Operator-turned-investor with hands-on experience scaling high-growth technology and consumer businesses and a focus on early-stage venture investing and strategic board engagement. Kaitlin Theobald combines operating leadership in product and go-to-market with portfolio construction and founder support, advising on scaling, hiring, and capital strategy. Active in seed and Series A rounds and known for operational diligence and cross-functional execution.
Operator-turned-investor with hands-on experience scaling high-growth technology and consumer businesses and a focus on early-stage venture investing and strategic board engagement. Kaitlin Theobald combines operating leadership in product and go-to-market with portfolio construction and founder support, advising on scaling, hiring, and capital strategy. Active in seed and Series A rounds and known for operational diligence and cross-functional execution.
Operator-led investor approach prioritizing early-stage technology and consumer startups with strong product-market fit and repeatable go-to-market paths. Capital allocation favors seed and Series A rounds where operational value-add—particularly in product, hiring, and GTM execution—can accelerate scaling. Portfolio construction balances high-conviction, concentrated bets with follow-on reserves; underwriting emphasizes founder quality, unit-economics early signals, and defensible distribution. Time horizon is growth-focused with active board engagement and hands-on operational diligence to de-risk execution.
Operator-led investor approach prioritizing early-stage technology and consumer startups with strong product-market fit and repeatable go-to-market paths. Capital allocation favors seed and Series A rounds where operational value-add—particularly in product, hiring, and GTM execution—can accelerate scaling. Portfolio construction balances high-conviction, concentrated bets with follow-on reserves; underwriting emphasizes founder quality, unit-economics early signals, and defensible distribution. Time horizon is growth-focused with active board engagement and hands-on operational diligence to de-risk execution.
| Trades 83 | Longs Won 60/83 72% | Profit Factor 62.71 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $2.29M |
| Average Win $603,752.43 | Best Trade (Jun 02) $19.4M | Sharpe Ratio -12.86 |
| Average Loss -$25,115.12 | Worst Trade (May 19) -$775,037.9 | Z-Score 1.45 (85.32%) |
| Commissions $0 | Avg. Trade Length 1y 1m 3w 2d | Expectancy $429,487.93 |
| 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% | 0.13% | 4.34% |
| Consecutive Losing Trades | 7,299 | 6,569 | 5,839 | 5,109 | 4,380 | 3,650 | 2,920 | 2,190 | 1,460 | 730 |