Dustin Bailey & Adam Penn

Wealth Independence Podcast

Business EN ↓ 83 episodes

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 thor...

Author

Dustin Bailey & Adam Penn

Category

Business

Latest episode

Jul 10, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

v2.27 - No Investor Left Behind: Investor Splits, Waterfalls, and Preferred Returns 10.07.2026

The first time you put money into a commercial real estate syndication, the way the profits get divided up can look surprisingly complicated – tiered splits, preferred returns, and something sponsors call a “waterfall.” It’s easy to read this complexity as a sign the sponsor knows what they’re doing. But Dustin and Adam make the opposite case: most of it is marketing, and it tells you almost nothi...

v2.26 - Investing in Private Equity for Individual Investors (ft. Sequoya Borgman) 03.07.2026

For most individual investors, “private equity” is usually associated with “inaccessible” – something reserved for the Elon Musks and Blackstones of the world. Buying and running established companies has been an institutional game with large minimums and no obvious way in. Sequoya Borgman spent nearly two decades in public accounting before leaving a partner’s seat to buy businesses himself. A de...

v2.25 - Be the Bank, Not the Landlord (ft. Scott Carson) 26.06.2026

Most real estate investing means owning the building – and taking on the tenants, toilets, and trash that come with it. But there’s another way to invest in real estate: owning the debt instead of the property, and collecting the payments as the lender. “The Note Guy” Scott Carson has spent nearly two decades doing exactly that, buying and selling mortgage debt on residential and commercial proper...

v2.24 - No Investor Left Behind: Commercial Real Estate Debt 19.06.2026

The loan on your house is simple: take out a 30-year mortgage, make your payments, own the house at the end. But commercial real estate debt is a different animal, with widely-varying structures that don’t exist in the residential world – and unique terms that directly affect the risk and returns of any deal that carries them. Dustin and Adam break down how it actually works with real-world exampl...

v2.23 - The Manufactured-Home Niche Hiding in Plain Sight (ft. Brent Bowers) 12.06.2026

Most real estate investors chase houses, apartments, or self storage. But Brent Bowers built his business on something almost nobody talks about: buying cheap vacant land and selling it at a profit…often with a brand-new manufactured home placed on it first. A former US Army officer, Brent walks Dustin and Adam through how it all works. He buys land well below market value, then resells it…becomin...

v2.22 - Pensions, Private Credit, and the Quiet CRE Reset 05.06.2026

What’s actually backing the money you’re counting on for later? Dustin and Adam take that question through two Wall Street Journal articles: one on what’s quietly accumulated inside pension funds, the other on a shift in how distressed commercial real estate loans are getting resolved. The first article traces how pension funds chasing yield in private markets ended up holding a hidden slice of th...

v2.21 - Rivers of Cash Flow (ft. Cameron Philgreen) 29.05.2026

Cameron Philgreen photographed ~400 weddings before he bought his first rental property. He’s now up to 25 rentals, a specialty coffee shop, and a 50,000 sq. ft. commercial building in Waco, Texas – all of it sparked by one dinky house he bought in 2017. He walks Dustin and Adam through the BRRRR method (Buy, Rehab, Rent, Refinance, Repeat), a house-hack so lean he shared a bathroom with his own A...

v2.20 - No Investor Left Behind: Real Estate Professional Status (REPS) 22.05.2026

Real Estate Professional Status (REPS) is a tax designation that lets qualifying investors deduct real estate losses (primarily from depreciation) against ordinary/active income like a W-2 salary. The benefit is real – but the bar is high, and the IRS pays attention to whether you clear it or not. Dustin and Adam walk through the REPS two-part test: 750+ hours/year of material participation, AND m...

v2.19 - Hard Money Loans & Character-Based Lending (ft. Will Harvey) 15.05.2026

When individual fix-and-flip investors need a loan to purchase and rehab a property, they usually don't get a bank loan – instead, they go to a private lender for a hard money loan: a short-duration note, secured by a first lien on the property. And while hard money loans are a solid tool for house flippers, they're also a powerful asset class for the investors who fund the notes. Hard m...

v2.18 - No Investor Left Behind: Debt Service Coverage Ratio (DSCR) 08.05.2026

Debt Service Coverage Ratio (DSCR) is a critical part of any debt-financed real estate deal, and shows up in nearly every real estate syndication pitch deck – but many passive investors would struggle to explain what it measures or why it matters. Dustin and Adam walk through the simple math behind this important metric (property income divided by annual debt service) and explain how it’s a measur...

v2.17 - Why Your Financial Advisor Won’t Cut Your Tax Bill (ft. Kevin Brunner) 01.05.2026

Most investors think about taxes once a year: when they file. Kevin Brunner, founder of The Q Companies, joins Dustin and Adam to talk through what proactive tax planning looks like and why most financial advisors aren’t set up to deliver it. Kevin breaks down why W-2 earners can benefit from a side LLC for real tax planning, the five-year real estate cost-segregation trap, and his installment sal...

v2.16 - Not All "Private Credit" Is the Same 24.04.2026

“Private credit” has become a headline label covering wildly different investments – loans to software companies, rescue capital for distressed borrowers, and real estate-backed lending all filed under the same term. Recent Wall Street Journal coverage treats the space as if it moves together. Dustin and Adam walk through why it doesn’t. Real estate private credit specifically is fundamentally dif...

v2.15 - How Everyday Trade Creates Fixed Income Returns (ft. Andreas Schweitzer) 17.04.2026

A $3 trillion financing gap exists between the companies that make everyday products and the buyers who purchase them. When a hammer manufacturer needs payment in 30 days but Home Depot pays in 120, someone has to bridge that gap – and it’s rarely a bank. Andreas Schweitzer, trade finance veteran who was running a half-billion-dollar book of business out of Panama at 26, joins Dustin and Adam to b...

v2.14 - Portfolio Review with a Billionaire's Playbook 10.04.2026

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...

v2.13 - Building a $50M Media Empire and Deploying It Into Real Estate (ft. Matt Paulson) 03.04.2026

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...

v2.12 - No Investor Left Behind: Recourse vs. Non-Recourse Debt 27.03.2026

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, a...

v2.11 - What Robert Kiyosaki’s Bitcoin Sale Actually Teaches 20.03.2026

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...

v2.10 - Why the “Invitation Only” Investment Club Is Wide Open 13.03.2026

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...

v2.9 - No Investor Left Behind: STR Tax “Loophole” 06.03.2026

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...

v2.8 - Legacy vs. Liquidation 27.02.2026

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 outli...

v2.7 - Oil Wells, Tax Breaks, and Year-End Scrambles 20.02.2026

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 surge...

v2.6 - Due Diligence, Deal Structures, and the Housing Shortage (ft. Ian Colville) 13.02.2026

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 abo...

v2.5 - The “Old Playbook” for Real Estate Is Dead 06.02.2026

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 stru...

v2.4 - Development Risk, Timing, and Deal-Breakers (ft. Eugene Gershman) 30.01.2026

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 d...

v2.3 - No Investor Left Behind: Real Estate Depreciation & Bonus Depreciation 23.01.2026

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,...

Listen to the Wealth Independence Podcast podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.