For business owners
You make decisions for the company all day. Your own finances have been standing in line behind every one of them.
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"I could tell you what the company brought in last Tuesday. I couldn't tell you what's in my own retirement account."
Owners tend to run their personal finances the way they'd never let anyone run the company: no reporting, no schedule, no one accountable. Not because you don't care. Because the business asks for something every single day, and your own money never does.
So it waits. The retirement plan you meant to look into, the coverage you set up years and one company ago, the accounts scattered across three custodians from three chapters of your life. None of it is broken enough to interrupt a Tuesday, so none of it gets a Tuesday.
I write more about what "enough" actually looks like on the Money & Happiness page.
I own and run this practice. I also helped start and scale my wife's multi-location med spa business, which means I've done payroll on a slow month, hired ahead of the revenue, and paid myself last.
So when you tell me the company is more than an asset, I'm not nodding politely. It's the thing you think about in the shower. It's how people introduce you at parties. Advisors who've only ever had a salary tend to hear "business owner" and think about a balance sheet. I hear it and think about your Sunday nights.
I'm also a Certified Exit Planning Advisor (CEPA), which is the credential behind the eventual handoff. That's a later chapter, and I'll come back to it below. It's not what most of our early conversations are about.
Because nothing is automatic. An employee gets enrolled in a retirement plan, handed a benefits package, and paid the same amount every two weeks. You get none of that by default. Every piece of your personal financial life is something you have to build on purpose, in whatever hours are left after running a company. That's a setup problem more than a discipline problem, which is good news, because setup is fixable in an afternoon and discipline isn't.
You have more options than an employee does. Depending on your income, your entity type, and whether you have employees, the usual candidates are a SEP IRA, a SIMPLE IRA, or a solo 401(k). They differ in how much income you can shelter, how much paperwork they carry, and what you owe employees who participate. Most owners I meet are in whichever one was easiest to open five years ago, which is a fine place to have started and a strange place to stay.
This is where most owner planning starts, because a plan built on an average month falls apart in a slow one. Usually that means paying yourself on a schedule you can count on, keeping a personal reserve that doesn't live in the company's account, and sizing what you save to a number the business could still manage in a bad quarter. Uneven income isn't something to fix. It's something to build around.
Your CPA files the returns and handles the company's tax structure. I don't prepare returns, and I don't touch your operations. My side is you: how you're paid, what you're saving, how you're invested, and what your family is covered for. Tax runs through all of that, but as timing rather than filing, since the choices you make during the year land on a return your CPA prepares the following spring. So I bring your CPA into those choices while they can still be made. More on that in tax planning.
Six areas come up in almost every conversation I have with an owner. All of them sit on your side of the ledger, not the company's.
SEP, SIMPLE, or solo 401(k), chosen around your income and your headcount.
Paying yourself, and saving, on a schedule that survives a slow quarter.
Your most controllable personal cost. I don't file returns, but I coordinate closely with your CPA.
One portfolio with a strategy, instead of accounts you opened at different points for different reasons.
Coverage sized to what your family relies on, rather than to a rule of thumb.
When the handoff moves from someday to a date, that's what the CEPA is for.
Every owner eventually stops being one. Sale, succession, or slow fade, it ends the same way: the company stops paying you, and something else has to. That day isn't today, and I'm not going to pretend otherwise to get your attention.
But it's the reason I hold the CEPA. When you get within a few years of it, the questions change, and I've written those out separately rather than crowd them in here.
A quick, useful starting point
1. Named beneficiaries override your will Beneficiary listings on investment accounts override your will entirely. Named an ex-spouse or a late parent? They still inherit, no matter what your will says…
A short, low-key call. We start with what you've got going on personally, and go from there.
Your personal finances. I'm not a consultant, I don't sit in on your operations, and I won't tell you how to price your services or hire your next manager. My side of the table is you: what you're saving, how you're invested, what your family is covered for, and how your personal taxes line up with how the company pays you. That said, I'm not coming at it cold. I own and run this practice, and I helped start and scale my wife's multi-location med spa business, so the uneven months, the reinvestment reflex, and the habit of paying yourself last aren't theoretical to me.
Because nothing is automatic. An employee gets enrolled in a retirement plan, handed a benefits package, and paid the same amount every two weeks. You get none of that by default. Every piece of your personal financial life is something you have to build on purpose, in the hours left over after running a company. That's a setup problem more than a discipline problem.
You have more options than an employee does. Depending on your income, your entity type, and whether you have employees, the common ones are a SEP IRA, a SIMPLE IRA, or a solo 401(k). They differ in how much income you can shelter, how much paperwork they carry, and what you owe employees who participate. Which one fits depends on your cash flow and your headcount, so it's worth choosing deliberately instead of picking whatever was easiest to open.
Most owner planning starts here, because a plan built on an average month falls apart in a slow one. The usual approach is to pay yourself on a schedule you can count on, keep a personal reserve that doesn't depend on the company's account, and size your saving to a number the business can sustain in a bad quarter rather than a good one. Uneven income isn't a problem to fix. It's a condition to plan around.
Your CPA files the returns and handles the company's tax structure, which is essential and a different job from mine. I don't prepare returns. What I do is look at your personal side, how you're paid, what you're saving, how you're invested, what's covered, and coordinate with your CPA so the tax strategy and the filing aren't pulling in opposite directions.
For most owners the exposure is wider than they expect, because the household income, the health coverage, and often the retirement savings all run through the company. The starting point is coverage sized to what your family actually relies on, along with enough liquidity outside the business that nobody has to make a rushed decision about the company on the worst week of their life.
CEPA stands for Certified Exit Planning Advisor. It's the credential behind the exit side of my practice, and it's the reason I can talk about a handoff before there's a buyer in the room rather than after. It doesn't come up much while you're building. It comes up a lot once you start thinking about what's next.
Yes, and most of my owner conversations have nothing to do with selling. They're about the things that got postponed while you built the company: retirement savings in your own name, investing with a strategy behind it, coverage that fits your family, and a personal tax picture that isn't an afterthought. The exit is a chapter you'll reach eventually. It isn't the reason to start.
Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.