Confessions of an Entrepreneur Wealth Advisor
- Brendan Fraleigh
- May 30
- 8 min read
Updated: 6 days ago
Most people think the hardest part of building a business is getting it off the ground.
And sure, that is brutal. The early days, the uncertainty, the moments where you wonder if you made a massive mistake betting on yourself.
But after years of working with entrepreneurs, I can tell you that the financial mistakes I see most often do not happen in the early days.
They happen after the business starts working. When the revenue coming in is real. When the stress shifts from "will this survive" to "how do I manage what this has become."
That is exactly when the gaps in financial planning show up and when they are the most expensive.
I have worked with entrepreneurs who built genuinely impressive businesses and still found themselves in a difficult spot personally.
So here is what I wish more entrepreneurs knew before they needed to learn it the hard way.
In this blog, I am going to outline the mistakes I have watched successful entrepreneurs make and what I wish I could have told them before it was too late.
These are my confessions as an entrepreneur wealth advisor.
Confession #1: You Are Not Paying Quarterly Tax Estimates
For most of your adult life, taxes were something that happened to you automatically.
Your employer withheld the right amount on your W2. You filed in April. Maybe you got a refund. The system worked without you thinking much about it.
When you own a business, that system no longer exists.
Nobody is withholding anything. That is your responsibility. The IRS does not send you reminders about your future tax bill. The money hits your account and it all feels like yours, until it is not.
What I see over and over again is entrepreneurs who had a legitimately strong year financially, and then watched a massive chunk of it evaporate in March because they had no plan for what they actually owed.
And it is not just painful.
It is penalizable.
The IRS expects quarterly estimated payments throughout the year, and if you are not making them, you are paying extra for the privilege of being unprepared.
Here is the shift that changes everything:
Stop thinking about taxes once a year and start thinking about them every quarter.
There are four dates you need to be paying those quarterly tax estimates on:
April 15th
June 15th
September 15th
January 15th
These are non-negotiable.
This is why you need to bring in a wealth management team who has actually worked with business owners and understands how income flows, especially in a company like yours.
To summarize, you need to do the following:
Run quarterly tax projections.
Know your estimated liability.
Set money aside before it gets absorbed into the business or your personal spending.
Make the payments on a quarterly basis.
This is one of the most fixable problems in personal finance for entrepreneurs.
Confession #2: You Are Pulling Money Out of Your Business With No Real Strategy
Here is something I have noticed about entrepreneurs.
You are incredibly disciplined about how money moves inside the business.
But when it comes to your own compensation, you are making it up as you go.
Money is being pulled out when you need it based entirely on what the moment requires, not what a plan would suggest.
I understand why this happens.
It is your business and the money is yours.
And in the early days especially, taking a formal salary feels almost beside the point when everything is being reinvested anyway.
But here is what the absence of a distribution strategy actually costs you.
You have no clear picture of what you are personally making.
Your tax situation becomes harder to manage because your income is inconsistent and unplanned.
And you end up making personal financial decisions like what you can afford, what you save, and what you invest based on a moving target instead of a real number.
A deliberate distribution strategy means deciding in advance what you need, what the business needs to retain, and how to structure those distributions in a way that is efficient and sustainable.
It means treating yourself like the most important vendor in your business, because in a lot of ways, you are.
If you want more on this topic, check out this video that gives a real life example of what you can pay yourself as a business owner.
Confession #3: Your Business Is Your Greatest Investment
Most advisors will not tell you this.
But it is the truth.
Your business is not a liability to be managed around.
It is not a risk to be hedged against.
It is your greatest investment and it deserves to be treated like one.
What I see too often is advisors who build a financial plan that exists almost entirely independent of the business.
They manage the portfolio on the personal side, they do their job, and the business sits somewhere in the background; acknowledged but never truly accounted for.
That is a failure of planning, not a feature of it.
The advisor's job is to build around the business.
To understand what it is worth, what it generates, where it is going, and what it would mean for your personal financial life if everything went right, or if something went sideways.
And then to build a plan so strong around it that no matter where the business goes, your life does not change.
That is the standard.
Your business at the center, your financial plan built deliberately around it, and enough structure on the personal side that the outcome of the business does not determine the quality of the rest of your life.
If your wealth advisor has never framed it that way, that is worth paying attention to.
We put together an entire guide to Financial Planning for Business Owners. It is definitely worth checking out.
Confession #4: There Was No Financial Plan That Existed Outside the Business
Ask most entrepreneurs what their retirement plan looks like and they will describe their business.
"I'll sell it someday."
"It generates enough income to support us indefinitely."
"The equity is the plan."
Maybe.
But that is a significant amount of your future resting on a single outcome you do not fully control.
Valuations change.
Buyers are not always there when you are ready.
Businesses go through difficult periods.
And even the most successful exits rarely happen exactly the way you imagined.
What I have learned is that the entrepreneurs who feel the most financially secure, regardless of what happens with the business, are the ones who built something real on the personal side alongside what they built professionally.
That means using the retirement vehicles available to business owners, many of which are genuinely powerful and genuinely underused (yes, we have a guide for that too).
Solo 401(k)s. SEP IRAs. Simple IRAs. Defined benefit plans.
These tools exist specifically for people in your situation and can move serious money into a protected, tax-advantaged environment every year.
It also means having investments that are not tied to the performance of your business.
Because when the business has a hard year, and most businesses do at some point, you do not want your entire financial life feeling it at the same time.
The business is not your enemy here. It is your greatest asset. But it should not be your only one.
Confession #5: Business Money and Personal Money Were in the Same Pile
This one is more common than most entrepreneurs want to admit.
Business expenses on personal credit cards. Personal purchases running through the company account. A general sense that since it is all your money anyway, the details of where it lives probably do not matter that much.
They matter quite a bit, actually.
When business and personal finances are tangled together, a few things happen.
Your bookkeeping becomes a mess that costs extra to clean up at tax time.
You lose the ability to accurately read what the business actually costs to operate.
You create unnecessary exposure if the business is ever audited.
And you make it almost impossible to get a real, honest look at your personal financial picture separate from how the business is doing on any given month.
I have worked with entrepreneurs who genuinely could not tell me what they were earning personally.
Smart, successful people who had simply never drawn a clear line between their professional and personal finances.
The fix is not complicated.
A dedicated business account.
A clean, consistent way to pay yourself.
Expenses that live where they belong.
It is basic infrastructure, but it is the kind of infrastructure that makes everything else in your financial life easier to manage, easier to plan around, and easier to grow from.
Final Thought
I share these confessions because the entrepreneurs I respect most are the ones who want the full picture, not just the good news.
Building a business is hard.
Sustaining personal wealth alongside it is a different skill entirely.
And most people never tell you that until something goes wrong.
What I have seen is that the financial gaps rarely come from bad decisions.
They come from missing information, the wrong structure, or simply nobody in the room whose job it was to connect the dots between the business and the rest of your life.
That is the work we do at Moment Private Wealth.
If any of what you read here felt familiar, that is a good reason to have a conversation before it becomes something you are cleaning up instead of planning around.
Get in Touch With An Advisor
Frequently Asked Questions
Here are some answers to questions I receive frequently from entrepreneurs.
How does Moment Private Wealth help business owners with taxes?
Moment Private Wealth serves clients by running quarterly tax projections. Additionally, the firm works directly with your CPA to ensure all parties are on the same page, estimates are known and communicated to be paid in advance of deadlines.
Can Moment Private Wealth help business owners with succession planning?
Yes, this is part of creating a roadmap for your goals. Having first-hand knowledge of selling a business will allow you confidence throughout the process. Many business owners get one chance to sell a business. Having a firm that can help is key.
What does your average client look like?
Our clients are nearly all athletes and business owners. Our average client has a net worth greater than $5M. The strategies, solutions, and planning that we implement have a high-net-worth and ultra-high-net-worth client in mind.
Can Moment Private Wealth help set up retirement accounts for me as a business owner?
Moment Private Wealth uses Fidelity Investments as a third-party custodian for our client investment accounts. As a result, Moment is able to open IRAs, Solo 401(k)s and Defined Benefit plans and help manage those investments on your behalf.
Why should I consider hiring Moment Private Wealth?
Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or business owner interested in things like lowering your tax bill, investing smarter, and finding a trusted partner we might be a good fit.
*Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.
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