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From Real Estate to Cannabis: Josh Josephs Entrepreneurial Journey

Episode 39


In this episode of the Matthews Mentality Podcast, Kyle sits down with Josh Joseph, founder and CEO of Big Plan Holdings. They delve into Josh's diverse career journey, spanning real estate, cannabis, and entertainment. After making a pivotal exit from the cannabis industry valued at approximately $850 million, Josh shares insights on leadership, drive, and navigating life's challenges. Additionally, they discuss his move to Nashville, the founding of the Joseph Family Foundation, and new ventures in hospitality featuring partnerships with icons like Hank Williams Jr. and Jon Bon Jovi. A story of relentless ambition, strategic investments, and personal growth.



Show Notes:

00:00 Learning from Leaders: Adopting a Leadership Style

00:52 Introduction to Josh Joseph: Entrepreneurial Journey

01:46 Moving to Nashville: A New Chapter

04:06 Daily Routine and Work-Life Balance

05:04 Diverse Ventures: From Cannabis to Sports

08:48 Early Life in Chicago: Humble Beginnings

17:01 College Years: Finding the Path

27:17 Starting Out in Real Estate

27:46 Property Management Challenges

32:58 Transition to Investment Sales

34:44 Joining Hilco Real Estate

37:57 Founding Frontline Real Estate Partners

50:05 Entering the Cannabis Industry

58:21 Reflecting on the Cannabis Industry's Challenges

59:59 Balancing Work and Family Life

01:02:26 The Decision to Sell and Its Aftermath

01:05:20 Navigating the Sale Process

01:07:03 Post-Sale Reflections and Litigation

01:12:29 New Ventures in Nashville

01:15:28 Building Big Plan Holdings

01:26:00 Advice for Young Professionals

01:30:52 The Importance of Hard Work and Learning from Failure

01:33:45 Conclusion and Final Thoughts



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