Convenience‑Store Takeovers & AI’s Next Frontier
Issue #2 | Margin of Signal: June 15, 2025
A weekly curation of the highest-quality content across investing, business, tech, and AI.
Happy Sunday (and Father’s Day to those who celebrate)!
Sure, algorithms crunch numbers at hyperspeed, but real‑world scale still runs on sushi‑grade sourcing and CFO sign‑offs.
This week, we explore how retail’s biggest bids and AI’s talent tug‑of‑war remind us that people and processes still reign supreme.
Without further ado, let’s jump into this week’s picks.
Bill Gurley's Tech & Venture Deep Dive
Take it from Bill Gurley himself:
If you care about the state of high tech investing circa 2025, you may find this interesting. I cover all constituents - founders, VCs, LPs, ordinary investors, regulators, bankers. Something for all.
I learn so much every time I listen to Gurley speak. He walks us through today’s fundraising rounds, emerging regulatory headaches, and why you’d better have more than just a good pitch deck.
This was a masterclass in the reality checks that Silicon Valley doesn't want you to hear, but desperately needs to.
Why There’s a Billion‑Dollar Battle to Own 7‑Eleven (Bloomberg Originals)
Japanese 7-Eleven: fresh sushi at midnight, supply chain choreography that would shame Amazon, and profit margins that defy convenience store physics.
American 7-Eleven: fossilized hot dogs under fluorescent purgatory, broken Slurpee machines as permanent fixtures, and checkout experiences that make airport security feel streamlined.
Couche-Tard's audacious bid for Seven & i Holdings isn't just a corporate play; it's a bet on bottling Japan's "magical" 7-Eleven experience—think fresh bento and a Harvard-studied supply chain—to rescue its struggling US cousin.
As an American, Japanese konbinis are truly an ethereal experience (FamilyMart FTW). I can't wait to go back—and neither can deep-pocketed global dealmakers.
Journalistic excellence from Bloomberg:
Anthropic's Product Playbook: The Instagram Co-Founder's AI Pivot 🤖
This was a fascinating listen.
Mike Krieger (Anthropic CPO & ex‑Instagram cofounder) opens up about life inside a frontier AI lab where the operational playbook reads like tomorrow's business case study.
Anthropic now writes 90% of Claude's code with AI, shifting bottlenecks from engineering to decision-making.
Even more intriguing: Claude Opus 4 has evolved into Krieger's intellectual sparring partner, not just sophisticated autocomplete. He deploys it to challenge assumptions and stress-test ideas, essentially turning AI into his strategic counterpart with infinite patience and zero corporate politics.
Then there's the Artifact app postmortem. Krieger's decision to kill the beloved app reveals how revolutionary AI experiences crash into the brick wall of iOS limitations and stubborn user habits.
If you only listen to one AI interview this month, make it this.
Relatedly, the AI talent war is heating up.
Top AI researchers now command pay packages that make NBA max contracts look quaint. We're talking LeBron-level money, folks.
Enterprise AI's Reality Check: Why Your Fortune 500 Isn't Going Full Skynet
Stochastic models meet deterministic corporate processes, and guess who wins? Spoiler, it's not the LLMs.
CFOs don't want magic; they want audit trails that won't embarrass them during the next compliance review. A reality check on why enterprise AI adoption looks more like cautious tiptoeing than revolutionary sprinting.
Dave Friedman delivers a two‑parter on corporate inertia:
Part I: Legacy systems, procurement cycles, siloed data, and why no CIO is rushing to rip & replace.
Part II: The three hidden blockers — talent, trust, and total cost of ownership — that even the nicest demo can’t overcome.
Trump 2.0's Economic Playbook: The Three-Legged Stool Returns (Citrini Research)
Citrini Research dissects the inevitable trade war pause and why the "big beautiful bill" might fuel equities this time around.
In the second half of the interview, he talks robotics as the next secular mega-trend, with China already lapping us in the automation Olympics.
While we were arguing about TikTok, they were building the future workforce. Classic.
a16z's AI Revenue Reckoning: When Yesterday's Unicorns Look Like Ponies
The VC industry loves its growth mythology, but a16z just dropped the receipts that make pre-AI "rocketship" startups look endearingly primitive.
Their data across hundreds of companies reveals a brutal new reality: median enterprise AI companies are hitting $2M ARR in year one, while consumer AI ventures are clocking $4.2M—numbers that would have made Sand Hill Road weep with joy in 2019.
What we once called "best-in-class" ($1M ARR in 12 months) now barely qualifies as "participated in the economy."
Speed isn't just a competitive advantage anymore. It's table stakes for survival.
Translation for the non-Silicon Valley mortals: if your startup isn't growing like it's powered by rocket fuel and existential dread, you're already behind the curve that's reshaping the entire software universe.
I think the jury’s still out on most of these AI darlings. While explosive topline growth is cool, high net revenue retention and low churn are even cooler.
I also think it’s fair to question how upstarts are calculating ARR. Given their private status and cutthroat competition, these startups are practically begging their CFOs to get creative with the calculator.
The question keeping AI investors awake at night: in a world where competitive advantages can be commoditized faster than you can say "ChatGPT wrapper," what constitutes a defensible moat beyond sheer execution speed and prayer?
Kalshi's AI Ad Gambit: Network TV Meets Google Veo
A prediction market company just aired an AI-generated NBA Finals commercial for pennies on the dollar compared to traditional six-figure creative campaigns.
Google's Veo engine handled the heavy lifting while Kalshi handled the audacity.
This isn't just about cheaper ads—it's about brands going viral-first, budget-second.
AI democratizes high-quality creative production to such an extent that the limiting factor shifts from "can we afford to make this?" to "will this actually capture attention?" Brands can now afford to take bigger creative swings because the cost of failure is so much lower.
When a betting app can produce broadcast-quality content faster than traditional agencies can schedule their first brainstorming session, the entire creative ecosystem needs to reassess its value proposition.
Side note: Go Pacers, fuck OKC. (As a Seattle native, I’m praying on the Thunder’s downfall.)
Shouts to ChatGPT and Claude for research and editing help.
That’s it for this week. We’ll be back in your inbox next Sunday with another Margin of Signal.
Thanks for reading,
Chima
I always listin when Bill Gurley speaks, you know the man has seen some shit in his career.
As always I'm fascinated, but better than that is that I learned a ton. AI in advertising? Who knew? Thanks for staying on top of this shit so we can too.