Dan Routh, CFP©

Helping Tech Execs & Founders Optimize Equity | Wealth Management | Partner at Old Peak Finance | Disclaimer: Posts = education, not personalized advice.

[Dan Routh, CFP© @EquityPlanDan]

I talk to executives every week about spending. They spend a lot, but have no idea where it goes. Lifestyle creep takes each raise, and they don't feel like they are getting the most out of their money.

They don't need to spend less; they need to change their spending to things they care about.

Block time this month to outline:

- The life experiences worth funding
- The family moments you won’t put off
- The impact you want to see while you’re alive

[Dan Routh, CFP© @EquityPlanDan]

I talk to executives every week about spending. They spend a lot, but have no idea where it goes. Lifestyle creep takes each raise, and they don't feel like they are getting the most out of their money.

They don't need to spend less; they need to change their spending to things they care about.

Block time this month to outline:

- The life experiences worth funding
- The family moments you won’t put off
- The impact you want to see while you’re alive

[Dan Routh, CFP© @EquityPlanDan]

Every person has an estate, no matter how much or how little money they have.

At a minimum, you need:

- A will
- Financial power of attorney
- Healthcare power of attorney
- A living will or advanced directive
- HIPAA releases

For our clients with higher net worths, they typically also set up revocable living trust(s).

The trust makes the estate process easier upon passing. Assets held in the trust don't have to go through probate court, which isn't the end of the world, but it reduces the burden on the people you leave behind.

The surprising thing is how many people with 7-8-figure net worths have none of this in place. Income is high, savings are strong, and career is going well. But nothing is planned for or documented.

If that's you, this is the year to get it done. We keep a list of estate attorneys we trust, and we're happy to make introductions.

[Dan Routh, CFP© @EquityPlanDan]

Everything looks great when the salary and stock compensation keep coming through the door.

But one of the first things we do with every new client is look at life insurance. And more often than not, high-earning couples either don't have enough or don't have any at all.

When something happens to the spouse making seven figures (especially when a large part of that income is stock compensation), household income could drop to nearly zero.

Everything stops. The stock grants. The salary. The savings.

We run a needs analysis for every client. What would the surviving spouse want? Is it wage replacement? Debt payoff? Financial independence? The ability to live as if nothing happened?

There's no right answer. It's very personal. But the conversation has to happen.

And it's almost always term insurance. It's straightforward, it's affordable relative to their income, and it solves the problem.

[Dan Routh, CFP© @EquityPlanDan]

All it takes is one number on your pay stub to create a tax problem you might not see until April.

The standard federal withholding rate on RSU compensation is 22%. If your effective tax rate is well above that, you've been falling behind every single quarter. When you're under-withholding on taxes, you really have two options.

Option 1: Make quarterly estimated payments yourself.

You calculate the shortfall, send a check to the IRS every quarter, and stay on top of it throughout the year.

Option 2: Increase your withholding rate to 37% through your employer

This lets the company handle it automatically. Instead of withholding 22 shares out of every 100, they withhold 37.

Both solve the same problem. The right choice depends on the situation.

If you have a great CPA who's proactive, who understands your compensation, and you're willing to manage the quarterly payments, option one works well.

If you'd rather not think about it and want life to be simpler, option two is usually the better choice.

[Dan Routh, CFP© @EquityPlanDan]

One of the hardest conversations we have with clients is about selling company stock that's done incredibly well.

They don't want to give up the upside. And I completely understand that. When a stock has gone up 500% or more, it feels wrong to sell.

But here's what we keep coming back to:

Your salary comes from this company. Your bonus comes from this company. Your RSUs come from this company. And now over 50% of your net worth is in this company's stock.

We've seen layoffs announced in tech every other week. When you really think about it, no job is ever really safe.

If you're still working there, more grants will continue to vest. We're never going to blindly recommend selling all of it, but we are going to manage that concentration as low as we can reasonably get it.

Concentration can build wealth. But at some point, you have to capture what's been built.

[Dan Routh, CFP© @EquityPlanDan]

We work with tech executives earning $500k–$1M+ a year who are navigating RSUs, options, and concentrated stock positions.

If you want coordinated planning across investments, taxes, and estate strategy, start here:

https://t.co/i2sHfJvztR

[Dan Routh, CFP© @EquityPlanDan]

You can owe thousands in taxes without ever making a trade on your own.

Capital gain distributions are the gift that keeps on giving in December.

You can avoid or minimize it by checking your mutual fund holdings early in Q4.

We just did this for all of our clients.

Fund managers trade all year long and get to pass on those gains to the shareholders.

Very active funds distribute more, meaning your tax bill goes up, with no control.

ETFs, index funds, and some mutual funds don't pay distributions at all.

Selling and moving into tax-efficient funds now (even with a big tax bill) can make sense.

Minimizing your lifetime tax bill is more important than one single year.

[Dan Routh, CFP© @EquityPlanDan]

Adding a small private deal can delay your taxes for months. The K-1 can show up just before filing, but still not be final.

Before you invest, ask the fund managers a few questions:

- When are K-1s sent?
- Are they final or just estimates?
- Does the timing fit how you file?

Clear expectations with the fund make your tax season faster, calmer, and easier to manage.

[Dan Routh, CFP© @EquityPlanDan]

Irrevocable trusts aren't a cure-all for ultra-high net worth estate planning.

Families turn to these types of trusts when:

-Their net worth exceeds the estate tax exemption.
-They want future growth to occur outside of their estate (business assets, PE, VC, high growth public equities)

You can add all sorts of control features and privacy tools, though it is not required or often worth the headache.

When structured properly, an irrevocable trust can move real dollars out of an estate while avoiding the unintended headaches that come with more aggressive strategies.

[Dan Routh, CFP© @EquityPlanDan]

There are families with $10M to $15M estates that spend thousands on a living trusts, then forget to fund.

Their accounts still list their personal names. Not the trust.

When that happens, everything they paid and planned for is skipped. Assets pass through the courts anyway.

To fix it, you have to retitle your brokerage and bank accounts in the trust’s name. Remember change ownership of private investments also. Then update beneficiary designations as needed.

After that, make sure to review it once a year.

A trust only works if you fund it.

[Dan Routh, CFP© @EquityPlanDan]

You can sell your company for eight figures and still feel lost the next year.

The deal closes, the wire hits your bank account, and life gets quiet.

What's your next move?

Clients tell me this period of time feels quite strange. Their days have no structure, and they do not know what to do next.

They worked hard for so long that having nothing to do feels empty.

When this happens, we work with them to create a plan:

1. Talk through goals and what you want to do next (if married, include your spouse).
2. Pause before any big changes.
3. Review new offers, projects, and investments slowly.
4. Build a new routine.

Planning ahead gives you room to breathe and space to build a life that feels good after the exit.

[Dan Routh, CFP© @EquityPlanDan]

Some founders are shocked when their “boring" cash account triggers a major tax bill.

Money market funds are earning 3–5% right now, which is great post-exit as you decide what to do next.

But the IRS is taking its share too.

Interest earned in money market and high-yield savings is taxed at ordinary income rates. If you earned $300K in interest this year, that can quickly bump up your tax bill.

Review where your cash sits and how much makes sense to keep. Otherwise, you may be able to get it to work, improving both return and tax efficiency.

Cash may be risk-free or low-risk, but not tax-free.

[Dan Routh, CFP© @EquityPlanDan]

We work with tech executives earning $500k–$1M+ a year who are navigating RSUs, options, and concentrated stock positions.

If you want coordinated planning across investments, taxes, and estate strategy, start here:

https://t.co/i2sHfJvztR

[Dan Routh, CFP© @EquityPlanDan]

Your estate strategy might be built on outdated numbers. Planning with old laws can cost you.

The estate exemption was made permanent by the One Big Beautiful Bill Act in 2025.

A married couple can now pass $30M without owing federal estate tax. That change affects:

- Annual & lifetime gifting
- Trust planning
- Tax optimization

Here’s what you can do now:

1. Use the annual exclusion limit. $19k per person, or $38k as a couple to any individual.

2. Frontload 529 contributions if it fits your goals.

3. Make sure your trust(s) have been created and funded (assets titled correctly).

4. Review whether lifetime gifts make sense before limits potentially change again.

5. Consider the hassle factor: don't let the tax tail wag the dog. Don't cause more headaches than tax savings.

These moves give founders and executives more control and fewer surprises later.

[Dan Routh, CFP© @EquityPlanDan]

More money makes life easier.

But the type of assets you own can add work you didn’t plan for.

Want less stress?

Start cutting down the parts that cause headaches or slow you down.

Merge old accounts - roll old 401ks into an IRA
Minimize private investments that hold up your tax filings
Rethink those "passive" real estate investments (rarely are they actually hands-off)
Make a plan for those RSUs you have put off selling

Only keep what you want to manage every year.

[Dan Routh, CFP© @EquityPlanDan]

After a liquidity event, some founders want to re-invest right away.

Don't rush.

Before you invest, spend, or lock up the money in a private deal, take a pause.

Set aside cash for taxes, debt payoff, and big upcoming expenses.

Give yourself time to reset before deciding what’s next.

[Dan Routh, CFP© @EquityPlanDan]

We work with tech executives earning $500k–$1M+ a year who are navigating RSUs, options, and concentrated stock positions.

If you want coordinated planning across investments, taxes, and estate strategy, start here:

https://t.co/i2sHfJvztR

[Dan Routh, CFP© @EquityPlanDan]

Advice I give every 7-8-figure tech exec:

If you're planning to move, make sure you review your equity compensation.

Recognition of income can follow you across state lines.

Don't assume:

- A new state means new rules
- Timing doesn’t matter
- Equity comp taxation is simple

Because it isn’t.

California knows this. New York knows this.

States will claim tax revenue for years after you move.

You need to know it too.

- Review your equity comp grant & vesting schedule
- Plan everything before you leave
- Work with Financial & Tax Advisors who specialize in equity comp

[Dan Routh, CFP© @EquityPlanDan]

Most people focus on "saving more" or "cutting expenses" to get wealthy.

That only takes you part of the way.

If you want to build true wealth ($10M+), you have to control more variables.

Across decades, not just this year.

What makes the difference?

- Increasing income
- Equity ownership in your company
- Minimizing taxes over your lifetime
- Portfolio construction

Wealth builds when you optimize for the future, not just today.