May Investment Decisions for WillO2028

I would not call what I’ve done, from what I’ve learned this last 18 months, a pivot or even any kind of marked change. Before I sold a bunch of holdings and bought Tesla, I reviewed my monthly summaries. Maybe I didn’t learn anything more than what I’d written on July 2021.

[My Investing Principle in a nutshell Because I’m evaluating companies and not trying to figure out how other investors are valuing companies, when I’m making any investment decision, I try to accurately assess: how efficiently each company will ride the combining waves of adoption for their various market leading technologies up the hockey-stick (Hypergrowth) toward their becoming behemoths.]

I don’t see any other business model out performing, in the long-term, a Cloud native Software as an Infrastructure/Platform (of course what I mean by ‘long term’ is as subjective to my situation as my personal risk tolerance.

Since the time I began to follow Saul’s advice and the contributions from everyone here:

Year % Change
2018 +38.9%
2019 +32.9%
2020 +203%
2021 +46.8%
2022 (-)58.55%
2023 Month to Date Year to Date
January +14% +14%
February +6.45% +21.2%
March +1.55% +23.13%
April (-)14.5% +5.28%
May +31.5% +38.4%
Allocations as of 5/31/23 4/30/23 3/31/23 2/28/23 1/31/23 12/31/22
Tesla 33.11% 31.07% 30.32% 22.90% 20.48%
Snowflake 16.03% 31.64% 28.18% 25.09% 24.72% 25.83%
Cloudflare 33.8% 28.65% 27.03% 22.27% 20.90% 20.34% 16.16% 0% 5.49%
Intellia 0.91% 1.45% 1.19%
Datadog 0% 7.20% 13.27% 14.20% 16.99% 18.19%
Bill 0% 14.70%
MongoDB 0% 15.55% 16.92% 8.85%
Crowdstrike 0% 4.74%
Zscaler 0% 1.84%
SentinelOne 0% 0.03%

This portfolio is what is in my family’s non-taxable Roth and Rollover IRAs only. It contains the bulk of what we’ll live on during retirement. We have not added any money to these accounts for many years. To buy something I’ve sold something else. I don’t trade options or use any leverage. I stay fully invested at all times and keep less than 1% in cash.

This month I made 3.5 Investing Decisions:


Sold my 8% position in Datadog and moved it into cash.

I was holding the money in Datadog partly cause I might be wrong (and partly cause even if I’m right about adding LLMs to Apps is as disruptive as I believe, it may not likely occur as fast as I believe.

Snowflake may not benefit this quarter, so I’ll likely add the money taken from Datadog and add more shares of Snowflake, if share price does drop (I didn’t do this, but read below to see how doing so made sense to me at this time.). If there is a demonstrable benefit in this quarter, revealed in the Snowflake ER, then I’ll add the cash to MongoDB, where I think we’ll see another leg up there for the same reason.

AH (my 1/2 decision)

I have a difficult time sitting on cash. I bought a 1% position in, 5.5% more Cloudflare and 12% more Tesla. I bought a little Monday so I’d be motivated to get up pre-Market for the Call (I live on the West Coast).

5/15/23 reported this morning.

What I did: I sold ~30% of a 33% position in Snowflake and made my 1% position in into an ~10% position @~$147/share.

Why I did it: I saw what I needed to see. I’d like to see more details on Monday’s initiatives; but, I heard enough on Monday’s CC to back in with 2/3rds a full position.

I see the difference between what Olivier Pomel, CEO of Datadog, said at their Q1 and what Erin Zinman, CoCEO of Monday said, at their Q1 CC, as different as night and day. During Datadog’s Q1CC, Olivier Pomel’s confirmed, for me, no one knows how AI is going to disrupt. I said in a blog post here, no one knows how things are going to shake out. This was the reason why I sold Datadog.

I don’t want to be as concentrated in allocations, as I am. I definitely didn’t need to have 33% in Snowflake before their ER. I do have very high confidence in Snowflake’s growth rebounding quickly. I think their going to reach and surpass all their long term targets. But, I am concerned they may not be able to demonstrate this, not even incrementally, at their Q1ER what best represents their potential.


I Sold ~15% more Snowflake to add more to Monday. This brings Snowflake to 20% of portfolio and to~15%.

Snowflake’s share price rose substantially before earnings. I now have a place to put the money that I feel good about (see 5/15 when I did a similar trade and why). I never wanted to be so concentrated. What I’ve learned here, albeit I’ve taken this to an extreme, “when in doubt, concentrate around high conviction positions”. I think we all feel how quickly things are changing. My not knowing where things are going to shake out is at a extreme level, this not knowing being as relatively extreme as are my allocations.

I’m in for 20% before earnings for every reason I’ve learned from Saul, especially ‘not taking Macro into account’.


I quickly lost 15% of that 20% position in Snowflake.


Fortunately Snowflake share price is recovering almost as quickly as Monday share price is moving up😁.

MongoDB remains on my watch list; although, I’m still waiting for a sharp move in a positive direction in both revenue growth and further still in their profitability, before my adding them back.