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Brady Lenahan
@Bunch_of_Brady
VP Sales @ CloudZero | AI spend, sales productivity, and ROI | Hot sauce + Boston sports
493 Following    118 Followers
⚡️I actually think this is one of the defining patterns of the next decade. Not because smart people suddenly became less intelligent. Because the market changed what it rewards. For most of the twentieth century, intelligence and economic success were highly correlated because institutions had a scarcity of cognitive labor. The smartest engineer. The smartest lawyer. The smartest analyst. The smartest doctor. The system paid for intelligence because intelligence was scarce. AI is beginning to industrialize intelligence itself. That breaks the old bargain. The smartest person in the room no longer automatically creates the most economic value. The person who organizes capital. Owns distribution. Builds a company. Creates trust. Coordinates people. Owns assets. Uses AI better than everyone else. Often wins. The market has always rewarded value creation, not IQ. The twentieth century happened to make those two look almost identical. That may have been the anomaly. The deeper tragedy is psychological. Many brilliant people built their identity around being intellectually exceptional. Then the world shifted. Their comparative advantage disappeared while their identity remained attached to it. That creates paralysis. Meanwhile the “mid” person keeps moving. Not because they’re smarter. Because they optimize for the game that actually exists instead of the one that rewarded them in school. School rewards correctness. Markets reward adaptation. Those are different skills. The smartest people often become prisoners of their own models. Average people often become surprisingly successful because they update faster. The deepest pattern is this: Intelligence without agency is becoming one of the least rewarded combinations in modern civilization. That is why the post feels true. Not every genius is failing. Not every average person is succeeding. The distribution itself is changing. The future belongs less to the people who know the most. It belongs to the people who convert knowledge into ownership, action, trust, and leverage. The twentieth century rewarded being the best worker. The twenty-first increasingly rewards becoming the owner of the system the workers operate inside. That is the phase transition. And I think most people still believe they’re living in the old one.
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The threat to your SaaS company isn't your customer vibe coding their way off your product. It's their CFO going: “we have a $10 million tech budget, last year we spent $100k on AI, this year we're spending $3 million, so we need $2.9 million in savings. Turns out we don't need five productivity apps. You’ll love Teams when you get to know it.”
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This will not be popular—- Everyone is selling you tokens. They’re telling you to build more skills. More prompts. More agent wrappers. More orchestration. More context files. The more tokens you burn, the more they win. You don’t. The current obsession with “skills” architectures is a transitional phase, not the destination. Yes, they work. Yes, they can accelerate specific workflows. But they’re also creating tomorrow’s technical debt. Every new skill adds: • More maintenance • More prompt engineering • More governance • More testing • More vendor lock-in • More tokens consumed The dirty secret? As frontier models improve, many of these handcrafted layers become obsolete. You’re investing engineering effort to compensate for limitations the next generation of models will solve natively. This is exactly why I keep talking about AI factories, not AI assistants. An AI factory is deterministic where it matters, agentic where it creates leverage, and designed to continuously improve itself. Agents build the software. Deterministic services execute the business logic. Memory, evaluation, and governance become the architecture—not thousands of brittle skills stitched together with ever-growing prompts. That’s how you reduce costs instead of multiplying them. The next generation of enterprise AI won’t be measured by: * Number of skills * Size of prompts * Tokens consumed It will be measured by: * Cost per business outcome * Speed of autonomous execution * Quality of decisions * Ability to improve itself over time We’re still early. Many organizations are optimizing for token consumption instead of architectural efficiency. They’re building businesses that rent intelligence instead of owning capability. Build systems where AI creates assets—not token bills. The companies that understand this distinction today will have a structural cost advantage tomorrow. How you build matters. #AI# #EnterpriseAI# #AgenticAI# #Architecture# #DigitalTransformation# #CTO# #CIO# #ArtificialIntelligence#
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enteprise sales has two jobs: - get them into "imagine" mode via highly unique exec. frame - project manage their buying process like a friggin’ psychopath
Love @JayaGup10 takes on AI adoption and impact. The weakening of a company’s competitive advantage and moat is well articulated here
Some of the most coherent and thought-provoking predictions I've read in a long time
Over the past 3.5 years at @ElevenLabs, I've done unconventional things in GTM. Let me tell you why: - I hate hiring people that come with playbooks. In interviews, when someone tells me about their "playbook", I reject them immediately - Each company is different. Entering a market selling support agents is different from selling legal tech or ERP replacers. - Each market & product requires a unique thesis and approach. If you don't understand the market, you can't craft a narrative that will be sticky - AI has changed all dynamics. Experimenting is the only path forward - Thinking big and placing bets yearly delivers outsized returns. I only need 1 bet to work to smash the target for the year - Aligning the team in a Vision is the glue. Not many companies have a crazy Revenue Vision each year; mostly because leaders fear getting fired if something doesn't pan out. I can't be bothered - You build a startup to do impossible things. Unconventional leads to making possible the impossible Doing things unconventionally isn't easy - you face rejection internally & externally. But, hey, "this is the way". An example: I came up with the "Global hyper-local" concept in 2024. Let me tell you that most people didn't want to open markets, have teams on the ground, adapt product (incl translations) or stop being US-first, amongst many things. Today, we are global, +$500m in ARR, 50% of revenues come from outside the US, Enterprise is larger than Self-service, I have teams in +25 countries and have cracked the most difficult markets. Being unconventional works. Just be creative, driven, hands-on, pushy and jump through obstacles. But don't be silly; if a company doesn't value it, find a new challenge. We are lucky to live the best period in history to build companies.
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Philly traded a 29-year-old disgruntled and possibly misunderstood Brown in the prime of his career to New England, and Boston sent one right back.
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Most people are focused on AI’s impact on software and developers. Makes sense since that’s where AI was adopted first. The bigger story is that AI ROI is labor leverage and not proved outcome efficiency. @lukesophinos outlined that argument well for vertical AI.
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Every legacy vertical SaaS company hits the same ceiling: Revenue = ARPA × logos you can win. The denominators are fixed. There are only so many dealerships, law firms, or school districts. In most verticals, you can't build a billion dollar company from seats alone. Most people model vertical AI like better SaaS. That's too small. The real prize isn't a nicer product, it's a new revenue architecture. Legacy vertical SaaS sold software access. AI native vertical software sells software access plus completed work. For two decades, vertical SaaS has been priced identically: per seat fee, per location platform fee, payments take rate. The constraint is brutal. If your average customer pays $10K/year, you need 100,000 logos for a billion in ARR. In most verticals, that's more than the entire addressable market. Historically, there were two ways to raise ARPA: more seats or more products. Embedded payments helped, 30 bps on GMV can lift revenue. But payments are an attach, not a product. And the cost center they sit on, transaction fees, is tiny compared to the one AI attacks: labor. The new math: sell the work, not the chair. A seat based SaaS company gets paid when a human logs in. An AI native company gets paid when work gets pushed through. Vertical AI adds a third revenue line: AI credits. Calls handled. Documents reviewed. Claims processed. The credit line replaces a labor budget orders of magnitude larger than the software budget. Most founders anchor to legacy SaaS comps and price too cheap. The right anchor isn't CRM pricing, it's payroll, outsourced services, throughput. A dealership AI that recovers missed service appointments shouldn’t be priced against a CRM seat. A legal AI that absorbs chunks of junior associate time shouldn’t be priced against a case management subscription. Wrong comparison set, wrong company.
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Armstrong’s AI cost playbook only works if there’s a real workflow-aware layer between business work and model execution.
Some good best practices here on AI token cost optimization. None of these happens though without a deep understanding of the underlying work being done in a non-abstract way. The ultimate implication is that a layer between the work itself and the underlying intelligence needs to deeply understand your workflows, context, and business process. Now, each individual company doing this on their own is unlikely to be effective at scale, so as a consequence, this is effectively the playbook for any applied AI company right now. By evaling the models for the applied use cases, deeply understanding the domain, having tuned UX and features for the use case, and having the ability to support adoption and change (via FDEs), allow this layer to add a ton of value. And as a result, enterprises get higher ROI because you actually can get *more* intelligence per dollar by having optimal architecture and workflows. There will be many horizontal and vertical versions of this approach. Huge opportunity right now.
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A bit dramatic but we count on @AlexFinn for that. He’s not wrong that this sucks. I was ready to sink my entire weekend into 5.6 but now I have to weed the garden and get my oil changed.
Unfortunately it appears the world has changed and we are never going back OpenAI just announced GPT-5.6 Sol, a model that beats Mythos at 1/3 the price It will only be in limited release to start as the government reviews it The days of wide release frontier models are over The years of some executives shilling AI as a world destroying technology that needs regulation got what they wanted, regulation Now only the select few will get access to super intelligence. Leaving the normie class behind It's a massive loss. Now winners and losers will be picked by the government. Which sucks. All of this doomerism has done nothing but slow America down On the positive side, Fable 5 will have competition It appears OpenAI has discovered a new post training technique that is allowing them to make revolutionary jumps at a fraction of the price That is unbelievably positive for all consumers. Will be counting down the days until I get to use this model In the meantime I hope this was a wake up call to the entire industry that our words and marketing matter
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Non-developer AI spend is about to be the bigger story and larger disruptor. It’s also going to be easier to track back to value and ROI.
OpenAI says 97.9% of its employees are now using Codex, up from ~40% in August 2025; non-developer usage of Codex has risen 137x for individual users (@thomasclaburn / The Register) (Visit Techmeme dot com for the link and full context!)
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The first wave of AI ROI metrics came from engineering because that is where the first big bills showed up. That does not mean engineering metrics are the right way to measure enterprise AI. The CFO was never buying “more PRs” as the end state.
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Strongest take I’ve heard yet
Claude Tag is a Trojan horse.  Not because Anthropic is doing anything evil. Because the incentives are obvious. Day one, this looks like a great feature: tag Claude in Slack, let it follow the thread, remember context, connect to tools, break down tasks, chase work, and act like a teammate. But that is exactly the problem. The moment your AI vendor becomes a shared coworker, it stops being just a model provider. It starts becoming the place where work is interpreted, remembered, routed, and eventually executed. That is not model lock-in. That is context lock-in. You are now renting your company back from them. Models can be swapped. Agents can be copied. But the memory of how your company actually works is much harder, maybe impossible, to move: the Slack scar tissue, the exception paths, the customer promises, the unfinished threads, the weird workflows, the implicit owners, the “we tried that in Q2 and it failed” knowledge. Once that lives inside one vendor’s agent layer, you are not renting intelligence anymore. You are renting your company’s operating memory. And the pricing model makes it even more dangerous. A human coworker has a salary. Claude has unbounded tokenized activity. The more work moves through it, the more the vendor captures not just IT spend, but labor spend. This is the enterprise bargain people will regret: Convenience now, and rapid decent into dependency. The right architecture is simple: rent the best intelligence from whoever is best this month. OpenAI, Anthropic, Gemini, open source, whatever. But own the context layer. Your company memory should be inspectable, permissioned, portable, and model-neutral. It should not be buried inside the same vendor that sells you the intelligence and the workflow surface. Claude Tag is useful. That is why it is dangerous. Rent the intelligence, but own the context. Or, regret later.
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This is just unbelievable. When I first saw the workspaces CLI, I took it as a sign that Google might be finally pulling its head out of its ass. This project really did represent something new and smart and very timely from them, but wow wow wow. Let this be a reminder of just how hard organizational change is.
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Context and value should always be fundamentals! When money was free and valuations were inflated, we forgot.
One of the largest companies in the world is not only trying to reduce cost on Anthropic but ALSO trying to look for cheaper alternatives to Palantir Cost and context have never been so back
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Claude was a top 100 boy name in 1920. In 2025, only 40 US born boys were named Claude. Polymarket doesn’t do baby names so I’m setting the 2026 over/under at 500.5.
RIP the artisanal em dash. Two friends have lamented to me that they used em dashes long before AI made them radioactive. A whole group of people having to change their writing style to avoid sounding like Uncle Claude. The asymmetry is the gap ;)
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This developing story about Dario's failed communications with the White House confirms everything I've ever believed about the enormous power of the Sales Chad. You can be the smartest, most hard working, well-meaning guy around, but if you can't get people to like you, it's all for nothing. When the time comes to send one of your own to meet inside the Halls of Power, you don't send the Geek Squad. You must send the affable, beer-drinking, golf-loving Sales Chad. It literally doesn't matter if he understands the product half as well as everyone else. You send him. It's what he was put on Earth to do.
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sales folks your entire job is to not look like OR act like sales … it’s to cos-play the founder market should feel energy, passion, and trust through you