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:
50.35%
Gain -1.43%
Monthly
1.28%
Yearly
16.51%
Drawdown
17.81%
$228.21M
Equity
Holdings
$228.21M
Investment
$194.2M
$57.5M
Profit -$2.5M
Realized
$23.49M
Unrealized
$34.01M
Dividends
$15.36M
Goals
Avg. 77.5% completed goals
Yearly
Gain > 5% 2026
Yearly
Gain < 20% 2026
Today
Compared To Yesterday
Gain
-1.43%
Profit
-$2.5M
Win %
66%
This Week
Compared To Last Week
Gain
-0.3%
Profit
-$692,946.87
Win %
66%
This Month
Compared to last month
Gain
-1.08%
Profit
-$2.5M
Win %
66%
This Year
Compared to last year
Gain
2.74%
Profit
$6.09M
Win %
67%
AMZN Amazon.com Inc
+15.32%
+$1.62M 
GOOGL Alphabet Inc
+6.73%
+$681,088.17 
META Meta Platforms Inc Class A
+3.28%
+$255,210.67 
CRWD CrowdStrike Holdings, Inc.
+3.04%
+$113,724.96 
MSFT Microsoft Corp.
+3.02%
+$376,946.84 
NVDA NVIDIA Corporation
+2.93%
+$329,730.06 
MRVL Marvell Technology, Inc.
+2.32%
+$39,038.64 
GLW Corning Incorporated
+2.24%
+$49,949.55 
JCI Johnson Controls International plc
+1.93%
+$48,638.88 
SCHG Schwab U.S. Large-Cap Growth ETF
+1.12%
+$8,746.08 
IBM International Business Machines Corporation
+0.86%
+$18,691.06 
GEV GE Vernova Inc.
+0.85%
+$50,591.28 
TSLA Tesla, Inc.
+0.76%
+$8,184.41 
SPY SPDR S&P 500 ETF Trust
+0.72%
+$3,524.42 
VOO Vanguard S&P 500 ETF
+0.71%
+$2,726.48 
CAT Caterpillar Inc.
+0.7%
+$2,046.87 
QQQI Neos NASDAQ-100 High Income ETF
+0.68%
+$16,339.37 
PLTR Palantir Technologies Inc.
+0.65%
+$53,257.47 
SCHB Schwab U.S. Broad Market ETF
+0.59%
+$2,112.76 
APH Amphenol Corporation
+0.55%
+$23,689.33 
OHI Omega Healthcare Investors Inc.
+0.46%
+$46,549.93 
RKLB Rocket Lab Corporation
+0.42%
+$947.97 
AVGO Broadcom Inc.
+0.37%
+$1,516.32 
JEPI JPMorgan Equity Premium Income Fund
+0.33%
+$107,807.9 
SMH VanEck Semiconductor ETF
+0.3%
+$15,027.06 
JPM JPMorgan Chase & Co.
+0.27%
+$14,319.96 
WMT Walmart Inc.
+0.09%
+$1,806.44 
SCYB Schwab High Yield Bond ETF
+0.08%
+$12,771.84 
SPHY SPDR Portfolio High Yield Bond ETF
+0.04%
+$16,433.74 
SGOV iShares 0-3 Month Treasury Bond ETF
+0.02%
+$753.82 
AAPL Apple Inc.
-7.35%
-$86,604.64 
MU Micron Technology, Inc.
-5.9%
-$168,158.72 
SHOP Shopify Inc.
-4.29%
-$55,965 
ACHR Archer Aviation Inc.
-2.11%
-$1,422 
NET Cloudflare Inc.
-1.56%
-$17,604.72 
INTC Intel Corporation
-1.02%
-$4,041.78 
HUM Humana Inc.
-0.76%
-$1,668.81 
WEC WEC Energy Group Inc.
-0.57%
-$2,308.96 
VGT Vanguard Information Technology ETF
-0.38%
-$877.2 
COST Costco Wholesale Corporation
-0.24%
-$1,142.26 
SPSB SPDR Portfolio Short Term Corporate Bond ETF
-0.07%
-$2,953.4 
HOOD Robinhood Markets, Inc.
-0.05%
-$150.68 Events
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Dividends
Dividend Analysis
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| Trades 325 | Longs Won 229/325 70% | Profit Factor 7.35 |
| Profitability | Shorts Won 0/0 0% | Standard Deviation $616,984.02 |
| Average Win $290,664.91 | Best Trade (Sep 01) $5.74M | Sharpe Ratio -11.39 |
| Average Loss -$94,369.96 | Worst Trade (Aug 19) -$1.19M | Z-Score 0.96 (66.46%) |
| Commissions $0 | Avg. Trade Length 1y 3w 3d | Expectancy $176,931.53 |
| Loss Size | 100% | 90% | 80% | 70% | 60% | 50% | 40% | 30% | 20% | 10% |
| Probability of Loss | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% | <0.01% |
| Consecutive Losing Trades | 2,415 | 2,174 | 1,932 | 1,691 | 1,449 | 1,208 | 966 | 725 | 483 | 242 |
Hover over the desired column for a detailed explanation.
Returns
Overall, Monthly| Symbol | Quantity | Cost | Value | Comm. | Profit ($) | Gain (%) | Change |
|---|---|---|---|---|---|---|---|
| AAPL Apple Inc. | 3,532 | $786,560.61 | $1.09M | - | $304,509.51 | 38.71% | -7.354% |
| ACHR Archer Aviation Inc. | 14,220 | $67,261 | $65,980.8 | - | -$1,280.2 | -1.9% | -2.11% |
| AMZN Amazon.com Inc | 44,808 | $7.39M | $12.17M | - | $4.78M | 64.59% | +15.321% |
| APH Amphenol Corporation | 53,840 | $3.93M | $4.33M | - | $393,520.9 | 10.01% | +0.551% |
| AVGO Broadcom Inc. | 1,053 | $364,728.15 | $409,911.84 | - | $45,183.69 | 12.39% | +0.371% |
| CAT Caterpillar Inc. | 361 | $172,761.79 | $294,146.41 | - | $121,384.62 | 70.26% | +0.701% |
| COST Costco Wholesale Corporation | 501 | $339,850.21 | $476,896.9 | - | $137,046.69 | 40.33% | -0.239% |
| CRWD CrowdStrike Holdings, Inc. | 20,164 | $2.53M | $3.85M | - | $1.32M | 52.04% | +3.045% |
| GEV GE Vernova Inc. | 6,088 | $5.66M | $6.03M | - | $364,307.22 | 6.43% | +0.846% |
| GLW Corning Incorporated | 16,485 | $3.28M | $2.28M | - | -$998,012.66 | -30.45% | +2.241% |
| GOOGL Alphabet Inc | 30,311 | $4.48M | $10.79M | - | $6.31M | 140.92% | +6.734% |
| HOOD Robinhood Markets, Inc. | 3,767 | $368,231.7 | $326,071.52 | - | -$42,160.18 | -11.45% | -0.046% |
| HUM Humana Inc. | 596 | $236,743 | $216,860.55 | - | -$19,882.45 | -8.4% | -0.764% |
| IBM International Business Machines Corporation | 9,786 | $2.83M | $2.19M | - | -$645,323.74 | -22.77% | +0.861% |
| INTC Intel Corporation | 4,346 | $606,833 | $392,009.2 | - | -$214,823.8 | -35.4% | -1.021% |
| JCI Johnson Controls International plc | 17,496 | $2.31M | $2.57M | - | $258,381.76 | 11.2% | +1.932% |
| JEPI JPMorgan Equity Premium Income Fund | 567,410 | $32.49M | $32.59M | - | $94,673.34 | 0.29% | +0.332% |
| JPM JPMorgan Chase & Co. | 15,234 | $4.18M | $5.36M | - | $1.18M | 28.08% | +0.268% |
| META Meta Platforms Inc Class A | 14,435 | $9.05M | $8.04M | - | -$1.01M | -11.2% | +3.28% |
| MRVL Marvell Technology, Inc. | 9,164 | $2.73M | $1.72M | - | -$1.01M | -37.04% | +2.324% |
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FAQ
Which stocks have generated the highest profits for Troy Leonard?
The largest contributions to the portfolio's profits come from the following stocks: SPDR Portfolio High Yield Bond ETF - $6.02M, NVIDIA Corporation - $5.02M, VanEck Semiconductor ETF - $4.01M, JPMorgan Equity Premium Income Fund - $3.64M, and Palantir Technologies Inc - $2.67M. These positions have been the main drivers of growth and have significantly impacted the investor's overall performance.
Which stocks have generated the largest losses for this investor?
The largest losses in the portfolio are associated with the following stocks: The Kraft Heinz Company - $323,855.71, Robinhood Markets, Inc - $222,489.82, Visa Inc. Class A - $135,628.11, Oracle Corporation - $124,918.99, and Fortinet Inc - $79,764.12. These positions have had the most negative impact on overall performance and highlight the weaker areas of the portfolio.
What dividends does Troy Leonard's portfolio generate?
The portfolio generates substantial dividend income, with a total of $15.36M earned over time. The largest contributors to dividend income include SPDR Portfolio High Yield Bond ETF - $5.99M, JPMorgan Equity Premium Income Fund - $3.65M, iShares 0-3 Month Treasury Bond ETF - $2.05M, Omega Healthcare Investors Inc - $894,331.25, and Schwab High Yield Bond ETF - $649,608.13. This indicates that dividends play a meaningful role in the investor's overall strategy.
How stable are Troy Leonard's monthly returns?
Troy Leonard's monthly returns show a mixed pattern. Some months are relatively calm, while others are noticeably stronger or weaker, which suggests that performance is not fully consistent over time. This points to a strategy that may offer attractive upside but can also experience uneven short-term results.
Can Troy Leonard's strategy be considered aggressive or moderate?
Troy Leonard's strategy leans toward a moderately conservative profile. While there is still some exposure to market fluctuations, the overall structure and risk levels suggest a focus on maintaining stability rather than pursuing aggressive growth.
Should beginners follow Troy Leonard's strategy?
Troy Leonard's strategy may be suitable for beginners, but with some caution. While the overall approach is not overly complex, it still involves a certain level of risk and variability. Beginners should be prepared for occasional fluctuations and ensure they understand the strategy before trying to follow it.
