My grandparents are attorneys who fix the mess I make of my finances. It made me realize how much most people overpay in taxes.
Let me start with two questions, because they're what got me thinking about all this…
Do your coworkers or business colleagues make the same as you, or more, but somehow pay less in taxes, or even get a refund? And do you actually feel like your CPA or tax preparer is getting you every deduction you're entitled to, or just filing what you hand them?
Here's my situation. I'm fortunate that my grandparents are attorneys, and they oversee my taxes. I'll be honest about why I need them. I’ve spent money recklessly. Dinners, clothes, nights out, trips, vehicles, gifts, etc… I've run business expenses out of my personal account and personal expenses out of my business account. I've had vehicles titled personally but used for the business. I've moved money in and out of my own company in ways that would make any normal preparer's head spin. I've genuinely made my finances about as tangled as a person can.
And every year, my grandparents sort through the chaos, classify everything correctly, and somehow I end up with a federal refund that usually covers whatever I owe at the state level. From a situation I actively sabotaged.
That's what got me. If someone can untangle the disaster I create and still get me a good outcome, then people with normal, clean finances are almost certainly leaving money on the table just because nobody's looking closely.
I started asking friends about it. Freelancers, small business owners, people with side hustles. Over and over I heard "my CPA just files what I give them." No strategy. No proactive questions. A few of them let my grandparents take a look, and the difference was real. Not magic, just someone actually examining the whole situation. Depreciation they were ignoring, charitable giving structured the worst possible way, credits they'd never heard of, retirement contributions that didn't fit their income.
So I built something around it. It's called Tax IQ. You answer a detailed questionnaire about your situation and it generates a strategy document. Specific strategies that apply to you, the rough math, and what to bring to your CPA. The point is to walk into your tax conversation prepared instead of hoping your preparer digs.
Mostly I'm curious whether this resonates with anyone or if I'm in a bubble. For those of you self-employed or running a business, does your CPA actually do proactive strategy, or is it mostly filing what you hand them?
Happy to share the link to anyone wanting to take a poke at it.