Why VCs Should Care About the ‘Cherrypick’ Mindset: How Technical Precision Impacts Startup Valuation
October 1, 2025PropTech’s ‘Cherrypick’ Moment: How Rare Finds Like the 1937 Washington Quarter DDO Are Inspiring Smarter Real Estate Software
October 1, 2025Milliseconds matter in high-frequency trading. I’ve spent years chasing those tiny advantages that separate profitable algos from the rest. Turns out, the hunt for market edges shares surprising DNA with another niche pursuit: finding rare coins like the 1937 Washington Quarter DDO (FS-101).
My job as a quant? Find, model, and profit from market quirks. Sound familiar? It’s exactly what expert coin collectors do – spotting treasures hiding in plain sight. Let’s explore how their methods can sharpen your algorithmic trading edge, especially for high-frequency trading (HFT), financial modeling, and backtesting trading strategies.
The Anatomy of a “Cherrypick” in Quantitative Finance
No coin collector stumbles onto a die-doubled 1937 quarter by accident. They use a highly refined visual inspection protocol – magnification, specific lighting, comparing against known variations. In our world? That’s anomaly detection.
Anomaly Detection: Spotting the Double Die in the Data
The DDO error on that Washington quarter? Pure anomaly. In trading, anomalies aren’t bugs. They’re inefficiencies in price formation, order flow, or liquidity supply waiting to be exploited.
Think of it like this:
- <
- A sudden order book imbalance that persists longer than expected
- A latency glitch creating fleeting arbitrage between venues
- A mispricing in futures vs. spot prices after unexpected news hits
<
Just like collectors check “IN GOD WE TRUST” for doubling, we use real-time data streams, statistical models, and machine learning classifiers to find these micro-opportunities before others do.
Backtesting as Your “Grading Submission”
You found a rare coin. Now what? You send it to PCGS for authentication and grading. In trading, that’s backtesting – putting your strategy through the wringer with historical data.
But here’s where many quants trip up: overfitting. They craft algorithms that work perfectly on past data but fail live. It’s like assuming a coin’s mint-state without professional verification.
Smart backtesting means:
- Using walk-forward analysis to simulate real-world conditions
- Running Monte Carlo simulations to stress-test against rare events
- Factoring in transaction costs and slippage (because a coin’s grade impacts its value, just like fees impact P&L)
Here’s a simple mean-reversion backtest using Backtrader:
import backtrader as bt
import pandas as pd
class MeanReversionStrategy(bt.Strategy):
params = (
('period', 20),
('devfactor', 2.0)
)
def __init__(self):
self.sma = bt.indicators.SimpleMovingAverage(self.datas[0].close, period=self.params.period)
self.upper = self.sma + self.params.devfactor * bt.indicators.StandardDeviation(self.datas[0].close, period=self.params.period)
self.lower = self.sma - self.params.devfactor * bt.indicators.StandardDeviation(self.datas[0].close, period=self.params.period)
def next(self):
if not self.position:
if self.datas[0].close[0] < self.lower[0]:
self.buy()
else:
if self.datas[0].close[0] > self.sma[0]:
self.sell()
# Load data and run backtest
cerebro = bt.Cerebro()
data = bt.feeds.YahooFinanceData(dataname='AAPL', fromdate=datetime(2020, 1, 1), todate=datetime(2023, 1, 1))
cerebro.adddata(data)
cerebro.addstrategy(MeanReversionStrategy)
results = cerebro.run()This is your grading process. It separates the real opportunities from the false positives – just like PCGS separates genuine rarities from damaged coins.
High-Frequency Trading: The Coin Show Floor
Imagine a bustling coin show. Dealers, collectors, and curious bystanders all trading information and assets. That’s a microsecond-level HFT environment – order books replace trays, APIs replace handshakes.
Latency, Speed, and the “Second Pass” Strategy
That rare coin wasn’t found on the first walkthrough. It took a second, more careful pass through the room. Why? The first pass was too rushed, too chaotic. Same with HFT.
The first wave of execution belongs to the speed demons. But delayed inefficiencies often emerge after the initial frenzy. That’s where adaptive latency arbitrage shines:
- Monitor low-latency feeds (Nasdaq TotalView, IEX Pillar) for early signals
- Use predictive models to anticipate larger follow-on orders
- Build medium-frequency strategies (100ms–1s) that target slower market participants
Like the collector who revisits a table, the best quants build systems that re-evaluate market state after the initial chaos. That’s where the edge lives.
Building a “Rarity Scoring” Model in Python
Coin collectors use visual heuristics and die markers to judge rarity. We can create a statistical rarity index for trades.
Score opportunities based on:
- Deviation from 52-week average volume
- Skew in implied volatility surface
- Order book depth asymmetry
- News sentiment spikes (information leakage)
def calculate_rarity_score(order_imbalance, volume_zscore, volatility_skew, news_sentiment):
# Normalize and weight features
return (
0.4 * volume_zscore +
0.3 * abs(order_imbalance) +
0.2 * volatility_skew +
0.1 * news_sentiment
)
# Example: only trade when score > 2.0
if calculate_rarity_score(imb, vol_z, skew, sent) > 2.0:
execute_opportunistic_trade()Financial Modeling: From Die Varieties to Market Regimes
Die varieties like the 1937 DDO are microstructures within a broader minting system. Markets work the same way – microstructures within macro regimes. Smart quants don’t just run one strategy. They adapt, like collectors who know 1946 Franklins from 1961s.
Regime Detection with Machine Learning
Use Hidden Markov Models (HMM) or k-means clustering to identify market states:
- High volatility, low volume (like a rare coin market)
- Low volatility, high volume (bull market conditions)
- Asymmetric information (when a dealer misses a key detail)
Train models to switch strategies based on regime – just like collectors adjust their targets based on what’s available.
Portfolio of Niche Strategies
No single coin dominates. Same with trading. Build a portfolio of niche strategies:
- Statistical arbitrage for mean-reverting assets
- Event-driven trading for news anomalies
- Order flow prediction for HFT opportunities
- Liquidity provision in stable markets
Each is like a “rare coin” – valuable when market conditions align.
Python for Finance: The Loupe of the Modern Quant
Coin collectors use loupes. We use Python, pandas, NumPy, and QuantConnect to zoom in on data patterns.
Key Tools for the Cherrypicking Quant
- pandas: Clean and merge tick data (like inspecting a coin from multiple angles)
- NumPy: Fast numerical analysis of price deviations
- Plotly/Matplotlib: Visualize order book depth (like a TrueView image)
- PyAlgoTrade/Zipline: Event-driven backtesting
- TensorFlow/PyTorch: Anomaly detection and regime classification
Example: Spotting volume spikes with pandas:
import pandas as pd
# Load tick data
df = pd.read_csv('market_data.csv', parse_dates=['timestamp'])
df['volume_zscore'] = (df['volume'] - df['volume'].rolling(100).mean()) / df['volume'].rolling(100).std()
# Flag anomalies
anomalies = df[df['volume_zscore'] > 3]Conclusion: The Quant as a Financial Cherrypicker
The 1937 Washington Quarter DDO story isn’t just about coins. It’s a blueprint for modern quant trading. The principles are identical:
“Real finds come from systematic inspection, patience, and having the nerve to act when others overlook the details.”
Your edge comes from:
- Detecting anomalies others miss (die doubling or order flow skew)
- Validating findings through rigorous backtesting (like PCGS grading)
- Adapting strategies to regime shifts (like targeting different coin types)
- Building niche portfolios of high-conviction trades
- Leveraging Python to automate inspection at scale
In HFT, speed gets you in the game. But real profits come from the second pass – when you re-evaluate, re-analyze, and re-position. That’s where the real “cherrypicks” are found.
Next time you’re scanning the market, ask yourself: Am I just trading, or am I cherrypicking?
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