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Wealth Independence Podcast
Dustin Bailey & Adam Penn
47 episodes
3 days ago
Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market. After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result. The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, ...
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Investing
Business
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All content for Wealth Independence Podcast is the property of Dustin Bailey & Adam Penn and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market. After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result. The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, ...
Show more...
Investing
Business
Episodes (20/47)
Wealth Independence Podcast
v1.43 - Don’t Let Bad Deals Kill Your Investment Strategy
Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market. After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result. The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, ...
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3 days ago
25 minutes

Wealth Independence Podcast
v1.42 - When “Passive” Real Estate Isn't Actually Passive
Dustin and Adam dive into the harsh reality of “passive” real estate investing, exposing why the common advice to “just hire a property manager” for single-family rentals often creates more problems than it solves. The discussion covers why good property managers are expensive and hard to find, especially for smaller properties, and how the best property management companies don’t even manage properties for other investors. They explore how syndications and private placements offer truly pass...
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1 week ago
16 minutes

Wealth Independence Podcast
v1.41 - Tax Planning for Passive Investors
Dustin and Adam dive deep into proactive tax planning strategies specifically designed for passive investors. They explain why waiting until March to think about the previous year’s taxes is too late and share their systematic approach to tax optimization throughout the year. The discussion includes the short-term rental “loophole” strategy for W-2 earners, qualifying for real estate professional status, and the critical importance of working with qualified tax professionals who understand al...
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2 weeks ago
24 minutes

Wealth Independence Podcast
v1.40 - The Liquidity Misconception
Dustin and Adam challenge the common assumption that stock market liquidity provides a meaningful advantage over real estate investments. They explore why many investors view the illiquidity of real estate as a downside and argue that this perspective may actually hinder long-term wealth building. They examine the trade-offs between liquidity and volatility, explaining how frequent price fluctuations can damage compounding returns over time. They share practical insights on why cash-flowing a...
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3 weeks ago
18 minutes

Wealth Independence Podcast
v1.39 - Behind the Scenes of a 20-Unit Acquisition
Dustin and Adam go behind the scenes of a recent 20-unit multifamily acquisition, pulling back the curtain on what passive investors typically don’t see: the last-minute surprises, changing terms, capital raising challenges, and sponsor decision-making that happens right up until closing day. The discussion covers the realities of working with local banks versus larger lenders, how unexpected insurance requirements can materially impact deal returns, and the importance of conservative expense...
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1 month ago
24 minutes

Wealth Independence Podcast
v1.38 - Out-of-State Real Estate Reality Check
Thinking about buying rental properties out of state? Dustin and Adam share hard-earned lessons from managing 25+ units in Memphis while living hundreds of miles away. This episode reveals why out-of-state real estate investing is rarely as passive as it seems, covering the real challenges of building reliable contractor teams in different markets, dealing with quality control from a distance, and the hidden costs that can wipe out years of cash flow. The discussion includes practical realiti...
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1 month ago
16 minutes

Wealth Independence Podcast
v1.37 - When Deals Don’t Perform
Adam and Dustin tackle a topic most investors prefer to avoid: what happens when your real estate investments underperform or lose money entirely. The conversation includes candid insights about different levels of deal performance, from cash flow shortfalls to complete capital losses, along with why position sizing is the most critical risk management tool for passive investors. The discussion also explores the safety nets that can protect your investments during challenging times, including...
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1 month ago
20 minutes

Wealth Independence Podcast
v1.36 - Finding Deals When Others Retreat
Fresh from the Limitless Financial Freedom Expo, Dustin and Adam deliver boots-on-the-ground insights from networking with dozens of active and passive investors. Rather than sitting in sessions, they spent their time in conversations with deal makers, capital raisers, and fellow investors to get a real pulse on today’s market conditions. Their key takeaway? While conference attendance was down 25% and fewer vendors were present, serious money is still moving and some of the best investment o...
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1 month ago
18 minutes

Wealth Independence Podcast
v1.35 - Amazon-Proof Real Estate Investing (ft. Steve Salvigsen)
Dustin and Adam interview Steve Salvigsen of Sage Square Capital, a seasoned commercial real estate investor who specializes in strip mall and medical/retail properties. Steve shares his transition from residential development to building a successful portfolio of cash-flowing commercial assets, and dives deep into his unique investment thesis targeting secondary port cities like Savannah, Mobile, and Charleston, where major infrastructure investments are driving population and business growt...
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1 month ago
39 minutes

Wealth Independence Podcast
v1.34 - Building Your Retirement Cash Flow Portfolio
Adam and Dustin challenge the conventional retirement wisdom of shifting from stocks to bonds just when you need income most. Adam shares his personal journey from W-2 employee to building a cash-flowing real estate portfolio that generates consistent monthly income, explaining how he constructed a diversified investment strategy using rental properties, oil and gas investments, and strategic tax planning. The discussion includes why successful investors stay actively involved in their wealth...
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2 months ago
18 minutes

Wealth Independence Podcast
v1.33 - Building Passive Income Through Private Credit (ft. Jared Benson)
Dustin and Adam interview Jared Benson of Clotine Capital, a successful real estate broker who partnered to launch a debt fund while maintaining his real estate practice. Jared shares his journey from struggling with house flipping side projects to discovering the power of passive investing and eventually partnering with experienced operators to create an income-focused debt fund. Key topics include the critical differences between debt funds in today’s market, red flags to watch for in prefe...
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2 months ago
35 minutes

Wealth Independence Podcast
v1.32 - Decoding GP Fees in Real Estate Syndications
Adam and Dustin tackle one of the most misunderstood aspects of private real estate investing: general partner (GP) compensation. If you’ve ever wondered why deal sponsors take 20% of profits or bristled at acquisition fees, this episode dives deep into the economics behind GP fee structures and why they’re actually designed to benefit passive investors (if done correctly). The conversation ranges from real-world examples of fee arrangements, complex waterfall structures that incentivize outp...
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2 months ago
20 minutes

Wealth Independence Podcast
v1.31 - Should You Do All the Work Yourself?
When you first discover passive real estate investing, a natural question emerges: “Why not just do all the work myself and make more money?” Dustin and Adam tackle this common dilemma facing passive investors. Drawing from Adam’s hands-on experience managing Airbnb properties – including 2AM guest calls and emergency repairs – they explore the true costs of active investing beyond just the financial returns. Discussion includes the critical trade-offs between higher cash returns and time fre...
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2 months ago
17 minutes

Wealth Independence Podcast
v1.30 - The Case Against Starting Small in Real Estate
Dustin and Adam challenge the conventional wisdom that real estate investors should “start small.” Drawing from their recent experience with a large Las Vegas deal, they explain why larger real estate investments often provide better execution, stronger teams, and more motivated service providers. They explore how bigger deals attract more qualified professionals (from lenders and insurance brokers to property managers) who are willing to dedicate more time and resources when the potential re...
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3 months ago
20 minutes

Wealth Independence Podcast
v1.29 - You Make Your Money When You Buy
Dustin and Adam dive into one of the most fundamental principles of successful investing: “you make your money when you buy.” Using real examples from recent apartment building acquisitions and fix-and-flip projects, they discuss why the purchase price is often the biggest lever in determining investment success. They break down how overpaying upfront makes it nearly impossible to “earn your way out” of a deal (even with significant value-add improvements), and share insights on evaluating ac...
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3 months ago
16 minutes

Wealth Independence Podcast
v1.28 - From Behind the Iron Curtain to Real Estate Freedom (ft. Vessi Kapoulian)
Dustin and Adam chat with Vessi Kapoulian, an experienced real estate investor with a unique background in commercial lending. Vessi shares her journey from growing up behind the Iron Curtain in Bulgaria to corporate America, where witnessing multiple restructures and income limitations sparked her transition to real estate investing. Drawing on her CRE lending experience reviewing hundreds of deals and investor financial statements, Vessi reveals what successful real estate investors do diff...
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3 months ago
38 minutes

Wealth Independence Podcast
v1.27 - Beyond Cash Flow: Determining Return on Equity
Dustin and Adam explore a critical concept that many real estate investors overlook: analyzing an asset’s return on equity. While most investors focus solely on monthly cash flow, evaluating whether your equity is working as hard as it should be is an important part of portfolio management. Using practical examples, Adam and Dustin break down the difference between cash-on-cash returns and return on equity, showing how appreciation creates opportunities for strategic portfolio rebalanci...
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3 months ago
18 minutes

Wealth Independence Podcast
v1.26 - Red, White, and Cash Flow
In this Independence Day special episode, Dustin and Adam break down a three-step framework for making your own personal declaration of financial independence. They explore how to break free from single income sources and stock market-only portfolios by building multiple cash-flowing income streams through real estate syndications and private placements. Discussion includes the power of fractional ownership (via syndications) versus buying individual properties, emphasizing how passive invest...
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4 months ago
17 minutes

Wealth Independence Podcast
v1.25 - The Billionaire Investment Playbook (ft. Bob Fraser)
Dustin and Adam sit down with Bob Fraser, co-founder and CFO of Aspen Funds. Bob, a Berkeley computer science graduate and former programmer turned successful entrepreneur, shares his journey from losing everything in the dot-com crash to building a private equity firm focused on macro-driven investing strategies. The wide-ranging discussion includes the power of uncorrelated assets like real estate, oil and gas, and private credit in building truly diversified portfolios. Bob emphasizes the ...
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4 months ago
38 minutes

Wealth Independence Podcast
v1.24 - Unregistered Securities and Other Investor Myths
Dustin and Adam tackle the common concerns and misconceptions that often keep high-income professionals from exploring private real estate investments. If you've ever wondered why your financial advisor steers you away from private placements or why these “unregistered securities” sound so risky, this episode breaks down the reality behind the (mostly unfounded) fears. The hosts explain why most CFPs aren't trained in alternative investments, explore the structural reasons behind advisor hesi...
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4 months ago
24 minutes

Wealth Independence Podcast
Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market. After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result. The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, ...