Troy Leonard Portfolio
Invests via CORNERSTONE ENTERPRISES, LLC | Managed by Troy Leonard
Invests via CORNERSTONE ENTERPRISES, LLC
Managed by Troy Leonard
Automatically Tracked
Troy Leonard Profile
Venture-focused operator and early-stage investor with experience sourcing and scaling technology businesses across fintech, SaaS and marketplaces. Troy Leonard brings operational track record leading product and go-to-market teams, portfolio construction and hands-on board support for Series A–C companies. Known for connecting founders to commercial partners and follow-on capital, focuses on unit-economics-driven growth and pragmatic governance to de-risk scaling.
Venture-focused operator and early-stage investor with experience sourcing and scaling technology businesses across fintech, SaaS and marketplaces. Troy Leonard brings operational track record leading product and go-to-market teams, portfolio construction and hands-on board support for Series A–C companies. Known for connecting founders to commercial partners and follow-on capital, focuses on unit-economics-driven growth and pragmatic governance to de-risk scaling.
Investment Philosophy & Strategy
Operationally-minded early-stage investor emphasizing unit economics, repeatable go-to-market motion, and capital-efficient scaling. Prioritizes Series A–C fintech, SaaS and marketplace founders with product-market fit and measurable unit-level profitability. Employs hands-on board work, introductions to commercial partners and targeted follow-on allocations to de-risk growth. Portfolio construction favors concentrated, high-conviction positions and staged capital tied to operational milestones.
Operationally-minded early-stage investor emphasizing unit economics, repeatable go-to-market motion, and capital-efficient scaling. Prioritizes Series A–C fintech, SaaS and marketplace founders with product-market fit and measurable unit-level profitability. Employs hands-on board work, introductions to commercial partners and targeted follow-on allocations to de-risk growth. Portfolio construction favors concentrated, high-conviction positions and staged capital tied to operational milestones.
Disclaimer: This Portfolio is derived from and computed based on publicly available data from SEC filings.
Gain and growth charts are calculated per selected timeframe:
17.82%
Gain
Monthly
0.54%
Yearly
6.67%
Drawdown
25.9%
$218.81M
Equity
Holdings
$218.81M
Investment
$185.39M
$54.04M
Profit -$583,968.26
Realized
$20.62M
Unrealized
$33.42M
Dividends
$14.74M
Goals
Avg. 100% completed goals
Yearly
Gain > 5% 2026
Yearly
Gain < 20% 2026
Today
Compared To Yesterday
Gain
0%
Profit
-$583,968.26
Win %
69%
This Week
Compared To Last Week
Gain
-0.003%
Profit
-$6,886.88
Win %
69%
This Month
Compared to last month
Gain
1.2%
Profit
$2.59M
Win %
69%
This Year
Compared to last year
Gain
8.82%
Profit
$17.73M
Win %
69%
OHI Omega Healthcare Investors Inc.
+3.2%
+$364,214.05 
COST Costco Wholesale Corporation
+2.21%
+$10,039.04 
SHOP Shopify Inc.
+2.04%
+$25,416.72 
WMT Walmart Inc.
+1.88%
+$34,265.75 
IBM International Business Machines Corporation
+1.21%
+$51,742.25 
MSFT Microsoft Corp.
+1.11%
+$121,673.52 
AAPL Apple Inc.
+0.97%
+$10,619.5 
NET Cloudflare Inc.
+0.96%
+$10,956.84 
WEC WEC Energy Group Inc.
+0.66%
+$2,643 
AMZN Amazon.com Inc
+0.52%
+$63,662.28 
JEPI JPMorgan Equity Premium Income Fund
+0.38%
+$114,788.07 
GOOGL Alphabet Inc
+0.1%
+$11,349.01 
SGOV iShares 0-3 Month Treasury Bond ETF
0%
$0 
GLW Corning Incorporated
-10.1%
-$137,718 
HOOD Robinhood Markets, Inc.
-5.01%
-$122,190.77 
SMH VanEck Semiconductor ETF
-3.83%
-$215,283.76 
AVGO Broadcom Inc.
-3.58%
-$14,741.28 
CAT Caterpillar Inc.
-3.18%
-$10,497.88 
GEV GE Vernova Inc.
-2.82%
-$94,694.25 
NVDA NVIDIA Corporation
-2.77%
-$379,745.97 
APH Amphenol Corporation
-1.96%
-$50,173.2 
JCI Johnson Controls International plc
-1.73%
-$40,530.23 
META Meta Platforms Inc Class A
-1.52%
-$147,025.86 
TSLA Tesla, Inc.
-1.47%
-$31,067.5 
CRWD CrowdStrike Holdings, Inc.
-0.76%
-$45,194.32 
PLTR Palantir Technologies Inc.
-0.72%
-$62,732.16 
JPM JPMorgan Chase & Co.
-0.54%
-$22,252.46 
SCHG Schwab U.S. Large-Cap Growth ETF
-0.47%
-$3,894 
SPY SPDR S&P 500 ETF Trust
-0.38%
-$1,900.8 
VOO Vanguard S&P 500 ETF
-0.38%
-$1,500.81 
SCHB Schwab U.S. Broad Market ETF
-0.36%
-$1,304.73 
SCYB Schwab High Yield Bond ETF
-0.08%
-$12,517.3 
IGSB iShares 1-5 Year Investment Grade Corporate Bond ETF
-0.04%
-$1,320.7 
SPSB SPDR Portfolio Short Term Corporate Bond ETF
-0.02%
-$1,255.42 
SPHY SPDR Portfolio High Yield Bond ETF
-0.02%
-$8,269.53 Events
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Dividends
Dividend Analysis
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| Trades 285 | Longs Won 201/285 70% | Profit Factor 11.87 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $613,213.36 |
| Average Win $293,576.71 | Best Trade (Jul 15) $5.61M | Sharpe Ratio -11.45 |
| Average Loss -$59,181.26 | Worst Trade (Jul 16) -$880,471.61 | Z-Score 1 (68.37%) |
| Commissions $0 | Avg. Trade Length 1y 2w 3d | Expectancy $189,605.94 |
| 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% | <0.01% | <0.01% |
| Consecutive Losing Trades | 3,704 | 3,333 | 2,963 | 2,593 | 2,222 | 1,852 | 1,481 | 1,111 | 741 | 370 |
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Returns
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