Building a Business You Don’t Secretly Want to Burn Down with Lindsay Dreyer

Lindsay Dreyer

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 to this conversation with Lindsay for insights into:

• What “team fever” is, why it’s rampant, and how to avoid building a business you’ll regret.
• Why intentionality—knowing your “why”—is the must-have characteristic for high-performing leaders and teams.
• How to assess if you’re a people person or a process person, and why it matters for team leadership and the hiring process.
• Why City Chic is a brokerage rather than a team, why agents are a 50/50 mix of new and experienced, and how that shapes culture.
• How to test-drive team leadership before going all-in—without risking your business or sanity.
• What it takes to run a brokerage remotely, including the key roles and systems that make it possible.
• How to design marketing that actually keeps agents in front of their sphere (and why most fail).
• How to ramp up newer agents by connecting them with renters.
• Why simplicity in tech stacks beats complexity, how she became a “Zapaholic,” and how to drive agent adoption.
• How agents can find their right fit team or brokerage by aligning personality, lifestyle, and goals

At the end, learn about a $10,000 fridge and solo, three-day retreats.

Watch this episode with Lindsay:

Listen to this episode with Lindsay:

‍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/