In a recent conversation, Dustin Miles sat down with Madhavi Jain, president and wealth strategist at Think Outside the Stocks and founder of Connected Capital Community.
Their conversation covered Madhavi’s unconventional path to wealth building, the role of financial strategy in creating long-term stability, the value of collaborative due diligence, and the opportunities and challenges facing multifamily investors in today’s market.
A Journey Built Through Setbacks and Reinvention
Madhavi describes her story as an “uncommonly common” one—a journey shaped by hard work, unexpected setbacks, and the need to start over more than once.
After immigrating to the United States, Madhavi and her family worked to build a new life from the ground up. Then came the 2008 financial crisis. Both she and her partner lost their jobs while their family was living in California and preparing for the arrival of another child.
The family eventually relocated to Austin and began rebuilding.
Several years later, in 2015, Madhavi stepped away from a successful consulting career because of health challenges. With her family’s financial future in mind, she began exploring alternatives to a traditional career path and looked more closely at real estate, syndications, and other financial strategies.
That exploration eventually led her to think about wealth building more broadly—not as a single investment or product, but as a combination of strategies designed to create greater financial flexibility and stability.
Understanding the Infinite Banking Strategy
One of the strategies discussed during the conversation was infinite banking, which generally involves using a properly structured permanent life insurance policy as a long-term financial tool.
Madhavi explained that these policies can provide a death benefit while also accumulating cash value that the policyholder may be able to access through policy loans. That capital can potentially be used for other purposes, such as investing in real estate or funding a business.
She emphasized that she views the strategy as a conservative financial foundation rather than a traditional investment account.
Dustin shared how he has used his own Penn Mutual policies, including borrowing against them to help fund earnest money for real estate transactions and repaying the loans as the deals progressed.
The conversation also highlighted the importance of understanding the mechanics before using a strategy like this. Borrowing costs, policy structure, interest, performance assumptions, and other factors can vary significantly, so investors need to evaluate whether the approach fits their individual financial situation and goals.
The Power of Collaborative Due Diligence
Madhavi also discussed Connected Capital Community, a group she created to make the investment evaluation process more collaborative.
The community brings together fund managers and capital allocators who evaluate operators and investment opportunities as a group. Members review opportunities across several asset classes, including multifamily, self-storage, mobile home parks, industrial real estate, and business acquisitions.
Operators present opportunities to the group, members ask questions, and the fund managers then discuss the opportunity privately.
The goal is to bring multiple perspectives to the due diligence process. Rather than relying on a single investor’s experience or assumptions, members can draw on the knowledge and expertise of people with different backgrounds.
Dustin noted that he appreciates this approach because different people often identify different risks, questions, or opportunities. A team-based process can uncover issues that one person might overlook.
Investor Communication Matters—Especially in a Challenging Market
The conversation also turned to the current multifamily environment and the importance of communication when market conditions become more difficult.
Dustin explained that his team maintains regular communication with fund managers and has built a dashboard that allows investors to review property-level information such as occupancy, income, and site notes.
For Madhavi, that kind of transparency becomes especially important when investments face challenges. Investors may be more understanding of difficult circumstances when they are kept informed and can clearly see how the operator is responding.
Both Madhavi and Dustin acknowledged that today’s multifamily market presents real challenges, but they also see potential opportunities.
Higher interest rates and changing lending conditions have created pressure for some owners and lenders, potentially opening the door for buyers who have the capital, patience, and discipline to act when fundamentally sound properties become available at more attractive valuations.
At the same time, raising capital has become more difficult than it was during the market’s boom years, and lenders and owners do not all respond to distress in the same way.
The takeaway is not to chase opportunities simply because the market has changed. Instead, both emphasized the importance of remaining patient, understanding the risks, and moving forward when the underlying numbers make sense.
Building Wealth With Strategy and Discipline
At its core, the conversation connected two areas that are often discussed separately: personal financial planning and real estate investing.
Madhavi’s approach is centered on building a strong financial foundation, understanding the strategies being used, and surrounding yourself with people who can provide experience and perspective.
For multifamily investors, the same principles apply.
Thorough due diligence, clear communication, strong relationships, and patience can become even more important when market conditions are uncertain.
The current environment may create opportunities, but it also requires investors to be more selective. For both Madhavi and Dustin, the goal isn’t simply to find a deal—it is to understand the deal, manage the risks, and make disciplined decisions for the long term.
To learn more about Madhavi’s approach to wealth strategy and financial education, visit ThinkOutsideTheStocks.com. Madhavi also offers educational resources and calculators designed to help people better understand different approaches to building wealth.