Blake Oliver

Tired of the January Scramble? Discover a Proactive Approach to 1099 Compliance

Earmark Team · February 7, 2025 ·

No one brushes their teeth only the day before a dentist appointment and expects a clean bill of health—yet many businesses approach 1099 compliance in exactly this way. Every January, they scramble to collect W-9s, validate tax IDs, and rush out filings before the deadline. This last-minute frenzy creates stress and exposes companies to serious penalties if documentation is missing or incorrect.

In a recent Earmark Expo webinar, Gordon Walsh from Avalara demonstrated how modern automation tools like Avalara 1099 & W-9 can transform 1099 compliance from a reactive, annual challenge into a proactive, year-round process. By embracing real-time TIN matching and automated W-9 collection, businesses can significantly reduce compliance risks while freeing up valuable time during the year’s busiest season.

1099 Compliance Shouldn’t Be an Annual Fire Drill

Federal law requires businesses to collect W-9s before making payments to vendors. Despite this requirement, many firms still rely on manual processes: chasing vendors for handwritten forms, deciphering errors, and hoping everything arrives before January 31st. Without valid taxpayer information, businesses must withhold 24% for backup taxes—a situation that can create significant cash flow issues for vendors and administrative headaches for businesses.

“January’s 1099 season is really just where we feel the pain of all the things that we’ve done year-round that maybe didn’t get done,” explains Gordon Walsh. This reactive approach inevitably leads to costly, last-minute fixes and potential penalties.

The Power of Automated W-9 Collection

Traditional W-9 collection relies heavily on email and PDF exchanges—a system Gordon critiques saying, “There’s no other place in my life and business anywhere where I’m giving handwritten documents to people and expecting to do business with them.”

Modern automation tools solve these challenges through:

Guided electronic forms with built-in validation
Intuitive menus that reduce classification errors
Centralized dashboard for tracking compliance status
Automated classification checks for 1099 requirements
Electronic delivery consent during onboarding

Having a system to collect vendor information ensures the capture of correct legal entity names, preventing downstream mismatches with IRS records.

Real-Time Validation: Preventing Costly Mistakes

Real-time TIN matching serves as the cornerstone of modern compliance systems. Instead of discovering mismatches after filing or receiving notices months later, Avalara’s system validates tax identification numbers during vendor onboarding.

When mismatches occur, vendors can correct issues immediately, preventing:

Notices from the IRS
Mandatory 24% backup withholding
Time-consuming vendor follow-up
Potential penalties and fines

The system returns validation results directly to vendors during the submission process, allowing for immediate corrections. This preventative approach significantly reduces the risk of receiving IRS notices demanding backup withholding or corrections.

Streamlined Year-End Processing

The platform’s dashboard provides clear visibility into compliance status using a stoplight system:

Green: Ready for e-filing and electronic delivery
Yellow: E-filing ready but requires physical mail delivery
Red: Issues requiring immediate attention

For corrections, which are provided at no additional cost, the process has been simplified to a few clicks. Users can edit information directly in the system, with automatic filing of corrected forms to both state and federal authorities.

Integration and Accessibility

The system integrates with major accounting platforms like QuickBooks and includes bulk import capabilities for larger datasets. A global search function enables quick access to historical forms, allowing users to resend documents to recipients within seconds rather than searching through saved PDFs.

Historical data is maintained for five years, and the platform includes:

Secure document-sharing capabilities
State-specific compliance automation
Address verification through USPS
Multiple user access with role-based permissions

Pricing and Implementation

Rather than charging by the number of clients or users, pricing is based on total form volume. This tiered pricing model creates economies of scale—from several dollars per form at lower volumes to cents per form for high-volume users. While physical mailing incurs additional costs, the system encourages electronic delivery through early consent collection, helping businesses reduce expenses and administrative overhead.

The platform’s ease of use has earned it an NPS score of 79, reflecting its intuitive design and comprehensive feature set. With continued development, including a recently tripled development team, the system aims to expand its integration capabilities and streamline data flow between various business systems.

Through this combination of preventative validation, automated collection, and streamlined processing, businesses can transform their 1099 compliance from an annual emergency into a manageable, year-round process.

Watch the full Earmark Expo webinar to see these automation tools in action and learn how to implement a proactive approach to compliance.

Is Your Accounting Firm Drowning in Too Many Software Solutions?

Earmark Team · February 7, 2025 ·

How many browser tabs do you have open just to run your accounting firm? If you’re like most modern practitioners, the answer might be “far too many.” From time tracking to e-signatures, invoicing to document sharing, each separate function tends to live in its own app. This “app fatigue” frustrates staff, drives up costs, and forces everyone to juggle multiple logins and browser tabs.

In a recent Earmark Expo webinar hosted by Blake Oliver, CPA, and David Leary—featuring Michael Salmon from Canopy—this issue of app overload took center stage. The panel discussed how modern practice management solutions are helping firms consolidate key functions, such as document management, task workflows, and client communication, into a single, unified platform. By reducing the need to stitch together a half-dozen stand-alone apps, unified solutions promise to free practitioners from the headache of endless browser tabs—without sacrificing cloud-based systems’ flexibility.

Why Are Firms Drowning in Apps?

Over the last decade, cloud technology has been seen as the solution for any time, anywhere, access to client data. But the “cloud” itself splintered into multiple tools—one for e-signatures, one for time tracking, another for document storage, yet another for proposals, and so on.

“Cloud solutions are definitely more flexible, and they solved a lot of problems for firms,” Oliver explains. “But we lost that all-in-one simplicity that older desktop suites used to provide. Instead, we replaced those solutions with six or seven specialized apps that don’t always talk to each other.” The result is a hodgepodge of siloed systems, each with its own subscription cost and learning curve.

The Comeback of Unified Practice Management

The good news? After years of fragmentation, the pendulum is swinging back toward unified practice management. Modern, cloud-based platforms combine core firm functions—like workflow, document sharing, e-signatures, billing, and even specialized features such as IRS transcript downloads—into a single ecosystem. Rather than forcing staff to bounce between multiple browser tabs, these tools consolidate everything under one login.

Michael Salmon, Senior Solutions Consultant at Canopy, highlights how these new practice management solutions address app fatigue. “There’s a direct integration with your email and calendar, so you never have to leave the system to schedule meetings or attach emails to tasks,” he explains. “Tasks, time tracking, billing, document management, e-signature—they’re all under one roof. That way, you’re not paying for five or six different subscriptions, nor do you have staff re-entering data.”

An Inside Look at Modern Features

While these capabilities highlight how modern platforms unify daily workflows, the next step is understanding what it takes to implement such solutions—and whether the cost and transition effort truly pay off for your firm.

1. Integrated Email & Calendar
Instead of flipping between Outlook or Gmail and your tasks, modern platforms pull your mailbox and calendar into the same screen. You can attach an email thread to a specific client project @-mention colleagues for internal discussions or launch a timer for billable work right from the email. This not only keeps all client communication in one place but also streamlines collaboration when multiple team members touch the same client.

2. Document Management & Client Portals
A single repository for all client documents—complete with clear privacy controls—removes the need for separate internal and external storage systems. “One of the biggest pain points we solved was having to create separate folder structures just to hide files from the client,” says Salmon. “Now you can mark an item as ‘visible’ or ‘private’ and keep everything in one folder. Clients can log into a custom-branded portal, see just the documents you’ve shared, sign them electronically, or upload files using the same portal.”

3. Workflow & Task Automation
Teams can create repeatable templates for engagements like 1040 prep or monthly bookkeeping. Each step in the process—requesting bank statements, reconciling accounts, and final reviews—can be built into a template with clear deadlines and staff assignments. Automated triggers (e.g., “Once the 1065 task is completed, create a 1040 task”) mean fewer manual handoffs and status-check emails. “It’s about letting the system manage the process so you can focus on the client,” Salmon notes.

4. Time Tracking & Billing
Time spent on tasks can be tracked through start-stop timers or recorded after the fact. Integrated billing converts that tracked time into invoices, which can be sent to the same portal for client payment. Because everything is connected, you reduce data entry and gain real-time visibility into WIP, outstanding invoices, and staff performance.

5. Tax Resolution & Specialized Tools
Firms looking to expand into more profitable services—such as tax resolution—can benefit from integrated modules that retrieve IRS transcripts and notices. “You can pull a client’s transcripts without leaving the platform, identify issues, generate forms, and keep everything organized with the rest of your workflow,” says Salmon. This single login for tax controversy work, e-signatures, and billing cuts down on even more overhead.

6. AI-Powered Assistance
Many modern solutions now embed AI to handle repetitive tasks and speed up communications. For example, you can draft email responses to client questions based on context or generate custom live dashboards by simply typing a question (“Show me my top-billed clients this quarter”).

What About Cost and Implementation?

One concern is cost. While an all-in-one platform may carry a monthly subscription per user, many firms find they’re actually saving money by replacing half a dozen (or more) separate systems. “If you’re paying for e-sign, file storage, workflow, and a handful of other apps separately, switching to an all-in-one platform often consolidates spend. Plus, your staff only has to learn one solution,” Salmon says.

Implementation can take a few weeks or months, depending on how many modules a firm adopts and how many years of documents and client data must be migrated. Providers like Canopy typically offer implementation specialists to help firms with data imports, template setup, and staff training. “Nobody wants to feel overwhelmed during adoption,” Salmon admits. “But once your data and clients are in one system, the day-to-day efficiency gains make it worthwhile.”

The Future: Efficiency Without Fragmentation

Unified, cloud-based practice management software restores the simplicity that desktop-era systems once provided—while adding the flexibility, mobility, and real-time collaboration capabilities that modern firms demand. By eliminating the need for countless browser tabs and apps, staff can stay focused on delivering client value rather than wrestling with technology.

“We don’t even call it ‘cloud’ anymore,” Oliver points out. “This is just how firms operate now. The difference is you no longer have to build your own Frankenstein’s monster of apps. You can get back to an all-in-one ecosystem but built for the realities of today’s accounting practice.”

If you’re curious to see exactly how an integrated solution works in real-time—email, tasks, billing, client requests, e-signatures, and more—watch the full Earmark Expo webinar featuring a hands-on demo of Canopy. You’ll see firsthand how unifying key functions can dramatically reduce the friction that comes with managing 50 separate apps.

Accounting Firms Boost Profits by 10% Without Losing Clients—Here’s How

Blake Oliver · February 7, 2025 ·

Are outdated billing practices holding your accounting firm back?

While many firms see proposal and payment systems as necessary yet purely administrative, forward-thinking practitioners are discovering their immense potential to reshape client relationships—and boost profitability.

In a recent Earmark Expo webinar, Tom Maxwell of Ignition showed how modern engagement systems do more than simply streamline operations. They fundamentally change how clients perceive and value accounting services. Forward-thinking CPAs are eliminating accounts receivable, implementing annual price increases, and shifting from after-the-fact billing to genuine value-based partnerships.

The results are striking: Firms report implementing 10% annual price increases with no negative impact on client acceptance rates. More importantly, they’re building stronger relationships rooted in transparency, clarity, and mutual respect.

Below, we explore how these systems turn traditional billing bottlenecks into opportunities for transformation.

The Billing Bottleneck: More Than Just a Payment Problem

For many accounting firms, getting paid feels like an administrative hassle. However, according to Tom Maxwell, this challenge runs deeper—right to the heart of client relationships and firm profitability.

After talking to thousands of firms, Tom identified three main reasons clients struggle to see the true value of accounting services:

Mandatory compliance work: Clients often see compliance as a “must-do” rather than a “value-add.”
Expertise gap: Clients rarely grasp the depth of expertise required for high-quality work.
Value disconnect: When billing happens long after services begin, clients lose sight of the direct benefit.

The result is a vicious cycle of payment delays and weaker client relationships. But forward-thinking firms find that modern engagement systems address both the practical and psychological barriers head-on—starting with the first client interaction.

Transforming Client Engagement from Day One

Modern engagement systems reshape the client experience right from the start, setting clear expectations and articulating value. Gone are outdated PDF proposals, manual credit card processing, and clunky engagement letters—all of which can subtly lower the perceived value of your services.

Instead, clients receive a digital, professional proposal that:

Clearly lays out services and value
Offers up to three package options with different billing frequencies
Guarantees payment authorization before work begins

“My favorite feature,” Tom says, “is that clients must enter payment information before accepting the proposal. That ensures you get paid for your services before you even get started.”

This process is also more secure—no more mishandling of credit card details. Once clients accept a proposal, they receive a signed engagement letter, and their payment information is securely stored for future billing. This streamlined approach does more than save time; it also signals professionalism and shifts the conversation from awkward payment requests to demonstrating tangible client value.

From Reactive to Proactive: Managing Dynamic Client Relationships

With a rock-solid foundation in place, modern systems empower firms to become more proactive. They not only enable systematic price increases but also enhance client relationships.

“We found that Ignition customers were increasing prices by about 10% on average in the past year,” Tom explains. “And when we added the feature enabling a standard price increase, there was no change to proposal acceptance rates.”

These tools also end stressful negotiations around scope creep or service changes. Firms can quickly update both service levels and pricing, and automated billing continues seamlessly. Every adjustment is tracked for full transparency, reducing tensions and letting both parties focus on a healthy working relationship.

Integrated workflows further enhance automation. For instance, if you integrate payroll data, your fees can automatically scale based on fluctuating employee counts—so you’re always fairly compensated as client needs evolve. By treating billing adjustments and scope changes as a routine, expected part of the engagement, firms solidify their value without appearing adversarial or inflexible.

Embracing Modern Engagement Systems: The Path to Business Transformation

This evolution—from billing bottleneck to strategic asset—goes beyond operational efficiency. It marks a foundational shift in how firms approach client relationships.

By tackling the practical and psychological pain points of billing, modern engagement systems let you focus on what truly matters: delivering measurable value. The evidence is clear:

Accounts receivable evaporates
Annual fee increases of 10% become standard—with minimal client pushback
Client relationships strengthen through transparency and respect

Watch the full Earmark Expo to see these tools in action. You’ll see how industry leaders implement automated billing, consistent price updates, and stronger client relationships—freeing them to concentrate on higher-value, growth-oriented services.

The future favors firms that view proposal and payment systems as strategic levers for better, more profitable client relationships. The question isn’t if you should upgrade your engagement systems—it’s how soon you can begin.

How a Red Chair is Transforming Client Relationships in Accounting

Blake Oliver · January 28, 2025 ·

In the conference room of a CPA firm, there’s a bright red chair—off-limits to employees. It’s reserved for clients, even if they’re not physically present. When the client can’t attend a meeting, the chair stays empty, yet serves as a vivid symbol: imagine the client is here, listening to every word. This approach to client-centric service cuts through the day-to-day grind and reminds everyone on the team that the client’s best interests must guide every decision.

On the Earmark Podcast, I spoke with Kyle Walters—Managing Director of Atlas Wealth Advisors and Partner at CPAs & Advisors—about the power of integrating wealth management with accounting services. Walters explained how his unique perspective as a longtime financial advisor, combined with the expertise of his CPA partners, opened the door to a more cohesive, future-focused experience for clients.

Why Integrate Wealth Management and Accounting?

Kyle Walters grew up in financial planning. For two decades, he helped families invest, save on taxes, and retire comfortably. But he noticed a common frustration: clients viewed their financial picture as disjointed. Their CPA was crunching past numbers and tax returns, while their financial advisor was projecting out into the future. Neither professional was fully aware of what the other was doing.

By bringing both wealth management and tax under one roof, Walters realized he could deliver a more seamless client experience. Rather than running in circles between two trusted advisors—one in the present and one in the future—the client can enjoy an integrated dialogue. In Kyle’s words: “If you can get your CPA, your financial advisor, and your client on the same call, you solve problems in five minutes that otherwise would drag on for weeks.”

Two Ongoing Relationships: CPA + Financial Advisor

When it comes to finances, most families or business owners consistently rely on two professionals:

A CPA or Tax Specialist – Focused on bookkeeping, tax returns, and making sure numbers are correct and on time.
A Financial Planner or Wealth Manager – Oriented toward helping people invest smarter, plan for retirement, and meet long-term goals.

Because these two experts often operate independently, the client must shuffle data and questions back and forth. Even little miscommunications can create confusion, missed deadlines, or unnecessary stress. The integrated model aims to remove the client from this “middleman” role. Whether it’s about a new business launch, a company sale, or an unexpected life event, a single cohesive team can handle both tax and wealth implications together.

A Fresh Perspective in the CPA Firm

Part of what makes Walters’s model so successful is that he’s not a CPA. Instead, he brings a financial advisor’s perspective to firm operations. CPAs traditionally focus on deadlines, precise data, and compliance. Financial advisors naturally explore client goals, family needs, and big-picture strategies. Together, these mindsets create a more robust decision-making process.

His journey to integrate services involved finding two CPA firm owners who shared his vision. They pooled resources, formed an entirely new firm, and established a culture where neither side worked in isolation. Now, the CPAs ensure the numbers are accurate and deadlines met, while Walters and his advisory team look forward—helping clients see how today’s financial decisions ripple into tomorrow.

The Power of the Red Chair

Early on, Walters noticed language in internal meetings that sometimes cast the client as an “obstacle”: “The client isn’t getting us their documents fast enough” or “The client doesn’t understand what we need.” To change the tone, he placed a bright red chair at the table, designated it for the client, and instructed the team to speak as if the client were right there—listening, seeing how they’re spoken about.

This seemingly small gesture fosters empathy. Team members are reminded clients don’t speak accounting jargon all day—if they knew how to gather every document perfectly, they wouldn’t need a CPA. They’re juggling businesses, families, and complexities. By imagining them in the red chair, the firm reframed their role from “client is a problem” to “client needs our help.”

Overcoming the Usual Pain Points

Walters regularly hears client feedback from both sides—the CPA perspective and the wealth management perspective. Three major pain points come up time and again:

Slow or Nonexistent Communication
Clients want speedy responses, or at least acknowledgment that their questions matter. Even a brief courtesy check-in can help them feel valued.

Inflexible Processes & Crunch Deadlines
Traditional accounting often revolves around one or two deadlines. Firms endure a stressful “rush to the finish,” leaving little bandwidth for deeper client conversations. Scheduling tax return preparation into monthly or quarterly cohorts can solve this. When clients understand that being “extended” won’t lead to penalties—and that it can mean better guidance throughout the year—most are happy to follow a more strategic timetable.

Disjointed Advice
A business owner selling their company doesn’t just need a properly filed return—they need a plan to handle the influx of cash, tax implications, and possibly a shift in personal goals. When multiple advisors operate in silos, misalignment and confusion can cost a client time and money.

Interestingly, small tax mistakes rarely drive clients away. They understand honest errors can be corrected. What they won’t tolerate is feeling unappreciated, being ignored, or left in the dark.

Delivering True Integration

Under an integrated model, advisory conversations flow naturally. For example, a client might hop on a Zoom call with their CPA and financial advisor at the same time to discuss mid-year tax estimates, projected income, and potential investment shifts. Instead of playing telephone, the client watches their two experts coordinate in real-time.

Year-round scheduling also adds a proactive structure:

Early in the year – Identify high-complexity clients or those who prefer timely filing, and complete the first batch of returns. Extend any clients not filed by April 15.
Middle of the year – Perform “pulse checks” on tax projections and investment performance. Complete the second batch of returns.
Later in the year – Finish up any open client returns.
End of the year – Engage in tax planning and forward-looking financial decisions. This is prime time for capturing deductions or shifting money before year-end.

By spreading out the busy season, both CPAs and advisors can provide the attention that clients crave.

Looking Ahead: AI and the Evolving Role of the Advisor

As technology advances—particularly artificial intelligence—routine accounting tasks like sorting transactions or populating tax forms will become more automated. Rather than viewing this as competition, forward-thinking professionals see AI as a powerful ally: It handles rote tasks so humans can focus on relationships, nuanced conversations, and strategic planning. The CPA or financial advisor of the future will be less about data entry and more about empathetic counsel.

Walters believes clients ultimately pay for clarity, confidence, and guidance. In this new landscape, the “trusted advisor” is the one who integrates all the moving parts of someone’s finances and helps them make better decisions. AI can help gather data, but the human element—like making someone feel heard or reflecting on their family goals—still belongs to the professionals.

A Single Seat for Service

Across the table sits that red chair—occupied or not—representing the heartbeat of a firm that puts the client first. By merging wealth management and tax expertise, firms create a single seat where every financial question can land. The result? Less confusion, fewer missed opportunities, and a client who genuinely feels they have a team working together for their benefit.

Want to hear more? Listen to the full discussion on the Earmark Podcast, where Kyle Walters delves deeper into his integrated approach, shares the motivation behind the red chair, and explains how proactive scheduling can transform the busy season from a burden to a strategic advantage.

Building a Successful International Tax Practice: Lessons from Japan

Blake Oliver · January 28, 2025 ·

Nearing his 30th birthday, California CPA and former English teacher Eric Azevedo found himself at a career crossroads. Having spent years in rural Japan teaching English, he longed for a profession with greater stability and higher earning potential. Rather than pursuing law school as he once planned—or even a career in software—Eric ultimately chose accounting. Little did he know that studying at California community colleges for the CPA Exam would pave the way for a thriving international tax practice serving American expatriates across Japan.

In a recent interview on the Earmark Podcast, Eric opened up about his unique journey from philosophy major to accounting professional, revealing the practical realities of working in a different culture and navigating complex dual-tax systems.

From Santa Monica College to Tokyo: A Career-Changer’s Leap

Eric’s decision to become a CPA began when he returned to California after several years in Japan. Enrolling at Santa Monica College and Irvine Valley College, he completed the accounting courses required to sit for the CPA Exam—often taking advantage of online classes to balance work and study. Within about four years of taking his very first accounting class, Eric earned his license.

Opportunity knocked almost immediately: a single Skype interview led to a job offer at a Tokyo-based firm. Eric moved back to Japan on short notice, eager to gain experience in both U.S. and Japanese tax systems.

Bridging Two Tax Systems—And Two Cultures

Once in Tokyo, Eric encountered very different tax structures.

The United States is one of only two countries in the world—alongside Eritrea—with a citizenship-based tax system. Americans living in Japan must still file U.S. tax returns, including complex forms like 5471 (for owners of foreign companies) and FBAR (for foreign bank accounts over $10,000). Meanwhile, most Japanese rarely file returns at all—employers handle year-end payroll adjustments.

Understanding these differences—and guiding clients through them—is now Eric’s specialty.

Cultivating Cultural Fluency

Eric says that in Japan, communication styles tend to be less direct. Understanding when and how to speak up can determine whether a meeting proceeds smoothly or grinds to a halt.

Audits tend to be less adversarial. Eric says, “If you push too hard, you risk prolonging the process. It’s about staying polite and finding a solution.” This contrasts with the more confrontational style some CPAs experience in U.S. audits.

“I’m basically the only American in the office,” Eric says. “We have staff from Korea, China, the Philippines—all with a focus on serving foreign residents. It’s important to adapt culturally to make clients comfortable.” (Since our interview, Eric’s firm has added another US accountant to the team.)

Regarding the work culture, Eric’s firm’s founder intentionally avoided “salaryman” traditions of endless overtime and obligatory after-work gatherings, making the environment more appealing to foreign hires.

Life in Rural Japan: Remote Work, Bullet Trains, and Big Windows

After eight years in Tokyo, Eric relocated to the countryside. He now works as a contract employee for his old firm while also handling his own U.S. tax clients. Living among forests and mountains, he’s built a home office full of natural light—complete with high-speed internet that makes remote work seamless.

Commute: Eric travels to Tokyo twice a month, taking a 70-minute ride on the bullet train.
Daily Routine: A self-described “not super early riser,” Eric starts his workday around 9 or 10 a.m., relying on video calls and remote access to firm software.
Nature & Wildlife: Bears and wild boars roam nearby—quite a change from Eric’s Tokyo apartment.
Cultural Hobbies: Weekends are reserved for hobbies and relaxation; onsens (hot springs) are among Eric’s favorite escapes.

Fees, Growth, and Training the Next Generation

Eric’s firm charges fixed fees aligned with client revenue, reflecting typical local practice. For his U.S. expat services, he charges per form but keeps fees moderate—aware that many expats must file only because of America’s unique rules.

Word of mouth has fueled steady growth. He’s now training a colleague—a Chinese national finishing her U.S. CPA credentials—to handle returns for more straightforward clients. This arrangement frees Eric for higher-complexity cases while positioning the practice for further expansion.

“I don’t advertise,” Eric explains. “Clients tend to find me through referrals. My challenge is managing time and figuring out how to scale.”

Advice for Prospective Expat CPAs

For aspiring accountants who are interested in working abroad, Eric’s journey serves as a valuable guide:

Focus on Fundamentals First: Attaining a U.S. CPA license can be done flexibly through community college coursework and exam prep—even if you’re overseas.
Leverage Your Language Skills: Fluency in the local language is invaluable. Eric’s Japanese helped him land work in Tokyo more easily.
Adapt to Local Norms: Understand that professional etiquette, social expectations, and communication styles vary greatly. Listen first, then speak.
Stay Open to Opportunity: Eric’s entire career launched from one Skype call and a willingness to move back to Japan on short notice.

Making the Most of Japan: Travel Tips

Whether you plan to work in Japan or just visit, Eric recommends:

Tokyo: An endless array of districts, restaurants, and cultural sites.
Historic Towns: Kurashiki in Okayama Prefecture offers a glimpse into samurai-era architecture.
Onsen Retreats: For a restorative experience, explore hot spring destinations off the beaten path.
Autumn Visits: Fall foliage in rural Japan rivals any scenic backdrop, and cooler weather makes the onsen even more inviting.

Conclusion: Merging Cultures, Mastering Tax

Eric Azevedo’s journey proves that building a successful international tax practice requires more than technical knowledge. Cultural competence, flexible communication, and a willingness to adapt to new ways of doing business are critical. In navigating both U.S. expat tax complexities and Japan’s distinct work culture, Eric shows how melding two worlds can create a uniquely rewarding career path.

To hear Eric’s full story listen to his interview on the Earmark Podcast.