At The End Of The Day

Can Mentorship and Resilience Shape Your Entrepreneurial Journey?

Chris Raimo Episode 34

This week on "At the End of the Day," host Chris Raimo sits down with the inspiring Jessica Flynn, award-winning educator, bestselling author, TV host, and social entrepreneur. Jessica shares her remarkable journey from a first-generation Canadian with no entrepreneurial influences to building a portfolio career that empowers youth and adults alike.

In this candid conversation, Jessica opens up about:

  • Growing up without business role models and discovering entrepreneurship by chance
  • The power of mentorship and how key figures shaped her path
  • Building resilience through setbacks, financial challenges, and the realities of entrepreneurship
  • Why empowerment is about knowing your strengths and celebrating others'
  • The importance of community, collaboration, and paying it forward
  • How creativity is a muscle we can all strengthen, no matter our age
  • The mental health side of entrepreneurship and why self-care is non-negotiable
  • Her top traits for entrepreneurial success: openness, resilience, creativity, and patience

Connect with Jessica:

https://www.linkedin.com/in/the-jessica-flynn/
https://www.thejessicaflynn.com/
https://www.theflynncollaboration.com/
https://www.theyoupowerproject.com/
https://www.theacademysgb.com/ 


Whether you’re an aspiring founder, a seasoned business owner, or just love stories of growth and grit, this episode is packed with wisdom, honesty, and actionable advice.

Plus: Jessica and Chris discuss why your "why" matters, how to find your people, and the real, unglamorous side of building something meaningful.

Tune in for a conversation that will leave you inspired to trust your wings, embrace lifelong learning, and empower those around you.

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