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The Wealth Independence Podcast guides high-income tech professionals through proven strategies for building passive income and achieving true financial independence.
Hosts Dustin Bailey and Adam Penn share battle-tested frameworks, real-world case studies, and hard-won lessons from their years of experience in private markets and alternative investments. Each week, they break down complex investment concepts, analyze current market trends, and interview successful investors and industry experts.
Through a freedom-first approach that emphasizes passive income, smart diversification, and thorough due diligence, learn how to shorten your learning curve and avoid common pitfalls on their path to financial independence.
Whether you're looking to understand private placements, real estate fundamentals, or alternative investment opportunities, Wealth Independence delivers actionable insights that help busy professionals make informed investment decisions.
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Interested in being a guest on the show? Reach out to us at guests@wealthindependencepod.com with a brief intro and any relevant topics you'd like to discuss.
70 Episodes
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How much of your portfolio should be liquid...and does a private credit fund or a line of credit “count” as liquidity? Adam recently got a one-on-one portfolio review from Bob Fraser (co-founder of Aspen Funds, author of Invest like a Billionaire, and Wealth Independence Podcast guest on episode v1.25). Bob’s verdict was blunt: Adam is too concentrated in real estate, too light on liquidity. Bob’s rule of thumb? 10–20% of net worth in something loosely liquid – brokerage accounts, private cre...
Matt Paulson started making money on the internet in the 1990s. Today he runs MarketBeat, a financial media company generating $50 million in annual revenue with 6 million email subscribers — all bootstrapped from a $5,000 college grant. He also co-owns 2,100 apartment units and 35 commercial properties through Creston Capital in Sioux Falls, SD...and if that wasn't enough, he also runs a $40 million venture capital fund investing in Midwest tech startups. Dustin and Adam sit down with Matt t...
Can you imagine borrowing millions for a real estate property, but not having to personally guarantee the loan? That’s the reality of non-recourse debt – and it’s one of the biggest differences between residential and commercial real estate lending. Dustin and Adam break down how non-recourse loans work, why lenders care more about an asset’s income than the borrower’s personal ability to repay, and what Freddie Mac considers a “small balance” loan (hint: the minimum is $1 million). For passi...
If you think a 14% return in the S&P 500 and a 14% cash-on-cash return in real estate are the same thing, you’re missing the full picture. Dustin and Adam dig into Robert Kiyosaki's recent tweet about selling $2.25 million in Bitcoin and reinvesting it into real assets generating $27,500 per month in tax-advantaged cash flow – and why the top reply (”just buy an S&P 500 ETF”) gets it completely wrong. One return is paper gains you can’t spend. The other is real money hitting your bank...
Dustin and Adam break down why two Wall Street Journal articles published on the same day – one about “little known” tax strategies and another about the “invitation only” world of private investing – both miss the bigger picture. The WSJ tax article covers SALT deduction changes, Roth conversions, inherited IRA withdrawals, and 529 plans – all standard Wall Street product advice. But the tax code is far bigger than the Wall Street product bubble. Real estate, oil and gas, and other private i...
Short-term rentals have become one of the more popular tax strategies for W-2 employees looking to reduce their taxable income – but is the so-called STR “loophole” really worth the hype? Dustin and Adam break down how the strategy works: buying a property, running it as a Schedule C business, hitting the 100-hour material participation threshold, and using cost segregation plus bonus depreciation to generate massive year-one tax deductions. Adam walks through a concrete example – a $500,000 ...
When you die, should your investment portfolio be sold off and split among your heirs…or structured to keep producing for generations? It’s a question most investors put off or avoid entirely, but the answer leads to two very different estate plans. Dustin and Adam explore the philosophical divide between liquidating everything at death versus building a self-sustaining portfolio designed to outlive you. The conversation was sparked by a real exchange Adam had with a fellow investor whose est...
What happens when you drill an oil well and oil starts gushing before you’re ready to catch it? Dustin and Adam walk through their latest oil and gas fund – an 11-well vertical portfolio in Oklahoma that closed for investment at the end of 2025. For most investors, the draw was the tax benefit: intangible drilling costs created an estimated 90%+ deduction – and as year-end approached, demand surged from investors racing to shelter income before December 31. What started as a six-well fund gre...
Dustin and Adam sit down with Ian Colville, founder and managing partner of Carpathian Capital Management, who oversees roughly $150 million in residential real estate assets. Ian's path to US real estate started in an unlikely place – running equity sales for Deutsche Bank and Citigroup in Moscow during the early 2000s BRIC boom – and the risk perspective he built there shapes everything about how he evaluates deals today. The conversation digs into the structural housing shortage that Ian b...
The Wall Street Journal recently declared commercial real estate “too cheap to ignore.” Dustin and Adam break down the article’s claims, challenge some cherry-picked data, and explain what institutional investors returning as net buyers for the first time since 2022 actually signals. Commercial real estate values are down from 2022 peaks on average…but how much of that decline reflects a real structural problem versus a correction from a bubble fueled by cheap debt? The discussion also digs i...
How do real estate development deals actually work for passive investors? And what makes them riskier than buying existing properties? Dustin and Adam sit down with Eugene Gershman, a second-generation developer with 20+ years of experience who now partners with landowners across the country to bring projects from raw land to stabilized assets. Eugene explains the two-tier capital structure many developers use: early-stage “GP funds” (comparable to startup seed capital) where investors take m...
Depreciation is one of real estate’s most powerful tax advantages – and maybe its most misunderstood. Dustin and Adam break down what passive investors actually need to know about real estate depreciation, including bonus depreciation, cost segregation studies, and the tax benefits that flow through to syndication investors. Bonus depreciation is back at 100%, and despite how aggressive it sounds, it’s actually the proper accounting method. But depreciation losses come with limitations that c...
What happens after you sell a 14-store business with 90 employees? Ian Noble joins Adam and Dustin to share his journey from dry cleaning entrepreneur to passive real estate investor, revealing the emotional identity shift after exiting a business, and explaining how his business background shaped his approach to evaluating passive investment opportunities. Dustin and Adam explore Ian's dual investment strategy: combining steady cash flow from private lending with equity upside through mobile...
Dustin and Adam tackle a fundamental question for business owners and high-earning professionals: when does it make sense to convert active income into passive investments rather than reinvesting in your business or career? They explore why syndications often provide better risk-adjusted returns than building your own real estate portfolio, particularly for investors who lack the time or desire to manage properties directly. The discussion covers the four ways real estate generates returns (a...
Dustin and Adam reflect on completing their first full year of the Wealth Independence Podcast (version 1) and share what’s ahead for version 2. The conversation covers which content resonated most with listeners, including strong feedback on the “No Investor Left Behind” series, particularly the cap rates episode. They discuss plans to expand educational content with topics like waterfall structures, bring on more established names from their network, and feature interviews with actual passi...
Dustin and Adam break down a recent Wall Street Journal article examining the push to bring private assets into 401(k) plans, and why this approach misses the point for passive investors seeking true alternatives. The discussion reveals a troubling reality: nearly 40% of Americans have never heard of private credit funds, and mainstream financial education continues to overlook the alternative investment space entirely. The episode explores the fundamental difference between real private inve...
Dustin and Adam explore the often-overlooked world of asset protection for real estate investors and high-income professionals. They break down the key difference between control and ownership, explaining how properly structured trusts and LLCs can create legal barriers that protect your assets without sacrificing your ability to manage them day-to-day. The conversation covers why living in America (where anyone can sue anyone for anything) makes asset protection especially relevant, addressi...
In this “No Investor Left Behind” episode, Dustin and Adam demystify RUBS (Ratio Utility Billing System) and explain how this common multifamily value-add strategy can significantly increase a property's net operating income and valuation. Using a practical example, they demonstrate how implementing a $40 per unit monthly utility billback across 20 units can add approximately $160,000 in property value when calculated at a 6% cap rate. The discussion covers different RUBS approaches, from occ...
Dustin and Adam tackle a question many passive investors face right now: is the market too high to invest? With concerns about AI investment bubbles, potential recessions, and stock market volatility dominating headlines, it’s easy to fall into analysis paralysis. In this episode, they make the case for why focusing on cash-flowing real estate investments provides a fundamentally different risk profile than timing the equity markets. The conversation explores why some wealthy investors contin...
In this Thanksgiving special, Dustin and Adam step back from deal analysis to reflect on gratitude, freedom, and the mistakes that shaped their investing journey. They discuss critical lessons learned the hard way, including the challenges of investing out of state too early and why property size can matter more than cap rates when factoring in real costs like travel and management. Adam shares insights from investing in smaller out-of-state properties versus larger multifamily assets, explai...
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