John Eng (Right Side Capital) retweeted
That Microsoft buyout post took off way more than I expected... and the part I keep coming back to is the 24-month journey, because most of those months have very little to do with the tech.
AI adoption is a people problem. People don't like change, and honestly most orgs aren't where they need to be for this yet. I've been doing Microsoft and enterprise IT for 25+ years, and at @DigitalMeld we're in the middle of these rollouts right now on M365, Azure and Power Platform. What actually eats the time:
• Figuring out who owns which process, because half the time nobody does, or three people think they do
• Writing down how the work really gets done today... not the SOP from 2019 that nobody follows
• Agreeing on the single source of truth, and where it should live and who owns it
• Getting managers comfortable with their team working differently, and with what that means for their own role
• Training that's more than one lunch-and-learn and a recording nobody watches
• Lots and lots of conversations. With IT, legal, HR, operations, the people whose jobs are changing... and then the same conversations again a month later
Even though you know what you're doing is right, and they're better off following your guidance, you still have to win people to the cause. You have to prove that you will be making people's lives easier.
All of that takes planning, time, and leaders willing to sit in the room for those conversations. Cutting a bunch of the people who'd have to do the changing doesn't make it go faster. I'm pretty sure it does the opposite.
AI doesn't make AI adoption easier, it just speeds up some of the process. But the process is the process, all the same.
This is the canary in the coal mine, y'all. The AI math doesn't math. Microsoft is offering buyouts for nearly a quarter of it's workforce.
AI adoption for businesses is a 24-month journey in a perfect scenario. They aren't seeing adoption fast enough to offset their CapEx spending... and they aren't alone. Add Anthropic's measly revenue numbers (compared to their CapEx), and hopefully you get the point.
These aren't buyouts because Microsoft found efficiencies with AI, they are buyouts because they (the AI industry) spend trillions (collectively) building the best tools the world has ever seen, and no one knows how to use them. digitalmeld.io/blog/who-is-p…
John Eng (Right Side Capital) retweeted
Around half of Seattle businesses report that are considering moving or shrinking, blaming a business environment that they say is getting worse and don’t believe it looks like it will get better, according to a survey from the Downtown Seattle Association and Seattle Metropolitan Chamber of Commerce. kiro7.com/news/local/survey-…
John Eng (Right Side Capital) retweeted
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1) Startups fail - few make it to exit
2) Fundraising is hard, dilution, downrounds / flat rounds happen
3) later stage investors want protection (liq pref, etc..) and that limits what founders (and employees get)
4) what else?
Hey Redmond folks, it's a great time to build your startup. Start now!
cnbc.com/2026/10/26/microsof…
John Eng (Right Side Capital) retweeted
BofA Analyst Andrew Obin breaks down Data Center costs by line item for the next 4 years.
10.23.2026
From compute, to liquid cooling, backup power etc.
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Here’s my westie, Sophie - reporting to duty.
JUST IN: Palmer Luckey's genetically modified military dog startup, Warhound, comes out of stealth, aiming to create enhanced canines for the U.S. military.
Readers added context they thought people might want to know
This is NOT Palmer's company at all, his company Anduril is only supplying the tech for the dogs, and this is a wholly owed Collosal entiity
x.com/palmerluckey/s…
Put me on the waitlist. I need one to keep my westie company
John Eng (Right Side Capital) retweeted
BREAKING: @noxmetals, the YC-backed manufacturing startup, says it has reached a $25M annualized revenue run rate in less than a year.
The Detroit-based startup is automating metal cutting and supply for the American industrial base.
John Eng (Right Side Capital) retweeted
TLDR; we will probably never get another ARR number from Anthropic, which is healthy. Should force the market to move away from extreme focus on Anthropic/OpenAI ARR numbers to hyperscale growth rates, which are a much better metric for AI at this point given they capture Muse, Grok, Gemini and Open-Source.
Anthropic FCF positive in Q3 and reaccelerating in October on Opus 5.5 per third party data. Roadshow in several weeks will happen after this has been widely confirmed. Unit economics much better than expected given positive FCF with 75% of their compute going to training. All per public reporting.
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OpenAI continuing to grow at the same pace per Sarah Friar interview after they took share vs. Anthropic in Q3. Means the sum of Anthropic/OpenAI growth is accelerating from the Q3 pace. OpenAI probably hits FCF positive in the next few months.
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Open-source growing much faster than either Anthropic or OpenAI. Modal tripled since May and is 15x YoY per yesterday’s announcement. Open-source tokens generate more revenue and profit for the hyperscalers/neoclouds than frontier tokens. *Every* open source inference cloud I am aware of is growing faster both sequentially and YoY than either Anthropic or OpenAI. And their combined compute spend is becoming material.
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Third party data pointing to hyperscalers continuing to accelerate in Q3. All report in the next two weeks. Acceleration should continue in Q4 and Q1 as installed base of compute slowly reprices higher closer to spot and new capacity comes online at higher prices. Continued acceleration in hyperscalers should help address external funding concerns.
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10 year yield down in a straight line over the last 24 hours.
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Some risk of escalation in Iran next few days, but earnings and mid-terms probably outweigh taking an ultra long-term view and looking out 30 days.
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Biggest risk imo remains cyber and OpenAI/Anthropic dominating the model layer. Fragmentation, competition and lower margins at the model layer are good for everyone else in the ecosystem and for America.
Slower for longer is much better than an overbuild and an actual bubble.
Great post. Scary. Exciting.
I spent 48 hours in SF hanging out with billionaires, data labs and AI founders and execs running $1B to $100B companies.
My observations:
1. Sooo MANY stories of data brokers making like $2M a WEEK selling company data to labs. I can't tell if it's the beginning or a bubble, and I kept wondering which niches are left. Digging into it actively.
2. At dinner, someone asked the table, "If a new model drops next month, does your company get better or worse?" HALF the table went quiet! I think that's the best question to ask about any AI startup right now.
3. The bar people talk about now is hitting $1B in revenue in 12 months (I guess that's the new unicorn?). What I didn't hear much about is retention. AI revenue can come in fast and leave fast, and I think we're going to see a lot of stories of AI companies with huge revenue and terrible retention.
4. It's pretty clear we're living through the reinvention of the computer. The model is the CPU, the harness is the operating system, and skills and plugins are the apps. Thinking about it that way makes it easier to see where the whitespace is.
5. We're maybe 12 months from an agent that can watch you work for a week and then do your job without any instructions. The screen recording plus agent memory plus local model combination makes this possible right now.
6. Agent harnesses feel like the new GPT wrappers, in a good way, especially vertical ones. The best teams I talked to treat the model as swappable. One founder walked me through routing different models to different jobs: one for taste and visuals, a cheaper one for the everyday stuff, another for text.
They use prompts they can move across models over fine-tuning, and A/B test the output on what users actually do with it: do they edit it, export it, share it? A vertical harness is basically four things: the connectors for that industry's data, evals written by people who know the work, rules for what the agent can and can't touch, and a clean screen for a human to review. The model is maybe 20% of it.
7. There's a lot of reverse engineering going on/cloning going on more than I've ever seen. People are decompiling software and rebuilding it with agents, and someone showed a suite of like 10 apps that are worth $5B+ each all that he cloned open source. Me and everyone are still thinking through what it means when software gets this easy to copy.
8. My guess is the value moves to data. If the software can be rebuilt quickly, what's worth paying for in a legacy SaaS company is the years of customer data and workflows inside it. Some SaaS companies are secretly data companies.
Gets me thinking about how do you truly value data for this saas companies? Like if we were buying these dying saas companies at 2x ARR before (as example), maybe there is a better metric. Idk, just thinking out loud here.
9. It feels like a good chunk of legacy software won't make it to the agentic era, especially anything built around people clicking through a lot of screens.
10. Every company I talked to wants to pipe its internal data into one place and expose it to agents through MCP. Then they look at the data and realize it's a mess: five versions of the same customer, old Slack channels, PDFs nobody can search. Cleaning that up feels like a big consulting opportunity!
11. A lot of founders are building the basic building blocks for agents: APIs, data layers and tools. Some of the companies I saw barely have a UI because the main user is an agent. I really believe the startups that build primitives to this agentic era will do extremely well. Building blocks is the best way to think about it.
12. Labs can get plenty of training data, but it's harder to get real examples of agents failing inside companies. Whoever has those logs has something valuable.
13. Someone running a big consumer company told me the next fight is over memory. The model that remembers the most about you wins, and the smartest model matters less than people think.
14. Physical AI came up a lot. Astra I think was the first model that got people into AI can actually do CAD, and I think a lot of people are thinking what does vibe manufacturing really look like. The line I keep thinking about came from a robotics founder: the hardest problems in AI are deployment problems now, not research problems. Their robots work on their own, call a human when they get stuck, and every one of those calls becomes training data.
15. Cybersecurity companies are having a moment and are actually cool companies to build now, especially the ones that clean up after a breach. Every agent with access to your systems is a new door into your company, and a lot of those doors were left open.
16. Some startups are worth more dead than alive now. A shutdown company with 5 years of Slack, email and code can get paid for licensing all of it. I wouldn't be surprised if founders start factoring that into when they shut down.
17. People are starting to talk about monetizing the agent web. It feels really early, but when the most popular user of the internet is an agent, what startups should you be building?
18. I think agent insurance is coming. Once an agent makes an expensive mistake, insurers will want audits before they cover anyone.
19. Several people said the hire they want most is someone with taste who can write evals. The models are getting good at generating ideas, so the hard part is judging which ones are good.
20. New trend I observed: startup raises VC, uses venture dollars to become a creator, startup fails, founder falls back on being a full-time creator and incubates other products bootstrapped.
21. Getting SIGNIFICANT distribution is HARD right now. Founders are sponsoring buses, buying billboards like crazy and throwing parties with famous DJs to get noticed. Kinda feels dotcom era in that sense.
Attention is what's scarce! The growth guy going viral sharing his UGC strategy from Wispr Flow is a good example. It's the sauce everyone wants, and I truly believe there are probably only 50 people on the planet who know how to scale these types of businesses efficiently in this era.
Always good to get that dose of SF. I felt sooo lucky to have such an incredible trip during such an incredible time in building businesses. Surreal in so many ways.
Happy to be home and locked in.
Until next time!
John Eng (Right Side Capital) retweeted
Today, we announced XP, a new XBOX division that will help grow our great games into experiences beyond the games themselves.
news.xbox.com/en-us/2026/10/…
John Eng (Right Side Capital) retweeted
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