Faith, Pricing and Bootstrapping. Be Financially Literate.

As an IRS-licensed enrolled agent, the highest credential the government agency awards, Tai Stewart knows a thing or two about tax resolution, accounting, money, and finance for small businesses. Stewart, who has over 20 years of experience in the field, branched out in 2014 and began walking the talk of business ownership.

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In a conversation with Ramon Ray, Stewart shared insights about her entrepreneurial journey — from getting that first client to thriving in business and life. Here are some key takeaways to help create your road map for success.

A Leap of Faith

Stewart journeyed into entrepreneurship after years of working in CPA firms — a perhaps inevitable move, given her upbringing. Growing up, her parents instilled in her the importance of entrepreneurship and building generational wealth in the black community, inspiring her to venture into self-employment.

“The scary part, of course, is quitting your 9-to-5 — that steady, consistent income, having that paycheck every two weeks,” says Stewart. “So for a number of years, I kind of worked on the side but never really took the leap to completely go full time on my own.”

That is, until her last place of employment, one she describes as a “doozy” with a lot of drama and internal issues. Spurred to seize the day, Stewart knew it was time to take a calculated leap of faith and build her dream instead of only building other people’s businesses.

Determining Pricing

Upon quitting her job in June 2014, Stewart faced the challenges of maintaining a consistent income and work-life balance. Her first piece of advice: Don’t quit your job as soon as you have one client. Instead, have multiple clients lined up first to ensure financial stability.

Resourceful as she is, though, Stewart was determined to make her business work. She scoured job boards to source potential clients and pitched them on outsourcing accounting and bookkeeping services, offering a cost-effective alternative to hiring additional staff.

Initially, she charged just $50 for tax returns, and her business grew exponentially. However, she admits to facing a common entrepreneurial pitfall: keeping her pricing low out of fear that clients would consider her services too expensive.

“I was in a space where I was taking on any client — anybody and everybody — so I was charging way, way, way, way, way less than I should have been,” she recalls. “It was more about quantity versus quality clients back then.”

Balancing Finances and Business Growth

After joining various masterminds and accounting groups and learning from experienced colleagues, Stewart learned how to increase her prices to industry standards.

She also discovered how to develop a niche and serve the types of clients she enjoys working with the most. So, every year, her pricing has gone up little by little (not including the “family and friends” discount she offers loved ones, of course).

Working with a core group of clients you enjoy serving is not only more fulfilling but also helps to prevent burnout in business.

Additionally, Stewart recommends having six to 12 months of emergency funds saved before taking the plunge into full-time entrepreneurship. This buffer helps smooth out the financial rollercoaster and ease the stress that often accompanies startup ventures.

Another essential piece of advice she offers is the necessity of keeping personal and business finances separate. This practice not only ensures compliance with tax laws but also encourages good financial habits from the outset, such as maintaining accurate bookkeeping.

And if you’re thinking you’re too small to have accurate books, think again.

“The Schedule C business owners — those sole proprietors — are just as much if not more prone to getting audited,” Stewart warns. “Especially with all of the risk involved for filing fraudulent returns and people making up stuff, the smaller you are, I think the more they come after you.”

Leaning On a Support Team

Stewart further stresses the significance of assembling a team of professionals, including insurance agents, bankers, accountants, and attorneys, to assist in managing business finances and formulating an effective tax strategy.

In addition, Stewart advises having a solid understanding of the merits and drawbacks of various legal structures, whether an LLC, S corp, or corporation.

Don’t simply rely on some advice you heard on TikTok; lean on your team of professional advisors to identify the best legal structure for you, as it impacts taxes, liability, and operational flexibility.

Bootstrapping Your Way to Success

Stewart’s advice for new entrepreneurs is to keep things simple and bootstrapped, focusing on essential expenses and deductions in the first year of operation. This pragmatic approach ensures you’re allocating resources wisely and that the business remains financially sustainable.

And while the journey of entrepreneurship has ups and downs for anyone, Stewart’s insights are your cheat sheet for avoiding common pitfalls. By embracing the challenges and leaning on your professional support system, you’ll have an easier time clearing the hurdles and setting yourself up for long-term growth.

Stewart’s company, Saidia Financial Solutions, is a full-service accounting firm specializing in financial education and customized tax and accounting strategies. To learn more about Saidia’s online consulting and remote services, visit her website.

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