Wealth Independence Podcast

Dustin Bailey & Adam Penn
  • 5.0 (5)
  • Investing
  • Updated Weekly

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. Submit feedback or questions (copy & paste into your address bar): https://www.wealthindependencepod.com/contact 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.

  1. 5d ago

    v2.32 - When Banks Say No, Private Lenders Say Yes (ft. Ryan Hermansky)

    Put 50% down on a house and every bank in America will trip over itself to write the loan. But put 50% down on a $3 million shopping center? Most banks won’t return your call. That gap is Ryan Hermansky’s whole business. As president and co-founder of Private Money Funding, he lends where banks won’t – to tired shopping centers being turned around, land deals, owners who need to close in two weeks instead of six months, among others. Ryan walks Dustin and Adam through both sides of the ledger: borrowers with millions of their own equity on the line (part of the reason his fund has never seen a late payment or a foreclosure) and investors funding the loans, some living entirely off the cash flow they earn. The debt side of real estate is often considered boring. But boring usually means consistent…and as an investor, that’s exactly the point. Episode Release Notes & Resources: Private Money Funding: https://privatemoneyfunding.comConnect with Ryan: 602-284-4888 / ryan@pmfaz.com / https://www.linkedin.com/in/ryan-hermansky-a235248[Big Spring Capital] Consistency-vs-volatility: https://www.bigspringcap.com/resources/dave-ramsey-12-percent-myth Watch episode on YouTube: https://www.youtube.com/watch?v=g1WLgZZnPDw See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.32 - When Banks Say No, Private Lenders Say Yes (ft. Ryan Hermansky)

  2. Aug 7

    v2.31 - No Investor Left Behind: 1031 Exchanges

    A 1031 exchange (named for its section of the tax code) lets you roll real estate investment gains into a new property, deferring the tax and keeping all of your capital working. Dustin and Adam rank it as the second-biggest tax benefit in real estate, right behind depreciation. But like almost anything involving the tax code, 1031 exchanges are full of gotchas and “it-depends.” In this No Investor Left Behind episode, they walk through the rules that make it work: the like-kind requirement, the 45-day and 180-day deadlines, and the “qualified intermediary” necessary to run it all. They also cover a common question from passive investors: can you 1031 from one syndication to another? Done over decades (“swap till you drop”), it’s one of the most powerful tools for keeping wealth. You just have to follow the rules. Episode Release Notes & Resources: Book: An Agorist Primer by Samuel Edward Konkin III: https://a.co/d/dX8w9RM Watch episode on YouTube: https://www.youtube.com/watch?v=JUnqV6JOnAk See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.31 - No Investor Left Behind: 1031 Exchanges

  3. Jul 31

    v2.30 - The 80/20 Double Standard

    Plenty of single-family investors have split a deal 50/50 with another partner and never thought twice about it. But put a passive syndication in front of them with an 80/20 LP/GP split, and the sponsor’s 20% suddenly becomes a dealbreaker. Dustin and Adam dig into that double standard: why some investors feel that a split that leaves you with 80% is somehow worse than one that leaves you half, and what a sponsor actually does for their share – sourcing the deal, qualifying for the debt, and managing every investor relationship in it (among dozens of other things). Then they get to where the scrutiny actually belongs in a syndication: fees. How acquisition fees should scale with deal size, what those fees actually pay for, and the alignment signal when a sponsor leaves their fees in the deal as equity. The profit split is the headline number – but the fees are where the gotchas live. Episode Release Notes & Resources: Episode v2.27 – No Investor Left Behind: Investor Splits, Waterfalls, and Preferred Returns – https://www.wealthindependencepod.com/2432117/episodes/19459737 Watch episode on YouTube: https://www.youtube.com/watch?v=PV-4HwqjBt4 See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.30 - The 80/20 Double Standard

  4. Jul 24

    v2.29 - 1,000 Investors, One Recurring Mistake (ft. Mike Sullivant)

    Every deal that shows up in your inbox leads with the same summary: a projected return, a hold period, a market, an asset class. Comparing those side by side feels like diligence. But two deals projecting the same return can end in completely different places...and the reason isn’t on the summary pages. Mike Sullivant has seen where the deals actually end. As Director of Fund Partnerships at Aspen Funds, he’s spent the last four years in conversation with the firm’s roughly 1,000 limited partners – hearing both the wins and the horror stories of investing in private alternatives. Mike joins Dustin and Adam to share what those thousands of conversations taught him, starting with why the gap between two identical-looking deals almost always comes down to the operator – the thing newer investors often treat as an afterthought. From there, they get into the rest of what a summary page won’t tell you: how aggressive the assumptions are, where a deal sits on the “risk pyramid,” and what to ask the fund-of-funds manager standing between you and the asset. Episode Release Notes & Resources: Aspen Funds: https://aspenfunds.usInvest Like a Billionaire community: https://investlikeabillionaire.org Watch episode on YouTube: https://www.youtube.com/watch?v=NCHdQvUaTvc See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.29 - 1,000 Investors, One Recurring Mistake (ft. Mike Sullivant)

  5. Jul 17

    v2.28 - Wall Street’s Hottest Trade Is Losing Money (On Purpose)

    The Wall Street Journal is calling a new kind of tax-loss harvesting the hottest trade on Wall Street – funds built to deliver index-like returns with a smaller tax bill. Dustin and Adam read the coverage and land on a simpler summary: tax-loss harvesting only works when you lose money. They walk through the mechanics – sell the losers, realize the losses, offset the gains on your winners – and why fund managers are now assembling portfolios designed to produce losses on purpose, since a rising market makes losers hard to find. Stock market tax-loss harvesting contrasts sharply with real estate and oil and gas. Depreciation is a paper loss: a deduction with no money actually leaving your account. It’s how investors can collect cash flow yet still take a sizable tax deduction. If the stock market is your entire investing universe, tax-loss harvesting is a fair tool. But step outside it, and there are tax strategies that don’t require losing money first. Episode Release Notes & Resources: [WSJ]: Stock Gains Without All the Taxes? How the Hottest Trade on Wall Street Works - https://www.wsj.com/finance/investing/stock-gains-without-all-the-taxes-how-the-hottest-trade-on-wall-street-works-ed321611 Watch episode on YouTube: https://www.youtube.com/watch?v=2B14TcsTfdY See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.28 - Wall Street’s Hottest Trade Is Losing Money (On Purpose)

  6. Jul 10

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

    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 nothing about whether an operator can actually operate. That doesn’t mean you can ignore it. The structure is how you and the operator split what a deal earns – and it sets the order everyone gets paid in. In this No Investor Left Behind episode, Dustin and Adam walk through how these structures work – straight profit splits like (80/20 or 70/30), tiered waterfalls that shift the split once a deal hits a target return, and preferred returns, where investors collect the first cash flow before any split. Episode Release Notes & Resources: WIP episode v1.45 – The Complexity Trap in Real Estate Syndications: https://www.wealthindependencepod.com/2432117/episodes/18068846Passive Perspectives PP050 – Preferred Returns: Risks, Benefits, and Common Misconceptions: https://bigspringcap.com/passiveperspectives/preferred-returns-real-estate-syndicationPassive Perspectives newsletter – passiveperspectives.com Watch episode on YouTube: https://www.youtube.com/watch?v=A8vIEPgDA4I See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

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

  7. Jul 3

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

    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 decade and 20-plus acquisitions later, he joins Dustin and Adam to walk through how private equity in the lower-middle-market space actually works: buying founder-led companies from owners who need a succession plan, layering bank debt, seller notes, and equity, then paying that debt down with the company’s own cash flow. The tried-and-true leveraged buyout (LBO) model. They get into where this sits on the investment risk scale, why he’ll walk from a deal everyone else loves, and how accredited investors can now reach a space that used to require a Goldman Sachs-sized check. Episode Release Notes & Resources: Pass the Hat: https://www.passthehat.comBorgman Capital: https://www.borgmancapital.com/Connect with Sequoya on LinkedIn: https://www.linkedin.com/in/sequoya-borgman-8a6057a Watch episode on YouTube: https://www.youtube.com/watch?v=D1aSMxSRdMM See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

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

  8. Jun 26

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

    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 property. He joins Dustin and Adam to break down his process: buying a delinquent mortgage from a bank at a discount, why picking up a note at half its face value can double your effective yield, and why he aims to “rehab the borrower” not the property. They cover a note’s exit strategies (reselling a reperforming loan, foreclosure, cash-for-keys), Scott’s rule never to buy a note on a property he wouldn’t want to own outright, the surprising tax benefits, and using a self-directed IRA to buy notes. Episode Release Notes & Resources: We Close Notes: https://weclosenotes.comScott’s free note investing training - Note Weekend: https://noteweekend.com Watch episode on YouTube: https://www.youtube.com/watch?v=E6DGhk2WJNQ See all Wealth Independence episodes at https://www.wealthindependencepod.com Connect with Dustin: Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam: Bidwell CapitalLinkedIn (/in/AdamJPenn) This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

    v2.25 - Be the Bank, Not the Landlord (ft. Scott Carson)
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Ratings & Reviews

5
out of 5
5 Ratings

About

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. Submit feedback or questions (copy & paste into your address bar): https://www.wealthindependencepod.com/contact 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.

Information

  • Creator
    Dustin Bailey & Adam Penn
  • Years Active
    2024 - 2026
  • Episodes
    88
  • Rating
    Clean
  • Copyright
    © 2026 Wealth Independence Podcast
  • Show Website
    Wealth Independence Podcast

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