📈 “Should I Sell My Company Stock?” A Mid-Year Equity Checkup for Tech Professionals
Rohit Padmanabhan

📈 “Should I Sell My Company Stock?” A Mid-Year Equity Checkup for Tech Professionals

 

It’s July—halfway through the year, and right around the time when many public tech companies report earnings, vest RSUs, or reach post-IPO lockup expiration. If you’re a tech professional sitting on a growing (or shrinking) pile of equity compensation, now is the time to step back and ask:

 

Should I keep holding my company stock, or is it time to diversify?

 

We’re seeing this question come up more frequently in 2024 as tech sector volatility, Fed interest rate decisions, and recession whispers all begin to cloud the outlook. Many young professionals mistakenly treat their company stock like a long-term retirement asset—when in reality, it’s often better viewed as a bonus paycheck with a stock symbol.

This week’s post helps you revisit your equity strategy, make smarter tax-aware decisions, and reduce the risk of “paper wealth” turning into regret.

🎯 1. Understand What You Own—and When You Own It

 

Start by listing out your current equity holdings and upcoming grants. This includes:

  • RSUs (Restricted Stock Units) – When do they vest? What’s the value at vesting? Were they already taxed?

  • ISOs or NSOs – Do you have unexercised options? What’s the strike price? Is the clock ticking post-termination?

  • ESPP (Employee Stock Purchase Plan) – Are you buying shares at a discount? How long have you held them?

🔍 Real-world example: A client who left a fast-growing SaaS firm last fall still held unexercised NSOs with a 90-day post-termination clock. We identified the upcoming expiration and helped them exercise and convert early to minimize AMT exposure.

Advisory Note: We help you review and track all your equity pieces in one place and proactively model expiration timelines and tax outcomes.

💥 2. Watch Out for Concentration Risk

 

It’s common for tech professionals—especially startup employees and FAANG workers—to end up with 30%+ of their net worth tied to one company.

🚩 That’s a big red flag. 

 

Concentration in a single stock means:

  • If your company stumbles, your income and investments drop together

  • You're exposed to volatility you can’t control

  • It may feel like a smart bet now, but it’s risky over a 20-year horizon

⚠️ Example: Snap, Rivian (and even Meta) employees who rode the 2020-21 bull market often saw their equity go from millions to a fraction of that in 2023. Those who diversified early came out ahead, especially if they needed the cash.

We typically suggest creating a systematic equity sell-down plan—whether it’s tied to vesting dates or price thresholds—to slowly reduce your exposure and diversify.

💸 3. Don’t Let Taxes Drive the Whole Decision

 

Too often, clients hesitate to sell because they’re worried about the tax bill. Yes—capital gains and ordinary income taxes matter. But so does:

  • Reducing overexposure

  • Locking in gains while they’re real

  • Rebalancing into other long-term goals (like home down payments or retirement)

💡 Planning tip: For RSUs, the tax already hits at vesting—so any further gain is long-term capital gains (if held >1 year). For NSOs and ISOs, the timing of exercise and sale can drive huge tax outcomes—sometimes triggering AMT or losing qualified treatment.

We help you model each scenario side-by-side so you can choose the strategy that supports your actual goals—not just what saves the most on a tax form.

📊 4. Tie Your Equity Strategy to Your Bigger Financial Plan

 

Your company stock is a tool. It’s not a retirement plan, and it’s not a forever-hold asset for most people. It’s there to help fund:

  • Financial independence goals

  • Real estate purchases

  • A new business venture

  • Education savings for kids

  • Early retirement or part-time transitions

🌱 Let’s say you have $400k in vested RSUs and want to buy a home in 18–24 months. Locking in part of that now—before a downturn—may be more aligned with your goals than riding the wave and hoping for the best.

We often recommend creating a custom equity liquidation plan each year, tied to real targets and decision dates—not emotional price highs.

🚀 Final Thoughts: Think Like a CFO, Not a Fan

 

It’s tempting to treat your company stock like a badge of honor. But your job is to be the Chief Financial Officer of your own life—not just a loyal employee.

We’ll help you evaluate:

  • When to sell and how much

  • Which tax strategies (like tax-loss harvesting or charitable gifting) to use

  • Whether to hold long-term or shift to diversified investments

If you’ve received equity grants this year or have upcoming vesting dates, now’s the time for a mid-year review.

→ Ready to create your equity plan? Let’s map it out in a short review call and run the numbers. We’ll help you turn your stock into real wealth.

 

 

 

📝 Disclosures:
This content is for educational purposes only and should not be considered investment, tax, or legal advice. Please consult with your financial and tax advisors for personalized recommendations.

 

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