The Commercial Real Estate Playbook for Time Freedom

In this episode of Smart Money, Chris Swartz sits down with Ryan Stackhouse, commercial real estate investor, entrepreneur, and lifestyle design advocate, to unpack how he built a commercial real estate portfolio that prioritizes one thing above all else: time freedom. Ryan shares his journey from leading a successful career in the mortgage industry to transitioning full-time into real estate investing. Starting with single-family rentals and gradually moving into multifamily properties, hotels, and eventually commercial assets, he explains how years of intentional investing allowed him to create a life centered around family, health, and experiences instead of long work hours and constant stress. From using AI tools like ChatGPT and Claude to analyze leases and financial statements to identifying recession-resistant commercial assets with long-term tenants, Ryan offers practical insights into the mindset and strategies behind building sustainable wealth. He also opens up about the personal side of success. Why he walked away from a high-income career, how becoming a father reshaped his priorities, and what it truly means to design a life on your own terms. In this conversation, Ryan and Chris discuss the importance of starting small, avoiding unnecessary risk, building wealth through intentional decisions, and why true success isn't measured by net worth, but by the freedom to be present for the people and experiences that matter most. 🎧 Hosted by: Chris Swartz 👤 Guest: Ryan Stackhouse – Commercial Real Estate Investor & Founder of Cashflow to Freedom Academy Ryan Stackhouse is a seasoned real estate investor with more than 20 years of experience building wealth through residential and commercial real estate. After starting with single-family rentals, he expanded into apartments, hotels, industrial properties, and medical facilities. Today, Ryan manages over $50 million in assets while helping others learn how to create financial independence and time freedom through strategic investing and intentional living.