In this episode of the Generations of Wealth Podcast, Derek sits down with investor and lender Will Harvey to discuss hard money lending, private funds, underwriting risk, and the importance of staying humble in changing market cycles.
Will shares his journey from mortgage lending into flipping houses, apartment syndications, and eventually launching his own lending fund. Together, Derek and Will break down the realities of leverage, underwriting, investor protection, and why many people underestimate risk during strong markets.
This episode is packed with practical insight for anyone interested in private lending, raising capital, or building long-term wealth through real estate.
Watch the episode here
Listen to the podcast here
Overview
Will Harvey shares how he entered the mortgage industry after leaving college and quickly realized he preferred commission-based opportunities over traditional employment.
While working as a residential loan officer, he began purchasing rental properties and eventually transitioned into flipping houses and investing in apartment syndications.
Over time, Will realized he preferred the finance and capital side of real estate more than day-to-day operations. That realization led him to launch a friends-and-family investment fund focused on diversified real estate investments and eventually a dedicated hard money lending fund.
A major focus of the episode is risk management and underwriting.
Derek and Will discuss:
- The difference between traditional lending and hard money lending
- Why protecting investors should always come first
- How leverage can destroy inexperienced investors during market shifts
- Why first-position lending matters
- The importance of underwriting both the borrower and the asset
The conversation also explores:
- Market cycles and changing interest rates
- Lessons learned from the 2008 crash
- The dangers of “bull market genius” thinking
- Why humility matters in investing
- Warren Buffett’s investing philosophy and annual letters
Throughout the episode, both Derek and Will emphasize one consistent theme:
👉 Long-term success comes from protecting downside risk — not chasing hype.
Key Takeaways
- Hard money lending is primarily asset-based lending
- Investor protection should always come first
- Market cycles always change — nothing stays hot forever
- Overleveraging destroys investors during downturns
- First-position lending dramatically reduces risk
- Relationships matter more than transactions in lending
- Smart underwriting protects both borrower and lender
- Diversification helps smooth investment risk
- Humility is critical in real estate investing
- Warren Buffett’s principles apply directly to real estate
Relevant Topics Discussed
- Hard money lending fundamentals
- Underwriting and borrower analysis
- Real estate market cycles
- Raising private capital
- Syndications and investment funds
- Loan-to-value (LTV) strategies
- First-position lending protection
- Flipping houses and rental properties
- Risk management in real estate
- Warren Buffett investing philosophy
Why Should You Listen?
Listen to this episode if you:
- Want to understand hard money lending
- Are raising capital or considering a fund
- Want to become a smarter, safer investor
- Are worried about changing market conditions
- Want practical advice instead of hype
This episode is a reminder that:
👉 Great investors focus on protecting downside risk before chasing upside returns.
Important Links:
About Will Harvey
Will began his real estate career in 2015 as an award-winning residential loan officer at a national lender. Transitioning to direct investment, he founded his first real estate company in 2019 after building a personal portfolio of houses, rapidly gaining a comprehensive understanding of private syndications as both a limited and general partner.
This diverse, hands-on experience has been instrumental in his current role, where he adeptly manages multiple funds. Will’s unwavering commitment to shared success is underscored by his practice of personally investing alongside all partners in every venture. Will and his wife, Sarah, are based in the Richmond area and have two young boys. Will is a devoted Christ follower and is committed to using the resources he’s been blessed with to make Him known throughout the world.