1. Mark the side-door proxy to the realized IPO price — a full post-listing sum-of-the-parts
The repeatable method
- When the hot private finally lists, immediately re-mark the listed company that holds a stake in it. Build the holder's NAV bottom-up: (a) the stake at the realized price, with an explicit liquidity discount; (b) every other monetizable asset; (c) less debt, cash adjustments, and the taxes owed on asset sales.
- Be conservative on every line — a discount on the IPO shares, distressed marks on speculative assets, deduct deal-related costs — so the residual NAV survives scrutiny.
- Express the gap as a discount to the close; if it's wide and the IPO float is tiny (so the stake's mark can still rise into the unlock), it's a lower-beta way to stay long the story you wouldn't pay sticker for.
Here: with SpaceX closing ~$161 (~$2.1T), SATS's 2.2% stake = $47B ≈ $114/sh discounted; add ~$73 of net spectrum/cash (AT&T + SpaceX spectrum sales ~$33B, residual ~$8.6B, less ~$14B debt, plus $4.3B cash, less spectrum-sale tax and tower-lease costs) → ~$187 intrinsic vs a ~$114 close = ~40% (mid-40s on after-hours marks).
Watch for
- Listed holders of a just-IPO'd name; remember to subtract the tax on any spectrum/asset monetization — it's the line amateurs skip.
2. When a proxy is irrationally cheap, find the forced flow making it that way
The repeatable method
- If your NAV says a name is far too cheap, ask who is mechanically selling rather than assuming you're wrong. The cleanest source: holders of the locked-up asset who can't sell it and hedge through the most-liquid public proxy instead.
- Confirm with the options tape — a wall of opened puts at a specific strike is the hedging fingerprint, and it depresses the underlying.
- That pressure is temporary and self-reversing (it fades after the unlock), so treat the dislocation as the entry, not a red flag — and hedge your own long with the other names in the complex.
Here: SpaceX longs locked up for six months bought thousands of SATS 110-strike puts (the most-liquid space proxy vs thinner DXYZ/VCX/PWRL), pushing it below $110 intraday — the very reason the discount got so wide.
Watch for
- Unusual put open-interest at round strikes on a liquid proxy; lockups on the underlying that explain the selling and its expiry date.
3. Short the "expensive on sales + outsourced execution" space/AI name
The repeatable method
- Start with the crudest multiple: EV/trailing-sales. A 400×-sales valuation is a flag even before the model — and check whether it stays absurd on the company's own bull guidance (here ~162× even on believed-2027 EBITDA).
- Score execution risk: does it control its own critical path, or outsource it? A company that takes full rocket/launch risk through a single unproven third party has a fragile spine.
- Audit contract quality and cost honesty: how much of the marketed revenue is actually contracted (take-or-pay vs uncontracted), and do recent write-downs contradict the per-unit costs management has sold to retail?
- Time the entry to a catalyst and reload on counter-trend bounces; use it as a hedge against the rest of your exposure to the same theme.
Here: ASTS — ~$32B EV on $84M sales (~400×); all launch risk on Blue Origin, whose New Glenn just exploded (3–6 mo delay); 90% of its $1B target uncontracted; a satellite written off at ~7× its marketed unit cost. Short on a bounce, as a space hedge.
Watch for
- Triple-digit sales multiples; single-vendor launch/supply dependence; gap between "contracted" and "targeted" revenue; write-downs above marketed unit costs.
4. Buy the baby bond, not the common — the BDC loss-given-default screen
The repeatable method
- When a whole sector is hit by headlines, look for the debt of a good operator within it — a baby bond can price ~100 bp cheap on sector panic while sitting senior to the dividend it's mispriced alongside.
- Screen the issuer's portfolio: % senior-secured first-lien, average position size (diversification), non-accrual rate (fair-value and cost basis), regulatory leverage, and weighted portfolio yield vs the bond coupon (coverage).
- Do the LGD math: at a 50% recovery, defaults must run ~2× the loss you'd tolerate. Needing ~30% defaults (≈15% losses) to impair the bond = a wide cushion — buy the bond, avoid the common (which keeps the headline risk).
- Name the one real risk and price its odds: a 100%-floating book is hurt by an aggressive rate-cutting cycle — discount it only if you actually expect cuts.
Here: PFLA (PennantPark 7⅜%) — 87% first-lien, <1% avg position, ~1–1.5% non-accruals, ~11.5–12.3% portfolio yield, 1.2–1.3× leverage → ~30% defaults needed to touch the bond. Likes the bond; avoids ARCC/OBDC-style common on sector headline risk.
Watch for
- New baby-bond issues priced wide in a sector panic; first-lien % and non-accruals vs peers; coupon coverage by portfolio yield; floating-rate exposure into a cutting cycle.
5. "Sell the news" the scarcity premium — listed pre-IPO wrappers collapse on access
The repeatable method
- A listed fund that holds a coveted private trades at a premium because retail can't buy the private directly. The premium is the scarcity, not the asset.
- The IPO itself is the catalyst that destroys the premium: once the underlying is publicly buyable, the reason to overpay for the wrapper evaporates — so the wrappers make their lows into the listing, not after.
- Express via options to define risk; keep the unlock as a second, later catalyst once frozen shares can sell.
Here: on the SpaceX listing, VCX made all-time lows (still >50% below where flagged), SPCE unraveled (shorted into a doubling of pre-IPO implied vol — calls went to ~zero), and PWRL went $25→$19.
Watch for
- Listed pre-IPO funds / closest-comp tickers ahead of a big listing; implied-vol spikes that make short premium rich; the IPO date as the de-rating trigger.
6. Red-flag the circular-financing deal — the guarantor funding its own revenue
The repeatable method
- Trace where the borrowed money actually goes. If a financing for company A sends 100% of proceeds to supplier B, the deal manufactures B's revenue rather than reflecting organic demand.
- Find the guarantor and ask why it would take the risk: a residual-value backstop on chip-collateral debt means the guarantor eats the shortfall if the GPUs/TPUs are worth too little — and if it co-makes those chips, it's underwriting its own sales.
- Count the conflicts and the opacity: same bank advising the guarantor and margin-lending to the buyers; an equity holder doubling as the cloud counterparty; and lenders given no access to the borrower's financials. Each layer raises the bubble reading.
- Scale-check the asset class: AI debt heading to ~$400B → $1T+ by 2028 against a ~$4T US leveraged-credit market is a size/quality mismatch, not a one-off.
Here: the $35B "Big Sky" SPV — proceeds all to NVDA; AVGO backstops the $30B senior tranches on chips it co-makes with GOOGL (which owns 14% of borrower Anthropic and hosts it); Morgan Stanley advised AVGO and lent to the buyers; lenders saw no Anthropic financials.
Watch for
- Proceeds round-tripping to a supplier; residual-value guarantees by a chip co-maker; advisor/lender conflicts; "no financials disclosed" in a debt raise.
7. Watch the redemption gates and the CFO structure — the private-credit tell
The repeatable method
- Ignore the marked-to-model NAVs and watch liquidity: when interval funds receive large redemption requests and honor only a fraction (gate), stress is real even as public equities rally.
- Spot the masking structure: Collateralized Fund Obligations (CFOs) are bonds backed by private-equity stakes that generate no organic coupon — interest is paid only by selling holdings (Ponzi-like), levered ~60%, rated by conflicted small agencies, then stuffed into life insurers (often ceded offshore for more leverage).
- Trace the ultimate bag-holder — retiree annuity/insurance policyholders — and recall the precedent (the SHIP insurer blow-up: ~15¢ on the dollar) to size the tail risk, even if it takes years to surface.
Here: Cliffwater 17% redemptions (honored 7%), B-CRED 10% (~$4.4B; honored 5%), Partners Group gated; Blue Owl OTIC 40% / OCIC 21%, Apollo 12%, HPS 9% — plus $30B+ of CFOs issued YTD into the $10T life-insurance complex.
Watch for
- Interval-fund redemption gates and honor ratios; CFO issuance volumes; insurer offshore reinsurance; rating-agency conflicts (Egan-Jones/KBRA/Kroll).
8. Value the terminal value, not the trailing print — the "toll bridge" test
The repeatable method
- Remember 70–80% of a tech stock's value is cash flows 5–10 years out. A cheap trailing multiple is irrelevant if the future is impaired — "the most dangerous phrase in investing is 'the stock is down but fundamentals are improving.'"
- Run the toll-bridge thought experiment: if a free competitor (here, generative AI) will arrive in five years, intrinsic value falls today even though current profits are unchanged. Apply the historical analogues — newspapers vs the internet, department stores vs e-commerce, cable vs streaming.
- Set the buy condition explicitly: it's a sidelines "cash cow" until there's empirical proof the moat survives (subscriber retention, ARPU expansion, AI as a feature not a killer). Until then, prefer names whose moat AI doesn't threaten.
Here: ADBE at a 12.5% FCF yield (from 2%), 89% margins, ~$11B FCF — statistically cheap, but a textbook terminal-value question, so watch-only. He prefers DDOG/cybersecurity and high-moat compounders (MCO, SPGI); flags V/MA as longer-dated, not near-term, AI/tokenization risks.
Watch for
- Cheap-on-trailing names facing a structural substitute; evidence (or absence) of moat durability; the "cheap and getting cheaper" value trap.
9. Read the volatility "smirk" — retail flow rewires the options curve
The repeatable method
- Don't read the level of vol; read the shape. Post-COVID, retail (now ~32% of equity volume, up from 16%) bids upside calls, so OTM call implied-vol is elevated and downside put-skew premium is compressed — a "smirk," not a "smile."
- Use two gauges: IV/RV (implied vs realized — 1.4–1.5× here vs a 1.2–1.3× norm signals people buying ATM vol just for leverage) and CBOE SKEW (136 vs an 118–125 norm).
- Discount the lazy "VIX suppression" narrative: 0DTE gamma compresses short-end vol while the call-side bid and put-selling drive the surface — so structure hedges and leverage around the real flow, not the headline.
Here: the smirk explained the week's whippy single-name moves and is "an astute observation" he'd use to price hedges; single-name IV premium over the index hit a ~12-year high pre-treaty.
Watch for
- Call-side skew > put-side; IV/RV and SKEW above norms; 0DTE share of volume; single-stock-vs-index vol premium at extremes.
10. Trace the geopolitical catalyst through the macro chain — and buy the cyclical-peak yield
The repeatable method
- "Rates drive the world and the war drives rates." Start from the catalyst (a peace treaty) and follow the chain: oil down → dollar down → rates down → rate-sensitive value, EM, gold/precious metals, spec tech and crypto up.
- Separate the cyclical shock from the structural backdrop: even with a treaty, sticky inflation (46/68 banks overshooting, an 8.2% 3-month annualized run-rate) and a hawkish-hold Fed mean cuts aren't coming soon — so position for lower long rates via the growth/peace channel, not via Fed easing.
- When you judge yields at a cyclical peak (10-yr ~4.5%, 30-yr ~5%) and the inflation shock is receding, reinitiate the long bond — and lean the equity book toward beaten-down non-tech longs that benefit from the same rotation.
Here: the treaty rotation → reinitiate TLT; rotate into rate-sensitive value (CVS, REITs/banks/healthcare) and trim extended mega-cap tech into the melt-up.
Watch for
- Oil/dollar/10-yr reaction to the catalyst; the gap between cyclical relief and structural inflation; central-bank guidance; the retail-sales print for consumer follow-through.
Methods distilled from the premium Special Situations Report weekly call (transcript & report PDFs in this folder; notes in transcript.md) for personal study. Not investment advice. © Special Situations Report for source material.