About me

I am a Builder, a Leader, a Creator, a Speaker, and now a published Author. I am committed to helping people grow their vision and realize their full potential.

Bill Ryan

About Bill Ryan

Born to the founders of a Chicago homebuilding company, which Bill always knew he would join.

A native to the Chicago area, Bill spent much of his career growing and developing startup companies. He started his real estate career at an early age, holding different summer jobs in the family business. After a stint in graduate school, Bill joined Town & Country Homes (the family business) full time.

Under Bill’s leadership, Town & Country tripled home sales in three years, significantly improved profits, and unseated the market’s #1 homebuilder, which had more than twice the number of communities as Town & Country. This success led to the company becoming the first production homebuilder in Disney’s new town development, Celebration. With his passion for home design, he has designed hundreds of homes. He has built and sold over 10,000 homes over his career. A graduate of Notre Dame, Bill was included in the Crain’s Chicago Business “40 Under 40” list in 1992 and in 1998 was named as a Legend in Residential Marketing by the National Association of Home Builders.

Bill founded two real estate development companies: The Roslin Group, which focused on designing and building mixed-use communities in the Midwest; and Wyndham Development Group, which built residential properties in Chicago’s northwest suburbs. Bill resides in the Florida area. 

Don’t get hung up on the word success. There is so much noise around that word today. Humans evolve. We expand our potential every day. Admire the output of another but hold fast to the belief that you have your own contribution to offer this world. Your work can advance the growth of us all.

Bill Ryan

Books by Bill

Read “Fix Your Why” – Bill’s first book. His story of how he transformed his family’s business. Bill is in the process of completing his second book, “Stacking: The Path to Brand Dominance.”

Fix Your Why

Fix Your Why

"Stacking"

"Stacking" Coming Soon

The Path to Brand Dominance

Shaping

"Shaping" Coming Soon

"Shaping: The Power of Intention"

Fix You Why is a rare book that follows a man`s journey through life with a focus on self awareness, candor, and innovation. The result is a fascinating read that is both enlightening and educational. Mr. Ryan`s immensely successful career through the turbulent real estate industry is magnified by his relentless struggle for growth on a personal and professional level. I highly recommend this book to anyone who is driven to succeed. It is simply a terrific story told with openness and honesty. My only regret is that I didn’t read this at the beginning of my career…

—H. LAWRENCE WEBB

EXECUTIVE CHAIRMAN | THE NEW HOME COMPANY

Fix Your Why is the opposite of too many self-help, motivational books that are a bit too high brow, a bit too campy, and not directive enough. If you’re looking for trite motivations or rah rah stories, this is not the book for you. But if you’re looking for no shortcuts, hard work principles that can serve to motivate and direct you to long term success – while hopefully avoiding some short term “failures” – Fix Your Why is a worthy read. Frankly, it will help you not just in business, but in life, which of course are correlated. I met Bill circa 2011, when he was at a low point, with his business struggling and life up in the air. Even so, he had a calmness to him, which I didn’t understand then, but do now. Whether even he knew it then, Bill was – perhaps subconsciously – zeroing in on and trying to fix his Why. Obviously, the “fix” is a never ending work, but as Bill explains, if understood and embraced properly, that can be an asset, not a liability.

—WILLIAM CHOSLOVSKY

CHICAGO UNIVERSITY OF ILLINOIS (BS 1990) HARVARD LAW SCHOOL (JD, 1994)

Billy Ryan has written a powerful and insightful book which will help you successfully pursue high levels of achievement. I wish I had access to this book earlier in my career!

—STEVE MENZA

FOUNDER AND CEO | WHOLESOME PRODUCTS, LLC