On this Elevate Support Call, Jason Lewis unpacks his evolution as a real estate investor and the mindset shifts that helped him build a $40M+ portfolio. He shares insights on choosing the right investment strategy, raising capital with intention, and aligning your business with your personal “why” for long-term peace and fulfillment.
Explore real estate investment strategies and personal growth insights with Jason Lewis, a seasoned investor.
Key Takeaways
· Align business decisions with your “big why” and lifestyle goals.
· Evaluate investment strategies (fix-and-flip vs. new construction) based on skills and risk tolerance.
· Build authentic relationships by adding value to others.
· Balance growth with contentment and long-term sustainability.
Jason Lewis’s Journey
· Grew up on a Kansas farm; family bankruptcy influenced risk awareness.
· Started with a motorcycle dealership, then house-hacked and built rentals in college.
· Survived 2008 by maximizing rental income via room shares.
· Current portfolio: $40–50M personally, $35M in partnerships; exited 1,000-door property management company.
· Invests in fix-and-flips, vacation rentals, and multi-state assets.
Investment Strategy Evolution
· Focused early on bootstrapping to limit risk; maintained 58.6% average leverage.
· Prioritizes stability: “Don’t effing lose it, be boring, be at peace.”
· Strategy now centers on risk management and protecting assets.
New Construction vs. Fix-and-Flip
· New Construction: scalable, repeatable (e.g., Pearl Street 4X), but slower and system-heavy.
· Fix-and-Flip: faster, more flexible, but less scalable and predictable.
· Choice depends on market, skillset, and risk comfort.
Capital Strategies & Partnerships
· Friends & Family: smaller checks, lower returns, high trust.
· HNW Individuals: larger capital, possible equity, expect more returns.
· Single Investor: simple funding, high control tradeoff.
· Choose based on control preference and personal alignment.
Relationships & Value Creation
· Focus on giving before asking; offer help to create genuine business relationships.
· Long-term success is rooted in connection, not transactions.
Mindset & Personal Alignment
· Know your drive—pursuing fulfillment vs. avoiding fear.
· Be a “lifestyle entrepreneur”: align business growth with personal joy and peace.
· Regular self-assessment is key to staying on track.
Action Steps
· Clarify your “big why” and assess current business alignment.
· Reevaluate investment and funding strategies based on risk and control preferences.
· Invest in building meaningful relationships in the industry.
· Continually realign operations with your long-term vision and lifestyle.
