About Richard Montgomery
I’ve spent 55 years in every corner of the real estate industry — not because I planned it, but because I kept asking one question:
“How can this work better for the people buying and selling homes?”
I began as a real estate agent in 1966 in Green Bay, Wisconsin. Over the decades, I’ve:
- built and run brokerages
- developed residential and commercial properties
- founded a relocation company that outperformed industry benchmarks
- consulted for national real estate brands
- participated in over 20,000 real estate transactions
What matters most is this: I’ve witnessed firsthand how confusing and overwhelming the home-buying and selling process can be for consumers. And I’ve dedicated my career to fixing that.
Why DearMonty.com Exists
For the past 14 years, I’ve written a nationally syndicated real estate Q&A column based on real questions from real homeowners and buyers.
Every week, readers share concerns like:
- “Can I trust my agent’s advice?”
- “Am I paying too much in commissions?”
- “How do I know if I’m making the right decision?”
- “Why does this feel so complicated?”
DearMonty.com is my way of paying it forward — providing unbiased, experience-backed guidance with no sales pitch, no hidden agenda, and no corporate influence.
Just straightforward answers.
A Contrarian Perspective
When I started in the business, I was a firm believer in the traditional brokerage model.
It took 25 years of observing and experimenting to realize something was wrong.
Over time, I shifted from disciple to contrarian.
My experience spans every angle:
- As an agent and broker: I understand how deals are made — and how consumers can get left behind.
- As a developer: I know how properties are built, valued, and brought to market.
- As a relocation specialist: I’ve guided thousands of families through stressful transitions.
- As an innovator: I’ve tested and implemented modern methods in one of the slowest-to-evolve industries.
This isn’t about credentials — it’s about perspective.
When you’re making the biggest financial decision of your life, you deserve insights from someone who has seen the whole picture.
My Mission: Education First
In real estate, information is power, and the industry has historically kept more of it than consumers.
Agents know more than their clients, and that knowledge gap creates anxiety — and costly mistakes.
My goal is simple: close that gap.
Whether you’re:
- buying your first home
- selling a property you’ve owned for decades
- trying to understand your agent’s recommendations
…I want to give you the knowledge and confidence to move forward.
What I’m Building Now
After 55 years studying the inefficiencies in real estate, I co-founded Propbox, a platform designed to bring:
- transparency
- simplicity
- modern consumer-grade technology
to home transactions.
Today’s buyers and sellers expect online experiences like Amazon, Uber, Airbnb, and Instacart — and real estate should be no exception.
Meanwhile, DearMonty.com remains my ongoing commitment:
free, unbiased real estate education when you need it most.
I’ve also written two books:
- House Money: An Insider’s Secrets to Saving Thousands When You Buy or Sell a Home
- The Complicated Home Sale: Fixing the Rigged System
Both reflect decades of learning what works, what doesn’t, and what consumers need to know.
Let’s Connect
Have a real estate question?
Browse hundreds of articles and Q&As — or submit your own.
I’m here to help you navigate the complicated world of real estate, one question at a time.
