A Case for Mandatory Apprenticeship

It's not your imagination--the agent you're dealing with wasn't trained.

My mentor spent nearly ten thousand dollars on Valentine's Day cookies.

Polly Driscoll sent custom-packaged cookies with personalized newsletters to her entire client database. I should say she had me personally handpackage hundreds of custom cookies with folded, signed newsletters for a holiday most other agents ignore.

She got multiple listings from that single campaign.

That moment taught me something fundamental about this business—the agents who are successful celebrate their clients, market against the grain, and importantly, for the purposes of my hypothesis here, train the next generation of agents by showing them what types of systems work. Where to spend your money, and why.

The Expensive Paper Principle

While other agents printed MLS sheets on office copiers, Polly insisted on expensive paper and custom brochures. Professional photographers for every listing, regardless of price point.

The marketing we do for our homes is the marketing we do for ourselves.

This wasn't about vanity. It was about understanding that every interaction builds or destroys your reputation. I have applied every ounce of this in the creation of ACME.

As the market was turning in 2008, one of Polly’s high end clients had purchased an expensive new home in Chevy Chase, MD, but still had a house in Washington, DC to sell. They were expecting the insane multiple offers that all their neighbors had received, for houses far less aesthetic than theirs. But the house sat for weeks. And they were frustrated. The clients blamed Polly, even though market conditions were beyond anyone's control.

Of course the Washington, DC home did find its buyer, for far less than expectations. And while the market failure wasn’t Polly’s fault, how she handled it was classy. She knew her clients weren’t happy with her—they needed someone to blame. But when she bought the kids an expensive new treehouse for their new backyard, she planted her flag in their yard. Taking accountability for their experience, in a way, but making a contribution beyond flowers and champagne—she contributed something that would bring her clients’ kids joy and happiness. A subtle reminder that there are things outside of our control, but the joy of family and home is the real priority in all of this…

What I Learned About True Accountability

Twenty years later, I see how rare true accountability has become in our industry. What I learned from Polly was that every interaction matters - from open house conversations to document delivery timelines. Literally every word that comes out of an agent’s mouth will be heard, sometimes misheard, and translated by the buyers in the transaction into either an expectation or a misrepresentation. Words matter. I’ll have another case study on the importance of one word, a real estate butterfly effect in a future Substack.

Many agents are in a rush to move to the next step of the sale. Many agents haven’t read the contract word for word, let alone the disclosures they expect their clients to read and understand. What this means is that instead of the real estate exam focusing on principles, we need a real estate exam that focuses on the practice of real estate. The actual contract, the way to handle certain aspects of the transaction that are different every time, when to pull in an attorney, what to expect from a broker, how to draw boundaries. All of these things, and so many more, comprise our jobs. Not everyone is cut out for being an expert at this job. However, if the DRE and brokerages, in an attempt to keep warm bodies in a seat, let the untrained, untested licensee handle clients and their valuable assets, our industry will continue to lose value from the consumer POV. We have suffered some blackeyes in the recent years and there are clearly some people, some real estate lawyers and supposed consumer advocacy groups, who want our jobs to disappear completely.

The statistics tell the story. 87% of agents fail within five years. Plus, as agents we are marketed to by professional coaches, by apps, by brokerages…all promising to be the holy grail, the missing piece. The thing that will make you succeed. And as curious as I am about all the new tech, and as inspired as I am by hearing some real estate coaches run around on stage, in reality, the talent part of real estate is in the experience. And if you don’t have it, you have to learn from someone who does. Early on. And build your structures on a foundation.

Polly understood something that transformed how I handle challenges.

Collaboration over confrontation. Relationship preservation over ego protection.

Old School Wisdom in a Digital World

Polly embraced new technology but never abandoned proven connection methods. Her newsletters went via regular mail, sharing personal details and market updates.

She kept a physical address book and vendor contact list. Her database was spotless.

The data supports her approach. Direct mail campaigns maintain a 9% response rate, significantly higher than email marketing.

She never took risks with client relationships, even when digital shortcuts were available.

What I Learned About the Power of Mentorship

After two decades in this business, I believe mentorship should be mandatory, like a medical residency.

Taking time to be an apprentice, spending a couple years learning to confidently handle transactions, should be industry standard. There should be an additional round of testing after a couple of years to make sure that licensees understand the contract and the new laws/addenda. And when I say understand, I mean understand to the point of being able to defend that understanding in front of the lawyer parents of first-time homebuyer.

Only when you're fully in this business do you know what you don't know.

In inventing ACME Real Estate, I invest time and training in agents. We start with code of ethics, but we read every page of the contract word for word, we practice challenging situations, we refuse to put sales persons out in the field that don’t know how to conduct themselves professionally.

The most successful people I know are always learning, growing, staying humble and accountable. They understand that persistence and proper mentorship create sustainable careers.

What I've learned is that we have an opportunity to transform how new agents enter this profession through structured mentorship programs.

Polly's Valentine's cookies weren't just marketing. They were a masterclass in understanding who you really serve, how to reach them, and what building long term relationships truly requires—and why a real estate career cannot survive without a true measure of training from the masters.

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