Predict Target Responses

Training target CEO mind... (~10 min)

Based on Sarah's strategic priorities and situation:
Valuation Assessment:
Will Sarah accept $300M? MAYBE, with concerns
Her valuation thinking:
- Sarah believes company is worth $400-450M
- Sees similar companies exit at 10-12x ARR
- 60% growth rate justifies premium multiple
- But: burn rate creates urgency ($12M runway = 12 months)
What she's thinking:
"8x is below market for our growth rate. But we need
capital in 12 months. If I wait for Series C, dilution
+ time risk might be worse than selling at slight discount."
Acceptable range: $350-400M
Walk-away: $300M (only if desperate)
Target: $400M+
Deal Structure Analysis:
Cash vs Stock Concern:
- Sarah NEEDS $150M+ cash personally
- She owns 40% = $120M at $300M valuation
- $200M total cash = $80M to her (after taxes: ~$50M)
- THIS IS NOT ENOUGH for her goals
Her thought: "I need $100M+ after-tax to be set for life.
$50M isn't enough after building this for 8 years."
Stock Vesting Concern:
- 2-year vest = more risk and golden handcuffs
- Worried about your stock value
- Prefers cash or shorter vest (6-12 months)
Her thought: "I don't want to be locked in for 2 years
with stock that might decline. I've taken enough risk."
Role Concern:
- 18-month GM role feels like "managed exit"
- Either wants real CEO role (3+ years) or clean exit
- Doesn't want to be "window dressing"
Her thought: "18 months means you're planning to replace
me. I'd rather exit clean with cash than be pushed out."
Her Real Priorities:
Priority 1: Personal Cash ($100M+ after-tax)
- She's 45, this is her one exit opportunity
- Needs enough to never work again
- $50M after-tax is not enough
Priority 2: Team Retention
- Feels responsible for 150 employees
- Needs strong retention packages
- Will negotiate for team, not just herself
Priority 3: Product Vision
- Wants product to succeed long-term
- Concerned about integration killing innovation
- Needs commitment to product investment
If you offer $300M ($200M cash + $100M stock):
- 40% chance Sarah accepts (only if desperate)
- 60% chance she rejects or counters at $375M+
- Will push for more cash, less stock
Optimal Offer to Close Sarah:
Option A: Higher Valuation, Same Structure
- $375M ($250M cash + $125M stock)
- Sarah gets $100M cash (40% ownership)
- After tax: ~$65M (closer to her goal)
- 70% chance she accepts
Option B: Same Valuation, Better Structure
- $300M ($250M cash + $50M stock)
- More cash upfront = more personal liquidity
- Shorter 1-year vest on stock
- 75% chance she accepts
Option C: Address Her Real Needs
- $350M ($275M cash + $75M stock)
- Allocate $25M for team retention (she'll love this)
- Either: Real 3-year CEO role OR clean exit with transition
- 6-month stock vest, not 2 years
- 85% chance she accepts
What Will Make Sarah Say Yes:
✓ Get her to $80M+ personal cash (after-tax: $50M+)
✓ Show commitment to team retention ($20-25M)
✓ Give her real role or clean exit (not fake 18-month GM)
✓ Reduce stock risk (shorter vest or less stock)
✓ Commit to product investment post-close
What Will Make Sarah Say No:
✗ Low cash to her personally ($50M or less after-tax)
✗ Too much stock risk (2-year vest, high stock %)
✗ Fake short-term role (18-month "GM" = exit plan)
✗ No team retention plan
✗ Integration plan that kills product
Timeline Consideration:
Sarah's urgency level: MODERATE-HIGH
- 12 months cash runway
- Series C would be challenging market
- But not desperate (could raise bridge round)
- Has 6-8 months to decide
Bottom Line:
$300M at 2/3 cash is below her target. She'll negotiate.
Optimal: $350M+ with more cash, shorter vest, team retention.
She wants to feel respected, not desperate.