Raising Private Money with Jay Conner

For real estate investors striving to build substantial wealth, there’s often a belief that the secret lies solely in finding the right deals or accessing more capital. But as shared in the episode "Become The Architect Of Your Own Wealth With Emilio DiSpirito IV" on Raising Private Money, true success often comes down to mindset, relationships, and the willingness to think—and act—differently.

Jay Conner, the Private Money Authority, introduced Emilio DiSpirito IV as someone who doesn’t just think outside the box—he reconstructs the box entirely. Emilio’s track record speaks volumes: over $750 million in real estate closed, nearly 50 homes flipped, major development projects, and one of Rhode Island’s top luxury real estate brands. His unique perspective as not only an agent but also an investor, advisor, and developer distinguishes his approach in empowering others to create wealth.

Thinking Like a Wealth Architect

What sets Emilio apart, as discussed with Jay, is his commitment to acting as a true advisor. Many in real estate are purely transactional, focused on closing deals rather than fostering long-term relationships. Emilio advocates for a different model: be the expert who helps clients sidestep pitfalls and seize the right opportunities. He recounts instances of talking clients out of deals that didn’t serve their long-term interests, highlighting the value of wisdom over mere knowledge. Investors are willing to pay for experience that saves them time, money, and stress.

This advisor-first mentality also leads to deeper relationships. Emilio’s ideal clients are those who value expertise and are ready for a partnership based on trust, mutual respect, and shared vision. Such relationships yield more than transactions—they generate referrals, repeat business, and lasting impact.

From Zero Experience to Raising Capital

A common question among new investors centers on raising private money. Emilio and Jay both emphasize that success here is not about chasing after people with wealth, but about cultivating relationships and proving reliability. For those starting without connections, Emilio recommends aligning with experienced partners, even offering to help established developers or investors for free initially. This builds credibility and opens doors to private money conversations rooted in trust, not desperation.

Jay’s philosophy complements this approach: focus on serving, not selling. His experience with 47 private lenders—many of whom have stayed with him for decades—demonstrates the power of prioritizing relationships. Investors should see themselves as educators; very few private lenders even know such opportunities exist until someone trustworthy introduces them to the concept.

Busting Myths and Leveraging ‘Lazy Money’

A persistent myth in real estate investing is the idea that debt—especially private money—is something to be feared. Emilio counters that leveraging private money, even at the risk of break-even or slim profits early on, is an investment in expertise and future earnings. The experience and confidence gained far outweigh temporary profits.

Additionally, many believe private lenders must be ultra-wealthy. Jay challenges this notion by focusing on “lazy money": funds sitting idly in savings or retirement accounts. With a little education, everyday people become empowered to participate in private funding, creating a win-win dynamic.

Resilience and Mindset: The Foundation of Success

Throughout their conversation, both Emilio and Jay stress that setbacks and failures are inevitable, but they are crucial for growth. Resilience isn’t just an admirable trait—it’s a requirement. Emilio’s ability to sell previously unsellable properties by repositioning strategies and targeting new buyer personas underscores the importance of creativity and adaptability.

Moreover, faith, discipline, and self-improvement round out the foundation. Emilio’s openness about his faith journey and commitment to personal growth remind listeners that success isn’t just about financial achievement--it’s about becoming the best version of oneself in all aspects of life.

Your Journey as a Wealth Architect

To step into the wealth architect role, Emilio advises listeners to believe in themselves and avoid being limited by the doubts of others. Align with inspiring mentors, surround yourself with positive influences, and never underestimate the power of starting—imperfectly, perhaps, but with determination.

At its core, the message is clear: when you focus on building real relationships, embrace a learning mindset, and boldly take strategic risks, you move from merely seeking wealth to actively designing it. For anyone wanting to construct a future on their own terms, the conversation with Jay Conner and Emilio DiSpirito IV offers a practical, inspiring blueprint.

10 Discussion Questions from this Episode:

1. Jay Conner highlights mindset as the foundational step to successfully raising private money, emphasizing service over selling. In what ways has your mindset either helped or hindered your ability to attract investment or close deals?
2. Emilio DiSpirito IV draws a strong distinction between being an advisor and being an agent, focusing on expertise and long-term relationships. How would adopting an advisor’s mentality change the way you interact with clients or partners?
3. Emilio DiSpirito IV credits much of his success to building a network of “power players.” What practical steps have you taken—or could you take—to build a high-value network in your career?
4. For those new to private money, Emilio DiSpirito IV recommends seeking mentorship, even working for free, to build credibility. Would you consider working for experience over immediate compensation? Why or why not?
5. Both Jay Conner and Emilio DiSpirito IV assert the importance of investing in relationships before deals. What are some concrete ways you nurture professional relationships so they lead to meaningful, long-term results?
6. Jay Conner introduces the concept of “lazy money” and stresses the value of educating potential lenders about private lending. How do you (or could you) approach educating others who have never heard of private money opportunities?
7. Emilio DiSpirito IV disputes the belief that “debt is bad,” arguing that leveraging debt can provide valuable learning and growth. How do you differentiate between good debt and bad debt in your investment strategy?
8. Emilio DiSpirito IV shared his process for repositioning and marketing difficult-to-sell properties, including using buyer personas and AI tools. Have you repositioned a stagnating asset for sale? What strategies worked for you?
9. Both Jay Conner and Emilio DiSpirito IV talk about faith, discipline, and mindset as essential to success. How do your personal values or routines align with your professional ambitions and outcomes?
10. Emilio DiSpirito IV advises listeners to develop self-belief and ignore doubts from others, referencing “The Pursuit of Happyness.” Can you share a time when you had to overcome skepticism—either internal or external—to pursue your business goals?

Fun facts that were revealed in the episode: 

1. Deal-Making Powerhouse: Emilio DiSpirito IV has personally closed over $750 million in real estate transactions and flipped nearly 50 homes, contributing to the creation of one of Rhode Island’s top luxury real estate brands.
2. Reverse Psychology in Real Estate: When tasked with selling homes that had sat on the market for over 200 days, Emilio DiSpirito IV shifted the strategy by identifying a new buyer persona, staging properties, and even increasing prices—leading one home to sell in just one day! 
3. "Lazy Money" Insight: Jay Connor and Emilio DiSpirito IV agree that raising private money isn't just about targeting the wealthy. Often, it's about educating “regular” people who have “lazy money”—funds sitting stagnant in savings or retirement accounts—about private lending opportunities.

Timestamps:

00:00 Meeting Emilio DiSpirito

04:21 Creating real estate inventory

09:38 Exploring alternative lending options

10:49 Focusing on relationship-building

15:44 Using private money for investments

19:16 Slow housing market in Rhode Island

21:24 Adjusting marketing strategy

24:25 Using AI for real estate listings

28:20 Personal growth and helping others

32:07 Inspiration from personal struggles

36:00 Connect with Emilio DiSpirito IV 

https://www.instagram.com/emiliodiv/

36:46 The Curiosity Opener script giveaway 

https://www.JayConner.com/Scripts  

37:37 Sharing investment insights from Emilio  

Con

On the "Raising Private Money" podcast, Jay Conner sat down with self-storage entrepreneur Bree Hartman for a deep dive into how everyday investors can break into the lucrative world of self-storage. Bree’s journey from an accidental landlord to managing a $6 million storage portfolio is both inspiring and practical — filled with actionable steps anyone can follow to succeed in this overlooked real estate niche.

From Accidental Rental to Storage Empire

Bree Hartman didn’t start out aiming for a real estate empire. Like many, she worked a regular W2 job and initially stumbled into real estate by renting out her first home. This standard entry led to all-too-common headaches — from tenant troubles to property damage — making her realize traditional rentals didn’t offer the lifestyle freedom she wanted.

The turning point came when Bree learned about self-storage through podcasts. What caught her attention was its simplicity: no toilets, no tenants, fewer hassles. Motivated, she attended a self-storage conference in Las Vegas while pregnant, determined to find and buy her first facility before her baby arrived. It took about nine months, but her persistence paid off with a successful acquisition in Louisiana, despite being a completely remote market for her.

Early Lessons and Avoiding Landmines

One of the biggest hurdles Bree faced was dealing with imposter syndrome and financial limitations. She teamed up with two partners she met at a conference to purchase their first $3 million property using a Small Business Administration (SBA) loan. This maneuver required only 10% down, making large deals accessible without deep pockets.

Bree emphasizes that careful, thoughtful partnerships are essential. Clarity around responsibilities, risk, and tough contingencies such as death, divorce, bankruptcy, or unfulfilled duties ensures longevity and mutual trust within the partnership. She and her partners spent months with an attorney crafting these agreements, a decision she credits for the successful, ongoing nature of their professional relationship.

The Storage Freedom Formula

A frequent question Bree receives is how she manages facilities across various states while working from home. Her answer is the “Storage Freedom Formula,” which revolves around smart operations and systems management. She describes three operational models:

1. DIY Approach: Some owners, like a firefighter she mentions, self-manage their properties remotely, spending just a handful of hours each week.
2. Hybrid Model: This is Bree’s preferred method and what she teaches her students. It involves a local “boots on the ground” person for physical tasks, combined with a remote call center trained to handle sales and tenant interactions. The result is near-hands-off management while ensuring quality service.
3. Third-Party Management: Suitable for larger facilities, this approach uses professional property managers but still requires oversight to maintain standards and profitability.

Technology is central to successful remote management. Prospective tenants can rent and pay online, receive instant gate and unit access codes, and move in without on-site staff. Even rental offices are repurposed for additional income streams, such as leasing to local businesses.

Multiple Revenue Streams and Value Adds

Self-storage is more than just renting units. Bree highlights how creativity and attention to detail can unlock multiple revenue streams: climate-controlled and non-climate units, RV and boat storage, cell towers, tenant insurance, billboards, U-Haul partnerships, and dynamic pricing based on demand. These add-ons not only increase monthly income but also significantly boost the facility’s value. Her approach often leads to rapid appreciation and opportunities to refinance or sell for substantial profits.

Finding Deals Others Miss

While many investors focus on listings and brokers, Bree is a fierce advocate for crafting custom off-market deal lists. She and her students scour Google, Secretary of State filings, and white pages to directly contact mom-and-pop owners in overlooked secondary or tertiary markets. Consistently reaching out and building relationships with these owners opens doors to seller financing and creative deal structures.

One success story involved a student landing a 10,000 square-foot Texas facility with just $9,000 down using seller financing, adding value through billboards and U-Haul rentals, and setting themselves up for a significant equity gain within a few years.

Is It Too Late for Self-Storage? Absolutely Not.

Despite a boom in new builds in some metropolitan areas, Bree notes that opportunity abounds in smaller markets with steady demand and less competition from giant REITs. The “four Ds” — death, divorce, downsizing, and disaster — drive resilient, recession-resistant demand for storage. Plus, the ongoing wave of retiring baby boomer owners means motivated sellers who may prefer passive income via seller financing.

Taking Action: The Real Difference-Maker

Ultimately, Bree Hartman’s most powerful advice is simple: learn quickly, take action, make offers, and follow up relentlessly. She notes that consistent action — even if imperfect — beats endless research and overthinking. Deals are not won by those who wait, but by those who actively put themselves out there, offer solutions, and build relationships.

For anyone looking to get started in self-storage, the key is to leverage partnerships, master remote operations, and pursue creative off-market deals. With the right mindset and systems, a lucrative and flexible investing business is within reach.

10 Discussion Questions from this Episode:

1. How did Bree Hartman's accidental entry into real estate investing shape her approach to building a self-storage portfolio?
2. What are the advantages and disadvantages of partnering with others on your first commercial real estate deal, according to Bree Hartman's experience?
3. How does seller financing work in self-storage acquisitions, and why does Bree Hartman believe it creates win-win outcomes?
4. What systems and frameworks make it possible to manage storage facilities remotely, as described in Bree Hartman's "storage freedom formula"?
5. Discuss the various revenue streams in self-storage that Bree Hartman mentioned. Which do you think has the most potential for scalability?
6. Why does Bree Hartman focus on third and fourth-tier markets instead of competing with large REITs in major metropolitan areas?
7. How does Bree Hartman find off-market deals, and why does she believe creating a custom owner list is more effective than relying on brokers or listed properties?
8. What are the psychological or mindset barriers Bree Hartman described when moving from residential to commercial storage facilities, and how did she overcome them?
9. Why does Bree Hartman stress the importance of making offers—even low ones—to storage facility owners?
10. According to the episode, what separates action-takers from those who remain stuck when trying to buy their first storage facility?

Fun facts that were revealed in the episode: 

1. Accidental Empire
   Bree Hartman started her real estate journey by accident—she simply rented out her first home, which opened the door to building a self-storage portfolio now worth over $6 million.
2. Remote Control
   Bree Hartman successfully manages storage facilities across several states—including Louisiana, the Carolinas, Tennessee, and Texas—all while living in Sacramento, California. Thanks to smart systems and the "hybrid model," she can run her business from home and spend more time with her daughter.
3. Eight Ways to Make Money
   Self-storage isn’t just about renting out simple lockers. Bree Hartman revealed that her facilities have as many as eight different revenue streams—ranging from traditional storage units to cell towers, office rentals, U-Haul partnerships, and tenant insurance upsells.

Timestamps:

00:00 Bree Hartman's real estate journey

04:55 Learning to finance deals

08:46 Learning through action and questions

11:01 Managing multiple remote facilities

13:55 Automated storage unit systems

18:22 Finding off-market storage deals

20:31 Real estate investment strategy

23:41 Predicting future market opportunities

27:52 Encouraging persistent follow-ups

30:44 Securing a property in Texas

33:56 Connect with Bree Hartman:

916-579-7209  

Self-Storage Calculator:  

https://www.selfstorageschool.com/calculator

34:46 Taking Action in Real Estate  

 Connect With Jay Conner: 

Private Money Academy Conference: 

https://www.

***Guest Appearance

Credits to:

https://www.youtube.com/watch?v=HfJWsqaa-Ug                                     

“How to Raise Private Money for Real Estate Investing | Jay Conner E33.”

https://www.youtube.com/@iamkeithandrews  

If you’re a real estate investor—or aspiring to become one—you know that access to funding can make or break your deals. On the “Raising Private Money” episode with Jay Conner and Keith Andrews, listeners get an in-depth look at the strategies and mindset shifts that set successful investors apart, especially when it comes to raising private capital.

Understanding Private Money vs. Hard Money

Jay Conner, widely recognized as "The Private Money Authority," shares his journey in real estate since 2003 and the pivotal moment that led him away from traditional financing. Like many investors, Jay started by working with local banks and mortgage companies. But in 2009, when his trusted line of credit was abruptly revoked, he realized he needed a different approach.

That’s where private money entered his world. Jay distinguishes private money from hard money—something many investors confuse. Hard money typically comes from brokers who manage a fund and add origination fees and higher interest rates on top. Private money, on the other hand, is direct: it's a transaction between an investor and an individual lender, with no intermediary. This makes private money not only faster but also cheaper, as it eliminates costly fees.

Who Can Be a Private Money Lender?

According to Jay, nearly anyone can become a private money lender. His roster includes retired teachers, police officers, civil service workers, and even minors who have received inheritances. The core trait is having “lazy money”—capital or retirement funds sitting in low-yield accounts that could work harder elsewhere. By offering these individuals a secure way to earn a higher return, investors can build a robust network of private lenders.

Structuring Deals and Protecting Lenders

One of the significant concerns for both investors and lenders is security. Jay is clear: he never borrows unsecured funds, structuring each deal to protect the lender as much as a traditional bank would be protected. Each lender receives a promissory note and either a deed of trust or a mortgage, depending on the state. This gives them legal recourse should anything go wrong.

A typical arrangement might offer an 8% annual return, fully collateralized by the property as security. The lender is also named as mortgagee on the insurance policy and additional insured on the title insurance policy. In the rare event of an urgent need for liquidation, lenders can invoke a 90-day call option, allowing them to give notice and have their capital returned ahead of schedule. Jay’s thorough approach helps build trust and peace of mind with his private lenders.

Finding Private Lenders: Your Warm Market and Beyond

Jay emphasizes that most private lenders will come from your existing network—people you know from your local community, professional circles, and even your church or golf club. These are individuals who already trust you and may be unhappy with their current returns on savings or retirement accounts. For growth, it’s essential to expand your network, using groups like Business Networking International, SCORE, and local business organizations.

Another source of lenders is those already invested through self-directed IRA companies. Companies like these frequently host networking events where investors—who are already familiar with real estate lending—can connect with those seeking capital.

The Standard Deal: Keeping It Simple and Se

***Guest Appearance

Credits to:

https://www.youtube.com/watch?v=hQUXwHjkT-0&t=250s                                    

“How to Raise Private Money for Real Estate Deals (w/ Jay Conner) [TJP Ep29].”

https://www.youtube.com/@Thejourneypod/ 

On a recent episode of the Raising Private Money podcast, real estate investing heavyweight Jay Conner sat down with Leo Young for a wide-ranging discussion about the critical art of raising private money. Their conversation illuminated not just the mechanics of private funding in real estate, but also the mindsets and systems that lead to sustainable, scalable success. Whether you’re a seasoned investor or just getting started, this episode offered a masterclass in funding strategy.

Transforming Obstacles into Opportunity

Jay Conner has built an impressive reputation over two decades, rehabbing over 500 homes and transacting more than $100 million in deals. But his journey took a pivotal turn after the 2008 financial crash, when traditional banks pulled his credit lines, and he was forced to rethink his approach. This adversity led him to discover the power of private money—a strategy that allowed him, within just 90 days, to raise over $2 million in new capital, entirely free from the restrictions and demands of banks or credit.

For Jay, the transition to private money wasn’t just about survival; it became the defining catalyst for his long-term business growth and transformed the way he looked at real estate investing as a whole. He attributes his ability to consistently close deals—never missing out for lack of funds—to building and nurturing relationships with private lenders.

Debunking the Myth: "The Money Will Show Up"

A recurring theme in the conversation was Jay’s frustration with the tired real estate trope that if you lock down a good deal, the money will magically appear. Both Jay and Leo agreed that this advice is not only unhelpful but also sets up new investors for unnecessary stress. Instead, Jay advocates for flipping this narrative: get the capital lined up before you hunt for deals. This approach gives investors confidence, negotiating power, and the ability to make offers rapidly, which is crucial in competitive markets.

There’s more capital available—especially post-2020—than there are viable real estate deals. That means investors who proactively build relationships with private lenders hold a significant edge.

A Mindset Shift: From Borrower to Opportunity Provider

Jay discussed the crucial mental shift he made—and now teaches others—which is moving from a mentality of “asking for a loan” to “offering an opportunity.” For most people, the default is to assume that the person with the money makes all the rules. Jay turned this on its head by taking control: setting terms, acting as his own underwriter, and educating potential private lenders about the benefits and security they receive by investing in his projects.

He views his role as more of a teacher than a beggar or persuader. Most of his 47 private lenders didn’t even know what private lending was until he introduced them to the concept. His approach is methodical and based on service—helping regular people put their “lazy money” (funds sitting idle) to work at attractive, secured returns.

Separation of Offer and Deal

A key nuance in Jay's approach is the importance of separating the conversation about the general private lending opportunity from discussing specific deals. He recommends educating potential lenders about the overall offering first. Once they’re on board, only then does he bring them individual deals that meet strict criteria—never asking them outr

In a candid and eye-opening episode of the “Raising Private Money” podcast, Jay Conner welcomes Carter Lane, CEO and founding partner of Unified Wealth, to share powerful insights about self-directed IRAs and why they’re a vital tool for anyone seeking true control over their financial future.

For too long, conventional wisdom about retirement has convinced everyday investors that Wall Street knows best. Most Americans place their faith—and life savings—in traditional vehicles like IRAs and 401(k)s, trusting that stock market growth and a menu of mutual funds will be enough to secure a comfortable retirement. But Jay and Carter challenge this narrative head-on, urging listeners to rethink the risks and question who really benefits from the status quo.

Carter Lane brings more than two decades of real estate and private investing experience to the conversation, but his passion for this mission is deeply personal. After witnessing his own mother lose her retirement savings in the financial crash of 2008, Carter made it his mission to protect others from a similar fate. He has since helped thousands of investors move more than $100 million into self-directed retirement accounts, empowering them to invest in what they understand—like real estate, private lending, and other tangible assets.

Jay Conner reflects on his own journey, explaining how the 2008–2009 banking crisis abruptly cut off his access to traditional financing. This forced him to uncover the world of private money and, more importantly, the unique advantages of self-directed IRA companies. These experiences frame the day’s discussion: What exactly are self-directed IRAs, and why are they an essential tool for anyone who wants to build wealth outside Wall Street?

Carter lays out the basics for those new to the concept. A self-directed IRA is a qualified retirement plan—just like a traditional IRA or 401(k)—but with an important difference: The account holder is in control. Instead of being limited to a strict list of stock-based investments, individuals can roll existing retirement funds into a self-directed IRA and invest in a much broader range of assets, such as real estate, private notes, and more. This control allows for greater diversification and returns, all while maintaining the same tax-advantaged status as conventional accounts.

The podcast discusses why so few people know about these options. As Carter explains, the self-directed IRA has actually been part of the tax code since the 1970s, but large brokerage firms and financial advisory businesses have little incentive to promote it. Traditional custodians don’t profit when their customers move funds into self-directed accounts, so they rarely educate their clients about them. Jay observes that most investors, even savvy real estate professionals, only discover self-directed IRAs when someone takes the time to educate them about private lending.

The conversation makes it clear that relying exclusively on Wall Street comes with hidden costs. Not only do investors give up control, but they are also subject to significant management fees, which Carter points out can erase as much as 63% of total gains over the life of an account. More importantly, market swings beyond an individual’s control can destroy carefully built savings overnight.

Transitioning to a self-directed IRA, however, is remarkably straightforward. Carter Lane’s firm helps clients roll over funds from other retirement plans—whether an old 401(k) or a traditional IRA—into a new account that’s attached to a checking account, providing what he calls “checkbook control.” This means clients have direct access to their funds for investing, without middleman approval or extra fees. The only IRS limitations are investments in collectibles and life insurance, leaving investors free to pursue real estate, notes, or any asset they believe in.

For high-level real estate investors and business owners, Carte

In a recent episode of Raising Private Money, Jay Conner welcomed Nic DeAngelo, founder and CEO of Saint Investment Group, for a deep dive into what it really takes to build wealth in today’s economic climate. With years of experience and a portfolio surpassing $200 million, Nic is a recognized figure in real estate known for his data-driven investment strategies. Their conversation unpacked critical perspectives on inflation, Wall Street, and the future of smart investing.

Navigating the Age of Inflation

Nic DeAngelo started by explaining an unsettling outlook: we are likely in the early stages of a long-term inflationary period. He pointed to America’s unprecedented government spending and ballooning national debt as major drivers. Both Republican and Democratic administrations, Nic noted, have participated in massive fiscal expansion, leading to a scenario where, for the first time in history, interest payments on the national debt could soon exceed even programs like Social Security. Combine that with an aging, risk-averse baby boomer population and ongoing money printing, and it's clear why inflationary pressures are here to stay.

This inflation isn’t just an abstract economic trend—it has tangible impacts on everyday Americans, eroding wage gains and increasing the cost of living. Nic emphasized that so far, neither political party has staged a serious intervention to address the root causes, and both raising taxes and cutting spending present tough, politically unpalatable options.

What Wall Street Is Getting Wrong

A central theme of the episode was Nic DeAngelo’s take on Wall Street’s current state. He argued that Wall Street is fundamentally broken for everyday investors. Where stock market diversification once gave Main Street a fair shot, the number of public companies has dropped by over 40% since the 1990s, and more promising companies are choosing to stay private, leaving public markets top-heavy and driven by a handful of major tech firms. This has skewed returns and made it harder for investors to rely on Wall Street for consistent growth.

Nic highlighted another concern: the market’s addiction to hype. With exuberance around artificial intelligence and other trends, prices have surged well above underlying value by most metrics. It's no longer a level playing field, and timing the market has become riskier than ever.

Why Real Estate Remains the Solution

Against this backdrop, Nic DeAngelo believes that real estate, and specifically private lending secured by real estate, stands out as a superior wealth-building tool. His conviction rests on classic economic fundamentals like supply and demand. The U.S. is short millions of single-family homes, and demand remains consistent, creating lasting pricing power and stability. While this shortage has made home buying more difficult for first-time buyers, it also means strong, long-term prospects for real estate investors.

What sets Nic apart is his approach to investing in the debt—lending against real estate rather than direct ownership. He maintains that this strategy delivers exposure to the asset class’s upside while avoiding many operational headaches. It also provides better returns than today’s traditional bonds, revitalizing the fixed-income portion of an investor’s portfolio at a time when stocks and bonds are moving in tandem, undermining the old 60/40 allocation model.

The Future: Opportunity Amidst Uncertainty

Looking ahead three to five years, Nic DeAngelo predicts that smart investors who position themselves correctly in private real estate debt and U.S. manufacturing will outperform those clinging to Wall Street’s conventional wisdom. He stressed that the largest investment groups have already moved significant resources away from stocks and bonds and into alternative assets, especially real estate.

He also addressed the role of technology, particularl

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

In the modern entrepreneurial world, “working harder” is often worn as a badge of honor. But if you’re trapped in a never-ending cycle of doing everything yourself, even in a highly profitable business, you’re likely feeling the stress and missing out on the freedom you thought entrepreneurship would provide. The recent episode of “Raising Private Money” with Jay Conner and Josh Thomas, founder of VAIQ and host of the “Leverage Everything” podcast, unpacks why doing less (the right way) is not only desirable but essential for growth and happiness.

The Real Bottleneck: It’s Not Money or Deals

For many real estate investors and entrepreneurs, the supposed bottleneck is usually either finding deals or raising money. But as Jay and Josh illuminated, the real limiting factor is often the refusal to build the right team and implement effective systems. Both speakers share candid personal experiences from their early days—Jay recalling nights when the stress bled into family life, and Josh reflecting on patterns he’s seen with thousands of entrepreneurs in over 30 industries.

This stubborn “lone wolf” approach inevitably extracts a toll: time, mental energy, relationships, and ultimately, money. What’s harder to spot than monetary losses are the hidden costs of stress, lost opportunities, and burnout. As the episode makes clear, sole operators eventually hit the ceiling—where the only path forward is to learn how to leverage time, talent, and systems.

The Mindset Shift: Delegate and Disappear

For Jay, a pivotal “wake-up call” came after realizing financial success wasn’t fulfilling when it came paired with overwhelm. His commitment thereafter: dictate, delegate, and gradually step away from daily operations. This philosophy doesn’t mean abandoning the business or lowering standards; it’s about smartly putting people and systems in place so that the business serves you, rather than the other way around.

Josh brings two decades of practical experience to the discussion, warning against the mirage that hiring alone solves all problems. He explains the critical need for foundational systems and clarity on desired outcomes—before seeking to delegate tasks. Without that clarity, bringing on help (remote or otherwise) only risks amplifying inefficiency. Entrepreneurs must first document and refine processes so new hires become force multipliers, not added headaches.

The Four-Box Framework for Trustworthy Business Relationships

Beyond operational efficiency, the episode also covers Josh’s insightful framework for assessing business relationships—a model directly applicable for those seeking or offering private money, but also valuable for leaders overseeing teams, partnerships, or even personal interactions. Josh outlines four sequential “boxes” that must be checked for a healthy, productive engagement:

1. Integrity: Is the person trustworthy? All other considerations are irrelevant without this foundational element.
2. Competence: Do they know what they’re doing? No matter how much you like or trust someone, if they lack skill, the partnership is doomed.
3. Stewardship: Will they be responsible caretakers of your resources, whether that’s money, time, or energy?
4. Deal Details: Only after the first three are in place do the specifics of the opportunity or relationship truly matter.

This model flips the common pitch-centric approach. True leverage—whether with employees, partners, or lenders—flows from trust and capability, never just numbers.

Pulse: Bringing High Performance to Virtual Teams

Josh also expands on “Pulse,” his process-driven system modeled after elite athletes. Like Tiger Woods or Michael Jordan, top performers rely not on raw hustle, but consistency, constant measurement, coaching, skill refinement, and relentless execution. By instilling these traits into remote teams (especially with affordable int

In the world of real estate investing, two critical questions dominate most investors’ minds: How do I find the deals, and where do I get the money? Jay Conner, known as the Private Money Authority, explores both on his podcast “Raising Private Money.” In a recent episode, Jay sits down with Andrew Becker to dive deep into one of the most overlooked yet lucrative lead sources in real estate: the probate niche.

Andrew Becker isn’t your average real estate operator. After beginning his career in one of the most systemized and high-stakes environments possible—supporting the U.S. Air Force’s nuclear enterprise in the Pentagon—Andrew brought his obsession with process and systems into real estate. Over the past 13 years, he has built and scaled a high-performance operation, eventually discovering that probate leads consistently produced seven-figure revenues for his businesses.

So, why probate, and what makes Andrew’s approach different?

The Power of Focusing In

Andrew’s journey into the probate niche didn’t happen by accident. Initially managing dozens of lead sources, he and his team realized that their deal flow was being throttled by a lack of focus. Instead of going a mile wide and an inch deep, Andrew looked at the data and decided to zero in on what was actually working. Probate leads rose to the surface, consistently producing high-quality, motivated sellers and, more importantly, reliable profits.

This is grounded in the Pareto Principle—the classic 80/20 rule—in which 80% of your results come from 20% of your efforts. For Andrew, probate was that critical 20%.

Understanding Probate vs. Pre-Probate

A common point of confusion for many investors is the difference between pre-probate and probate leads. Andrew explains that pre-probate refers to instances where someone has passed away, but the legal process hasn’t yet been initiated. These are flagged by death certificates or obituaries. In contrast, probate is the formal legal process that begins once a “petition for probate” is filed in court.

Crucially, Andrew’s system doesn’t target pre-probate leads out of respect for grieving families who may not be ready to make decisions about their inherited property. Instead, he waits for the formal opening of a probate case, which signals that the family is ready to begin settling the estate. This approach is both more ethical and more effective, leading to better conversion rates and less resistance.

What is a Probate “Machine”?

The heart of Andrew Becker’s success is his systematized approach—what he calls the “probate machine.” Across the more than 3,000 counties in the U.S., new probate cases are opened every single day. Andrew teaches investors how to pull these probate records themselves, directly from the courthouse, instead of relying on slow or outdated list providers. This gives investors a real competitive edge, allowing them to reach out to personal representatives (PRs) as soon as a case is filed.

What sets Andrew’s system apart is its dual focus on both the property and the probate process itself. By educating themselves on probate, investors can truly help overwhelmed PRs navigate the complex and often confusing world of estate settlement. This high-value, service-oriented approach fosters trust and positions investors as allies, not just opportunistic buyers.

The Real Mindset Shift

Many real estate professionals approach probate leads as they would any other distressed seller—just another address. Becker advocates for a more nuanced and compassionate approach. Personal representatives are not typical home sellers. They’re often overwhelmed, emotionally drained, and juggling personal obligations on top of managing an estate. By leading with genuine value—offering probate checklists, resource guides, and introductions to trusted probate attorneys—investors can build authentic relationships and differentiate th

When most people think about real estate investing, the first images that come to mind are often an endless stack of contracts, house tours, negotiations, and the hunt for the best properties. But beneath the surface of this transactional world lies a powerful truth: real estate is still very much a people business. This principle is at the heart of the podcast episode.

The episode features Jarrod Frankum, an investor, realtor, and founder of a family-run real estate business, as he sits down with Jay Conner to break down the real journey behind private money, deal-making, and why relationships are the ultimate currency for success.

The Unexpected Path to Private Money

One of the most compelling aspects of Jarrod Frankum’s story is how his path into private money wasn’t something he planned. He didn’t approach investing with a wealthy background, a trove of connections, or a pile of capital. Instead, his journey began with sharing excitement about his business with people he already knew—without any intention of pitching for funds. What happened next signaled a core reality for real estate entrepreneurs: often, genuine enthusiasm and consistent action attract others who want to participate.

By being open about his goals, Jarrod Frankum found himself approached by someone willing to partner and supply the capital he needed for his very first deal. Later opportunities arose through a mixture of referrals and organic connections at investor meetups. The lesson is clear—building trust and communicating authentically about what you are doing can be a magnet in itself. Importantly, many of his early deals were funded by those who believed in him, not just the numbers.

Referrals and Reputation: The Real Deal-Makers

Throughout the episode, Jarrod Frankum repeatedly emphasizes that referrals have played a pivotal role in sourcing private lenders. Instead of chasing every dollar, he focused on being active, visible, and reliable in local investor networks and professional circles. Delivering on promises, managing deals well, and communicating clearly with partners generated a network effect; each successful transaction made the next connection easier.

Jay Conner reinforces this pattern with his own experience, having also raised capital through personal contacts, specifically through shared communities like churches. Being known as someone who does what they say and values transparency becomes much more important over time than any marketing gimmick or pitch. Deals come and go, but reputation endures and pays dividends as word spreads organically among peers.

Transparency: The Ultimate Safeguard

Mistakes in the private lending world can be costly, and Jarrod Frankum notes that the biggest he’s observed among peers is masking risks or being less than forthright with partners. Huge issues arise when people use new funds to patch over old mistakes or don’t present a realistic picture of the numbers. Instead, Jarrod Frankum’s approach is to front-load honesty: he shares comps, renovation budgets, and even points out risks with each deal. Trust is built on full disclosure, and if potential partners walk away, that’s better than jeopardizing anyone’s capital. In his view, always being upfront ensures that only the right kind of people, with the right expectations, get involved.

Preparation Beats Panic

A recurring theme is the importance of finding money before stumbling into desperate need. Too often, novice investors are told to get a deal under contract and assume the money will follow. The reality is that having funding lined up enables investors to act quickly and confidently. This confidence, in turn, makes it easier to secure more deals, grow the business, and help more people.

Getting Started: Mindset and Intentional Action

For those just starting out, Jarrod Frankum stresses the importance of understanding both what you'