Who's Really the Boss

Design Better Habits, Build a Better Accounting Firm

Earmark Team · February 25, 2025 ·

When Rachel Dillon began her 4:30 a.m. workouts in January 2010, she only knew she needed a routine that fit her teaching schedule. She had no idea this personal commitment would eventually shape how she and her husband, Marcus Dillon, run their accounting firm, Dillon Business Advisors. Years later, they discovered that the same habits guiding their health journey could also help them overhaul their business.

Starting from Excess and Finding Focus

In 2016, Rachel and Marcus merged their firm with a mentor’s practice. This left them juggling more clients than they could serve effectively. At the same time, they were both working with a nutrition coach to improve their health. Seeing how steady, daily actions led to personal change, they realized these principles could solve their firm’s overload problem.

The final puzzle pieces came together when the Dillons read James Clear’s Atomic Habits. They recognized they’d already been applying many of his ideas to their personal lives and their accounting practice. This sparked an intentional approach to three principles that continue to guide their growth today.

1. Make It Obvious and Easy

A big lesson from Atomic Habits is turning good intentions into obvious, easy actions. The Dillons did this by scheduling important firm tasks at the start of each year. They get quarterly client meetings, team scorecards, and even vacation windows on the calendar long before anything else can crowd them out.

Rachel explains, “What gets measured, gets managed, and what gets scheduled is more likely to happen.”

Going on a family vacation during spring break is nearly unheard of in accounting firms as it often falls right in the middle of the March 15th and April 15th tax deadlines. But the Dillons started blocking off spring break in small steps. At first, it was just a few days, but then they eventually built up to the entire week. This helped them balance busy season deadlines with time for family. Over time, team members also learned that when tasks and priorities are clearly laid out, everyone stays accountable.

2. Environment Design

Environment design means shaping spaces and systems so the right behaviors become natural. When Rachel and Marcus wanted more flexibility for their team, they began transitioning to remote work. Before going fully remote, they tested digital tools like Microsoft Teams so people became comfortable collaborating online. They also invested in proper desks, monitors, and other equipment rather than letting everyone rely on a single laptop at the dining room table.

According to Marcus, “If someone stayed on one small laptop for five years, they wouldn’t be as effective. Actually spending money on environmental design was a good call.” By building a flexible, remote-first culture, they kept talented staff who valued autonomy. They also served clients more effectively because team members had the right setups to do their work.

3. Identity-Based Habits

Finally, the Dillons aligned their daily actions with the values and identity they wanted for their firm. Marcus and Rachel emphasize transparency, so they share their objectives early—even when they’re unsure how plans will unfold. For example, they’ve begun exploring possible firm acquisitions to grow beyond the standard one-client-at-a-time model. They keep their team in the loop even before potential deals become certain.

“Transparent leaders do this,” says Rachel. Their team appreciates being trusted with big-picture thinking and offers ideas for making acquisitions smoother. Marcus adds that their firm’s vision and values mirror their personal ones, so it feels natural rather than forced. When beliefs, words, and actions match, big changes tend to stick.

Personal Habits Fuel Professional Results

The Dillons’ story shows that lasting change often starts with personal commitments. By applying principles of habit formation to their firm—making tasks obvious, designing supportive environments, and acting consistently with their values—they’ve built an organization that embraces growth year-round.

To learn more about how Rachel and Marcus continue to evolve their firm and stay true to their values, listen to the full episode of the “Who’s Really the Boss” podcast. You can also visit Collective.cpa for more resources to help you design a modern accounting practice.

Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with firm resources, education, and operational strategy through community, groups, and one-on-one advisory.

Building Sustainable Accountability: How to Maintain Momentum Year-Round

Earmark Team · February 24, 2025 ·

Every January, millions of people set out to transform their habits, only to find themselves struggling by mid-month. In fact, the second Friday of January is known as “Quitters Day,” when many throw in the towel on their New Year’s resolutions. For accounting professionals, the challenges compound: a 2024 Forbes study reports that 50% of resolution-makers quit by March—precisely when tax season intensity is at its peak.

In a recent episode of the Who’s Really the BOSS? podcast, Rachel and Marcus Dillon of Dillon Business Advisors (DBA) acknowledge these hurdles but also share practical ways to overcome them. As accounting firm owners, they see firsthand how easy it is for accounting professionals to abandon both personal and professional goals amid looming deadlines and long work hours. Yet the Dillons have developed reliable strategies—grounded in accountability and careful planning—that can keep momentum strong year-round.

The Unique Pressure on CPA Firm Owners

While most people struggle to sustain enthusiasm after the holidays, accounting firm owners have a double challenge. January’s fresh start quickly collides with ramping up for busy season, and by the end of March, many people’s goals have fallen by the wayside. After April 15th, it’s tempting to celebrate the season’s end or simply recover, making it even harder to pick up abandoned routines.

“I just do not like January at all,” admits Marcus. “A lot of us grew up in accounting—we dread January and starting the year new.” When you start with a clean P&L and the celebration of last year’s successes ends, accountants often feel they’re starting from scratch. Layer on the time crunch of tax deadlines, and it’s easy to see why many resolutions vanish by March.

Rachel adds, “You think ‘I just need to get through the next few weeks or this deadline,’ and really, you just let everything from January and February go.” Instead of waiting for post-deadline recovery to refocus, the Dillons recommend building accountability systems that prevent goals from slipping in the first place.

Goals for 2025: Firm Growth and Beyond

The Dillons prefer the concept of measurable goals over open-ended resolutions. DBA heads into 2025 with clear objectives:

Organic growth. DBA plans to add 15 new monthly recurring clients in 2025. With a price point for each client at $2,000 or more per month, this goal translates to adding $30,000 in new monthly recurring revenue by year’s end. To manage quality control, DBA limits each “pod” to two new client onboardings per month.
Potential firm acquisition. Beyond organic growth, the Dillons are open to non-organic expansion through the right acquisition. This approach provides additional career advancement opportunities for existing team members.
Technology & process improvements. Newly hired Director of Technology, Angel Sabino, will evaluate DBA’s IT systems and relationships to ensure they can support future growth. The team plans to expand its use of Keeper for client workflows and more automation in their onboarding process. They also plan to eliminate software they’re not fully testing or utilizing to free up room in the budget and focus on enhancing core platforms.
Team development. Client Service Managers meet monthly to share best practices, while Controllers hold their own dedicated development sessions. This ensures training and collaboration throughout the year. New and existing SMEs (Payroll, Tax, QBO) serve as go-to resources for the rest of the team. DBA plans to hire additional staff, including a Controller and a new Client Service Manager Assistant through TOA Global.

“Even though goals like these can feel daunting, we break them down,” Marcus explains. “We track them month by month, adding them to our weekly meeting agendas and quarterly reviews. That way, no one person is carrying the full burden, and we can re-evaluate often.”

Personal Accountability: Small Steps, Big Payoffs

Both Rachel and Marcus rely on personal accountability to stay on track.

Fifteen years ago, Rachel began a morning weightlifting habit and hasn’t stopped. In 2024, she hit 302 workouts—exceeding her personal target of 300—by tracking each session in a free app. Visibility of her progress, especially late in the year, motivated her to stick with the plan.

“I track everything so I can see how far I’ve come,” Rachel explains. “When we traveled to New York, I still got up early because I knew I had a goal I wanted to meet.”

Marcus uses a structured approach spanning faith, marriage, health, and more. “I assign a measurable goal or metric to each category—did I do it or not?” he says. That clarity helps him refocus on days he would rather skip workouts or other commitments.

“Sometimes I literally break a workout into percentage points. If I’m halfway done, that’s 50%, and I tell myself I’m not going to quit at 50%. Same when I’m at 75%. It keeps me motivated.”

Accountability Strategies to Withstand Tax Season

How do you maintain progress toward goals when you’re knee-deep in client work? The Dillons recommend three main strategies:

Break it down. Make goals specific and measurable, then divide them into weekly or daily steps. Whether it’s limiting client onboarding each month or aiming for 20-minute workouts, smaller tasks are more achievable.

Keep it visible. DBA incorporates goals into weekly meeting agendas, ensuring they’re never “out of sight, out of mind.” Similarly, Rachel’s app and Marcus’s weekly check-ins with his accountability partner keep them aware of their personal targets.

Stay flexible. Life happens—especially during busy season. The Dillons suggest building in reassessment milestones (e.g., a mid-year retreat in May or June) to pivot if goals no longer make sense. Instead of abandoning them, adjust and realign.

Looking Ahead: The Collective by DBA Event

For accountants seeking deeper connections and guidance, the Dillons’ peer community, Collective by DBA, is hosting an in-person event on May 5th–6th in The Woodlands, Texas (with a third-day session on May 7th for forum members and one-on-one advisory clients).

Registration opens on January 28th, and only 50 seats are available. The retreat provides an opportunity to fine-tune your firm’s processes, swap insights with other leaders, and solidify your goals for the rest of the year.

“If it’s anything like our event last May, it’ll fill up fast,” Marcus says. “We’re building an agenda that dives into topics like firm growth, technology, and team structure—all the areas we’re working on ourselves.”

Maintaining Momentum Beyond January

While most resolutions taper off by March, the Dillons prove that real progress can happen any time of year—with the right structure. By breaking down targets, checking in frequently, and involving others, firm owners can continue working toward their goals well past busy season. Whether you’re building better habits in your personal life, scaling your firm, or both, the key is accountability—layered at the individual, team, and organizational levels.

Ready to learn more? Tune in to the Who’s Really the BOSS? podcast for the Dillons’ full conversation on goals and accountability, and consider joining them in May at Collective by DBA’s in-person event. Even in the throes of tax season, sustainable, measurable goals are possible when you have a plan—and a team—to keep you on track.

A Fresh Look at Accounting Firm Transitions Puts Quality of Life First

Earmark Team · February 2, 2025 ·

In a recent episode of the Who’s Really the Boss? podcast, attorney Sara Sharp joined hosts Rachel and Marcus Dillon to discuss the evolving world of accounting firm ownership, legal compliance, and how forward-thinking solutions like phantom equity can help firms thrive.

Sara, who works almost exclusively with CPAs on practice transitions and day-to-day compliance, sheds light on key issues every firm owner should consider—from multi-state employment laws to IRC Section 7216, which requires tax return preparers to protect clients’ tax return information or face possible criminal prosecution. Sara also discussed how creative ownership structures can bridge the gap between traditional partnerships and the need for modern flexibility.

From Compliance Challenges to Ownership Solutions

Rachel and Marcus initially engaged Sara to revisit the Dillon Business Advisors (DBA) employee handbook, recognizing that multi-state compliance for PTO and other policies was becoming increasingly complex. What started as a routine legal audit soon expanded into a broader conversation: How do small and mid-sized firms protect themselves legally while also planning for the future?

“A lot of people think signing up with a PEO solves everything,” explains Rachel, referencing how DBA initially assumed their Professional Employer Organization would handle compliance. “But we still discovered plenty of state-specific requirements.”

Sara points out that many accounting firms face challenges such as:

Multi-state labor laws require unique PTO accrual rules or payout stipulations
Contractor vs. employee misclassification can lead to costly fines
Sec. 7216 regulations mandate specific client consent forms when outsourcing tax prep or using contractors

Addressing these issues up front, says Sara, frees firms to focus on strategic goals like offering innovative ownership pathways.

Why Traditional Partnerships Feel Precarious

Despite the compliance work, most of Sara’s clients ultimately want guidance on ownership transitions, whether selling to a third party, merging with another practice, or rewarding top team members. She uses “one foot on the boat, one foot on the dock” to describe how many owners attempt to ease out of the business while transferring equity to new partners. This can create a drawn-out process where any sudden shift—divorce, health crisis, or relocation—throws everything off balance.

“You can set up a five-year partnership buy-in plan,” says Sara, “but if something goes wrong in year two, you’ve got a mess on your hands, with partial owners and complicated payouts.”

Phantom Equity: A Modern Alternative

At DBA, Marcus and Rachel wanted to recognize two key team members—Leslie Reeves, CPA and Amy McCarty, MBA—without forcing them to buy into a rapidly appreciating firm. “We’re not just talking about hours and ‘butts in seats,’” Marcus explains. “Leslie and Amy bring strategic value that far exceeds any traditional measure of partner track.”

The solution? A phantom equity plan. Sara helped them design an arrangement wherein these employees receive financial benefits tied to firm performance—just as if they owned a small percentage—but without actual stock in the company. They would still see real economic participation in a potential sale or buyout event.

“We’re going to treat you economically as though you are a 1% owner,” Sara notes, “but you’re not on the cap table. It’s simpler, and if someone leaves, they aren’t stuck with actual shares in the business.”

For Marcus and Rachel, this addresses talent retention—rewarding employees who already act like owners—and risk management: no messy buyouts if life circumstances change.

Evolving Valuations: From 1X Revenue to 8X SDE

Another factor driving new ownership models is how valuations have changed. Sara observes that many accounting firm owners still assume they’ll fetch about 1X gross revenue. Yet private equity, family offices, and younger entrepreneurs increasingly evaluate profitability. Instead of valuing a practice based on gross revenue, they’re basing it on earnings—often 4X to 8X seller discretionary earnings (SDE).

“Now that people realize it’s about cash flow, we see more sophisticated questions,” explains Sara. “Do you have digital relationships with clients? Are you reliant on face-to-face drop-offs? Efficient, profitable, tech-savvy firms can get premium multiples.”

Younger generations of accountants prioritize work-life balance and operational efficiency. They’re less inclined to log 70-hour weeks or maintain a physical office for clients to drop off paper forms. Sara says this cultural shift is clear in her legal practice:

“I’ve got buyers in their 20s and 30s who want to do everything in the cloud, automate workflows, and raise rates so they don’t have to manage thousands of low-margin returns. They’re running the business more cleverly.”

Looking Ahead: Aligning Compliance, Culture, and Ownership

As more firm owners realize they must adapt to multi-state employment, shifting professional values, and new valuation formulas, legal compliance and innovative ownership structures become intertwined. Whether ensuring your employee handbook meets Colorado PTO law or sending out proper Sec. 7216 disclosure forms, or designing phantom equity plans, the best solutions are protective and empowering.

“Firms want to preserve culture, recognize talent, and plan for what’s next,” says Sara. “But you can’t marry that boy just to keep from hurting his feelings,” she quips, invoking her mother’s advice on knowing when to walk away from a bad deal—or a rigid tradition that no longer fits.

By balancing compliance groundwork with creative reward systems, forward-thinking firms can attract and retain top talent, command higher valuations, and sleep peacefully at night, knowing they’ve protected themselves and their employees.

To hear more about Sara Sharp’s legal insights and how DBA structured its phantom equity plan, listen to the full episode of Who’s Really the Boss? podcast.

Uncover the Strategy That Turns Extended Leave into an Innovation Opportunity

Earmark Team · January 26, 2025 ·

When two team members announce overlapping maternity leaves, many firms would anticipate a major disruption. But when that scenario played out at Dillon Business Advisors, something remarkable happened: team efficiency improved, profitability rose, and the firm discovered innovative ways to serve its clients.

In a recent episode of the Who’s Really the Boss podcast, Lezlie Reeves, Fractional CFO at Dillon Business Advisors, discussed with hosts Rachel and Marcus Dillon how the firm transformed what could have been a significant operational challenge into a catalyst for growth. With a team of 15 employees serving numerous clients, extended employee leaves often spell strained client relationships and overwhelmed staff—issues many CPA firm owners know all too well.

Yet through methodical documentation, systematic training, and strategic role delegation, Dillon Business Advisors didn’t just maintain their service levels—they raised them. Their experience offers valuable lessons for any firm looking to build more resilient teams and sustainable growth.

Building the Foundation: Systematic Documentation

Before team members announced their leaves, Dillon Business Advisors had already laid the essential groundwork. They recognized a common issue in accounting firms: too much vital knowledge residing in employees’ heads.

“Many of our CSMs do such a great job, but a lot of things would live in their head,” explains Lezlie. “If they needed to be out or someone left unexpectedly, they were not covered.”

Their solution was straightforward: using Excel templates and Vimeo recordings, the team documented every client’s comprehensive workflow—from daily tasks and weekly responsibilities to monthly financial preparation and client contact details. Rather than creating more administrative burdens, they integrated documentation into normal processes: recording videos during actual client work and updating Excel templates in real-time.

The team had previously solved for password management by implementing Practice Protect, ensuring secure access to client systems wouldn’t become a bottleneck during employee absences and exits.

This foundation of systematic documentation paid off when employees announced their leaves. Instead of scrambling to capture processes and procedures, the firm focused on strategic preparation and training. It’s a powerful reminder that the best time to document critical workflows is before you need them.

Methodical Training: The Key to Seamless Transitions

With documentation in place, Dillon Business Advisors turned their attention to training team members over six to eight months.

The training began with basic daily tasks before progressing to specific client work. To avoid overwhelming both the trainers and the trainee, they introduced five clients at a time. This paced approach allowed the CSM Assistants to gain confidence with one cluster of clients before moving on.

“If you’ve ever trained someone, you know it is exhausting to train while you’re working,” Lezlie says.

To address this, the firm distributed training responsibilities across multiple team members instead of burdening a single trainer with 40 hours of instruction. Each group of clients followed a three-month progression:

1. Month One: The CSM Assistant shadowed the CSM.

2. Month Two: The CSM Assistant handled the work with the CSM shadowing.

3. Month Three: The CSM Assistant worked independently with support available.

By the time employees went on leave, their replacements were fully prepared and confident—a stark contrast to common last-minute handovers.

From Disruption to Opportunity: Strategic Role Distribution and Unexpected Benefits

Rather than assigning all responsibilities to controllers, Dillon Business Advisors strategically divided tasks. The CSM Assistant handled bank feeds, reconciliations, journal entries, and financial preparation, while controllers managed client communication, tax filings, and payroll. This balance prevented any team member from becoming overloaded and ensured critical deadlines were met.

An unexpected bonus soon emerged.

“One added benefit we’ve had is with the client service manager assistant and the controller stepping in on different tasks—they’re just putting a different set of eyes on things,” Lezlie notes. “They can reevaluate, maybe trying new ways of doing things.”

These fresh perspectives resulted in process improvements across multiple clients. Team efficiency grew, and rather than seeing a dip in profits during the leave periods, the firm saw an increase in profitability. When the team members returned from leave, they even requested to continue assistant support because it had enhanced their ability to serve clients effectively.

What began as a workaround for extended leave transformed into a sustainable model for growth, enabling the firm to create capacity without hiring more full-time CSMs. This led to more efficient workflows and improved profitability overall.

Turning Challenge into Opportunity

What started as leave preparation became a catalyst for enduring change at Dillon Business Advisors. Through systematic documentation, methodical training, and strategic role delegation, they not only maintained client service—but improved it.

By viewing extended leave not as an unavoidable disruption but as an opportunity for growth, accounting firms can build more resilient teams, streamline workflows, and create new paths for expansion.

Want to learn more about how Dillon Business Advisors transformed their approach to employee leave management? Listen to the full episode of the Who’s Really the Boss podcast for deeper insights and practical tips you can implement in your firm.

Breaking Free From the Tax Return Trap: Building an Advisory-First Accounting Practice

Earmark Team · December 5, 2024 ·

Tax revenue can be addictive. Each $1,000 return during tax season feels like security, building a predictable revenue stream that’s hard to walk away from. But what if there was a way to transform those same clients into relationships worth $15,000 per month?

In a recent episode of the Who’s Really the BOSS? podcast, hosts Rachel and Marcus Dillon shared how their firm broke free from the trap of transactional relationships. While many accounting firms remain caught in the cycle of seasonal tax work and basic compliance services, their story shows there is a different path forward.

Through strategic patience and value-focused communication, Dillon Business Advisors evolved from processing tax returns to providing comprehensive advisory services. This transformation wasn’t just about offering new services – it required fundamentally changing how they engaged with clients and demonstrated value.

Setting the Stage for Transformation

“In the early years, we were just taking numbers and plugging them into a program to get people compliant,” Marcus admits. “That’s what a tax return does.” This transactional approach defines many accounting firms’ early stages, but technology and changing client needs have opened the door to something more valuable: true advisory relationships.

This evolution requires a shift in the mindset around client relationships. Rather than trying to retain every client and any revenue, successful firms learn to approach client conversations with clear outcomes in mind: either clients opt into expanded services, or they’re referred elsewhere. This takes both confidence and a strategic vision.

“Go into the conversation assuming they’re no longer going to be a client,” Marcus advises. “Just assume they’re going to tell you no, and you’re going to have to refer them out.” This means having referral options ready before crucial conversations. It might seem counterintuitive, but this mindset builds stronger client relationships.

Many firms fall into the trap of accepting less than ideal arrangements that stretch into years of suboptimal relationships. “You kind of give in and it’s like any revenue is good revenue,” Marcus reflects. ” Yeah, we’ll keep doing your return for one more year, but that turns into two more years and three more years.” Instead, the Dillons recommend focusing time and energy on clients who demonstrate they value advisory relationships while confidently referring others to firms that better match their needs.

This selective approach sets the stage for transforming transactional relationships into something more valuable.

From Annual Tax Client to Monthly Advisory: A Case Study

To demonstrate how value-focused communication can transform client relationships, the Dillons shared a client story. Initially, this client, a large family group, paid the firm roughly $60,000 per year to prepare multiple tax returns. Today, that client is a $15,000 monthly advisory engagement – but this didn’t happen through aggressive selling or rushing the relationship.

As part of a client acquisition years ago, this client demonstrated they valued the firm’s expertise long before expanding services. Throughout the year, they would seek opinions and book additional consultations, showing they viewed the firm as more than just tax preparers. When business changes created new needs – including the departure of key team members – DBA laid the groundwork for expansion through years of trust-building.

The transition succeeded through what Rachel Dillon calls “reverse selling.” Rather than pushing services, they explained their standard processes and let the client discover how these services could address their needs. “By communicating what we do for other people, he found the ways it could work in his business,” Rachel explains. “We didn’t have to convince him.”

Clear communication about service structure proved crucial. When discussing delivery timelines, they were upfront about monthly financials being ready by the 15th rather than the 5th – a change from the client’s internal team. This transparency about service parameters allowed the client to make informed decisions about the transition.

The client even readily accepted onboarding fees, noting he didn’t have a problem paying for onboarding because he knew any conversion would have a cost with it.” This willingness stemmed from understanding the value proposition and having experienced the firm’s advisory capabilities over time.

While this transformation showcases what’s possible, many firm owners wonder how to begin their own evolution. The key is taking practical steps toward change.

Practical Steps Toward Transformation

For firm owners feeling overwhelmed by the prospect of transformation, Marcus suggests starting with a simple question: “If I were to invest $10 million in your business today, what would we do differently?” This thought experiment helps identify priorities and possibilities without the immediate pressure of financial constraints.

Often, the changes needed don’t require millions – they require strategic thinking and incremental steps. For example, rather than transforming 5,000 tax clients into advisory relationships at once, consider transitioning just 150 clients to create initial capacity. This selective approach aligns with the strategic patience needed for successful transformation.

“Your business does not look the way it does because you had a crappy tax season,” Marcus explains. “It is all the days of every year. That’s why your business looks like it does. And so to change that, you just have to take action.” This perspective helps overcome what Marcus calls the “addiction” to tax revenue – the comfort of seeing those annual returns stack up.

The key is breaking down barriers into manageable steps. Major costs, like hiring key team members, can be spread over time rather than needed upfront. A $150,000 annual salary becomes manageable when viewed as a monthly investment in growth. This same principle applies to transforming client relationships – progress happens through consistent, strategic actions rather than overnight change.

Moving Forward with Confidence

The journey from transactional relationships to trusted advisors isn’t just about changing service offerings – it’s about transforming how you engage with clients and demonstrate value. As the Dillons’ experience shows, success requires strategy, clear communication, and the confidence to pursue ideal client relationships.

The potential financial impact of transforming annual tax clients into monthly advisory relationships is significant. But equally important is the shift from seasonal stress to sustainable, year-round client partnerships that deliver value for both sides.

Listen to the full episode of the Who’s Really the BOSS? podcast to learn more about pricing structures, service delivery models, and specific client communication approaches that lead to successful transitions. Your evolution from tax preparer to trusted advisor awaits.