What does it take to build a real estate business that you truly love - rather than one you secretly want to burn down?
In this conversation, Lindsay Dreyer, founder of City Chic Real Estate and Happy Agent Co, shares hard-won lessons from 14 years of brokerage ownership, including how she runs her boutique firm remotely, why intentionality trumps “team fever,” and how to design a business that supports—not sabotages—your life.
In a story of clarity, process, and self-awareness, Lindsay breaks down the difference between being a people person and a process person, why most agents shouldn’t start teams, and how to know if you’re better off plugging into someone else’s system or building your own.
You’ll hear how City Chic’s 30-day onboarding challenge weeds out the uncommitted, why their agents are 50/50 new and experienced, and how a focus on admin, marketing, and transaction management enables top solo agents to thrive without needing to build teams of their own.
Lindsay also details the leap to running their business from 500 miles away, the key roles that make remote leadership possible, and the systems that keep everything humming. You’ll get a transparent look at their tech stack (including why she’s a self-described “Zap-aholic”), the real numbers behind their 12-agent, $72M brokerage, and the philosophy that underpins the Happy Agent approach: start with joy, design for your life, and don’t buy into the myth that more is always better.
Watch or listen for insights into:
At the end, learn about a $10,000 fridge and solo, three-day retreats.
Follow Lindsay Dreyer:
→ https://www.instagram.com/lindsay.dreyer/
→ https://citychicrealestate.com
→ https://happyagent.co
Follow Real Estate Team OS:
→ https://www.realestateteamos.com
→ https://linktr.ee/realestateteamos
→ https://www.instagram.com/realestateteamos/
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It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.
Crime Junkie
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