Lower yield now but dividend and price grow consistently. The long-game compounder. Most tax-efficient holding in the account (qualified dividends). Still the largest position at ~18.8%, but the September rate shock knocked the price from $35.01 to $32.69 and nearly erased the gain (+1.8%). Nothing about the thesis changed; a cheaper SCHD just means cheaper DRIP shares.
A real, self-directed dividend experiment · run on Fidelity
The Drip Fund
Every dividend reinvests. More shares, more dividends, more shares. Slow, steady, relentless compounding. Water wears down stone.
Snapshot as of October 5, 2026 · prices as of this snapshot · live off
Why this exists
Turning a tiny seed into something real.
I started The Drip Fund with a small stake — somewhere around $5,000, honestly I don't remember the exact number — and I feed it maybe $100 a month when I remember to, for one reason: to find out, with real money in an account I can actually log into, whether the slow magic of dividend reinvestment truly works. Not in a spreadsheet. For real.
Let me be clear about one thing up front: this isn't my retirement plan, and it isn't my only investment. The serious, boring heavy-lifting happens elsewhere — a 401(k) and a Roth IRA, where it belongs. The Drip Fund is the sandbox: a small pot of real money I play with out in the open, on purpose, just to illustrate the point and show anyone who'll look how powerful this quiet little engine really is.
Here's the beautiful part. Every dividend these holdings pay never touches my pocket — it instantly buys more shares. Those shares pay their own dividends, which buy more shares again. It compounds quietly in the background while I sleep, while I work, while I forget it even exists. Water wearing down stone.
And this is the part that gets me: the dollars in here are modest, but the engine is the exact same one that builds serious wealth. If these were bigger numbers — or if I'd simply started at eighteen instead of in my fifties — that same machine, handed thirty or forty years, doesn't just supplement a retirement. It lets you walk away from work early and never look back. This little account is a proof of concept for a very big idea.
One account, one job
A taxable brokerage account with one job: build a growing stream of passive dividend income to supplement retirement. Not the primary retirement vehicle (that's a 401k and Roth IRA) — this is the income supplement: money that shows up every month whether you work or not.
Where the money sits
Allocation by position · colored by tier
Who actually pays the bills
Estimated annual dividend income by position
Winners & laggards
Unrealized gain / loss in dollars — the cost of patience and the reward for it
The Core Five
The Core Three were three slices of one basket — all US, all large cap, all moving together. On Aug 20, 2026 SCHY and O were promoted to fix that: SCHY is the only holding that adds genuinely diversified non-US exposure, and O is the only non-equity asset class in the core. All five are dividend funds, and each one does something the other four don't.
Contribution rule: One target at a time: the entire contribution goes to the most underweight Core Five member until it hits its target weight, then the next in the queue. Minimum $200/mo, targeting $300-500. Fidelity allows dollar-based fractional purchases — type '$67' instead of a share count.
Why one at a time: Splitting a $250 contribution five ways is $50 a position. At that rate SCHY needs nearly three years to matter. Concentrating on one target at a time gets it there in about seven months, and the portfolio ends up in the same place either way.
Every position, on its own sheet
Twelve holdings, sorted into three tiers: Build (new money goes here), Hold (let it DRIP), and Monitor (watch, maybe trim).
Tier 1 — Build
— Monthly contributions go here 5 positionsAll new monthly contributions go to these positions only. No new positions without strong justification.
Same covered-call strategy as JEPI but Nasdaq / tech-heavy. Higher yield with more growth upside. Its SEC yield matches its distribution yield — the income is real. Tech held up through September while dividend stocks fell, so it is now slightly over its 12% target. Still the single biggest income producer in the account at ~$297/yr, roughly a quarter of everything the fund pays.
S&P 500 covered-call ETF. Monthly dividends, quality management, sustainable yield, low volatility. It hovered within a percent of break-even for months, and the September rate shock pushed it to -2.9%, while it kept paying 7-8% in distributions the entire time, which is the whole point of the product. Took the September contribution: $300 on Oct 5, bought at the dip under the older plan that had JEPI next.
'The Monthly Dividend Company.' 30+ years of dividend increases. Monthly payer. Promoted into the Core Five on Aug 20, 2026, which finally resolves a contradiction: O was tagged Tier 1 Build while the contribution rule said 'JEPI, JEPQ, SCHD only', so it sat in the top tier and never received a dollar. It is also the only non-equity asset class in the core. Then rates hit: with the 10-year Treasury above 5% for the first time in nearly 20 years, O fell to a 52-week low and is now -19.6%, the account's biggest loser. The dividend itself is untouched, so every DRIP share now buys about a 6% yield.
International diversification — the global cousin of SCHD, and screened the same way: 10+ consecutive years of dividend payments plus quality and dividend-growth filters. Promoted into the Core Five on Aug 20, 2026 as the fix for a portfolio that was otherwise ~97% US by any diversified measure. It had been starved since March, which is why it is first in the funding queue. The September contribution went to JEPI under the older plan, so SCHY's turn starts with the next one. Expect lumpier payouts than SCHD — foreign companies often pay semi-annually and size the dividend to earnings rather than growing it smoothly.
Tier 2 — Hold
— DRIP, do not add 6 positionsHeld and allowed to DRIP. Do not sell, do not add. Let compounding work.
Yield around 4.2%. Held for income and energy exposure. Barely moved since August while most of the account fell, so its weight crept up to ~17.0% anyway. Still second to SCHD. Watch for dividend policy changes.
Held for a huge unrealized gain (+$2,316, +559%). Worth more than six and a half times what it cost, on a cost basis of $414. Hold, do not add. Let DRIP work.
Solid regional bank with a growing dividend. Up +131% on a $613 cost basis, down from +158% in August as rising rates hit bank stocks.
60+ year dividend grower. Never cuts. Boring perfection — a $1,000 position built on nothing but price growth and reinvested dividends.
Recovered well, dividend growing again. Up +190% on a $316 cost basis. The September dividend arrived and DRIP added its first new shares since June.
Mortgage REIT, acceptable risk at the current small size, yields well. Punches far above its weight on income — 2.2% of the account producing about 7% of the dividends, which is precisely the pattern that deserves scrutiny rather than admiration.
Tier 3 — Monitor
— Watch quarterly, may trim 1 positionWatched quarterly. Off-strategy or concentrated positions that may be trimmed.
Not a dividend-income play and doesn't fit the strategy cleanly, but the gain has held between +34% and +37% for three straight check-ins and it keeps paying monthly.
Known risks, eyes open
No portfolio is perfect. These are the parts being watched on purpose.
BP concentration (second-largest)
BP is ~17.0% of the portfolio, up from 16.8% in August. Not from buying: it held its price while rising rates pulled the dividend stocks around it down. SCHD is still ahead at ~18.8%. Do not add. The unrealized gain is about +$1,991, so selling carries a real tax cost. BP cut its dividend in 2020.
Covered-call concentration (improved)
Down to JEPI and JEPQ — two covered-call products, about 24% of the account, from three products and ~28% before XYLD was sold. In a strong bull market, covered calls still cap upside. An accepted tradeoff for consistent monthly income, now taken in a smaller dose.
NLY interest-rate risk
Mortgage REITs are rate-sensitive and have historically cut dividends, and the September rate jump showed it: NLY fell about 22% in six weeks. It is 2.2% of the account but produces about 7% of the income, a ratio that argues for scrutiny, not comfort. The $0.75 quarterly dividend held, which now works out to a ~16% yield, past this account's own 15% warning line. The check that matters for a single stock is whether earnings available for distribution cover the dividend. Position is small (~$521).
The snowball, ten years out
Drag the dials and watch the DRIP compound. Honest warning: the future is a guess. That's why you can flip to a range of outcomes instead of one confident line — markets don't move in straight lines, and neither should a forecast.
Projected value & monthly income
Reinvested dividends compounding over time
Read this before you get excited
These projections are optimistic. A covered-call-heavy portfolio may deliver yield but underperform on growth in strong bull markets. A more conservative, realistic target is roughly $450–550/month of income by year 10 at $300/month contributions. A covered-call-heavy portfolio trades upside for income, so in a roaring bull market this will likely trail a plain index fund on price — by design. The forecast assumes a steady average; real life arrives in lumps.
The document's own table
Assumes 9% total annual return, 6% blended yield, starting value ~$24,200. — for comparison against the sim above.
| Monthly | Year 3 | Year 5 | Year 10 |
|---|---|---|---|
| $200/mo | $2,230/yr | $2,980/yr | $5,530/yr |
| $300/mo | $2,470/yr | $3,420/yr | $6,660/yr |
| $500/mo | $2,950/yr | $4,300/yr | $8,910/yr |
| $750/mo | $3,550/yr | $5,400/yr | $11,710/yr |
The theory
Every dividend reinvests. More shares, more dividends, more shares. Slow, steady, relentless compounding. Water wears down stone.
A taxable brokerage account with one job: build a growing stream of passive dividend income to supplement retirement. Not the primary retirement vehicle (that's a 401k and Roth IRA) — this is the income supplement: money that shows up every month whether you work or not.
The rules that never change
Ten commandments. They exist mostly to stop the investor from doing something clever.
The yield trap
The single most expensive lesson in the whole account — learned, thankfully, on a small position.
QYLG: 19.44% that wasn't real
Distribution yield includes option premiums and return of capital. SEC yield measures actual investment income. If a fund shows 19% distribution yield but 0.3% SEC yield, most of what it 'pays' you is your own money handed back in a different pocket — which is why the position loses value over time. Always compare both numbers before deciding.
The gap between those two bars is your own capital being handed back to you and called income. A high distribution yield reflects what was paid, not what will be paid. BDCs and struggling companies often show inflated yields precisely because the market is pricing in risk of cuts or collapse. Always ask: why is the yield this high? If the answer is 'the price has been falling for years,' that is a red flag, not a buying opportunity. PSEC and OXSQ both destroyed capital while advertising double-digit yields.
Cleanup days & check-ins
Every decision this account has made, newest first — three deliberate restructurings that turned a cluttered 19-position grab-bag into a focused 12-position income machine, plus the quiet months in between.
Nothing sold. The 10-year Treasury crossed 5% for the first time in nearly 20 years, and the rate-sensitive holdings took it on the chin: NLY -22%, O -15%, MTB -10%, SCHD -7%. Tech went the other way, with Apple, JEPQ and QQQH all up. DRIP kept reinvesting through all of it. The September contribution had been sitting in the money market; on Oct 5 it went into JEPI, as the plan before the Core Five said it would.
A strategy change, not a trade — nothing was bought or sold. The Core Three turned out not to be three baskets but three slices of one: SCHD, JEPI and JEPQ are all US, all large cap, and all fall together. Diversified non-US exposure was 2.95% of the account against a global market weight nearer 37%, and there was no non-equity asset class in the core at all. SCHY and O were promoted to fix both gaps.
Decided and executed the same day; the sale and the repurchase both cleared faster than expected. $1,052 moved out of XYLD and into 30 more shares of SCHD at about $35.07. The first position sold purely on structure rather than performance — XYLD was up, and was sold anyway.
No cleanup needed. All new money went to SCHD and JEPQ — together they picked up about $560 of fresh cost basis between contributions and reinvested distributions. Every other position simply DRIP'd its own dividends. The account crossed $24,000 and, for the first time, annual dividend income passed what gets contributed by hand.
Trimmed the last loose ends — sold the final two off-strategy positions and deployed $600 in new cash.
A major restructuring: the account went from a cluttered 19-position portfolio to a clean, 15-position, strategy-aligned one.
The graveyard
Sold and not coming back. Each one taught something.
The plan from here
Every month
- Deposit the contribution ($200 minimum, $300–500 target).
- Send the whole contribution to the current queue target — SCHY first, then O. Do not split it five ways.
- When a target reaches its weight, move to the next in the queue. When the queue is empty, resume even splits across the Core Five.
- Confirm DRIP is active on all positions.
- Do nothing else.
Every quarter
- Review all positions against their tier.
- Check NLY for dividend sustainability news.
- Check BP for any dividend policy changes — and whether the ~16% weight is still tolerable.
- Decide QQQH. It has survived four reviews now and was rejected for the core — either sell it or write down why it stays.
- Confirm no cash is accumulating in the money market unnecessarily.
When the mortgage dies
- Redirect a significant portion of freed monthly cash flow here immediately.
- Increase the monthly contribution substantially — this is the inflection point for the account.
- Target moving to $500–750/month contributions.
For personal planning and entertainment only. This is one real person's real portfolio shown as a learning exercise — it is not financial advice and not a recommendation. Always consult a licensed financial advisor before making investment decisions.
To the keen observer 👀
You noticed it, didn't you. The fund throws off about $1,254 a year in dividends — and I shovel in roughly $100 a month, call it $1,200 a year. So for most of this account's life, the dividends have merely matched what I add by hand. “Aha,” you think, “the compounding isn't really doing much — he's basically paying himself.”
You're sharp to catch it, and for a long while you'd have been right. But look at the date on this snapshot: as of August 2026 the dividends have quietly passed my contributions. Here's why that matters more than the size of either number.
The two lines are on completely different trajectories. My contributions are flat — a hundred-ish bucks a month — and honestly they'll stop once the mortgage is gone. The dividend income is a curve that bends upward: every dividend buys more shares, those shares pay more dividends, and the companies themselves keep raising their payouts. One line is a straight road; the other is a snowball rolling downhill.
When I started, this gap was enormous. A ~$5,000 seed paying maybe a couple hundred dollars a year, dwarfed by what I was adding. Today the dividends sit at about $1,254 — still ahead of the ~$1,200 I hand it, though only just. Selling XYLD in August deliberately gave back about $82 of annual income in exchange for better total return and a smaller tax bill, which narrowed the gap to a sliver. I'd rather own the better portfolio and win the race by an inch.
The crossover is the whole point, and it just happened. Next the dividends double my contributions, then they make them irrelevant. Stop adding money entirely, today, and the dividend line just keeps climbing on its own — that's the difference between saving and owning something that pays you.
So yes — for years it looked like I was only feeding a piggy bank. As of this snapshot, the piggy bank has started feeding me.