"Hey, Should I Sell My Tech Stock?" and Other Questions You're Asking Me Right Now

Over the past few weeks, I’ve been getting a steady stream of messages from friends — especially those of you in my Berkeley cohort and fellow professionals in tech — asking some version of the same thing:

“What should I do with my portfolio right now?”

“I’ve got a bunch of cash sitting idle. Should I invest it?”

“My company stock is way up/down/sideways... help?”

First off, I love these conversations. They tell me that you're engaged, aware, and thinking long-term. Also, it’s always good to hear from you! Even if the subtext is “please help me not make a dumb decision right now.”

The truth is that market volatility tends to stir up both excitement and anxiety. And when you’ve worked hard, are earning great money, and have a sizable portion of your net worth tied to one company (usually the one signing your paycheck), it’s completely normal to feel a little uneasy right now.

So whether you’re holding a ton of Restricted Stock Units (RSUs), debating what to do with your cash building on the sidelines, or just wanting to make smarter decisions for your future, here are three powerful strategies I often share with friends — and use with clients:

1. Diversify That Concentrated Tech Position (Even If You “Love the Company”)

You’re crushing it in your career, and your equity compensation is a big part of that. But holding a large percentage of your wealth in a single company — or even a single sector like tech — comes with major risk. You’re essentially betting your human capital and financial capital on the same outcome.

Start by building a plan to unwind your concentrated position over time. This could include:

Tax-aware selling strategies (think: harvesting losses in other areas or spreading gains across tax years)
Gifting appreciated stock to a Donor-Advised Fund — great for reducing your tax bill while supporting causes you care about. This is not for everyone and really depends on where you are in your overall financial situation.
Exercising and selling Incentive Stock Options (ISOs) or Non-Qualified Stock Options (NSOs) with careful planning to avoid Alternative Minimum Tax (AMT) surprises. This one is tricky and requires planning. Let a financial planner help you map this out.
Using an Exchange Fund to swap your single stock for shares in a diversified pool of equities — without triggering capital gains. Again, bring in a financial planner to help you with this. There are eligibility requirements, considerations, and caveats you need to consider.

And here’s the part that’s often overlooked: diversify beyond U.S. stocks. International and emerging markets offer exposure to different economic cycles, currency behavior, and geopolitical factors. Adding global equities can reduce your overall portfolio volatility and improve long-term risk-adjusted returns. Diversification isn’t just about adding more — it’s about adding different.

Diversifying beyond U.S. equities over the past three months has helped reduce portfolio volatility, as international markets showed relative strength while the S&P 500 has been declining. For example, while U.S. stocks stumble amid inflation concerns and new tariffs, European indices like the FTSE 100 and Stoxx 600 are experiencing gains, and Hong Kong's Hang Seng Index ended slightly positive in Q1, highlighting the value of global exposure in uncertain markets.

2. Put That Cash to Work (Strategically and Tax-Efficiently)

I know it’s tempting to let cash sit on the sidelines — especially when markets are swinging wildly. But sitting too long can mean missing opportunities for growth and compounding. The key is to be intentional.

If you’re unsure about the timing (which we should all be; market timing is a fool's game), dollar-cost averaging can help. By investing a set amount consistently over time, you smooth out the highs and lows — and remove the pressure of having to “guess right.”

Just as important: where you put different types of investments matters. This is called asset location — placing the right assets in the right accounts to reduce your tax drag. For example:

Tax-inefficient investments? Best held in tax-deferred accounts like a 401(k) or traditional IRA.

Tax-efficient ETFs or index funds? Great candidates for a brokerage account.

High-growth investments like small-cap or emerging markets? Consider putting these in a Roth IRA where the gains can grow tax-free.

Don’t let your cash just sit there. Let’s make a plan to put it to work in a way that fits your overall strategy — and minimizes taxes while doing it.

3. Rebalance, Reassess, and Stay Disciplined

You’ve been busy scaling your career, growing your family, maybe even launching a side hustle. But if you haven’t looked at your portfolio’s allocation lately, odds are it's drifted from your original plan.

Market movements can tilt your risk exposure without you realizing it. Rebalancing helps bring things back in line — whether that means trimming overperforming positions, adding to underweight areas, or reallocating based on changes in your life or goals.

And speaking of goals, this is a great time to revisit your plan altogether. Are you still aiming for the same outcomes? Has your risk tolerance changed? Do you need more liquidity?

Rebalancing isn’t just about numbers — it’s about keeping your portfolio aligned with your life.

Final Thoughts (and a Friendly Nudge)

If you’re feeling unsure, know this: you’re not alone! The questions you’re asking are smart, timely, and completely normal. The important thing is to take action from a place of strategy — not fear or FOMO.

As someone who works with high-earning professionals like you every day, I can help you create a plan that reflects your income, your goals, your timeline, and your values.

Whether it’s making a plan to unwind your stock position, putting your cash to work wisely, or just wanting to feel like your money has a plan — I'm here for that.

Shoot me a message. Let’s get your financial life organized, optimized, and working just as hard as you are.

~ Rachel Bubb

The information provided herein is for educational and illustrative purposes only and should not be construed as personalized investment, tax, or legal advice. Examples involving equity compensation, tax strategies, or asset allocation are hypothetical and meant to demonstrate general principles. You should consult with a qualified tax or financial professional before making decisions specific to your situation. Market data and index performance referenced are based on third-party sources believed to be reliable; however, accuracy and completeness cannot be guaranteed.

Sources:
https://www.ft.com/content/52a198c0-235b-4662-87cc-527c7cd79b4a
https://www.advisorperspectives.com/dshort/updates/2025/04/14/world-markets-watchlist-april-11-2025