Simplex Trading Portfolio holdings
Simplex Trading, founded in 2004 and headquartered in Chicago, Illinois, is a technology-driven proprietary trading firm specializing in market-making and liquidity provision, primarily in U.S. equity options and futures options. Leveraging advanced proprietary software and data-driven analysis, the firm optimizes trading strategies and develops innovative solutions to capitalize on financial market opportunities, maintaining a competitive edge through automation and a collaborative team of technologists and traders. With a workforce exceeding 300 and led by CEO Erik Swanson since 2014, Simplex operates with a low-ego, high-intelligence culture, focusing on minimal bureaucracy and rapid execution, while also making strategic venture capital investments in fintech startups. Recognized as a top workplace in Chicago by Built In’s 2025 awards, Simplex continues to evolve, blending cutting-edge technology with a commitment to market efficiency and growth.
Top Buys
| Rank | Stock | Value |
|---|---|---|
| 1 |
Microsoft
MSFT
|
+$53.9M |
| 2 |
iShares 20+ Year Treasury Bond ETF
TLT
|
+$52.9M |
| 3 |
NVIDIA
NVDA
|
+$47.1M |
| 4 |
PayPal
PYPL
|
+$41.7M |
| 5 |
Alphabet (Google) Class C
GOOG
|
+$28.4M |
Top Sells
| Rank | Stock | Value |
|---|---|---|
| 1 |
Apple
AAPL
|
+$51.4M |
| 2 |
Walmart Inc
WMT
|
+$46.4M |
| 3 |
VanEck Oil Services ETF
OIH
|
+$34.2M |
| 4 |
Adobe
ADBE
|
+$33.5M |
| 5 |
Starbucks
SBUX
|
+$26.8M |
Sector Composition
| Rank | Sector | Weight |
|---|---|---|
| 1 | Technology | 0.41% |
| 2 | Healthcare | 0.21% |
| 3 | Consumer Discretionary | 0.21% |
| 4 | Communication Services | 0.2% |
| 5 | Financials | 0.15% |
| Name | Market Value | Portfolio Weight | Shares or Principal |
Change in Stake | Capital Flow | |
|---|---|---|---|---|---|---|
251
CALL
PepsiCo
PEP
$185B
| $53.9M | 0.04% |
291,000
-135,600
| -32% | -$25.3M |
|
252
PUT
Humana
HUM
$48B
| $53.5M | 0.04% |
119,600
-55,900
| -32% | -$28.1M |
|
253
CALL
Zscaler
ZS
$23.3B
| $53.4M | 0.04% |
364,800
+52,800
| +17% | +$6.45M |
|
254
CALL
Charter Communications
CHTR
$15.7B
| $53.3M | 0.04% |
145,100
+36,200
| +33% | +$12.4M |
|
255
PUT
Capital One
COF
$124B
| $53M | 0.04% |
484,700
+42,900
| +10% | +$4.3M |
|
256
CALL
Dollar General
DG
$26.9B
| $52.8M | 0.04% |
311,200
+182,000
| +141% | +$36M |
|
257
PUT
ON Semiconductor
ON
$36.3B
| $52.8M | 0.04% |
558,500
-350,800
| -39% | -$29M |
|
258
CALL
Bristol-Myers Squibb
BMY
$125B
| $52.7M | 0.04% |
824,200
-130,400
| -14% | -$8.74M |
|
259
CALL
JD.com
JD
$40.8B
| $52.6M | 0.04% |
1,540,200
-1,021,200
| -40% | -$37.2M |
|
260
PUT
Merck
MRK
$317B
| $52.4M | 0.04% |
454,400
-357,700
| -44% | -$40.6M |
|
261
CALL
Twilio
TWLO
$28B
| $52M | 0.04% |
817,300
+126,900
| +18% | +$7.49M |
|
262
CALL
Analog Devices
ADI
$188B
| $51.9M | 0.04% |
266,200
+36,100
| +16% | +$6.69M |
|
263
PUT
DraftKings
DKNG
$11.4B
| $51.8M | 0.04% |
1,949,800
+40,600
| +2% | +$936K |
|
264
CALL
Wynn Resorts
WYNN
$9.85B
| $51.4M | 0.04% |
487,000
-422,300
| -46% | -$45.3M |
|
265
CALL
Datadog
DDOG
$88.3B
| $51.3M | 0.04% |
521,000
-96,200
| -16% | -$8.04M |
|
266
CALL
Ulta Beauty
ULTA
$20.8B
| $51.1M | 0.04% |
108,600
-1,500
| -1% | -$735K |
|
267
CALL
Proshares UltraShort Technology
REW
$3.27M
| $51.1M | 0.04% |
333,900
-46,888
| -12% | -$4.73M |
|
268
CALL
Lowe's Companies
LOW
$114B
| $50.7M | 0.04% |
224,600
-232,000
| -51% | -$48.3M |
|
269
PUT
Roku
ROKU
$21.3B
| $50.3M | 0.04% |
787,000
-470,200
| -37% | -$28.6M |
|
270
PUT
Unity
U
$12.7B
| $50.2M | 0.04% |
1,157,000
+446,100
| +63% | +$14.3M |
|
271
PUT
Apollo Global Management
APO
$68.8B
| $50.1M | 0.04% |
652,800
+296,100
| +83% | +$19.8M |
|
272
PUT
American Express
AXP
$238B
| $50M | 0.04% |
287,300
-169,400
| -37% | -$27.3M |
|
273
PUT
Crocs
CROX
$6.73B
| $49.7M | 0.04% |
442,000
+45,300
| +11% | +$5.4M |
|
274
PUT
Take-Two Interactive
TTWO
$43.3B
| $49.6M | 0.04% |
337,100
+82,600
| +32% | +$10.8M |
|
275
PUT
PNC Financial Services
PNC
$101B
| $49.6M | 0.04% |
393,700
+121,300
| +45% | +$14.8M |
|
Similar funds
Simplex Trading's Q2 2023 Portfolio in Review
As of Q2 2023, Simplex Trading held 10,535 positions worth $122B, up 6.9% from $114B the previous quarter. Its ten largest holdings account for 43% of the portfolio.
Simplex Trading's Q2 2023 filing shows 1,474 new, 3,350 increased, 3,913 reduced and 1,517 closed positions. Its largest new stake was Microsoft: 171,935 shares worth $58.5M. The largest sale was Apple, an estimated $51.4M.
By sector, the portfolio is most concentrated in Technology at 0.41% of assets, down from 0.42% a quarter earlier, followed by Healthcare and Consumer Discretionary.
- Simplex Trading's largest Q2 2023 buy was Microsoft: 171,935 shares worth $58.5M.
- Simplex Trading added most to iShares 20+ Year Treasury Bond ETF in Q2 2023, an estimated $52.9M increase.
- Simplex Trading's biggest Q2 2023 reduction was Adobe, cutting an estimated $33.5M.
- Simplex Trading fully exited Apple in Q2 2023, selling an estimated $51.4M.
- Simplex Trading's ten largest holdings make up 43% of its $122B portfolio in Q2 2023.
- Simplex Trading opened 1,474 new positions and closed 1,517 in Q2 2023.
- Simplex Trading's portfolio value rose 6.9% quarter-over-quarter to $122B.
Based on Simplex Trading's 13F filing for Q2 2023, filed 4 Aug 2023.