One of my favorites things about my morning is my son and I going on a run together before I have to go off to work.
The highlight of the run is him wanting to go see the excavators (or what he calls escalators) at the nearby park building the future splash pad that I’m sure we will be at all the time in the summer to come.
One thing I am really working on throughout my busy schedule of raising our family, helping my clients while building my business, being involved in my community through the Rotary Club.
I’m really working on enjoying and appreciating each and every moment such as this and hope it’s a good reminder for you as well in your busy life to take a second each day to appreciate where you are, and who you are with
Watched the Ohio State Alumni Marching Band close out a summer night with Hang On Sloopy. Eight decades of alumni on one field. Some marched in the 1950s.
When the drum major gave the signal, everyone knew their part. Nobody had to relearn the song.
What you build deep enough does not expire.
Everything I know about money started with a coffee bean.
In college, I owned with a buddy of mine, a small coffee company called Hog Roast Coffee. No investors, no plan, just a product we believed in and a lot of learning the hard way.
Selling coffee taught me what a margin actually feels like. Not the definition in a textbook. The real thing, where the difference between profit and loss is a few cents a cup and you feel every one of them.
It taught me that a customer saying no is information, not an insult. And that a customer coming back a second time is worth more than ten who came once.
Years later I became a financial planner, and I noticed something funny. The people who understood money best were rarely the ones who studied it. They were the ones who had sold something. Run something. Sweated a payroll. Felt the cents.
You do not need a finance degree to build wealth. You need to have felt how money actually moves. A lemonade stand teaches it. A paper route teaches it. A scrappy little coffee company definitely teaches it.
If you ran anything as a kid or a college student, you know more than you think.
That coffee company is also why my weekly video series is called Wealth Espresso. And I have an idea brewing for where it goes next. It involves actual coffee shops. More soon.
Wealth Espresso | Episode 46
Dino's Cappuccinos
When you bought your last house, how many lenders did you compare? For most people the answer is one.
Rates and fees can differ between lenders, and a mortgage is one of the largest financial commitments most families ever make. Comparing a few options is usually worth the time.
Curious to hear your experience below.
Confession from paternity leave. After Simon went down for bed each night, Moriah and I spent most of it hanging with Elliott and watching Million Dollar Listing New York... Way too much of it!
I thought it was a show about fancy apartments. It is really a show about people whose lives are changing. Someone selling a business they built for 20 years. Someone who just came into money and is about to make the biggest purchase of their life.
That part felt familiar. It is basically what I see in my line of work.
Here is what got me though. I kept watching for the "secret sauce". How do these agents pull off a packed open house or a bidding war on a $10 million apartment?
Turns out the cameras skip the secret sauce because it is boring and not flashy/exciting. It is hundreds of phone calls nobody films. It is following up when nobody answers. It is showing up again the next day. Sprinkle in a little luck and that is the whole recipe. You see the champagne on TV. You do not see the grind.
There is also this moment where an agent starts selling out a building very quickly, that the pricing gets reworked and the win turns into a whole new negotiation. Winning did not end his problems. It just gave him different ones.
Same thing happens when your stock vests or your company goes public. That is not the finish line.
That is when a whole new set of decisions shows up.
Anyway. Ryan Serhant was right that the deal is never about the property. It is about what it means to the person.
If you have not watched it, I cannot even pick a favorite season. Each one is a different market but the same hustle. The secret sauce is not a secret. It is just work.
Tomorrow I'll be walking in the Sunbury-Galena parade, waving at neighbors, hearing the word "independence" about fifty times before lunch. Most people won't think twice about it.
But some of you already lived that word this year. On a vest date. An IPO. A tender offer. A liquidity event that changed the number in your account and changed what's possible for your life.
Here's the pattern I see almost every time.
The first calls are all technical. What do I do about tax withholding. Am I too concentrated in one stock. Should I exercise now or wait. Those questions matter, and I answer them. They're also the easy part. They have clean answers.
The hard question shows up later, if it shows up at all.
What is the money actually for?
Not "retirement." Not "financial security." Those answers sound complete but explain nothing. I mean specifically, in your life, with your family, what changes now. What do you do with freedom you technically have but haven't used yet.
I've met people three years past their liquidity event who are still living exactly like they did before it. Same schedule. Same worries. Same decisions they keep putting off. The stock did its job. Nobody ever went back and asked what it was for.
That's not a portfolio problem. Nobody had that conversation.
The technical work still matters. Tax exposure, concentration risk, exercise timing, none of that goes away. But it's the first step, not the last one. What you do after is a different kind of planning, and it usually gets skipped because it doesn't come with a spreadsheet.
If you're sitting on a number and haven't asked yourself that question, you don't need to decide anything this week. You just need to actually ask it. On your own, or with someone who won't rush you past it to the next tax strategy.
That's the work I care about most. The technical planning gets you organized. The other conversation is what makes the money mean something.
Have a safe weekend, and Happy Fourth.
Russell Doup, CFP® | Director of Financial Planning | Maxwell Financial Management
Episode 44 | Wealth Espresso
Winn Winn Cafe. Second appearance for this spot on the show, if you haven’t been, it’s worth the visit.
Granola parfait and an iced vanilla latte this time.
Quick history note with your coffee this week. 250 years ago, 13 separate colonies signed the Declaration of Independence in Philadelphia. One signature moment. Today, a 27 trillion dollar economy.
Worth thinking about next time you’re building something of your own, a business, a career, or a plan for your family. 250 years of compounding started somewhere.
Source in the below.
Have a great and safe 4th this weekend.
For anyone looking at accounts this week, you can typically find your exact vesting schedule and histories on platforms like Carta, Shareworks, or Schwab. Because equity can get complicated depending on your tax bracket, it’s always a good idea to sync with a CPA to review your specific numbers.
If your company vests on a quarterly schedule, you probably had shares settle sometime in the last 90 days.
Here is the question most people skip: What did you do with them?
The most common answer is "nothing." The shares land in the account, you see the number, and life keeps moving.
But doing nothing is still an active decision. It means choosing to maintain your current position without review.
When your salary, bonus, and equity all come from the same employer, your personal financial picture is heavily tied to a single entity.
Half the year is gone.
If you have not evaluated your overall equity picture since January, now is a baseline time to review three areas:
1. Tax Withholding: Automated company withholdings on equity may not automatically align with your personal effective tax bracket.
2. Concentration Level: The percentage of your total net worth tied up in employer stock can drift over time as shares vest.
3. Financial Alignment: Assessing whether holding or diversifying aligns with your broader financial framework.
Reviewing your documentation can help you understand your current baseline.
Episode 43 of Wealth Espresso.
This one took me back to Fox in the Snow in Westerville. I ordered the New Orleans cold brew, which is steeped with chicory.
Here is the interesting part. Drink that cold brew by itself and it is bitter, almost too bitter to finish. Add a splash of milk and it turns into something smooth and easy to drink. Same coffee, same chicory, completely different experience depending on how you take it.
That made me think about something that happened today. I checked the radar this morning and it said no rain until 8 PM. It is the middle of the day right now and it is raining.
Financial planning works the same way. We do the work. We build the plan. We prepare for what the data tells us to expect. But the word “planning” has to leave room for things not going as expected, because they often do not.
A good financial plan is not the one that predicts the future perfectly. It is the one that can flex when the forecast is wrong and still get you to where you are trying to go.
So yesterday was a wild one.
My wife and our two kids were having a picnic in the yard. Just hanging out, eating lunch, nothing crazy. Meanwhile, twenty feet away on our front porch, there was a raccoon hanging out in the cat house for our cat, Gilly. Nobody invited it. Nobody even knew it was in there.
My wife walked over toward the porch and went to pet what she thought was either Gilly or a neighborhood cat and the thing did some angry growl at her!!
No one got hurt though. Big sigh of relief on that one. Sunbury Police actually showed up, scooped up the whole cat house, raccoon and all, and said they were going to let it go at a park. So somewhere out there is a very confused raccoon starting a new life.
Here’s the part that got stuck in my brain though. That cat house looked completely normal from the outside. You’d never know something else had moved in. And my family was twenty feet away having a nice afternoon with zero clue.
That is basically what happens with money too. People build their financial setup for one version of their life. A 401k from their first job. A stock plan they never really look at. Then real complexity moves in quietly, RSUs, a company going public, a stock grant that suddenly doubles, and nobody notices because everything still looks fine from the yard.
The scary part is never the bite. It is not knowing something is already on the porch.
That is what I call an equity inflection. The complexity shows up right when the wealth does, and it usually shows up quiet.
So, anyone else got something hanging out on their financial porch they have not checked on in a while?
Wealth Espresso | Episode 40
Today’s stop: Little Lemons Play Café in Sunbury. Great cold brew and you can actually sit and watch the kids play. Nice local spot if you have little ones.
This week’s topic: nearing IPOs and managing the excitement.
#WealthEspresso
Stocks often rise fast after they go public then settle back down. When excitement builds around an IPO, some investors use dollar cost averaging as one way to manage the decision. It can help reduce the impact of emotion on timing.
Most people build the portfolio before they have the conversation.
Three questions that come first, and none are about money.
Until you have them, you do not have a plan. You have a portfolio.
Your job is to be excellent at the thing you actually do. It was never to be a tax attorney and a securities lawyer on the side.
Wrote a piece on this. Link below.