I want to introduce myself to the Blossom community. My name is Jason, and I am building and publicly documenting an income-focused portfolio built around option-income funds. I am especially interested in whether a smaller investor can generate meaningful cash flow without needing a traditional million-dollar dividend portfolio first. Despite the title, my portfolio is not all YieldMax, but it is predominantly so (most of my portfolio is currently in $CHPY), and it was all I could fit into the title while making it catchy. Blossom only tracks my price return, which, despite being in ultra-high-yield funds, is currently at +16.24%. This is while harvesting a trailing dividend yield that ranges from 30%–50% and a yield on cost of 30%–71%, depending on price movements throughout the year. If you want to see my total returns during multiple periods of time, look up JLP Holdings on Snowball Analytics. The portfolio is public. The link to that portfolio is also on my profile page. I do want to state my position unequivocally. Funds like YieldMax do have viable use cases. I view a dividend as a conversion to liquidity without selling shares. Total return is dividends plus price performance. If you know about mathematical operations with integers, you know that price performance can go down enough to reduce the value of your investment even when dividends are reinvested. So, dividends are not free money. It is possible that your value will decline over time if the total return of the underlying asset(s) are not high enough to support the yield percentage of the investment. In such cases, you can reinvest some or all of the dividends to try to keep the value of the investment level or growing. I, however, over the past two years, have managed a positive price return with significant income on a small portfolio. Not many ultra-high-yield investors can say the same. Will I always be able to collect all of the dividends every year without my capital decreasing? No. Can I position myself where I can extract a large amount of liquidity from the fund in most types of markets assuming the underlying does well? Yes. The strategy I currently use targets sectors that I think have tremendous upside potential. Right now, it is semiconductors, memory, and, to a lesser extent, AI. The outsized performance helps guard against NAV erosion. It does not guarantee that my price returns will never go negative, but the better the underlying performs, the less likely you are to see NAV erosion. According to Snowball, my portfolio has returned 128.88% since its inception around August 2024. Over the same time period, the S&P 500 returned 45.42%. That means my portfolio has outperformed the S&P 500 by a very large margin so far. My current portfolio yield is 39.13%, while my yield on cost is 45.79%. In other words, based on what I originally invested, the portfolio is currently producing income currently at a rate of nearly 46% of my cost basis. It also reflects that my portfolio has had a positive price return and my dividends on a per-share average basis have grown along with the price of the fund. The portfolio has not followed one static strategy the entire time. I started with a mix of YieldMax single-stock funds and Roundhill ETFs. I later used several of Roundhill’s WeeklyPay funds and REX Shares’ $NVII After that strategy gave back a significant amount of its gains in 2025, I changed direction. Since March 2026, I have been focused more heavily on sector-based option-income funds, especially $CHPY . $CHPY has been the clear core of my portfolio for most of this period. I also currently have $GPTY, $DRMY. and $YRAM in this portfolio. I did hold $SEMY for several months as well. I have been using the distributions from this portfolio to help pay my bills since April 2026 during a career transition. Even while taking substantial income out and reinvesting only a small portion at times, my portfolio reached new all-time highs in June. This is not my only income source, but it is currently my largest source of income. Luckily, I have managed by skill, discipline, and, admittedly, very good luck, to build a life that is very inexpensive to live. Can you imagine? i am currently 40 years old and I have been paying a majority of my bills with a portfolio that ranges in value from about $13,000 to $21,000, based on price movements. I achieved the $21,000 figure while collecting 100% of the dividends for two months at that time, sans a 10% reinvestment into the portfolio. I would not have been able to pay most of my bills with $SCHD or $NOBL with this size of a portfolio without having to sell shares. Not to mention, if I invested in $SCHD or $NOBL instead, my total returns would have been significantly lower. Of course, I would not suggest anyone retire off of a portfolio of this size. The portfolio has been valuable as an income source in a transitional period of my life, and I'm very thankful for it. This is not something I could have done with SCHD or NOBL without having to sell shares. Specific uses cases for these types of funds are something I want to talk about on my page. So, I hope the performance of my portfolio interests you. I plan to share my journey here and through other avenues. Feel free to check out my investment newsletter, Rethinking Dividends, at rethinkingdividends.com. If you are interested in seeing the journey and the philosophy behind my investment strategies, feel free to follow me and/or subscribe to my Substack newsletter. I also plan to start a YouTube channel in November of 2026. Here is the link to where this channel will be: https://www.youtube.com/@rethinking.dividends.
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6 Comments
Jim Candoit@aldis · 9h
I have been happy with CHPY and GPTY and will be adding LFGY on Tuesday as I think Crypto is turning the corner. As much hate as they get, Yieldmax actually has several great funds.
Deadasshionately Maker@mkrdvdnd · 8h
I had semy for a while. It went to shit. I Hold chpy gpty and lfgy. Just got back into chpy. Sold off at ath. Happy with those. I also swing trade roundhills.
Danny L@danny00 · 8h
@rethinking_dividends Would you recommend Covered Calls ETfs (high yield funds) for someone in there 20s? Should I take on risk
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