SWL Week in Review - Space Bet, Softbank, and Bill Maher

From:

Sam Lessin <sam@wlessin.com>

To:

Hidden Recipient <hidden@emailshot.io>

Date:

3/17/2025, 2:14 AM

More or Less: Betting on Space (Literally)
In which Brit and Sam make a $1M bet about whether a human will have set foot on the surface of Mars by 2040 (guess which side of the bet I am on)… and I say that as someone who invested in SpaceX, thinks that is the good Elon company — so, one way to read this? Brit just funded a nice hedge for me on my SpaceX position :), even when grok is the only LLM that gives it a >50% chance

Hot Takes:

When SoftBank Buys, You Sell... — people seemed to think this was funny — beyond the public commentary, I got more than a few emails from well known MCs saying ‘lol, I say this in private but was laughing at you saying it in public’ — been saying this for while, but seems like I finally got the right meme-able verbiage and venue to make people care at least a bit…

The Information / Elon Grok Tiff on Bill Maher - a few weeks ago Elon screenshotted unreleased Grok3 being all snarky about the information and saying ‘just trust twitter’ — of course when launched and tested Grok3 is nothing but respect for The Information — but it was funny to see this make it all the way on to Bill Maher as a ‘lol look at this ridiculous farce of unbiased elon/grok’ — regardless of what you think of that point, it was funny.

Mr. Beast .. Not Worth $5B, and Not Going Public Anytime Soon One, we are in a world where private investors with liquidation presence and a dream are willing to pay more than the public market. Two, every creator is terrified of losing money for people that invest in ‘them’ directly (it is a huge asymmetric risk to the downside for them!)… that is why beast isn’t going public even if he says (and thinks) he is anytime soon — Musk - the ultimate influencer - has actually done this right by (a) making the public thing not his name and (b) making number go up (loyalty from make rich / roman general style) — that is, until the last few weeks!

Trump Make Poor? People like Trump make rich… but now, Trump make poor? … I think I speak for many when I say I like ‘make rich’ better… I just hope they aren’t basing their strategy for the economy on the famous Top Gun Strategy of I'm gonna hit the brakes, he'll fly right by — (would be sweet if it works tho and debt gets reset, AI hits at just the right minute after tightening, etc.)

Jessica’s Lessin Media Co’s Racket Investment last weekend at Indian Wells (shhh don’t tell everyone it is the best tennis tournament) Jess announced Lessin Media’s investment in Racket — which is a great publication, and particularly a fun investment if you happen to like tennis …

The donations that end up in unintended places…. This is bad — big problem with non-profits IMHO is where the money actually ends up / what you end up funding… If you give philanthropy as an individual or as a government it is critical that you have as much KYC on what you are funding as if you are an investment company / investing — blood is on your hands if you unwittingly fund the bad guys.

Debating AI with Seth (via Billboards of Course). This ended up on the Tech Brothers podcast (which really is fun) — of course, I think I won our debate … because, it is me…. But TBH I feel like my main points on ‘AI investing is stupid’ have gone so mainstream in the last 24 months that they are becoming boring to me — big platforms win / even things like OpenAI are massively sub-scale to compete at the big boys table… and yes small companies that can use AI as pure leverage also win — but companies that brand themselves as ‘AI’ primarily are suckers bets. Said differently — AI - never be in the middle

SaaS — Just Not That Great a Business Model — this is honestly more of a Will Quist rant than a Sam Lessin one (will always give credit) but one I deeply agree with — SaaS really is a shit model vs. the good old days of enterprise software sales where you got paid upfront and for years by your customers to build the product. Now with AI, we are gonna replay these games of the difference between what is good tech and what is a good business / business model (and you really should care about the later)

On the slow creator fund — if you are reading my newsletters you are probably bored of this topic … but here is another articulation of what we are up to and why you should care :)

Jelly-my-Jelly Tipping & Run — guys, this thing actually is happening — Iqram still needs a few killer engineers — but new media format + bringing back a modern Venmo style social payments feed with crypto / ranking by token holding, etc. is pretty sweet / been very fun to play with …

CAC always goes up (not down) Stop telling investors that your CAC is going to do gown - this drives me nuts. It isn’t true

Google Maps is Broke(n) — also driving me nuts (literally) — how did google maps stop working and no one is talking about it / I legitimately feel gaslit…. Good example of how LLMs / AI chatbots going rouge is gonna feel…. Which is why we need AI model editor on top?

Twitter’s Major Innovation is being Pro-Bot— and finally speaking of AI and bots — For a while now I have been saying that the future of social networks is that rather than asking ‘who do you want to follow’ they will ask ‘who do you want to follow you’ — we are running out of humans/ there already aren’t enough to provide every man woman and child with the social validation they so desperately crave… IMHO this is the most obvious AI use case, and honestly by letting bots run amok / treating them like a benefit rather than a cost twitter is just killing it right now.

Sam Lessin

P.S. my personal quote of the week was from Peter Deng…. Who is 6 weeks in to his career as a venture capitalist (congrats Peter on the new role!)… the line “Venture Capital is the Light Side of the Business” — lol, that might be the first time anyone has ever said that…

P.P.S. In Miami for 10 hours tomorrow — I got a Barry’s Bootcamp off the redeye to survive and a panel… where do I get ice cream in Miami Beach (or better yet anyone got some kites and a board I can borrow for an hour to make it a real strike mission??)

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