Standing before 20,000 agent-followers in New Orleans last week, Gary Keller presented his latest triumphant moment, a mix of real estate and showmanship.

Real estate has a long history of exaggerated claims and idyllic promises.

Every day, agents pitch a dream — a new place, a refashioned life in a fresh neighborhood. Developers implore local officials to imagine a new community from nothing more than a colorful collection of beautiful images. In the 19th century, the U.S. government gave away half the country in 160-acre parcels to tens of thousands of homesteaders with the promise of a new start in an unknown part of the world.

The technology industry is also a master of peddling dreams. This spaceship will take you to Mars. A  self-driving car will deliver you to the office and this robot will cook you a feast. Easier, faster, better is coming your way with this new product, application or virtual experience.

What could be more fantastical than the promise of technology?

Standing before his 20,000 agent-followers in New Orleans last week, Gary Keller presented his latest triumphant moment, a well rehearsed mix of real estate and technology showmanship. Think big-tent Baptist revival dropped in the middle of the Consumer Electronics Show in Las Vegas.

The ultimate salesman, the founder of Keller Williams blends the language of real estate with the promise of technology, leading his followers down a path of hope, better times—and, of course, more sales.

Many in the industry sit on the sidelines, aghast at Keller’s claims and turned off by his undeniable magnetism (and sometimes bitter arrogance).

But no one understand the fears, the aspirations and the quirks of the average real estate agent better than Keller. In New Orleans, he took the stage dressed in black like Johnny Cash at Folsom Prison, offering hope to his fans-cum-family, a performance right out of Steve Jobs overselling the perfection of his new tech products to his Apple groupies at San Francisco’s Moscone Center a decade-plus ago.

Like Jobs and Cash, Keller crafts an irresistible narrative, just as he did when he first sold real estate as a top producing agent 45 years ago in Austin, Texas, rolling around town with a guitar in the back seat of his VW bug.

Like most successful people, Keller is a complicated matrix of personalities, driven by his own ambitions, fears and blind spots. He can be charming, Bill Clinton-like in private, but also dark and cynical in small gatherings. On a big real estate stage, no one matches his cadence, confidence and ability to weave  a tale of optimism, fear and promise. He is part amateur economist, self-proclaimed tech genius and preacher.

His biggest asset? His track record. He has faced formidable competition before — RE/MAX and Realogy — Keller beat down his competitors, seizing on their weaknesses in the business cycle. KW agents can be cult-like in their admiration and love for Keller, but he helped many of them become fabulously successful and many credit their guru for their riches. Their go-to hashtag is #ImWithGary.

But something is different about the industry today. Zillow, Opendoor, Redfin and Compass have brains and passion like Keller. But they also have their hands on a seemingly endless supply of capital and, perhaps more crucially, the tech DNA that Keller, who despite his triumphant claims, does not possess.

The legacy industry follows the same roadmap with almost identical business models. The new entrants turn everything upside down, making it tricky for the old guard to figure out which way to turn. Zillow succeeded because of its own efforts, but also because the industry found itself stumped about what do in the face of a truly disruptive threat. In the end, they lost the consumer to the upstart Seattle portal.

In this new fight, Keller finds himself simply out-engineered. Words matter when motivating agents, but catch phrases alone will not build the technology platform that he wishes for — and, more crucially, that he promises his army he is set to deliver. By promising his agents the moon, the sky, and the stars — what, after all, can top comparing one’s platform to Netflix at this moment in time? — he risks real disillusionment as the competition continues its nonstop innovation, too.

And yet in the end, there is something even more complicated going on here.

The agents who are rooting for Keller are depending on him to deliver a chimerical promise. Give us the newness of technology, they think — but keep things exactly the way they are.

Keller understands that tension, and his Achilles heel may be that he believes it is possible.

Email Brad Inman

Brad Inman will be joining real estate’s leaders this April 8-10 for Inman’s annual retreat, Disconnect in the Desert, in Palm Springs. It’s an invite-only gathering, and tickets are limited. If you think we missed you, drop us a line.

Show Comments Hide Comments
Sign up for Inman’s Morning Headlines
What you need to know to start your day with all the latest industry developments
By submitting your email address, you agree to receive marketing emails from Inman.
Thank you for subscribing to Morning Headlines.
Back to top
Only 3 days left to register for Inman Connect Las Vegas before prices go up! Don't miss the premier event for real estate pros.Register Now ×
Limited Time Offer: Get 1 year of Inman Select for $199SUBSCRIBE×
Log in
If you created your account with Google or Facebook
Don't have an account?
Forgot your password?
No Problem

Simply enter the email address you used to create your account and click "Reset Password". You will receive additional instructions via email.

Forgot your username? If so please contact customer support at (510) 658-9252

Password Reset Confirmation

Password Reset Instructions have been sent to

Subscribe to The Weekender
Get the week's leading headlines delivered straight to your inbox.
Top headlines from around the real estate industry. Breaking news as it happens.
15 stories covering tech, special reports, video and opinion.
Unique features from hacker profiles to portal watch and video interviews.
Unique features from hacker profiles to portal watch and video interviews.
It looks like you’re already a Select Member!
To subscribe to exclusive newsletters, visit your email preferences in the account settings.
Up-to-the-minute news and interviews in your inbox, ticket discounts for Inman events and more
1-Step CheckoutPay with a credit card
By continuing, you agree to Inman’s Terms of Use and Privacy Policy.

You will be charged . Your subscription will automatically renew for on . For more details on our payment terms and how to cancel, click here.

Interested in a group subscription?
Finish setting up your subscription