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From $0 to $100 Million: Dale Wills Shares His Private Money Success Story


In the ever-evolving world of real estate investing, understanding how to effectively raise and leverage private money can make or break your success. In a recent episode of Raising Private Money, Jay Conner, an authority on private lending, sat down with Dale Wills, a real estate investor who has successfully raised over $100 million in private capital. Their discussion illuminated key strategies, and nuances between investing in single-family versus multi-family properties, and even explored ways to maximize your IRA for real estate investments.

 

The Jargon of Private Money: Making the Rules

 

Investing in real estate with private money is fundamentally different from traditional bank financing. Jay Conner initiated the conversation by stressing the importance of realizing that in the private capital realm, investors make the rules. Unlike conventional banking, where terms are rigid and largely non-negotiable, private money lending offers an open playground to set interest rates and define terms that best suit your investment needs.

 

Dale Wills highlighted that this shift in mindset is crucial. Many novice investors might initially feel intimidated by this newfound control and might be tempted to relinquish autonomy back to the lender. However, Dale emphasized that belief in one’s value proposition is vital. Standing firm and trusting in your offering can significantly boost confidence and, in turn, attract more private lenders.

 

Single-Family vs. Multi-Family Investments: Core Differences

 

One of the standout segments of the podcast was the discussion around the differences between investing in single-family homes versus multi-family apartments. Dale Wills, who specializes in single-family projects, provided some fascinating insights. While multi-family units offer value, they sometimes remain under-utilized due to evolving living conditions, such as consolidated households.

 

Dale’s focus on single-family homes, particularly entry-level, first-time buyer products, aligns well with current market dynamics. Even in economic downturns, the demand for these affordable housing options remains steadfast. Second or third-time homebuyers might hold off on purchasing during uncertain times, but first-time buyers typically continue to enter the market. This resilience makes the entry-level housing market a strategic focus.

 

Boosting Wealth with IRAs: A Hidden Gem

 

For many investors, leveraging retirement funds can be a game-changer. Jay Conner noted that a significant portion of his private lenders utilize their IRAs to invest, seeking better returns than traditional retirement accounts provide. Dale Wills backed this by highlighting Centra’s partnership with Equity Trust, a platform that facilitates the efficient transfer and investment of IRA funds into real estate.

 

Dale shared that transferring IRA funds for investment is straightforward and can offer significantly better returns compared to traditional investments like stocks or money markets. Real estate investments provide tangible assets that investors can see and feel, which is a considerable advantage over digital or paper assets which can sometimes feel intangible.

 

Helping First-Time Homebuyers

 

Another significant point of discussion was the various ways Centra helps first-time homebuyers. In today’s challenging economic climate, making homes affordable without compromising quality is paramount. Centra’s approach includes allowing employees to buy houses at cost, thereby helping them build personal wealth. 

 

Centra focuses heavily on entry-level housing, ensuring it is affordable while maintaining high standards. They also facilitate access to programs like USDA loans, which offer down payment assistance and interest-rate buy-downs. This multi-faceted approach makes homes more accessible and bridges the housing gap for both first-time homebuyers and empty nesters looking to downsize.

 

10 Discussion Questions Based on this Episode:

  1. Early Strategies:

How did Dale Wills initially raise private money for his real estate ventures, and what lessons can new investors take from his early strategies?

  1. Market Focus:

Why does Dale Wills prioritize first-time homebuyer properties and entry-level housing in the current market conditions over other types of investments like multi-family units?

  1. Faith and Business Integration:

Both Jay Conner and Dale Wills emphasize the importance of faith and family in their business decisions. How do these values influence their investment strategies and business practices?

  1. Independence from Banks:

How did Jay Conner shift from relying on bank loans to raising private money, and what are the advantages and challenges of this approach?

  1. Confidence in Fundraising: 

Dale mentioned that confidence plays a crucial role in raising private capital. What are some methods or practices that can help new investors build their confidence?

  1. Indirect Method:

Jay Conner employs what he calls the “indirect method” for raising private money by asking for referrals instead of directly asking for funds. How effective do you think this approach is, and could it be beneficial for others to adopt?

  1. Tax Advantages:

Dale explains the tax benefits that his employees and investors can gain by investing in real estate through mechanisms like IRAs. How do these tax advantages compare to other investment vehicles?

  1. Challenges and Recession-Proofing:

According to Dale Wills, why is entry-level housing considered more recession-proof compared to other types of real estate investments?

  1. Ethical Investment:

How does emotional and ethical investment (“believing in the person”) play a role in private lending, and how can this influence not only initial investment decisions but also sustained investor relations?

  1. Technological Adoption:

Dale Wills used modern technology to facilitate and streamline the transfer of IRA funds for investment. What role does technology play in making real estate investment more accessible, and what are some other tech innovations that could impact this industry?

 

Fun facts that were revealed in the episode: 

 

  1. Fake It Till You Make It:

Dale Wills once orchestrated an elaborate charade involving leaving a friend’s office space to impress a potential investor and secure a deal early in his career.

   

  1. Employee Wealth Program:

Dale Wills’ company allows employees to purchase houses at a cost to help them build personal wealth, highlighting a strong commitment to employee prosperity.

   

  1. Family Investment:

Dale convinced his father to transfer his IRA to invest in Dale’s projects, despite initially wanting to keep family and business separate.


Timestamps:

00:01 – Raising Private Money Without Asking For It

06:14 – Confidence in execution is key to success.

07:55 – Leverage past successes, fake it till made.

10:26 – Overcome fear of rejection; own real estate.

16:58 – Construction resilient in history, first-time buyers crucial.

20:01 – High fees in IRA, transfer for better return.

21:40 – Company motto: improve, affordable, quality, impact lives.

23:37 – Connect with Dale Willis:

https://www.CentraCapitalPartners.com












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What is Private Money? Real Estate Investing with Jay Conner

https://www.JayConner.com/MoneyPodcast

Jay Conner is a proven real estate investment leader. He maximizes creative methods to buy and sell properties with profits averaging $67,000 per deal without using his money or credit.

What is Real Estate Investing? Live Private Money Academy Conference

https://youtu.be/QyeBbDOF4wo

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https://www.youtube.com/c/RealEstateInvestingWithJayConner

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Listen to our Podcast:

https://www.buzzsprout.com/2025961/episodes/15604084-from-0-to-100-million-dale-wills-shares-his-private-money-success-story

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