In Episode 59 of Cases & Cocktails, Bryan and Janice Eggleston welcome back one of the show’s most-requested guests—Michael Boatwright, CPA and founder of Boatwright CPA. Known for making taxes surprisingly engaging (and occasionally terrifying), Michael joins the conversation to break down what divorced or newly separated individuals need to know as they head into a new tax year.

Ep 59 - audio

Over a bold Hot Honey Peach Margarita, the group dives into filing status pitfalls, dependency disputes, and the financial reality shifts that often follow divorce.

Why December 31 Matters More Than You Think

Michael explains one of the most misunderstood tax rules: your filing status is determined by your marital status on December 31. If a divorce is finalized before the end of the year, a person may file as single (or head of household, if qualified) for the entire year. If not, they are still considered married—even if separated.

This rule alone explains why so many clients rush to finalize divorces before year-end. But Michael cautions that while filing jointly is often financially better overall, many divorcing couples choose filing status for non-tax reasons—usually emotional ones.

The Risk of Joint Returns After Divorce

Filing jointly requires both spouses to sign and accept joint and several liability, meaning either party can be held responsible for the full tax bill—even years later if the IRS audits the return. Michael stresses that this risk must be fully understood before signing, especially when trust between spouses has already broken down.

For CPAs, this creates ethical challenges. Once a couple is divorcing, advising one spouse over the other creates a conflict of interest, often requiring accountants to step back and work directly with attorneys instead.

Dependency Claims and IRS Disputes

One of the most common post-divorce tax conflicts involves claiming children as dependents. Michael explains that IRS rules rely on facts and circumstances, not just court orders. The parent with the most overnight stays during the year is typically considered the custodial parent for tax purposes—regardless of what the decree says.

When one parent improperly claims a child early in the year, the other parent may be forced to file on paper, submit Form 8332, and wait for the IRS to correct the issue. While the IRS will eventually award the credit to the correct parent, the delay can be stressful and financially disruptive.

New Reality, New Financial Strategy

Divorce often turns a two-income household into one, cuts retirement savings in half, and disrupts credit. Michael emphasizes the importance of updating W-4 withholding immediately after divorce. Employers will not adjust tax withholding unless instructed, which can lead to unpleasant surprises at filing time.

He also encourages clients to approach the new year with realism. Budgets change. Cash flow changes. And planning must adapt accordingly. The goal isn’t perfection—it’s avoiding avoidable mistakes.

The Takeaway

Episode 59 highlights a critical truth: divorce doesn’t end with the final decree. Taxes, finances, and planning decisions made in the months that follow can have long-lasting consequences. With clear guidance and early action, many post-divorce tax disasters can be avoided.

As Michael puts it plainly: “There’s always an option—but some options land you in jail.”

In Episode 58 of Cases & Cocktails, Bryan and Janice Eggleston are joined by producer Josh Sharon for a spirited—and unexpectedly viral—conversation that has nothing to do with divorce and everything to do with music, culture, and hot sports opinions. What began as an off-the-cuff comment in a prior episode exploded online, prompting Bryan to double down (and then triple down) on his stance: the 1990s were the apex of music as a whole, and hip-hop is the most influential genre in history.

Over a fresh Strawberry Paloma, the trio unpacks why this opinion struck such a nerve—and why Bryan refuses to walk it back.

Why the Comment Went Viral

The original clip—just over a minute long—generated 59 days of watch time, a statistic that stunned everyone involved. Janice jokes that Bryan didn’t realize what he’d unleashed because he doesn’t use social media. Josh, who was front-row for the chaos, heard comments ranging from thoughtful debate to outright threats of bodily harm over music preferences.

Despite the reaction, Bryan maintains the point wasn’t about dismissing other eras or genres, but about collective cultural impact. “Not the best individual artist,” he explains, “but the best moment where all genres peaked at the same time.”

The Case for the 90s

The discussion spans rock, R&B, hip-hop, and pop. Bryan argues that while other decades produced legendary artists, no other era matched the 1990s in cross-genre dominance. Rock was still powerful, R&B groups thrived, pop icons ruled the airwaves, and hip-hop went global.

Josh and Janice agree—with caveats. While acknowledging that the 1980s had unbeatable moments and the early 2000s produced strong individual artists, they struggle to name a genre that is stronger today than it was in the 90s.

Why Hip-Hop Changed Everything

Bryan’s strongest argument centers on hip-hop’s global reach. From clubs in Poland to tour buses in Morocco, he’s witnessed people who don’t speak English recite lyrics from 90s hip-hop classics. That level of cultural penetration, he argues, hasn’t been matched by any other genre.

The group also discusses how music consumption has changed—from albums and music videos to singles, ringtones, and streaming—and how that shift has altered creativity. In the 90s, artists built full albums and visual worlds. Today, success is often driven by hooks and algorithms rather than storytelling.

Music Videos, MTV, and Cultural Moments

One controversial online take suggested music videos “ruined” music. Bryan rejects that outright, pointing to iconic visuals like Thriller, Smooth Criminal, and Wu-Tang Clan’s Triumph as proof that videos elevated music rather than diminished it. MTV, TRL, and shared cultural moments created a communal experience that simply doesn’t exist in the same way today.

The Takeaway

Episode 58 is a reminder that music is one of the few things that still sparks passionate, cross-cultural conversation. While the debate over decades may never be settled, Bryan’s larger point stands: music once demanded time, attention, and investment—and something has been lost in the convenience of modern consumption.

As Bryan puts it, “If we can’t debate music civilly, how do we expect to debate anything else?”

In Episode 57 of Cases & Cocktails, Bryan and Janice Eggleston kick off the new year with a practical, encouraging conversation about reflection, planning, and proactive decision-making after divorce. Over a light and celebratory Fresh Start Spritzer—made with prosecco, elderflower liqueur, lemon juice, and Topo Chico—they focus on how January can set the tone for a healthier, more organized year for parents and children alike.

Why January Matters After Divorce

The Egglestons explain that once the holidays end, many parents finally have the mental space to reflect. The chaos slows, kids return to school, and reality sets in. For parents who are newly divorced—or still navigating litigation—this quiet period is an ideal time to look back at what worked, what didn’t, and what needs to change moving forward.

Rather than waiting until the next holiday season to address problems, Bryan encourages parents to start early. “If you didn’t like how the holidays went,” he explains, “don’t wait until November to try to fix it.” Courts move slowly, and proactive planning often makes the difference between meaningful change and frustration.

Custody Modifications: Start Early, Not Late

January is also a strategic time to consider whether existing custody orders still reflect a child’s best interests. Circumstances change—parents remarry, families relocate, kids’ needs evolve, and school or activity schedules shift.

Bryan and Janice emphasize that modifications don’t have to be dramatic. Sometimes small changes—like adjusting a weekday exchange or revising summer schedules—can significantly improve stability for children. And when parents can reach agreement, modifications can often be resolved without court battles.

Waiting until the last minute, however, can make parents appear reactive rather than thoughtful. Courts are more receptive when changes are requested well in advance and clearly tied to a child’s needs.

Financial and Legal Checkups

Beyond custody, the Egglestons remind listeners that the beginning of the year is a smart time to revisit finances. Divorce often changes tax filing status, income, and expenses, making early meetings with CPAs or financial advisors especially important.

They also highlight one commonly overlooked task: updating wills and estate plans. Many people forget to revise beneficiaries, guardianship designations, and trusts after divorce. January offers a clean slate to make sure everything aligns with current circumstances and protects children appropriately.

Small Steps Still Count

Janice acknowledges that tackling custody, finances, and estate planning all at once can feel overwhelming—especially for single parents. The key, she says, is not doing everything at once, but simply getting things moving. Scheduling appointments, setting reminders, and creating a loose plan can ease stress and prevent last-minute crises later in the year.

The Takeaway

Episode 57 is a reminder that a “fresh start” doesn’t require drastic resolutions. Thoughtful reflection, early planning, and small proactive steps can create stability for parents—and security for children—throughout the year ahead.

As Bryan sums it up: planning early isn’t about control, it’s about giving yourself and your kids the best chance to succeed.