July 15, 2025 #1 Local News, Information and Event Source for the Century City/Westwood areas.

MILLION DOLLAR LISTING: Young Turks in the Real Estate World

Chad Rogers

Recently I interviewed the three young stars of Bravo’s Million Dollar Listing show.  

I never heard of the show or these kids but it was fun taking part in their adventure. The interview took place in a movie star’s backyard in Malibu–a nice change of pace from my windowless office.  

Josh Flagg, Madison Hildebrand and Chad Rogers are all up-and-coming real estate superstars. Each of them sold several million dollars’ worth of properties at a very young age.  

Josh Flagg

I was told Million Dollar Listing is particularly popular in Middle America, where viewers see spectacular properties being sold at astronomical prices in a highly competitive environment.

The TV show gets unexpectedly testy. I won’t spoil any surprises here.

Westside Today: How are you coping with the downturn in housing values and mortgages?

Chad Rogers: I predicted that this was going to happen three years ago. I’m glad that mortgage rates have gone up and housing values have gone down recently because people were over-spending and it was not good for our economy.

Josh Flagg: L.A. is the first to see the effect of an up market. We are also the last to see the effect of a down market. L.A. is insulated, not immune, but isolated. In the next several years we’ll see the truly professional agents succeed and the part-timers leave the business.

Madison Hildebrand: What downturn? Ha! I just keep on trucking – with a little extra creativity going into each day.

Madison Hildebrand

WT: Are you old enough to have the experience home sellers want in an agent?

Chad Rogers: I received my license before I started college at the age of 18. I have 10 years of experience working with buyers and sellers.  The way I look at it – age is just a number.

Josh Flagg: There are sellers and buyers who connect with my energy and enthusiasm. There are also some clients who want a much more seasoned agent. I respect that. That’s what is so wonderful about this business: There is somebody for everyone.

WT: Are the other two guys your friends – or competitors?

Madison Hildebrand: I am friendly with both. I am more focused in Malibu, so it makes it less competitive. It is important to get along with your fellow agents.

Chad Rogers: Madison is someone I enjoy working with. On the other hand, I am not eager to be in a business relationship with Josh.

Josh Flagg: Everyone understands that there is some level of competition intrinsically.

WT: What’s the sale you made that had the most drama attached?  

Madison Hildebrand: I had one listing for over a year and a half because the property was in litigation. There were squatters living in this 12,000 square foot monstrosity along with rats, dead birds and broken windows. I never knew what to expect. It took four escrows and over 14 offers to get it sold. Yikes!

WT: If you were advising someone who was considering going into real estate, what would you say to that person?

Chad Rogers: The real estate business is NOT an easy business and it’s NOT for everyone. You really need to love working with people.

Josh Flagg: It’s a wonderful career.

Madison Hildebrand: Read my book, Activate YOUR Passion, Create YOUR Career.  It will tell you exactly what to expect, then decide.

in News
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