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 402/704 57% | Profit Factor 6.54 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $2.08M |
| Average Win $467,975.63 | Best Trade (Sep 29) $37.54M | Sharpe Ratio -0.67 |
| Average Loss -$95,188.62 | Worst Trade (Sep 29) -$5.35M | Z-Score -1.26 (79.47%) |
| Commissions $0 | Avg. Trade Length 5m 3w 4d | Expectancy $226,390.97 |
| Loss Size | 100% | 90% | 80% | 70% | 60% | 50% | 40% | 30% | 20% | 10% |
| Probability of Loss | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | 0.01% | 0.38% | 7.23% |
| Consecutive Losing Trades | 2,506 | 2,256 | 2,005 | 1,754 | 1,504 | 1,253 | 1,003 | 752 | 501 | 251 |
| Symbol | Quantity | Cost | Value | Comm. | Profit ($) | Gain (%) | Change |
|---|---|---|---|---|---|---|---|
AAPL Apple Inc. | 22,853 | $5.81M | $7.82M | - | $2.01M | 34.63% | -0.28% |
ALL Allstate Corporation | 929 | $221,046 | $222,560.53 | - | $1,514.53 | 0.69% | +1.44% |
AMZN Amazon.com Inc | 4,755 | $1.04M | $1.21M | - | $171,802.79 | 16.53% | +0.268% |
APD Air Products and Chemicals, Inc. | 876 | $254,469.61 | $259,585.08 | - | $5,115.47 | 2.01% | +1.299% |
AUR Aurora Innovation, Inc. | 12,407 | $47,642.88 | $66,997.8 | - | $19,354.92 | 40.62% | +6.931% |
AVDV Avantis International Small Cap Value ETF | 14,529 | $1.46M | $1.56M | - | $98,990.68 | 6.78% | 0.0 |
AVGO Broadcom Inc. | 1,151 | $377,773.61 | $396,323.83 | - | $18,550.22 | 4.91% | -0.555% |
BIL SPDR Bloomberg 1-3 Month T-Bill ETF | 3,429 | $314,234 | $313,856.37 | - | -$377.63 | -0.12% | +0.016% |
BILS SPDR Bloomberg 3-12 Month T-Bill ETF | 6,395 | $634,511.9 | $634,352.02 | - | -$159.88 | -0.03% | +0.02% |
BINC iShares Flexible Income Active ETF | 109,961 | $5.82M | $5.57M | - | -$251,245.47 | -4.31% | +0.109% |
BRK-B Berkshire Hathaway Inc. | 3,851 | $1.88M | $2.03M | - | $141,522.99 | 7.51% | -0.08% |
BX Blackstone Inc. | 4,498 | $615,818.22 | $491,496.46 | - | -$124,321.76 | -20.19% | +2.881% |
CACI Caci International Inc. | 2,564 | $1.38M | $1.57M | - | $184,696.1 | 13.36% | +1.162% |
CCJ Cameco Corporation | 4,079 | $442,675.86 | $339,637.93 | - | -$103,037.93 | -23.28% | +2.203% |
CME CME Group Inc. | 1,702 | $498,139.64 | $492,660.92 | - | -$5,478.72 | -1.1% | +1.355% |
COST Costco Wholesale Corporation | 230 | $229,179 | $224,914.7 | - | -$4,264.3 | -1.86% | -0.419% |
COWZ Pacer US Cash Cows 100 ETF | 110,026 | $6.64M | $7.74M | - | $1.1M | 16.6% | +1.428% |
CQP Cheniere Energy Partners L.P. | 4,347 | $280,946.89 | $270,318.19 | - | -$10,628.7 | -3.78% | -0.12% |
CRH CRH plc | 6,815 | $716,392.73 | $560,922.2 | - | -$155,470.53 | -21.7% | +3.923% |
CVX Chevron Corporation | 7,476 | $1.24M | $1.64M | - | $395,813.53 | 31.81% | -1.191% |