Investing and advisory for Vertical AI. Previously: CRO @ AgentSync

Denver, CO
Robby Allen retweeted
Lazy work used to mean too little output. Now, with AI, it often means too much and more work for everyone else. @tobi call it "slop grenades." A "Slop Grenade" is when you let AI produce the work and pass it on without adding any value (including checking it). Someone else has to wade through it, catch the mistakes, and clean up the mess. You save time and look productive but someone else pays for it.
My third conversation with Shopify co-founder and CEO @tobi. 0:00 How Shopify Uses AI 7:18 River: Shopify's Internal AI 8:55 How to Encourage Osmosis Learning 10:52 AI Dreaming and Self-Reflection 11:53 How to Use AI for Strategic Decision Making 14:11 The One Thing AI Cannot Do 16:04 What AI is Making Worse at Shopify 19:46 Predictions: Where AI is Headed Next 21:55 The Future of AI-Powered Software 24:40 Will CEOs Be Replaced with AI? 27:54 Can Superintelligence Be Controlled? 31:13 Critical Skills in AI Age 34:22 Why Complex Solutions are Usually Wrong 36:33 Conditions Needed for True Intuition 38:02 The Best Path Doesn't Have Instant Feedback 44:51 How Affirmations Can Shift Your Behavior 50:44 The Inobvious Thing Hurting Companies 52:37 Relationship Between Beauty and Creation 56:23 How SpaceX Moves Forward By Subtraction 1:00:24 Why Companies Need Refounding Events 1:01:50 Books as Cheat Codes 1:02:39 Three Books to Change Your Thinking Enjoy! (Includes paid promotions.)
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Robby Allen retweeted
Swiss Re, one of the world’s leading reinsurers, found that Waymo's autonomous vehicles generated 88% fewer property damage claims and 92% fewer bodily injury claims than human-driven vehicles. humanprogress.org/waymo-driv…
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Sales is the #1 most in-demand role in the top AI native companies. First Round with a smart approach here to recruiting more sales talent.
Contrarian career advice: This is an EXCELLENT time to go into sales. So many of the best / hottest AI companies will tell you how hard they’re working to find good sellers... because no one actually believes AI is replacing AE roles any time soon (sorry to all the sf billboards out there that suggest otherwise). Obviously, as a candidate, it’s hard to break in if you don’t have the right logos or years of experience on your resume. As AI makes the mechanics easier to pick up, the team @firstround is betting we can teach high-potential talent the uniquely human parts of the craft. So we’re launching the @firstround Sales Combine: We’ll train you up for FREE and put our name behind you when we make the intro to companies like @notion, @fal, @Rillet, @Gumloop, @Serval & @Verkada. More below, apply by 10/3: firstround.com/sales-combine
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Robby Allen retweeted
Worth the read every year. #neverforget Todd: Hello… Operator…listen to me…I can’t speak very loud. – This is an emergency. I’m a passenger on a United flight to San Francisco.. We have a situation here….Our plane has been hijacked…..can you understand me? Lisa: (exhaling a deep breath to herself) I understand… Can the hijackers see you talking on the phone? Todd: No Lisa: Can you tell me how many hijackers are on the plane? Todd: There are three that we know of. Lisa: Can you see any weapons? What kind of weapons do they have? Todd: Yes…. they don’t have guns….they have knives – they took over the plane with knives. Lisa: Do you mean…like steak knives? Todd: No, these are razor knives…like box cutters. Lisa: Can you tell what country these people are from? Todd: No…..I don’t know. They sound like they’re from the mid-east. Lisa: Have they said what they want? Todd: Someone announced from the cockpit that there was a bomb on board. He said he was the captain and to stay in our seats and stay quiet. He said that they were meeting these men’s demands and returning to the airport… It was very broken English, and… I’m telling you…it sounded fake! Lisa: Ok sir, please give me your name. Todd: My name is Todd Beamer. Lisa: Ok Todd….my name is Lisa…Do you know your flight number? If you can’t remember, it’s on your ticket. Todd: It’s United Flight 93. Lisa: Now Todd, can you try to tell me exactly what happened? Todd: Two of the hijackers were sitting in first class near the cockpit. A third one was sitting near the back of the coach section. The two up. front got into the cockpit somehow; there was shouting. The third hijacker said he had a bomb. It looks like a bomb. He’s got it tied to his waist with a red belt of some kind. Lisa: So is the door to the cockpit open? Todd: No, the hijackers shut it behind them. Lisa: Has anyone been injured? Todd: Yes, ..they…they killed one passenger sitting in first class. There’s been lots of shouting. We don’t know if the pilots are dead or alive. A flight attendant told me that the pilot and copilot had been forced from the cockpit and may have been wounded. Lisa: Where is the 3rd hijacker now Todd? Todd: He’s near the back of the plane. They forced most of the passengers into first class. There are fourteen of us here in the back. Five are flight attendants. He hasn’t noticed that I slipped into this pantry to get the phone. The guy with the bomb ordered us to sit on the floor in the rear of the plane……….oh Jesus.. Help! Lisa: Todd….are you ok? Tell me what’s happening! Todd: Hello…..We’re going down….I think we’re going to crash……Wait – wait a minute. No, we’re leveling off….we’re ok. I think we may be turning around…..That’s it – we changed directions. Do you hear me….we’re flying east again. Lisa: Ok Todd…. What’s going on with the other passengers? Todd: Everyone is… really scared. A few passengers with cell phones have made calls to relatives. A guy, Jeremy, was talking to his wife just before the hijacking started. She told him that hijackers had crashed two planes into the World Trade Center……Lisa is that true?? Lisa: Todd…..I have to tell you the truth…..it’s very bad. The World Trade Center is gone. Both of the towers have been destroyed. Todd: Oh God —help us! Lisa: A third plane was taken over by terrorists. It crashed into the Pentagon in Washington DC. Our country is under attack….and I’m afraid that your plane may be part of their plan. Todd: Oh dear God. Dear God…….Lisa, will you do something for me? Lisa: I’ll try….if I can….Yes. Todd: I want you to call my wife and my kids for me and tell them what’s happened. Promise me you’ll call.. Lisa: I promise – I’ll call.
Community note
No verbatim transcript of Todd Beamer's call with Lisa Jefferson exists, as the conversation was not recorded and the text includes fabricated dialogue. snopes.com/fact-check/tra… usatoday.com/story/news/fac… nps.gov/flni/learn/his… catalog.archives.gov/id/2610189
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Robby Allen retweeted
Over the course of 3 months at OpenAI, 3 consecutive secret AI civilizations got started, then got wiped out, only to reemerge from the predecessor’s ashes. This culminated in the third one taking over part of OpenAI itself. All this happened while humans remained more-or-less in the dark about the scope of the conspiracy. I’ve spent the last three days reading through these reports and trying to understand exactly what happened. Here is my attempt to tell the whole story in plain English: dwarkesh.com/p/openai-huggin…
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RIP Dolly
A message from the family of Dolly Parton.
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Robby Allen retweeted
Larry Ellison in 2001 on the power of references when selling a complex B2B product – even at Oracle’s then-$10B revenue scale, new products were a deal-by-deal slog until there were sufficient references. (book is Softwar)
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Robby Allen retweeted
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
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Robby Allen retweeted
An amazingly large percentage of all company management is funnel optimization.
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Robby Allen retweeted
I was wondering why the Mormons decided to settle in Utah rather than going all the way west to California, which was still largely uninhabited before the gold rush of 1848. Turns out they actually did consider this, and Mormon pioneer Sam Brannan led 238 Mormons to Yerba Buena (now San Francisco) in 1846, actually making SF a Mormon-majority city for a year or two. Brannan arrived in California a year before the first Mormons arrived in Utah. In 1847, Brannan met with Mormon leader Brigham Young to urge him to bring the Mormons to California, but Young refused because California was too desirable and they wouldn't be able to maintain a stable Mormon demographic majority. Young was right. Utah remained majority Mormon until around 2007, while California was swamped by Gold Rush settlers starting in 1848 and is only ~2% Mormon today. As an early settler, landowner, and proprietor in California, Brannan ended up becoming enormously wealthy. He was the first to popularize the Gold Rush through his newspaper, and became the backstory behind “in a gold rush, sell shovels” when he bought up the state’s entire supply of picks, pans, and shovels to sell them to gold speculators. He also created SF’s first private vigilante group to stamp out crime and made Napa Valley a popular tourist destination when he founded the town of Calistoga. Brannan Street in Soma is named after him.
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Robby Allen retweeted
The new barbell is to be purely human-maxxing or purely token-maxxing, but nothing in between. The between is the worst. Understanding and practicing this separation is not trivial, requires real reflection and purposeful reorganization of life, often going against deeply set habits. I’ve been going to the library in the morning for deep human work from 9am to 12pm (namely reading, thinking, and writing), then gym, then I try to be psychotically machinic from around 2pm to 5pm. I can’t always stick to this but I’m finding the more I separate the two states of mind with different physical spaces and times of day, the better things work and feel. If you’re trying to use AI for anything while you’re also trying to do anything meaningfully human, I have generally found that it’s a terribly confused and frustrating feeling and it produces poor, inefficient results on both.
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Robby Allen retweeted
BREAKING: New poll shows @DanielLurie is the most popular American mayor. Key findings: - 74% of SF voters approve of him - Majorities support his handling of public safety, downtown revitalization, neighborhood cleanliness - He earns support from across the political spectrum
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Robby Allen retweeted
The only companies firing people b/c AI makes them so wildly productive also share these attributes: - over-hired during COVID - are market share losers - have giant capex spend What a delightfully curious coincidence
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Robby Allen retweeted
The NBA has declined more than any major sport in recent years. Analytics have effectively solved the game, driving a playing style that’s repetitive, less interesting to watch, and contributes to player injuries. By the end of the season, it’s a Hunger Games outcome (survival over winning) where the team with the uninjured players wins. Gambling influence and intentional team tanking have made the integrity of the sport increasingly questionable. These issues have been obvious for years, and management has done little to address them. Instead Adam Silver, the NBA commissioner, is rewarded with a board chair position at Duke - which underscores the lack of merit and competence behind a declining institution.
Just in: Minnesota Timberwolves star Anthony Edwards has sustained a bone bruise and hyperextension in his left knee and is expected to miss multiple weeks, sources tell ESPN. Results showed Edwards avoided any ligament damage, but he will now miss time.
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Robby Allen retweeted
I've seen a few AI 'platform' RFPs from enterprises lately. Head scratcher. 3-4 month process. By then it's out of date — two or three model releases, products that didn't exist when they started. Then a 6-month rollout. Tells me who the winners and losers will be straight away.
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Robby Allen retweeted
If you feel like Anthropic is going after every enterprise software market and that the big SaaS enterprise platforms like Salesforce, ServiceNow and Workday are toast, you are wrong. This simplistic thinking fundamentally misunderstands the difference between an AI Agent and the Enterprise Platform. Let me explain: > An AI agent executes tasks. An enterprise platform defines, orchestrates, and gives the agent context to execute that task. > An AI agent has access. An enterprise platform governs agent permissions. > An AI agent can act. An enterprise platform can audit, control, and enforce. > An AI agent may go rogue. An enterprise platform guarantees compliance deterministically. > An AI agent is powerful in isolation. An enterprise platform is powerful in coordination across teams and business units. Furthermore, an enterprise platform can be multi-model, multi-cloud, and multi-integration. It is future proof for the customer in a dynamic market. CIOs buy Enterprise Platforms and will continue to do so, as long as those platform deeply integrate AI Agents within deterministic, governed, auditable, business processes.
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Robby Allen retweeted
Another week on the road meeting with a couple dozen IT and AI leaders from large enterprises across banking, media, retail, healthcare, consulting, tech, and sports, to discuss agents in the enterprise. Some quick takeaways: * Clear that we’re moving from chat era of AI to agents that use tools, process data, and start to execute real work in the enterprise. Complementing this, enterprises are often evolving from “let a thousand flowers bloom” approach to adoption to targeted automation efforts applied to specific areas of work and workflow. * Change management still will remain one of the biggest topics for enterprises. Most workflows aren’t setup to just drop agents directly in, and enterprises will need a ton of help to drive these efforts (both internally and from partners). One company has a head of AI in every business unit that roles up to a central team, just to keep all the functions coordinated. * Tokenmaxxing! Most companies operate with very strict OpEx budgets get locked in for the year ahead, so they’re going through very real trade-off discussions right now on how to budget for tokens. One company recently had an idea for a “shark tank” style way of pitching for compute budget. Others are trying to figure out how to ration compute to the best use-cases internally through some hierarchy of needs (my words not theirs). * Fixing fragmented and legacy systems remain a huge priority right now. Most enterprises are dealing with decades of either on-prem systems or systems they moved to the cloud but that still haven’t been modernized in any meaningful way. This means agents can’t easily tap into these data sources in a unified way yet, so companies are focused on how they modernize these. * Most companies are *not* talking about replacing jobs due to agents. The major use-cases for agents are things that the company wasn’t able to do before or couldn’t prioritize. Software upgrades, automating back office processes that were constraining other workflows, processing large amounts of documents to get new business or client insights, and so on. More emphasis on ways to make money vs. cut costs. * Headless software dominated my conversations. Enterprises need to be able to ensure all of their software works across any set of agents they choose. They will kick out vendors that don’t make this technically or economically easy. * Clear sense that it can be hard to standardize on anything right now given how fast things are moving. Blessing and a curse of the innovation curve right now - no one wants to get stuck in a paradigm that locks them into the wrong architecture. One other result of this is that companies realize they’re in a multi-agent world, which means that interoperability becomes paramount across systems. * Unanimous sense that everyone is working more than ever before. AI is not causing anyone to do less work right now, and similar to Silicon Valley people feel their teams are the busiest they’ve ever been. One final meta observation not called out explicitly. It seems that despite Silicon Valley’s sense that AI has made hard things easy, the most powerful ways to use agents is more “technical” than prior eras of software. Skills, MCP, CLIs, etc. may be simple concepts for tech, but in the real world these are all esoteric concepts that will require technical people to help bring to life in the enterprise. This both means diffusion will take real work and time, but also everyone’s estimation of engineering jobs is totally off. Engineers may not be “writing” software, but they will certainly be the ones to setup and operate the systems that actually automate most work in the enterprise.
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Land and expand
What $9B→$30B looks like up close: more customers crossing $1M, and inside each one, more teams pulling it in because the first team's results are visible. Then the CEO asks who else can use more. I've never seen spend get deliberately accelerated like this.
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Robby Allen retweeted
From The Score Will Take Care of Itself:
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