Strategic investor and operating executive focused on growth-stage technology and fintech businesses, with experience in scaling product, go-to-market and finance teams across VC-backed companies. Matthew Chester brings sector specialization in SaaS monetization, capital raises and board-level governance, and is often engaged as an investor or independent director.
Strategic investor and operating executive focused on growth-stage technology and fintech businesses, with experience in scaling product, go-to-market and finance teams across VC-backed companies. Matthew Chester brings sector specialization in SaaS monetization, capital raises and board-level governance, and is often engaged as an investor or independent director.
Focuses on growth-stage technology and fintech businesses, prioritizing companies with clear SaaS monetization paths, strong unit economics and repeatable go-to-market motion. Deploys capital with an operator-investor mindset, blending catalytic seed/Series A/B checks with board-level governance and hands-on scaling of product, sales and finance functions. Prefers revenue-generating teams with defensible metrics and follow-on financing optionality. Investment horizon is medium-to-long, risk-managed through milestones, staged capital and active board oversight to drive exits or strategic partnerships.
Focuses on growth-stage technology and fintech businesses, prioritizing companies with clear SaaS monetization paths, strong unit economics and repeatable go-to-market motion. Deploys capital with an operator-investor mindset, blending catalytic seed/Series A/B checks with board-level governance and hands-on scaling of product, sales and finance functions. Prefers revenue-generating teams with defensible metrics and follow-on financing optionality. Investment horizon is medium-to-long, risk-managed through milestones, staged capital and active board oversight to drive exits or strategic partnerships.
| Trades 704 | Longs Won 419/704 59% | Profit Factor 6.82 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $2.08M |
| Average Win $451,848.51 | Best Trade (Sep 29) $37.54M | Sharpe Ratio -0.67 |
| Average Loss -$97,394.3 | Worst Trade (Sep 29) -$5.35M | Z-Score -2.02 (99.01%) |
| Commissions $0 | Avg. Trade Length 5m 1w 6d | Expectancy $229,498.79 |
| Loss Size | 100% | 90% | 80% | 70% | 60% | 50% | 40% | 30% | 20% | 10% |
| Probability of Loss | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | 0.01% | 0.34% | 6.81% |
| Consecutive Losing Trades | 2,475 | 2,228 | 1,980 | 1,733 | 1,485 | 1,238 | 990 | 743 | 495 | 248 |
| Symbol | Quantity | Cost | Value | Comm. | Profit ($) | Gain (%) | Change |
|---|---|---|---|---|---|---|---|
AAPL Apple Inc. | 22,853 | $5.81M | $7.16M | - | $1.36M | 23.34% | +0.294% |
ALL Allstate Corporation | 929 | $221,046 | $247,987.26 | - | $26,941.26 | 12.19% | -2.97% |
AMZN Amazon.com Inc | 4,755 | $1.04M | $1.3M | - | $265,381.19 | 25.53% | +0.801% |
APD Air Products and Chemicals, Inc. | 876 | $254,469.61 | $265,830.95 | - | $11,361.34 | 4.46% | +1.18% |
AUR Aurora Innovation, Inc. | 12,407 | $47,642.88 | $87,531.38 | - | $39,888.5 | 83.72% | +4.056% |
AVDV Avantis International Small Cap Value ETF | 14,529 | $1.46M | $1.59M | - | $132,699.41 | 9.09% | +1.313% |
AVGO Broadcom Inc. | 1,151 | $377,773.61 | $492,081.26 | - | $114,307.65 | 30.26% | +1.654% |
BIL SPDR Bloomberg 1-3 Month T-Bill ETF | 3,429 | $314,234 | $313,650.63 | - | -$583.37 | -0.19% | +0.022% |
BILS SPDR Bloomberg 3-12 Month T-Bill ETF | 6,395 | $634,511.9 | $634,511.9 | - | - | - | +0.04% |
BINC iShares Flexible Income Active ETF | 109,961 | $5.82M | $5.72M | - | -$101,148.81 | -1.74% | +0.173% |
BRK-B Berkshire Hathaway Inc. | 3,851 | $1.88M | $2.01M | - | $125,618.36 | 6.67% | -0.536% |
BX Blackstone Inc. | 4,498 | $615,818.22 | $616,720.78 | - | $902.56 | 0.15% | +2.743% |
CACI Caci International Inc. | 2,564 | $1.38M | $1.65M | - | $270,795.19 | 19.59% | +2.516% |
CCJ Cameco Corporation | 4,079 | $442,675.86 | $397,253.81 | - | -$45,422.05 | -10.26% | +4.027% |
CME CME Group Inc. | 1,702 | $498,139.64 | $448,698.26 | - | -$49,441.38 | -9.93% | -0.261% |
COST Costco Wholesale Corporation | 230 | $229,179 | $217,991.7 | - | -$11,187.3 | -4.88% | -0.143% |
COWZ Pacer US Cash Cows 100 ETF | 110,026 | $6.64M | $7.62M | - | $981,576.63 | 14.79% | +1.629% |
CQP Cheniere Energy Partners L.P. | 4,347 | $280,946.89 | $281,902.95 | - | $956.06 | 0.34% | -1.802% |
CRH CRH plc | 6,815 | $716,392.73 | $684,771.2 | - | -$31,621.53 | -4.41% | +2.888% |
CVX Chevron Corporation | 7,476 | $1.24M | $1.39M | - | $150,264.31 | 12.08% | -1.416% |