SWL Week in Review - Positivity?

From:

sam lessin <s@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

1/9/2026, 8:28 PM

More or Less - A Touch Of Optimism?

Thanks to all the folks who felt necessary to message back about my downer email last week… all the media people were like ‘yah this sounds right’ and all the investors were like ‘stop being a bummer’ for what that is worth… this weeks MOL / week 1 of 2026 we are back on a more balanced mix discussing the K shaped world we live in, where mega IPOs are gonna make a bunch of people rich while young people have no job prospects, software is commodity, and no jobs! … but I guess BLE lego is cool?

Hot Takes

Dark Forest or Shock and Awe… Pick One Strategy … this came up in several of my first meetings of the year… lots of people are making lots of money with smart ideas where they don’t want to tell anyone / stay hidden (because the incantation / secret IS the value — if people know about it with AI software development it is too easy to build and get competed to zero quick)… lots of people are going for broke on thesis that everyone knows and excepts and it is just a matter of wild spending brinksmanship — who can be crazier… either be crazy or be quiet. Don’t be in the middle.

Riffing on the Year Ahead… if you are on this newsletter you probably already saw my downer note on the year ahead… but here is a little freestyle video on it for the illiterate who may be lurking… also if you care more about business, here are the AI questions of the year… to be clear, as a technological determinist — we don’t have much control on any of this tho / so just enjoy the ride since all of society / culture is just downstream of tech / what is technically possible

Should the Billionaires Team Up Against The Trillionaires? — Since California and New York are flirting with confection (you idiots)… here is my attempt to get canceled on the week. If Elon is gonna be a trillionaire that is a THOUSAND billions (math)… there are according to ChatGPT only 900 American billionaires (btw, that is massively low but whatever) — that means ONE Elon could technically pre-tax DOUBLE the number of American billionaires if you confiscated his wealth! Should the billionaires team up against the trillionaires?! Is that were we are going?

Speaking of Which, The Miami Housing Hedge — this went strangely viral … California tech founders were in the news this week for big Miami home purchases… kinda like Goldman’s Jersey City unoccupied building hedge in 2006? (I remember when it was shocking a company would be so rich and smart as to hold 60% of a building unoccupied just in case

Advice for Kids — don’t be an accountant or dental hygienist — learn grit, optimism, self respect… you will be fine. Learn how to learn fast, fail fast, get back up (and ideally be a good human?)

More Cult Leaders Less Beast — on TITV this week… I also did some CNBC but I can’t find the clips?! Is that on me or on them?

More Money in Politics Please — it is always a pet peeve of mine that folks get this so deeply wrong… also now do you understand why rich people buy newspapers and build big personal followings?

X.AI and X NSFW scandal - wait, are you telling me that AI image generation is for porn? The shock! But seriously, this is the liability of both owning the distribution AND the content generation vs. being a passive proxy…. Oh and here is why the AI girlfriends will win even if they are clearly bad for you (and bad for the world)

Elizabeth Holmes Now Follows Me On Twitter, From Jail? — this was an interesting follow to be notified of. I do think SBF, Liz, etc. would have a pretty differentiated approach to venture & certainly have the brand recognition — especially with anthropic at $350B

Clawdbot — HT to MSG… this is pretty good… and hilarious that when you open it it tells you how many ‘packages’ are looking for funding — if there was an automated VC of the future, this is how it will happen.

Best
Sam ¶

P.S. Landman.

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