1. The "double-cheap" cyclical screen — low price-to-sales AND low PE at once
The repeatable method
- In a cyclical industry, don't lead with the PE — earnings swing too much, so a high PE at the trough and a low PE at the peak are both traps. Anchor on price-to-sales instead, which is far steadier across the cycle.
- The classic buy signal is a low price-to-sales while the PE is optically high (depressed trough earnings). The rarer, stronger signal — the "double win" — is when BOTH price-to-sales and PE are low at the same time, which usually means the market has simply abandoned the name.
- Treat valuation as the "cherry on top," not the thesis. Get excited about the fundamentals turning first; let the cheapness be the margin of safety, not the reason.
Here: the lead-gen names (QNST ~4× EV/EBITDA, EVER 3.7× cash flow, MAX 5–6×) screen low on both price-to-sales and PE just as their businesses inflect — David Hay's "double win… quite unusual."
Watch for
- Cyclical names where price-to-sales sits near a multi-year low while the PE looks high or normal — and especially the rare case where both are low.
2. Buy operating leverage at the cyclical trough — but only with a secular tailwind underneath
The repeatable method
- Inside a recovering cycle, find the operating-leveraged way to play it — the smaller, asset-light supplier whose profits swing far more than the big incumbent's when volumes return (more upside than owning the incumbent directly).
- Demand a second, non-cyclical growth driver underneath it, so you're not just renting a cycle. The ideal is a multi-decade secular shift that keeps compounding regardless of where the cycle sits.
- Time the entry to the cyclical trough (depressed stocks, brakes-on demand) while the secular driver is visibly accelerating — both winds at your back at once.
Here: lead-gen marketplaces are the operating-leveraged play on the auto-insurance up-cycle, sitting on a 20-year demographic shift (Gen X/Y/Z buying insurance online, never via a live agent) — "a super cycle… going to last another 20" years.
Watch for
- Suppliers/marketplaces to a cyclical industry that also ride a one-way adoption curve (online migration of a previously offline transaction); the cycle bottoming as the catalyst.
3. The AI-victim / AI-neutral / AI-winner triage — find the crushed-but-fine companies
The repeatable method
- Start from the observation that AI/LLM fear has indiscriminately crushed a long list of fine companies — so the inefficiency is in sorting them, not in the fear itself.
- For each beaten-down name ask: is it an AI victim (disintermediated/disrupted), AI neutral (AI neither helps nor hurts), or an AI winner (AI makes it more valuable)? Buy the neutral and the winners that the market has mis-sorted as victims.
- Cross-check the company's own words: read the recent earnings calls where management answers the AI-threat question directly, and weigh whether the threat is real or a narrative spillover from an unrelated scare (e.g. the "software/SaaS" de-rating).
Here: the lead-gen names "got lumped in with the software and SaaS scare, but it's so different" — Sy reclassifies them as AI beneficiaries (LLM price-comparisons become a new lead source), making them mis-sorted "AI victims."
Watch for
- Stocks down on an AI narrative that doesn't actually touch their economics; management's call-by-call answers to the AI-threat question as the tell.
4. The regulatory / proprietary-data moat test — can an LLM actually disintermediate this?
The repeatable method
- When the fear is "LLMs will disintermediate them," check whether the critical input is actually obtainable by an LLM. If the value sits in proprietary, closely-guarded data or pricing, the LLM can't replicate it.
- Look for a structural lock: state/federal regulation, trade secrecy, or a counterparty (here the carriers) with a strong incentive to keep its "secret sauce" off any public utility — and regulators who agree.
- Then flip the question: if the LLM can't replace the chokepoint, does the LLM instead feed it? A new top-of-funnel source of demand is a tailwind, not a threat.
Here: carriers won't expose their state-regulated, decades-honed pricing algorithms to an LLM, and "state regulators wouldn't want that either" — so LLMs become "an ally," delivering qualified leads the exchanges are uniquely licensed to bind.
Watch for
- Businesses whose moat is regulated/proprietary data an LLM can't access; whether the LLM ends up as a new demand source rather than a substitute.
5. Hunt orphan stocks by mapping who covers them (and who doesn't)
The repeatable method
- For an unloved small-cap, list the sell-side analysts covering it and what desk they sit on (tech/internet, business services, financials, insurance).
- An "orphan" is a name covered by the wrong specialty — IPO'd as one kind of business, but its real economics belong to another sector the covering analysts don't understand (and the right-sector analysts ignore).
- That coverage mismatch is the edge: come at it with the correct analytical frame the consensus lacks, and accept that sub-$1B caps with three-to-five analysts will stay mispriced longer.
Here: lead-gen names were taken public as "internet services plays" at big multiples; tech analysts were "dismayed to learn there's an insurance cycle" — so they're covered by neither insurance nor financial-services analysts. Sy comes at them as a financials specialist.
Watch for
- Sub-$1B caps whose covering analysts are from the wrong sector; an IPO-era classification that no longer fits the business.
6. Score the capital allocator — and ride a disciplined anchor shareholder
The repeatable method
- Among similarly cheap names, rank by capital management: who is actually buying back stock at a low multiple versus who is hoarding cash with no plan.
- Prefer the one with a disciplined, buyback-minded anchor shareholder on the board — a large, proven serial-repurchaser whose track record signals the cash will be returned at accretive prices.
- Where management is hoarding, treat engagement as part of the thesis: push them (directly) to return capital; size the position partly on the odds of that change.
Here: MAX (White Mountains owns 30% + board seat; doubled buyback authorization to $86M) gets a bigger weight than the even-cheaper EVER, which is hoarding cash — so Sy is flying to EverQuote's HQ "to push them to buy back more stock."
Watch for
- Cheap stocks with a serial-buyback anchor holder; rising buyback authorizations relative to cash; cash-hoarders where activism could unlock value.
7. Long/short ambidexterity buys patience
The repeatable method
- Run a genuine short book (here ~50%) alongside the longs — own the undervalued/underappreciated, short the overvalued/overappreciated.
- Use the opposite book as psychological ballast: holding a multi-year cyclical long is easier when an offsetting short portfolio means a market drawdown isn't pure pain — which lets you wait out the re-rating instead of being shaken out.
- Keep the macro footprint small: don't need a market-direction call if the long and short legs are each right on company-specific fundamentals.
Here: Sy holds the lead-gen longs through a frustrating divergence (carriers outperformed) because "being ambidextrous on the long-short side allows you to be a more patient investor."
Watch for
- Whether your sizing/temperament lets you add to a working thesis during a drawdown; an offsetting book as the enabler of patience.
8. Sell discipline — exit when a cyclical re-rates to a "normal" multiple
The repeatable method
- Define the exit before you own it: a cheap cyclical is held until the market stops treating it as fully cyclical and re-rates it to the double-digit EV/EBITDA "most companies" get.
- The signal to sell is the re-rating, not a price target — once you "can no longer steal them," the asymmetry is gone.
- For carriers/incumbents, use a "mission-accomplished" rule: scale out as the cyclical thesis fully plays out (a double from the trough) and rotate proceeds into the names with more upside left.
Here: Sy will sell the lead-gen names "when they trade at double-digit multiples of EBITDA"; he's already trimming PGR and ALL after each roughly doubled — "close to a mission-accomplished situation."
Watch for
- A formerly-orphaned cyclical re-rating toward peer multiples; a position that has doubled on the cyclical thesis as the trim trigger.
9. Validate EBITDA as a proxy only when it ≈ free cash flow
The repeatable method
- EBITDA is a flawed shortcut (Buffett's critique) — it adds back real costs. Only trust it as a valuation proxy when the business is asset-light with little interest, depreciation, or amortization.
- Confirm by lining up the last reported quarter's EBITDA, free cash flow, and GAAP earnings — if they're within a few million of each other, EBITDA is a fair stand-in for owner earnings.
- Watch for the gap re-opening after an acquisition (new amortization), and adjust.
Here: EVER's last quarter showed free cash flow, adjusted EBITDA, and GAAP "very similar" — so its 3.7× EBITDA is genuinely 3.7× cash flow, not an EBITDA mirage.
Watch for
- Asset-light models where EBITDA, FCF, and GAAP converge; a post-deal amortization gap that breaks the equivalence.
10. The multi-year breakout from a tight range (David Hay's chart screen)
The repeatable method
- Screen for stocks emerging from a long, tight trading range into a multi-year breakout — the "dream scenario," strongest when paired with a clear improving fundamental story.
- Require the fundamental driver to explain the breakout (e.g. assets/revenue growing fast against a fixed cost base, so margins expand) — chart + story together, not chart alone.
- Systematize it: scan for names making multi-year new highs, then hand the shortlist to a sector specialist to pick the ones with the best fundamentals.
Here: Hay opens on SII (Sprott) "coming alive" out of a tight 2023–24 range as its assets grew drastically (hugely accretive to margins); he's now building a ~280-name Bloomberg breakout screen to hand the financials to Sy.
Watch for
- Tight multi-year bases breaking out with a margin-expansion story underneath; new-multi-year-high scans filtered by a domain specialist.