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What does it really mean to bet on yourself? In this candid conversation with entrepreneur Cory, co-founder of Synergy Insurance Solutions, we dive deep into the mindset shift required to leave the perceived safety of corporate America for the unpredictable—yet potentially more rewarding—world of entrepreneurship.

Cory's journey from professional tennis coach to successful business owner offers a fascinating roadmap for anyone considering taking the entrepreneurial leap. He shares how his sports background instilled the competitive drive and resilience needed to thrive in business, particularly when facing rejection. "You're going to have to put in the extra reps," Cory explains, comparing business networking to athletic training. "In the business world, it might be doing a lot of elevator pitches and going to a lot of networking events or conferences."

Throughout his 24-year entrepreneurial career spanning three different businesses, Cory has discovered the power of strategic partnerships. Rather than trying to do everything himself, he's consistently partnered with people whose operational strengths complement his sales and business development expertise. This approach has allowed his ventures to scale in ways that would have been impossible alone. His story of pivoting from Showtime Marketing to Showtime Golf demonstrates the importance of recognizing when something isn't working and having the courage to change direction quickly.

Perhaps most compelling is Cory's perspective on freedom versus security. He frames the choice between entrepreneurship and corporate employment as being "a bull or a cow," asking listeners to consider what they truly value. "If I earn less money doing this versus climbing the corporate ladder, I'm okay with that because ultimately I value my time over the money piece of it." In an age where corporate jobs are increasingly vulnerable to disruption, the ability to control your own destiny may be the greatest security of all.

Ready to reconsider what true security means in your career? Listen now to challenge your assumptions and perhaps find the courage to bet on yourself.