Empowering Healthy Business Podcast Episode 55 : What Your CPA Should Be Telling You (But Maybe Isn’t) — with Greg Reed
Most business owners only talk to their CPA when they have to.
Tax season hits, you gather documents, you answer a few questions, and you hope the return gets filed on time. If you’re lucky, you get a refund. If you’re not, you get a tax bill that hurts.
In this episode of the Empowering Healthy Business Podcast, Cal Wilder sits down with Greg Reed to talk about what your CPA should be telling you—especially if you want fewer surprises and better decisions throughout the year.
To be fair, this isn’t about blaming CPAs. Greg explains that the tax system and the business model behind tax prep pushes most firms to be reactive. During tax season, many CPAs are in “factory mode,” trying to get returns done. That’s why the most important conversations often never happen.
Here’s what Greg says you should be hearing (and asking) from your CPA.
Tax prep isn’t the same as tax planning
A CPA can be fast and accurate at filing your return—and still not help you save money.
Greg points out a common pattern: clients say, “My CPA is great. My return is filed early.” But filing early is not the same thing as planning ahead. If your only conversation is once a year, you’re probably leaving money on the table.
Tax planning happens during the other nine or ten months of the year. That’s when you can actually make decisions that affect what you owe.
So if your CPA is only a once-a-year relationship, the real issue isn’t speed. It’s missed opportunities.
Not all tax savings are equal
Greg breaks tax savings into categories that most people never think about:
- Deductions reduce taxable income.
- Credits reduce your tax bill directly.
- Deferrals push taxes into the future.
Why does that matter?
Because a lot of “advice” business owners hear is really just deferral advice.
For example, you’ve probably heard: “Go buy a truck before year-end.” Yes, spending money can lower taxable income. But it can also be a bad move if you’re only doing it for the write-off.
Cal says it clearly: you don’t want to spend a dollar just to save 30 or 40 cents. If it’s something you would buy anyway and you’re just moving the timing up, that can be fine. But if your CPA’s best idea is always “go spend money,” you should ask deeper questions.
Think in multi-year windows, not one tax year
One of the best points in this episode is simple: taxes should be managed over multiple years.
Greg explains that if you drop your income too low in one year by stacking deductions, you can accidentally raise your income too high the next year. That can push you into a higher tax bracket and cost you more overall.
What you want instead is income “smoothing”—keeping income more consistent year over year when possible.
This also connects to strategies like accelerated depreciation. Taking a huge deduction now may feel good, but it also means you have less deduction later. In some cases, that’s the right tradeoff. In others, it isn’t.
The takeaway is not “always minimize taxes this year.” The takeaway is “make choices that hold up over time.”
Sometimes you should pay more tax
This sounds backwards, but it’s real.
Greg and Cal talk about a situation that surprises a lot of owners: when you need funding. Banks often want to see strong income on tax returns. A “juicy” tax return helps you look stable and profitable.
If you’re planning to grow aggressively and apply for loans, showing higher income may help you get approved. That can mean paying more tax. Greg calls it the cost of doing business sometimes.
And this is exactly the kind of conversation business owners miss when tax prep is the only focus.
Owner pay and entity structure need regular review
Greg says there are two conversations that should happen at least annually:
- Owner compensation
- Entity structure
These are not “set it and forget it” decisions.
As your business grows, your goals change. Tax laws change too. That can shift what makes sense.
Greg shares that he’s currently running multiple “S-corp vs C-corp” analyses for clients. Some were advised years ago to go the S-corp route, and now the answer may be different based on where the company is financially and what the owner wants next.
He also explains why owner pay matters. A common S-corp approach is to pay yourself less in wages and more through distributions. But if your goal is retirement planning, that might not be ideal, because many retirement plan contribution limits depend on wages.
So the “best” strategy depends on your priorities. And your CPA should be aligning tax strategy with your real goals, not just reducing the current tax bill.
Extensions aren’t a strategy
This part is blunt—and helpful.
Greg says if your CPA ever tells you that an extension is a “tax strategy,” it’s probably not true.
An extension is an extension to file, not an extension to pay. You still need to pay what you owe (or at least most of it) by the deadline.
Greg does recommend extensions in certain cases, like complex returns or when you’re waiting on key information. But he also makes an important point: it’s hard to do strategy when everything is historical. Filing late doesn’t create new opportunities by itself.
Even if you extend, you should still be planning for the current year. If it’s June and last year’s return isn’t filed yet, you should still be meeting to discuss Q2 estimates and planning.
Safe harbor estimates are “safe,” but they can still cost you
Greg and Cal discuss a common approach: paying “safe harbor” estimates based on last year.
That can protect you from penalties. But it can also cause a different problem: overpaying.
If your income changes a lot year to year, safe harbor payments may not match what’s actually happening now. And if you’re growing, you don’t want the IRS holding your cash for the next 12 months like an interest-free savings account.
That’s why Greg prefers talking with clients a few times a year, so estimates match the real year, not last year’s numbers.
He gives a clear example: a client who went from about $400K of net income to about $1.5M the next year. If they paid estimates based on the prior year, the tax bill would be brutal.
Tax planning has to be a two-way street
One of the most practical parts of the episode is this reminder:
Your CPA can only help with what they know.
Greg says he often finds out during tax season that a client started a new business, sold a business, got married, had a child, or made another major change. Those events can affect taxes in a big way, but only if your CPA knows early enough to plan around them.
He encourages quick check-ins. Sometimes it’s just a short message: “This happened—do I need to think about anything?”
That small habit is what separates clean, predictable tax seasons from stressful ones.
Be careful with “no tax” advice you see online
Greg says something refreshing: most of his clients use a few consistent, proven planning moves. They’re effective, they’re documentable, and they’re not flashy.
Cal adds a hard truth: he’s been a business owner for 25 years and has never found a legal way to avoid taxes completely. If someone on TikTok says “pay no tax,” you should question it.
In tax planning, boring is often good.
Conclusion: the conversation shouldn’t start and end in February
If you’re only talking to your CPA during tax season, you’re probably getting tax filing, not tax strategy.
Greg’s advice is simple:
- Talk to your CPA multiple times a year.
- Ask about multi-year planning, not just this year.
- Review structure and owner pay regularly.
- Don’t assume your CPA knows what changed in your life or business—tell them.
- Book planning conversations while you’re filing, so they’re already on the calendar.
You don’t need constant meetings. You just need the right touchpoints at the right times—so tax season becomes a smooth process, not a stressful surprise.
Want to go deeper? Listen to the full conversation on the Empowering Healthy Business Podcast