Ready or not, tax season is here.
Some of you are gathering documents and scheduling appointments. Others have already filed extensions and won’t think about this again until the fall.
But whether you’re filing this month or in October, there’s a question many people don’t bother to ask:
Is your CPA just processing your return, or are they actually working for you?
What Tax Time Should Look Like
If the interactions with your CPA resemble:
Upload documents
Get return back
Approve
File
…that’s compliance. Not strategy.
A real tax strategist uses this year’s filing as the starting point for next year. They look at your 2025 return and ask: ”what do we want this to look like next year? What can you start doing now?”
Filing your return should be the beginning of next year’s plan, not the end of the conversation.
The Questions They Should Be Asking You
A good way of knowing if your CPA is strategic is if they’re asking you questions, not just answering yours.
A good strategy-oriented CPA sees your K-1s from syndications and asks how you want to handle depreciation going forward. They see W-2 income and ask whether you’ve considered strategies to offset it. They notice a property sale and ask whether you’ve thought about a 1031...before you sell the next one.
If you’re investing in real estate and your CPA has never proactively brought up things like:
Cost segregation
Bonus depreciation
Real estate professional status…
Or worse, if they’ve told you those things are “risky”…
They’re a glorified form-filer, not a strategy-builder.
The Real Cost of Staying Put
The difference between compliance and strategy can be enormous.
Take real estate investor and syndicator Brad Sumrok, for example. He used to brag about paying seven figures in taxes because he thought it was a proxy for his income. Then CPA Tom Wheelwright pulled him aside and told him that was dumb and since he was in real estate, he shouldn’t be paying any.
Brad now brags of a multi-year streak of owing $0 in federal income taxes.
Most CPAs are excellent at compliance. They make sure your numbers are correct and your return gets filed on time. But once your financial life becomes more complex than a couple of W-2s and some 1099s, you need someone who can do strategy, not just data entry.
You probably outgrew your CPA the moment you started investing in syndications. It’s unfortunate, but the person who handled your simple tax return for years is not necessarily equipped for K-1s, passive loss limitations, and wealth preservation planning.
What to Do About It
If the annual ritual of talking to your CPA feels more like a drop-off at H&R Block, that’s a strong signal that it’s time for a change.
You don’t need to fire anyone today. After all, it’s too late to change anything about last year. But you owe it to yourself to have a conversation with a CPA who specializes in real estate, syndications, and investor tax strategy to start your plan for 2026.
Look for someone who can answer strategy questions, has worked extensively with accredited investors, and collaborates well with your other advisors.
Your CPA is one of the most important members of your wealth-building team. And the difference between a compliance CPA and a strategic advisor shouldn’t be thought of as an unnecessary luxury – it’s a wealth multiplier.
If you want to go deeper on tax planning strategies, Adam and I cover this in Wealth Independence Podcast episode v1.41. We talk about short-term rental strategies, oil and gas deductions, and how we structure our tax planning throughout the year. Watch/listen here.