What if tax season didn’t feel like a surprise bill you just accept … but a strategy you run on purpose?
On this episode of “The Sidekick Life,” Ryan and Tyler sit down with Matt Bontrager, founder and CEO of TrueBooks, to talk about what most high earners get wrong about taxes – and how to legally keep more of what you make.
This isn’t about gimmicks, loopholes or shady write-offs. It’s about understanding the rules, using them intentionally and building a plan that matches your goals.
“TrueBooks is my baby … we focus on tax and accounting for specifically real estate investors and business owners,” Matt said.
Most people treat taxes like something that happens to them. Matt says that’s exactly the problem.
“Tax to most people is like this black box … they don’t know what it is.”
And if you’re a W-2 employee with standard forms, that’s often fine, tools like TurboTax can work.
But everything changes when you cross into business ownership or real estate investing.
“I’m a fan of getting a CPA involved once you either run a business or have a rental property,” Matt said. “Once you have to tell the IRS what your income and expenses were.”
That’s when “filing” becomes “strategy.”
This is the part nobody wants to hear … because it’s not sexy. But it’s the foundation of everything. Matt doesn’t just like clean books, he’s borderline obsessed.
“One of the most slept-on things … is good bookkeeping.”
He explains that messy books don’t just cost you time, they cost you opportunities.
Good numbers let you:
“If you come to us with messy numbers … now your bill’s higher because I need my accountants on the back end to go do the work,” Matt said.
But what if you’re a high-income W-2 earner? Are you just stuck paying a massive tax bill?
Matt breaks it into three “phases” of tax strategy:
Matt explains why side businesses can create legit deductions, when they’re real businesses.
“There is this beautiful bridge … between being able to write off things that you’re involved in in your lifestyle with your business now.”
For example, if you start a photography business, the camera might become partially or fully deductible, depending on business vs personal use.
But he also explains why this usually won’t dent a huge W-2 income in a meaningful way. The deduction is limited to what you actually spend, and small businesses often create smaller losses.
This means it can help … but it won’t move the needle like bigger asset plays can.
Now, how can this help those who buy a franchise?
Matt breaks down what happens when you invest in something like a brick-and-mortar concept (golf simulators for example).
Many business assets can qualify for accelerated depreciation (depending on rules and asset life), and that can create a large paper loss up front.
“All of the smaller assets … most of those … are going to have lives that are 20 years or less … you can potentially bonus depreciate that and suck that forward.”
This means a franchise buildout can create a deduction large enough to significantly reduce taxable income, especially for high earners, if done correctly and planned in time.
But as Ryan points out, people often wait too long. If you’re trying to offset this year’s taxes, you can’t start planning in December.
Matt doesn’t trash the old model, but he explains why it frustrates clients.
The classic CPA relationship is transactional:
Matt says many clients assume their CPA is thinking about tax strategies all year … but that’s not how most firms are built.
“That firm was built on a transactional relationship.”
TrueBooks aims for something different with compliance, planning and accounting, with planning as the real value driver.
Matt also points out the profession is changing fast.
“70% of CPAs are set to retire in the next 10 years … we’re seeing very low growth as far as students coming into the profession.”
So, the firms of the future will likely be more virtual, specialized, proactive and premium.
Tyler highlights something unique TrueBooks offers: community and office hours.
Matt explains that this model gives newer business owners access to high-quality guidance without paying big-ticket planning fees they don’t need yet.
“Most of the market does not need a tax person where their fee should be five to 15 grand. What you do need is a one-time upfront quick call … and then that one-to-many help.”
It’s a smart blend of access, affordability and expertise without forcing people into the wrong tier.
If you remember nothing else, remember this:
Franchise ownership isn’t just about income. It can also be about control, strategy and keeping more of what you earn. Talk with a Sidekick Advisor to explore business models that fit your goals (including timing, investment level and yes, tax strategy)