How a Google alum turned a lean founder year into a $100K tax win.

How Arjun left his cushy Google job, managed a lean first year, and turned it into a $100K lifetime tax advantage with smart planning and portfolio moves.

Scene 0 - Trading a cushy Google paycheck for startup life

Meet Arjun S., 34, married, and living in the Bay Area. After nearly a decade at Google, he built a $2.8M portfolio of stock, ETFs, and cash. When he left to start a developer tools company, his steady paycheck vanished, and his investments became the runway.

Arjun kept the resignation letter open on his MacBook for three days before he finally hit “Send.” In the Googleplex cafeteria, between a pesto panini and his last refill of cold brew, he told his manager he was leaving to build something of his own.

The excitement was real. So was the math. A founder’s first year looks different, lower income, new health plan decisions, and a portfolio that suddenly has to double as a safety net.

Scene 1 - Mapping the runway on the whiteboard

At his apartment in Mountain View, Arjun and his spouse sketched their runway of living expenses, a portion covered by cash and a small bridge from vested GOOG shares. The surprise was taxes. With income down, the couple had a rare window: use the low-income year to make smart moves that could pay off for decades.

Scene 2 - 401(k) over SEP: flexibility matters

Arjun assumed “founder = SEP IRA,” but we walked through a solo-401(k) instead: better contribution flexibility and room for a future mega-backdoor Roth when cash flow improved. We tuned withholdings and estimated quarterly taxes so he wasn’t over-withholding out of habit. The impact was immediate, withholding dropped ~20%, putting real dollars back into runway without underpaying.

Scene 3 - PPO vs HSA: don’t let premiums eat the plan

Open enrollment hit right after he left. We modeled expected care costs and compared an HSA-eligible HDHP against a PPO. The HSA won by a nose given their low utilization, and we right-sized an FSA for incidental needs. No heroics, just numbers, and the confidence to pick once and move on.

Scene 4 - The Roth window

With ordinary income temporarily low, we developed a strategy to partially convert assets from prior 401(k) and IRA accounts into Roth accounts. The objective was to keep taxable income within the 22% bracket while ensuring sufficient cash flow. To optimize execution, the conversions were automated on a monthly schedule. Based on conservative growth assumptions, the projected long-term tax savings amounted to $100,000.

Scene 5 - De-risking legacy GOOG without losing the story

Years of vesting had left Arjun with a heavy GOOG tilt. Rather than carry concentrated risk into startup life, we agreed on a gradual trim and reinvested the proceeds into a more balanced portfolio of ETFs plus a short-duration bond sleeve for liquidity. The shift reduced exposure to a single stock and steadied their runway, without cutting off growth potential.

Scene 6 - Planting the flag for the future

We drafted the bones of an irrevocable trust for eventual founder shares (to be funded when valuation, timing, and counsel aligned). Not a rush job, just the scaffolding so that when value appeared, the estate plan didn’t lag reality.

Where Arjun ended up

Cash flow relief: Withholdings lowered by ~20%, putting dollars back into the household budget.
Lifetime tax win: Roth conversions locked in a projected $100K of tax savings.
Portfolio balance: Concentration risk reduced while keeping room for growth.‍
Future-ready: Health benefits and estate plan aligned with their new life chapter.

Behind the scenes (our toolkit)

Tax projection & Roth modeling • Withholding & quarterly tax tune-up • Health plan decision model (HSA vs PPO) • Portfolio diversification strategy • Bond sleeve for liquidity • Estate planning checklist

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