
Thought-provoking and insightful essays and podcast episodes about the technology industry. Become an Inside Orchard member today. Founder/author: @NeilCybart
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Inside Orchard on iPhone Duo looks 👍.
Using Touch ID to unlock an iPhone Duo.
Bonus: @AboveAvalon and @InsideOrchard are optimized for iPhone Duo.
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Jamie Dimon talked about this last week on JPMorgan’s earnings call.
Businesses should 100% be blocking personal AI agents from their sites, platforms, and services. Why? It’s clear Silicon Valley rushed the technology out without taking into account customer safeguards. When you have Mark Zuckerberg and crew gloating how they put Muse together in a few months, the takeaway shouldn’t be “wow, amazing,” but rather “that’s concerning."
This issue is a major problem for AI agent adoption. You are going to have large segments of the business world block them before tech companies get the adoption and usage that they crave.
insideorchard.com/essays/the…
SCOOP: Major U.S. banks are detecting unauthorized third-party AI agents inside customer accounts, including some attempting to take actions that appear to be independent of user instructions, sources told Axios.
The findings have alarmed banking executives, who are racing to restrict access to their systems as AI moves at a velocity faster than financial institutions can respond, multiple industry and bank executives told Axios.
Several banks are now preparing for worst-case and even “day after” scenarios, including how to rapidly secure or restore customer accounts if things go wrong, the people said.
Several bank executives told Axios they're struggling to distinguish between human users and AI agents. One executive said banks also struggle to determine whether agents are authorized by customers or potentially operating without their permission, more akin to rogue agent behavior.
Read my latest for Axios here: axios.com/2026/10/22/ai-agen…
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Apple
Amazon
JPMorgan
Delta
Amtrak
Charles Schwab
Yelp
What do these companies have in common with each other?
The War Against AI Agents Has Begun
insideorchard.com/essays/the…
Odds are rising that AI agents will be hamstrung by barriers being put up across the business world. Without mass market adoption, agentic AI may very well be kneecapped before consumers warm up to the technology.
The War Against AI Agents Has Begun
insideorchard.com/essays/the…
Odds are rising that AI agents will be hamstrung by barriers being put up across the business world. Without mass market adoption, agentic AI may very well be kneecapped before consumers warm up to the technology.
The battle described in the most recent Inside Orchard essay about Audio Intelligence has already begun.
Amazon launching its version of Apple Audio Intelligence via Bee hardware. Wild that one product attaches to the back of your iPhone like a leech.
As I discussed in my most recent Inside Orchard essay, linked below, there will be a battle for capturing the audible communication and interactions that encompass how we engage with the world.
insideorchard.com/essays/kee…
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A Tesla / SpaceX merger does seem inevitable at this point. Such a transaction could be great for Tesla as a business as it would have the same effect as Musk stepping down as Tesla CEO (which would benefit Tesla).
insideorchard.com/essays/tes…
BREAKING: A Tesla–SpaceX merger could be announced before Tesla’s annual meeting in early December, per Barclays.
The most likely structure: SpaceX acquires Tesla in an all-stock deal, with Tesla shareholders getting about 0.7 SpaceX shares per Tesla share, plus a likely premium.
Barclays says Musk would own about 37% of the combined company, with roughly 56% of the voting power.
Keep an Ear Out for Audio Intelligence
insideorchard.com/essays/kee…
While the iPhone Duo may have stolen the show at Apple’s September event earlier this month, Audio Intelligence was high on my list of intriguing new technology on display.
Oura was already facing an uphill battle with its IPO. Timing its IPO to come soon after Apple's big September event when Apple Watches are updated and new health monitoring features are unveiled...talk about an unforced error on Oura's part.
Timing is everything with an IPO. One has to wonder if Oura's decision to IPO in the fall, after Apple held its big product event of the year, was an unforced error. Apple will be one of Oura's biggest headaches going forward. Oura now has to try to explain away the deeper move into proactive health monitoring that Apple unveiled two weeks ago.
Here's my @InsideOrchard essay on why Oura's IPO is giving me déjà vu: insideorchard.com/essays/our…
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Maybe, just maybe, Nike is starting to understand it needs to look beyond sports for growth.
I’m not holding my breath though.
insideorchard.com/essays/nik…
Incredibly honored to join the Board of Directors of @Nike.
I’ve been a lifelong fan of the brand and everything it stands for: sport, innovation, creativity and constantly pushing what’s possible.
Excited to contribute to what comes next.
Just Do It. ✔️
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Last week, smart ring maker Oura filed its S-1 for an IPO.
It’s impossible to not have flashbacks of other hardware start-ups that went public over the past decade or so only to underperform in the long run.
Fitbit, Peloton, Sonos, and GoPro all experienced the same inevitable roadblock found with being a start-up generating the bulk of their revenue from hardware sales.
In the Inside Orchard essay linked below, I discuss why there isn’t enough skepticism surrounding the Oura story. Apple doesn’t need to launch a smart ring for Oura to be in big trouble.
insideorchard.com/essays/our…
Oura Files for an IPO: Here We Go Again
insideorchard.com/essays/our…
With the Oura IPO, it’s impossible to not have flashbacks of other hardware start-ups that went public over the past decade or so only to underperform in the long run. It’s tough seeing Oura being any different.
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Some people are drowning in AI mania and losing touch with reality. They are pushing AI features that can’t stand up to scrutiny. There’s a lack of awareness as to how the world works. These people have become AI-pilled. My essay:
insideorchard.com/essays/bec…
Becoming AI-Pilled
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We are quickly moving to a point in which one must be careful not to become AI-pilled – not to look at the world primarily through an AI lens. Clarity will be needed to see how best to integrate AI into our lives and society.
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For this week's @InsideOrchard essay, I wrote about my thesis that Wall Street has begun to predict a turn in Big Tech AI-related capex.
Much of Wall Street's cooling capex growth rates prediction is based on the reality that Big Tech is either at or getting close to their annual capex limits.
insideorchard.com/essays/wal…
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A lot of red and yellow flags are found with this latest financial maneuvering with Opendoor.
For the past year, I've been following Opendoor - not because the business is interesting but rather because the stock came to symbolize a trend that continues to gain steam in equity markets.
The pandemic, in addition to the rise of commission-free trading ushered in by Robinhood, led young people to think of the stock market as a social lever that can be used to get ahead economically. The perception is that the only way to get ahead is to bet on stocks that can rise 100x in short order.
I wrote about this over at @InsideOrchard with the following essay:
insideorchard.com/essays/the…
Some news. Today, for the first time in Opendoor's history, we bought back our own stock.
Our share count is down 5%. We paid for this buyback with money borrowed at a 0% coupon and we still have hundreds of millions of dollars left to grow faster.
There are plenty of helpful details, along with a lot of legalese, in our press release and 8-K (linked below). But there are a few things I want to say directly and in plain English.
First, I *despise* dilution. On my first earnings call at Opendoor, I told you that if we issue a share, it has only one job: to make every other share worth more for our existing shareholders, not to extend runway for management. The flip side is just as simple: when our own stock is one of the best uses of capital, we should buy it back. Today, we did just that - by 5%.
Second, I run a publicly traded company. I don’t get to have feelings about the macro or the way Wall Street works. My job is to understand the rules of the game and use them to find an edge and build a better company.
One of those realities is that our stock price has lots of volatility.
People disagree - A LOT - about what Opendoor could be worth one day. Some think we're worth less. Some think we're worth dramatically more. I obviously have a view…
That disagreement isn’t just noise - it has economic value that Wall Street monetizes every single day.
Most companies would treat this as a headache, but we see it as an asset. If people are going to speculate about our future, I'd rather our shareholders get paid than anyone else. So instead of complaining about volatility, we used those dynamics to borrow $650M at a 0% coupon.
Then we turned around and used part of those proceeds to buy back our own stock. At today's prices, buying back our stock and call options was one of the best trades on the board. The rest stays on our balance sheet so we can buy more homes and grow faster.
As for dilution, we bought our stock where we thought it was cheap and pushed any future dilution far above today’s price. Not one net new Opendoor share will exist below $10.38. And if we buy back stock in the future, that floor goes higher.
But why raise now? Because the best time to raise capital is when you don’t need it. We’ve proven the business can reach ANI profitability, but profitability is just the starting point, not the finish line. And waiting could make the shares we are buying back today more expensive, and homes we could be buying don’t get bought. I’d rather move now.
Some people will call what we did today aggressive. They’re right. But being aggressive is how we fixed a company that spent years being careful. I’d make that trade again.
To our shareholders: You trusted us with your capital. Today, for the first time, Opendoor used its own capital to buy more of itself. The company is putting its money where its mouth is. Tomorrow, I will too.
After our lawyers allow, I’m personally buying $100K worth of shares. I'm all in, and I plan to keep buying.
Wall Street Is Predicting a Turn in AI Capex
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We may be watching Wall Street embrace its latest turn prediction. Wall Street has begun to predict that the Big Tech capex arms race will cool.
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A Meta Contradiction
Some days, I find myself intrigued by Meta’s business. The company has one of the most fascinating & value-add content delivery apparatuses the world has ever seen. Owning multiple platforms that help connect businesses with billions of users provides Meta a massive advertising opportunity.
Other days, Meta’s business strikes me as a stain on society. Genuine content from accounts that we have chosen to follow is sprinkled in with a sea of slop from accounts that we don’t follow.
How can the same company lead to such radically different feelings? I suspect the answer is found in Meta’s income statement.
I discussed my thesis in the Inside Orchard essay available here: insideorchard.com/essays/a-m…
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My Inside Orchard essay for this week was focused on Meta.
Some days, I find myself super perplexed by Meta’s business. The company has what may be one of the most fascinating and value-add content delivery apparatuses the world has ever seen. There are other days when Meta’s business strikes me as a stain on society, an addiction-inducing slop machine representing grave harm for users.
How can one company fuel such opposing attitudes?
I suspect the answer is found in Meta's income statement.
A Meta Contradiction
insideorchard.com/essays/a-m…
Some days, I find myself super perplexed by Meta’s business. The company has one of the most fascinating & value-add content delivery apparatuses the world has ever seen. Other days, Meta’s business strikes me as a stain on society.
A Meta Contradiction
insideorchard.com/essays/a-m…
Some days, I find myself super perplexed by Meta’s business. The company has one of the most fascinating & value-add content delivery apparatuses the world has ever seen. Other days, Meta’s business strikes me as a stain on society.










