Episode #66
Ep. 66: Is Real Estate Still Worth It? An Investor Who Changed His Mind with Chris Craig
Is real estate still the best path to financial freedom? Or are there better opportunities hiding in plain sight? In this episode of From Corporate to Cashflow, hosts Andrea Cannon and Liz Schwab sit down with investor, entrepreneur, attorney, and tax strategist Chris Craig, whose unconventional journey has taken him from the dot-com crash to building multiple businesses across real estate, tax planning, and emerging investment opportunities. Chris shares how getting laid off during the dot-com bubble unexpectedly led him into the world of distressed real estate. After building a foreclosure database for another investor, he spotted an opportunity and launched his own wholesaling business, eventually closing 3–5 wholesale deals per week while averaging around $8,000 per deal. When the housing market crashed, Chris pivoted again. He worked as a paralegal while attending law school, focused on bankruptcy law, and later built an accounting firm helping high-income W-2 professionals reduce their tax burden through strategic planning. In this conversation, Chris explains why he believes today's real estate market isn't the same wealth-building vehicle it once was, why he's selling much of his portfolio, and the new asset class he's pursuing in search of stronger cash-on-cash returns with less capital invested. We also discuss: • How Chris built a successful wholesaling business before the housing crash • Why he believes many real estate investors need to rethink their strategy • Tax planning strategies for high-income W-2 professionals • The mindset shifts that helped him reinvent his career multiple times • Why "your network is your net worth" is more than just a cliché • The realities of entrepreneurship that most people don't talk about • His latest ventures in longevity-focused businesses and other unconventional opportunities Chris is unapologetically opinionated, challenges conventional investing wisdom, and isn't afraid to question popular financial and health-related advice. Whether you agree with him or not, this conversation will make you think differently about investing, entrepreneurship, taxes, longevity and building long-term wealth. If you enjoy conversations about real estate investing, passive income, entrepreneurship, tax strategies, private lending, and financial freedom, be sure to subscribe so you don't miss future episodes of From Corporate to Cashflow. What was the biggest idea or opinion from Chris that you agreed (or disagreed) with? Let us know in the comments! **Connect with Chris Craig:** LinkedIn.com/thetaxfirm @christophercraigofficial Facebook.com/chriscraig702 --- Follow me on Instagram: https://www.instagram.com/theandreacannon Subscribe to my YouTube Channel: https://www.youtube.com/@TheAndreaCannon
