Episodios

  • 193. Is the AI Bubble about to Burst? Plus: Fed Questions, Crypto Collapse, and 50-Year Mortgages
    Nov 22 2025

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    On this episode, we're talking about AI, the Fed, crypto, and housing --- and how those stories all suddenly collided this week. Nvidia’s huge earnings beat briefly sent markets higher, but the rally fizzled fast as investors grew more anxious about a potential AI bubble. We walk through why valuations increasingly assume massive job displacement and unprecedented productivity gains, and why Oracle has become the market’s “AI downside” hedge as its stock price collapses and its credit spreads blow out.

    Zooming out to the macro picture: delayed economic data finally hit, with job growth surprising to the upside, suggesting the Fed might not be delivering a December cut after all. Combine that with softening AI sentiment, and we’re seeing a classic risk-off move: equities selling and cryptocurrencies like Bitcoin showing the most stress. Even though headline data looks fine, the real-world "vibes" (sorry, couldn't help ourselves) feel recessionary, with people struggling to find jobs while prices (especially housing prices) remain painfully high.

    That leads us into the debate over 50-year mortgages. We explain why extending mortgages just means paying interest for decades, barely building equity, and ultimately bidding home prices even higher. The idea of a transferable 50-year mortgage makes even LESS sense. It breaks basic collateral math and would require higher rates, not lower, to actually facilitate implementation.

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    39 m
  • 192. Distressed Debt 101 with the Private Credit GOAT Michael Gatto
    Nov 17 2025

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    We’re almost 200 episodes in, and we’ve been waiting for the perfect guest to come on to explain distressed debt investing... the wait is over. In this episode, we’re joined by Michael Gatto, who quite literally wrote the book on credit with The Credit Investor’s Handbook, and serves as the head of private side investing (private markets) at Silver Point, a $41 billion credit asset management firm. With private credit dominating headlines for all the wrong reasons - fraud, liquidations like Tri-Color, and restructurings like First Brands - we use this conversation to ask: what actually happens when private credit deals go sideways?

    Michael walks us through the world of distressed debt investing: what it is, how it differs from value equity and private equity, and why phrases like “liability management exercises” are just a sanitized way to describe creditor-on-creditor violence. We talk through the mechanics of LMEs, getting J-screwed, up-tiering, CLOs, covenant-lite loans, and how “too much money chasing too few deals” set the stage for today’s blow-ups. He also explains why the press loves calling distressed investors vultures, why he thinks they’re often actually the heroes of the story, and how distressed funds can end up owning companies outright through bankruptcy.

    We also zoom out to the bigger picture: where we are in the credit cycle, why private credit has grown so explosively since 2008, and why Michael thinks some funds are absolutely going to blow up—but the system won’t. He shares red flags from situations like First Brands and why the current ratio is a joke. Along the way, we get Michael’s incredible career story (including how he negotiated his way into Goldman via a temp agency), his philosophy on learning, mentorship, and networking, and practical advice for anyone curious about private credit, distressed debt, or building a career in credit investing.

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    2 h
  • 191. Carlyle's Head of Global Wealth, Shane Clifford on Why It's Time to Rethink Private Markets
    Nov 8 2025

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    We are thrilled to present a SPECIAL EDITION of The Wall Street Skinny. This episode, recorded live at Carlyle’s NYC offices, is a candid interview with one of our most impressive (yet shockingly down-to-earth) guests to-date: Shane Clifford, Carlyle’s Head of Global Wealth.

    If you’re wondering how “Global Wealth” fits into one of the world’s most prestigious private equity mega funds, you’re not alone. We set the record straight about what Global Wealth is, how it relates to the rest of the business, and how it is reshaping the investing landscape. Historically, access to private markets was typically reserved for institutional investors. Today, Carlyle is opening select private market capabilities to the wealth channel, all while raising the bar on transparency and education.

    We discuss the shifting market environment, explain why the term “alternatives” has become anachronistic, and dig into what “responsible democratization” really requires: specific fund structures (think evergreen/perpetual vs. interval funds), liquidity education, disclosure, and portfolio construction that behaves differently than it does in the public markets.

    Shane explains areas which areas he thinks may see the most growth in the near term, and we dig into what allowing individuals to access the private capital markets via defined contribution plans (i.e., 401(k) investments) *might* mean for everyday investors should those changes come to pass.

    This is also a “Distribution 101” playbook, where we learn the ropes of a career path that wasn’t even an option to us during our time in the industry.

    If you advise clients or want to work in the private capital ecosystem, take note. Carlyle is changing how the world accesses the private markets, and this episode will change how you think about private capital altogether.

    TWSS is not a client of, or investor in funds managed by, Carlyle. Compensation was paid in connection with this social promotion. Statements made reflect the opinion of the speaker(s) and may not be representative of all views, and compensation may give rise to conflicts of interest. Nothing herein constitutes an offer to sell, or a solicitation

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    1 h y 3 m
  • 190. Breaking Down Meta and xAI's "Creative" Off-Balance-Sheet Data Center Financing Plus Deep Dive into The Fed's Insane Press Conference
    Nov 1 2025

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    In this week’s episode, we get into the Fed’s 25 basis point rate cut, Powell’s chaotic press conference before diving into Meta’s creative data center financing which is a lesson on project financing and lease accounting, and finally the growing blur between public and private credit.

    The Fed’s October meeting delivered the expected 25 bps cut but Powell’s tone afterward left markets rattled. While announcing a pause in quantitative tightening, he hinted that December isn’t a done deal, sparking confusion and volatility. Jen breaks down the mechanics behind QT, the Fed’s balance sheet strategy, and why even subtle changes in how they handle T-bill reinvestments could ripple across the yield curve.

    Then we shift to earnings season and Meta’s fascinating case study in project finance. Their $30 billion Hyperion data center project with Blue Owl blends corporate finance, lease accounting, and private credit innovation, raising questions about off-balance-sheet leverage, credit spreads, and who really wins in these structures.

    We wrap with thoughts on how every firm on Wall Street is morphing into everything else—private credit arms at hedge funds, PE firms doing lending, and why that might both dilute and amplify systemic risk. All that, plus Halloween costumes, pumpkin parades, and the realities of parenting in chaos.

    Learn more about 9fin HERE

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    54 m
  • 189. Private Equity | Growth Equity Value Creation with Sixth Street's Paul Dodd | Business Operations 101 (Part 2 of 2)
    Oct 25 2025

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    This week, we’re joined by Paul Dodd, Senior Operating Partner and Head of Go-to-Market Operations at Sixth Street, one of the most respected private credit and private equity firms in the world. This episode is Part 2 of our Business Operations 101 series, and we’re digging into how firms like Sixth Street actually create value inside the companies they invest in. Paul specializes in helping tech and SaaS businesses scale efficiently, so instead of talking about dealmaking, we’re talking about what happens after the deal closes: how to turn strategy into growth.

    Paul walks us through what “go-to-market” really means in practice, from aligning sales and marketing to optimizing customer retention and pricing. He explains how small operational improvements, like shortening onboarding time or using AI to coach sales teams, compound into massive enterprise value during the investment period. We also get into how Sixth Street’s operating and deal teams work hand-in-hand, why culture and process discipline matter as much as capital, and how flexibility in capital structure allows them to back great companies through every stage of growth.

    And finally, we tackle the viral headline of the week: OpenAI is hiring ex–investment banking analysts and MBAs to remove the "drudgery" of junior banking work. We break down whether AI can really replace analysts, why building financial models is still critical to learning the business, and what it means for the future of entry-level Wall Street jobs.

    Paul Dodd is a Go-to-Market, Operating Partner at Sixth Street focused on providing core expertise to organizations in order to maximize revenue generation and profitable growth.

    Before joining Sixth Street, Paul served as Chief Growth Officer at SecureLink, SVP of Sales for Compeat Tech, Head of Sales for the GA360 Measurement Suite at Google, and previously served as Vice President of World Wide Sales at Adometry, a leading provider of multi-touch attribution & cross-channel intelligence, acquired by Google in 2014. Before Adometry, Paul served as Vice President of Sales for Retail at Bazaarvoice and as Chief Strategy & Global S

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    1 h y 35 m
  • 188. Why Apollo Was Blacklisted By First Brands, Credit Market Chaos Continued Plus Business Operations 101 (Part 1 of 2)
    Oct 18 2025

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    In this episode, we sit down with Don Kieffer, senior lecturer at MIT Sloan School of Management and co-author of There’s Gotta Be a Better Way, to talk about what actually makes companies run well. Don has spent decades helping organizations, from Harley-Davidson factory floors to biotech labs, design better systems that unlock real performance. We break down the five-principle framework he developed with his co-author, Nelson Repenning, an MIT PhD, MIT Sloan professor, and leading expert in operations and systems thinking, for building operational excellence: solving the right problem, structuring for discovery, connecting the human chain, regulating for flow, and visualizing the work.

    Through stories that range from front-desk hotel check-ins to a corrugated cardboard plant and even private equity fundraising pipelines, Don shows how tiny operational tweaks can deliver huge impact. We explore why firefighting cultures keep companies stuck in a “capability trap,” why automation without fixing the human system first is a mistake, and why the best private equity playbooks focus on execution, not spreadsheets. For founders, operators, and investors alike, this is a practical, no-fluff conversation about how businesses actually scale.

    Before diving into operations, we also touch on recent rumblings in credit markets, continuing our discussion on the failed refinancing of First Brands and the liquidation of TriColor to bank fraud write-offs and how credit default swaps can amplify market stress. It’s a lively, two-part arc: first, the operational playbook; next, how top investors at Private Equity firms think about value creation inside portfolio companies.

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    1 h y 13 m
  • 187. Breaking Down the Trade That Cost Wall Street a QUARTER BILLION dollars, Plus First Brands Bankruptcy & Gold at Record Highs
    Oct 10 2025

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    This week on The Wall Street Skinny, we kick off discussing gold ripping to record highs and unpack why that’s happening in a still-high-rate world: sticky inflation keeping real yields muted, central-bank buying, safe-haven demand, and a dash of retail frenzy. We also poke holes in the “25/25/25/25” portfolio meme (equities/bonds/cash/gold) and talk through why allocation can’t be one-size-fits-all—age, goals, and cash-flow needs matter.

    Then we dive into First Brands’ Chapter 11 and the alleged “Enron-style” shenanigans behind $2.3B of vanishing assets. We explain collateral, receivables/inventory financing, why overlapping pledges are a five-alarm fire, and who’s exposed (private credit funds at Street names like Jefferies and UBS get a mention). Bigger picture: what this says about today’s credit boom, looser covenants, and why fraud tends to surface when the cycle turns—plus what two auto-related bankruptcies might signal about the consumer/auto complex.

    We also decode that viral “Ferrari-loving trader” headline: how a naked short in long bonds around the COVID shock morphed into an 11,000-to-1 leverage debacle and ~$250mm in Street losses—complete with a plain-English walk-through of bond shorting, repo, and settlement. Finally, we react to the Centerview analyst lawsuit over sleep accommodations and the perennial debate over banking culture, expectations, and realistic boundaries. Stick around for what’s next: a Distressed Debt 101 primer in November and a packed slate of heavyweight guests.

    Learn more about 9fin HERE

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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    52 m
  • 186. Quant Investing 101 feat. PGIM’s Head of Quantitative Equity, Stacie Mintz
    Oct 6 2025

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    What does it really mean to be a "quant investor"? How do quantitative strategies fit into a modern portfolio? And what does it take to break into a quant investing career path?

    In this episode, we sat down with Stacie Mintz, Head of Quantitative Equity at PGIM (one of the world's largest asset managers, with $1.4tr in AUM). Stacie's team oversees $60bn in quantitative equity strategies, and she joins us to break down what quant investing is, how it differs from other investment philosophies, what the role of human oversight is relative to AI, and what skills are essential for breaking into the field.

    From factor investing and natural language processing to how quants think about risk and portfolio construction, this is a no-nonsense inside look at the world of systemic investing. We also do some myth busting work (spoiler alert: quant investing isn't just AI and algorithms gone wild), the evolving role of artificial intelligence, and why communication skills often matter just as much as your coding ability.

    Whether you're just starting out in your career or you're an investor trying to understand how systematic strategies complement traditional fundamental analysis, this conversation is a crash course in Quant Investing 101.


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    Wealthfront.com/wss. This is a paid endorsement for Wealthfront. May not reflect others’ experiences. Similar outcomes not guaranteed. Wealthfront Brokerage is not a bank. Rate subject to change. Promo terms apply. If eligible for the boosted rate of 4.15% offered in connection with this promo, the boosted rate is also subject to change if base rate decreases during the 3 month promo period.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of 11/7/25, is representative, requires no minimum, and may change at any time. The APY reflects the weighted average of deposit balances at participating Program Banks, which are not allocated equally. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Sources HERE.

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    53 m