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@Paul_Gravette
Entrepreneur ($3+ billion in sales from personally owned companies) | Private Equity | Family Office | Philanthropy
What matters today
Money, health, time back, everyday tech, travel and family. Picked by Paul.
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Our fave Halloween outfit! Have fun and be safe friends!
Tell us yours on XElon Musk interview this Tuesday
Cover art: The Builders with Walter Isaacson / Kaleidoscope & iHeartPodcasts
A must-listen: Walter Isaacson sits down with Elon Musk for the premiere of The Builders with Walter Isaacson.
Listen live with us. We’ll be tuning in when it’s out and sharing what stood out to us.
Tuesday, Oct 20
Via Axios, Oct 17.
AI agents can now pay.
Stripe headquarters, San Francisco, 2019. Photo: HaeB / Wikimedia Commons, CC BY-SA 4.0.
This week, AI agents took a real step from helping you shop to finishing the purchase. On Oct 15, a16z put the spotlight on what fintech veteran Terry Angelos calls “the Wallet Wars”: the race to give AI agents a safe way to pay. The idea is simple. Your card stays in a trusted wallet, and your agent gets a stand-in number that works only at one store, within limits you set.
The evidence is showing up at real companies. Stripe’s president, John Collison, said agentic commerce activity at Stripe “basically started going vertical” in September. The same day as a16z’s posts, Mercury let its customers ask popular AI assistants to pay a recipient or move money, with nothing sent until a person approves it. The wallets racing to connect to agents are already large. By a16z’s count, Stripe’s Link has 300M users, Shopify’s Shop Pay 250M and PayPal 400M+.
Photo: Epolk / Wikimedia Commons, CC BY-SA 4.0.
This fits one of our Predictions: the winners will be the people who ship finished work with AI, not the ones who just “know AI.” An agent that can pay closes the loop on the task. It also points to a bigger shift: AI is becoming a new front door. We think more customers will arrive through an agent that compares, decides and checks out for them, not through a home page.
What it means for you: start small and stay in control. Let an assistant prepare one routine purchase or payment, and keep the final approval for yourself. If you sell anything online, ask whether an agent could find your offer and check out cleanly. That is quickly becoming the new storefront.
Via Payments Dive, Oct 15; a16z on X (how agents pay and wallet user counts), Oct 15; and Mercury release notes, Oct 15.
Bet update: Anthropic now hires for judgment and ownership.
Image: Anthropic
Anthropic published a study of its own workforce on Oct 16, and the finding is telling. As AI agents took on more of the coding and routine work, hiring managers shifted toward judgment and autonomy, the ability to work independently, and away from narrow technical expertise.
Day to day, the work itself changed. Staff spend more of their time directing and reviewing what AI agents produce, and TechCrunch’s Oct 17 coverage notes that the workforce has become less junior and is spending more time in meetings.
Photo: Vitaly Gariev / Unsplash
That lines up with one of our standing predictions: “knows AI” stops being a differentiator, and shipping finished work with AI becomes the job. The scarce skill is deciding what good looks like and getting it out the door.
For builders and operators, the takeaway is practical. Pair deep experience with AI and own the outcome end to end. That’s the profile Anthropic, a company at the frontier of AI adoption, says it now hires for.
Via Anthropic, Oct 16. Also covered by TechCrunch, Oct 17.
Our bet: Nvidia is still the company the AI world runs on come October 31.
Chips had a noisy week. The bigger picture hasn’t changed: the world is still lining up for AI computing, and Nvidia keeps building the chips behind it.
That’s the trend we’re watching. More companies putting AI to work means more demand for the hardware underneath, and a trend like that doesn’t turn on one shaky week.
Our readLikely. One loud week doesn’t change where AI is heading.
Apple brought the charm. Nvidia brought the chips.
Checked on October 31, 2026. An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: the full five-day office week doesn’t come back. Hybrid quietly wins.
More mornings that start with a workout, not a commute. That is the bet.
Time back is the new luxury.
Our readLikely. We’re leaning toward hybrid as the normal week, not the exception.
Our bet: the US economy avoids a recession in 2027.
Every few months someone says the next downturn is right around the corner. We’re betting the other way. People keep working, keep building and keep adapting, and that steadiness tends to outlast the scary headlines.
Your money: keep doing the boring things. Spend less than you bring in, keep a cushion, and don’t make big moves because of one loud week of news.
Your job: be the person who makes the team better. In a steady year, the people who keep learning are the ones who get the next opportunity.
Your plans: if you’ve been waiting for a “safe” moment to book the trip, start the project or have the family conversation, don’t put your life on hold for a forecast.
Our readBetter than even. We’re leaning toward steady, not scary.
Bold call from a guy who still checks the weather twice.
An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: driverless rides give commute time back in more US cities.
Picture the drive to work turning into reading time, call time or just quiet time. That’s the part we care about.
It won’t show up everywhere at once. But every city that gets it hands people back a little of their day.
Here’s what we’re watchingMore cities saying yes. We’re leaning toward it becoming an everyday option in more places.
Finally, a commute where nobody asks you to merge.
Honest take: the best productivity system ever invented is still going to bed on time.
Our bet: automation becomes a normal part of the human workday.
Not robots taking over. The boring stuff quietly running itself: the scheduling, the follow-ups, the copy-and-paste, the reports nobody wants to build by hand.
People stay in charge of the judgment, the relationships and the ideas. The busywork moves to the background.
What it means for you: look at your week and find the task you do the same way every time. That’s the first one to hand off. Every hour you get back is an hour for training, family or the work that actually needs you.
Our readLikely, and already underway in plenty of offices.
The goal is fewer spreadsheets, not fewer people.
You just got a free Friday. What are you doing?
How many days are you in the office?
Our prediction for 2027The full five-day office week doesn’t come back. Hybrid quietly wins. More time back for training, family and the weekend.
Live results open soon.
Our bet: CoreWeave works through its rough patch and keeps growing through 2027.
The headlines got nervous this week. That comes with the territory for a company growing this fast.
The trend underneath is steady: demand for AI computing keeps growing, and the big customers are still asking for more. The companies building the backbone of AI tend to work through rough patches and keep going.
Our readLikely. A rough patch isn’t the end of the story.
Debt is a tool. Just don’t let it hold the steering wheel.
Scored on December 31, 2027. An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: Anthropic goes public before the end of 2026.
The timing slipped and the headlines got messy. The appetite didn’t.
When a company is growing this fast and needs this much computing power, the public market is where the big checks are. They’ll go get them.
Our readLikely. Late is not the same as never.
Every great company has a “we’ll get there” season.
Scored on December 31, 2026. An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: the Fed raises rates at least once more before its December meeting wraps up.
Borrowing has been getting more expensive, and we don’t think that trend is done yet.
Your money: plan as if cheaper money isn’t coming soon. Pay down the expensive debt first and keep a cushion. Boring wins here.
Our readLikely. We’re not counting on relief this year.
Hope is not a refinancing plan.
Scored on December 9, 2026, when the Fed’s December meeting ends. An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: no sweeping federal AI safety law gets signed in 2026.
Plenty of talk about it. Washington still moves slower than the technology.
For builders, the rules at the end of 2026 look a lot like the rules today. Keep shipping, keep it responsible, and don’t wait for a rulebook that isn’t coming this year.
Our readVery likely. Talk is fast. Laws are slow.
Build like the rules will change. Just not by Christmas.
Scored on December 31, 2026. An opinion, not a promise and not investment advice. That’s what a bet is.
Our bet: Anthropic still has the top-ranked AI model on December 31.
Google has closed the gap fast. This is a real race now.
What it means for you: don’t marry one AI. Use the best tool for the job, and switch when the leader changes.
Our readClose call. We’re leaning Anthropic, barely.
Loyalty is for people. Tools have to earn it every month.
Scored on December 31, 2026, at noon ET, on the public AI leaderboard. An opinion, not a promise and not investment advice. That’s what a bet is.
Predictions
- Nvidia is still the company the AI world runs on come October 31Our read: likely
- Hybrid work quietly winsOur read: likely
- The US economy avoids a recession in 2027Our read: better than even
- Driverless rides give commute time back in more US citiesOur read: leaning yes
- Automation becomes a normal part of the human workdayOur read: likely
- CoreWeave works through its rough patch and keeps growing through 2027Our read: likely
- Anthropic goes public before the end of 2026Our read: likely
- Borrowing stays expensive: one more Fed rate rise before its December meeting endsOur read: likely
- No sweeping federal AI safety law gets signed in 2026Our read: very likely
- Anthropic still has the top-ranked AI model on December 31Our read: close call
Our own calls. Opinions, not investment advice.
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