business practices. Relatability and genuine informed guidance from someone who has experienced business highs and lows are benefits she offers. She often works with clients who are looking to transfer their time and needs to the next layer of leadership and growth. Typical client concerns include: navigating the ownership learning curve, building out systems, hiring and exit timing