Can you build meaningful income through real estate without becoming a landlord or adding another job to your already busy schedule? Chad Ackerman is a former corporate HR and compensation executive with more than 25 years of experience who realized his financial future was far too dependent on his W2 income. That realization sent him down the path of passive real estate investing, where he made early mistakes, learned valuable lessons, and eventually co-founded Left Field Investors, one of the largest communities for passive investors, later acquired by BiggerPockets. 

Today, through CARE (Chad Ackerman Real Estate), Chad helps busy professionals move from confusion and overwhelm to clarity and confident action as passive real estate investors. He shares what he wishes he knew when he started, how to evaluate passive investment opportunities, avoid common mistakes, and create income streams without dealing with tenants, toilets, or day-to-day property management. If you're a hig...

What does it take to overcome incredible adversity and build lasting wealth through real estate? Kevin "KAYR" Robinson went from growing up in deep poverty in West Philadelphia—moving more than 18 times before adulthood—to building a multi-million-dollar real estate portfolio with more than 160 rental units. After attending Bowdoin College and working in investment banking at Goldman Sachs, KAYR combined disciplined systems, conservative investing principles, and relentless execution to create long-term financial independence.

Kevin also shares the inspiring story behind his two-time USA TODAY best-selling memoir, Can't Break Me, and how resilience became the foundation of his success. KAYR dives into the strategies that are helping investors succeed in today's higher interest rate environment, including how to stress-test deals, avoid thin-margin mistakes, use conservative leverage, and build a portfolio designed for long-term stability. This episode is packed with actionable re...

What if everything you've been told about building wealth is only part of the story? Dr. Dipesh Sitaram was a practicing dental surgeon who discovered that even a high-income career wasn't enough to create true financial freedom. Instead of relying solely on traditional investments like stocks and retirement accounts, he began building a multi-million-dollar portfolio through private real estate and alternative investments—the same types of opportunities that many wealthy investors have used for decades. 

As the founder of Responsible Real Estate and Acuere Capital Partners, Dipesh helps physicians and everyday investors understand how to evaluate private deals, generate passive income, protect their assets, and build long-term wealth with confidence. We explore why diversification matters, how private investments differ from the public markets, the mindset required to think like an investor instead of an employee, and practical strategies for creating financial freedom that exte...

What if you stopped waiting until retirement to start living? Chris Larsen, founder of Next-Level Income, made it his mission to achieve financial freedom after losing his father at a young age and his best friend at just 18. While building a successful career in medical device sales, Chris quietly built a real estate portfolio, starting with his first rental property at age 21 with less than $3,000 down. Over time, his passive income grew to the point where his paycheck became optional.

Today, Chris helps investors build wealth through commercial real estate investments across multifamily, self-storage, car washes, and senior housing, with more than $2 billion in acquisitions since 2016. In this episode, he shares the principles behind his new book, How to Be Financially Free by Forty, and the strategies he used to create financial freedom, lasting wealth, and a life lived on his own terms. 

In this episode, you will be able to:

• Discover how to build lasting wealth throug...

What would it take for you to walk away from a guaranteed pension… and bet on yourself instead? Former United States Navy Chief Petty Officer Tim Kelly made one of the boldest decisions of his life: leaving the military four years before retirement eligibility to pursue true financial freedom through real estate, mindset, and high-performance living.

After spending 15 years leading under pressure in the Navy, he realized he wanted more than just security—he wanted freedom of time, freedom of choice, and the ability to build a life fully on his own terms. That journey led him deep into real estate investing, personal growth, and wealth-building strategies that ultimately helped him become involved in nearly 2,000 commercial real estate units.

Today, he serves on the Board of Directors for Active Duty Passive Income, is a certified High Performance Coach, and co-authored the bestselling book “Military House Hacking,” helping service members, veterans, and entrepreneurs create fina...

Mathew Owens is a CPA, real estate investor, and founder of OCG Capital. He shares with us the strategies behind building a real estate empire that spans more than 1,500 units, over 1,000 home flips, and more than $500 million in loans to investors. Matt has also raised over $200 million in private capital, giving him a unique perspective on what separates successful investors from those who struggle to scale.

We dive into his disciplined approach to investing, including the 200-point due diligence checklist he uses to evaluate opportunities and minimize risk before committing capital. Matt shares lessons learned from decades of experience as both an active operator and passive investor, offering practical insights on finding quality deals, raising private money, building passive income, and creating long-term wealth through real estate. This episode is packed with actionable advice from someone who has successfully navigated nearly every corner of the real estate investing world...

What happens when a firefighter working 24-hour shifts decides to build a future through real estate? Thomas St. John, founder of North Corp Capital, who also worked part of his career as a mailman, shares hear how he went from serving his community to building a successful multifamily investment company with over 20 years of experience in the trenches of real estate. 

Starting with his first duplex back in 2006, Thomas steadily scaled his portfolio and eventually created a vertically integrated operation complete with in-house property management. Today, through North Corp Capital, Thomas specializes in multifamily investing, asset syndication, and helping investors grow wealth through strategic, risk-conscious real estate opportunities. 

We dive into the lessons he’s learned about leverage, scaling responsibly, managing risk, and building strong investor relationships over the long haul. If you’re interested in multifamily investing, creating financial freedom outside of a tra...

We take you behind the scenes of our latest multifamily apartment acquisition—a 128-unit building we closed on for $6.6M—and break down every step of the deal: how we found and financed the property, the due diligence, the negotiation process, the renovation strategy, and the property's future. We share the numbers, projected challenges, and value-add opportunities that made this investment worth pursuing, while offering practical insights for both new and experienced investors. If you’ve ever wanted a firsthand look at how successful multifamily deals come together, this episode delivers a transparent, real-world blueprint for building wealth through apartment investing. 

In this episode, you will be able to understand:

• How real estate investing creates wealth through multiple streams — cash flow, appreciation, loan paydown, and tax benefits all work together over time.
• Bigger deals create bigger economies of scale. Multifamily investing allows investors to access oppor...

What if you could build a $60M real estate portfolio without syndications, big money, or insider connections? James Gleeson shares how he went from buying his first rental at 21 to owning 400+ units—using simple, repeatable strategies like BRRRR and value-add investing in his own backyard of St. Louis. 

He breaks down the real lessons, mistakes, and mindset shifts that helped him scale. Now mentoring dozens of investors who’ve collectively closed $50M+ in deals, James proves that building real wealth through real estate is simpler—and more attainable—than most people think.

In this episode, you will be able to:

• Understand why real estate growth is compounding and how scaling becomes easier over time
• Learn how James Gleeson built a $60M portfolio and 400+ units starting from scratch
• Discover how to get started in real estate with limited resources by leveraging relationships and persistence
• Identify the importance of building strong relationships to unlock deals, funding, ...

What does it really take to build an 8-figure business… and survive the crashes along the way? Tom Dunkel is a battle-tested entrepreneur who’s spent nearly 30 years in the trenches of business. He’s built two 8-figure companies, lost six, and raised over $50 million across multiple asset classes. Tom doesn’t just talk about success—he’s lived the full spectrum of wins, setbacks, and hard-earned comebacks. 

Now serving as Managing Director of Eagle Capital, Tom helps investors grow their wealth through operator-backed deals, but his true passion is still building businesses from the ground up. From assembling elite teams to turning chaos into clarity, he brings real-world strategy you won’t find in a textbook. 

We dive into the lessons failure teaches, what separates good operators from great ones, and how to keep pushing forward when things don’t go as planned. Plus, you’ll hear how Tom balances high-stakes business with life outside the office—as a competitive golfer, rock b...