Joining the Lubar Entrepreneurship Center teaching team this fall is Tiffany Yvonne.
Tiffany is a Certified Public Accountant turned successful entrepreneur. With over 20 years of entrepreneurial experience, Tiffany has navigated the realms of insurance, residential rental investments, and youth sports camps, before founding Playmaker Solutions, a boutique leadership development firm. As a certified life coach and team leadership coach, she has worked with industry giants like TransUnion and United Airlines, specializing in curing burnout and fostering team cohesion. With a strong grasp of transformational leadership, emphasizing joy and self-awareness, Tiffany proclaims that great leadership, embodies three non-negotiables Trust, (self)-Leadership, and Connection (TLC). We’re elated to have Tiffany join us at the Lubar Entrepreneurship Center (LEC) as an entrepreneur-in-residence. Her story is a testament to the power of innovation and the willingness to evolve in one’s career.
Overcoming Challenges
Tiffany’s professional journey has been anything but linear. A CPA by trade, she spent years as a self-proclaimed “numbers nerd” before taking the entrepreneurial leap in 2004. Over the past 20 years of entrepreneurship, Tiffany has navigated diverse ventures, from owning an Allstate agency to running a youth sports camp. Through it all, she has faced her fair share of challenges, including the 2008 market crash that forced her to liquidate her entire real estate portfolio in 2012.
However, Tiffany’s story is one of resilience and reinvention. Rather than returning to the corporate grind, she decided to stay on the entrepreneurial path. This decision led to the creation of Purposeful Play, a youth sports camp focused on building leadership skills and life skills in young people. This was her introduction to the LEC.
As part of the inaugural Student Startup Challenge cohort, Tiffany honed Purposeful Play which used basketball, soccer, tennis, track, and swimming as vehicles to bring in young people. This innovative approach not only marked Tiffany’s introduction to the LEC before it was officially established but also set the tone for her future endeavors in entrepreneurship and leadership development.
Recognizing and Combating Burnout
Yet, even as Tiffany found success with Purposeful Play, she couldn’t shake the feeling of burnout. “People think burnout only happens in corporate jobs, but you can burn out as an entrepreneur probably twice as fast. It’s harder to maybe recognize because you’re doing something that you love,” she says. Tiffany mentions she was “well paid, well-traveled, and well-miserable.”
Tiffany’s journey to combat burnout began with a poignant realization while driving on the expressway. She recognized that while creating enriching experiences for her children, she felt trapped by her lifestyle. This epiphany led her to develop the concept of “planning for your pause,” emphasizing the importance of regularly unplugging and reassessing one’s goals and feelings. Tiffany challenges the prevalent “grind culture” mentality, asserting that “well-oiled machines don’t grind, they flow.”
“Right before the pandemic, I was really burned out. I looked around, and there were a bunch of other moms who were also like facing burnout, really, like, financially successful, but emotionally and physically just spent,” Tiffany explains.
The pandemic, ironically, helped catapult “She Plays,” as people were suddenly craving the joy and connection it offered. Tiffany began working with large corporate clients like TransUnion and United Airlines, helping their employees find purpose and balance. However, she soon realized that “She Plays” was more of a program than a comprehensive brand. This led to the creation of “Playmaker Solutions,” a boutique leadership development firm focusing on personal and professional growth, with an emphasis on supporting women leaders. As Tiffany’s vision evolved, so did her relationship with the LEC.
LEC Welcomes Tiffany as Entrepreneur-in-Residence
What began as a simple act of donating time to a space that inspired her gradually transformed into a deeper connection. Collaborating with Tiera Trammell, LEC Program Manager, she contributed to various workshops and events, including “Social Good Morning” and the “Black Women’s Feminist Symposium,” driven by a desire to create positive experiences rather than monetary gain. This approach ultimately led to an invitation to become an entrepreneur-in-residence at the LEC, reinforcing the idea that following one’s passion can lead to unexpected opportunities.
Tiffany’s journey is a testament to the power of resilience, reinvention, and the importance of prioritizing well-being alongside professional success. Her experiences serve as a powerful reminder that the path to success is not always linear, and that the willingness to evolve and adapt is key to navigating the ups and downs of entrepreneurship.
We are incredibly grateful to have Tiffany join our community as an entrepreneur-in-residence. She will be involved in our UWM Startup Challenge, Small Business Brown Bag Lunches, Talk Series, and more. Her commitment to fostering joy, purpose, and balance in the lives of professionals will undoubtedly inspire and shape the future of our community. We look forward to the unique skills, deep knowledge, and wealth of experience that Tiffany will bring to our team and are excited to see the lasting impact she will have on a new generation of leaders.
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