For Lorilyn Wilson, CPA, PFS, chief of Lookahead Advisory’s Tax and Accounting division, a business’s taxes and accounts are a conduit. She uses them to guide not just tax compliance, but strategic planning and advising.
When getting to know clients, “we try not to talk about numbers. Instead, we talk with business owners about their businesses in their own words,” explains Kathy. “They tell us their story, and we learn how the business works.”
Whether for clients specifically seeking tax guidance and accounting advice or for enterprises engaged with Lookahead Advisory’s full suite of services, Lorilyn understands the importance of baseline business tax advice as a foundation for building success. That’s not only from her background and certifications. It’s from her own experience working in a small business.
“I can understand business people more,” says Lorilyn. “I can bring it down to a level the average person can digest.”
While Lorilyn didn’t come to accounting right away in her career, she quickly gained an understanding of the pain, fear, and dread entrepreneurs face around taxes and finances. After completing her undergrad at the University of Michigan in Ann Arbor, Lorilyn augmented her main job with her own small business, right down to keeping the books.“I was doing our taxes, but I didn’t know what I was doing.”
Those experiences in business and the uncertainty entrepreneurs faced around taxes propelled her to achieve certification as a Certified Public Accountant (CPA).
“When I entered the accounting world, I realized all these things I was doing and wasn’t sure about all the questions everyone had.”
Lorilyn understood firsthand how challenging it could be for a business owner to manage their own taxes. Whether they were looking through IRS forms and instructions directly or trying to follow guided approaches through popular tax preparation services, owners constantly felt in the dark. They were often unsure about whether they’d completed the right forms correctly or had missed a vital detail, form, or filing.
That scared, scrambling mindset presented another problem.
Since owners struggled with uncertainty about their taxes, they turned to any source they could for answers or direction, including social media. Unfortunately, those spaces tend to be full of misinformation.
“Everyone has the same questions and is making the same mistakes.”
Lorilyn realized she could reach more people faster via social media herself.
That understanding led Lorilyn to TikTok. Concerned about people taking the wrong actions from “a flood of misinformation on there,” Lorilyn decided to do her part to combat it.
“I could spend all day every day combating misinformation because it’s so prevalent,” she explains.
Posting insights and busting myths as @taxandwealth, Lorilyn “wanted to be a certified source of truth. Since I have a CPA behind my name, people say they know they can trust me and what I say.”
She encourages clients to seek their tax, financial, and accounting advice from professionals with relevant credentials, such as CPAs and tax attorneys, instead of relying on unverified information from social media.
”Be wary of where you get your information,” she suggests. “When in doubt, find someone with letters behind their name. There are reputable tax accounts that provide valuable information. Just because someone has a mic and music doesn’t mean they know what they’re talking about.”
Even when owners were taking care of their taxes and overall finances, they were only looking at short-term numbers, such as the previous quarter. They weren’t looking ahead to how they could better manage their taxes, implement accurate accounting, and then turn those improvements into strategies that furthered their profit numbers, business objectives, and personal goals.
“Over the past decade, I’ve guided hundreds of taxpayers in growing their businesses and wealth, while securing significant tax savings year over year,” says Lorilyn. “These results are only possible through a personalized approach to client engagement, thoughtful analysis, and commitment to making complex financial concepts clear and actionable.”
For a business to realize its potential and the goals of its stakeholders, owners not only deal with day-to-day operations challenges. They strive to push their business forward so they can grow in a way that meets their objectives. From understanding entity structuring to the need for professional tax consulting, accurate accounting and effective tax planning are key to realizing those goals and endeavors.
“This starts by addressing a common pain point: excessive tax liabilities,” explains Lorilyn. “Outside of tax compliance, I’ll work closely with you to create a personalized tax strategy designed to reduce your tax burden and open doors to long-term wealth-building opportunities.”
Key to that? Lorilyn helps her clients pivot to stop being fearful and reactive about their taxes and accounting. With proactive financial course corrections, Lorilyn not only ensures her clients comply with relevant tax laws and regulations. She sets them up to make their big dreams come into focus.
With a focus on fostering a community of financially empowered businesses and individuals, Lorilyn dove deep on talking through tax and accounting fears with her clients. As she listened, reviewed, analyzed, and discussed, Lorilyn drew on her background in business, training in accounting, and experience managing tax compliance and financials.
The real problem became clear, only it wasn’t taxes and accounting
After all, taxes and accounting are simply a baseline part of running a business. Unfortunately, they’ve become boogeymen that many owners consider so stressful, they avoid them—until a mandatory tax deadline or cash flow crisis forces them to start pulling in receipts and numbers.
Lorilyn showed her clients that their taxes aren’t the problem.
Uncertainty is.
“If people know what the tax number is in advance, then it doesn’t cause them stress,” explains Lorilyn. “If we’re projecting in June what they owe next April, they can handle it accordingly. Even if they can’t pay it, as long as they know the number, they stop stressing about it.”
When Lorilyn works with a client, she uses the numbers to provide clarity and peace of mind. Putting financials and her understanding of taxes to work, Lorilyn can accurately project in advance the tax liabilities of her clients.
Solid accounting does more than project good tax projections and filings. Accurate numbers are key not only to strategy, but to pursuing and procuring capital from lenders or investors. After all, businesses in a growth stage need to course correct in real time, while keeping sight of the bigger goals they’re working toward.
Whether she’s working with the books the business already kept or if she needs to do a from-the-ground-up financial reorganization, Lorilyn can provide whatever numbers and documents a business needs as they seek capital, such as updated profit and loss statements (P&Ls), copies of tax returns, copies of W2 forms, and more.
That goes for troubleshooting document problems too.
When a lender told Lorilyn’s client that a W2 didn’t match, Lorilyn dug into the problem. It turned out that the company’s payroll provider had mistakenly amended a W2, resulting in an inaccurate form.
“I could fix it in five minutes,” says Lorilyn. “By having my hands in the different pieces, I can get them what they need a lot quicker than if they were scrambling or trying to do it themselves.”
When the full Lookahead Advisory team problem-solves, develops solutions, and crafts strategies to evolve a client’s business, Lorilyn leverages the expertise of her colleagues. She also provides the tax and financial numbers the Lookahead Advisory team needs to lay the groundwork for every facet of their strategy recommendations.
“My conversations are all focused on tax,” says Lorilyn. “I bring clarity and peace of mind.”
Not only can Lorilyn provide clients with faster support. Her work means the team can base their initiatives on solid numbers. Together, the full Lookahead Advisory team can strategize for business growth, goal milestones, longer-term planning, exits, and more.
“Then we can lay the right foundation as they grow, or if they ultimately want to sell,” says Lorilyn. “Or if someone wants to stay right where they are, we can advise what they need to maintain or modify.”
It’s not uncommon for businesses to have messy bookkeeping, and sometimes none at all.
“The number one problem I see is businesses that don’t have accurate accounting,” explains Lorilyn. “You can’t plan anything if you don’t have good data.”
After all, when a business lacks a clear picture of their income, payroll, and operating expenses, own can’t put together a realistic road map of the future. Messy books make it impossible to strategize not only taxes, but also ways to leverage finances for more favorable tax circumstances, such as setting up retirement accounts, or modifying salaries and distributions.
“We need good data before we can make a good strategy, but that’s where people get stuck,” says Lorilyn. “Then people get stressed, and they put it off. Someone I spoke to today has three years of filings because she’s put it off. It’s cheaper to stay on top of it, to stay compliant in real time, when you find a pro you like working with.”
With a pro in your corner, it becomes easier to understand what constitutes a deductible expense, how to look at the tax ramifications of a financial decision, or how to block out business changes over quarters or years.
“Everyone needs a baseline level of tax advice.”
Understanding the right entity for now and upon reaching future milestones is essential too.
“Different entity structuring can affect your tax liabilities,” notes Lorilyn. “I see people getting into the wrong structure too fast, or they see something in social media that makes them think they need to be, say, an S corp.”
The key things to examine aren’t just which entity someone suggests in a short video online. Instead, it’s key to ask:
Lorilyn suggests that if your business is netting at least $140,000 a year, it’s time to engage, at minimum, a tax consultant.
Opportunity is what’s on the other side of fear, and an accountant can be far more than a tax prep pro. They can be your guide to how your business’s finances and accounting turn opportunities into met goals and realized vision.
The earlier a company engages a tax and accounting advisor, the sooner they can develop better forecasts and strategy both for short-term operations and long-term strategy goals such as growth levels, retirements, acquisition, or other objectives.
“Small business owners wear a lot of hats,” notes Lorilyn. “I’ve been on my own, and I’ve done marketing, financials, and IT on a low budget. You do more when you can outsource. I wished I’d leaned more on other pros instead of floundering on my own. Then you realize that your time and energy are worth more if you can focus it in one direction.”
A business can be intentional about strategy, taxes, and more when they have a good idea where the business is headed. As the business grows, and especially in a broader corporate or partnership structure, an engaged tax and accounting professional becomes vital. Key to that is moving beyond uncertainty and fear, and finding the team that can move your business forward.
“It’s impossible to keep up and keep compliant on your own,” says Lorilyn. “If you’re working with a pro, we’ll see those things that are coming five miles down the road that you don’t realize you’re going toward.”
At the same time, Lorilyn knows what it’s like to try to keep things going when you’re mostly on your own. She has worked with numerous businesses with messy financials—and even no financial records
“People come to me, saying they’re stressed and behind,” explains Lorilyn. “I tell them I’ve seen worse. We can get you sorted.”
