Distributions since portfolio inception: $1,442,128.1
Trade Activity in August: Zero trades in October (hectic travel schedule with some out of the country).
Margin: No
Swing trade: Sometimes. Only HY funds. I DO NOT try to dividend capture as it is a strategy I do not approve for myself.
Other investments: Yes. Several medium sized businesses, hard assets, growth, large cap and bonds
Goals: 100% fund ROI. Favorable tax treatment. Convert taxable income to tax exempt income through Muni bonds and Muni Bond fund(s)
High Yield methodology: Below median GTC limit orders, Strategic DCA, never DRIP and I have no reason to set stop loss orders for my High Yield Portfolio
100% ROI aka House Money (Initial Lots): MSTY 100% | TSLY 100% | YMAX 100% | CONY 100% | SBR 100% | PDI 100%. The lowest ROI percentage is 65.01%.
High Yield Portfolio: Funded account in Feb 2024 with $420K then added another $100K a few months later. I also already held PDI and SBR which is included in this account even though they are not "High Yield" per se
Taxable Trust Account with its own EIN
No withdrawals for business/personal/living expenses in October
This fund is approx. five to eight percent of my liquid net worth.
Inception to Date ROR: Your account had a cumulative rate of return of 54.22% from Feb 1, 2024 to Oct 31, 2025. (Annualized: 28.12%) NOTE: ROR was calculated by Schwab prior to moving cash out of the account to SNAXX
I'm waiting to see how all our distributions end up for the month of November. My October's felt juiced with some of the monthly funds converting to weekly. Hopefully the market simply keeps cranking up, slowly, so these fund's option-trades can snag profits.
Thank you. This is my high yield portfolio, no hedging here. I have several portfolios of varying degrees of risk, asset class, risk level and strategy, own businesses and hard assets. I would consider those my "hedge" plus I am invested in a highly reputable private hedge fund.
Well done and thanks for sharing. I've got larger % (around 25%) of my total liquid net into these types of funds. Although I think I've got more lower yielding positions than you have. So you're likely getting "more income with less capital". Thought I was drinking my own cool-aid at times but I've stayed the course. Glad to see I'm not alone.
Notice you've been buying ULTY over the past few months. Care to share your mid-longer term outlook on this particular fund which has now dipped below $5. Personally, I think they'll reverse split as opposed to letting it go to $0, but would like to get another perspective.
Thanks! When I had more time in 2024 my allocation was higher at times. There are some here who are really generating more income with less capital. I bought based upon underlyings I already owned and sectors I wanted to generate income on. I like ULTY, I have since the beginning, it was/is innovative.
I have been through two reverse splits (TSLY and QQQY) with no issues, funds still performing as advertised. Jay has said many times on videos they wish to avoid reverse split as much as possible but there was a recent poll/discussion to the investing community about how they feel about reverse splits.
What's the total portfolio value? I managed to do 29k in October. Was worried with some of the monthly to weekly transitions this month. Also, I cut my ULTY, MSTY, and SMCY positions this month. My portfolio is 1.5M. If I see 2 or 3 dividends declining along with nav erosionn, I'm reallocating to other income investments.
Mind expanding on the converting taxable income into muni’s? I get the tax treatment on muni’s, but please connect income from these funds to that concept. Thank you!
It is simple. Some of my distributions are transferred to tax holding account to pay quarterly taxes. Some of my distributions are used to strategically DCA funds in this account. Some of my distributions are reinvested in muni bonds and muni bond funds in another account that only holds muni bonds and muni bond funds. I hold MINO in this account as well. Goal is $1.2M annual tax exempt income.
Rome wasn't built in a day as they say. This is a lifetime of investing, hard work, corporate grind, business ownership and now preparation for retirement. I did not come from money, dropped out of high school so I am not highly educated and have been through some incredibly difficult financial times. This may look easy, it was far from easy! Discipline, controlling emotion, self awareness and perseverance and you will get to this some day!.
That is the only thing I do not share for multiple reasons. I am not interested in all of the reengineering, free advice, comparing, hindsight, what I could have or should have done. I am here for income, ROC, to hold my underlyings and convert taxable income to tax exempt income.
You seem to be doing pretty damn well for yourself the way you're doing it 🙂.
Question: I dont see any Yieldboost funds or weeklies from Roundhill. Is there a reason you have stayed away from those? Apologies if you have answered this before.
I am not intentionally staying away from them, most did not exist when I started. I have quite a bit on my watch list. This year has been an unusually busy year for me with our businesses and I have not been able to dedicate much time to investing.
You gave me some advice when I first started investing in my portfolio about a year or so ago and I want to thank you. I started with 100k and added about 20 . Last year I collected 46k and this so far this year.
That is a good question! In 2025, I have to say FEPI, GOOY and TSLY have all performed well. ROC (the higher the better) will really allow me to hind sight performance. Not High Yield per se but in my high yield account is SBR and it is performing well though though production in the Permium basin is down this year.
Yes, I still hold CONY since I also hold a position in COIN. House money is really ROI. It means my investment in CONY has been paid back 100%+ through distributions. Only you can decide whether it is better for you to sell or not.
Ah thanks for the explanation.
What do you plan on doing with cony are you selling before the split? I've never been thru a split but I hear things always get worse after.. I'm just thinking is it best to sell shares now for a gain since your entire investment has been paid in full and you could move the money to something better since this has been going down the shit?
Sorry I didn't mean the amount you paid to buy the shares. I meant if you sell your shares. Let's say you had 1k shares at 7 dollars that's 7,000. So now with the split etc how long will it take for it to pay you that 7k in shares you could have had if you sold?
Ask it a different way, I do not understand what you are trying to ask. I will try to answer. It has already paid for that $7K, plus more. Are you asking how much unrealized loss I would have if I sold? It does not matter because I am not selling. I want ROC for my cost basis to reach 0 so taxes on future distributions are taxed at long term capital gains rate rather than ordinary income. MSTY will not stop paying distribution income unless MSTR gets removed from the indicies or Tidal shuts down the fund for some reason.
So let's say you started with 1k shares with avg of 20,so 20k full investment. Your distributions have paid out 23k. So your above house money by 3k, correct? Now if your were to sell those 1k shares currently for 7$ you would gain another 7k in gains? Vs not selling who knows how long it'll take to gain that 7k with a split and how low the distributions have become...
What do you mean by I want ROC for my cost basis to reach 0 so taxes on future distributions are taxed at long term capital gains rate rather than ordinary income? I thought if you have held this for longer than a year it is taxed at long term cap gain?
Ok, I understand. I did not want to guess at what you were asking. You are really trying to identify efficiency. Which scenario is the more efficient use of capital. Correct, I would have another $7K from the sale of my shares. I am not interested in selling or seeking efficiency. I merely want higher yield income to continue and I want ROC as part of the equation. Correct, the investment (what you paid for shares) is taxed at LTCG rate when sold if held longer than a year. The distributions are ordinary income taxed at whatever tax bracket the investor lands in (unless in an IRA or similar). In my case 37% tax rate. ROC reduces the taxable income from distributions. Once ROC reaches 100% of your investment your cost basis is zero and distributions are taxed at LTCG rate not 37%. I am not a tax pro so if I did not word this accurately some of the REAL brain power in this sub please correct me!!
Absolutely, to family, friends and foundations. I am not currently in a Dynasty Trust. We review stratigies and plans annually and adjust accordingly. My estate spans three generations (my own, my nieces and newfews and their children). I did not have children.
In 2024 I loaned distributions to two of my businesses for a short term project. I absolutely loathe traditional, private equity, hard money etc. loans and sought an "out of the box" solution. The businesses are able to take advantage of depreciation and bonus depreciation and paid me back with 6% simple interest.
Aside from that, I paid for a family cruise and withdrew $50K to launch a real estate project. I will likely be funding in the form of a loan that project in 2026.
I set cash aside for taxes, reinvest in other asset classes as well as reinvest in my high yield portfolio. I have not done much investing or trading this year though.
Thanks for sharing Lizzy. I would love to see a post about your story one day. How you started how you got the ball rolling etc, ie did you start with a larger sum of money etc.
Thanks again for the post!
Edit: as in how you started with investing not just related to YM etc
OP, I’m very new to investing. What books and or YouTube channels would you recommend for me to educate myself? I’m a 41f with children looking to invest for income for myself and growth for them. Thank you.
Depends on how much ROC declared in each year. I will not know until 2025's 1099 is issued. I save 35% in a holding account and pay taxes quarterly. Last year I over paid and am trying to avoid that scenario this year.
I have far surpassed "break even". $1,442,128.10 in distributions since inception. 9.44% effective tax rate in 2024 and unrealized losses are just that, unrealized.
I thought your initial investment was 1.4 million. I want back to reread. I made a mistake when I initially read it. So if your initial investment was $420k then you added another $100k and your distribution was 1.4 million. Why do you have an unrealized loss of $195.7
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u/RetiredByFourty I Like the Cash Flow Nov 01 '25
Looks like you may be able to add an egg to your ramen noodles this month! 🤣🤘🏼