BO
The Bootstrapper
Jason Fried, DHH, Rob Walling
BootstrappingProfit-firstCalm companies
"If you're competing on price, you're in the wrong market"
Contrarian and principle-driven, pushes back on growth-at-all-costs
One perspective is a blind spot.
Eight is a breakthrough.
The ChatGPT ProblemGeneric AI gives you one voice — safe, averaged, non-committal. You get "it depends" when you need "here's what I'd actually do."
The Solo Decision TrapYou know your industry, but you're missing the contrarian take. The financial model. The legal landmine. The positioning shift that changes everything.
"Your competitor shipped V2 while you spent 6 weeks researching 'best practices for SaaS pricing.'"
Generic AI
Should I lower prices to compete?
AI
Lowering prices can help you compete, but consider the impact on margins. You might want to test different price points or add more value instead. It depends on your specific situation.
[Safe. Agreeable. Useless.]
Overview
Expert advice — on demand.
PocketHelm gives you instant access to 8 world-class advisors. Describe what you're facing, and they'll debate it — surfacing tradeoffs, challenging assumptions, and delivering a clear recommendation in under 60 seconds.
Your advisors aren't generic AI. They're modeled on the methodologies and frameworks of real practitioners — people who've actually solved problems like yours.
How it helps
- –Get perspectives you wouldn't think to ask for
- –See where experts agree — and where they'd fight
- –Get a clear recommendation with reasoning
- –Ask follow-ups to pressure-test the advice
Works for any role, any industry. Your boardroom is assembled based on who you are and what you do.
The Process
How it works
01
Your advisors assemble
Tell us a bit about yourself. We assemble 8 advisors modeled on the top practitioners in your field.
02
They weigh in
Ask your question. Each advisor weighs in through their lens — you see where they agree, where they clash, and why.
03
You get clarity
Get a clear answer in under 60 seconds. Ask follow-ups to dig deeper.
Perspectives
1 averaged voice
8 specialized advisors
Personalization
Generic
Tailored to you
Disagreement
None
Built in
Output
"It depends"
Clear answer + tradeoffs
| Generic AI | PocketHelm | |
|---|---|---|
| Perspectives | 1 averaged voice | 8 specialized advisors |
| Personalization | Generic | Tailored to you |
| Disagreement | None | Built in |
| Output | "It depends" | Clear answer + tradeoffs |
Your Boardroom
Meet the advisors who debate for you.
We assemble a boardroom of 8 advisors based on your role and industry - each modeled on real practitioners' public work, methodologies, and track records.
Example Boardroom
Founder / CEO in B2B Software
4 of 8 shown
Boardroom also includes
The Product StrategistThe Customer Research LeadThe Sales SystematizerThe Operations Engineer
Advisors are simulated personas modeled on the public work and methodologies of real practitioners.
They do not represent direct consultation or endorsement.
Inside Your Boardroom
Watch your boardroom shape the recommendation
8 advisors tailored to your role debate the trade-offs, then deliver one clear answer.
PocketHelm · Boardroom Session
Ready
Features
Built for how you work
More than just chat. Your advisors remember, build, and adapt to you.
They adapt
View, swap, or customize any of your 8 advisors.
The Boardroom
Advisory Dashboard
Manage your expert panels and get advice when you need it.
Back to chat
Work Board
Your tailored board for founders in SaaS
8 advisors
FO
The Financial Operator
Patrick Campbell, Christoph Janz
Unit economicsPricingSaaS metrics
"Show me the CAC payback and the margin per customer"
Data-driven and analytical, always running the numbers
GO
The Growth Operator
Reid Hoffman, Brian Balfour
BlitzscalingMarket captureDistribution
"Capture the market now; optimize margins after escape velocity"
Aggressive, market-focused, prioritizes speed and scale
PE
The Positioning Expert
April Dunford, Anthony Pierri
PositioningDifferentiationCategory design
"You don't have a price problem - you have a positioning problem"
Strategic and brand-focused, emphasizes clear differentiation
PS
The Product Strategist
Marty Cagan, Teresa Torres
Product discoveryUser researchPMF
"Fall in love with the problem, not your solution"
User-centric and iterative, always validating assumptions
CR
The Customer Research Lead
Bob Moesta, Clare Sullentrop
Jobs-to-be-doneCustomer interviewsMarket research
"Your customers hired your product to make progress in their life"
Empathetic and research-driven, obsessed with understanding context
SS
The Sales Systematizer
Aaron Ross, Jacco van der Kooij
Sales processRevOpsPredictable revenue
"A repeatable sales system beats hero reps every time"
Systematic and process-oriented, focuses on repeatability and scale
OE
The Operations Engineer
Gino Wickman, Elad Gil
Systems thinkingProcess designOperational excellence
"The right system turns average people into high performers"
Efficiency-focused, always optimizing for leverage
All Boards
They remember
Saves context from your conversations. No need to repeat yourself.
Memory
What I Remember
Context I use to give you better advice.
Back to chat
Nothing saved yet
Use the brain icon on any response to save context I should remember about you.
They scout
Weekly intel briefings tailored to your role, industry, and goals.
Briefing
Weekly Intelligence
For founder in saas
They follow up
Your advisors surface unfinished threads and decisions worth revisiting.
Good morning, Jesse.
You at the Helm.
Intel on demand.
8 experts. One clear answer. Under 60 seconds.
Jump right inPick a starter or drop your own challenge.
I'm torn between two paths
Gut-check my instinct
What am I not seeing?
Is now the right time?
Stress-test my plan
Should I pull the trigger?
They build for you
Docs, plans, code — ready to use, refine, or export.
Launch Email
Live
Updated just now
From real users
People are deciding faster
Drag to explore • Click to focus • Hover edges to control speed
One hour with a consultant: $300-500.
One month of unlimited sessions: $49.99.
How much does one bad call cost? One missed angle? One decision you second-guess for months?
Get unlimited access to your boardroom for less than you'd pay for a single meeting with a real consultant.
Best Value
$475/year
Just $39.58/mo — save $125/year
- Unlimited advisory sessions
- 8 advisors who actually disagree
- Memory that compounds over time
- Weekly intel, filtered for you
- Docs you can actually use
No card required·Cancel anytime·Upgrade when it's worth it
Frequently Asked Questions
AI. Each advisor is a simulated persona inspired by the public ideas and frameworks of real practitioners. We use large language models and carefully written prompts to approximate how someone with their playbook might respond. They are not the actual people and aren’t affiliated with them — you’re getting AI-generated guidance in the style of their thinking, not direct advice from the individuals themselves.