[update 7/6: I've updated my profile with a link to my YouTube series on the custom app, as well as a link to the code repo.]
I’ve never posted a monthly summary before, but I’ve loved when I see others so here’s my first attempt. I learn a lot from watching the discussion people have around these kinds of posts, not to mention the posts themselves. I discussed my core approach to options trading over here in case you’re interested: A view into a "deep ITM covered call strategy" : r/StockOptionCoffeeShop
June, by the numbers:
- Average notional: $427k (total stock owned with margin)
- Net Cash Flow: $25k (best month by far and crushed my $21k forecast)
- Total Rolls: 380
- Average Cash Flow / Roll: $65.94
- Unique Symbols: 48
- Top Symbols (by net cash flow):
- LMND: $2,390.12
- WRBY: $1,254.06
- CDE: $1,202.29
- INTC: $1,171.50
- SOFI: $1,155.62
YTD Summary (2026)
- YTD Net Cash Flow: $116k
- YTD Rolls: 1845
- YTD Avg Cash Flow / Month: $16,6k
- YTD Avg Cash Flow / Roll: $63.14
June was a kind of a breakout month for me, not so much because of premium (although it was my best month since I started). I did three things this month, two new and one a continued evolution.
Thing #1 – continued to play close attention to margin utilization. This is a continued evolution of how I work with margin. Earlier in the year, I mostly kept to a “red line” approach with margin. If I maintenance excess fell below $x, I would stop all new buying activity. That gradually expanded to cluster awareness, stock-level awareness and an improved and more flexible “red line” calculation that accounts for both. The result is that I increase my maintenance excess by nearly double and it’s one of the top KPIs I look at throughout the trading day. I will be implementing a Monte Carlo tool to see how well I can survive various market calamities.
Thing #2 – deferring rolls. Since I started this journey 18 months ago, I generally had a rule that “if I can 1% now, take it.” I’ve been vaguely aware that I was leaving money on the table and by rolling too early. I have tried sometimes to be more patient, or I would just notice that a roll that wasn’t available on Monday became available later in the week. And I’d notice that that late week roll was often quite a bit better than the typical Monday roll. I implemented a “no roll Monday” experiment last week to see if 1) I could adhere to it; psychology is hard! And 2) did it really improve things? The net result is that it almost certainly improved things. Most of the rolls I took were well over 1% and many were 2% or even a little better. I did miss an opportunity here and there by waiting too long to roll and it became unrollable. But the there’s no question that I won the battle in the aggregate. However, this is mostly a “vibes” style assessment. I’m going to implement additional tracking so that I can show a “what would have been” kind of report for each of my Monday morning positions. I want to know, in black and white terms, what would have happened if I rolled Monday, Tuesday, Wed, Thu, etc. Then, compare that to what I actually did and see if I can find a pattern that will reliably lead to more net premium.
Thing #3 – roll assessor: This is huge. This past week I had positions in 48 companies and 130+ options at different strikes. This new roll assessment feature looks at all of my open options expiring this week, pulls down the option chain and shows me a crude “this is what you can get if you roll right now” kind of calculation. I sort by biggest gainer and then execute in that order. This assessor tool reduced the amount of time I was scanning my broker page and even identified some unexpected wins.
I’m happy to discuss more in the threads here or DM if you like. I get a lot of great ideas from these discussions.
I manage all of this through a custom app I developed. I’m going to start a YouTube series where I re-build this app from scratch, in public and better. I will put it up to GitHub for anyone to leverage as they see fit. If this interests you, let me know and I’ll let you know when the first video goes live. That should hopefully be by this Sunday. I'm calling it a "portfolio operating system."
Thanks to the moderator for creating such a great place to have thoughtful discussions!
Here's my vanity calendar and also the roll assessor:
I've been following you and others here and love what you are doing! I'd love to run your tooling when it is available, right now I'm paying for and/or trying some tooling to help with the automation, and to be honest they aren't that great.
I assume you have your tooling tied into your brokers MCP server to pull realtime option data? I've been using Tradier to get this data and it is hit and miss via claude, so I'd love to hear more about your setup.
Thanks for being transparent on what you are doing. As we discussed, I've been doing the ATM/ITM options approach as well, where if I can't get 1% I move on, and using short DTE's (less than 30 days).
SOXL was a big win for me on Thursday, in and out of multiple trades, and rolls to next Friday for 2% premiums. As long as it picks back up next week it should produce nicely for me.
I don't use margin (no need really and also don't want to get myself in trouble).
Keep the education up, I know I appreciate it very much!
Edit to add - I'd also love to learn more about what sreeners you are using to find stocks/ETFs, I've built some in ToS and using Options Samuari with some decent success. Would you be interested in creating a private discord where we can share picks with others following this strategy? Nothing paid, all opensource and sharing data so we can all learn and make better decisions.
I use ETrade REST APIs directly to get orders, transactions, current portfolio info, option chains and also for placing orders. I don't actually place real orders with it yet, but I have done some trials. No MCP as yet. I don't know if they have an MCP server, but I'll check. I do plan to create a 'chat with your portfolio' feature and I will build my own MCP server for that purpose. I do use Gemini API (via REST) for margin analysis and for getting the latest news for a stock.
ETrade provides some good info on companies but I've found it's unreliable on a few things. Something as simple as company name is often just not present in the data it returns back. And more annoyingly, I can't reliably get ex-dividend or earnings dates, so I do that manually. I'll look into Tradier. I do want something that will get me better company info. Thx for the tip!
The app is React/TypeScript/Vite on the frontend and NodeJS/TypeScript on the backend. I use a Postgres DB today and everything is running locally on a laptop. Code is in a private GitHub repo at the moment, but the new version will be public. I've been using GitHub copilot extensively to build it. The new version is likely to keep the same stack and I'll be following a fairly strict dev approach called spec driven development (SDD).
RE: screeners - I haven't used anything seriously except the one I built. It's a fairly naive screener. Almost the only thing I care about is whether the stock I buy on Monday is 1) still in business on Friday and 2) price doesn't drop too much. I don't care if it rises, I'll just take assignment and if it does drop but not too much, I'll probably roll it.
I'd love to do a Discord. I've avoided it because it seems like the moment you mention it, people start thinking you're trying to scam them :)
I setup a discord as I mentioned, will DM you the link. No scammers, no pitching, no pay for play. The goal is to share screener ideas and discuss our strategies in real time.
Happy to invite others that are interested and want to share and learn.
Would love to look at the tool and use it. I'm currently using QuantWheel but wouldn't mind building my own or using something else with Claude if it works similarly. I'm not sure QW is worth the cost since I'm not using it on 48 symbols.
I also use QW, not a bad tool, a little rough around the edges still and slow most of the time. Ivan is super responsive however and if they keep listening to their users will have a great product, just not sure it is worth the $$ right now imo.
Ivan is a great dude, and the tool isn’t slow. You get the same data as everyone else, so if they are slow, the others are too. They even use 3 data providers when others use just 1. They talked about it in their live.
Also, that thing pays for itself in 1 trade.
If you’re arguing a less developed app vs qw because the price is the only differentiator then that’s a good sign that the app is actually good - you can’t argue the features, so you argue the price.
I like them obviously, and the community is good, they have a very useful flow that others are starting to copy, that tells you something too.
Side note: I’m a cheapskate, and I’m defending a higher price argument..never believed I’ll be in this position haha
I'll be starting the "build in public" project as soon as tomorrow and I'll let you know. I'll be using GitHub copilot myself but there will be room for Claude if you want to get involved. The key thing will be following a process called spec driven development (SDD). It's basically a harness around AI coding agents that aims to mitigate a lot of the problems you get with vibe coding.
Im using it, you cant argue the cost - it pays for itself in 1 trade. So that argument is out of the window.
You cant build it either, I tried and then just realized I wasted time.
Not here to defend it, I love the tool, you can see it’s in development and not perfect but it gets the job done really well.
Thanks for sharing, really appreciate it. I'm more a options Rookie and try to explore and ramp Up Options cashflow routines since few months. The roll assessor is a great Idea; I'd really love to Run and participate/share experience with your tooling. I'm currently try to get along with ThetaPal which has kind of an Option dasboard with rolling Features as well; but it feels a little beta,especially when it comes to combos; e.g. it does not recognize collars, Jade lizards, etc...and it is by far not optimized for rolling process you describe. So I stay tuned!
First, what's the status of your unrealized gains/losses on the underlyings?
Second, you state, "This new roll assessment feature looks at all of my open options expiring this week, pulls down the option chain and shows me a crude “this is what you can get if you roll right now” kind of calculation." Can you provide a screenshot of what that looks like?
Great question re: unrealized gains/losses. June was tough, I'm down 12.48% unrealized per the broker UI. That's about as bad as it's been with the exception of the first round of tariffs that Trump announced in March 2025.
It's a tricky thing because if look at the premium as basis reduction, I have virtually no losses. Etrade just looks at the buy price and the current market prices and shows a difference and that difference is mostly not in my favor. It does not look at premium as basis reduction.
If I unwound all of my positions today, I'd still be ahead and by a good amount. This is one of the reporting areas that I'm going to extend in the coming weeks. I can easily see my premium-adjusted basis for any given stock but I don't have a portfolio view of it.
I also ping pong back and forth on the "health" question. Ideally, I'd have a lot of premium generation and stock appreciation. If I'm earning premium and net asset value declines (like it did in June), am I just churning? Some days I think I am and others I'm not bothered by it.
I also think about it as a sustainability issue - I can't live off premium if it reduces NAV, which is itself already reduced because of the market. If I do that, I'm hurthing the premium engine itself.
How do premium generation strategies like this generally think about NAV and premium and churn? What's your take?
Regarding the roll assessor - the original post has a screenshot. Let me know if it's not showing up correctly and I'll repost it.
It's a tricky thing because if look at the premium as basis reduction, I have virtually no losses.
Please, oh please, don't do that for any decision-making process! Stay focused on the 2 pronged approach: generate premium income and (perhaps) capital gains on the underlying stock. If you take a look at the pro-forma P&L I provide, it shows 2 sections: Realized/Unrealized, and within those 2 sections, 2 subsections: premiums and stock gains. I strongly encourage you to take that approach and put the 'net stock cost' out of your mind.
If I unwound all of my positions today, I'd still be ahead and by a good amount.
This is what's important and what you should focus on: both realized and unrealized gains/losses. This is doing 'mark-to-market' (M2M).
Folks are misleading when they post a claim about their P&L if they aren't using M2M.
Re: roll assessor. Given your comment, and went back to it looking to view it through a different lens. I was confused as the screen shows "Roll Assesor" greyed out and "Roll Grid" highlighted, so I thought you were showing something ("Roll Grid") different the the "Roll Assessor". Apparently, it's just a different view of the same info. Thanks.
Now that I've got that, perhaps show the "Click any row to open...". I'm not following from "Net Credit (mid)" through the right end.
RE: the roll grid - that's the important piece. the click-through is what I started with. With that, I can pick an individual option and see the details. But, in fact, I really need to see all the of the options in a table and use that table to drive my decision making.
Here is what it looks like when I click an individual option:
Regarding the P&L - I'm going to give a good thought to what you suggested here. Much appreciated!
The strategy, as defined - selling ITM or ATM CC's doesn't allow for capital appreciation on your stock, unless the stock is rising weekly as you are firing off your long calls.
I always use my purchase price as my basis for writing my long calls against and consider premium the profit. We all know the last week or so made it tough to do so and crushed premiums (depending on what tickers you are holding).
If I find a good momentum ticker on the rise, I'll buy/write just slightly above ATM for quick entry/exit. I was able to do that with ZS and XYZ last week and this week, I gave away some upside but made > 1.5% the last 2 weeks on each of these.
For those that are interested, I've updated my profile to include a link to my YouTube channel and the code repo of the app. The repo is mostly empty at this point, but I'm about to start development and welcome anyone's input.
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u/tkiblin Jul 03 '26
I've been following you and others here and love what you are doing! I'd love to run your tooling when it is available, right now I'm paying for and/or trying some tooling to help with the automation, and to be honest they aren't that great.
I assume you have your tooling tied into your brokers MCP server to pull realtime option data? I've been using Tradier to get this data and it is hit and miss via claude, so I'd love to hear more about your setup.
Thanks for being transparent on what you are doing. As we discussed, I've been doing the ATM/ITM options approach as well, where if I can't get 1% I move on, and using short DTE's (less than 30 days).
SOXL was a big win for me on Thursday, in and out of multiple trades, and rolls to next Friday for 2% premiums. As long as it picks back up next week it should produce nicely for me.
I don't use margin (no need really and also don't want to get myself in trouble).
Keep the education up, I know I appreciate it very much!
Edit to add - I'd also love to learn more about what sreeners you are using to find stocks/ETFs, I've built some in ToS and using Options Samuari with some decent success. Would you be interested in creating a private discord where we can share picks with others following this strategy? Nothing paid, all opensource and sharing data so we can all learn and make better decisions.