AI-Native & Agentic Founder/Operator (New AI company going into private beta in the next few weeks!)

New York, NY
Joined January 2009
There are massive opportunity areas in AI adoption that no one is thinking about yet.
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Every time I spend time at an Apple store I want to buy more stock
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Rob Bailey retweeted
some revenue stats for Anthropic
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WOW: "I built a desktop app over the weekend to improve the experience for our customers." (Our FDE) I LOVE BUILDING COMPANIES IN 202^!
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AI HEROES: WALMART. Walmart says one AI system that spots overstock and automatically sends it to stores that need it, before it goes to waste, has already saved the company more than $55M. corporate.walmart.com/news/w… chainstoreage.com/walmart-de… pymnts.com/walmart/walmart-e…
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Rob Bailey retweeted
Rippling went from 40 outbound reps to 400+ in 4 years & is now valued at $16.8B. I went through everything public on how that machine actually runs. Their early formula was 3,000 emails to produce 15-30 demos. Half a percent conversion, run at enough volume that it didn't need to be better. 5 things they got right: > outbound reports to the CRO, not to marketing > inbound & outbound SDRs sit on separate teams > an overlay team that only sells new products into existing accounts > messaging that names the competitor instead of pretending it isn't there > demo targets set backwards from AE capacity, not rep activity Blended CAC payback lands around 17 months against a SaaS average closer to 28. 3 things I'd change if it were mine: The whole thing is a headcount motion. Every extra meeting needs another rep, and a rep takes 3-4 months to ramp. There's no phone layer anywhere in it. On one of our recent builds calling produced 62% of the meetings off 44% of the touchpoints. And when an SDR leaves, the list & the account knowledge walk out with them unless the system is holding it rather than the person. Every one of those 400 seats has to be refilled and re-ramped when someone quits.
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Rob Bailey retweeted
A surprising thing about AI adoption (outside of SF): Many CFOs are leading the charge. And many technologists are skeptics.
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We've been running our ENTIRE GTM through a Hermes agent… The results have been unreal (list building is a Slack message now) So I wrote the whole system up in a 14-part doc.. It covers how our team built it and the exact briefs we send it, from a laptop or a phone at any hour Here's what's inside the doc: > The architecture, piece by piece (6 components, starting with a $9/month server that stays on 24/7) > The security rules (so it can run overnight without spending your money) > The skills library (what goes in a skill file, and the part that matters most) > A request, start to finish (the 5-row sample that catches a bad brief before it hits 5,000) > The 5-part brief formula (with 3 real requests you can copy and run today) > The lists no database holds (how the team mapped 69,204 businesses for one client on 19 data points) > The quality layer (how raw exports go from 50-60% ICP fit to 90-95%) > The reply side (5 agents, and the one booking ~10 meetings a week on our own offer) > Building your own, in order (what to set up first, and the one skill to start with) All backed by what our team learned sending 10M+ cold emails and generating $70M+ in pipeline for 100+ B2B companies Like + comment "HERMES" and I'll send it over (Must be following me to receive it)
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Rob Bailey retweeted
i grew a company from 0 to $4M in a year. i've led marketing at 3 multimillion-dollar companies. 11 marketing principles i still use every week: 1) say one thing. buyers remember one sentence from you. pick it on purpose. 2) the buyer's words beat yours. steal phrases from sales calls, reviews and support tickets. 3) name what you replace. "better than nothing" is a weak pitch. "better than the spreadsheet you hate" sells. 4) sell the after. show what their week looks like once it works. 5) put proof next to the claim. a number under a promise does more than a row of logos. 6) specific beats clever. "set up in 4 minutes" beats any pun you'll ever write. 7) the founder is your best marketer. buyers trust a person before they trust a logo. 8) price is part of the message. a cheap price tells buyers it's a small problem. 9) write for the skeptic. once the doubter nods, everyone else follows. 10) repeat yourself. you'll get sick of your message long before the market hears it once. 11) taste is the edge now. AI made average copy free. buyers pay for judgment.
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AI HEROES: KROGER. Kroger expects to save about $500M by 2029 by using AI to tell store teams which fresh food is about to expire or go unsold, so they can act before it turns into waste. s202.q4cdn.com/files/content… stockanalysis.com/stocks/tra… supermarketnews.com/grocery-…
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Claude is doing a complete overhaul of all 500+ of our Linear tickets. Based on a pretty detailed spec. YOLO!
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This revelation is yet another embarrassment for our state coming from Letitia James. The Attorney General’s office is supposed to be the chief law enforcement office in the state and has more than 700 attorneys. The fact that they can’t investigate a sexual assault case with the resources they have shows Letitia James is not running a serious office. And New York taxpayers will be forced to pay millions of dollars to outside attorneys because of it. It’s time for a change at Attorney General and on November 3rd we’ll make one. nypost.com/2026/10/24/us-new…
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Rob Bailey retweeted
Without marketing, no one sees you Without branding, no one chooses you Without design, no one trusts you. Without content, no one hears you. Without distribution, no one finds you. Without automation, you can’t scale. Without innovation, you never stand out. Without proof, no one believes you. Growth needs all the above.
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Services!
Worldwide spending on AI is projected to reach ~$2.7T this year. Yet, only ~1% of it is expected to go to the models themselves.
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Rob Bailey retweeted
What we're hearing about AI in PE on calls this quarter: 1. Funds are putting their own AI engineers inside portcos. 2. Portco CFOs see more pull requests than ever, but the codebase isn't getting better. 3. Dev vendors that won't use AI are being asked why they're still being paid. 4. Funds want AI work priced against EBITDA upside. They ask about revenue per FTE. 5. Every portco runs its own AI experiment. None of it makes it to the next company. 6. New board seats come with one job: choose the AI vendors. The funds making progress are getting one workflow working at a time.
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Out of all the candidates running for office this year, Saritha is the one I’m most excited about. She’s competent, sharp as a tack, understands the role of the job, and far from a political hack who might abuse the office the way we’re seeing under Tish James.
Tish James' GOP AG rival Saritha Komatireddy vows to declare NYC antisemitism state of emergency 'on day one' if elected trib.al/xXMbT2F
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Rob Bailey retweeted
There are seven main steps for your company to go from tool adoption to agentic org. Most companies sit on step one, shopping for step seven technology. They need step four discipline. Step one: tool adoption. AI tools exist across the org, humans run each one. Developer closes the lid, automations die. Somebody goes on vacation, the workflow goes with them. Step two: context layer. Knowledge graphs per department, each behind its own API gateway. Sales queries engineering through an API. Separated domains keep agents from hallucinating across departmental boundaries. Step three: harness engineering. Build evaluation criteria, routing logic, and quality gates before you pick a model. The LLM comes in last. Your harness is your IP and your capex. The model underneath is a commodity you swap when something better ships. If changing the LLM breaks your system, you built a dependency, not a platform. Step four: go headless. Host every automation outside a laptop. It fires on schedule, on conditions, without a human logging in at 9 AM. Companies stall here because nobody forces the migration from “script on my desktop” to “service that runs on its own.” Step five: governance. RBAC on every knowledge structure from day one. TTL on every agent. Dead agents are tech debt with active API keys. Past 100 tools, you need lifecycle management. Retire anything that hasn’t run in 90 days. Deprecate anything whose eval scores drop below threshold. Step six: agent-to-agent. Stitch headless instances together within a value chain. Agent A finishes, hands off to Agent B. An LLM sits between them as a quality gate, judging every handoff before it passes through. Step seven: step functions. Orchestrated, semi or fully automated workflows. Agents handle volume. Humans handle exceptions. The org runs on agent output. We walked a VP of Engineering through all seven. Told him: “You’re on step one. But over a hundred tools means step four is closer than you think.”
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Dear @AWS: We want to give you more money! We are building our company on AWS. But we've had some issues getting access to certain models, etc. Can you connect us with someone who can help expedite a few requests?
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Rob Bailey retweeted
I see AI agents fail inside big companies in two ways. The first is obvious. The person who built it leaves, and the agent goes with them because it only ever ran on their laptop. Nobody hosted it because the company never decided where agents should run. The second is easier to miss. The agent gets hosted and runs for months without anyone checking it. The model updates or a system it reads from changes, but it keeps answering just as confidently. Before a company ships its second agent, I want these written down: > Where every agent runs. One runtime for the whole company > Who registers new agents > Who owns each one, by name > Which tools and data it can access, and who approved that access > When it gets reviewed, and when it gets retired None of this is exciting. But if the business is going to rely on an agent next year, someone needs to be responsible for it after the person who built it moves on.
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A few months ago, I pitched @fendien from @Work_Bench on the new company we're building. Work-Bench is one of the best early-stage enterprise investors out there and their community is 🔥. He stopped me 2 minutes into my presentation. He'd already invested in something competitive. :-( Was I bummed? Absolutely. But I have enormous respect for the integrity Jonathan showed by being so transparent. Hope our paths cross again.
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