Turning Challenges into Opportunities: Greg Holestin’s Road to Real Estate Success The Invested Life

Welcome to the DanCan Show! In today’s episode, Dan Cantillana sits down with longtime friend and accomplished entrepreneur, Greg Holestin, to explore what it really means to build lasting success across multiple areas of life.

Have you ever wondered if it’s possible to thrive in corporate America, launch a small business, and become a successful real estate investor—all while staying true to your family, your faith, and your community? Greg Holestin is living proof that it can be done. Tune in as he shares his journey from his early days in a corporate insurance job, to launching his own insurance agency in the middle of the Great Recession, and scaling his real estate portfolio from one investment property to 66 doors. Along the way, you’ll hear the invaluable role of relationships, faith, strategic risk-taking, and generational impact.

Whether you’re an aspiring entrepreneur, a seasoned investor, or simply seeking inspiration on how to invest in what matters most, this episode is packed with practical wisdom and real-life encouragement. Grab a pen—you’ll want to take notes!

In life you are either an investor or a consumer. You either habitually create or habitually consume. So the real question is: how do you start creating? And once you start, how do you keep going?

Now, you might be asking yourself, “Dan, what’s with all the questions? I thought this was a book, not a test.” Fair enough—but without questions, how can we expect to find answers?

And isn’t that what we all want as leaders? Not just answers, but the right answers. Answers that bless the people around us. Answers that bring peace, resolution, and abundance.

This isn’t just another podcast about success—it’s a journey of self-discovery, intentional living, and building a life you love. Dan shares insights, stories, and strategies designed to help you achieve financial freedom, live with integrity, and make money effortlessly by aligning your work with your faith.

If you believe in loving what you do and doing what you love, you're in the right place.

Protect. Provide. Promote.

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