Joel Shackleton
6.7K posts

Joel Shackleton
@JoelShackleton
Father | Husband | Portfolio Manager @ RBC DS & RM Pod My business is helping Canadian families manage generational wealth | CIM®








Let's hope this translates into Albertan in the way the PM is intending.

Five months in, I think I've decided that I don't want to vibecode — I want professionally managed software companies to use AI coding assistance to make more/better/cheaper software products that they sell to me for money.

Spotify TTM Free Cash Flow


Bill Ackman says this is a good environment to deploy capital. We’re still in the earliest innings of the AI economy and what may become the largest industrial buildout in human history.


Introducing workspace agents in ChatGPT—shared agents that can handle complex tasks and long-running workflows across tools and teams.



The amount of hype and BS going around about enterprise AI adoption is insane. Aaron @levie is the most AI forward-thinking CEO in public markets today. But even Aaron at $1BN+ in ARR is valued at $3.3BN and getting smashed by Wall St. I sat down with Aaron to understand WTF is happening, what is real and what is fake in enterprise, WTF to do with token budgets and wrote up my notes below. (Link to full episode in comments) 1. Why Dwarkash Was Wrong and Jensen Was Right on Upgrading Systems Upgrading software is a multi-year effort, not a "magical moment" where everything can be secured overnight. The reality of enterprise security is an ongoing, endless cycle of "leapfrogging" between defensive and offensive capabilities. Founders must realize that even with access to frontier models, the implementation cycle in the real world remains the primary bottleneck. 2. Why We Will Have More Lawyers in Five Years Not Less The industry is myopic about job elimination; AI makes it easy to generate content, but it hasn’t made it easier to get that content approved by a court or a patent office. As clients inundate lawyers with AI-generated contracts and memos, the "ultimate constraint" becomes the number of qualified humans available to review and approve the output. 3. What Role Does Not Exist Today That Will Be Incredibly Common in Five Years? We are about to see the creation of 500,000 to 1 million "Agent Operators". These technical-yet-business-savvy individuals will be responsible for "care and feeding" of agents—writing skills, understanding MD files, and redesigning workflows for agents rather than people. 4. Will Massive Software Providers Simply Be Turned Into a Database That Agents Crawl Over? While the user interface may shift to chat, the value is moving to the API layer and the "business logic" embedded above the database. Systems like ERPs are more than databases; they contain decades of complex logic for supply chains and accounting that agents must interact with, not replace. 5. What Everyone Thinks About Enterprise AI Adoption That They Get Wrong The assumption that the massive gains seen in AI coding will immediately translate to all other knowledge work is a "misread". Coding has specific idiosyncrasies that don't always exist in broader knowledge work, where human collaboration and regulatory loops are more complex. 6. Where Would You Be Investing if You Were a VC Today? Despite high valuations, Levie would still be "loading up" on frontier rounds. These companies have the potential to grow much larger because the ultimate market for AI is often larger than the industry currently realizes. 7. The Budget of Tokens Will Have to Move Out of IT Spend and Into Opex Enterprise AI shouldn't be treated as a tradeoff between software licenses. Instead, token budgets will move into regular operational expenditure (OPEX), where businesses trade off a marketing campaign for a more productive, automated marketing engine. This allows AI companies to tap into a massive pool of capital beyond the traditional, capped IT budget.

What Role Does Not Exist Today But Will Be So Common in Five Years Time: "500K-1M jobs will be created for agent operators. This person will be somewhat technical. They will be deep in the AI world. They're gonna have to understand MCPs and CLIs and they are going to have to know how to write skills. It's going be this group of people that will know how to go into your marketing team or your legal team, or your operations team, or your life sciences research team and this is the person that is basically going to enable that function to get leverage from agents." @levie Where is this right? Where is this wrong? @jasonlk @gregisenberg @amasad @AnjneyMidha


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