My name is Jason, and for the past two years I have been building and publicly documenting an income-focused portfolio built around option-income funds. The question that drives everything I do is simple: can a small portfolio generate meaningful cash flow without needing a traditional million-dollar dividend portfolio first?
According to Snowball Analytics, my portfolio has returned 128.88% since its inception around August 2024. Over the same period, the S&P 500 returned 45.42%. That is out performance by a very large margin, and unlike most ultra-high-yield investors, I did it while also maintaining a positive price return which currently sits at 16.24% since my portfolio’s inception in August 1, 2024. Its price turn has been as high as 35%. But, you know, sell offs happen.
Yes, you read that right. Despite holding funds with trailing dividend yields ranging from 30% to 130%, my price return is positive. Blossom (a social media site for investors with portfolio tracking features) only tracks price return, and even there I am currently at +16.24%. Not many people running ultra-high-yield portfolios can say the same.
If you want to verify any of this, look up JLP Holdings on Snowball Analytics. The portfolio is public.
My Unequivocal Position
Before I get into how I did it, I need to state something clearly, because the ultra-high-yield space is full of people selling you the dream of free money. Dividends are not free money. In fact, there is no such thing as free money. In order for there to be a cash flow, there must be a source from which the cash flows. Okay, well, perhaps the US government is somewhat exempt from this principle.
I view a dividend as a conversion to liquidity without selling shares. Total return is dividends plus price performance. If you understand integers, you know that price performance can go down enough to reduce the value of your investment even when dividends are reinvested. If the total return of the underlying assets is not high enough to support the yield percentage of the fund, your value will decline over time if you do not reinvest some or all of the dividend. Period.
In those cases, you can reinvest some or all of the dividends to try to keep the value of the investment level or growing. In some markets, you can grow your dividend income by reinvesting some of it even if the price of the fund is decreasing. The purpose of these funds is to extract liquidity while getting exposure to the price performance of the underlying asset(s).
If you have a very good year with SCHD or NOBL, the dividends will still pay you a small percentage relative to the value of your investments in those funds (though your yield on cost may rise which is a great thing). With ultra high yield funds, however, you have the option to take an outsized profit through dividends without selling any shares. You can spend the dividend, save it, reinvest it, or deploy the dividend into a different investment all together.
Thus, funds like YieldMax absolutely have viable use cases. What they do not have is a magic exemption from arithmetic.
The Numbers
The portfolio is currently producing income at a rate of nearly 46% of my cost basis. 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. Yield on cost of 45.79% against a current yield of 39.13% is only possible when the machine itself has appreciated. I will say that depending on what I was invested in at the time, and the price movements of my investments. My yield on cost has ranged from 30% to around 70%.
My Current Strategy
Over two years I have tried several approaches in this space: single-stock YieldMax funds, Roundhill’s index-based ETFs, Roundhill’s WeeklyPay funds, and REX Shares’ $NVII. The single stock Yield Max funds didn’t work out so well for me despite being concentrated in the magnificent seven companies. During that time, I lagged the indices. The Roundhill Weekly Pay ETFs targeted 120% of the weekly returns of an underlying asset using leverage. When I used these funds, my peak unrealized return in 2025 was nearly 60%. I had never used any sort of leverage before so I got to see what happens when there is a sell off in those underlying assets. I ended 2025 with a total return of 27.5% compared to the S and P 500’s 17.88%.
I had been stock picking off and on throughout my investment journey. Some years I did very well, other years I under performed. And, there were times when I picked investments that had very strong financials only to find out they were cooking the books (I’m looking at you, Kraft Heinz). Sometimes, financials were strong but the stock price would keep declining anyway. There were just too many factors with individual companies that I could not control.
That’s when I decided to return to a strategy that I had done earlier in my investment career. Instead of putting in all of this work to pick stocks that may or may not pan out regardless of the due diligence I did, I started picking market sectors instead. When you pick market sectors, if a company within that sector falls out of favor or shuts its doors, something else takes its place. And, you don’t have to pay very close attention to quarterly earnings for a bunch of individual companies. In spring of 2026, I started targeting semiconductors and, to a lesser extent, AI. When memory income funds like DRMY and YRAM came out, I started buying those as well (these purchases are recent).
That said, I prefer sector funds over single-stock funds. A single underlying can stall for years while you harvest a 40% yield while the price is potentially falling (and so too does the income you receive even if the yield stays at 40%). An entire sector with a genuine tailwind has to fail collectively before your principal takes the same damage. The risk-reward proposition is more favorable than betting on individual stocks.
Does this guarantee my price returns will never go negative? No. Nothing does except for insider trading (ask our esteemed American politicians to find out more). Can I position myself so that I can extract a large amount of liquidity from the portfolio in most types of markets, assuming the underlying does well? Yes. That is the game I am playing.
My protection against NAV erosion is the performance of the underlying asset(s). It’s not fool proof, but NAV performance will be significantly better with underlying(s) that perform well, and, underlying(s) with strong financials and a convincing bull thesis are likely to perform better. This is why I am targeting semiconductors, memory, and AI at this time.
Paying My Bills With a Five-Figure Portfolio
I am in a career transition from information technology to finance and wealth management. During this transition, I have been using the distributions from this portfolio to help pay my bills. Even while taking substantial income out and reinvesting only a small portion at times, the portfolio reached new all-time highs in June (I had started using the dividends to fund living expenses in April of 2026).
I am 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 depending on price movements. I hit the $21,000 figure while collecting 100% of the dividends for two months, minus a 10% reinvestment back into the portfolio.
This is not my only income source, but it is currently my largest. And it only works because I have managed, by skill, discipline, and, I will admit, very good luck, to build a life that is very inexpensive to live.
Now, could I have done this with $SCHD or $NOBL? At a portfolio of this size, absolutely not without selling shares. A $20,000 SCHD position yields roughly $1,400 a year. My portfolio was producing income at a rate approaching 46% of my cost basis. And on top of that, my total return over the period would have been significantly lower than 128.88%.
Make no mistake, SCHD and NOBL are great ETFs, but I’d need significantly more capital to pay bills with dividends with these funds.
For a smaller investor in a transition period, that is the difference between an income portfolio and a paper portfolio. Liquidity without share liquidation is the entire value proposition, and it only works when the underlying assets hold up when the underlying asset(s) do well.
What This Is Not
I would not suggest anyone retire off a portfolio of this size. I am not doing that, and this article is not advice to try. What I am demonstrating is a specific use case: an income bridge during a transitional period of life, funded by a small portfolio, without selling a single share.
One can sell shares for income, but when you sell shares, you lose the opportunity to continue to participate in that share’s returns. It’s like when you sell a hen that lays eggs. You can sell the hen for income, but you won’t have any rights to that hen’s eggs anymore. There are times you can sell shares and have more money in your portfolio after a period of time than before you sold the shares. There are also times that selling shares would have had a significant negative impact on the value of your portfolio. This is called sequence of return risks, and selling shares can lead you to realize the consequences of that risk.
Liquidation through dividends doesn’t complete mitigate this risk, but it is a liquidation strategy that is significantly more resilient to sequence of return risk in the long term.
If the semiconductor and memory sectors reverse hard, my price return will go negative and my income will shrink with it. If I stay the course, however, and my bull thesis plays out, I will have the opportunity to recover my capital because I still own the same amount or perhaps more shares if I’m reinvesting.
The Journey Continues
I plan to share this journey here and through other avenues. If you want to follow the performance and the philosophy behind the strategy:
You may follow me on Blossom Social here.
My YouTube channel will launch here in November of 2026.
You may follow me on X here.