By Cheryl Robinson,Contributor

Copyright forbes

Entrepreneurs who plan ahead by tracking expenses, preparing for taxes and asking tough financial questions set the foundation for lasting business success.

Entrepreneurship, in theory, sounds sexy. Being your own boss seems empowering. Executing an idea takes courage. Building out the business takes effort.

What holds many people back is understanding the financial aspects associated with launching a successful company. Genevieve George, CPA, CFP, CFE, CDFA and senior wealth advisor at Pelican Financial Planning and Wealth, has built her career guiding founders through the complexities of taxes, savings and long-term planning. Her message is clear: discipline on the front end prevents crises later.

Financial planning at the start of a company is a non-negotiable for startups. She explains, “Most entrepreneurs get surprised by taxes. I don’t love tax surprises, so I really preach that tax planning component.”

A 2021 Harris Poll survey commissioned by Zapier found that while 61% of Americans have dreamed of starting a business, and more than a third have imagined multiple ventures, only a small fraction act on those ambitions. In fact, 92% never take their ideas beyond the concept stage.

The survey identified funding challenges, a lack of health benefits, and limited access to tools and expertise as the primary barriers preventing would-be entrepreneurs from taking the leap.

Financial literacy is the first step toward turning an idea into a viable business.

Know Your Numbers

George’s first piece of advice is deceptively simple: understand the numbers that govern both your personal and professional life. “On the business side, you can’t make great decisions if you don’t have good data in front of you,” she said. Tracking expenses early prevents founders from making choices based solely on a bank balance rather than actual performance.

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She recommends that entrepreneurs adopt tools like QuickBooks and establish regular systems to monitor inflows and outflows. This dual awareness of personal budget and business metrics keeps founders grounded when opportunities or risks arise.

“You need to have an idea of what your actual budget is, what makes the world go round and what reserves you have,” George added.

Make Taxes A Year-Round Strategy

According to George, one of the biggest mistakes new entrepreneurs make is ignoring taxes until it’s too late. “The one that comes up the most is not really thinking about the taxes until after the fact,” she explained. That mistake can cost thousands.

For example, suppose an entrepreneur owes $20,000 in federal taxes at year-end but has not made quarterly payments. The penalty would accrue at about 0.67% per month on the underpaid balance. That could add up to $1,000–$1,500 in penalties for the year, depending on when payments were missed.

She urges founders to do tax planning in the third or fourth quarter, when they still have time to accelerate expenses or defer revenue strategically. For every dollar earned, she recommends setting aside a percentage in a separate account earmarked only for taxes. “It’s better if you can do tax planning before the year has ended, so you can make those shifts,” she said. Working with a CPA and financial planner ensures founders aren’t missing key deductions, credits, or structural advantages such as an S-corp election.

Genevieve George, CPA, CFP, CFE, CDFA senior wealth advisor and principal at Pelican Financial Planning and Wealth, creating a retirement strategy for her clients.
Jess McGillicuddy Photography

Build With The End in Mind

Beyond cash flow and taxes, George stresses the importance of long-term vision. Too many founders focus on surviving today without preparing for tomorrow. She advises clients to decide early whether their business is a personal legacy or an asset to be sold.

That choice influences decisions related to valuations and scalability.

“Even if it’s 10 years down the road, what are those things we should be doing now to keep it nice and clean and a marketable business for sale?” George asked. Regular valuations and systems that reduce dependency on the founder are essential for building enterprise value.

How You Can Start The Valuation Process Of Your Business

Engage a professional appraiser—Every few years, hire a valuation expert to provide an objective snapshot of the company’s worth, factoring in cash flow, assets and industry benchmarks.

Use financial multiples—Apply common valuation methods, such as revenue multiples or EBITDA (earnings before interest, taxes, depreciation and amortization) to track growth trends internally.

Benchmark against peers—Compare your company’s performance to similar businesses in your sector to understand where you stand and identify gaps that may affect marketability.

Ask Brave Business Questions

George encourages entrepreneurs to get comfortable asking what she calls “brave questions.” These are the difficult, sometimes uncomfortable conversations about money that many avoid out of fear or shame.

Fear often holds entrepreneurs back from asking the necessary questions. “They don’t want to know all the details because they’re afraid of what they are,” she said. “But the sooner you ask those questions and get the information you need, the sooner you can make those adjustments.”

For entrepreneurs, brave questions are a form of discipline. It forces them to confront reality early so they can course-correct before problems grow. Brave questions include:

What happens if my income slows or stops? Can the business and my household still survive?

Am I building this company to pass on, or to eventually sell? What should I be doing differently now based on that choice?

If I were to stop contributing to my retirement savings for five years, what would that mean for my long-term financial security?

Entrepreneurs who face their financial fears head-on give themselves freedom, the freedom to build with confidence rather than react with regret.

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