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Your idea sounds great. That’s what worries us.

Type out your startup idea or big decision. Devils Advocate asks the awkward questions, brings receipts from failed startups and 2,000 years of philosophy, then hands the decision back to you. You’re the boss. We just read the fine print.

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Private beta opens . No spam. We save the arguing for the product.

You:

I’m building food delivery for college hostels. The big apps made it, so will I.

Devils Advocate:

Love the confidence. Quick question first: who’s paying? The students, or their parents’ wallets?

Devils Advocate:

Also, the big apps are the survivors. We found three hostel-delivery startups that didn’t make it. Want to meet them?

Source: 3 similar startups, why they shut down, sources linked

Devils Advocate:

Your call. Always.

An illustration of a sample conversation.

What are you bringing? The rest of the page changes to match.

Challenge my decisionFor big life calls and the beliefs you’ve never questioned.

Challenge my ideaFor startup ideas, side projects, and work proposals.

Try a sample debate

Devils Advocate: Pick a sample, then tap your answers and watch it argue back. Every reply is written in advance, so there’s nothing to type. The real thing argues with whatever you bring.

Devils Advocate

Challenge my decision

  1. Your decision
  2. Questions
  3. Real question
  4. Both sides
  5. Push back
  6. Hand-back

  1. Devils Advocate: What’s the call you’re trying to make?

  2. You: I’m skipping placements to build my startup full time. I’ll regret it forever if I don’t try.

  3. Devils Advocate: What would you lose if it fails in 12 months?

  4. You: A year and some savings

  5. Devils Advocate: A real cost, but a recoverable one. Seneca’s advice: rehearse the worst case, and it loses its grip on you.

  6. Devils Advocate: Does anyone depend on your income?

  7. You: No, just me

  8. Devils Advocate: That’s freedom, and it’s rarer than it looks. It makes this bet more yours to take.

  9. Devils Advocate: Has anyone paid for the product yet?

  10. You: Yes, a few people

  11. Devils Advocate: That’s evidence, not just hope. It makes the case for you stronger.

  12. Devils Advocate:

    The real question: Is a secure path worth giving up for a chance you’d regret not taking?

  13. Devils Advocate:

    What’s genuinely strong in your case:

    • Courage is a virtue: acting well in spite of fear. Source: Aristotle, Nicomachean Ethics, Book III
    • No rulebook chooses for you. You become who you are by choosing. Source: Sartre, Existentialism Is a Humanism
  14. Devils Advocate:

    The strongest other side:

    • Source: Aristotle, Nicomachean Ethics, Book VIPractical wisdom means weighing your circumstances, not just your desire.
    • Source: Seneca, Letters to Lucilius, 18Live the worst case for a few days first, so it can’t ambush you.
    • Source: Kierkegaard, Either/Or, Part IYou’ll regret something either way, so regret alone can’t decide it.

    Paraphrases, not quotes

  15. You: But I’ll regret it forever if I don’t try.

  16. Devils Advocate: Kierkegaard would say you’ll regret something either way. Could you keep one offer open while you test for 8 weeks? Regret has a cheaper version.

  17. Devils Advocate: Here’s your hand-back card. No verdict. Your call, always.

Hand-back card

Fills in from your answers

Your position

Skip placements to build my startup full time.

What’s genuinely strong

Courage, and a story that’s yours to write.

Toughest counterpoints

  • Source: Aristotle, Nicomachean Ethics, Book VI
  • Source: Seneca, Letters to Lucilius, 18
  • Source: Kierkegaard, Either/Or, Part I

Open questions only you can answer

  • What’s your plan for month 13 if it fails?
  • What’s the least you can live on for a year?
  • Would they pay again, and tell a friend?

Cheapest test this month

Keep one offer open while you test for 8 weeks.

The sources are real; the lines are paraphrases, not quotes. The conversation is a sample.

Want it to argue with your own decision?

Join the waitlist

Devils Advocate

Challenge my idea

  1. Your idea
  2. Questions
  3. Real question
  4. Both sides
  5. Push back
  6. Hand-back

  1. Devils Advocate: Pitch me. What are you building?

  2. You: I’m building food delivery for college hostels. The big apps made it, so will I.

  3. Devils Advocate: Who pays: the students, or their parents?

  4. You: Students, from pocket money

  5. Devils Advocate: Then every order competes with the canteen and a packet of instant noodles. Small baskets, thin margins.

  6. Devils Advocate: What happens to orders during vacations?

  7. You: They dip, we’ll survive

  8. Devils Advocate: Hostels sit empty for about three months a year. That’s a quarter of the year with costs and no customers.

  9. Devils Advocate: Why won’t students just call the local dhaba?

  10. You: We’re faster

  11. Devils Advocate: Faster matters at 11 p.m., when the dhaba’s shut. At lunch it’s a two-minute walk away.

  12. Devils Advocate:

    The real question: Does demand survive three months of holidays a year?

    Bias spotted: Survivorship. You’re looking at the big apps, not the graveyard.

  13. Devils Advocate:

    What’s genuinely strong in your case:

    • A captive audience, all in one place.
    • Dense routes: one building, hundreds of customers.
    • Cheap marketing through hostel groups.
  14. Devils Advocate:

    The strongest other side:

    • Source: Hostel snack app, 2017–2019Couldn’t cover delivery costs on small orders.
    • Source: Campus grocery app, 2018–2020Saw orders collapse every vacation.
    • Source: Meal-plan app, 2016–2018Lost to the hostel’s own mess contract.

    Illustrative examples for this demo

  15. You: But we’ll be faster than the dhaba.

  16. Devils Advocate: Then prove it where speed wins: late nights, one hostel, two weeks. If people order again, you’ve got something.

  17. Devils Advocate: Here’s your hand-back card. No verdict. Your call, always.

Hand-back card

Fills in from your answers

Your position

Food delivery for college hostels.

What’s genuinely strong

A dense, captive audience that’s cheap to reach.

Toughest counterpoints

  • Source: Hostel snack app, 2017–2019
  • Source: Campus grocery app, 2018–2020
  • Source: Meal-plan app, 2016–2018

Open questions only you can answer

  • Can a small order cover the cost of delivering it?
  • Can the business cover three empty months?
  • Is late night your whole market?

Cheapest test this month

Run late-night delivery in one hostel for two weeks. Count the repeat orders.

Samples use made-up startups, labeled as illustrative. The real thing cites sources.

Want it to argue with your own idea?

Join the waitlist

The people who love you are terrible at this.

  • Your friends say follow your heart.
  • Your parents say be practical.
  • The internet says both, depending on the hour.

Nobody shows their sources.

The question keeping you up isn’t new. Quit or stay, move or not, what actually matters: philosophers have argued about it for 2,000 years, on both sides. Most of us only ever hear the side we already agree with. We bring the best of both, with book and chapter, so you decide on arguments, not vibes.

  • Your friends say it’s genius.
  • Your parents say be careful.
  • The internet says quit your job.

Nobody shows their sources.

For every delivery app on your phone, there’s a graveyard of food apps nobody remembers. That’s survivorship bias: you only hear from the ones who made it, because the ones who didn’t aren’t posting about it. We give tours of the graveyard, so you don’t have to move in.

What it does for your decisionidea

The mode you’d pick: Challenge my decision

The mode you’d pick: Challenge my idea

Devils Advocate: For the big calls and the beliefs you’ve never questioned. Skip placements? Take the offer? Move cities? We bring what the great thinkers argued on both sides, with the page number, so it’s not just vibes.

What it does, specifically

Finds the question under your question
“Should I quit?” is usually “is security worth a regret?” We name it, so you argue about the right thing.
Brings both sides
Thinkers who’d back you and thinkers who’d stop you, with book and chapter for each.
Checks every quote
Quotes are checked word for word against the text. Paraphrases are labeled as paraphrases.
Hands you a smaller first step
A way to test the decision this month, before you bet everything on it.

What you can bring

Big life decisions
Quit, stay, move, or marry the startup.
Philosophy and beliefs
Argue with Aristotle. He’s had time to prepare.

Devils Advocate: For the startup, side project, or work proposal you’re about to bet time and money on. We find who tried it before, how it ended, and what would have to be true for you to be different.

What it does, specifically

Names the bias
You’re looking at the winners. We show you the graveyard, and call out survivorship bias when it’s doing the thinking.
Finds who tried it before
Startups that went after the same customers, how they ended, and why. Every one sourced.
Asks the unglamorous questions
Who pays, what it costs to serve them, and what happens in the off-season.
Hands you the cheapest test
Something you can run this month, before you spend real money.

What you can bring

Startup ideas
Before you pitch it, bury it (on paper).
Work proposals
Stress-test the strategy before your boss does.

Here’s exactly what will happen when you show up

Keep scrolling. It plays out one step at a time.

Skip to the hand-back card

  1. Step 1: Pick your fight.

    Choose Challenge my decision. That’s it.

    Devils Advocate

    Challenge my decision(chosen)
    Challenge my idea

  2. Step 2: Spill it.

    Type out the decision like you’d text a friend at 2 a.m. Long rants welcome. Typos forgiven.

    Devils Advocate

    Challenge my decision

    Type it like you’d text a friend.

    I’m skipping placements to build my startup full time.

  3. Step 3: We ask before we argue.

    Up to three questions about what’s at stake for you, so we argue with what you actually mean, not what we assumed.

    Devils Advocate

    Challenge my decision

    You: I’m skipping placements to build my startup full time.

    Devils Advocate: What would you lose if it fails in 12 months?

    Devils Advocate: Does anyone depend on your income?

    Devils Advocate: Has anyone paid for the product yet?

  4. Step 4: We name the real question.

    Under “should I quit?” there’s usually something bigger, like “is security worth a regret?”

    Devils Advocate

    Challenge my decision

    You: I’m skipping placements to build my startup full time.

    Devils Advocate:

    The real question: is a secure path worth giving up for a chance you’d regret not taking?

  5. Step 5: Receipts, both sides.

    First, what’s genuinely strong in your case. Then the strongest other side: what great thinkers argued, with book and chapter. No made-up quotes. We check.

    Devils Advocate

    Challenge my decision

    The case for you

    Devils Advocate: Many traditions prize courage and writing your own story.

    The other side

    Devils Advocate:
    • Source: Aristotle, Nicomachean Ethics, Book VI

      Practical wisdom means weighing your circumstances, not just your desire.

    • Source: Seneca, Letters to Lucilius

      Rehearse the worst case before you act, so it can’t ambush you.

    Paraphrases, not quotes

  6. Step 6: Push back.

    Disagree with us? Good. Every round brings fresh evidence, never the same point twice.

    Devils Advocate

    Challenge my decision

    You: But I’ll regret it forever if I don’t try.

    Devils Advocate: Maybe. Could you keep one offer open while you test for 8 weeks? Regret has a cheaper version.

  7. Step 7: You decide.

    You leave with a hand-back card and zero verdicts. Your life, your call.

    Devils Advocate

    Challenge my decision

    Hand-back card

    Your position

    I’m skipping placements to build my startup full time.

    Toughest counterpoints

    • Source: Aristotle, Nicomachean Ethics, Book VI
    • Source: Seneca, Letters to Lucilius

    Cheapest test this month

    Keep one offer open while you test for 8 weeks.

    Your call. Always.

Step 1 of 7

Pick your fight.

Choose Challenge my decision. That’s it.

Step 2 of 7

Spill it.

Type out the decision like you’d text a friend at 2 a.m. Long rants welcome. Typos forgiven.

Step 3 of 7

We ask before we argue.

Up to three questions about what’s at stake for you, so we argue with what you actually mean, not what we assumed.

Step 4 of 7

We name the real question.

Under “should I quit?” there’s usually something bigger, like “is security worth a regret?”

Step 5 of 7

Receipts, both sides.

First, what’s genuinely strong in your case. Then the strongest other side: what great thinkers argued, with book and chapter. No made-up quotes. We check.

Step 6 of 7

Push back.

Disagree with us? Good. Every round brings fresh evidence, never the same point twice.

Step 7 of 7

You decide.

You leave with a hand-back card and zero verdicts. Your life, your call.

Devils Advocate

Challenge my decision

Challenge my decision(chosen)
Challenge my idea

Type it like you’d text a friend.

I’m skipping placements to build my startup full time.

You: I’m skipping placements to build my startup full time.

Devils Advocate: What would you lose if it fails in 12 months?

Devils Advocate: Does anyone depend on your income?

Devils Advocate: Has anyone paid for the product yet?

You: I’m skipping placements to build my startup full time.

Devils Advocate:

The real question: is a secure path worth giving up for a chance you’d regret not taking?

The case for you

Devils Advocate: Many traditions prize courage and writing your own story.

The other side

Devils Advocate:
  • Source: Aristotle, Nicomachean Ethics, Book VI

    Practical wisdom means weighing your circumstances, not just your desire.

  • Source: Seneca, Letters to Lucilius

    Rehearse the worst case before you act, so it can’t ambush you.

Paraphrases, not quotes

You: But I’ll regret it forever if I don’t try.

Devils Advocate: Maybe. Could you keep one offer open while you test for 8 weeks? Regret has a cheaper version.

Hand-back card

Your position

I’m skipping placements to build my startup full time.

Toughest counterpoints

  • Source: Aristotle, Nicomachean Ethics, Book VI
  • Source: Seneca, Letters to Lucilius

Cheapest test this month

Keep one offer open while you test for 8 weeks.

Your call. Always.

  1. Step 1: Pick your fight.

    Choose Challenge my idea. That’s it.

    Devils Advocate

    Challenge my decision
    Challenge my idea(chosen)

  2. Step 2: Spill it.

    Type out your idea like you’d pitch it to a friend. Long rants welcome. Typos forgiven.

    Devils Advocate

    Challenge my idea

    Type it like you’d text a friend.

    Food delivery for college hostels. The big apps did it, so there’s clearly demand.

  3. Step 3: We ask before we argue.

    Up to three questions: who pays, what it costs, what happens when it goes quiet. So we argue with your actual plan.

    Devils Advocate

    Challenge my idea

    You: Food delivery for college hostels. The big apps did it, so there’s clearly demand.

    Devils Advocate: Who pays, students or parents?

    Devils Advocate: What happens to orders during vacations?

    Devils Advocate: Why won’t hostels just call the local dhaba?

  4. Step 4: We name the real question.

    Often it’s a sneaky bias, like survivorship: you’re looking at the winners, not the graveyard.

    Devils Advocate

    Challenge my idea

    You: Food delivery for college hostels. The big apps did it, so there’s clearly demand.

    Devils Advocate:

    The real question: does demand survive 3 months of holidays a year?

    Bias spotted: survivorship. You’re looking at the big apps, not the graveyard.

  5. Step 5: Receipts, both sides.

    First, what’s genuinely strong in your idea. Then the strongest other side: startups that tried something similar, how they ended, every claim sourced.

    Devils Advocate

    Challenge my idea

    The case for you

    Devils Advocate: Captive audience, dense delivery routes, cheap marketing through hostel groups.

    The other side

    Devils Advocate:
    • Source: Hostel snack app, 2017–2019

      Couldn’t cover delivery costs on small orders.

    • Source: Campus grocery app, 2018–2020

      Saw orders collapse every vacation.

    • Source: Meal-plan app, 2016–2018

      Lost to the hostel’s own mess contract.

    Illustrative examples for this demo

  6. Step 6: Push back.

    Disagree with us? Good. Every round brings fresh evidence, never the same point twice.

    Devils Advocate

    Challenge my idea

    You: But we’ll do breakfast subscriptions!

    Devils Advocate: Interesting. Subscriptions fix vacation dips only if parents prepay a semester. Would they?

  7. Step 7: You decide.

    You leave with a hand-back card, the cheapest test you can run this month, and zero verdicts. Your idea, your call.

    Devils Advocate

    Challenge my idea

    Hand-back card

    Your position

    Food delivery for college hostels. The big apps did it, so there’s clearly demand.

    Toughest counterpoints

    • Source: Hostel snack app, 2017–2019
    • Source: Campus grocery app, 2018–2020
    • Source: Meal-plan app, 2016–2018

    Cheapest test this month

    Ask hostel parents if they’d prepay a semester of breakfasts.

    Your call. Always.

Step 1 of 7

Pick your fight.

Choose Challenge my idea. That’s it.

Step 2 of 7

Spill it.

Type out your idea like you’d pitch it to a friend. Long rants welcome. Typos forgiven.

Step 3 of 7

We ask before we argue.

Up to three questions: who pays, what it costs, what happens when it goes quiet. So we argue with your actual plan.

Step 4 of 7

We name the real question.

Often it’s a sneaky bias, like survivorship: you’re looking at the winners, not the graveyard.

Step 5 of 7

Receipts, both sides.

First, what’s genuinely strong in your idea. Then the strongest other side: startups that tried something similar, how they ended, every claim sourced.

Step 6 of 7

Push back.

Disagree with us? Good. Every round brings fresh evidence, never the same point twice.

Step 7 of 7

You decide.

You leave with a hand-back card, the cheapest test you can run this month, and zero verdicts. Your idea, your call.

Devils Advocate

Challenge my idea

Challenge my decision
Challenge my idea(chosen)

Type it like you’d text a friend.

Food delivery for college hostels. The big apps did it, so there’s clearly demand.

You: Food delivery for college hostels. The big apps did it, so there’s clearly demand.

Devils Advocate: Who pays, students or parents?

Devils Advocate: What happens to orders during vacations?

Devils Advocate: Why won’t hostels just call the local dhaba?

You: Food delivery for college hostels. The big apps did it, so there’s clearly demand.

Devils Advocate:

The real question: does demand survive 3 months of holidays a year?

Bias spotted: survivorship. You’re looking at the big apps, not the graveyard.

The case for you

Devils Advocate: Captive audience, dense delivery routes, cheap marketing through hostel groups.

The other side

Devils Advocate:
  • Source: Hostel snack app, 2017–2019

    Couldn’t cover delivery costs on small orders.

  • Source: Campus grocery app, 2018–2020

    Saw orders collapse every vacation.

  • Source: Meal-plan app, 2016–2018

    Lost to the hostel’s own mess contract.

Illustrative examples for this demo

You: But we’ll do breakfast subscriptions!

Devils Advocate: Interesting. Subscriptions fix vacation dips only if parents prepay a semester. Would they?

Hand-back card

Your position

Food delivery for college hostels. The big apps did it, so there’s clearly demand.

Toughest counterpoints

  • Source: Hostel snack app, 2017–2019
  • Source: Campus grocery app, 2018–2020
  • Source: Meal-plan app, 2016–2018

Cheapest test this month

Ask hostel parents if they’d prepay a semester of breakfasts.

Your call. Always.

The hand-back card

Every session ends with one card that’s yours to keep:

  • Your position, in one line
  • The 3 toughest counterpoints, each with its source
  • What’s genuinely strong in your case
  • The open questions only you can answer
  • The cheapest test you can run this month

No verdict. We don’t do verdicts. We do homework.

Hand-back card

Challenge my decision

Your position

I’m skipping placements to build my startup full time.

Toughest counterpoints

  1. Practical wisdom means weighing your circumstances, not just your desire.

    Source: Aristotle, Nicomachean Ethics, Book VI

  2. Live the worst case for a few days first, so it can’t ambush you.

    Source: Seneca, Letters to Lucilius, 18

  3. You’ll regret something either way, so regret alone can’t decide it.

    Source: Kierkegaard, Either/Or, Part I

Paraphrases, not quotes

What’s genuinely strong

Courage, and a story that’s yours to write.

Open questions only you can answer

  • What would you lose if it fails in 12 months?
  • Does anyone depend on your income?
  • What would make you stop?

Cheapest test this month

Keep one offer open while you test for 8 weeks.

Devils AdvocateYour call. Always.

Hand-back card

Challenge my idea

Your position

Food delivery for college hostels. The big apps did it, so there’s clearly demand.

Toughest counterpoints

  1. Couldn’t cover delivery costs on small orders.

    Source: Hostel snack app, 2017–2019

  2. Saw orders collapse every vacation.

    Source: Campus grocery app, 2018–2020

  3. Lost to the hostel’s own mess contract.

    Source: Meal-plan app, 2016–2018

Illustrative examples for this demo

What’s genuinely strong

Captive audience, dense delivery routes, cheap marketing through hostel groups.

Open questions only you can answer

  • Does demand survive 3 months of holidays a year?
  • Would parents prepay a semester?
  • Why won’t hostels just call the local dhaba?

Cheapest test this month

Ask hostel parents if they’d prepay a semester of breakfasts.

Devils AdvocateYour call. Always.

Pricing (yes, we argued about this too)

Devils Advocate: Cheaper than one bad decision. Prices apply from launch on .

Yearly

$150 per year

That’s $12.50 a month. You save $558 a year (79%) compared with paying monthly.

For people who make decisions for a living. Or just a lot of them.

Join the waitlist
  • Both modes: Challenge my idea and Challenge my decision
  • All four areas: startup ideas, big life decisions, work proposals, and philosophy and beliefs
  • Unlimited debates (fair use)
  • Up to 3 clarifying questions before every debate, so we argue with what you actually mean
  • The case for you first, then the strongest other side
  • Receipts on every counterpoint: real failed startups and real philosophers, every quote checked
  • Push back as many rounds as you like, with fresh evidence each time
  • A hand-back card after every session: your position, the toughest counterpoints, open questions, and the cheapest test to run
  • Saved history, so the next session picks up where the last one ended
  • Your sessions stay private; delete them anytime

Monthly

$59 per month

For when you’ve got a big call coming up.

Join the waitlist
  • Both modes: Challenge my idea and Challenge my decision
  • All four areas: startup ideas, big life decisions, work proposals, and philosophy and beliefs
  • Unlimited debates (fair use)
  • Up to 3 clarifying questions before every debate, so we argue with what you actually mean
  • The case for you first, then the strongest other side
  • Receipts on every counterpoint: real failed startups and real philosophers, every quote checked
  • Push back as many rounds as you like, with fresh evidence each time
  • A hand-back card after every session: your position, the toughest counterpoints, open questions, and the cheapest test to run
  • Saved history, so the next session picks up where the last one ended
  • Your sessions stay private; delete them anytime

Payments are processed securely by our payment partner.

Joining the waitlist is free and commits you to nothing. We’ll email you before billing starts.

Fair use: unlimited means normal human use, not a bot arguing with our bot.

Things we refuse to do

FAQ

Isn’t this just another AI chatbot with an attitude?

Most chatbots are trained to be agreeable. We’re built to find the other side, and we bring receipts: a curated database of failed startups and the actual texts of philosophers, with every quote checked.

Does it just disagree with everything?

No. It tells you what’s strong first, then the strongest other side. Then it steps aside.

What if I’m actually right?

Then you walk away more sure, with the counterarguments already handled. That’s a win.

Can I talk to it instead of typing?

Not at launch. It’s text-only for now. Your thumbs will survive.

Who is it for?

MBA students, first-time founders, and anyone about to make a call they’d hate to get wrong.

Can I use it right now?

Not yet. Private beta opens , and the waitlist gets in first.

How much will it cost?

$59 a month, or $150 a year if you like saving $558. Prices apply from .

How do I pay?

Payments are processed securely by our payment partner.

What do you do with my waitlist details?

We use them only to invite you to the beta. Email avinashdev.garudapalli2027@mastersunion.org and we’ll delete them.

Got an idea you’re completely sure about? Perfect.

Join the waitlist. We’ll argue with you on December 1.

I am a (pick one)
What would you bring first? (pick any)
Privacy

Devils Advocate: You’re in. Welcome to the argument.

Devils Advocate: We’ll email you before the beta opens on December 1. The waitlist gets in first, so you’ll be one of the first people we politely disagree with.

Your first hand-back card

Your position

I’m on the waitlist.

Toughest counterpoint

None. It’s the one call we won’t argue with.

Cheapest test before December 1

Doubt one thing you believed this morning.

Your call. Always.