Author: Gene Marks

You’ve built up your business over years. Now it’s time to sell. You’ve found a buyer. You’ve negotiated a good price. You close the deal.

And then comes the hard part: paying taxes on your gain.

It could be a big number. But there are a number of ways to potentially defer — or even reduce — this cost.

Here are two strategies that have grown in popularity.

Structured installment sale

Using this approach, you don’t take the money up front from the buyer. Instead, a third-party assignment company assumes the buyer’s obligation to make future payments to you.

In many structured installment sales, that obligation is funded by an annuity.

An annuity is an investment vehicle that makes a fixed payment to you over a number of years — even your entire lifetime — in exchange for a lump-sum payment up front, which would be made directly by the buyer of your company. These are usually sold by insurance companies or other large financial services firms.

People like annuities because they protect their principal and offer longer-term financial security. Because many fixed annuities offer a guaranteed payment that covers your expenses, they can also potentially minimize the risk of you outliving your savings.

A structured installment sale defers the capital gains tax on the sale of your company into the future because you only owe the tax in the year when you receive your annuity payment. Interest earned on the annuity is taxed at your ordinary rate as you receive the payment. If your total income declines in the future, this tax could decrease.

“A lot of owners have put everything they had into building the business,” said Wade Martin, a financial adviser with RBC Wealth Management in Princeton. “They don’t have a pension, they haven’t focused on their own financial planning, and they don’t want to take stock market risk. For someone like that, a fixed monthly payment can let them sleep at night.”

There are downsides to annuities.

You lose control over your investment decisions and forego potentially higher gains if you had invested the money on your own. Each installment payment may include a return of basis (part of the money originally put in), capital gain taxed at capital gains rates, and an interest component taxed as ordinary income. Depending on your circumstances, that interest income — or the tax treatment of any remaining annuity value inherited by your beneficiaries — could result in a higher overall tax bill than taking the proceeds up front. You’ll incur fees and you’d likely be susceptible to surrender charges if you withdraw your money early.

“You could theoretically invest the money elsewhere and earn a better return than the annuity’s guaranteed rate,” said Bejan Shirvani, head of structured settlements at MetLife. “However, a good annuity can offer guaranteed payments and professional management.”

Dianne Stewart sold her New Jersey-based auto repair business, Kingston Garage, in 2024. At first she was dubious about a structured installment sale. But then she saw the benefits.

“I asked myself: Do you really need all the cash up front? What are you going to do with it?” she said. “I soon realized that it would be stupid to sell the business outright and lose about 30% to taxes, so for me it’s like a tax-deferred pension.”

But this arrangement may not be for everyone, Stewart acknowledges.

“If you need the money to buy another business or make another investment, it may not fit,” she said. “But if you’re retiring, I think it’s geared toward people who want income instead of one big check, and who want to spread out their tax bill over a longer period of time.”

Donor-advised funds (DAFs)

Setting up donor-advised funds with a wealth adviser allows you to make charitable contributions each year, and then take a tax deduction (subject to some limitations) without actually giving the money away immediately. The fund grows tax-free and you can decide in the future where you want the savings to go. It’s a great way to take advantage of the charitable deduction without committing to a specific charity.

DAFs can also be used to reduce your taxes when you sell your business. The trick here is to make sure your DAF owns a minority shareholder interest in your company before the sale. That way when you sell the company, cash goes to the DAF based on its ownership percentage without generally incurring capital gains taxes because it is a charitable organization.

“A donor-advised fund gives you an immediate tax deduction, tax-free growth inside the account, and the flexibility to decide later which charities will ultimately receive the money,” said Jesse Wideman, a financial adviser with Zenith Wealth Partners in Philadelphia. “Many of my clients have unusually high-income years, often because they’re selling a business. A donor-advised fund lets them capture the charitable deduction in that high-tax year while distributing the money to charities over many years.”

If a business owner is charitably inclined a DAF should be seriously considered, Wideman says, but it’s also important to make sure it’s part of your overall financial plan.

Martin noted that any of these approaches requires thought and long-term planning.

“It’s a holistic viewpoint,” Martin said. “you have to look at estate planning, income taxes, risk tolerance, and what helps someone sleep at night. It’s important to bring in your accountant, attorney, and financial adviser together before making a decision.”

Wars. Inflation. Tariffs. Labor shortages. High interest rates. Political uncertainty. If you only read the headlines, you’d think America’s small businesses are on life support. They’re not.

The sentiment I’ve been hearing and seeing from dozens of industry groups and clients about this year is “so far, so good.” This comes from businesses that do everything from distributing industrial equipment to installing commercial doors. With few exceptions, most have not only been holding their own in 2026, but they’ve been growing.

Anecdotal? Hardly. The data supports these claims.

Manufacturing in the U.S. has expanded for the past five months, reaching its highest level since 2022, according to the closely watched Purchasing Managers Index from the Institute for Supply Management. Service industry companies, according to a similar index, have seen expansion since 2024.

In June, small-business revenue increased in 11 of 12 sectors and in all eight U.S. regions, according to a small-business index published monthly and based on real-life data from hundreds of thousands of customers using Intuit QuickBooks. Payment processing firm Fiserv found that small-business sales showed steady short-term expansion in June, with both nominal sales and transaction volume increasing. Last quarter’s national GDP was just revised from 1.6% to 2.1%.

The U.S. Census Bureau reported that new business applications continue to come in at all-time highs. Even LinkedIn said that there’s been a 69% year-over-year increase in the number of U.S. members adding founder to their profile.

Want more proof?

Despite lower levels of optimism, over half of Main Street owners rated the health of their business as “excellent or good,” the National Federation of Independent Business reported this month. A recent survey from financing firm OnDeck said 93% of small businesses expect growth in 2026, and marketing firm Vistaprint said this month that 84% of small-business owners report being happy operating their businesses, despite ongoing economic and operational challenges.

Bank of America’s June 2026 Small Business Checkpoint said the small-business sector remains “financially healthy and operationally resilient.” MetLife and the U.S. Chamber of Commerce found strong confidence in business health, cash flow, and future growth prospects despite ongoing concerns about inflation, labor costs, and economic uncertainty.

Three out of four U.S. small-business owners expressed “high confidence” in their business’ future, according to new research from Capital One. TD Bank’s recent survey said that small-business owners also remained highly optimistic about future growth.

Economist Mark Zandi recently wrote that among the 25 largest metropolitan areas in the country with populations of more than 3 million, Philly enjoyed the strongest job growth last year. Payroll firm ADP reported that the private businesses in the U.S. added 122,000 jobs in May and 98,000 in June. HR giant Paychex said small-business hiring increased over the past four months.

Job openings among small businesses are rising, an indicator of demand for employees.

“Main Street job openings in New Jersey and nationwide are starting to pick up after a decline in May,” National Federation of Independent Business New Jersey state director Eileen Kean told ROI-NJ.

Center City, which represents 42% of all Philadelphia employment, has seen office leasing activity reach its highest level in six years, according to Center City District’s State of Center City 2026 report. The report also highlighted development projects topping $2 billion; projected Convention Center attendance exceeding 1 million in 2026; and retail, restaurants, and cultural institutions that “continue to rebound strongly.”

There are always news reports about how this business is “struggling” and that business is “barely holding on.” There’s no denying that this happens. How could it not? There are more than 34 million small businesses in the United States operating in hundreds of different industries and localities. Some are bound to be doing better than others.

But other things happening right now are underscoring small-business growth and optimism.

Tariffs (that aren’t being refunded) may have increased costs for some, but many manufacturers are reporting increased domestic demand as global firms move more operations here.

Inflation is sticky, but at less than 3% excluding energy, most business owners have found ways to pass these costs down to their customers or find other savings internally.

Labor shortages persist but most company owners are getting their work done regardless.

And consumer spending is strong, according to recent data from the National Retail Federation.

Oil prices are now back down to prewar levels.

Many owners are also benefiting from a lighter federal regulatory environment and friendlier tax policies. Capital is more expensive than in years past, but available for those who can measure return on investment. The stock market is up over 20% over the past year, providing more financial security. And for entrepreneurs and small-business owners, government aid and other resources, education, tools, and support proliferate like never before.

Small businesses employ half of the country’s workers and make up half of our GDP. Their success is critical for the U.S. economy.

They aren’t ignoring the challenges. They’re simply finding ways around them. And that’s why, despite all the doom and gloom, many are having a surprisingly good year.

When it comes to office software, people generally think first of Microsoft. But the reality is that Google Workspace is used by over 11 million paying organizations and boasts more than 3 billion monthly active users globally.

Many of my small-business clients use Google Workspace to send emails, create documents and spreadsheets, host meetings, and store files. And yet most are only scratching the surface. It’s often frustrating to witness so many businesses not taking advantage of all the capabilities of Google Workspace, even though they’re paying for it. That’s a waste of money.

If used the right way, Google Workspace can scale right along with the growth of your business, provide excellent collaboration features, and can be cost-effectively managed and secured without requiring expensive IT firms.

For starters, centralize everything.

If you’re going to use an office platform like Google Workspace, it’s best to lean into it fully. Mollie Plotkin, who runs a successful talent and speaker agency in Philadelphia, says Google Workspace is the “shared backbone” of her company. She uses Google Meet, Calendar, Chat, and Drive to “create an ecosystem” so that everything is in one place.

“Work is much more manageable when everyone had equal access to the same systems regardless of where they were working,” she said. “Instead of relying on multiple versions of files being e-mailed around, our teams work from one live document at a time, which dramatically reduces confusion and duplication.”

Plotkin also says that her internal team saves time on searching and improves efficiencies by consolidating all files and data in one place.

“Important information lives in shared spaces instead of individual inboxes, which makes collaboration faster and prevents bottlenecks,” she said. “We use shared templates, collaborative planning documents, and centralized project tracking so our team can move quickly without reinventing processes each time.”

Cheryl Friedenberg, a founder of High Key Impact, a digital marketing firm in Blue Bell, says that sharing calendars has significantly reduced “all the back and forth” for scheduling client calls and managing deadlines.

“Google Drive and Docs make sharing files simple, without endless email chains,” she said. “There’s no confusion about versions or missing attachments.”

Friedenberg always tells her clients to go the extra yard and make sure to also use Gmail within their own website domain and not as just a Gmail address.

“Using a generic @gmail.com address on proposals, invoices, or your website can make your business look less professional,” she said.

Automate everywhere

Once your team is using Google Workspace as a primary office management tool, it’s important to start automating tasks wherever possible.

Milan Baria, who runs Blueclone Networks, an IT services firm in Princeton, says that with Google Workspace you don’t need a developer to automate repetitive tasks. “We use simple scripts to bridge the gap between Google Sheets and Gmail to automate client follow-ups.”

Andy Williamson, one of the founders of Wilmington-based training firm ONLC, says that Google Workspace Studio, with Apps Script, lets a non-technical user describe a workflow in plain English and have it built.

“The new agents can read the email that came in, decide what kind of request it is, draft the reply, pull the right doc, and only come back to you when something actually needs a person,” he said.

Williamson says that it’s not difficult to create automation so that a company’s data power dashboards or other applications.

“Apps Script used to be just for programmers, but this has been changing recently,” he said. “Everyone in the business is becoming an agent builder, not just the developers.”

Leverage AI

Even if you’re not ready to automate with agents, Google Workspace comes with many AI features right out of the box.

Friedenberg says that by leveraging AI, a user can turn a simple prompt into a fully designed presentation in minutes.

“You’re starting with something polished instead of a blank page,” she said.

In addition, and instead of hiring a videographer, Friedenberg encourages her clients to use Google Workspace to make short professional-looking video.

“You can make a spokesperson-style video without being on camera,” she said. “The voice-overs sound natural enough that most viewers wouldn’t know they were AI-generated. Many small-business owners don’t realize it’s already included in a tool they’re probably already paying for.”

Joe Henderson, a Philadelphia-based expert with Google premier partner Promevo, says that another underused application is Google’s Notebook LM, a premium feature with many paid Google Workspace plans.

“Notebook LM is an AI research assistant that analyzes your documents, then generates summaries, answers questions, creates study guides, timelines, podcasts, and other content based solely on your uploaded sources,” he said. “Our clients use it to input raw documents, industry articles, vendor videos, and automatically turn that chaotic information into easy-to-understand explainer videos, short audio podcasts, quizzes, and custom study guides. It’s like a proactive operational brain sitting within Google Workspace.”

Finally, lean into Workspace’s IT management tools

Baria says that most owners don’t realize that they easily can restrict Workspace access based on the user’s location or device security status like any experienced IT professional.

“High-level security isn’t just for enterprises,” he said. “Small businesses can set up simple rules that prevent employees from accidentally emailing out sensitive information, and use Workspace’s license and user management tools to eliminate unnecessary applications and archive user accounts to save hundreds, even thousands, of dollars a year.”

Plotkin agrees.

“You don’t need a massive IT department or expensive infrastructure,” she said. “Workspace allowed us to add team members, improve collaboration, and manage more clients without drastically changing our operational structure.”

A client of mine had a check they mailed stolen before it reached their supplier. The check was altered for a different payee and amount and then cashed. Another client said someone got a copy of one of his company’s checks and created counterfeit versions using AI.

Countless clients have reported unauthorized electronic check requests made to their bank accounts, with more than a few finding out after their money had disappeared.

Check fraud is real, and it’s bad.

“Check fraud remains a major threat, and businesses are becoming much more aware of it,” said Janet Miller, senior vice president at Fulton Bank in Philadelphia. “Fraud has become so prevalent. Five years ago I’d have conversations about fraud protection with my clients, and there was a resistance to it. But now it’s like, yes, we need to protect ourselves!”

A 2025 study from the Association for Financial Professionals found that 79% of organizations experienced attempted or actual payments fraud in the past year, with 63% representing attempted or actual check fraud.

Checks, which the study says are still used by 91% of businesses, remain the single most-targeted payment method, but, according to the study, wire transfer fraud was reported by 63% of respondents, up from 39% in the previous survey, and ACH (Automated Clearing House) credits fraud was reported by 50%.

“Fraud is something that only expands,” said Tom Gregory, head of Treasury Management, Merchant and Government Banking at TD Bank. “New technologies like AI and spoofing, key logging, and social engineering are always creating new ways of perpetrating crime.”

Ask any accountant, and we’ll say that there are certainly internal controls that should be implemented at your company to help reduce the risk of check fraud. These would include multilevel approvals, better security over physical checks, segregation of duties among financial people, mandated vacations, and cross training.

But one of the best defenses growing in popularity is called Positive Pay, a banking service that helps prevent check and payment fraud. I’ve been urging all of my clients to subscribe to this service, which is offered by most banks.

Melissa Jetland, a senior vice president at Fulton Bank, says Positive Pay is a powerful risk management tool for your company’s cash.

“Think of it as the simplest way to put a gate in front of your money,” she said.

Positive Pay works in two ways. For regular paper check payments, your company electronically sends your bank a list of the checks (which includes payee, purpose, amount, date), and the bank then matches that list against the actual check payment request made by the payee. If the payment request doesn’t exactly match all the data on the list, it gets rejected.

Positive Pay also works with ACH payments. In this manner you tell the bank which vendors are allowed to make debits to your account. Any request that doesn’t have an authorized vendor will be rejected.

“If you don’t do that, the bank is obligated to post every debit that comes because in an ACH system, the originating bank warrants their validity — even if the payment hasn’t been authorized by you,” Gregory said.

Why wouldn’t most small businesses sign up for Positive Pay? According to recent market research of U.S. financial institutions, only 29% of banks and credit unions are satisfied with their current Positive Pay adoption rates. Other industry reports estimate that only about 35% of eligible business customers currently use the service, despite the recent surge in check fraud.

Yes, there is an additional cost (generally $25 to $100 per month for basic Check Positive Pay), but Fulton’s Jetland believes one of the biggest barriers isn’t cost. It’s the belief that Positive Pay is cumbersome.

“It really is lack of education,” she said. “Some owners worry that uploading check files and reviewing exceptions will be difficult and time consuming, but that’s usually not the case.”

According to research by a financial technology provider, more than 75% of banks expect Check Positive Pay adoption to increase over the next two years.

It’s effective. One study from last year by a fraud prevention services company found that 77% of users with Positive Pay reported fewer check fraud attempts or losses.

Subscribing to Positive Pay doesn’t completely protect you from fraud. Gregory says that things like daily account monitoring, setting up check and ACH blocking on your bank accounts that are never used for disbursing money is also important.

“Understand that fraud prevention requires multiple layers of defense,” he said. “There’s really no 100% ironclad fail-safe system. But layers of control and being mindful will reduce your risk.”

As an accountant, I’ve learned that fraud prevention isn’t about finding one perfect solution. It’s about building layers of protection. Positive Pay may not stop every criminal, but it has become one of the easiest and least expensive layers a small business can add.

Miller says that Positive Pay is a good insurance policy for every company’s cash.

“It’s a very manageable cost and the protection it provides is worth it,” she said.