Building Wealth
Founder Fiona
Co-Founder & CTO · Austin, TX
$500k in startup equity. Zero liquidity. One big question: when does this become real money?
About Founder Fiona
Fiona's cap table says she is worth $500k. Her bank account says she has $28k in emergency savings and an $80k salary that has not kept up with Austin rent. She cannot sell a single share, borrow against illiquid equity, or pay her dentist in stock options — and her co-founder is pushing for a Series B that would dilute her further. She is rich on a spreadsheet and cash-poor in every way that matters, and the exit that would change everything keeps being two years away.
Financial Snapshot
$80,000 (salary) + equity
Annual Income
$500,000 (mostly illiquid)
Net Worth
38
Age
Founder Fiona's Story — 6 Episodes
The Founder's Decision
After months of modeling, Fiona makes her call: she negotiates the $130k salary, keeps her existing equity, and sets a personal deadline — if no exit by age 40, she transitions to a VP role at a larger company and treats the equity as a lottery ticket.
Uses: fireThe Salary Negotiation
Fiona's co-founder proposes raising her salary to $130k as part of the Series B. She models the trade-off: higher salary now vs. larger equity refresh at the lower salary. The tax implications are significant.
Uses: salary-jumpThe Personal Runway
Fiona's $28k emergency fund covers 5.4 months. The Series B process takes 6-9 months. She models what happens if the raise falls through and she has to find a salaried job — or worse, the company runs out of cash during fundraising.
Uses: emergency-fundThe Dilution Trap
The Series B would raise $8M at a $30M pre-money valuation. Fiona's 12% stake gets diluted to 9.2%. She models whether the higher valuation compensates for the smaller slice — and discovers the answer depends entirely on the exit multiple.
Uses: windfallThe QSBS Question
Fiona learns that her shares may qualify for the Section 1202 QSBS exclusion — potentially $10M in federal capital gains tax-free. But the rules are strict and she may have already missed a window.
Uses: roth-vs-traditionalThe Exit Math
Fiona models three exit scenarios: Series B at $30M valuation, acquisition at $15M, and acquisition at $50M. After QSBS exemption, dilution, and taxes, the after-tax proceeds are very different from the headline numbers.
Uses: windfall