What's The Big Deal?

Wall Street Prep
  • 4.0 (8)
  • Investing
  • Updated Weekly

Get the view from the inside. Every week, Graham Smith (ex-Ares) and Deborah Taylor (ex-Barclays) take a look at Wall Street’s headline-grabbing deals.  From mega-mergers and hostile takeovers to complex private credit transactions, they break down the why, the how, and the who behind the numbers.

  1. 2d ago

    Investment Banking: Claude Fable 5 Just One-Shotted a Bulge Bracket-Grade DCF

    Six weeks ago, Debs and Graham asked Claude Opus to build a DCF. The result got a B-minus from Graham and a C from Debs. Missed calculations, questionable assumptions, no clear reasoning on why it was cutting corners.  This week they ran the exact same test — same prompt, same company, no additional guidance — on Anthropic's newest model, Fable 5. The result was a step-change neither Graham or Debs expected. In this episode, Debs and Graham walk through the Fable 5 output in detail. Mid-year discounting handled correctly from the start ("it actually knows how investment bankers think").  Terminal value presented in two methods, perpetuity growth and EBITDA multiple, side by side. Weighted average cost of capital coming in at 10.6%, in line with typical investment banking assumptions.  Diluted share count calculated correctly with buybacks accounted for. The model even self-corrected mid-build when it detected a formula error. The Lululemon test produced a striking finding: the DCF implied 45% upside to the current share price, suggesting the market may have Lululemon materially wrong.  Six weeks ago, Claude Opus solved for a value in line with the current share price. This time, Fable 5 took a genuine view — it saw upside and said so. They also cover the broader context: CVC's Wall Street Journal-covered use of an AI agent in the Sproutz sale process, what that means for banker fees, and Graham's real-world observation that AI has moved from being a calculator to genuinely forming views on valuations. The verdict: A-minus from Graham, B-plus from Debs.  Graham's honest closing question: at $50 in credits per model, is DIY still faster? Fable 5's fate as Anthropic transitions it to usage-only pricing is genuinely uncertain, but the six-week leap the episode captures is not. Key Discussion Points: The six-week transformation: from B-minus/C on Claude Opus to A-minus/B-plus on Fable 5.  What Fable 5 is: Anthropic's newest release, its release history, and its credit-limited launch.  Mid-year discounting, terminal value approaches, and WACC calculations Fable 5 handled correctly.  The self-correction moment: AI detecting and fixing its own mid-build error.  The Lululemon finding: 45% implied upside to the current share price.  AI going from calculator to view-taker: what that shift means for how models should be used.  CVC's Sproutz sale process: AI agent in the data room, and what it signals for banker fees.  The debt-treatment miss: Fable 5's blind spot on lease liabilities.  The economic question: at $50 in credits per model, is DIY still faster? WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  2. Jul 9

    Private Equity Faces a 9-Year Backlog. Here's Why.

    US private equity firms now face a 9-year backlog of unsold portfolio companies at the current pace, according to new PwC and PitchBook analysis. Roughly 13,500 companies sit in PE portfolios as of June 30, with nearly 4,000 held for 6+ years and 1,500 held for 9+ years.  Fundraising has collapsed alongside, with only $159.6 billion raised in H1, on track to match 2025's muted total. In this episode, Debs and Graham dig into Bain's private equity report and unpack the structural pressures behind the slowdown, which explain why financial sponsor transaction volume is down 9% year-on-year even as broader deal activity has hit records. The conversation opens with the strategic vs. financial buyer dynamic. In a period of uncertainty, financial sponsors are more resistant to defensive punts because they need to underwrite specific return targets in a highly uncertain environment.  Beyond the motivational split, Graham walks through the structural pressures on PE returns. Cost of leverage has risen with floating-rate debt getting more expensive in a hawkish rate environment.  Purchase price multiples remain elevated (Bain calls it a "deal cost index" at all-time highs). High entry combined with high cost of debt makes it structurally harder to underwrite the returns PE requires. Software exposure is the other major theme. PE has historically been overweight software for good reasons (cash-generative, recurring revenue, pricing power), which now looks vulnerable to what one analyst calls the "SaaS-alypse", the fear that AI will destroy the software space overnight.  Graham is skeptical the collapse will be as sudden or sweeping as the narrative suggests, but the fear alone is enough to spook LPs and put pressure on private credit funds that back PE deals. The result is a broader machine slowdown. Holding periods have extended from the traditional 5 years to 7 years on average, which erodes IRR. LPs aren't getting their capital back at expected pace.  New fundraising is more difficult. Only the highest-quality assets are trading, which means the remaining book is likely lower-quality than the marks suggest, creating further LP hesitation. Continuation vehicles have become one workaround, but Graham flags that they carry their own LP concerns around marking and capital return.  The episode closes on what would need to change: more clarity on the software/AI trajectory, and PE firms doing what they can, running existing assets as well as possible until exit conditions improve. Key Discussion Points: The 9-year backlog: 13,500 portfolio companies and a fundraising collapse to $159.6bn in H1Strategic vs. financial buyers in uncertainty: why sponsors sit tight while corporates moveCost of leverage pressure: floating rates and rising interest bills eroding equity returnsThe Bain "deal cost index" and elevated purchase multiplesSoftware exposure and the "SaaS-alypse" fear: overblown or real?Extended holding periods (5 years to 7 years) and IRR compressionThe best assets sold first: what that means for LP confidence in remaining marksContinuation vehicles: solution or symptom of the broader slowdown?What could restart the PE deal machineWhat's the Big Deal? is an educational podcast covering deals and market developments in public and private markets. Nothing in this episode constitutes financial advice. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  3. Jul 2

    Global M&A Just Hit a RECORD $2.8 TRILLION. Here's What's Driving It.

    Global M&A hit a record $2.83 trillion in H1 2026, the highest total since records began, eclipsing the 2021 peak of $2.74 trillion.  Deal values in Q2 alone were up 41% year-on-year, deal count up around 10%, mega deals continue to dominate, and small-cap and venture activity is up 200%.  But the picture underneath the headline numbers is more complicated, and both think the drivers behind the surge may not last into 2027. In this episode, Debs and Graham work through Bain's mid-year M&A report and unpack the themes behind the numbers.  They open with market context: SpaceX post-IPO with the share price now below $160 and the first lock-up expiries approaching, the AI mini-correction of June driven by CapEx discipline concerns, Meta joining xAI in selling excess compute capacity, and news of a Chinese frontier model claiming performance at 10% of the cost of leading Western models.  The M&A conversation itself focuses on the defensive posturing thesis. With geopolitical, business model, and AI-disruption uncertainty at unusual levels, large corporates are buying up smaller disruptive companies as insurance against being outmaneuvered.  The 200% increase in small-cap and venture activity supports the read. Debs highlights the awkward setup for a typical M&A cycle: hawkish interest rate environment, frothy sector valuations, and low certainty, none of which usually correlate with peak deal activity. The sector-by-sector split reveals financial services quietly lagging the broader market. Graham & Debs speculate on why, and neither has a strong answer.  Europe is the standout regional performer, driven partly by the valuation gap versus the US (roughly 15x forward P/E versus 22x) and partly by the possibility that acquirers are moving now ahead of a mooted merger benefit test that could add a second regulatory hurdle to European deals. The episode closes on H2 predictions.  Debs is skeptical the second half will match the first, citing hawkish rates, frothy valuations, and the pent-up demand carrying over from 2025 already being absorbed.  Graham expects continued growth from the existing pipeline but flags 2027 as the genuine question mark: once the current pipeline works through, whether the fundamentals actually justify M&A at this level is an open question. Key Discussion Points: Global M&A hits record $2.8 trillion in H1 2026Q2 stats: deal values up 41% YoY, deal count up ~10%, mega deals dominatingThe defensive M&A thesis: uncertainty as a driver of acquisition activitySmall-cap and venture activity up 200%: what it signals about corporate defensive posturingThe sector-by-sector split: energy and industrials leading, financial services quietly laggingEurope outperforming: valuation gap, competition clearance, and the potential merger benefit testMarket context: SpaceX post-IPO dynamics, AI selloff drivers, Meta's excess compute sale, and the Chinese model storyH2 2026 and 2027 predictions: pent-up demand vs. fundamentalsBain M&A Report: https://www.bain.com/insights/m-and-a-midyear-outlook-2026-a-winners-paradox/ WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  4. Jun 25

    Private Equity vs. Private Credit Explained in 15 Minutes

    Two of the biggest growth areas in finance over the last decade, but the differences between private equity and private credit are often misunderstood, especially by candidates trying to decide between them.  In this episode, Debs sits down with Graham, who spent a decade at Ares Management for a Q&A-style explainer that breaks down what each actually is and how the day-to-day differs. Graham starts with the fundamental distinction: private equity invests in companies that don't trade on the public market, private credit makes illiquid loans to those companies. From there the conversation moves through the deeper differences.  The motivation gap, where equity investors are hunting for upside and credit investors are protecting capital because their upside is contractually capped. The return profiles, with PE targeting 15%+ IRRs at the asset level versus credit closer to high single digits to low double digits, and how private credit funds use fund-level leverage to amplify those returns. The conversation then turns to how the two sides actually interact. Graham flags that he never saw a firm finance its own PE deals with its own credit fund and that the base case is keeping the two operations independent.  He explains how closely PE sponsors and credit providers negotiate during deal-making, what makes a company attractive to both sides simultaneously (recurring revenue, cash flow visibility, growth prospects), and why the diligence focus differs significantly. Equity focuses on the upside thesis, credit focuses on every way you could lose money. The episode closes on career-relevant differences. Single-deal depth in PE versus higher deal flow in credit, the generalist versus specialist question, and how the route into both has fundamentally changed since Graham's own start at Lehman Brothers in the mid-2000s. Key Discussion Points: The fundamental distinction: investing in companies vs. making illiquid loans.  Motivation gap: upside potential vs. capital preservation, and what capped upside means in practice.  Return profiles: 15%+ IRR in PE vs. high single digits to low double digits in credit, plus how fund-level leverage closes some of that gap.  Firm independence: why PE and credit arms within the same firm don't typically finance each other's deals.  Deal mechanics: how PE sponsors and credit providers negotiate, and what makes a company attractive to both sides.  Diligence focus: market opportunity vs. downside protection, and how the two diligence mindsets differ.  Career-relevant differences: deal flow, depth vs. volume, generalist vs. specialist, and how to break in today. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  5. Jun 18

    EX-BANKERS EXPLAIN: Investment Banking Mistakes To AVOID In Your First Year

    It's summer training season. Both Debs and Graham are spending their days running analyst and associate programmes at major firms, which makes this the right moment to step back from the deal-of-the-week format and share the kind of candid advice they wish someone had given them on day one. Graham opens with his own first-year story at Lehman Brothers in 2005, including the pitch book error that earned him an hour-long dressing-down from a VP, and uses it as the entry point to a broader conversation about attention to detail and why the technical work in finance is genuinely not the hardest part of the job.  Debs shares her own near-career-ending moment publishing a flawed research screen as a new associate, and reflects on how she recovered, what her boss told her, and why trust, once lost, takes years to rebuild. From there the conversation moves through the practical advice that gets harder to find as classes get larger and firms get bigger.  How to tell the difference between a recoverable mistake and a career-ending one. Why finance math is simple and getting stuff done well is the actual skill.  How to ask questions that add value versus questions that just take up airtime. Why prep before meetings is the easiest way to stand out, why sharp elbows are usually the wrong instinct, and why being a team player matters more than being the smartest person in the room. The episode closes with their personal survival tips: physical activity, availability, sleep, calendar discipline, and showing up to everything you can.  The kind of advice that sounds basic but separates the analysts who get the return offer from the ones who don't. Key Discussion Points: Attention to detail: why the costs of getting it wrong are high, and how AI changes (but doesn't reduce) the standard.  Recoverable vs. career-ending mistakes: how to tell the difference and what to do in each case.  The technical work is the easy part: why getting stuff done well is the real skill.  Asking questions that add value: how to demonstrate engagement without taking up airtime.  Standing out without sharp elbows: why being a team player and showing up consistently is the most underrated path.  Survival habits: physical, mental, calendar, sleep, and the practical mechanics of not burning out. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  6. Jun 11

    The $1.75 Trillion SpaceX IPO: Everything You Need to Know.

    SpaceX begins trading on Friday at a $1.75 trillion valuation, and the deal looks unlike any major IPO that has come before it.  In this episode, Debs and Graham go inside the prospectus, break down the unusual structural features Elon Musk has pushed through, and debate whether the valuation can be justified. The mechanics alone are remarkable. The IPO is being priced at a fixed $135 per share rather than through a traditional book-build range, putting all of the price risk onto buyers and signalling unusual confidence from the issuer. The free float is less than 5%, which sets up potentially significant post-listing volatility.  Retail investors have been given 30% of the allocation, roughly three times the typical share, raising the question of whether this is genuine democratisation or simply exit liquidity for early holders.  The dual-class share structure leaves Musk with 85% of the voting power despite owning around 45% of the economics.  And the underwriting fee, agreed across a syndicate of 23 banks, has come in at 0.75%, the lowest on record for a deal of this size. The valuation discussion centres on the TAM chart in the prospectus. SpaceX has positioned itself less as a launch and communications business and more as an AI infrastructure and applications story, with $26.5 trillion of AI revenue underpinning the case for the headline number, including $22.7 trillion in enterprise applications alone.  Debs and Graham draw the parallel to the Tesla IPO, where the company was reframed from auto to tech in order to unlock a tech multiple. They also reference Aswath Damodaran's published view that the realistic AI TAM is closer to $5 trillion, and Morningstar's estimate that the fair value of the business is roughly half the IPO valuation. The episode closes on what to watch when trading begins. With oversubscription pointing to a potential pop, but a low free float, a 180-day staggered lock-up creating an overhang, and the Nasdaq 100 fast entry expected to trigger $30 to $50 billion of forced buying, the first six months are likely to be unusually volatile. Both hosts agree the outcome is genuinely unpredictable. Key Discussion Points: The fixed-price IPO mechanism, why it's unprecedented at this scale, and what it signals about the issuer's confidence.  The structural risks: low free float, large retail allocation, dual-class shares and lock-up dynamics.  The fee anomaly: 23 banks, 0.75% — the lowest on record for a mega-deal.  The TAM debate: $23 trillion in the prospectus versus Damodaran's $5 trillion estimate, and how the AI bucket drives the valuation.  The Tesla parallel: reframing the business to land a tech multiple.  What to watch in early trading: oversubscription, index inclusion fast entry, and the 180-day lock-up overhang. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  7. Jun 4

    Will the $4 Trillion AI IPO Wave Break the Market? SpaceX, OpenAI & Anthropic

    Three mega IPOs are heading to market: SpaceX, OpenAI and Anthropic. Between them they could push the largest tech names to nearly half of the S&P 500, at valuations that have drawn obvious comparisons to the dotcom era. In this episode, Debs and Graham debate whether those comparisons hold, and where they break down. They start with the triggers: extreme index concentration, the scale of the valuations being floated, and the structural role of index funds that are obliged to buy these companies once they join the benchmark.  They then look back at the dotcom boom and bust, drawing lessons from failures like Web Van and Pets.com, businesses whose underlying ideas were sound but whose execution and unit economics were not, and the survivors like Amazon and eBay that collapsed before figuring out their models. The core of the episode is a genuine bull versus bear debate. Debs makes the case that 2026 is not 1999: the S&P trades at around 23 times forward earnings against a long term average near 18, a world away from the Nasdaq's 60 times in 1999, and today's dominant AI names generate real profits and cash flow.  Graham presses the bear case: the CapEx burn behind the AI build-out is enormous, run rate revenue is not a GAAP concept and is open to management, and the return on all that data centre spending remains unproven. They agree the sharpest risk is concentration. With AI-focused names potentially approaching 50% of the index, a miss on a few key data points could move the entire market. They close by each picking the IPO they would back today. Both land on Anthropic, citing a more measured profile and the principle that being first is not the same as being best, while acknowledging that the real financial picture for OpenAI and Anthropic will only become clear once their S-1 filings arrive. Key Discussion Points: The three mega IPOs: SpaceX, OpenAI and Anthropic, and the valuations being floated.  Concentration risk: the Magnificent Seven, index fund mechanics and the path toward 50% of the S&P 500.  Lessons from the dotcom crash: why execution and unit economics mattered more than being first. Valuation reality check: forward earnings multiples today versus 1999.  The bull case: real profits and cash flow among today's AI leaders.  The bear case: CapEx intensity, run rate revenue scrutiny and unproven returns.  The IPO process: where SpaceX, OpenAI and Anthropic each sit, and why the S-1 filings matter.  The verdict: which IPO each host would back and why. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

  8. May 28

    Can Claude Replace Investment Bankers? We Graded the Output.

    How good is AI at building a DCF?  In this episode, Debs and Graham continue their Claude for Excel series, this time prompting the tool to construct a full discounted cash flow valuation for Lululemon from a single instruction.  The goal is to test what AI can and cannot do in real valuation workflows, and what that means for analysts working in equity research, investment banking and M&A. Graham walks through DCF fundamentals from first principles, covering future cash flow projections, WACC, terminal value and the inputs that genuinely drive valuation outcomes.  He then opens Claude for Excel and gives it a structured prompt — anchored to consensus EPS estimates for stage one, with explicit instructions on modelling best practices including no hardcoded inputs in formulas, standard colour coding, and transparent assumption sourcing. The audit that follows is instructive on both fronts. Claude handles the structural build well — linking assumptions to formulas, applying the Gordon Growth formula correctly for terminal value, and producing a workable enterprise value output.  But the limitations show up in the details that matter most for senior review: the free cash flow build conflates levered and unlevered measures, time period construction is simplistic rather than properly anchored to fiscal year ends and a valuation date, and some formula constructions are opaque enough that auditing them line by line would take longer than rebuilding the section manually. The verdict: a B-minus output.  Workable as a first pass, but not yet at the level where it can be submitted without significant human review.  The broader question the episode closes on is whether AI tools like Claude for Excel are positioned to replace the analyst role or to elevate it — with Graham making the case that the analyst job as historically defined is exactly the workflow these tools are now competent at, while the judgement-heavy associate role remains some distance from being automated. Key Discussion Points: DCF fundamentals: future cash flows, discount rates, terminal value and the inputs that actually drive valuation outcomes.  Prompting strategy: how to structure a Claude for Excel prompt to anchor projections to consensus estimates and enforce modelling best practices.  Where AI delivers: structural build, formula linking, Gordon Growth application, sensitivity analysis output.  Where AI falls short: free cash flow build, time period construction, opaque formulas that resist quick audit.  Sensitivity analysis: long term growth rate versus WACC as the two real swing factors in any DCF.  AI in finance careers: the analyst role versus the associate role and what realistic automation looks like over the next 12 to 24 months. WTBD Newsletter: https://webmail.wallstreetprep.com/whats-the-big-deal Follow Us On Socials: LinkedIn: https://www.linkedin.com/company/wall-street-prep/ Instagram: https://www.instagram.com/wallstreetprep/ Resources: https://linktr.ee/wallstreetprep

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Ratings & Reviews

4
out of 5
8 Ratings

About

Get the view from the inside. Every week, Graham Smith (ex-Ares) and Deborah Taylor (ex-Barclays) take a look at Wall Street’s headline-grabbing deals.  From mega-mergers and hostile takeovers to complex private credit transactions, they break down the why, the how, and the who behind the numbers.

Information

  • Creator
    Wall Street Prep
  • Years Active
    2026
  • Episodes
    18
  • Rating
    Explicit
  • Copyright
    © 2026 What's The Big Deal?
  • Show Website
    What's The Big Deal?

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