Derek Sivers
CD Baby founder · contrarian minimalist
“Hell yes or no.” Filters every choice through radical simplicity and customer delight.
A decision-making studio · coming soon
Bring your hardest call to a panel of minds you trust. They argue it out in rounds — positions, rebuttals, a real vote — and hand you a verdict, the dissent, and the why. You write the question in plain Markdown; they do the thinking.
No login. No noise. One email when it's ready.
## Should we raise prices 20% this quarter?
The biggest calls in a small business — pricing, hiring, a pivot, a launch — get made on a gut feeling and a quick poll in Slack. They deserve a real room.
How it works
State your decision in a plain text file — the kind you'd type into any notes app. Add as much context as you like. No code, no setup.
## Should we hire a second salesperson now?
We're at $42k MRR, one founder selling,
pipeline is full but follow-up is slipping…
Choose advisors whose judgement you trust — each one carries a real thinker's frameworks, biases, and vocabulary. Three to five is the sweet spot.
Each advisor writes a position. Then they read each other's and push back. Minds change. You get a final vote, the sharpest dissent, and the reasoning behind both.
The deliberation
Single answers flatter you. A real board disagrees, defends, and occasionally changes its mind in the room. advisors.chat runs the rounds so the friction actually happens.
The right advisors for this question are chosen — and you approve the lineup before anyone speaks.
Every advisor argues their stance in their own voice, with numbers — cost, upside, risk — and an opening vote.
They read each other and push back — who's wrong and why. Some change their vote. You get the honest tally.
Meet the board
Start from a roster of sharp, distinctive thinkers — then add the voices you wish were in your corner. Each advisor reasons the way the real one does, not as a generic chatbot.
CD Baby founder · contrarian minimalist
“Hell yes or no.” Filters every choice through radical simplicity and customer delight.
AngelList founder · philosopher-investor
First principles, leverage, and the long game of compounding.
Author, $100M Offers · revenue-obsessed
“Price is only an issue in the absence of value.” Math over vibes.
Pro poker champion · author, Thinking in Bets
Separates decision quality from luck. Probabilities, not certainties.
Product discovery coach
“What evidence do we have this solves a real problem?” Kills the build trap.
Indie maker · @levelsio
Ship the imperfect MVP today. Let the market decide what survives.
Farnam Street · author, Clear Thinking
Mental models and systems that beat willpower and reaction.
MicroConf · author, The SaaS Playbook
Sustainable revenue over venture-scale dreams. Founder-first.
A mentor, a hero, a board member you wish you had. Describe them once; seat them forever.
What you walk away with
Every position and rebuttal in full, a vote tracker showing who moved, the key tensions, and a clear recommendation.
Sliders for the assumptions that matter — price, conversion, hours — that recalculate the impact live and show the votes shift.
Print-clean and ready to drop in front of a co-founder, a partner, or your own future self when the doubt creeps back in.
Who it's for
Founders, solo operators, agency owners, and prosumers making the calls that don't fit in a spreadsheet — and don't warrant a $500/hour consultant. The decisions where being half-right is expensive.
The boardroom,
in a file.
advisors.chat is opening soon. Leave your email and you'll be among the first in the room.
Get notified at launch