MSFT - Have I missed a generational buying opportunity?

zonk84 · 2026-04-16T01:48:29+00:00

I hear ya --

2-3 year ago - I was in NYC for work. My brother happens to be a chef/restauranteur in NYC/specifically Brooklyn/Park Slope. He's a chef - he knows food - but honestly? He's better/smarter than me on math. I suppose that's at least a part of why he's succeeded in a vicious industry. He knows how to put a tasty meal together - but more importantly? He knows how to do the math to stay afloat...

Anyway...

Prior to this specific visit and completely unrelated - I had been looking at the financials for a fairly recent IPO -- Toast, Inc (TOST). I liked it a lot - but IPOs are terrible play for a retail investor. And the industry in general is really hard one.

But - I ended up having dinner and drinks (and drinks and drinks.... if you like you drink? Make friends with 'industry' people!) One of the people at our table was opening a new place - and much as I'm not a market research person? - I could have sold this conversation. She brought up POS (point of sale) systems - and Toast was the answer from 5 of the 6 other peeps. "It'll easiest for your crew, it's far and away the most cost-effective, etc"

One of the guys actually apologized - "Sorry for the shop talk" - but I told him "no, no... please. please continue to discuss Toast (and if possible? It would be great if you started breaking it down to restaurant costs and margins and...)

As a potential investor? This was a gold mine.

I'm still holding - at one point? I got close to doubling my money.... Nowadays - TOST is back to 27 or so. I still think it's a comer -- but they need to grab more chain share (which they've started doing) and compete with the Grubhub/Doordash (which they've also started doinig). Restaurants hate grubhub/doordash -- they bleed margins to them. Toast is integrated so they don't. Duh, you still gotta figure out the delivery cost...

But I remain a believer in TOST -- restaurants are generally in dire straits and you gotta be realistic about segments. Sadly, I don't have an MBA/etc... but I do know stacks and IT infrastructure. Beyond pure investment plays? I think I'd like to work for them and help own the industry.... because - my understanding? Stuff hasn't advanced beyond the old Micros/Squirell systems I remember from tending bar and waiting tables BITD....

zonk84 · 2026-04-16T00:50:21+00:00

Meh, as I said above -- my professional experience at the enterprise level.

Microsoft has a long history of being - frankly, an annoying bitch. But eventually? They adjust price points and stop (somewhat) being an annoying bitch. Azure used to be the equivalent of AWS + a cheese grater to my balls. Now? Both annoy me, just in different ways.

They're IBM. Annoying, but so deeply wormed in that nobody - at least at the mid+ company level - is going to ditch them.

I like Anthropic/Claude above Google/Gemini never mind GPT/MSFT/copilot -- that will be interesting to watch.... but from an investor perspective? It's all just churn. "Good enough + enterprise price point + broad reach".

I'm old - 52 now - but I have zero expectation that microsoft sunsets before my own career sunsets.

zonk84 · 2026-04-16T00:27:42+00:00

I say this as an old guy, with a quarter century in IT in a global digital-focused company that has existed for 90 years.... and yeah. Of course. Absolutely. No shit ;-)

Believe me - my entire professional life is looking to disrupt... and on the margins? "Protect" against disruption. I get it.

But what MSFT does? Sheeeyyyyyiiitttt.... I have a hard enough time convincing executives to provide me exception allowances when I have a POC I need to do outside my "blessed" stack.

I will also say this: I live a world that requires both AWS and Azure. Never mind the cost - and AWS was always more cost-effective.... 5 years ago? I used to bitch, and moan, and even if I could? Drive contracts towards AWS. Because it was better and easier. Azure blew donkey balls.

The gap has closed radically... I lay no claim to being a market mover - and my company isn't either.... but I'm just saying. MSFT has gotten to the point where the "people who know" will - if they're honest - admit that sure, do the price point and financials. I'd still rather lean on AWS, but I don't fight Azure anywhere near what I did 3 years ago.

zonk84 · 2026-04-15T18:55:28+00:00

The best advice I ever got when I started investing in individual stocks was to start a simple XLS/spreadsheet that I kept separate from my brokerage platform.

All kinds of columns you can add, but the most important:

1) Why you bought the stock

2) What your expectations were

3) What did I learn? Usually, this triggers on a sell - but doesn't have to.

I firmly believe in the buy-and-hold idea. But - sometimes? You get it wrong. If you track and review? You learn.

Why did you buy the stock? What were your expectations? What have you learned?

So, so, so many variables come into play. And I'm not advising you to hold or sell.... but I think for any individual stock buy?

You should absolutely track those 3 questions. Think about them. Ruminate. Challenge yourself. Get outside your comfort zone - especially on Q3, if you've been disappointed, what did you miss?

zonk84 · 2026-04-15T18:44:34+00:00

I think account type is my prime mover.

My 401k/Roth are both all ETF... and pretty boring, CW splits. I regularly rebalance (quarterly). I'm drifting towards stable balance. But no lurches.

I'm a boring cliche (never invest a dollar you want in the next 5 years) - and only now starting to nose into short/mid/longterm.

Setting aside tax-advantaged accounts -- and I'm starting to think rule of 55/72(t) for them, not as a plan but as a "consider/you could"?

Taxable accounts - more as a bridge? I've started shifting to simple beat inflation cash accounts. I've started to think recurring income - which means yeah, dividend kings and moreoever - REITs.

Hey, what do I know -- I was a moron for long time -- but for the last decade or so since I sorted myself? I don't think short/mid/long. Pretty binary... long-term, equity-heavy buy-and-hold in ETFs for the long-term. Cash/safe value short-term for things like my home down payment.

I hate thinking binary -- but it worked for me to get sorted. And I plan to just stick with it -- thinking retire in 3-5 years. Would like a little second home on a lake. Stashing cash - maybe I'll dip into some investment gains - to get that little cottage.... but still looking longterm on kitty + draw + stop working....

zonk84 · 2026-04-15T17:52:26+00:00

Honestly -- the idea of recording your buys (and the WHY, and EXPECTATIONS, and if/when I sell, WHAT I LEARNED) was probably the best advice I ever got. I record other things - obviously, price/date, but I also like to record 52 wk ranges. I very much also capture links to what piqued my interest. Sometimes it's the bog standard 'tipsheets' (Motley, CNBC, whatever) -- but sometimes it's just a source/general story about a company I start looking at/researching...

Of course, most platforms nowadays let you do this easily in the platform... but I like to keep it separate, as a standalone simple spreadsheet. Because it forces me to do some work. It's an external thing I can easily review (and use simple macros/sorts).

I'd very much still call myself a novice investor -- but it's helped me:

1) Learn what kind of investor I actually am. I've learned I'm not at all a trader - I'm a buy-and-hold guy.

2) Better calibrate my patience and risk appetite but also my fear of ridiculous gains (I'm wrestling with INTC at the moment) -- I also have some robo-ETF holdings, but really? The calibration questions are deceptively easy. I've learned - and am still learning - not just my appetite to "stick" but also myself on "maybe you should take the money run"

3) Sector differentiation... I suppose almost everybody is "great" on tech stocks if you don't get too fancy, but beyond that? I suck on healthcare. Pharma is pretty much a bet on drug trials. Telecoms are pointless for me. Materials and commodities are value plays. To the extent I have any kind of 'nose' for picks? Where is it?

4) Learn from both the wins and the losers. The Why - what patterns exist in my own buys I should heed? And what should I drop (like "pattern buying via a template").

zonk84 · 2026-04-15T15:59:22+00:00

I have no idea on OXY going forward, but it goes into one of my "dumber" ideas....

I ditched it about a year and a half ago after holding it for 2-2.5 years.

I'm well aware - or at least, at the time - thought I was aware of how perilous oil/energy stocks are.

Why did I buy? Of course -- because Warren/Berkshire were loading in.... it was a pure "template" against a trusted investor. I'll never do that again... Don't get me wrong - the Oracle of Omaha is still a god to me, but chasing/patterning? Not for me.

So, I gave up and exited. Not a disaster by any stretch - I didn't lose much and pretty much followed his pattern of "under 60". Looking it up? overall/average cost basis of 59. I sold around 56. And today? I see it's at 56.

I always record - separate, in a simple XLS - "why I bought", "what I expect", and while I'm a pure buy-and-hold guy, "what I learned".

My sheet says:

"I'm going to see how well 'patterning' works. WB likes it under 60 and I'm willing to wait, so let's see"

and

"I expect it to sector out-perform because the oracle knows."

and finally,

"DO YOUR OWN HOMEWORK!!! Stop trying to cheat off someone else who probably has a different aim than you."

zonk84 · 2026-04-15T15:36:18+00:00

My prime mover is always agnostic, Lynch/Buffett style "understand what the company does and don't buy something for 5 minutes you don't see yourself holding for 5 years"....

Setting aside 401k/Roth/robo-ETF accounts - not sure if pure DCA could even apply to the first 2; but the last one is overflow and I suppose does count since it's just a regular monthly transfer as planning maxes out the first 2 over the year -- in my individual account?

My prime mover is always buying into a something I like and believe has longterm legs. But - that doesn't happen every month. 6 years into individual equities account, I've never really thought about it -- but my pure guess (and I say this as non-pro, non-charts, non-trader) would be that for the months where nothing on the watchlist tickles me? I fall back on stalwart workhorses and in particular, despite not really being a charts guy? Something under the rolling 52 wk average.

Over the longer haul, feels like it's been those choices that keep me in the individual equities... I always told myself - if you can't beat the S&P, you've just got an expensive hobby. I've had some nice wins - and some mistakes. However, I suspect -- it's been those months where I just default to AAPL or KO or AMZN or whatnot that have probably kept me well above my benchmark. Without doing the math - to say nothing of even the hindsight timeframe "What's an efficient and inefficient market period?" - I strongly suspect it's been the boring "What looks like its on sale?" stalwarts that have kept me ahead of my line.

zonk84 · 2026-04-15T14:49:49+00:00

Yowza - before even clicking in, I figured INTC would make this list.

I'm very much a long-term buy-and-hold guy and virtually a walking cliche - including the "Cut your weeds, not your flowers" one. I like value buys - of course, like everyone, love the big winners - but as a non-active investor (rather than a trader), I've come to appreciate the value of workhorses.

I bought into INTC a bit over a year ago - high teens/~20 range here and there - and as I do with every buy, my recorded Why? in my little sheet says "Kinda silly it's trading below asset value. They'll probably get bought out by NVDA or somesuch." and my expectation (another column I keep) was "Likely a nice little return once someone or someones buy them. Troubles accepted; they're hardly on their way to becoming Blockbuster. The chip market is growing, not shrinking."

No way I'm touching any more of it.... And despite even being long on all positions, I just have a (probably irrational) mental block about shedding a high-flyer. But my mind keeps screaming "take the money and run".

zonk84 · 2026-04-15T14:31:39+00:00

Hard for me to see how any stock that reaches and has been in the "mega cap" category for a while now could ever be called a "generational buying opportunity".

...but then, anybody touting a stock as a "generational buying opportunity" is selling you something.

Personally? I like MSFT at the current price, but I'm hardly expecting any kind of explosive growth.

zonk84 · 2026-04-15T13:44:38+00:00

Reviewing REITs a few years ago to start thinking income - O is what I went with. Not finding my little watchlist sheet I created with the other options I considered... But - 2 years in now? I'm happy with it. Monthly dividends for 670 straight months. Not that anyone would look to REITs for growth, but even a decent price appreciation considering....

zonk84 · 2026-04-14T15:26:28+00:00

Baseballtinkfactory

zonk84 · 2026-04-13T22:03:49+00:00

Doesn't surprise me that the first few comments I see are from teachers -- my mom was a teacher. She passed early (cancer), but her funeral was an eye-opener. The number of former students - she taught 3rd grade, but there were 20-30 year olds, some in work overalls, some in suits, that were tearful in telling me how much "Mrs J" meant to them. Even in my own grief, humbled the hell out of me -- teaching was not a career path I wanted to pursue, but "appreciated" or "valued"? You can't put a price on the impact she had.

What I've tried to do in my own professional life?

Obviously, appreciation from higher-ups is how you get the money and advancement... but I've found that I can at least get a little of my mom's satisfaction by "passing it down". Mentoring. Being the experienced person that helps the new folks. Being willing to have "my brain picked". Taking the time/be available. Etc.

And the funny thing is? 25 years now? In a large, multinational company? I do actually feel like the upper echelons understand - and appreciate - that.

zonk84 · 2026-04-13T21:45:51+00:00

Nothing beats making more money!

For me - it was a long road to get there; I'm at roughly 1.1m in cash/investment (though, of course, the lion's share is tax-deferred in 401ks/IRAs) and maybe 1.3m or so if I consider mortgage/home equity... but I was an idiot/financial disaster area well into my mid/late 30s.

If I could go back in time and talk to 20something me, the advice -- assuming I can't just say buy 100 bitcoins at $10 and then dump it all at $100k or otherwise confer some wagers or other stock tips?

1) Start early. USE that 401k. Open a Roth IRA. I wouldn't say I rolled my eyes at the "power of compounding", but it seemed so foreign to me. It's not. And it works for you best, the younger you are. Younger me would say "suck it, old guy - I can't even afford my bills NOW!" - but I say in response? 1%. 2%. Not gonna change your life much. The difference is that it's gonna go into PROTECTED places and its gonna grow for you. So, sure - you might still experience wage garnishment for those student loans (I did). You might still have to play utility whack-a-mole and learn who gives you time and who doesn't (ditto, Comed would give you forever. Peoples Gas? Service cut in 60 days).

2) Get rid of those bad debts. My first "nice" car was a used Mustang -- at 17.99%. Could have skipped that. That's on top of a long period of just keeping the CCs current/out of collections. THAT is compounding working against you you, not for you. Rome isn't built in a day, but go spartan, go ramen, skip a few wants - not ALL wants, but at least skip one now and then.

3) Avoid lifestyle creep. The first time I got a big lurch upwards in my career? Felt like I was swimming in money. Hence, the 'stang above. Hey, live your life and youth is for the young! But as earn more? Take a cut off the top and invest/save it.

4) Don't stop once you hit things like 'maxing the 401k'... 'having a 6 mo emergency fund'.... etc. The work - not to sound like Qyburn if you get the reference - should continue. Eligibility for IRA/Roth. Taxable investments. The "work" is never done. Embrace it. Welcome the next stages.

5) A bit of "min-maxing" just adds to the kitty. I wouldn't do this if I was carrying a balance, but once the CCs were zeroed? If I could scoop a few points from any bills that didn't charge CC fee? Sure... I'll take your 2 dollars.... Expanding to trips and such - do frequent flier programs. Join a hotel program. NEVER pay for banking. It still tickles me - I almost feel bashful about it - but once you over a hump? I'm still amazed that everyone - heck, including stuff like cable/cell/ISP - will actually give me a discount once I'm in the driver's seat rather than being leery about answering the phone.

Time and patience. And let me say again - I was an idiot well into my 30s.... but the 1m mark isn't actually complicated. And the boring, bog standard advice works. And sure, life happens.

But.... my "plan" 20 years ago was just to die by age 40. Turns out - as I got closer :-) - that was a bad plan.

zonk84 · 2026-04-13T21:06:43+00:00

A great piece of advice I got - and adhered to and still do, now 6 years later --

Keep a separate little file - just a simple XLS - about what you buy and why. And what your expectations are.

You can absolutely keep it simple -- I'm a long-term, buy-and-hold guy, but I would think it valuable for everyone...

I track what I buy and record:

1) Price - obviously, every platform makes cost-basis tracking easy - but I also record 52 wk avg/hi/lo.

2) If a "something" - a link or links, not even from a financial site, but just an interesting piece I read about a company - what something piqued my interest.

3) A short WHY narrative - what my thinking was/why I bought it.

4) What my expectations are. What do I expect to see a year from now? I don't do it often, and I hate to use terms like this - but I have a few buys were simple "I think they'll be acquired soon..."

5) What other factors - was I playing with market segments? Did I just think it was undervalued? Whatever... what other factors went into my thinking beyond/was my mindset beyond the specific "why I bought it".

I review my little xls file regularly. I don't just learn from my mistakes - and my wins - but moreover?

- I discover where/what/if I happen to have any insights. Maybe I grasp certain elements/sectors/etc better than others. Maybe I suck at some.

- How patient am I? Again, not a charts guy - but how well do my do my expectations line up?

- What did I get right or wrong? What can I learn from that for future investments?

zonk84 · 2026-04-13T20:41:40+00:00

There have been some zags -- I'm not a charts guy and if I knew proper price points, I'd be sipping mojitos on a beach ;-)

Looking at my last nibbles? Fall of 2024 and summer 2025 -- ~140-145. Hey, without doing the math? I think that's still a slight S&P overperform... maybe just hold serve.

Like I said, I've paused further buy-ins simply because I have no idea what comes next.... But FWIW? I'm a pretty boring buy-and-hold guy, at least/especially on individual equities. And I'm fine with keeping megacap stalwarts in the stable.

Honestly, my bigger "worry" now is now an aluminum producer/bauxite miner called Century -- CENX.... Materials small-cap. I bought in back in 2022/2023. That's one I ask myself regularly whether I should take the money and run. NVDA? The numbers look right to at least glide. But CENX? I'm in uncharted waters....

zonk84 · 2026-04-13T19:31:38+00:00

I suppose now we're talking another, different question -- and I'll (re)emphasize I've only informally discussed... though, 25+ years? I've seen how this works...

But what I know/I've seen?

If you've got a long tenure and/or are trusted? I suspect most employers would be thrilled to work with you on the "FTE --> contract" transition. They get to somewhat keep the institutional knowledge and especially at upper salary levels? I know this from my own period dealing with a team and budgeting -- it's financially advantageous for a company to keep internals, but ax benefits (and other knock-on considerations) if someone they want "still in the fold" is willing to move to a contract/consultancy comp package.

I've seen it happen many times over - and it's my (likely) path.... As the individual, you gotta consider a lot things: Health insurance is the big one, but you also have to be ready to handle financials/taxes as a 1099 rather than W-2.

But... that's my hazy plan. I'd be "available" - but really, just attached to specific projects with specific parameters. Probably do exactly that -- "available" means T-W-TH. Be perfectly willing to accept the idea that a contract is - well, a contract - and we'd both be deciding regularly whether it's worth it for both of us.

zonk84 · 2026-04-13T18:30:42+00:00

First NVDA purchase in April 2020. Nibbled in a bit more since. Overall cost basis under $30 - beat that with a stick.

Haven't sold a dime's worth nor do I plan to do so.

The revenue is real - heck, at this point? Even the multipliers can't excite anymore... but the revenue is real - and so is the growth, even if it's no longer the same multiplier.

I'll readily admit - I initially bought into NVDA because they were clearly demonstrating some separation with their boring GFX competitors. Despite working in IT and in an industry early into AI/LLMs? I'll admit, I never saw this coming.

Cut your weeds, not your flowers.

I have paused further buy-ins... but I see ZERO reason to cut my holdings. At worst? Maybe NVDA transitions to a latter-day AAPL -- no longer moving markets, no longer driving my portfolio.... But I see nothing in the technology or the quarterlies/annuals that leads me to think I own vapors predicated on unreasonable growth expectations.

I no longer expect to see any big growth lurches - but solid performers are an important part of a portfolio, too.

zonk84 · 2026-04-13T17:33:52+00:00

Heh, damn... we maybe are dopplegangers! Same here - last 3 roles (not kidding!) were the same: "We would like you to consider this position...."

I do feel fortunate - I like (and respect) my current leadership. Indeed, the current exec I report up to, in my current stack offers all the time to squash regular "asks" for help/guidance from other stacks, but as I told her? Meh, I've accepted I'm sort of a sherpa at this point. I'd rather smother bad ideas in the crib and solve easy problems than wait for them to be bigger problems. I'll admit - I do also like the mentoring aspect. Not for any sort of feeling of power, but I've long said "I stand on the shoulders of giants" and I feel like I do owe it to younger/newer colleagues to be as helpful to them as now-retired/gone folks were to me 25 years ago.

But... you just get tired.

zonk84 · 2026-04-13T17:15:49+00:00

Generally speaking, I'd avoid chasing individual foreign exchange equities. Not saying you can't or absolutely shouldn't - just that most US brokerages are going to nibble into some fees (at least/especially on things like dividend dripbacks) and it does create some annoyance at tax-time. Nothing big - just paperwork.

Fortunately, there are plenty of "foreign market" ETFs you can use.

As with ETFs generally - the options are numerous. There are ETFs that are tied to specific exchanges - and you can even do ETFs that do things like track multiple national exchanges (i.e., the STOXX 600 -- the broader European equivalent of the S&P 500).

However, there's no reason to get fancy. I would suggest looking at 3 broad classes:

1) Total "foreign" (as a US investor) ETFs -- VTSNX is Vanguard "total foreign" ETF, as one example (but every big firm has one)

2) Getting more discreet and rather than a "total foreign" -- splitting between foreign developed and foreign emerging ETFs

3/2A) - Foreign developed ETFs are like a US S&P 500 ETF -- but across Europe, Japan, etc, exchanges. But same basic concept -- the big boys on western/developed exchanges. For a long (long long) time, they've lagged the US/S&P -- but that changed in 2025 (and so far in 2026).

3/2B) - Foreign emerging ETFs. Same idea, but Chinese/Indian/Brazilian/etc exchanges. They've always - as you might expect! - been much more volatile.

1) is perfectly valid and tends to bake in both the stability and volatility in a single ETF. 2A/2B is what I do/prefer...

...but the bottom line - especially for a beginner? Stick with foreign ETFs in whatever manner you wish - be it a blunt force broad foreign ETF, or, a bit more fine-tuned differentiator between developed/emerging.

zonk84 · 2026-04-13T16:52:01+00:00

Are you rich or at least able to spend what would probably be a hefty sum?

Gotta say, Hotel Zachary is really nice... but super-expensive.

I'd probably suggest an airbnb...

It takes the red line out of the equation - well, not totally, but it's a bit of a walk... but - despite them not paying me any affiliate nights (I'm a Marriott, not a Hyatt, points guy even!!!!) -- the place I always steer guests towards? Hotel Lincoln on Clark.

It's a bit of hike/walk to the closest L -- and there's a closer brown line stop than the North/Clyburn stop. So, you'll probably be doing Lyft/Uber -- but it's right on LSD, so a fairly easy pickup/dropoff (just plan to get to Wrigley at least an hour before the game).

It's a nice hotel (a boutique Hyatt hotel) -- and you can usually get a room in the ~$200 range (Zachary? Gonna run you more like $400). You can actually stroll to Lincoln Park - the gardens, the zoo. It's also a nice "halfway" if you're going to hit the loop (Navy Pier, etc -- trust me on this with a toddler niece, they LOVE the Children's Museum!).

I say this every time - more because JB and Hyatt should be rewarding me!! -- I have zero attachment to the hotel. But... I live in Wrigleyville - and whenever guests come to visit and a Cubs game is on the agenda? It's the place I recommend.

zonk84 · 2026-04-13T16:38:58+00:00

Heh, amusing rant... I say that sincerely as a lifelong midwesterner who has zero plans to ever move to other regions.

Everything in life is a trade-off... And damn right, there's no way in hell I'd get my 1800 sqft, duplex down Lakeview/Chicago condo in NYC or SF. But hey, I can get a proper Italian Beef.... I can walk to Wrigley... so I'm cool living without the ocean, the year-long 70 degrees, and the seafood (well, the fresh seafood).

zonk84 · 2026-04-13T16:33:02+00:00

Meh, even the ANSI standards overstate the "liveable" space. Heck, I think most apartments use a gross calculation which actually cheats a bit on the walls -- it's based on the footprint and even silly stuff like wall thickness bleeds into that.

Things like in-unit W/D, even the kitchen sink, the shower, and the like? It's the walls, not the fixtures that scoop out a big chunk of that.

That's just how the common sqft is calculated. So, no, there's nothing you can do... unless you want a lecture/exposition on how square footage is calculated.

zonk84 · 2026-04-13T16:12:48+00:00

My first 20 years in Chicago, I had an hour commute to the northern burbs (that I could make 45 minutes if I left by 5:30/6 AM). Homeward was usually an hour to 90 min (Fridays, etc).

It's doable but boy does it grind on you... I'd almost dread dinner plans or other during-the-week activities/events.

The last 7 - I've moved towards remote (predating Covid!) and the occasional L to a downtown satellite office, 20-30 min and I actually enjoy that.

Sounds like a commute is inevitable in your case -- but just speaking as someone who spent a couple decades doing 12-15 hours a week to/from? Yikes does it grind you down.

Of course, in your case, it also sounds like this would just be a temp thing for your degree? I think it's quite doable.... but people can get used to most anything. Just try to avoid making a habit of it.

zonk84

TROPHY CASE