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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Ater 10 happy years flying @Delta, I'm switching to @united because of @Starlink.
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I used to love @crunchbase and used to use it all the time. Feels like the UX keeps getting worse. I'm a paying user and seems like a waste of money. From Trustpilot:
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AI HEROES: DUKE ENERGY. Duke Energy says the AI it uses to forecast demand, predict outages and run its grid had saved customers about $500M as of 2024. s201.q4cdn.com/files/doc_dow… latitudemedia.com/news/aws-l…
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Dear Friends: Can someone introduce me to @GregShove?
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Rob Bailey retweeted
Literally just do this method if you’re starting out as an SDR. Give him a follow too
I was the #2 SDR in America for my company last year. Here's what I did vs the average SDR. First, I didn't listen to my manager. Sounds crazy right? He was always on me about dials, volume, how many emails to send. I built my own process. When I joined, I told the person I started with: I'm going to figure out what works here and be the best in our office. That's what I did. I talked to the top SDRs about what was working but took what they said and made it my own I got close with all my reps. My first goal with each one was to earn their trust by booking them a really important meeting. I did it for every one. I met with my reps every Monday and Friday. On Mondays they'd give me the sauce: what's going on in their accounts, who's in them. I used that to book meetings. Most of my meetings came from accounts that already knew us: - Past opps - Past POCs - Past customers - Marketing leads - Growing inside accounts. Get one team, then the next. Meet with an IC, then reach out to their boss. I never parallel dialed. Only targeted outreach with an actual business reason for them to take the meeting.
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Rob Bailey retweeted
My predictions over the following months: 1. Stock market will get hurt bad when the music stops on data centers, models, and chips. Too much froth, too high of investment, too many companies will fail. The switching costs are low. I don't know how these companies will become profitable. Its a mega bubble. The rest of the economy is already in a deep recession. Real pain will set in when the public markets dive. 2. Power is the bottleneck. AI is burning an absurd amount of power. The cost of electricity is skyrocketing which is making the cost of everyday life more expensive and hurting quality of life. I'm against data centers because of the power, not the water. The grid is extremely fragile and the weakness will be exposed in the coming months. 3. Subsidies are skewing the market. AI isn't cheap. The prices to use it are artificially low because of subsidies all the way up the chain. You pay $20 or $200 a month but the true costs are 10x That spread is venture capital money being incinerated at scale. When they raise the price, the users will disappear and investors will hold the bag. 3. A big security breach is coming. A bank, a certain model, something is going to rock our world. People are letting bots log in to their banks, their email and everything else. Big trouble coming. 4. Grokbot is exceptional. Its the first model that is adding significant value to my everyday life. I don't know why anybody would use a different personal assistant. 5. AI is insanely high maintenance Billions are being poured into training the next model. They day it comes out its already behind. China has cheaper electricity and more chips. The chips they bought will be obsolete in 18 months. Companies are stuck paying big money every month to maintain and update all of their AI tools. Its a mess. 6. The power companies will renege on their deals. Political pressure will unwind all the unsustainable power deals these data centers and LLMs have negotiated. Power costs will explode. Then comes the choice: Do we jack up costs for our AI / compute and watch everybody switch to the next model or do we incinerate more VC capital? Nobody wins. 7. Credit will be the first domino to fall. Data centers are already struggling to finance the GPUs over 10 years when they will be obsolete in 18 months. We'll end up with a shit load of half built data centers who can't negotiate power rates or buy chips because nobody will let them borrow money. The money will get cold feet as soon as the markets tank and the show will be over. 8. It'll be a dark, dark period in economic markets. The people who own assets that make real money (real estate or businesses) will win. The people who plan ahead and avoid massive leverage will win. The people with cash on their balance sheet will accumulate more assets and generate exceptional wealth. -- Don't listen to me. I'm just a bear. Not investment advice. Good luck!
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Experian, a $35 billion business with roots dating back to 1826, is surprisingly AI-native. Its new Chief AI Officer, Vijay Mehta, broke down the credit bureau’s end-to-end AI strategy. Complete list of notes... Big takeaways:
 • Experian is well past proof of concept, with AI capabilities running in production throughout the company.
 • The next stage is what Mehta calls "reimagination." Redesigning how work gets done through delegation to agents vs. prompting chat bots. 
 • Adoption is close to universal. 85% of employees actively use the company's AI tools, 88% of developers use coding assistants, and employees built more than 6,000 custom GPTs by the first half of fiscal 2026.
 • They're seeing real ROI. It's measured in time savings, time to value, quality, velocity and traditional before and after financial metrics, not in adoption or token use. How they built the foundation:
 • Within months of ChatGPT's launch, they trained thousands of employees and put AI policies and guardrails in place.
 • AI traffic was routed through a control plane that gives them observability, monitoring and security.
 • They wrote a GenAI risk framework and built the Experian GenAI Platform, an internal system that lets employees build internal-facing & and customer-facing apps, while accessing company data securely.
 • They rolled out a coding assistant to their large developer base and built their own Experian GPT into products like a digital financial assistant and their Ascend platform.
 • They created a GenAI Center of Expertise, which now sits under Mehta's AI office.
 • Since then, AI has spread across software development, analytics and business operations. AI inside the employee experience:
 • MyCareer platform recommends learning and career moves and helps managers spot skills gaps.
 • Nadia, an internal AI coach, helps employees set goals, build development plans and prepare for performance reviews.
 • Nadia also gives leaders personalized coaching and 360-degree feedback. On models and cost:
 • "Not everybody needs the most advanced frontier model. Most workloads can be done with a free or very low-cost model."
 • He compares reaching for a frontier model by default to using a sledgehammer on a job that needs a much smaller tool.
 • They run a mix of open-weight models adapted to their own environment and frontier models accessed through AWS Bedrock.
 • The control plane routes each workload to a model based on the task, language, region and regulatory requirements. On agent safety:
 • Guardrails are designed into the architecture from the beginning instead of being added later.
 • Their Agent Operating System runs on that control plane, so it can sandbox, monitor and stop an agent process when necessary. "The ability to kill a process, the ability to kill a process, I will repeat that, we've got all of that built in."
 • Their risk profile differs from the frontier labs' because their systems work over a defined body of financial and identity data, without broad access to the internet. "We start with our corpus of data and we put controls around that. And we know exactly how the data is moving." What the CAIO role actually is:
 • Experian is a big company split into many business units. His job is one common AI strategy and direction: "to make sure that we are all marching in the same direction."
 • He accelerates the AI agenda both internally and externally.
 • Risk, security, compliance and partner choices all come together in the AI office. AI as the new middleman:
 • Consumers increasingly start their financial journey inside an AI assistant instead of going to Experian or a bank, so Experian is meeting them there.
 • It's the first personal finance app integrated with Google's Gemini. US consumers who connect their Experian accounts can ask Gemini about their FICO credit rating and what's affecting it.
 • Inside ChatGPT it has launched personal loan shopping, credit card shopping and an insurance marketplace.
 • On the enterprise side, ServiceNow is the first integration partner for its Agent Operating System. Under a multiyear partnership, ServiceNow agents tap Experian's Ascend data and decisioning from inside enterprise workflows.
 • It also launched Agent Trust, which verifies that an AI agent is actually connected to the consumer it claims to represent.
 • Could agents eventually skip Experian and get the data somewhere else? He says they can't reproduce it. Decades of longitudinal financial and identity data, plus its provenance and regulatory standing, are what matter when the output drives consequential decisions. "In order to be able to make a decision, you've got to have that trusted data source." His advice if you're early:
 • Train employees.
 • Set guardrails before deployment. "So much of safety and responsibility comes from the person interacting with the system."
 • Route AI traffic through a controlled gateway where usage can be observed and policies enforced. Which AI leader should I learn from next?
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If you are a very curious founder, Grok and other AI platforms can be very, very addictve. :-)
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OH: "Rumination is worshipping the devil." (one of my favorite quotes this year)
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Rob Bailey retweeted
$0 MRR founder: "We're building the future of human productivity" $50K MRR founder: "We help plumbers send invoices" 💀
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Rob Bailey retweeted
Couple of underrated hacks for GTM... > Call every positive reply > Reply in under 5 minutes > Pitch a time, skip the calendar link > Ask "wrong person" replies who the right one is > Log every "not now" with a date > Re-contact your whole TAM every 90 days > Build lookalikes off closed-won deals > Use job posts as buying signals > Case study from their exact industry > 1 segment per campaign > Verify every email before it sends > Keep bounces under 1% > 10 to 20 sends per inbox a day > Turn off open tracking Simple as.
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Rob Bailey retweeted
Top 10 private companies in terms of interest in the secondary market for their shares
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Rob Bailey retweeted
My biggest takeaways from Rob Snyder, author of The Power of Pull: 1. Solving a pain point isn’t enough to get people to buy your product. Rob’s first startup checked all the classic boxes: hair-on-fire problem, a differentiated solution, and design partners using it daily. Yet he still spent two years pivoting aimlessly. Every prospect agreed it solved real problems, but none bought. 2. Rob’s "PULL" framework identifies four conditions that drive a buying decision: The buyer has a Project on their to-do list, and a reason it’s Unavoidable right now. They also have a List of options they’ve considered, each with Limitations that leave them stuck. That person is a “coiled spring,” desperate to find a product to buy. 3. The right cold outreach message needs to be interesting, not persuasive. Its only job is to get someone to take the call. Rob calls this “founder magic” outreach. One startup’s entire message was: “Hey, Snoop Dogg invested in us, and I thought you’d find it interesting too. Would you be open to chat?” No pain points, no value propositions, no personalization. Just something that gets a conversation. Rob’s LinkedIn benchmarks are 20 requests a day, 30% to 40% accepted, 30% to 50% of those replying, and most saying yes. 4. Design partners are a trap. Nearly every time, the partner buys into your vision, hands you a pile of feedback, and never buys. Then you realize “all of their feedback was just like them playing Steve Jobs.” The people who have something important to get done don’t want to be design partners. They just want it done. Offering a partnership is “a negative signal to people who actually have pull, and a positive signal to people who don’t.” 5. Pull belongs to a specific person, not to a company. A common founder mistake is to say “we sell to SpaceX” or “we sell to mid-market private equity firms.” In practice, you’re selling to the head of legal at SpaceX, who has a particular project on her to-do list she can’t solve with her current team. The company doesn’t have pull. She does. 6. The signal of real pull in a meeting isn’t just enthusiasm—it’s someone leaning in and asking how to move forward. “Wow, that’s amazing, totally the future of our industry, I can see how that would save us a ton of money” is not pull. That’s a polite exit. What Rob looks for is a “pull-shaped action”: “Wait, you can do that? How do we get started? Does the product exist yet?” Before the product even existed, someone in pharma told one founder, “If you can do that, I will pay you right now.” 7. Run the first sales call like a detective, not a pitcher. Rob’s opening question is always some version of “I’m sure you get a lot of people reaching out. Why did you take this call?” The best-case outcome: they fill out the PULL framework for you unprompted. They tell you exactly what they’re trying to do, why now, and what they’ve already tried. 8. When a call goes lukewarm, throw the Hail Mary. Ask, “Is there anything on your to-do list that you would pay me to do right now?” A team selling applicant tracking software to governments got a lukewarm reaction but then learned the buyer would pay for help with job descriptions. That became their first contract. When founders are truly stuck, Rob recommends going into “goblin mode,” a burst of slightly crazy effort to get in front of customers, like the founder whose parents went door to door to dental offices for him. 9. Rob calls "The Case Study Factory" his most important idea. The job is to find one type of customer who says 'hell yes' before and after buying, then repeat that success through pipeline, sales, and delivery. This customer forms your repeatable case study. A startup finds one repeatable case study and then repeats it a million times. To grow as fast as possible, borrow the theory of constraints from manufacturing: find the bottleneck in the process of repeating that case study and treat it as the only thing that matters until it’s fixed.
An 86-minute guide to finding product-market fit Rob Snyder (@RobSnyder1) is the author of The Power of Pull, has helped over 50 startups go from zero to $1M+ ARR, and is the most requested guest by my podcast listeners. We discuss: 🔸 The PULL framework for finding a customer who’s "weird not to buy" 🔸 Where the best startup ideas come from 🔸 The cold outreach message that gets calls 🔸 How to run your first sales call (and why he skips design partners) 🔸 The "Hail Mary" question and "goblin mode" Listen now 👇 youtu.be/19qrLchbQEc
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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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