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Financial Planning For Small Business Owners

Are you a small business owner?


This might strike you as a ridiculous/obvious question but we meet plenty of people that don’t consider themselves small business owners…but that’s exactly what they are! 

From a financial planning perspective, a small business owner is anyone with 1099 self-employment income that is not dependent on any W2 salary with benefits. So you may be an independent contractor, a freelance consultant, or a one-person branding agency with no employees…but really, you’re a small business owner.

Free Webinar Series:

"Designing Your Financial Life Plan® for 1099 Income Earners"

Hosted by: Gideon Drucker, CFP®, AIF®, Equity Compensation Associate®

Tuesday, February 7th 2023 @ 6:00pm

REGISTER HERE

As a small business owner you are likely responsible for handling the following:

  • Setting up your retirement plans...
    You have no 401k that you simply auto-enroll into on your first day of work.
  • Setting up your own life insurance & disability insurance...
    Again, there’s no open enrollment where you just click & sign up for the group coverage.
  • Paying your tax estimates...
    This is probably the greatest change when you move on from your W2 salary…you become responsible for proactively paying your taxes rather than having them be withheld from a paycheck.
  • Separating your business from your personal/family finances...
    We will discuss this more below…but this is super important. The more you can cleanly separate the money that is to remain in your business versus the money you NEED to take out of the business to support your family’s future financial goals- buying a home, funding college, travel etc. the easier it will be to know BOTH are adequately covered.
  • Setting up your own Health Insurance through a state or national exchange...
    If eligible, you can go on your spouse’s employer plan if you’re married.

Running Your Small Business Comes With Many Financial Benefits...

This may look like it’s a lot that you have to manage on your own, and well, it is! That’s why it’s helpful to have a financial planning team in your corner helping you to make these strategic decisions and be laser focused on your personal financial goals so you can continue focusing on your business! We help small business owners design their own Financial Life Plan®. As a small business owner myself, I’d also add that some of these added complications are ultimately good things. For example:

  • High incoming 1099 income earners can save more money into retirement accounts than their W2 counterpart because Solo 401k’s & SEP IRA have greater contribution limits than corporate 401k’s.
  • You typically will have more adequate life insurance & disability insurance coverage than the average person because it is a more pressing priority from day 1 (as you didn’t have any employer coverage to fall back on.) Too many people with employer sponsored insurance coverage assume that plan is all they need & and are grossly underinsured as a result. Self-employed people that take the time to get the coverage they need are less likely to be in that position.
  • You can devise your own tax structure (LLC, S Corp, Sole Proprietorship, Partnership etc.) that best fits with your chosen business and the type of income you want to earn long term. You can also choose to pay tax estimates in a way that best fits with your cash flow & the way you best operate.

And don't just take our word for it... read what our small business owner clients are saying about us on Google!


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What sort of business owners do we currently work with?

  • Physicians & Dentists
  • Marketing/Branding Consultants
  • Sales Executives
  • Social Media Strategists
  • Design Agencies
  • E-Commerce Businesses
  • Interior Designers
  • Real Estate Brokers


What sort of entities do these small business owners employ?

  • Unincorporated (Freelance/Project Based)
  • S Corporations
  • LLC’s (taxed as an S Corp)
  • LLC’s (taxed as a partnership)
  • Sole-Proprietorships

We've put together a high level discussion regarding some of these options and outlined the various benefits of each entity type, which you can read here.


What sort of retirement plans do we set up for small business owners once they've completed a Financial Life Plan?

  • SEP IRA
  • Solo 401k
  • Simple IRA
  • Backdoor Roth IRA
  • Traditional IRA
  • Corporate 401k
  • Health Savings Account


What does personal financial planning look like for a small business owner? 

We love working with small business owners/1099 income earners. The number one thing I explain to our small business owner clients is that our job is NOT to focus on your business but to dedicate our team & energy to your PERSONAL (and family’s) financial outlook.

You most likely already have a CPA and bookkeeper handling your quarterly estimates, prep & filing, payroll (if you have it) and business tax returns (if you have an S Corp or LLC) and If not…we can always introduce you to our network. Their job is to make sure the finances of the business are running smoothly. Ours is different. Our is to make sure that you have a clear understanding of your family’s financial situation and what it will take to maximize the money that you’re earning FROM the business.


We help small business owners answer questions such as:

  • How much money do you need to be saving each month to hit your specific goals? Is what you’re currently doing enough to send your daughter to college? To buy your primary home?
  • How we should be allocating those savings among the different investment options available to you? How do you balance investing for retirement with investing/saving for a home?
  • What’s the best retirement account to set up for you? How much should we adding & how should we investing that money once the account is set up?
  • Should we be focused on saving into Pre-Tax Retirement Accounts or Roth (After Tax) based on your current income, tax bracket, and income trajectory?
  • Are your financial goals (retiring at age 55, paying for private school, traveling extensively, being philanthropic, buying your dream car etc.) achievable based on your current income, time horizon, and existing assets? What would need to change to make them feasible?
  • If you have children, what are the best saving vehicles for your goals as it relates to their futures? (529 Account, Custodian Accounts, Taxable accounts, trusts etc.) How much should you be saving for your children compared to your own financial goals?
  • Do you have a proper estate plan set up if you were to pass away prematurely? Do you have a will & health care proxy set up? Do you have chosen guardians, trustees, and fiduciaries set up to handle your assets?
  • You’ve been sitting in cash for a while as you keep earning more money…and you know your savings account is not actually growing but you don’t want to make a mistake in investing as it’s all new…
  • How much life insurance makes sense for you to have? Should you get term or permanent? What are the best companies to use?

How does a Financial Planner work with my CPA/Tax Attorney? 

First off, a number of 1099 income earners come to us wanting our help in finding a NEW CPA for themselves and their businesses and look to us to further educate them on how all of the different professionals will fit together on their behalf. We are happy to do so & enjoy being the first domino to fall for you! .

When it comes to the areas of our financial plan that will involve dissecting your tax returns & understanding your estimated tax liabilities, we will coordinate with your CPA.

Here are a few examples of what it looks like to coordinate your financial plan with your tax strategy:

  • As part of the initial planning process, we educate you on the differences between a SEP IRA and a Solo 401k as potential retirement accounts that you can use. We will look to your CPA to “run the numbers” and let us know what the maximum contribution you would be eligible make to each type of plan is…based on your income/expenses/deductions etc.. Once we have the numbers, we will then determine which is the more appropriate vehicle for you and determine how much we actually do want to fund your account with. Then, we will set up the account for you & design an appropriate investment strategy.
  • Let’s say, you have an S Corp already set up. We will look for confirmation from your CPA how much you are paying yourself as a W2 salary and how much you are expecting to take as an owner’s draw (profit distribution.) This information will be helpful in mapping out your cash flow & probabilities for success when we complete your initial Financial Life Plan® (FLP® ). We just want to make sure we are building your plan based on how you are actually paying yourself year-to-year. If we need to communicate with your CPA to understand that, we will absolutely do so (with your permission!)


How do I know if I am a good fit?

We deliver the greatest value when we focus on comprehensive planning that requires our expertise.

Our typical small business owner clients are:

Green checkmark Earning 1099 income over $200,000 Green checkmark Have questions about solo 401k, SEP IRA's, Life Insurance,  Disability Insurance etc.
Green checkmark   Have less than five full time W2 employees Green checkmark Ready to align investments with their goals, investment time horizon, and stage of life


If you’re like most hard working business owners and entrepreneurs…you have a lot going on.

You know there’s probably more you can be doing to reach your long term financial your goals…but you’re not exactly sure what that is.

You also know that to continuing being successful you constantly need to keep learning new ideas, tools, & strategies and craft a plan for your next level of growth.

We understand how important making the right decisions (at the right time) will be in your quest for financial independence & long term business success.

And maybe at this stage of your life you don’t have the time or desire to it all on your own. We get it! We want to take all of the worrying off your plate so you can focus on what you do best, running your business.

-Gideon Drucker, CFP® AIF® ECA, Managing Partner




Our Focus Is On Helping Small Business Owners Including:

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Dentists & Physicians

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Marketing & Brand Consultants

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Real Estate Brokers

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Sound Like You?

Book "Right Fit" Call

Are You a High Earning Business Owner Looking To Finally Get Your Finances In Order? 💪


Gideon brings his insights on helping clients avoid High Earner, Not Rich Yet syndrome in his book “How To Avoid HENRY Syndrome"