Shadow Edge — One-Page Summary — Nicholas Levenstein & Company
Nicholas Levenstein & Company
Shadow Edge — Prediction-Market Strategy
Options-implied fair value · daily Bitcoin and Ether contracts · fully automated · validation pilot, deliberately small
One-Page SummaryAs of August 26, 2026
60 s
Decision cycle · every daily BTC/ETH contract re-priced against the options chain once a minute
62%
Resolved automated positions won · 25 of 40 · 20 Jul – 26 Aug 2026
−$7
Net result of the automated pilot on $176 deployed · a validation cost, not a track record
0
Sell orders ever placed by the automated system · every exit has been a resolution · the biggest fix ahead

The Idea ↑ top

Polymarket's daily "will Bitcoin be above $X" and "between $X and $Y" contracts are priced by a retail crowd. The listed options market on Deribit is priced by professionals, and its deltas, implied volatility and skew already say where those professionals think price will land. Shadow Edge reads the second market to price the first. It is poker where you can see the other professionals' hands.

The gap is real and it has now been measured independently: a June 2026 academic paper (arXiv 2606.19517) puts the average wedge between Polymarket and options-implied probability at 5.6–6.3 percentage points, decaying with a half-life of roughly four hours. That is the entire opportunity, and it says two things at once: the edge exists, and it belongs to whoever is fastest and most disciplined.

The thesis has held. The plumbing has not. Across every period we can measure, positions taken inside the specified price band have won far more often than they lost. The money that was lost went to fills the specification should have rejected, to mispriced inputs at the edge of an expiry, to a runaway retry loop, and to the absence of any exit path. Those are engineering problems, and engineering problems get fixed.

How It Works ↑ top

UniversePolymarket daily BTC and ETH price contracts resolving 16:00 UTC; range ("between") contracts only as of 25 Aug
Fair valueDeribit call deltas interpolated across the 08:00 UTC expiries to the 16:00 UTC resolution; the professionals' implied probability, on our clock
EntryAsk price 0.55–0.75; our probability ≥ 51%; net edge after fees ≥ 5 pp; one position per asset; $5 maximum ticket
ExitHold to resolution (current). Edge-captured take-profit and thesis-broken exits are specified but not yet live
HedgeNone since 12 Aug; Deribit contract minimums dwarf pilot tickets
StackPython runner on a dedicated server, Polymarket CLOB via proxy wallet, live positions published at levenstein.net/polymarketinfo
OversightDaily loss-analysis run at 07:00 Bali; daily sign-off call; independent verification of the trade ledger; Polymarket is the position record of truth

Honest History ↑ top

Mar – Apr 2026Manual trading from Nicholas's own wallet. 54 markets, 26 won / 28 lost, +$35. Proved the wedge exists; proved a human cannot watch it.
29 – 30 AprTwo manual losses (−$23 from a five-minute delay, −$68 from an unmonitored position). Decision: full automation.
19 MayFirst fills through the automated pipeline. Two positions, two wins.
25 JunWorst day. A sign inversion on a newly added feed bought four deep out-of-the-money contracts; the small account went to zero. Refunded to ~$40; hard price band written into the spec.
30 Jun – 8 Jul52 resolved trades, net −$1.69. The 16 in-band trades went 16 for 16 (+$26); the losses were all out-of-band fills the runner should have refused.
16 – 20 JulWallet rotation broke the signer / API-key pairing; 162 orders rejected. Fixed 20 Jul; current wallet funded.
28 Jul – 11 AugSixteen days of silence: the runner was not running. Then 190,795 decisions and zero approvals in a low-volatility regime.
12 AugRestart, unhedged, hold-to-resolution. Model reverted to v1 without sign-off.
17 – 24 AugOne-per-asset breaches; a 74-order retry storm into a Polymarket outage (19 Aug); wrong-expiry pricing (−$10, 20 Aug); near-expiry pricing off a dead endpoint; a kill order on "above" markets executed seven hours late (24 Aug).
25 – 26 AugRange-only in code; 60-second cadence confirmed; daily sign-off instituted; expiry-bracket formula v1.2 drafted.

Results ↑ top

On-chain wallet activity, not internal ledgers. Dollar figures are pilot-sized by design.

PeriodMarketsWon / LostDeployedNet
Manual · 24 Mar – 26 Apr5426 / 28$1,624+$34.86
Automated · 20 Jul – 26 Aug4025 / 15$176−$7.36
  of which range contracts, 12 – 23 Aug86 / 2+$3.65
  of which "above" contracts, 12 – 23 Aug126 / 6−$14.21
In-band cohort · 30 Jun – 8 Jul1616 / 0+$26.11
What the numbers say. The signal has been right more often than wrong. Average win +$2.31, average loss −$4.34: a binary contract loses the whole stake and wins only the complement, so a 62% hit rate at a 0.64 average price is roughly break-even before fees. To be profitable the system must either buy cheaper, exit early when the edge closes, or both. It has never yet done the second.

What Changes Next ↑ top

Every loss on this page has a name and a fix. The programme below takes the fixes in the order that removes the most risk soonest, and only then scales.

1 · Price it right
Expiry bracket and time floor

Formula v1.2: the two Deribit expiries must bracket the Polymarket close; no entries after 08:00 UTC; no entries inside the final 60–90 minutes; fall back to the far chain when the near one goes dead. This alone would have blocked the wrong-expiry losses of 20 Aug and every dead-endpoint fill of 23–24 Aug.

2 · Enforce the spec
The runner obeys the rulebook

Price band 0.55–0.75 enforced in code, the 0.85 confidence haircut actually wired, one position per asset read from the live wallet, a portfolio-level overlap check, and range-only until the "above" branch is explained line by line. The July in-band cohort went 16 for 16; this makes in-band the only kind of fill there is.

3 · Build the exit
The first sell order

Redemption write-back so the ledger reconciles to the chain; then edge-captured take-profit and thesis-broken exits go live. With a four-hour edge half-life, capturing 3–5 points early and recycling capital is worth more than any single resolution.

4 · Execution hygiene
No more retry storms

Attempt cap, exponential backoff, order de-duplication, automatic halt on venue errors, and a kill switch the runner itself observes, with a market-type filter. Nicholas's stop authority becomes a control, not a convention.

5 · Ship like a firm
Staging, signed deploys, daily sign-off

Staging server before production; every strategy change carries a commit hash and a signature; a one-tap daily approval on Nicholas's phone; independent ledger verification; regression tests R1–R5 run on every release. Silent reversions and seven-hour kill delays end here.

6 · Then scale
Thirty clean signals, then more capital and more markets

After 30 consecutive clean resolved signals, limits step from $5 to $25 per ticket and a $1,000 bankroll; after 100, the sleeve-fund bar. Solana dailies are built and waiting on staging; Kalshi oil and gold ladders and XRP weeklies follow. Directional inputs (funding, basis, skew drift) run in shadow mode first. The wedge is public now; speed, breadth and discipline are the moat.

Status & Structure ↑ top

StageValidation pilot; not open to investors
Capital at risk~$200 hot wallet; $1,000 bankroll planned ($200 hot / $800 reserve)
Ticket size$5 maximum, by design, until 30 clean signals
TeamNicholas Levenstein (principal); Aneep Tandel (engineering); independent ledger verification; external advisor
TransparencyPositions published live; every fill and every loss analysed daily
Fund statusSleeve-fund structure follows a 100-signal validated record and legal entity; no solicitation until then

Why We Publish This ↑ top

Most strategies show you the backtest. We are showing the pilot, including the day it went to zero, because the point of a validation phase is to find out what breaks before it matters. What broke was never the idea. Every one of the fixes above is specified, owned and dated, and the page will be updated as each goes live.

Related. CMFDH, the firm's hedged Bitcoin strategy since 2019, is summarised at levenstein.net/one-page-summary. Shadow Edge is the firm's technology argument; CMFDH is its track-record argument. They are kept separate on purpose.
Important information. Shadow Edge is a research and validation pilot of Nicholas Levenstein & Company. No return, yield, or performance claim is made or implied; the figures above describe a deliberately small live pilot and are not a track record, are not annualised, and are not indicative of future results. Figures derive from on-chain wallet activity and the firm's internal records as of August 26, 2026 and are not independently audited. Prediction-market contracts are binary instruments that can lose the entire amount staked; access to such venues is restricted in many jurisdictions and users are responsible for compliance with local law. This document is for information only and does not constitute an offer to sell or a solicitation of an offer to buy any security, fund interest, or investment product; Shadow Edge is not currently open to outside investors. Live positions: levenstein.net/polymarketinfo.
Nicholas Levenstein & Company · Est. 2019 nick@levenstein.net · levenstein.net Data as of August 26, 2026