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 62/83 74% | Profit Factor 58.33 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $2.38M |
| Average Win $622,437.17 | Best Trade (Jul 16) $19.03M | Sharpe Ratio -11.46 |
| Average Loss -$31,506.37 | Worst Trade (Jul 13) -$680,429.75 | Z-Score 2.68 (99.26%) |
| Commissions $0 | Avg. Trade Length 1y 2m 2w 5d | Expectancy $456,981.58 |
| 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% | 4.3% |
| Consecutive Losing Trades | 5,882 | 5,294 | 4,706 | 4,118 | 3,529 | 2,941 | 2,353 | 1,765 | 1,176 | 588 |