From paycheck to runway: preserving wealth in a founder’s first year

Scene 0 - Trading a steady paycheck for startup uncertainty

Meet Neha, 32, living in Seattle. After nearly a decade at Microsoft, she’d built a $780K portfolio across cash, ETFs, and savings. But when she left to bootstrap her own AI startup, the steady paycheck, bonuses, and benefits disappeared overnight.

On her last day in Redmond, she shut her corporate laptop for the final time. By Monday, she was in a co-working loft downtown, sketching architecture diagrams on a whiteboard. The excitement of building something new was real; so was the math. Without W-2 income, her investments now had to double as both safety net and startup runway.

Scene 1 - Counting months, not millions

Her first question: how long would funds last? Alphanso mapped out 14 months of runway across cash, a brokerage account, and a small cushion from savings. To extend it, we shifted idle cash into short-term treasuries and a California muni ladder. The result: liquidity intact, plus three more months of cushion without adding risk.

Scene 2 - A low-income year becomes an opportunity

With her W-2 income down 80%, Neha faced a much lower tax bracket. What looked like a setback turned into strategy:

• Partial Roth conversions staged across the year, keeping her under the 22% bracket.
  
• Tax-loss harvesting on older stock positions, banking $9K in offsets.
  
• Right-sized retirement contributions, preserving benefits without draining liquidity.
  

Projected outcome: a six-figure lifetime tax win from one “lean” year.

Scene 3 - Benefits without bloat

Open enrollment arrived just as she left Microsoft. Instead of sticking with a pricey PPO, we modeled health costs under an HSA-eligible HDHP. The HDHP won, saving ~$2,400 in premiums. The difference was redirected into the HSA, doubling as a tax shelter and future health fund.

Scene 4 - Concentration capped

95% of Neha’s potential wealth was tied to her previous employer (MSFT). To balance it, Alphanso set a concentration cap: no more than 20% of her investable wealth in the company. Gains from the proceeds were invested in other growth stocks and were paired with tax-loss harvesting. The goal was simple: keep the portfolio growth story intact while reducing the risk from sock concentration.

Scene 5 - Planting seeds for tomorrow

Even in year one, it wasn’t too early to prepare. We drafted the framework for an irrevocable trust to hold founder shares when valuation milestones hit. Not funded yet, just scaffolding, so the estate plan wouldn’t lag behind the company’s trajectory.

Scene 6 - Cross-country ties, no double taxation

Neha had moved to the U.S. from India a few years earlier, still holding savings accounts abroad. Dual reporting requirements meant extra complexity. Alphanso coordinated with tax counsel to:

• Map U.S.–India treaty rules on dividends and interest.
  
• Ensure FBAR and FATCA compliance without extra headaches.
  
• Apply foreign tax credits to avoid double taxation on overseas earnings.
  

What could have been a hidden risk turned into a clean, compliant setup, with no surprise tax bills down the road.

Where Neha ended up

• Runway extended: from 14 to 17 months through liquidity moves.
  
• Lifetime tax win: Roth conversions and harvested losses projected ~$110K in savings.
  
• Portfolio balance: Microsoft concentration reduced, stability added with similar stocks and ETFs.
  
• Cross-border compliant: No double taxation or reporting missteps.
  
• Future-ready: Health coverage and estate scaffolding aligned with founder life.
  

Behind the scenes (our toolkit)

Runway & liquidity modeling • Roth conversion tranches • Tax-loss harvesting engine • HSA vs PPO decision model • Concentration guardrails & ETF sleeve • Estate planning checklist • Cross-border tax coordination (FBAR/FATCA + treaty credits)

💡 Drawn from real client work, this case study blends insights from several founders. Identifying details have been changed to preserve confidentiality.