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Playing It Safe Might Be the Riskiest Thing You’re Doing
We were told to follow the rules: get the job, play it safe, save what you can, and hope it adds up to freedom someday. But what if that path is actually keeping us stuck?
In this episode, we talk with someone who stopped coasting. Andrew was living the “smart” financial life—until he realized comfort was costing him control. Now? He’s building a life of freedom on purpose. From buying his first multifamily in Omaha to managing an 8-bedroom co-living space in Austin, he’s not chasing some get-rich dream. He’s building systems, making real decisions, and playing the long game—with clarity.
We unpack the wake-up call that shook him, the $44K mistake that taught him, and the mindset shifts that freed him.
📌 Key Topics:
✅ Why playing it safe can quietly drain your future
✅ The high price of hiring the wrong contractor
✅ How a rent-by-room model created consistent cash flow
✅ What it takes to run properties while keeping your day job
✅ How clarity and control beat hustle and hype
Freedom doesn’t come from more comfort—it comes from making moves that matter.
Chapters:
00:00 The Real Estate Journey Begins
02:23 Diving into Real Estate Investment
07:04 Understanding Rental Strategies
12:29 The Multifamily Property Decision
17:11 The Roof Nightmare and Lessons Learned
22:33 Balancing Personal Challenges with Property Management
30:37 Balancing Profit and People in Property Management
31:58 Building a Reliable Maintenance Team
34:22 The Importance of Systems in Property Management
38:14 Personal Challenges and Family Connections
42:36 Life Lessons from Loss and Travel
45:00 Finding Freedom in Flexibility
01:24:50 Defining Freedom in a Nomadic Lifestyle