From Series A liquidity to lasting security: transforming shares into a diversified plan

How a Series A founder turned secondary share liquidity into lasting security by diversifying beyond his startup and locking in long-term tax advantages.

Scene 0 - Trading dilution risk for personal stability

Meet Rohan M., 36, based in Palo Alto. Married, one toddler at home. After raising a $25M Series A for his enterprise SaaS startup, Rohan finally took a modest salary and sold a small block of his founder equity. For the first time, there was real liquidity on the table.

But then came the challenge of deploying the cash and optimizing the tax bill that came with it.

Scene 1 - The liquidity map

We started by mapping the flow of new cash. $500K came in from secondary shares; $120K annual salary kept household expenses covered. Rather than leave the part cash in a low-yield account, Alphanso built a ladder of muni bonds and short-term treasuries. Result: liquidity preserved for burn and family costs, while earning a safe yield instead of sitting idle. The rest of it was invested in a diversified growth portfolio.

Scene 2 - Roth moves into a sweet spot

Despite raising millions for the company, Rohan’s personal taxable income was still moderate. We used that window to:

Convert a chunk of his traditional 401(k) into Roth while staying within a lower bracket.
Open a self-directed Roth IRA, seeding it with after-tax contributions and earmarking it for future startup and VC feeder fund deals.

What looked like a “low-salary” year became the ideal time to lock in decades of tax-free growth.

Scene 3 - Tax optimization

Rohan’s biggest blind spot: understanding his tax liabilities and minimizing them effectively.

Filed the 83(b) election, ensuring he pays only capital gains tax.
Optimized liquidity so that income gains didn’t push him into a higher tax bracket (kept at 15% instead of 20%).
Offset capital gains through strategic tax-loss harvesting.

Scene 4 - Reducing dependence on the “one exit”

We modeled different outcomes: IPO, acquisition, down-round. Each scenario showed how dependent Rohan’s family was on a single event. By layering in institutional funds, muni bonds, and dividend income, his probability of hitting core family goals (college, retirement, a second home in Tahoe) rose from 58% to 84%, even without a blockbuster exit.

Where Rohan ended up

Liquidity secured: Idle cash moved into safe yield instruments, extending personal runway.
Lifetime tax edge: 401(k) → Roth conversions plus a self-directed Roth built a foundation for tax-free private investing.
Taxes Optimized: Tax bill reduced by $50,000.

Behind the scenes (our toolkit)

Liquidity mapping & muni ladder • Roth conversion modeling • Self-directed Roth IRA setup • VC/PE feeder fund access • Portfolio diversification strategy • Goal-probability Monte Carlo

💡 This case study is based on a real client story. Names and some details have been changed to protect privacy.