How to Stop Overpaying Taxes with Chris Shockowitz
Release Date: 12/02/2025
How to Stop Overpaying Taxes with Chris Shockowitz
Breakaway Wealth Podcast
Most business owners, investors, and high-income earners are losing money—not because they’re bad at making it, but because they’re bad at keeping it. In this episode, Jim sits down with tax strategist Chris Shockowitz of deferTax.com, a guy who walked away from corporate America, saved seven figures in taxes himself, and now helps entrepreneurs slash tax bills the legal, intelligent way. If you’ve ever wondered why the wealthy pay less tax, how they use the code instead of getting crushed by it, or how to stop being at the mercy of your CPA once a year…this conversation is...
info_outline
10 Success Habits of Top Performers with Jim Oliver
Breakaway Wealth Podcast
In this episode of Breakaway Wealth, Jim breaks down 10 universal success habits every top performer uses—whether they realize it or not. From structured mornings to time blocking, from health optimization to rapid-fire execution, these habits create predictable momentum. And when paired with Infinite Banking, they become a wealth engine on purpose. Jim also answers a pressing IBC question from the community: Can you run all of your W-2 income through your own banking system? Yes—but there’s a smarter way to approach it if your goal is velocity, not theory. It’s not motivation that...
info_outline
Vision, Chaos, and Calling Out Your Own BS with Adrian Koehler
Breakaway Wealth Podcast
In this episode of Breakaway Wealth, Jim Oliver sits down with leadership coach Adrian Koehler—a former pastor and prison leadership trainer who now coaches founders and “type A dickheads” who feel the weight of responsibility and the loneliness at the top. Adrian and Jim dig into why “not having a vision” isn’t an accident, it’s a strategy. They unpack how confusion is actually a chosen vision, why high-performers secretly love being “stuck,” and how most leaders waste energy being frustrated that others aren’t like them instead of learning to translate their own genius....
info_outline
The Illusion of Wealth: Why People Stay Broke with Jim Oliver
Breakaway Wealth Podcast
In this solo episode of Breakaway Wealth, Jim Oliver dismantles one of the biggest lies in finance: that income equals wealth. He shares hard-earned lessons from his early career in financial planning, where assets measured success under management—not freedom. Jim reveals how even six-, seven-, and eight-figure earners often remain financially enslaved. If your wealth disappears when your income stops, you don’t own your wealth; you lease it. Jim explains how to reclaim ownership by shifting your focus from income to control, and how he applies this mindset in building companies, creating...
info_outline
Relationship Intelligence: The Million-Dollar Skill with Dr. Erin Wilson
Breakaway Wealth Podcast
In this episode of Breakaway Wealth, Jim Oliver sits down with Dr. Erin Wilson, a powerhouse in leadership development and the creator of the “NAP Framework” for strategic rest. Together, they unpack relationship intelligence—the “million-dollar skill” that separates effective leaders from forgettable ones—and why rest is not a reward, but a strategy. Dr. Wilson shares how leaders can use relationship intelligence to connect, communicate, and collaborate at a higher level by understanding what truly motivates people. She also discusses her framework for strategic rest, how to use...
info_outline
The Massive Power In Radical Incrementalism with Dr. John Oberg
Breakaway Wealth Podcast
In this episode of Breakaway Wealth, host Jim Oliver sits down with Dr. John Oberg, founder of Priscina Health, a behavior expert, and a healthcare innovator, to explore the direct link between health and wealth. Dr. Oberg’s mission is to help people take back control — of their bodies, their decisions, and their outcomes — through a philosophy he calls “radical incrementalism.” Together, they unpack how small, sustainable habits compound into life-changing results — in fitness, finances, and freedom. From reversing Type 2 diabetes to understanding your “why,” Dr. Oberg’s...
info_outline
Legacy Over Luxury: How Tim Rexius Scales 5 Companies—and 6 Kids
Breakaway Wealth Podcast
Jim sits down with Tim Rexius — Omaha entrepreneur, fitness pro, and founder of Rexius Nutrition and Omaha Protein Popcorn — to talk about scaling life without losing your soul. From bodybuilding stages to global brands in 14 countries, Tim’s story is proof that discipline, faith, and energy compound across every area of life. He’s a father of six, a business owner of five, and a living example of legacy over luxury. Together, Jim and Tim unpack how health drives wealth, how mentorship multiplies impact, and how faith anchors it all. What You’ll Learn: The mindset shift: Balance...
info_outline
When the Headlines Scream No: Finding Hidden Yield with Tom Dunkel
Breakaway Wealth Podcast
In this episode, Jim brings on Tom Dunkel, founder of Eagle Capital Investments, co-founder of U.S. Mortgage Resolution (11k+ loans transacted), real-estate investor, and author of The Wealth Builders Playbook. Tom left the “corporate penitentiary,” got bloodied in ’08, then built durable wealth across distressed mortgage debt, self-storage, STRs, and a fund-of-funds platform. They break down why “now” is always the right time if your horizon is long, how to own the paper when bricks are a pain, and how to evaluate deals with his SAFE method so you compound without blowing up....
info_outline
The Wealth Shift: From Chasing Money to Having It with Jim Oliver
Breakaway Wealth Podcast
In this solo episode, Jim Oliver breaks down the single mindset shift that separates the herd from the wealthy: move from trading time for money to owning the system. Drawing on his journey from poverty and a casket factory to acquiring 30+ companies, Jim shows why most retirement advice is just slavery with better branding—and how Infinite Banking, cash-flowing assets, and velocity turn your money into a perpetual Wealth Engine. What You’ll Learn Why chasing a 401(k) balance is “poverty with a brochure” (and how averages hide risk) The 3D view of money: cash flow, tax flow, and...
info_outline
Tax Flow, Not Just Cashflow: How to Exit Smart and Buy Back Time with Brett Swarts
Breakaway Wealth Podcast
Jim Oliver sits down with Brett Swarts to tackle the part of exiting most owners ignore until it’s painful: Taxes. Brett is the founder of Capital Gains Tax Solutions, a real estate broker and tax strategy specialist with deep expertise in Deferred Sales Trusts (DST), Delaware Statutory Trusts, and 1031 exchanges. He hosts the “Build It to Billions” and “Capital Gains Tax Solutions” podcasts. Together, Jim and Brett lay out how purpose-driven entrepreneurs can engineer an exit that prioritizes tax flow, converts to truly passive income, and preserves control and flexibility....
info_outlineMost business owners, investors, and high-income earners are losing money—not because they’re bad at making it, but because they’re bad at keeping it.
In this episode, Jim sits down with tax strategist Chris Shockowitz of deferTax.com, a guy who walked away from corporate America, saved seven figures in taxes himself, and now helps entrepreneurs slash tax bills the legal, intelligent way.
If you’ve ever wondered why the wealthy pay less tax, how they use the code instead of getting crushed by it, or how to stop being at the mercy of your CPA once a year…this conversation is your wake-up call. Owners don’t play defense—they plan..
What You’ll Learn
-
Why does tax preparation cost you money, but tax planning saves you money
-
The difference between a CPA who reports history vs. a strategist who shapes your future
-
How high-income earners legally cut taxes by up to 50%
-
How to use trusts and smart structuring to sell crypto, real estate, or a business with zero tax
-
Why the tax code rewards investors, owners, and producers—and how to start thinking like one
Here’s the shift Chris drove home: Tax preparation reports history. Tax planning changes your future.
Your CPA can tell you what you owe. A strategist tells you what’s possible.
And most high-income earners are leaving six figures (or more) on the table simply because nobody ever showed them the legal, proven tools built into the tax code for people who invest, own, and think differently.
Chris’s Shared Wisdom
“Most people don’t know what they don’t know. The tax code isn’t built to punish you—it’s built to reward the people who invest in America. When you understand it, it changes everything.”
Connect with Chris:
Website: www.DeferTax.com
Linkedin: www.linkedin.com/in/christopher-shockowitz/