---
title: How to Not Pay Your Taxes Legally | Franchise Sidekick
description: CPA Matt Bontrager explains how high earners legally reduce taxes through business ownership, depreciation and proactive planning.
---

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# [How to Not Pay Your Taxes Legally | Franchise Sidekick](https://www.franchisesidekick.com/resources/podcasts/episode-40)

 Written by [Tyler Altenhofen | Ryan Zink](https://www.franchisesidekick.com/resources/podcasts/author/ryan-zink-tyler-altenhofen) | Mar 4, 2026 2:51:33 PM

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](https://truebookscpa.com/), 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.**

## The biggest misconception: Taxes feel like a “black box”

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.”

## The most underrated tax strategy: Good bookkeeping

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:

- Make better decisions in your business
- Spot profitability issues early
- Plan your tax strategy proactively
- Avoid paying your CPA to untangle a shoebox of receipts

**“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.**

## **W-2 high earners: What can you do *before* you buy a business**** **

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:**

1. **Reinvesting into the activity that creates the income. **But he also points out that W-2s can’t do any of that.
2. **Retirement accounts. **Not exciting, but powerful. **“It’s incredible to me to see how many people … have nothing in their retirement,” Matt said.**
3. **Real estate** **(especially where the rules allow it).** This is where TrueBooks runs fast, and where a lot of W-2 earners try to create legal offsets.

## **Write off your life (without doing anything stupid)**

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.

## **Why franchises can be a serious tax play**

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.

## **Traditional CPAs vs. strategy-first CPAs**

Matt doesn’t trash the old model, but he explains why it frustrates clients.

**The classic CPA relationship is transactional:**

- Drop off docs
- File return
- See you next year

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.

## **Community and office hours planning (a model more firms should copy)**

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.

## **Key takeaways**

**If you remember nothing else, remember this:**

- **Tax “filing” isn’t tax “strategy.”** If you want to pay less legally, you need proactive planning.
- **Bookkeeping is the backbone.** Clean numbers create real options.
- **W-2 earners have fewer levers, until they add ownership.** Business and real estate open up entirely different advantages.
- **Franchise ownership can create legitimate tax benefits** through depreciation and structured investments *but timing matters.*
- **The best advisors work as a team.** Ryan’s “survivor alliance” concept (CPA + financial advisor + attorney) is the cheat code for high performers.

## **If this episode hit home, this is your sign to stop winging it.**

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 ](https://www.franchisesidekick.com/schedule)to explore business models that fit your goals (including timing, investment level and yes, tax strategy)

[View full post](https://www.franchisesidekick.com/resources/podcasts/episode-40)

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