The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 76 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Wilkinson: Employees are unreliable and fail to understand founder vision
“You know, if I was using employees they're unreliable. They don't see my vision. They don't understand every aspect of design.”
Wilkinson: Basic businesses will be fully run by AI in 3-6 months
“And I think that we're probably three to six months out from being able to just can businesses off to AI to run at least basic businesses like this.”
Wilkinson: ChatGPT will eliminate software middlemen by building tools on demand
“For all tools basically all middlemen businesses are gone. And I believe fundamentally that we are all going to go to the search bar and the new search bar is ChatGPT and you're going to query it and ChatGPT will just build whatever you need or it'll hook into…”
Wilkinson: Built and Runs a SaaS Business Entirely Autonomously via OpenClaw
“And so as a test, before I started doing this in our operating businesses, I basically built a business a SaaS business, and then I've been running it entirely autonomously using OpenClaw.”
Wilkinson: Customer support will not be a human job very soon
“Like support to me is not a job very, very soon.”
Wilkinson: Anthropic and OpenAI will soon launch AI CEO products
“My, I mean, my kind of belief is like pretty soon Anthropic and OpenAI are gonna launch like basically like CEOs. So you just be like, I'm just gonna hire a CEO for my company. Give me your data. I'll figure it out. I'll run it. I'll run the whole business.”
Wilkinson: Software Will Face Extreme Pricing Pressure Like Restaurants
“I think pricing pressure is just gonna go crazy because it's like the restaurant industry. Like, you know, restaurants are not a bad business. They're bad because there's too much competition.”
Wilkinson: Software is a worse business now than five years ago
“All I can say is software is a worse business now than it was five years ago.”
Wilkinson: Holding company spends $40k/month on Claude instead of hiring
“So instead of a payroll, we just have a 40,000 dollar a month Claude bill. And it's doing everything.”
Wilkinson: AI-built custom software will collapse vertical SaaS pricing power
“And I think the new world is, you know, if. 400 people in the United States own funeral homes, let's say like 20 of them are smart and no AI, they're all going to build their own software. And so what does that do? That means It's great for the consumer. There…”
Wilkinson: Any software product that is just an API call is cooked
“It's like anything that could be an API call is just cooked. So to me, that's like an API call business. That's like the first thing to get run over.”
Wilkinson: Chris Anderson is currently shopping TED for sale
“You know, Ted is for sale right now. Maybe you should buy that. Is that for real? Yeah, it's for, I think it's public knowledge right now. They're shopping it around and he's going to give it, I think he's going to give it away to whoever is going to be the be…”
Wilkinson: Device controllers like Apple will capture most consumer AI value
“The people that will ultimately capture a lot of this value are going to be whoever controls the devices. Because I do believe like a lot of these LLM a lot of this functionality will ultimately be implemented.”
Wilkinson: Almost all current AI businesses will be zeros in five years
“To be clear, I'm still saying almost all these businesses will be zeros in five years.”
Wilkinson: Athletic Greens is 'too big to fail' due to creator incentives
“I think that it's too big to fail in that there's too many people making too much money from it that they all want it to keep going. You know, like Sahil or Huberman or any of these people that do this, that talk about AG one. They want it to persist, right? C…”
Wilkinson: Raising from Sequoia brings intense pressure that ruins founders' lives
“Like Sequoia who are like the most intense MFers in the world just joined the board. They're going to hold a gun to that person's head and say, you need to grow your company, 300% a year. You need to spend as much money as possible to go there, and that CEO's …”
Wilkinson: Creativity is compromised by the number of intermediaries in execution
“And I think that creativity is just compromised based on how the number of people between your vision and execution.”
Wilkinson: 5M to 10M context windows will enable AI-run companies
“And I feel like once the context window is like 5,000,010 million, then we'll be able to run entire companies with this.”
Wilkinson: OpenClaw agents still require micromanagement, not true delegation
“Like I think open claw agents are still like zap. They're basically like zap your zaps, but that can make basic decisions and have intelligence, but you still have to tell them step by step. This is how I want you to think. This is how I want you to operate. L…”
Wilkinson: AI is incredibly accurate at interpreting psychological screening tests
“Like I'm using psychological screens that are supposed to be interpreted by a psychologist, but I'm not a psychologist. I'm using AI to do it. And I think it's incredibly accurate.”
Wilkinson: A 'Her'-style AI assistant will be built within years
“I've basically just accepted that I'm going to live in Claude code until somebody builds her which I'm sure is coming in the next couple of years.”
Wilkinson: Software Creation Is Effectively Free and Highly Reproducible
“Now I just think software is free. Anyone can make it. Anyone can rip it off.”
Wilkinson: Home services and brick-and-mortar face robotics risk in 10-20 years
“I'm either buying like something with a moat, which is very, very hard to find certainly in technology right now home services, businesses, like very, very brick and mortar kind of stuff. But even that I think is at risk with robotics over the next 1020 years.”
Wilkinson: Many previously high-quality businesses are now 'cigar butts'
“And I think a lot of previously high quality businesses that would be like a gourmet cigar from a cigar shop are now cigar butts.”
Wilkinson: Non-technical CFO built portfolio tracking tool in one week via Claude
“But anyway, this was built by my CFO. He's never coded in his life. Like when I told him about cloud code and that he should check it out, he's like, I don't know how to code. Like I'm not technical. And literally within like a week, I'm so lucky that he's the…”
Wilkinson: Addepar will not be able to sustain premium pricing much longer
“I don't think that they're going to be able to do that for too much longer because there's going to be a lot of competition that comes out. Hopefully somebody watches my video and says, I'm going to build this too, and then go crush Adapar.”
Wilkinson: Prompt engineer jobs are unnecessary because AI can interview users directly
“Nobody needs to build the prompts. The AI should just interview you. OpenAI just doesn't want to spend all the compute at this point, but it is fully capable of just interviewing you to figure out what you need.”
Wilkinson: AI is a sustaining innovation that drops costs, not a moat
“In a lot of instances, it's like a sustaining innovation, right? And what I mean by that is it's a new technology that will drop the cost.”
Wilkinson: Building $1M startups and losing equity has never been easier
“It's never been easier to build a million dollar business and it's never been easier to lose all your equity value.”
Wilkinson: Building around Anthropic's Model Context Protocol is a massive opportunity
“I actually think that might be like my first million kind of opportunity for somebody to really do MCP right.”
Wilkinson: Claude found $100,000 in tax savings from my Xero data
“Like at one point I said how could you optimize my taxes? And it said, oh, you have a credit line over here and you have a credit line in your company. If you use the company money to pay down the personal credit line, you can just immediately write off. Like,…”
Wilkinson: 1Password's moat is trust and uncompromised security, not software complexity
“Like think about like one password is not hard. Like anyone can vibe code one password. What matters about one password is everybody knows one password has not been compromised and they trust.”
Wilkinson: AI search will scrape affiliate directories without passing traffic or links
“And so if you build an affiliate directory, they're just going to scrape that and then it'll inform the results and you'll never get your links in or credit or anything like that.”
Wilkinson: Buying rural ranches for remote work overlooks logistics and isolation
“I think it sounds like a dream, but I think it's oversimplification. I think it's like saying like, oh, I'll have a baby and it's going to be awesome. Cause it's going to have cute little feet and it's going to look like me. And they're not imagining two AM wa…”
Wilkinson: There is no upside to following real-time news
“I just don't think there's any upside in looking at what's happening in the moment.”
Wilkinson: Moving to San Francisco would have prevented building a profitable business
“I don't think I'd have a profitable at scale business today if I had moved to San Francisco.”
Wilkinson: A couple million dollars affords top-tier life in Victoria
“If you're in Victoria, if you can get a couple million bucks together, you can basically have the best life of anyone in town. And there's just not this endless ladder of achievement.”
Wilkinson: Reinvesting 80% and compounding creates more wealth than VC unicorns
“Once I understood compounding and I could do basic math, I realized that I was going to be way wealthier than any of the people that I knew, even the people who had billion dollar companies, because I just knew that if I was compounding my capital and reinvest…”
Wilkinson: AI Agent Productivity Tooling Sinks 80% of Time into Maintenance
“And the problem is that I feel like I'm spending 50% of my time debugging it and 50% of my time, maybe 30% of my time making it better and then 20% of my time being productive. So it's like the classic productivity treadmill.”
Wilkinson: Family office invested $16M across 132 venture bets, now worth $36M
“I can see that I've made 132 direct investments. I invested sixteen million. It's now worth thirty six million.”
Wilkinson: Tiny Intervenes in Software Portfolio Businesses Over AI Risk
“The challenge in tiny is that we
Are generally pretty hands off and where we're really leaning in is in a lot of the software businesses, because those are the ones that are at the most risk.”
Wilkinson indexed his email archive in GBrain to profile contacts
“Basically what I did is I ingested all of my email and I said, Hey, I want you to go through my email a thousand at a time and I want you to draw connections and I want you to build pages for everybody that I know. So basically I have a page on Every, every pe…”
Wilkinson Records Daily Audio to Contextualize AI Agents via GBrain
“And so I record my entire day and then G brain ingests it and it just knows context. And then my open claw agents have full context.”
Wilkinson: AI Health Agent Detects Nerve Pain Flares via Wrist Temperature
“And then I have this weird viral nerve pain that I get. And it looked through my data over the last five years and said, oh, I've correlated it. And I see that every time you get that flare, Your risk temperature changes for three days before. And so it tells …”
Wilkinson: AI Health Agent Simulates Multi-Doctor Team for Medical Inquiries
“If I ask it a question, it's prompted to use max intelligence. So let's say I said Hey, should I take this medication? It will spin up a rheumatologist, a you know internist, like every type of doctor as a clod expert with extra high thinking, and it will do a…”
Wilkinson: Prompting AI to use eight sub-agents delivers superior results
“I also highly recommend using agent teams. So I'll say always use a team of agents of eight sub agents. And I find the answers are just incredible.”
Wilkinson: Standalone apps like Cal AI will face 100 clones within months
“There's tons of those, but there's going to be like a hundred of them in the app store in like two months. And then Cal AI will not be able to charge what they are.”
Wilkinson built an automated local newsletter with Lindy AI in an hour
“I recently, I own like a local newsletter business and I was goofing around with Lindy and I was able in about an hour to build a Lindy agent that could go through. It would basically like choose this. I chose a city like a city near me. And I said, every day …”