BUSINESS OWNER MONEY QUESTIONS

10 Money Questions Successful Business Owners Should Be Asking

You don't need ten more financial products. You may just need ten better questions.

These are the questions I'd want on the table if we were looking at the wealth you've built inside and outside your business. You don't need to solve all ten today. Start with the one that makes you think, yeah, I probably should know that.

01

Am I keeping too much cash in my business?

Cash can be doing an important job: payroll, taxes, reserves, an acquisition, or simply buying you time. The problem isn't having cash. It's having cash with no clear reason for being there. I'd separate what the business actually needs from what has simply accumulated, then decide what job the excess should have.

Go deeper: How much cash should I keep in my business? →
02

What should I be doing with excess profits?

A great year creates a good problem. Reinvest in the business? Build reserves? Pay down debt? Take a distribution? Invest personally? There isn't one automatic answer. The better question is where the next dollar can create the most value without taking risk you don't need to take.

Go deeper: What should I do with excess business cash? →
03

How much of my net worth is tied to my business?

Your business may be the reason you've built meaningful wealth. That doesn't automatically make concentration bad. But I want you to know how much of your future depends on one company, one industry, and often one person: you. Then we can decide whether that concentration is intentional.

Go deeper: How much of my net worth should be tied to my business? →
04

Am I building enough wealth outside the company?

Business owners are often excellent at reinvesting in the asset they know best. At some point, though, the wealth outside the company needs its own strategy. That can create flexibility, reduce dependence on a future sale, and give your personal money jobs that have nothing to do with the next quarter.

Go deeper: How do I build wealth outside my business? →
05

Am I paying more in taxes than I need to?

Taxes touch business cash, investing, retirement plans, charitable giving, and eventually a sale. That doesn't mean every tax bill is a problem. I want to know whether your business, investments, and tax planning are being considered together, and whether a tax-saving move actually leaves you better off after the tradeoffs.

Go deeper: How can I reduce taxes on my investments? →
06

Is my personal investment strategy coordinated with my business?

Your business is already a major part of your financial life. Your personal portfolio shouldn't be designed as if the business doesn't exist. Liquidity, risk, income needs, taxes, and future opportunities all look different when we consider the whole picture instead of treating every account separately.

Go deeper: How I think about Capital Clarity →
07

What happens financially if I can't work tomorrow?

This is less fun to talk about, which is exactly why it gets ignored. I'd want to understand what happens to income, the business, debt, family obligations, ownership, and liquidity if you're suddenly unable to run the company. The goal isn't to predict disaster. It's to make sure one unexpected event doesn't get to make every other financial decision for you.

Go deeper: Explore risk and insurance planning →
08

What should I do before selling the business?

The best time to think about a sale is usually before the deal is already sitting in front of you. Taxes, deal structure, personal liquidity, estate and charitable planning, and what life looks like after the business can all be affected by decisions made before closing. I want the proceeds to have a plan before they become a pile of cash.

Go deeper: What should I do before selling my business? →
09

If I sold tomorrow, what would I do with the money?

A liquidity event can turn one familiar asset into a very unfamiliar financial life overnight. Before rushing to invest everything, I'd identify taxes and obligations, near-term liquidity, how much income the portfolio needs to create, what should stay safe, what can grow, and what decisions don't need to be made yet.

Go deeper: What should I do after selling my business? →
10

What am I not thinking about that I probably should be?

This may be the most valuable question on the list. Successful people usually aren't short on intelligence or effort. They're busy. A second set of eyes can uncover disconnected accounts, unnecessary risk, tax opportunities, outdated decisions, or simply money that no longer has a clear job. Sometimes the value is finding the question you didn't know to ask.

Go deeper: Ask Adam what is on your mind →
ONE MORE QUESTION

Still thinking? Good. That's kind of the point.

Good financial planning usually starts with better questions, not financial products.