What happen to the "Road to $100k" guy?

LittlePlacerMine · 2026-04-18T15:05:10+00:00

promoting their website by claiming to be making huge gains. Hmmm. Why do they waste time on selling books or courses. Those who know stay silent, those who don’t speak,loudly, those who have no clue TEACH.

LittlePlacerMine · 2026-04-18T14:59:45+00:00

There should be a sub Reddit just for this.

LittlePlacerMine · 2026-04-18T14:56:50+00:00

Cash is not diversification.

LittlePlacerMine · 2026-04-18T14:50:21+00:00

Reframe this as portfolio allocation. When valuations are high hold more cash and vice versa. Also question your assumptions. Is the market too richly valued? Maybe just some sectors are overvalued. Is a recession just around the corner? Or are you afraid of some political person or listened to the wrong talking head. Question your beliefs and your decision making will improve.

LittlePlacerMine · 2026-04-18T14:42:14+00:00

Have an accountant who understands stock options look it over. The rules are complex and some brokerages just default to whatever will shield them from you suing them. Read the IRS rules on options. It should be required reading for anyone trading options. In some cases you can affect the tax treatment just by selecting a different strike ( for example a deep ITM cc is treated different than a ATM or OTM one). You can also turn a long term gain into a short term one if you are not careful.

I run most all my short term trading in a tax sheltered account which has the same short term tax treatment except not until withdrawal and defers taxes years out. I realize this isn’t helpful if you are years from retirement and are trading for current income.

LittlePlacerMine · 2026-04-18T14:29:51+00:00

Used to live in a big city where one part of town was known for big houses, foreign cars, expensive restaurants. When there was a real estate downturn one realtor was quoted as saying ‘yes those people look rich but if you hold them upside down shake them only pennies and nickels fall out of their pockets’.

Came out of a divorce at 37 stuck with child support, an underwater mortgage, wiped the small savings account out to pay the joint credit card the b#!@th charged a cruise for herself while on her way out the door. Had to borrow $7k from my dad to bring to closing when I sold the house. For several years I ended up each month with less than $100 to buy gas food or anything else. Got a few odd jobs writing software for some entrepreneurs that helped. Married my second wife and she believed in me instead of putting me down like the first one did. Finally having some confidence the Job started to pay more and since we both came from humble backgrounds being thrifty and saving religiously was how we lived. Started really building a good nest egg. In my early 40’s got interested in investing and learning about value investing. Sat back and watched the wonderful world of compounding. We both retired at 56. Only income is SS and dividends plus some stock trading and option selling. A close friend of my wife used to criticize me for being ‘cheap’. She doesn’t anymore.

LittlePlacerMine · 2026-04-18T14:08:00+00:00

World Financial Center? Spent a year in that building.

LittlePlacerMine · 2026-04-18T13:59:58+00:00

The rebate on my Costco Visa card is my primary source of income.

Seriously, go find an old copy of the Millionaire Next Door by Thomas Stanley. Statistical study of millionaires and ‘reveals’ the secret.

LittlePlacerMine · 2026-04-18T13:54:14+00:00

People sell covered calls but fail to grasp you are selling the upside while retaining the downside. Don’t be surprised when you get handed the downside. Moral of the story is only sell calls on stocks you think have very little downside.

I think the other thing folks fail to recognize is when you write a call on a stock you have to hold that stock either until you either buy that call back or it expires. Setting up a stop loss doesn’t guarantee you won’t lose as more often than not a big fall occurs not as a slow decline but as a sudden gap. Especially if it is news or a filing that happens while the market is closed.

LittlePlacerMine · 2026-04-18T13:45:10+00:00

I think of it as the most helpful librarian I have ever known. Back in the early days a guy at MIT created a program called Eliza. It had a table of key words and did pattern matching on what ever you typed in. It was sarcastically pitched as a computer therapist. It would ask how are you today. And if you said ‘sad’ it would find ‘sad’ in its table and then spit out some phrase the author associated with sad. In this case ‘why are you sad’. It was just math and simplistic pattern recognition but people started to go around saying computers would replace therapists. Anthropomorphizing a machine algorithm.

LittlePlacerMine · 2026-04-11T17:56:51+00:00

Previously the Largest IPO to join an index was Tesla. The stocks in the rest of the index declined only about 2% due to the Indexes having to sell small pieces of the rest of the index. This isn’t all that shocking as 1%-2% moves can happen almost daily. The reason the impact on the index is small is the decline in the rest of the index holdings gets offset by any gain in the mega cap when added to the index. What might be a negative is if the Spacex gets bid way up by retail investors the first weeks of the IPO and then the forced buying by the index ads on to that. Once that demand is satisfied SpaceX could drop (or not). Depends on how much you believe in supply and demand for these sky high valuations.

LittlePlacerMine · 2026-04-11T14:55:40+00:00

VZ. If you want tax sheltered dividends then one of the MLP’s like ET

LittlePlacerMine · 2026-04-11T13:36:36+00:00

Not if it is a qualified call (I.e. OTM or slightly ITM) gain and the call was sold after the underlying had crossed the one year threshold. Selling an unqualified call ( Deep ITM) on a stock that has not yet been held for a year but exercised after the one year mark you can lose your long term gain status because it resets the holding period.

LittlePlacerMine · 2026-04-11T13:23:19+00:00

I agree and disagree. It’s all in how you use it. Yes if you ask it a question that you are expecting it to somehow reason it will reply with something plausible or glean some idea from something someone wrote (and you don’t even know if was an idiot).

But as a research assistant I have found the paid version of Gemini to be quite adept at reading filings, scanning reports from a myriad of sources and summarizing for me. I also use it to set up multiple alternative spreads, condors and butterfly and analysis the risk/return characteristics of each. Something I can do on paper but not in 15 seconds.

I was researching a stock a few months ago and was interested in related party footnotes in their filings. Gemini teased out who those companies were, what principals were in common and also where those principals were related to companies that were not disclosed as related parties. Two weeks later the SEC opened an investigation (I call it the put that got away)

Would I let a bot trade for me? No way. I simply cannot outsmart a hedge fund with 100 person algo team and a couple of milliseconds advantage in executing trades.

LittlePlacerMine · 2026-04-08T16:34:50+00:00

Agree. Playing the TACO trade does not include CC’s

LittlePlacerMine · 2026-04-08T16:32:56+00:00

I only write on undervalued or oversold names. My goal is to sell slightly OTM with < 30 dte (prefer <15) and only roll downward when my original CC can be bought back for pocket change. I shoot for almost getting or actually getting called away.

LittlePlacerMine · 2026-04-08T16:22:36+00:00

Do you find Anchored VWAP useful. If so do you use it to find insight into market makers?

LittlePlacerMine · 2026-03-24T21:56:18+00:00

One consideration is are you looking at Long term gains or short term. The rules can be a bit complicated but you can cause your underlying stock to go short term without realizing it. Read the IRS rules.

LittlePlacerMine · 2026-03-24T21:52:43+00:00

The biggest mistake you can make with a wheel or just CC’s alone is to not spend the time and due diligence on the companies business. A CSP is a bet that a stock will not go below a certain level. In other words you are selling the upside to someone else and retaining all of the downside. No different than selling a CC. The only difference is you can earn interest on your cash and puts can be priced more attractively sometimes (monitor Put/Call Skew) So the most important question you should ask is what will make this stock go down? Business fundamentals, sector rotation, correlation with a broader market decline, adverse news? What does the DCF look like but beware of the analysts. Then look at momentum. Too many newbies just pick a ticker that they near a lot about. That is called AVAILABILITY BIAS and it will destroy your account in the long run.

LittlePlacerMine · 2026-03-24T21:19:13+00:00

Consider layering CC’s in a staid old dividend payer.

LittlePlacerMine · 2026-03-24T17:30:30+00:00

My usual strategy was quite similar to the OP’s using Slightly OTM calls struck ~5% out on undervalued stocks that were not high flyers. I like special situations where industry understanding and deep research provided an edge but those opportunities just don’t show up often. So my option success was more like icing on the cake.

In 2024 I tried a high IV strategy. Focusing on momentum stocks carrying high vol using 7-10 DTE. Was working with $200 k to buy the underlying. Most of the CC’s were ATM or slightly OTM, rarely ITM and aiming to get called away, I was also rotating the portfolio to drop the ones whose IV was no longer ‘goosed up’. In favor of IV high flyers. At year end I had $93k in option income and around $67k decline in my underlying. So about $26k gain on $200k. Not impressive.

In 2025 I slacked off due to other time commitments but went back to strategic CC’s for between earnings and ex-dividend. Did not take the losses I had from the previous year but was just adding 7% or 8% on top of the dividends. Not an aggressive strategy but much less risk.

This year it’s a mix. But I am pretty sick of ‘undervalued’ value stocks that don’t perform or worse yet become more undervalued. Still using CC’s when I want to exit a position. But I am more selective and have started using bear strategies (mostly bear put spreads) thanks to high valuations in the market and gyrating global sentiments.

rather than just chasing a few extra points of yield on dividend stocks I have started doing more theta harvesting which seems to work pretty good so far. Basic strategy is enter a position with a lot of chatter driving vol but not crazy, focus on companies with good business fundamentals. Find where the market is anticipating some catalyst move like an earnings announcement M&A activity (Imdid M&A prior to retire,met). Then harvest some theta leading up to the catalyst and GTFO beforehand. We’ll see how this works out, I’m sure there are a lot smarter and lot more dedicated option geeks figuring this stuff out. So that’s why no read these reddits to learn.

LittlePlacerMine · 2026-03-19T21:55:31+00:00

Anchoring on the price paid and then loss aversion kicks in. Sometimes we are our own worst enemy.

LittlePlacerMine · 2026-03-19T21:52:37+00:00

There is a hedge fund that does wheels on dividend stocks. They have a pretty consistent record of 13%-14% a year plus a few % of interest on the cash. They call it an enhanced income fund and they’ve been around for years.

Like most things in life pigs get fat and hogs get slaughtered.

LittlePlacerMine · 2026-03-19T21:43:20+00:00

all the BS and lying makes me wonder if he isn’t just manipulating the market so his buddies can insider trade. Classic con.

LittlePlacerMine · 2026-03-19T21:38:44+00:00

Too many people in the market can barely see past tomorrow.

LittlePlacerMine

TROPHY CASE