Why Relationships Still Matter in Tax—and Why the Industry Is at Risk Without Them

Gabe Hogan didn’t set out to build a conventional tax firm—and that’s exactly the point.

As the founder of Palmettos & Prickly Pears, Gabe’s brand reflects a life lived between worlds: growing up in West Texas rodeo culture and later settling among the palm trees of Charleston, South Carolina. The name fits him, and that intentionality carries straight through to how he practices tax.

Gabe is a tax attorney by training, earned his LLM at SMU, and spent four years as an IRS agent. He jokes that he “wasn’t a good stormtrooper,” so he left the Death Star to help the good guys. But that experience gave him a rare, inside-out view of how the tax system actually works—and where it’s breaking down.

Gabe Hogan Puts relationships first in his business

Today, the biggest issue he sees in accounting and tax isn’t technical at all. It’s relational.

Today, the biggest issue he sees in accounting and tax isn’t technical at all. It’s relational.

Across the industry, service is declining fast. Clients can’t get their accountants on the phone. When they do, conversations are buried in jargon and stress. Accountants are overworked, burned out, retiring, or selling their firms. New talent is opting for tech and cybersecurity instead. Private equity is rolling up firms, and many practices are turning to AI and offshoring to survive.

Those tools aren’t inherently bad, Gabe notes—but they miss something fundamental.

Taxes aren’t purely rational. People aren’t purely rational. Every tax situation carries nuance, risk, emotion, and context that no metric or automation can fully capture. If you want a tax strategy done right, you need a relationship with someone who understands your situation—not just your numbers.

That relationship matters even more when things go wrong.

From his time at the IRS, Gabe is blunt: when audits happen, it’s the taxpayer who’s on the hook—not the preparer. He rarely went after accountants. The responsibility lands squarely on the individual or business owner. That’s why understanding your risk, your options, and the tradeoffs being made on your behalf is non-negotiable.

You can’t outsource accountability.

A strong tax relationship looks simple, but it’s increasingly rare. You should be able to pick up the phone. You should speak the same language. Your advisor should explain what’s happening, not just tell you what to file. They should have good bedside manner—and real dedication to your outcomes.

That human connection is how taxes are minimized responsibly, benefits are maximized intelligently, and long-term plans actually hold up under scrutiny.

IN CLOSING

In an industry racing toward scale, speed, and automation, Gabe’s message is quietly radical: relationships aren’t a soft skill in tax—they’re the foundation. And for clients who want to thrive, not just comply, choosing the right relationship may be the most important tax decision they make.

In an industry racing toward scale, speed, and automation, Gabe’s message is quietly radical: relationships aren’t a soft skill in tax—they’re the foundation. And for clients who want to thrive, not just comply, choosing the right relationship may be the most important tax decision they make.