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MORE OR LESS with Bing Gordon — haven’t listened yet, but Brit and Dave had Bing talk about life, Silicon Valley, and his new book… Bing is the best — a truly wise man — so different vibe to this one, I am sure, but in a refreshing way :) … Jess did listen and her takeaway is “hey, maybe we should have more planning, structure, wisdom in MOL vs. just yell about the news” (nah).
HOT TAKES
Any firm not scaling their security spend at the same rate as their AI spend is missing the moment — the attack surface is growing exactly as fast as the capability surface… nobody budgets that way yet… but the hacks only pick up more and more. Also, NYC consensus is clear: bank with JPM, because for bank hacks you want correlation with everyone else, not to be the only guy with assets in your regional bank.
High-Agency People are Pro-West, Low Agency People are Not — most interesting idea I heard this week… the whole “pro-West” vs. non-pro-West thing is really a divide between people who feel personal agency (or believe in it) and those who don’t — who look at their own agency as belonging to big, brotherly governments and institutions that feel like saviors, beyond them, out of their control. This vibes for me directionally, and hits my instinct that I really only want to work with people who are pro-West… and maybe that’s just political shorthand for people who are high-agency and feel — or aspire to — a sense of empowerment.
Speaking of agency… Study the Agents of Hollywood to Understand the Future of Consumer AI Agents — Ari Emanuel’s “Roll the Calls” — worth reading the whole thread, and the book. Everyone is building “agents” right now and almost no one has studied the people who actually made a living being one… and the answer? The whole asset IS trust in the individual… and the business is doing whatever it takes for the “client”… nothing specialized, all commodity, just leveraging the trust clients place in you, which opens doors differentially. Not the financially best business in the world — constant threat of being fired, sending gifts, etc. — no real “asset” base, certainly no monopoly…
Price OR Quantity in the K-Shaped Business Realities — I’m pretty obsessed with studying (and investing in) what the economy looks like as it gets more K-shaped, more unequal — and it is way easier to get dollars from rich people than from poor people. One framework / quip… do PRICE or QUANTITY (not both) — there are high-price, low-quantity strategies, and low-price, high-quantity strategies — but only death in the middle.
The Slow AGMs were Fish, Lumber, and Parking — I’ll share some sanitized slides and insights maybe next week when I have better-than-airplane wifi, but the net of it:
This creator strategy is working, and it just keeps getting better as AI commodifies everything else — trusted cults/communities are the only way to advertise, structurally low CAC in high-spend verticals rules, and AI is commodifying all the crappy parts that used to get in the way.
The way to make money on AI is to own the scarce assets and buy the increasingly commodified tech in… incumbents win… but just like oil field development, you need the asset prices you’re buying to fix with AI to not already reflect the AI bump — otherwise AI potential becomes a liability, not an asset.
My line on AI has been “long the alpha, short (neutral) the beta” — which I still believe. There are good point opportunities, and the overall thing is cray-town pricing-wise, but as a very wise friend said to me a few weeks ago, most LPs say they want ALPHA, but what they really want is BETA… and of course, when BETA goes bad it drags your alpha down with it. That all said, looking back over the last decade — starting with seeds in Otter.ai, Metropolis, Assembly.ai, Kepler, etc., through to our pivot to “own the assets” with AI tailwinds — I feel good that we’ve been consistently ahead of the narrative, and in winners :) more to come.
It always makes me nervous when funds you are invested in send gifts that are too nice — still true a week later, the bags keep coming… when the calculus, even on the margin, is “but they give such nice stuff,” something is off.
Only 250 people on earth spend $10M+ on AI — wild stat, and the Anthropic bull case succinctly put… it doesn’t matter if margins come down / are thin, basically no one is actually using AI yet, and everyone will. The TAM argument isn’t about share — it’s about the fact that the market barely exists.
We have the second coolest VC website… — this might be my finest work… a while ago a partner of mine proposed we have a different website, one that looked like every other website. I made it clear to them that the proposal itself showed they deeply didn’t understand our firm, and perhaps meant it wasn’t the right home for them. Message received — and now deeply validated by someone I don’t even know on the internet…
Best,
Sam
P.S. an ode / some thoughts on the New York Marathon… this was actually the point of my week… what a special experience. This was my 3rd real marathon (I ran one 22 years ago, effectively drunk, on a dare that doesn’t count)… it’s a pretty emotional experience, and I get why New York is considered so special by runners. A few reflections:
Can you imagine what an ancient battle was like? 60,000 people in a stadium is one thing, but when you experience running with 60,000 other humans out of “camp” (the start area) through New York… it’s mind-boggling to think about how it felt a few hundred years ago, with swords. Humanity just pouring and pouring through the streets, intersecting at twists and turns through Brooklyn. It’s an experience.
New York at its finest (don’t mess with NYC). Going through all five boroughs, the mass of New York humanity… everyone cheering, the sound deafening. So much humanity — clearly so many communities and stories, but all united… it makes New York feel powerful in the most uplifting way. It feels awesome.
People are shockingly fit — like, really fit. The marathon, it sounds like, has demographically shifted younger and is now a Gen-Z affair, and the cultural shift from bars to run clubs shows it. There are a lot of strong people out there… not just the guy who came out of nowhere to win in his first marathon ever (though the American who won Chicago this year, training almost exclusively at Planet Fitness on shitty treadmills, is an even better story — what a moment for running).
Solitary pain in a sea of humanity — I almost never run with anyone, always alone… the only marathons I’ve run have been in the desert, alone. To me the whole experience is a private conversation — so much so that, despite lots of friends cheering and sending pics along the way (thank you), I only spotted one of them (and missed my wife in the crowd several times). It’s particularly interesting to be in a sea of humanity and alone and in pain — there’s something very interesting in experiencing deep aloneness — it’s just you, in a sea of millions of people.
Again? As always, the last several miles are a conversation in pain, and you are never doing it again. And then a day later — because this stuff is chemically addicting — the question is… should I train all year and see what I could actually do? That’s the loop… Congrats to all the many friends who ran, and thank you to all the friends out there yelling and supporting (even if I didn’t recognize any of you, except Will Rubin… lol. Hi Will…).
Thank you in particular to Roberto (the best coach — I can’t believe you ran 7 marathons last month, in 7 days), Casey — a great friend, Mr. NYC Marathon, and the entire reason I’ve done any marathons at all — and Randi, who is the only reason I did this one this year.
SWL
P.P.S. this is interesting… purchase beats promise because it binds the adversary’s own law; the plain-sense reading says purchase is what the powerless do, and overpaying advertises weakness.
P.P.P.S. Also — is any trigger you bind yourself to in advance abdicated judgment dressed up as process, or does Ra’avad’s distinction — the sign must be evidence about the trait itself — actually hold?
sam lessin | @lessin