Dan Routh, CFP©

The biggest mistake founders make after a liquidity event? Reinvesting their cash too fast. Imagine this: A seven or eight-figure wire hits your account. Your immediate instinct is to "Put it back to work". Rushing kills any flexibility you could have had. Before you try and get another return you need to slow down: Step 1: Protect the cash. - FDIC covers $250K per person - Use Treasuries or money markets Step 2: Handle taxes. - Big exits mean >25% effective tax rates combining federal & state - Set money aside early for estimates. Step 3: Plan before you invest. - How much income do you need each year? - Does this investment fit your life goals or your risk? If you want to keep the wealth you worked hard for the best thing you can do is pause.

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: oldpeakfinance.com

I see it all the time: Founders who can retire tomorrow but don’t know what they’re working toward. Most of them feel stuck because they optimized for everything on the business side. But not the what comes after. They forgot to optimize for purpose. My happiest clients set goals for what they want the money to do. Time with family. Freedom to slow down. Impact beyond yourself. Funding causes they care about. Wealth without purpose feels empty. Ask yourself: What do I actually want this money to do for me and the people I love? Once you know that, every financial decision gets easier.

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: oldpeakfinance.com

The easiest way to lose control of your wealth is to assume your partner will figure it out when you're gone. It sounds like common knowledge. But it’s where even wealthy families fall apart. A few ways to fix it: Use the same password manager and CC both spouses on advisor emails. Make sure you keep a shared doc with account info, bills, and contacts. Do it while your life is calm. This way, if things get chaotic, you both will be ready.

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: oldpeakfinance.com

When I joined Old Peak, we decided on one rule: No cookie-cutter plans. We only work with clients who have a certain level of complexity. - Equity comp - Founder exits - Multi-state taxes The more moving parts, the more value we bring.

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: oldpeakfinance.com

When was the last time you made a financial decision based on your life goals instead of your tax bill?

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: oldpeakfinance.com

Equity compensation isn’t the same for everyone. How you plan depends entirely on your role. For example, public company execs don’t face the same problems as startup founders. One is about optimizing compensation. The other is about planning an exit (and a life after). Two different games entirely.

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: oldpeakfinance.com

A high salary isn't financial freedom. I’ve seen W-2 employees making $1M/year stress more than entrepreneurs. They earn high paychecks that come with brutal tax bills and no time freedom. Income and wealth aren't the same. Make sure you have someone in your corner to plan for every factor.

Investing can be really hard. When markets drop, we field emails and calls from clients who feel uneasy. We make time to talk through it with them. They are scared and uncomfortable, but they have a plan and are sticking to it. The hard part isn't the plan, but the "sticking to it" part. The feeling of needing to "just do something" can't be understated when you see the market falling. This is exactly the time when conviction in your investment strategy matters most. Decisions during volatility can have a lasting impact on long-term wealth, for better or worse. With an appropriate mix of risk (stock) and cushion (bonds/cash), we believe you shouldn't make reactionary changes to your portfolio. Actions to consider instead of selling to cash and waiting for stability: - Tax-loss harvesting - Rebalancing - Update your budget and financial plan We structure our client portfolios with decades in mind, matching the right amount of cushion to weather portfolio withdrawals for>7 years, even in the worst financial conditions. If you're feeling uncomfortable about your 401 (k), company stock exposure, or retirement portfolio, we are available to review and explain how you're positioned and what adjustments to make.

Holding a company’s stock out of loyalty can cost you. A founder I worked with sold his company. His new role came with restricted stock as part of the earnout, vesting annually over two years. He was loyal to the new company. But months later, the entire industry went through a market correction. His restricted stock dropped 30–50% multiple times. Through consistent planning and hard conversations, he did end up selling the majority of shares at each vest. That preserved as much wealth as possible before the declines. To this day, the stock has not recovered to the price at the original grant date. Remember, not every stock recovers. Make sure that's factored into your plan.

I had a founder who sold their company. Half cash upfront. The rest in RSUs + earnouts. Months later, the stock dropped 50%. We leaned on their goals, cash needs, and ability to take risks. We planned strategically before the sale. He decided to stick to selling shares at vest. This allowed them to still hit their goals, and mitigated their downside even further, as the stock to this day has yet to recover. Being disciplined always pays off. Hoping never does.

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: oldpeakfinance.com

Your CPA’s job is to minimize this year’s tax bill. Your advisor’s job is to minimize your lifetime tax bill. Most people confuse the two. That confusion can cost millions over the years if you're not working with the right person.

If you sold your company today for $20M+, what would you do for the next 10 years?

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: oldpeakfinance.com

Some founders sell their company, thinking money will solve everything. They never plan for what happens after (and it’s brutal). I’ve seen founders walk away with life-changing wealth, only to feel lost. They have no calendar and no drive. Their identity was tied too closely to what they built. That’s why every exit needs 2 plans: 1. Financial: tax, trusts, investments 2. Personal: life after the deal Without a plan, that wealth turns into frustration.