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

Success Story with Scott D. Clary

Success Story Media

Business, Careers, Self-improvement, Education, Entrepreneurship

4.6 • 1.9K Ratings

🗓️ 11 April 2025

⏱️ 98 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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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59:49 - Outdated Brokerage Mindsets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

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Transcript

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0:00.0	I was fearless at 21. I grew up in Staten Island, very modest beginnings. So I grew up,
0:05.1	always wanting to kind of get out of that. Doing that at 21 was tough, but I never afraid of it.
0:10.9	Michael S. Liebowicz is the president and CEO of Douglas Elliman Inc. with over 25 years of
0:15.7	experience leading companies in insurance, finance, and real estate. He's the founder of Harbor Group
0:20.1	consulting and has redeveloped iconic properties like the Mondrian South Beach Hotel.
0:24.6	When I came into Douglas Ellman, number one reason that I took this role, Douglas Ellman brand, best brand in residential real estate by far.
0:33.6	As a 10-year-old, I always saw myself as Captain Kerr.
0:36.3	I thought like the only way I was
0:37.7	really ever going to be the CEO was it had to become it myself. Just started selling insurance
0:42.7	and then created a business out of. We handled the insurance on the World Trade Center before 9-11.
0:49.2	That business after 9-11 went through the roof. A seasoned entrepreneur and investor, Michael also
0:54.0	supports causes like Make a Wish and the Bascom
0:56.7	Palmer I Institute.
0:58.0	In this episode, we dive into his journey of building, leading, and scaling high-impact
1:02.4	ventures.
1:02.9	The successes are in the failures.
1:04.6	I think it's hard for people to really, like, believe that.
1:07.0	You can't do a good deal with a bad guy.
1:09.7	And you can't do a good deal with a bad guy and you can't do a bad deal with a good guy if you
1:11.8	do everything that you need to do the result is your stock will go up don't worry worrying is the
1:16.7	worst thing you can do welcome to success story i'm your host scott clary the success story
1:24.8	podcast is part of the hubspot podcast network. Now, HubSpot doesn't
	...

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