PYPY vs. OOSP

Last updated Jun 23, 2026

PYPY (Yieldmax PYPL Option Income Strategy ETF) and OOSP (Obra Opportunistic Structured Products ETF) are both exchange-traded funds - PYPY is a Derivative Income fund actively managed by YieldMax, while OOSP is a Multisector Bonds fund actively managed by Obra. Both are actively managed. Over the past year, PYPY returned -39.50% vs 6.71% for OOSP. At a correlation of -0.04, they often move in opposite directions. PYPY charges 1.01%/yr vs 0.90%/yr for OOSP.

Performance

PYPY vs. OOSP - Performance Comparison

The chart below illustrates the hypothetical performance of a $10,000 investment in Yieldmax PYPL Option Income Strategy ETF (PYPY) and Obra Opportunistic Structured Products ETF (OOSP). The values are adjusted to include any dividend payments, if applicable.

Returns By Period

In the year-to-date period, PYPY achieves a -24.96% return, which is significantly lower than OOSP's 2.66% return.

PYPY

• 1D: -0.26%
• 1M: -4.78%
• YTD: -24.96%
• 6M: -26.42%
• 1Y: -39.50%
• 3Y*: —
• 5Y*: —
• 10Y*: —

OOSP

• 1D: 0.00%
• 1M: 0.36%
• YTD: 2.66%
• 6M: 2.87%
• 1Y: 6.71%
• 3Y*: —
• 5Y*: —
• 10Y*: —

*Multi-year figures are annualized to reflect compound growth (CAGR)

PYPY vs. OOSP - Yearly Performance Comparison

	2026 (YTD)	2025	2024
PYPY Yieldmax PYPL Option Income Strategy ETF	-24.96%	-30.17%	31.53%
OOSP Obra Opportunistic Structured Products ETF	2.66%	7.41%	6.27%

Correlation

The correlation between PYPY and OOSP is -0.06, meaning there is essentially no relationship between their price movements. Each responds to its own set of market drivers, making them strong candidates for combining in a diversified portfolio.

	Correlation
Correlation (1Y) Calculated over the trailing 1-year period	-0.06
Correlation (All Time) Calculated using the full available price history since Apr 10, 2024	-0.04

Return for Risk

PYPY vs. OOSP — Risk / Return Rank

Compare risk-adjusted metric ranks to identify better-performing investments over the past 12 months.

PYPY

PYPY Risk / Return Rank: 1
PYPY Sharpe Ratio Rank: 1
PYPY Sortino Ratio Rank: 1
PYPY Omega Ratio Rank: 1
PYPY Calmar Ratio Rank: 2
PYPY Martin Ratio Rank: 1

OOSP

OOSP Risk / Return Rank: 72
OOSP Sharpe Ratio Rank: 56
OOSP Sortino Ratio Rank: 59
OOSP Omega Ratio Rank: 68
OOSP Calmar Ratio Rank: 89
OOSP Martin Ratio Rank: 89

The rank (0–100) shows how this investment's returns compare to the risk taken. Higher = better. Based on the past 12 months of data, combining Sharpe, Sortino, and other metrics used by quantitative funds and institutional investors.

PYPY vs. OOSP - Risk-Adjusted Trends Comparison

This table presents a comparison of risk-adjusted performance metrics for Yieldmax PYPL Option Income Strategy ETF (PYPY) and Obra Opportunistic Structured Products ETF (OOSP). Risk-adjusted metrics are performance indicators that assess an investment's returns in relation to its risk, enabling a more accurate comparison of different investment options.

Values are calculated on a 1-year rolling basis and updated daily. Risk-adjusted metrics are more stable over longer periods — use the period switch above to explore them.

	PYPY	OOSP	Difference
Sharpe ratio: Return per unit of total volatility	-1.17	1.85	-3.01
Sortino ratio: Return per unit of downside risk	-1.53	2.68	-4.21
Omega ratio: Gain probability vs. loss probability	0.77	1.39	-0.62
Calmar ratio: Return relative to maximum drawdown	-0.84	5.13	-5.97
Martin ratio: Return relative to average drawdown	-1.41	19.00	-20.41

PYPY vs. OOSP - Sharpe Ratio Comparison

The current PYPY Sharpe Ratio is -1.17, which is lower than the OOSP Sharpe Ratio of 1.85. The chart below compares the historical Sharpe Ratios of PYPY and OOSP, calculated using daily returns over the previous 12 months. A higher Sharpe Ratio indicates better risk-adjusted performance relative to the risk-free rate.

Drawdowns

PYPY vs. OOSP - Drawdown Comparison

The maximum PYPY drawdown since its inception was -53.64%, which is greater than OOSP's maximum drawdown of -1.31%. Use the drawdown chart below to compare losses from any high point for PYPY and OOSP.

Drawdown Indicators

	PYPY	OOSP	Difference
Max Drawdown Largest peak-to-trough decline	-53.64%	-1.31%	-52.33%
Max Drawdown (1Y) Largest decline over 1 year	-47.14%	-1.31%	-45.83%
Current Drawdown Current decline from peak	-50.29%	0.00%	-50.29%
Average Drawdown Average peak-to-trough decline	-16.73%	-0.20%	-16.53%
Ulcer Index Depth and duration of drawdowns from previous peaks	28.04%	0.35%	+27.69%

Volatility

PYPY vs. OOSP - Volatility Comparison

Yieldmax PYPL Option Income Strategy ETF (PYPY) has a higher volatility of 6.99% compared to Obra Opportunistic Structured Products ETF (OOSP) at 0.44%. This indicates that PYPY's price experiences larger fluctuations and is considered to be riskier than OOSP based on this measure. The chart below showcases a comparison of their rolling one-month volatility.

Volatility by Period

	PYPY	OOSP	Difference
Volatility (1M) Calculated over the trailing 1-month period	6.99%	0.44%	+6.55%
Volatility (6M) Calculated over the trailing 6-month period	28.78%	2.18%	+26.60%
Volatility (1Y) Calculated over the trailing 1-year period	33.94%	3.66%	+30.28%
Volatility (5Y) Calculated over the trailing 5-year period, annualized	30.97%	3.32%	+27.65%
Volatility (10Y) Calculated over the trailing 10-year period, annualized	30.97%	3.32%	+27.65%

PYPY vs. OOSP - Expense Ratio Comparison

PYPY has a 1.01% expense ratio, which is higher than OOSP's 0.90% expense ratio.

Dividends

PYPY vs. OOSP - Dividend Comparison

PYPY's dividend yield for the trailing twelve months is around 74.46%, more than OOSP's 6.45% yield.

Position	TTM	2025	2024	2023
OOSP Obra Opportunistic Structured Products ETF	6.45%	6.71%	5.42%	0.00%
PYPY Yieldmax PYPL Option Income Strategy ETF	74.46%	64.68%	48.65%	5.70%

Frequently Asked Questions

Can I hold both PYPY and OOSP in my portfolio?

PYPY and OOSP have a correlation of -0.06, meaning they provide meaningful diversification benefit when combined. Depending on your allocation goals, holding both could reduce overall portfolio risk.

Which is riskier, PYPY or OOSP?

PYPY has higher volatility (6.99%) compared to OOSP (0.44%). In terms of maximum drawdown, PYPY dropped -53.64% vs OOSP's -1.31%.

Which ETF is better, PYPY or OOSP?

On 1-year performance, OOSP leads with 6.71% vs -39.50% for PYPY. On fees, OOSP is cheaper at 0.90% per year. On volatility, OOSP has been the lower-risk option at 0.44%. The better choice depends on whether you care most about return, fees, risk, or income.

Which ETF has performed better, PYPY or OOSP?

Over the 1-year period, OOSP has performed better with a 6.71% return vs -39.50%. Past performance does not guarantee future results, so compare this with risk, fees, and fund exposure.

Which ETF is cheaper, PYPY or OOSP?

OOSP is cheaper with a 0.90% expense ratio, compared with 1.01% for PYPY.

Which ETF pays a higher dividend yield, PYPY or OOSP?

PYPY has the higher dividend yield at 74.46%, compared with 6.45% for OOSP.

What is the main difference between PYPY and OOSP?

PYPY is categorized as Derivative Income, while OOSP is Multisector Bonds. They also come from different issuers: YieldMax and Obra. Their fees differ too: 1.01% for PYPY and 0.90% for OOSP.

Which has better risk-adjusted returns?

OOSP currently has the higher Sharpe Ratio (1.84 vs -1.17), meaning it's delivered slightly more return per unit of risk over the trailing 12 months. However, this ranking shifts over time - use the Risk/Return Score above for a more comprehensive view that combines Sharpe, Sortino, and other measures used by quantitative funds.