Matt Kidd, CPA, of Kidd Advisors hosted a tax-day party at an Irish pub near his Livonia, MI office. About 50 clients and prospects came. The tab was roughly $3,000.
Many guests are $500 annualtax return clients. Matt joked that they “probably ate and drank the profit margin” out of those returns.
So why would a mostly remote firm owner spend money bringing them together? Because a relationship can outlast the transaction that started it.
In Season 5, Episode 21 of Who’s Really the BOSS?, Matt joins hosts Rachel and Marcus Dillon to discuss investing in people while technology changes the work. They focus on choosing where time matters and making those relationships count.
Give employees a reason to improve the work
Matt’s four-person firm, including him, is about 2.5 full-time equivalents. They have flexible schedules with assigned phone coverage. Weekly check-ins cover each person’s best moment and current challenges, while connecting the accounting and financial-planning sides of the business.
He also introduced weekly “innovation meetings” focused on AI. After three or four weeks of brainstorming, the participating employees began building tools to solve their own frustrations.
Matt couldn’t identify every problem himself. He was too removed from much of their daily work. Instead, employees chose what to fix.
They were particularly motivated because Matt made the benefit clear: save time, and you can work less. Bring in more work, and the firm’s profitability-based bonus structure lets you earn more.
“They’re building way more than I am at this point,” he said.
Marcus described a challenge in his own firm: testing can consume time while client work still needs to get done. Matt acknowledged that tools used by two or three people are easier to adjust than tools rolled out across a larger organization.
He returned to the idea of letting employees choose meaningful problems and explaining how they’ll share in the gains. But better tools aren’t the only way to show people they matter.
Make appreciation a habit
Matt offers maternity and paternity leave and has paid substantial profit sharing. Still, he believes benefits don’t replace regular, genuine thanks.
“The biggest thing is just actually telling them you appreciate them,” he said. During tax season, he tries to recognize something specific at least once a day.
Rachel builds reminders into the Dillons’ routines, including weekly written check-ins, one-on-one conversations at least every other week, direct messages, and handwritten notes. As teams grow and spread out, appreciation needs a rhythm.
Marcus suggests thanking employees in front of someone they love, such as a spouse, parent, or another important person. Rachel adds that a card addressed to your team member’s special person can work when you’re remote.
Trust also requires listening. When an employee challenged Matt, he thought it over, realized the employee was right, and apologized. He credits that openness with building a collaborative team where people can question one another.
You don’t need a large budget to practice this. Give specific thanks, address problems promptly, and accept feedback yourself. Then apply that same care to how you spend time with clients.
Choose client relationships before filling your calendar
Matt bought his practice on September 1, 2017. At the time of recording, he expects revenue of about $750,000 for the accounting firm side, up from roughly $350,000 when he acquired it. He projects financial planning to add another $200,000.
Yet growth doesn’t mean keeping every client. With one accountant planning to retire within six months, Matt is considering downsizing and releasing some nonideal legacy clients. He already reserves most in-person meetings for financial-planning clients and the top 10% of accounting firm clients. In 2025, he spent just 27 days in the office, 17 of them in March.
His advice is to “figure out which clients you really enjoy working with,” then identify needs beyond your current services. That process led him into financial planning because many existing clients needed personal planning, rather than business advisory work.
Selective attention doesn’t mean abandoning everyone else. It means finding other ways to stay connected.
Build connections beyond the annual tax return
For clients Matt sees only once a year, appreciation events help put a face to his name. When retirement or an inheritance creates a planning need, they know whom to call.
The pub party idea came from an earlier food-truck event, where a conversation with a recently retired client led to assets moving into Matt’s advisory practice.
These gatherings also give the team something to enjoy. And, as Rachel noted, a lower-fee client may have friends or relatives who become excellent prospects.
Marcus described the broader shift as “moving from compliance to community.” Personal touches like handwritten thank-you cards, selected client gifts, and team photos that include family members support that shift.
Financial planning also changes whom you serve. Matt explained that, unlike many business engagements, financial planning often involves both spouses. His mother’s favorite thing about her advisor was the Christmas basket. That’s a reminder that different people notice different forms of care.
Timing helps, too. Rachel found that gifts sent in May stood out more than gifts sent during crowded December weeks.
Those connections bring the conversation back to the firm you want to build.
Build a community you want to belong to
Start with three choices:
- Share the gains from better work. Give employees room to solve problems and benefit from the results.
- Make recognition personal. Notice contributions, listen to criticism, and include the people important to your team.
- Invest in relationships deliberately. Choose clients you enjoy serving, understand their needs, and stay connected beyond deadlines.
Listen to the full episode for Matt’s full conversation with Rachel and Marcus about building a firm around people, not just revenue.
Rachel and Marcus Dillon, CPA, own a national, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 28 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with Streamlined OS, an operating system for accounting firms, mastermind groups, and one-on-one advisory.
