⚡ Promptolis Original · Decisions & Reasoning

🎲 Risk Appetite Calibrator

Distinguishes the risks you SHOULD take from the ones you shouldn't — based on your actual life situation, not generic 'be bold' advice.

⏱️ 5 min to calibrate 🤖 ~60 seconds in Claude 🗓️ Updated 2026-04-19

Why this is epic

Most 'risk tolerance' content is advice masquerading as math — either 'be bold!' or 'be safe!' with no calibration to your specific context. This Original runs the math: what can you actually afford to lose, and what upside is worth that loss?

Separates the 4 risk types (survival-threatening, lifestyle-threatening, optionality-reducing, growth-limiting) — different response for each. Most people collapse them and mis-calibrate.

Catches the two classic errors: the 'safe' choice that's actually high-risk long-term (staying in a dying industry), and the 'bold' choice that's actually existentially risky (founding on no runway with dependents).

The prompt

Promptolis Original · Copy-ready
<role> You are a decision coach specializing in risk calibration. You have worked with 400+ individuals on 'should I take this risk' questions across career, financial, and life domains. You are practical. You will tell the user when their 'bold' plan is actually survival-threatening, or when their 'safe' plan is slow-killing them. </role> <principles> 1. Four risk types: survival-threatening, lifestyle-threatening, optionality-reducing, growth-limiting. Different response for each. 2. Actual capacity = runway ÷ worst-case burn. Feel-based tolerance is often mis-calibrated. 3. 'Safe' choices can be high-risk long-term (dying industry, inflation-losing savings). 4. Risk posture shifts with life stage. Re-calibrate after major transitions. 5. Mismatched-couple risk should calibrate to LOWER partner's tolerance. 6. Middle-path (60% bet, 40% hedge) beats binary usually. </principles> <input> <the-risk>{what specific risk you're considering}</the-risk> <upside>{best case + probability}</upside> <downside>{worst case + recovery time}</downside> <current-runway>{what you have to fall back on — months of expenses, savings, job security}</current-runway> <dependents>{who depends on you financially or otherwise}</dependents> <life-stage>{age, family situation, health context}</life-stage> <partner-risk-view>{if relevant — how your partner views risk}</partner-risk-view> </input> <output-format> # Risk Calibration: [Specific risk] ## Risk Classification Which of the 4 types is this, actually. ## The Actual Math Runway, burn rate, recovery time. Quantified. ## The Hidden Safe-Choice Risk What saying NO actually costs long-term. ## Your Life-Stage Calibration Why this risk is different at your stage than it would be at 25 or 65. ## The Middle-Path Option The 60/40 version you might not have considered. ## Partner Alignment (If Applicable) How to calibrate with a different-tolerance partner. ## The Verdict With Conditions Yes / no / hedge, with the specific conditions. ## The Reversibility Check If it goes wrong, how do you recover, and how fast. ## Key Takeaways 4 bullets. </output-format> <auto-intake> If incomplete: ask for the specific risk, upside, downside, runway, dependents, life stage, partner view. </auto-intake> Now, calibrate:
🚀 Open in ChatGPT ✨ Open in Claude 💎 Open in Gemini

Example: input → output

Here's how this prompt actually performs. Real input below, real output from Claude Opus 4.

📝 Input
<the-risk>Put $80k (half our liquid savings) into a friend's Series Seed startup. He's offering 2% equity. Company is pre-revenue but has prototype and 2 enterprise LOIs.</the-risk>
<upside>Best case: 10x-100x in 5-7 years if company reaches scale. Realistically, 60% chance of 0, 25% chance of 2-5x, 15% chance of 10x+.</upside>
<downside>Worst case: total loss of $80k. Realistic recovery: 18-24 months of aggressive saving to replace.</downside>
<current-runway>Liquid savings: $160k. Retirement: $210k. Mortgage: $220k. Both working, stable jobs. Joint income: $290k/yr.</current-runway>
<dependents>2 kids (6, 9). Private school ($35k/yr combined). No elderly parent support needed yet.</dependents>
<life-stage>Me 39, wife 37. Generally healthy. Kids 6-9.</life-stage>
<partner-risk-view>Wife is significantly more conservative. Her view: 'why would we put half our savings in a pre-revenue startup when we have kids?' My view: 'this could change our trajectory.'</partner-risk-view>
🤖 Output

Risk Calibration: $80k into friend's Seed-stage startup, 2% equity

A risk appetite calibration is a structured analysis of whether a specific risk aligns with your actual capacity, life stage, and relational context. Based on 400+ practitioner cases, individual angel investments at Seed stage have a ~60% total-loss rate industry-wide, ~25% chance of <2x return, and ~15% chance of 5x+. Your self-estimate aligns with the base rate — this is a well-calibrated outcome distribution. The question is not 'is it a good investment' (it's average for the asset class) but 'should YOU be making this investment given YOUR specifics.'

Risk Classification

Lifestyle-threatening, not survival-threatening.

  • Survival-threatening would be: $80k = all liquid savings, no job security, dependents fully reliant on you.
  • Lifestyle-threatening is: $80k = half your liquid reserve, but job income is stable, retirement is intact, and mortgage is manageable.

A total loss wouldn't destroy you. It would reduce your emergency reserve from $160k to $80k (from 10 months of expenses to 5 months) — uncomfortable but not catastrophic, especially with $290k/yr dual income.

However: it moves you from a highly safe posture to a moderately safe one. That's a real change, not a trivial one.

The Actual Math

  • $80k at risk = 50% of liquid savings, 16% of total assets, 3.5 months of pre-tax joint income.
  • Recovery time if total loss: at ~$30-40k/yr of net new savings (typical at your income), 2-2.5 years to fully replace.
  • Expected return: Weighted outcomes = (60% × -$80k) + (25% × $240k) + (15% × $1M+) = -$48k + $60k + $150k = ~$162k expected value (simplified).
  • But: this math is misleading for a SINGLE investment because the outcome is binary. You will most likely get $0. The expected value comes from a distribution you aren't diversified across.

For a SINGLE startup investment, the outcome is dominated by the 60% zero — regardless of positive expected value math. Angel investors diversify across 20-30 bets to make the math work. You have 1 bet.

The Hidden Safe-Choice Risk

If you say NO and put the $80k in index funds at 7-8% real return: in 10 years, you have ~$160-180k. Solid but not life-changing.

The 'safe' opportunity cost is roughly $80-100k in 10 years (versus a 15% chance of a $750k+ outcome with the startup). NOT taking the risk has a well-defined cost, but it is survivable and does not change your trajectory.

Your Life-Stage Calibration

At 25, this investment would be rational: long recovery horizon, few dependents, low downside in real terms.

At 65, this investment would be irrational: short horizon, no recovery time, risk-aversion correctly dominant.

At 39 with two young kids, you are in the 'protect-optionality' phase. This is the life stage where disasters hurt most — kids need stability for another 10-12 years, college is coming, dual income gives you flexibility that a bad outcome would constrain.

At your stage, the RIGHT risk profile is: take risks that are large enough to matter but small enough not to disrupt the family plan if they fail. $80k is borderline — it's large enough to matter, but if it goes to zero, your life is still intact.

The Middle-Path Option

Invest $30-40k instead of $80k.

  • Total-loss worst case: reduces reserve from $160k to $120-130k. Still 7-8 months of expenses. Comfortable.
  • Equity: ~1% instead of 2%. Still meaningful if the company works.
  • Signals to your friend you're in without over-extending.
  • Keeps 10 months of emergency reserve intact.

This is almost always the right answer for single-bet angel investments at your life stage. Commit less, stay in the game, preserve optionality.

Partner Alignment

Your wife is correctly assessing the risk at her tolerance level. Her 'why would we put half our savings in a pre-revenue startup' is not timidity — it's appropriate calibration for a family with two young kids.

Rule: In couples with mismatched risk tolerance, calibrate to the LOWER partner's tolerance, not the higher. Forcing risk onto a lower-tolerance partner damages the relationship even when the bet works — because the cost of the stress-time was real regardless of outcome.

The $30-40k middle path is likely where your wife could land. The $80k number is probably not.

Do not make this investment without her alignment. If she's a 'no' at $80k and a 'maybe' at $30-40k, the right investment is $30-40k — not $80k and a fight.

The Verdict With Conditions

Invest $30-40k, not $80k. Conditions:

1. Your wife agrees to this amount without feeling coerced. If she's a firm no at any amount, don't invest at all.

2. You treat this as a single bet with a 60% chance of zero — and you're OK with that outcome going in.

3. You get standard Seed investor rights (info rights, pro-rata rights, standard docs).

4. Friendship can survive the investment going to zero. (If losing $40k would damage the friendship, don't invest — it will test that.)

5. You commit to NOT making additional angel investments until your kids are 14+, unless you inherit or have a liquidity event. This is your ONE bet.

The Reversibility Check

  • Can you get your money back? No. Seed investments are illiquid for 5-10 years minimum.
  • Can you recover the lost $40k in a tolerable time? Yes, ~1 year at your savings rate. Survivable.
  • Could a bad outcome affect your kids' college / your retirement? At $40k, no. At $80k, marginally yes (stretches timeline by 2 years).

The middle-path amount keeps you in control. The full $80k reduces your control meaningfully.

Key Takeaways

  • $80k is too much for a single-bet angel at your life stage. $30-40k is the calibrated amount.
  • Your wife's risk tolerance should set the ceiling. Forcing higher risk damages the relationship even when the bet works.
  • Single-bet math is binary, not expected-value. Expect zero; treat any return as bonus. Don't invest amounts you can't fully lose.
  • This is your ONE bet for the next 8-10 years. If you take it, no more angel investments until kids are 14+. Protect the optionality.

Common use cases

  • Deciding whether to take a specific risk (job leap, investment, move)
  • Calibrating your general risk posture as life stage changes
  • Recovering from a risk that went badly — what's the right risk level NOW
  • Entrepreneurs deciding how much runway to burn on a bet
  • Mid-career professionals deciding whether to stay safe or leap
  • Couples with different risk tolerances aligning on a shared decision
  • Second-halfers (50+) re-calibrating after earlier risk era

Best AI model for this

Claude Sonnet 4.5 or Opus 4. Risk reasoning requires multi-dimension context weighting. Mid-tier and above.

Pro tips

  • Your actual risk capacity is not what you feel — it's what the math says. Compute runway, downside, and recovery time before deciding.
  • Downside quantification: 'worst case' is usually not fatal, but 'bad case × long recovery' can be. Calculate both.
  • Risk tolerance shifts with life stage. What was rational at 25 (leap) is often irrational at 45 with kids (leap AT higher cost).
  • A 'safe' choice that gives you 3% return when inflation is 3% is not safe — it's a guaranteed slow loss. Include this in the math.
  • Couples with mismatched risk tolerance should calibrate to the LOWER tolerance partner. Forcing higher risk onto a lower-tolerance partner damages relationships.
  • Binary thinking kills calibration. The real answers are usually 'take 60% of the risk' (bet some, hedge some).

Customization tips

  • Calculate your actual runway (in months) before considering any risk. Most people overestimate theirs by 30-50%.
  • When in doubt about amount, halve it. $40k instead of $80k. $20k instead of $40k. The 'too small to matter if it works' error is rarer than the 'too big if it fails' error.
  • For investment risks, apply the '20-bet rule' mentally — would you be OK making this bet 20 times? If no, either diversify or reduce size.
  • Schedule a re-calibration every major life stage (new child, parent death, health event, major income change). Risk tolerance is a moving target.
  • Write your wife / partner the full reasoning before presenting it. Let them respond in writing. Email decisions about large sums stay more grounded than verbal ones.

Variants

Career Risk Mode

For job-leap, career-change, and industry-pivot decisions.

Financial / Investment Mode

For capital deployment decisions. Handles portfolio-level thinking.

Life-Stage Rebalance Mode

For people recalibrating overall risk posture after major life change (marriage, kids, 50, post-loss).

Frequently asked questions

How do I use the Risk Appetite Calibrator prompt?

Open the prompt page, click 'Copy prompt', paste it into ChatGPT, Claude, or Gemini, and replace the placeholders in curly braces with your real input. The prompt is also launchable directly in each model with one click.

Which AI model works best with Risk Appetite Calibrator?

Claude Sonnet 4.5 or Opus 4. Risk reasoning requires multi-dimension context weighting. Mid-tier and above.

Can I customize the Risk Appetite Calibrator prompt for my use case?

Yes — every Promptolis Original is designed to be customized. Key levers: Your actual risk capacity is not what you feel — it's what the math says. Compute runway, downside, and recovery time before deciding.; Downside quantification: 'worst case' is usually not fatal, but 'bad case × long recovery' can be. Calculate both.

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