Michael S. Liebowitz - Serial Entrepreneur | How Taking Calculated Chances Built a Business Empire

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Michael S. Liebowitz is a veteran entrepreneur and executive with over 25 years of experience across insurance, finance, and real estate. He is Chairman and CEO of Douglas Elliman Inc., one of the largest U.S. residential brokerages with over $30 billion in annual sales. Liebowitz has built, scaled, and exited multiple companies, including Harbor Group Consulting (acquired by NFP Corp.), Innova Risk Management (PE acquisition), and High Street Valuations (sold in 2020). He also led the turnaround of publicly traded Nocopi Technologies as CEO. In 2018, he founded M2A Family Office to oversee his investment portfolio and philanthropic initiatives.

➡️ Show Links

https://www.instagram.com/michaelsliebowitz/
https://www.linkedin.com/in/michael-s-liebowitz-84946b42/

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➡️ Talking Points

00:00 - Intro
03:16 - Why Michael Joined Douglas Elliman
07:36 - Michael’s First Steps in Business
12:33 - Keys to Entrepreneurial Success
16:33 - Buying Back & Selling His Own Company
31:43 - Sponsor
34:29 - Biggest Lessons from the Journey
38:04 - What Makes a Great Operator
41:01 - Signs of a Winning Entrepreneur
45:52 - Hiring the Right People
48:49 - Ivy League vs Entrepreneur CEOs
53:00 - Why the Board Chose Michael
58:03 - What Keeps People at a Brokerage
59:49 - Outdated Brokerage Mindsets
1:02:22 - Why Some Brokerages Will Fail
1:03:52 - Sponsor
1:07:32 - How Brokerages Actually Grow
1:15:02 - Tips for Real Estate Agents
1:22:40 - Why Michael Stays Hands-On
1:23:48 - Words for Shareholders
1:30:53 - Final Advice
1:32:29 - Habits Behind the Success
1:37:26 - One Lesson for His Kids

➡️ Success Story Podcast - Stories Worth Telling

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Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott Clary.

On this podcast, Scott has candid interviews with entrepreneurs, celebrities, notable figures, and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas, and insights.

He sits down with leaders and mentors and unpacks their stories to help pass those lessons on to others through both experiences and tactical strategies for business professionals, entrepreneurs, and everyone in between.

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