EP 60: Plan Before the Pain: Pain Points of Taxes, Transitions, and Business Ownership

August 18th

By: StaffBuffalo Team

Running a business is about much more than getting the numbers right. Behind every tax return, acquisition, succession plan, or hiring decision are people navigating change, uncertainty, and decisions that can shape their futures.

On this episode of the Pain Points Podcast, Maggie Shea sits down with Ashley Sixt Gerhard, CPA, Partner at Sixt Gerhard & Associates CPAs, PLLC, to discuss Ashley’s path into accounting, taking on leadership at a pivotal moment, and the lessons she has learned helping small business owners navigate growth, acquisitions, retirement, and succession planning.

Their discussion also offers an insightful look at how the accounting profession is changing and why relationships, preparation, and trusted advice remain more important than ever.

From a Family Business to Accounting

Entrepreneurship was part of Ashley’s life long before she became a CPA.

She grew up around a multigenerational family lumberyard and initially entered college as a math major. After realizing that a traditional math career was not the right fit, she began moving toward accounting and finance.

An internship at her great uncle’s accounting practice helped solidify that direction. Ashley started during an era when tax returns were still assembled and filed on paper, giving her a firsthand look at the profession from the ground up.

After college, she gained experience in managerial accounting and helped her husband with his own business before eventually returning to the accounting firm part time.

That part-time role continued to grow. Eventually, Ashley pursued her CPA and was approached by the firm’s existing leadership about taking over her great uncle’s role, an opportunity she had not been actively seeking.

Stepping Into Leadership During an Unprecedented Time

The firm planned its ownership transition for January 1, 2020.

Only months after Ashley stepped into her new leadership responsibilities, COVID-19 disrupted businesses everywhere.

For an accounting firm serving small business owners, the challenges multiplied quickly. Clients suddenly needed guidance on PPP, ERC, shutdowns, tax changes, and financial uncertainty. At the same time, the firm had to rapidly implement technology that would allow employees to work remotely.

Ashley had originally envisioned remote capabilities as part of a longer-term plan. Instead, the firm had to make it happen almost overnight.

The experience created enormous pressure and burnout, but it also accelerated changes that might otherwise have taken years.

As the business environment shifted again, Ashley faced another challenge: more clients and not enough accounting professionals.

But she did not want to solve the problem by simply hiring anyone available.

Accounting is complex, and client relationships are deeply personal. Bringing someone into the firm means trusting that person with relationships that have sometimes existed for decades.

That has led Ashley to focus on finding the right people, then helping each employee discover where they naturally excel.

Developing People While Embracing Change

Ashley believes new accountants need to understand more than how to complete individual tasks.

New team members are exposed to different parts of the business, including payroll, bookkeeping, QuickBooks, billing, tax preparation, and client service. This helps them understand how everything connects while also revealing the work they enjoy most.

Technology has transformed accounting, but Ashley does not believe every manual process should disappear.

One example is data entry.

While software providers increasingly offer automated scanning, pre-population, and offshore data entry services, Ashley sees tremendous educational value in having newer accountants enter information themselves.

When someone enters a W-2 or reconstructs a prior-year tax return, they learn where numbers belong, how information flows through tax software, and how one input affects another.

Automation can make processes faster, but accountants still need to understand what is happening behind the technology.

That philosophy connects to Ashley’s broader approach to leadership. As the firm has grown, she has become more intentional about identifying the strengths of individual employees and giving them opportunities to work in areas where they can contribute the most.

Through her own professional development, Ashley has also spent more time defining her vision for the firm and identifying the work that gives her the greatest sense of purpose.

For Ashley, that work often involves helping clients navigate complicated business transitions where numbers, strategy, and emotion intersect.

Buying, Selling, and Planning for the Future

Ashley has developed a particular interest in helping clients navigate business acquisitions and succession planning.

For buyers, her advice starts with due diligence.

A profit and loss statement is only one piece of the picture. Buyers need to understand multiple years of financial information, balance sheets, tax returns, financing arrangements, and exactly how a proposed transaction will be structured.

They also need the right professionals involved early.

Accountants and attorneys may approach a transaction from different perspectives, and that is valuable. The goal is to find a structure that makes sense legally while avoiding unnecessary financial or tax consequences.

Selling a business can be even more complicated because emotion becomes part of the equation.

For many owners, a business represents decades of work, sacrifice, relationships, and identity. That makes separating emotional value from financial value extremely difficult.

Ashley cautions business owners against treating the eventual sale of their company as their entire retirement plan. A business may have a valuation on paper, but ultimately it is worth what someone is willing to pay.

That is why succession planning should begin long before an owner wants to leave.

Ashley has seen successful transitions happen through family members and existing employees who already understand the organization, clients, and culture. She also sees value in gradual transitions where owners remain involved as consultants before fully stepping away.

The earlier those possibilities are considered, the more options an owner has.

Building a Business That Can Thrive for the Long Term

One of Ashley’s strongest messages for clients is simple: do not wait until tax season to tell your accountant about a major life or business decision.

Buying property, changing jobs, starting a company, selling a business, changing ownership structures, or making significant financial moves can all create tax implications.

Learning about those decisions months later leaves fewer opportunities to plan.

Ashley wants clients to see their accountant as a year-round advisor rather than someone they visit once a year to prepare a return.

That same proactive thinking applies to retirement and estate planning.

Ashley has seen what happens when business owners reach retirement without having saved outside their companies. Those experiences have made long-term planning an important part of the conversations she has with clients.

Wills, beneficiaries, powers of attorney, healthcare proxies, trusts, retirement accounts, and succession plans can all become important pieces of the larger financial picture.

Ashley emphasizes that these decisions often involve several professionals. Attorneys handle legal structures, accountants consider tax implications, and financial professionals address investment and retirement considerations.

Sometimes serving clients also means recognizing when they need expertise beyond what your own organization provides.

Ashley shares the story of a longtime client whose company rapidly expanded into multiple states. Rather than attempting to handle work outside the firm’s expertise, Ashley recommended that the client transition to a larger accounting firm with specialists who could better support the company’s growing complexity.

She even accompanied the client to the meeting with the new accounting team.

It is a powerful reflection of Ashley’s philosophy: serving a client well does not always mean keeping the client. Sometimes it means helping them find the right next step.

As Sixt Gerhard & Associates CPAs continues evolving, Ashley is becoming increasingly intentional about what the firm does best, who it serves best, and how its people can contribute their individual strengths.

Her journey shows that successful leadership is not simply about knowing the numbers. It is about preparing early, developing people, building trusted relationships, asking difficult questions, and creating a business that can continue to thrive as circumstances change.

For business owners thinking about growth, succession, retirement, or simply what comes next, Ashley’s message is clear: the best time to start planning for the future is long before you need the plan.