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 | |
|---|---|---|---|---|---|---|
|
GREK
5201
Global X MSCI Greece ETF
GREK
$302M
| $90K | ﹤0.01% |
+2,438
| New | +$81.6K |
|
5202
CALL
Hilton Grand Vacations
HGV
$3.64B
| $90K | ﹤0.01% |
+2,000
| New | +$89.3K |
|
5203
CALL
Manitowoc
MTW
$497M
| $90K | ﹤0.01% |
4,800
-11,200
| -70% | -$181K |
|
|
OLO
5204
DELISTED
Olo Inc
OLO
| $90K | ﹤0.01% |
+14,026
| New | +$101K |
|
5205
PUT
Par Pacific Holdings
PARR
$4.31B
| $90K | ﹤0.01% |
3,400
-15,500
| -82% | -$366K |
|
5206
CALL
Prosperity Bancshares
PB
$8.97B
| $90K | ﹤0.01% |
1,600
-2,500
| -61% | -$149K |
|
|
RENT
5207
Rent the Runway
RENT
$119M
| $90K | ﹤0.01% |
2,287
-745
| -25% | -$36.7K |
|
|
SII
5208
CALL
Sprott
SII
$2.75B
| $90K | ﹤0.01% |
2,800
-6,900
| -71% | -$238K |
|
5209
SkinHealth Systems
SKIN
$87.6M
| $90K | ﹤0.01% |
10,821
-9,044
| -46% | -$94K |
|
5210
CALL
Smith Micro Software
SMSI
$13.9M
| $90K | ﹤0.01% |
2,038
+60
| +3% | +$2.85K |
|
|
SNCY
5211
DELISTED
Sun Country Airlines
SNCY
| $90K | ﹤0.01% |
+4,008
| New | +$76.5K |
|
5212
CALL
SS&C Technologies
SSNC
$18.6B
| $90K | ﹤0.01% |
1,500
-27,300
| -95% | -$1.55M |
|
5213
-1x Short VIX Futures ETF
SVIX
$169M
| $90K | ﹤0.01% |
+3,218
| New | +$67.4K |
|
5214
PUT
TaskUs
TASK
$542M
| $90K | ﹤0.01% |
8,000
-12,900
| -62% | -$157K |
|
5215
PUT
Telephone and Data Systems
TDS
$3.82B
| $90K | ﹤0.01% |
11,000
+8,300
| +307% | +$70.4K |
|
5216
PUT
Verra Mobility
VRRM
$781M
| $90K | ﹤0.01% |
4,600
-6,600
| -59% | -$117K |
|
|
QLTB
5217
PUT
DELISTED
ISHARES BAA BA RATED CORP BOND FUND
QLTB
| $90K | ﹤0.01% |
1,300
-21,200
| -94% | -$1.47M |
|
|
ACR
5218
PUT
ACRES Commercial Realty
ACR
$126M
| $89K | ﹤0.01% |
10,100
+9,000
| +818% | +$78.1K |
|
5219
PUT
Affiliated Managers Group
AMG
$9.65B
| $89K | ﹤0.01% |
+600
| New | +$85.9K |
|
|
OPTU
5220
Optimum Communications Inc
OPTU
$290M
| $89K | ﹤0.01% |
29,765
+28,673
| +2,626% | +$81.4K |
|
|
HDSN
5221
PUT
Hudson Technologies
HDSN
$244M
| $89K | ﹤0.01% |
9,300
-25,800
| -74% | -$224K |
|
|
PPLI
5222
People Inc
PPLI
$3.08B
| $89K | ﹤0.01% |
1,738
-18,461
| -91% | -$846K |
|
5223
PUT
ICU Medical
ICUI
$4.21B
| $89K | ﹤0.01% |
500
| – | – |
|
5224
CALL
Lexicon Pharmaceuticals
LXRX
$1.04B
| $89K | ﹤0.01% |
39,200
+23,400
| +148% | +$62.1K |
|
5225
CALL
PLAYSTUDIOS Inc
MYPS
$76.3M
| $89K | ﹤0.01% |
18,200
-35,000
| -66% | -$153K |
|
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.