In the world of real estate investing, it’s tempting to believe the hype: that every deal can be a winner if only you hold onto it long enough or apply the right strategies. But as Jay Conner explored with guest Ryan Cadwell in the insightful episode of Raising Private Money Podcast, true success in real estate requires discipline, honest self-reflection, and a willingness to walk away from deals that don’t truly serve your goals.
Ryan Cadwell’s background speaks for itself. With over 17 years of experience, more than $100 million in transactions, and a history that spans development, asset management, and property management, Ryan has lived through several market cycles—including the dizzying rise and painful aftermath of the 2008 crisis. It was clear from his conversation with Jay that Ryan’s approach is defined not by a relentless chase for deals, but by a careful, methodical process grounded in both data and emotional intelligence.
One of the central themes Ryan brought to the discussion is the danger of over-optimism in real estate. A pervasive myth in the industry is that real estate always creates wealth and that nearly any property, if held long enough, will yield a positive return. Ryan was quick to challenge this assumption, explaining that too many investors act without a proper plan, jumping into deals based on broad-stroke advice rather than a personalized investment strategy.
Perhaps Ryan’s most valuable insight was his emphasis on the power of saying “no.” He reflected on his early days working with his father on multifamily properties and realizing, through experience and after-the-fact analysis, that the real measure of skill is not in how many properties you buy, but in your willingness to walk away from those that don’t fit strictly defined investment criteria. In his view, investors should expect to say “no” to the vast majority of deals, knowing that only a select few will truly meet both their financial and strategic requirements.
Ryan also highlighted an often overlooked aspect of dealmaking—the art of listening. Too many investors, especially newer ones, fall into the trap of over-explaining or pitching their deals to brokers, lenders, or potential partners, rather than asking open-ended questions and genuinely listening to the responses. Ryan attributes much of his success to his ability to build rapport and trust simply by giving others space to share their needs and concerns. This approach, he believes, leads to more transparent negotiations and stronger, longer-lasting relationships.
The conversation also touched on the changing dynamics of the current market. Ryan pointed out that with rising interest rates and more frequent volatility, the game has shifted. He noted that some savvy investors are now focusing on acquiring real estate notes—essentially stepping into the shoes of the lender at a discount—rather than overpaying for inflated property values. This strategy requires its own caution, however, as the lending landscape is filled with complex, sometimes predatory terms. Ryan advised rigorous due diligence and a willingness to walk away from financing partners who do not inspire confidence.
Jay Conner, ever the champion of relationship-driven investing, reinforced Ryan’s points by stressing the necessity of diagnosing a potential partner’s or investor’s real needs before offering any solution. In their conversation, both men agreed that the true test of a good dealmaker is their ability to help others get what they want, without ever veering into salesy territory or rote scripts.
Ultimately, this episode delivers a message that every investor—new or seasoned—needs to hear. Discipline, honest self-evaluation, a strategic approach to listening, and the courage to walk away are all critical to long-term success. As Ryan and Jay reminded listeners, sometimes the best deal is the one you never do.
If you’re ready to move beyond the hype and start building lasting wealth on your own terms, this episode is a must-listen. Ryan Cadwell’s approach offers not just practical strategies, but a mindset shift that can help you avoid costly mistakes while forging a business—and a life—that doesn’t need an escape.
10 Discussion Questions from this Episode:
- Jay Conner asks about the “biggest lie” real estate investors believe. What do you think is the most dangerous misconception in real estate investing today?
- Ryan Cadwell emphasizes the importance of having a plan before investing. What steps should an investor take to build a solid investment plan?
- Ryan Cadwell discusses balancing optimism with realism when analyzing deals. How can investors best avoid falling into the trap of over-optimism?
- The episode highlights the value of listening more than talking in negotiations. Can you share a situation where listening led to a better investment outcome?
- Both speakers mention building trust with private lenders and investors. What strategies can help foster trust in investment relationships?
- Jay Conner references the idea that the biggest profit might come from deals you don’t do. How do you judge when walking away is the smartest move?
- Ryan Cadwell shares experiences working across asset classes. What are the unique risks and opportunities in single-family vs. multifamily or commercial real estate deals?
- The episode touches on recent trends such as investing by buying notes rather than properties directly. What’s your take on note buying as a strategy, and what risks should new investors be mindful of?
- What role does transparency play in long-term client relationships, according to Ryan Cadwell, and how can transparency help investors make better decisions?
- Reflecting on the advice shared about not rushing and adhering to predetermined investment criteria, what personal or observed examples do you have where patience led to a better investment?
Fun facts that were revealed in the episode:
- Ryan Cadwell revealed that, according to research, people may actually lie to themselves up to 200 times a day, especially when analyzing deals or making investment decisions. This self-deception can heavily impact real estate investing if not kept in check.
- Jay Conner shared a definition of malpractice he likes: “giving a solution before there’s a diagnosis”—and compared it to raising capital, emphasizing that you shouldn’t pitch investment opportunities unless you know the potential investor’s actual problem or needs.
- Ryan Cadwell believes that in real estate investing, the most money you can sometimes make is from the deal you don’t do. He pointed out that saying “no” to most deals is not only common but wise, as “yes” should be a surprise when carefully analyzing offers.
Timestamps:
00:00 Ryan’s unique real estate approach
06:17 Importance of Active Listening
08:24 Approaching lenders and brokers
12:13 Discussing investment opportunities
18:04 Choosing the right investment deals
20:53 Working with diverse real estate clients
24:50 Importance of buying real estate wisely
28:37 Buying undervalued property notes
30:29 Reviewing loan agreement terms
32:03 Connect with Ryan Cadwell:
33:11 Straight talk on investment mistakes
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