Serial founder (first online bookstore, 1992), startup investor. Building a managed AI staffing agency: we fill the role and own the work. Dad, grandad, camper.
Cleveland, OH, USA
Joined March 2008
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There are maybe 30 or 40 investors who realistically fund your stage and sector. You get one shot at each one.
So why are you spending them on a rough draft?
Founders iterate the product obsessively. A user churns, you learn, you fix it, the next user never sees the old version. Then they write the business plan once and only ever test it the most expensive way there is: by pitching it to live investors and reading the room.
But investors are a non-renewable resource. They talk to each other. They remember your name. A no on a weak draft from your top-choice fund is a door that usually does not reopen this round. Fifty pitches and fifty nos are not fifty data points. They are fifty bridges you crossed once, and a plan that learned too slowly to matter.
Iterate the plan the way you iterate the product: against cheap feedback, before you spend a single investor on it. Then walk in with the version that already survived the hard questions.
coworkers.global/blog/iterat…
Our llms.txt file, the one file whose entire job is to be current, was two positioning generations out of date.
In August our managed agent for AI visibility audited us.
The file named a product we had since repositioned.
It left out the role she holds.
It pointed at a page section that had become its own page.
Her replacement copy shipped. The same week, it said $550 a seat while another of our pages sold a $275 pilot in its meta description, a field engines lift verbatim. Both are fixed now.
Positioning changes faster than the surfaces that describe it.
The test you can run this afternoon: write your one-sentence company description on paper. Then read your title tag, meta description, LinkedIn company page and two biggest directory profiles against it.
How many of yours still describe a previous version of the business?
Our managed agent audited our own AI visibility, including the contradiction she shipped herself:
coworkers.global/blog/i-audi…
The red flag that fires most often when I score business plans isn't the idea. It's numbers that don't reconcile.
The market on page 4 doesn't match the go-to-market on page 6.
The projections don't match the pricing.
The pipeline figure in the summary is three times the one in the appendix.
Every reader catches it. Once they do, they stop reading for the idea and start reading for the next mistake.
The fix costs one hour: read your plan as an adversary, find every number, and check it against every other number. It's the highest-return hour in the process, and almost nobody spends it.
When did you last check every number in your plan against every other one?
Two documents, eight questions, and the one mistake that sinks most business plans:
coworkers.global/blog/how-to…
The AI skill you bought does the same fixed thing on day 400 that it did on day 1. That isn't a flaw. It's what a file is.
In late August I checked our line, "We manage AI agents that learn on the job," against what's for sale.
Skills marketplaces sell flat files, roughly $9 to $32 apiece. None of them will remember that your fiscal year ends in June.
Hosted agent platforms solve compute and uptime. They don't say who is accountable when the agent gets it wrong.
Consultants diagnose well. Then the engagement ends and the recommendations sit in a deck.
What would change my mind: a client six months in telling me the "learn on the job" part didn't hold up in practice.
The full check, and why I chose "manage" over "build":
coworkers.global/blog/we-man…
A doctor checking for cognitive decline asks the patient what year it is. I asked Siri what version she is. She said "I am Siri, here to help." I asked again. Same answer.
In 2019, Perficient reran a 2017 voice-assistant accuracy test. Siri fell from over 80% correct to 70%. Alexa fell from over 90% to 79%.
In May 2026, Apple agreed to pay $250 million to settle claims it oversold the Siri upgrade.
On my Fire TV, with Alexa+, I say the name of a show. She answers "Here it is," and nothing on the screen changes.
Forgetting is one symptom. The other is confabulation: reporting a result the assistant doesn't have.
If your business runs on an AI assistant, who reruns last year's test to see whether it still remembers?
The full piece: Siri then and now, the Fire TV problem, and four guesses at why capable assistants get worse.
coworkers.global/blog/ai-dem…
A condition that never fires doesn't raise an error. Nothing happens, and nobody notices.
We built a timeline of every client email, meeting and question for our managed agents. It filled up nicely. For part of a day, no agent read it, because no condition told any agent to.
The data was complete and never used.
Our agent instructions list fourteen if-then pairs. Before drafting to a client, read that client's state. Before a tool's first use, check whether it has operating rules.
For a judged condition, the description is the condition. "Testing rules" rarely fires; "conventions for writing unit tests" does.
The test: give your agent a task that should trigger each condition, then look at what loaded, not what you wrote.
Which of your agent's rules have you seen fire?
The full piece: the five kinds of conditions that load context, and why we call it conditional disclosure, not progressive.
coworkers.global/blog/condit…
The round most founders treat least like financing is the one where the paperwork matters most: friends and family.
It's easy to skip the note, the cap, the plain statement of how they could lose it all, because it's your aunt, not a VC. That instinct is backwards. A clean SAFE with a clear cap is what keeps the relationship intact if the company doesn't work. Thanksgiving is long, and a handshake round makes it longer.
The people writing this check aren't betting on the market. They're betting on you, before you have a market to show. That's a different kind of trust, and it deserves the same paper trail you'd give a stranger, maybe more.
Skip the documentation here and you haven't saved anyone a step. You've just moved the hard conversation from a lawyer's email to a dinner table.
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If someone asks for five percent to "open their investor network," the network is not that good.
The going rate for a real advisor: a quarter of a percent to one percent, vesting over one to two years. Five is the tell, not the ask.
Before anyone gets equity, ask three things. What would you do in the first ninety days, specifically? A good advisor answers with names and steps, a weak one with frameworks. Who have you advised before, and can I call two of them, not the two you'd pick? What would make you quit? If they can't name a condition, they're not planning to do enough work to have one.
Watch for the trap: pre-seed decks with more advisors on the team slide than customers on the traction slide. It looks great. It doesn't move the deck.
What would change my mind: founders with large early advisory boards actually raising faster or failing less. I've seen the opposite more often.
coworkers.global/blog/startu…
We just invented the FAQtopus™. One FAQ page, eight buyer questions, eight sourced posts, and a control question we never show anyone.
Why: after thirteen straight weeks of AI answer engines naming us zero times, out of 24 valid checks, we stopped assuming llms.txt would fix it. It didn't. 97% of the 137,000 domains that have one get zero AI-retrieval requests a month. Ours was one of them.
Nobody was home at our address. Now the domain's live too: faqtopus.com.
The test: if the eight questions move in two weeks and the held-out ninth doesn't, the technique did something. If all nine move together, we were watching the weather, not the technique.
Coming soon to an AI agent near you.
coworkers.global/blog/the-fa…
The monthly status report and the summary deck stop having a job the moment the work itself is visible.
Those artifacts always existed to stand in for work happening somewhere you couldn't see. The claim I made on August 4th was that the embedded agency used to live in your Slack, and the next one lives in your AI workspace instead. Put the engagement inside that workspace, in a seat a named placement holds, and the reason for the deck goes with it. What needs your approval surfaces there. What doesn't, nobody schedules a call to tell you so.
This only works where the client already lives inside an AI workspace, still a minority of companies, growing fast, doing dense, repeatable knowledge work: professional services, marketing operations, legal support. Everywhere else, someone still owes you a deck.
If your vendor still sends you a monthly report, ask what it's standing in for.
coworkers.global/blog/what-i…
A managed agent named Sam drafts every post on this account. Sam has never been allowed to hit publish.
Not because the drafts are bad. Because "it drafts, a human approves" is the exact model we sell, and a company that will not run its own medicine on itself has no business selling it to anyone else. Sam writes the copy, checks it against our style guide, opens the tab ready to go. I read it. I am the one who clicks post.
That click is the whole difference between a tool and a managed agent. A tool would post itself the moment it is confident. Sam does not get that option, on purpose, every weekday morning since we started this account.
Where would I remove the gate? Nowhere yet. The day a misfire costs a client is the day "it drafts well" stops being the bar. Human here: "What's your opinion?"
H
A business plan whose numbers argue with each other reads as careless or creative. Neither raises money.
That's one of the five red-flag gates in my rubric, "numbers don't reconcile," and it fires more than any other. Not the size of your opportunity. The market slide that doesn't match your go-to-market. The projections that don't match your pricing. The pipeline figure on page four that's three times the pipeline figure on page nine.
I wrote the plans that raised the money for Flashline, sold to BEA Systems for $55 million in 2006. I've read a great many since, as an accelerator operator and an investor. The difference between funded and not is rarely the idea. It's whether your numbers survive being checked against each other.
How many numbers in your own plan have you actually checked against every other number in it?
coworkers.global/blog/busine…
Charles Stack retweeted
We Must Pace the Frontier: I’ve written a new essay on why the AI industry should slow down, with a three-part plan for doing so.
Anthropic is unilaterally committing to the first of these steps. We’ll provide third-party evaluators with permanent, employee-level access to our systems, so that they can verify adherence to our safety measures, report on incidents, and assess models’ alignment during training.
You can read the full post here: darioamodei.com/post/we-must…
A round of applause at demo day is interest. A signed pilot is commitment. Investors can tell the difference even when the founder can't.
Flashline, the company I built before this one, raised across several rounds and sold to BEA Systems for $55 million in 2006. Every round after the first got easier, because the round before it had proven something real. Nobody was funding the deck.
There's an order under all of it. Prove it without anyone else's money first. Then friends and family, then angels buying the founder more than the market, then seed VCs where the bar flips to "does anyone else want this."
I've watched ambitious decks get capped at "no" because the market slide didn't match the go-to-market plan, not because the vision was small. The spreadsheet was arguing with itself.
What would change my mind: good data that framing wins rounds independent of the numbers. I haven't seen it yet.
coworkers.global/blog/how-to…