Earmark CPE

Earn CPE Anytime, Anywhere

Small Business

When Good S Elections Go Bad and How to End Them Properly

· ·

When businesses elect S corporation status, they often focus on the self-employment tax savings. But what happens when that election no longer makes sense—or worse, when it accidentally terminates? In episode 14 of Tax in Action, tax expert Jeremy Wells, EA, CPA, explores the complex process of ending S corporation elections, based on his firm’s recent experience with businesses struggling in the post-pandemic economy.

“A lot of small businesses that started up during the COVID-19 pandemic have seen business taper off quite a bit in the last year or two,” Wells explains. “Businesses that a few years ago actually made sense to be S corporations, nowadays not so much. And the owners want to stay in business, they want to keep operating, but it can be pretty burdensome to run an S corporation when profit margins aren’t what they were.”

Three Ways Your S Election Can End

Under IRC Section 1362, an S election remains in effect until termination, which can occur in three ways. Wells breaks down each path and the triggers that set them off.

1. Revocation by Choice

The most straightforward way to end an S election is to revoke it voluntarily. “An S corporation can revoke the S election for any taxable year,” Wells notes, “including the first year.”

The process requires shareholders owning at least half of the corporation’s shares (including non-voting shares) to consent in writing. Each consenting shareholder must provide their name, address, tax ID, number of shares owned, the date they acquired the stock, the date their tax year ends, and the corporation’s name and tax ID.

Timing matters. As Wells explains, “The corporation files that revocation statement by the 15th day of the third month of the taxable year. In general, if you’re working with a calendar year S corporation, that’s March 15th.” File after that date, and the revocation takes effect the following tax year.

This creates planning opportunities. “We’ll usually plan to go ahead and close out that calendar year as an S corporation,” Wells says when dealing with mid-year decisions. “But we’ll go ahead and get the paperwork ready and send in that revocation statement and make it effective as of the beginning of the following year.”

Corporations can also file prospective revocations for future dates and even rescind them if circumstances change. However, there’s a catch: if new shareholders join after the revocation is filed, they must also consent to any rescission.

2. Failing to Qualify

The second termination path occurs automatically when a corporation ceases to meet S corporation requirements. Wells emphasizes that “those qualifications have to be met continuously. It’s not just meeting those qualifications, electing S, and then not worrying about it anymore.”

Common disqualifying events include:

  • Exceeding 100 shareholders
  • Adding a nonresident alien shareholder
  • Having a shareholder that isn’t an individual (with limited exceptions for estates, trusts, and tax-exempt organizations)
  • Creating multiple classes of stock

The stock class issue causes particular confusion. “Voting versus non-voting stock does not create a second class,” Wells clarifies. “You can have voting and non-voting stock in an S corporation.” The problem arises when shares have different rights to distributions or liquidation proceeds.

“In an S corporation, every share of the corporation stock has to confer identical rights to distributions and liquidation proceeds to every other share of stock,” Wells explains. “So if I own 10% of the stock, I get 10% of the distribution. If somebody else owns 20% of the stock, they get 20% of the distributions.”

This is especially important for LLCs electing S status. “If you’re working with an LLC that’s considering electing S, it’s incredibly important to get a copy of the operating agreement, review it, and make sure there are no preferential rights, no waterfall distribution schedules,” Wells warns.

3. Excessive Passive Investment Income

The third termination trigger only affects S corporations with C corporation history. If a corporation has C corporation earnings and profits and generates passive investment income exceeding 25% of gross receipts for three consecutive years, the election terminates.

“Congress intended to make S Corporation provisions available only for businesses that are engaged in active operations of businesses, not those that are mainly involved in passive investment activities,” Wells explains.

The rules here get complex. Passive income includes dividends, interest, rents, royalties, and annuities not earned in the ordinary course of business. However, Wells notes important exceptions. For example, rent from a business actively managing properties doesn’t count as passive if the corporation “performs significant services or incurs substantial costs in the rental business.”

Since many modern S corporations started as LLCs and never operated as C corporations, this rule often doesn’t apply. Wells shares a close call from his practice: “The individual thought he needed to put his individual stock holdings into an LLC and then, for some reason, thought he needed to elect S for that LLC.” The only thing that saved this client was that the LLC had no C corporation earnings and profits.

The Hidden Withdrawal Option

Perhaps the most valuable tool Wells reveals is the withdrawal provision, found in Internal Revenue Manual 3.13.2.27.10.

“If the IRS accepts the withdrawal request, then the entity is treated as if the classification had never been elected,” Wells explains. This option is available only before filing the first S corporation tax return—March 15th for calendar-year corporations.

The withdrawal can be requested through correspondence or by filing Form 8832. Wells has used this for clients who received bad online advice. “We’ve done this before with small businesses that hadn’t even really gotten started yet. The taxpayer got some bad advice online and thought an S corporation starting off was the way to go.”

The advantage is that, unlike revocation, withdrawal doesn’t trigger the five-year waiting period before re-electing S status. “That corporation could elect S, withdraw its election, and then the next year decide to elect S again. And there’s no problem with that,” Wells notes.

When State and Federal Rules Diverge

State administrative dissolutions can come as a surprise to business owners. Many panic when they forget to renew their state LLC registration, but Wells offers reassurance based on multiple IRS Private Letter Rulings.

“The IRS still considers the S corporation in existence. So a state law administrative dissolution of an LLC does not translate into a termination of the S election,” he explains. “As long as the business continues operating and continues fulfilling its tax filing requirements, the IRS doesn’t appear to really care about what happens at the state level.”

There’s no need for a new S election when the entity gets reinstated at the state level. “Just keep operating as if everything is fine, at least at the federal level, and try to get that corporation or LLC reinstated at the state level,” Wells advises.

Critical Documentation and Next Steps

Wells emphasizes the importance of maintaining proper records. Keep the original Form 2553 and the IRS acceptance letter, as you’ll need to know which service center processed the election if you later want to revoke it.

Processing delays have become a challenge. “I’ve seen it take anywhere from six to 18 months for that S election to get processed,” Wells notes, partly because Form 2553 still requires wet-ink signatures and must be paper filed.

This episode is part one of a two-part series. Wells promises to cover the implications of termination, including the five-year rule and handling split years when termination occurs mid-year, in the next episode.

For tax professionals dealing with struggling businesses or succession planning complications, understanding these termination options preserves flexibility for clients whose circumstances change. As Wells demonstrates through his firm’s experience, what made perfect sense during the pandemic boom might need reconsideration today.

Ready to dive deeper into S corporation terminations and their implications? Listen to the full episode of Tax in Action for Wells’ complete analysis and practical guidance for navigating these complex scenarios.

How Smart Small Businesses Turn Economic Headwinds into Competitive Advantages

· ·

Small businesses are navigating a unique economic moment in 2025. They’re still serving customers and meeting market demands, but they’re doing it while managing changing costs and ongoing policy uncertainty. Despite these challenges, they’re not shutting down or laying people off. Instead, they’re finding creative ways to adapt.

Nicholas Tremper, senior economist at Gusto, shared this insight in a recent Earmark Podcast episode. Tremper tracks data from hundreds of thousands of small businesses through Gusto’s platform, so he has a unique view into how small businesses respond to today’s economic challenges.

The picture Tremper paints is more complex than the headlines suggest. While businesses face real pressures from tariffs, labor shortages, and economic uncertainty, many thrive by combining two essential strategies: utilizing AI to boost productivity and offering more appealing benefits to attract workers. For accounting professionals, this creates new opportunities to become strategic advisors rather than just compliance providers.

Economic Headwinds Create Planning Challenges

In the current economic environment, several interconnected challenges reshape how small businesses operate. Tariffs have reached a weighted average of about 18% across all imports—a significant jump from single digits in previous years. While this level is manageable for most businesses, the bigger problem is uncertainty.

“Small businesses don’t necessarily know how to think about what their costs will be three or six months from now,” Tremper explains. This uncertainty affects everything from inventory planning to contract bidding. For example, if you’re a retailer trying to stock up for the holidays or a contractor giving price estimates months in advance, not knowing future costs makes planning nearly impossible.

The labor market adds another layer of complexity. Unemployment sits at a relatively low 4.3%, but the July jobs report showed weakness with only 73,000 jobs added versus 100,000 expected. More concerning was the massive downward revision of 258,000 jobs from previous estimates for May and June. (Updated numbers released after the show was recorded are +22,000 jobs for August.)

This reflects what Tremper calls an economy that’s “idling”—staying in place rather than growing or contracting. Businesses aren’t laying people off, but they’re not hiring aggressively either. The combination of an aging population and tighter immigration policies creates structural labor shortages, especially in construction and hospitality sectors that traditionally relied on both groups.

These pressures force businesses to delay growth plans. As Tremper puts it, “You may not be able to work on that fourth development. You may have to stop at the three.” When you can’t reliably access more labor, expansion is much more complicated.

Entrepreneurship Boom Continues Despite Challenges

Despite these headwinds, there’s been an entrepreneurship renaissance in the United States. The number of new business applications skyrocketed during the summer of 2020, and as of June 2025, new businesses were still 57% higher than June 2019 levels.

The resilience of small business formation helps explain why the economy has remained relatively stable. “One of the reasons that the economy has been so resilient is because these new businesses have been bringing creative ideas to market,” Tremper notes.

What’s particularly interesting is who’s starting these businesses. For the first time, almost half of new businesses were started by women, compared to 30% in 2019. There’s also been an increase in businesses started by nonwhite entrepreneurs, showing entrepreneurship is spreading across demographics.

These new business owners face similar challenges regardless of their background. When asked about their top three challenges, they consistently mention cash flow, time management, and acquiring customers and employees. At least two of these are areas where accountants can provide significant value.

AI Boosts Productivity Without Replacing Workers

Here’s a statistic that might surprise you: 95% of small businesses using AI aren’t cutting their workforce. Instead, they’re making their existing employees more productive. This contradicts the common narrative that AI inevitably leads to job losses.

The productivity gains are substantial. According to Gusto’s research, 80% of small businesses using AI report productivity increases of 20% or more. But the key insight isn’t just that AI works; it’s how it works.

“Rather than an AI doing somebody’s job, what the person’s doing is they’re like, I’m the expert and you’re going to be a teammate to help me accomplish this quickly,” Tremper explains.

Businesses use AI for routine tasks like summarizing information and conducting market research—the necessary work that doesn’t require deep expertise. Meanwhile, humans focus on applying their knowledge, making judgment calls, and building client relationships.

This approach creates an unexpected benefit in hiring. Businesses that allow employees to use AI report 45% less difficulty finding new workers. It turns out people want to work for companies that give them tools to focus on meaningful work instead of tedious tasks.

The most successful AI implementations happen when businesses develop clear plans about when to use human expertise versus when to leverage AI for efficiency. This strategic approach creates a cycle where better tools lead to more satisfied employees, which makes companies more attractive to potential hires.

Benefits Become Essential for Talent Competition

While AI tackles productivity, smart businesses simultaneously invest in benefits to attract and retain workers. In today’s tight labor market, benefits are competitive necessities.

Offering healthcare benefits increases employee retention by 40% in the first year. Retirement plans show similar effects. What’s interesting is that half of the businesses offering retirement benefits don’t do any company matching. They get significant retention benefits just by offering the benefit.

This creates opportunities for businesses willing to think strategically about their total compensation packages. While competitors focus solely on wages—an expensive and difficult race to win—smart businesses create comprehensive value propositions that extend beyond the paycheck.

For accountants, a communication gap represents a missed opportunity. Fifty percent of small businesses don’t know if their accountant offers benefits guidance, and two-thirds of those simply never thought to ask. When small businesses receive benefits guidance from their accountants, 60% say it influences their benefit decisions. For businesses under two years old, that number jumps to 85%.

Accountants as Strategic Partners

This economic environment creates new opportunities for accounting professionals to evolve beyond traditional compliance work. The share of businesses reporting productivity gains from their accountants has jumped dramatically—from 52% in 2021 to two-thirds in 2025.

“Small businesses view their accountants as business partners. These aren’t number crunchers. These are people who are actively helping me figure out what I’m going to do next,” Tremper explains.

Businesses navigating today’s challenges need more than bookkeeping and tax prep. They need guidance on cash flow analysis, scenario planning, and strategic decision-making. When small businesses can’t predict their costs or easily access more labor, having an advisor who can help them model different scenarios is invaluable.

Cash flow, time management, and hiring are all areas where accountants can provide significant value. Whether it’s helping a client switch to upfront billing to improve cash flow or advising on benefits strategies to attract workers, these services directly address the problems keeping business owners up at night.

Interest rates remaining higher than business owners would like make this financial guidance even more critical. As Tremper notes, “It’s so important to really understand the return on investment on those borrowing costs.” Businesses need help evaluating whether investments will generate enough return to justify higher borrowing costs.

Cautious Optimism for Small Business Future

Despite the challenges, Tremper remains optimistic about small businesses’ prospects based on their track record of resilience. Over the past five years, small businesses have navigated a pandemic, an inflation crisis with rates hitting 8-9%, a major labor market reshuffling, and now uncertain tariff policies. Through it all, more people keep choosing to start businesses.

“They’ve got this grit, this creativity,” Tremper observes. “These things make me most optimistic about small businesses.”

The economic fundamentals, while softening, aren’t collapsing. Consumer spending continues to increase, albeit more slowly. People are choosier about purchases, but demand hasn’t fallen off a cliff. This provides a foundation for businesses that can adapt to changing conditions.

The businesses succeeding in this environment understand that sustainable competitive advantage comes from combining cutting-edge tools with meaningful employee value propositions. They’re not choosing between technology and people; they’re investing in both simultaneously and strategically to create resilience against future uncertainty. By maximizing productivity per employee and creating strong retention through benefits and culture, these businesses position themselves to weather whatever economic storms may come.

For accounting professionals, this transformation represents a challenge and an opportunity. Clients need more strategic guidance than ever, and they’re willing to pay for and value that guidance in ways they haven’t before. The firms that master this new approach can build sustainable competitive advantages that compound over time.

Listen to the full conversation with Nich Tremper to discover specific strategies for advising your clients through this period of transformation and learn how to position your practice as an indispensable strategic partner in their success.

Proactive Cash Flow Solutions for Small Business Clients

· ·

Millions of small business owners start every morning the same way—logging into their bank account to see their balance. While 95% of business owners perform this daily check, a recent Cash Flow Compass report from Relay reveals a startling insight: 91% of small businesses face ongoing cash flow challenges. Despite their vigilance, most owners still lack the structures and systems to plan effectively, leaving them vulnerable to late payments, insufficient reserves, and high stress.

Based on a recent webinar featuring Blake Oliver, CPA, and Relay’s own Deanna Zubrickas, this article explores how accountants and financial advisors can move beyond balance-check advising and guide clients toward proactive, data-driven cash flow strategies. By leveraging multiple bank accounts, automated transfers, and regular check-ins, accountants can deliver both financial clarity and much-needed peace of mind to overworked owners.

Let’s dive into some of the key points from the webinar and, more importantly, what you can learn from them. 

1. The Universal Challenge: 91% Face Cash Flow Struggles

In Relay’s Cash Flow Compass survey of over 750 small businesses:

  • 91% of respondents reported dealing with cash flow issues.
  • Common causes include rising labor costs, seasonal fluctuations, and late client payments.

With so many business owners feeling the pinch, accountants have an opportunity to provide high-value advisory services that go far beyond routine compliance work.

2. Overconfidence vs. Reality: The 42% Confidence Gap

One surprising finding is that many owners believe they have a solid handle on their finances—but the numbers tell a different story. On average, business owners are 42% more confident in their cash flow management than is justified by their actual data. This gap creates real risks. 

Blake remarks, “Coming off of a busy season, business owners see a big bank balance and feel invincible. The challenge is helping them realize that money might need to stretch through slower months or seasonal dips.”

This mismatch between perception and reality underscores the need for deliberate systems that track not just daily balances but future obligations.

3. Missing Payments, Personal Stress, and Burnout

Cash flow struggles affect both the business and its people:

  • 31% of respondents missed or were late on major payments, including rent and payroll.
  • 71% reported experiencing significant stress or anxiety due to cash flow woes.
  • 62% said they suffered negative outcomes like delayed projects or losing clients.

For many, delayed payments jeopardize vital relationships with landlords, suppliers, and staff. Even worse, it erodes personal well-being. As Blake noted in the webinar, accountants are uniquely positioned to help clients break this cycle, offering regular check-ins and proactive planning that reduce the risk of crisis—and the accompanying burnout.

4. The Single-Account Trap: Why 24% Use Multiple Accounts

Despite recognizing their vulnerabilities, most small businesses still rely on one operating account for everything. According to the survey:

  • 95% check their balance daily,
  • but only 24% maintain multiple accounts to track and separate funds.

Without additional accounts, it’s easy to mix up funds earmarked for payroll, taxes, or profit distributions. That single lump-sum balance can create a false sense of security. This is where modern tools and advisory play a crucial role.

5. Structuring for Success: Multiple Accounts and Automated Transfers

Relay, the official banking partner of Profit First, offers a clear solution:

  1. Create Multiple Accounts: At a minimum, split finances into an operating account, payroll account, and savings or tax account.
  2. Automate Transfers: Relay lets you set rules so each payment received is split into designated buckets—e.g., 10% for taxes, 15% for profit, and the rest for operations.
  3. Project-Based Accounts: For agencies or firms handling multiple projects, separate accounts for each project can clarify available budgets without waiting for monthly reconciliations.
  4. Receipt Capture & Sync: Relay’s new receipt capture feature (in beta) automatically syncs to QuickBooks or Xero, streamlining bookkeeping and reducing administrative overhead.

By making these processes nearly automatic, business owners start building reserves without having to remember monthly or quarterly transfers. Even small percentage allocations can add up, bolstering that emergency fund. Meanwhile, accountants can monitor activity in real-time rather than sifting through backlogged statements.

6. Advisory in Action: Weekly 15-Minute Check-Ins

A critical element of success is consistent communication. Rather than waiting for quarterly reviews—or worse, an emergency—weekly 15-minute video calls can transform client relationships:

  • Forecast: Quickly update spreadsheets or dashboards, listing upcoming bills, expected deposits, and payroll cycles.
  • Allocate: Ensure auto-transfers are working as intended and address any shortfalls immediately.
  • Plan: Discuss hiring decisions or new projects that might affect cash flow in coming weeks.

This shift from reactive to proactive engagement positions accountants as strategic partners. As clients see their cash flow stabilize, trust builds, and deeper advisory conversations become routine.

7. The Bigger Picture: Reducing Stress and Enabling Growth

When small businesses move beyond bank-balance management, they gain more than just better books—they reduce anxiety, avoid late fees, and seize growth opportunities. With 43% of surveyed businesses having less than a month of reserves, even moderate savings can soften sudden revenue dips or unexpected expenses.

Most importantly, owners get back to focusing on what they do best—running and growing their companies—rather than obsessing over daily balances. It’s a win-win for both the client and the accountant.

Conclusion: Empower Your Clients to Thrive

For many entrepreneurs, the line between personal and business stress is razor-thin. By advocating structured cash flow management—multiple accounts, automated transfers, and regular advisory sessions—accountants can deliver peace of mind while ensuring clients have the resources to grow sustainably.

Ready to see these strategies in action? Watch the full webinar for in-depth conversations, real-world examples, and detailed demonstrations on how to implement a modern cash flow system. Equip your clients to move beyond the daily balance check and lay the groundwork for lasting success.

The Resilient Entrepreneur: Strategies for Embracing Uncertainty in Your Small Business

· ·

In the ever-changing landscape of entrepreneurship, uncertainty is the only constant. As a small business owner, how can you survive and thrive in the face of unpredictable challenges? In a recent episode of “Build to Enough,” host Keila Hill-Trawick dives deep into the strategies and mindsets necessary for navigating uncertainty as a small business owner. From her accountant expertise and experience working with diverse clients, Keila shares invaluable insights on proactive preparation, adaptation, and leveraging external support.

The Importance of Proactive Financial Preparation

Small businesses face a myriad of uncertainties, each with its unique challenges. As Keila points out, “When we’re talking about uncertainty for small businesses, it can mean a variety of things, from economic downturns or changes in the economy that affect both you as a small business owner or your particular industry, to market volatility and other external factors like local changes or a pandemic.” Recognizing and anticipating these various types of uncertainty is the first step in developing a resilient business strategy.

One critical component of navigating uncertainty is proactive financial preparation. Keila emphasizes the importance of maintaining a 3-6 month expense cushion and accurate bookkeeping. “You want to make sure that you have a savings account that will cover you when and if there are any changes to your business income.” By taking these proactive measures, small business owners can create a financial safety net that allows them to weather unexpected challenges and maintain stability during times of uncertainty.

Strategic Adaptation: Staying Agile in the Face of Change

In addition to financial preparation, strategic adaptation is critical to building resilience as a small business owner. Keila stresses the importance of periodically reassessing services, target clients, and pricing to ensure value provision and adaptability:

“When we get into business, it can be easy to think we can set it and forget it… But the landscape is constantly changing,” Keila advises. “The ideas about what is good, right, and valuable for the people we serve are constantly in flux, and we can’t always keep up with all those changes. But what we can do is make a commitment to say at various points throughout the year, ‘I will check in and make sure that one, what I’m doing is what I want to be doing; two, that I’m serving the right clients within those services; and three, that I am pricing myself in a way that reflects the value that I am providing.’”

Keila shares an example of clients in the diversity and inclusion training industry who had to pivot when corporate priorities shifted. She explains that when D&I was a booming area, many of her clients in that industry were making significant profits. Corporations were investing in D&I initiatives and hiring trainers at competitive rates to come in and work with their companies.

However, this trend did not continue indefinitely. Keila notes that, perhaps unsurprisingly, many companies eventually slashed their D&I budgets or decided it was no longer a top priority. As a result, D&I trainers who had previously been thriving in this space would have lost money if they had not adapted their strategies.

This example highlights the importance of strategic adaptation in the face of changing market conditions and client priorities. It demonstrates how small businesses and entrepreneurs must remain agile and responsive to shifts in demand, even in areas that were once highly profitable. Small business owners can increase their resilience and ability to navigate uncertainty in their respective industries by being prepared to pivot their offerings or target new markets when necessary.

Leveraging External Support and Expertise

Navigating uncertainty doesn’t have to be a solo journey. Keila emphasizes seeking guidance from industry professionals, peers, and mentors when facing unpredictable challenges. She says, “Finding experts that know more than you, or just have access to resources that you might not have access to, is really a good way to prepare yourself against those uncertain times that are going to show up for you.”

Moreover, being part of a supportive community where members can offer mutual support during challenging times can be invaluable. Small business owners can gain new perspectives, insights, and strategies for navigating uncertainty by tapping into collective wisdom and resources.

Embracing Uncertainty as a Natural Part of Business

Ultimately, uncertainty is an inevitable part of the entrepreneurial journey. As Keila reminds us, “At the end of the day, uncertainty is a natural part of business. None of us know what’s going to happen, and our best-laid plans go to crap all the time because you just don’t know what’s going to happen around you.” 

Rather than avoiding uncertainty altogether, small business owners must embrace it as a natural part of the process and focus on developing the resilience and adaptability necessary to thrive in the face of change.

Tune in to “Build to Enough” to Learn More

Navigating uncertainty as a small business owner requires a multifaceted approach that includes proactive preparation, strategic adaptation, and leveraging external support. By developing financial stability, staying agile in the face of change, and tapping into the wisdom and resources of a supportive community, entrepreneurs can build the resilience necessary to survive and thrive in unpredictable challenges.

Tune in to this episode of “Build to Enough” to learn more about navigating uncertainty as a small business owner and discover practical strategies for proactive preparation, adaptation, and leveraging external support. With the right mindset and tools, you can build a meaningful and sustainable business that weathers any storm.