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 609 | Longs Won 247/609 40% | Profit Factor 6.77 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $1.25M |
| Average Win $369,655.82 | Best Trade (Sep 30) $22.27M | Sharpe Ratio -0.42 |
| Average Loss -$37,272.91 | Worst Trade (Mar 31) -$2.55M | Z-Score -5.31 (100%) |
| Commissions $0 | Avg. Trade Length 5m 3d | Expectancy $127,770.43 |
| 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% | 0.03% | 2.11% |
| Consecutive Losing Trades | 6,024 | 5,422 | 4,819 | 4,217 | 3,614 | 3,012 | 2,410 | 1,807 | 1,205 | 602 |