How a Single Mom Built a Sales Empire

What happens when losing your job becomes the opportunity to build your own future? On Living Your Legacy, host Jay sits down with Jenn Hildebrandt, founder of TfL Collective, to explore her journey from 14 years in corporate sales to coaching women in high-ticket entrepreneurship. After losing her job, Jenn takes a leap of faith and builds a business around financial independence, flexibility, and motherhood. She shares why monetizing existing skills, understanding sales psychology, and building a personal brand can open new opportunities. But leaving a nine-to-five requires more than ambition. Jenn explores the limiting beliefs, fear, and inconsistency that hold aspiring entrepreneurs back, and why mentorship and persistence matter. Can changing how you see yourself change what you believe is possible?

KEY TAKEAWAYS

Turning job loss into opportunity: How Jenn uses her corporate sales experience to launch an independent business after losing her job.Monetizing existing skills: Why social media and personal branding create opportunities for women to turn their expertise into income.Understanding high-ticket sales: How identifying the right audience and understanding buyer psychology help entrepreneurs sell premium offers.Overcoming limiting beliefs: Why confidence, mentorship, and consistency are central to Jenn's approach to entrepreneurship.Designing a business around life: How Jenn balances single motherhood, travel, and business growth while helping other women pursue greater flexibility.

NOTABLE QUOTES

"I really believe that most people should have their own business in some form or fashion.""If you're not there building a business for free, what are you doing?""The women that make it are the ones that refuse to give up.""When in doubt, figure it out because everything is figure outable.""I designed a life around my business. I didn't create a business so that it could run my life."