CreateTailwind

Breakaway Wealth Podcast

Business EN ↓ 200 episodes

Building wealth isn't just about hustle and grind. Every day, huge deals are being made, businesses and properties are changing hands, and a small group of people are making quantum leaps forward - building wealth faster than most dream possible. To the rest of the world, it looks like they have the Midas Touch. What makes them different? They chose to break AWAY. To build a mindset of abundance. To spot opportunities others overlook. On this podcast, we'll unlock the secrets to breaking out of the herd, thinking BIG and building wealth on our own terms.

Author

CreateTailwind

Category

Business

Podcast website

createtailwind.com

Latest episode

Jul 7, 2026

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Episodes

Design Your Life So Success Is Automatic with Jim 30.12.2025

Most people think they fail because they lack discipline. That is false. They fail because their environment is perfectly designed to pull them off course. In this episode, Jim breaks down why willpower always loses, how default settings quietly dictate outcomes, and why 2026 must be engineered, not hoped for. If you want success to feel automatic instead of exhausting, this episode gives you the...

The Furnace: Building Your Capacity for 2026 with Jim Oliver 23.12.2025

Everybody wants bigger results in 2026—more money, more freedom, more impact. Almost nobody wants the pressure that actually builds the capacity to handle it. In this episode, Jim breaks down the "furnace" moments of life—those seasons of heat, friction, and resistance—and shows how they're not punishment, they're training. Capacity, not talent, is what 2026 will reward. Using the S.A.I.D. princip...

2026 Starts with Identity: How to Have Your Best Year with Jim Oliver 16.12.2025

In this solo episode, Jim resets the 2026 "best year ever" series and takes you back to the real starting line: identity. This isn't motivation, resolutions, or another empty goal-setting rant. This is a structured, identity-driven blueprint to architect a year you actually control instead of replaying 2025 with a new calendar. Jim breaks down why you don't get what you want—you get what you're bu...

Design Your Inner Operating System for an Unstoppable 2026 with Jim Oliver 09.12.2025

Most people are trying to "goal" their way into a better year. They set resolutions, white-knuckle new habits, and wonder why everything falls apart by March. In this episode, Jim breaks that pattern wide open. 2026 won't rise to the level of your goals. It will fall to the level of your systems—and your systems are built on identity, energy, and emotional mastery. Jim walks you through how elite...

How to Stop Overpaying Taxes with Chris Shockowitz 02.12.2025

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'...

10 Success Habits of Top Performers with Jim Oliver 25.11.2025

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 th...

Vision, Chaos, and Calling Out Your Own BS with Adrian Koehler 18.11.2025

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, w...

The Illusion of Wealth: Why People Stay Broke with Jim Oliver 11.11.2025

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...

Relationship Intelligence: The Million-Dollar Skill with Dr. Erin Wilson 04.11.2025

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 relation...

The Massive Power In Radical Incrementalism with Dr. John Oberg 28.10.2025

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 unp...

Legacy Over Luxury: How Tim Rexius Scales 5 Companies—and 6 Kids 21.10.2025

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...

When the Headlines Scream No: Finding Hidden Yield with Tom Dunkel 14.10.2025

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...

The Wealth Shift: From Chasing Money to Having It with Jim Oliver 07.10.2025

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 mone...

Tax Flow, Not Just Cashflow: How to Exit Smart and Buy Back Time with Brett Swarts 30.09.2025

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.  Tog...

Do Hard Things: Discipline, Cashflow, and AI with Mark Young 23.09.2025

Most people wait for perfect conditions and call it "planning." That's just stuck.  In this conversation, Mark Young, an entrepreneur, educator, author, and functional doctor, joins Jim to break the addiction to comfort, reframe failure, and get back to ownership. We hit health, wealth, and work: why public goals matter, why cashflow beats accumulation, and how to use AI as a collaborator (not a c...

How to Activate Your Network and Make Money with Jarrod Randolph 16.09.2025

In this episode, Jim sits down with real estate pro turned relationship operator, Jarrod Guy Randolph. They talk straight about access to wealth and why your phone is a graveyard of unrealized capital. They break down Jarrod's "Buying Favor" operating system, the FAVOR network map, why most masterminds are wasting time, and how humility beats ego when you're leveling up. What You'll Learn Why the...

Purpose Before Progress with Pankaj Singh 09.09.2025

In this Breakaway Wealth episode, Jim digs in with leadership coach Pankaj Singh on how purpose, clarity, and simple mindful practices make you a sharper leader at home and at work. We get practical—how to carve purpose, build the right relationships, run cleaner meetings, and reset your brain in 60 seconds.  Who is Pankaj? He's the founder of Singh Leadership, creator of the Inner Compass Journey...

The Science of Getting Rich with Jim Oliver 02.09.2025

In this solo episode, Jim breaks down the timeless principles from Wallace D. Wattles' 1910 classic, The Science of Getting Rich. But this isn't a book report—it's a powerful call to action for anyone who's ready to stop playing small, stop competing, and start creating real wealth, legacy, and impact. In true Jim fashion, this episode is raw, faith-tinged, and energized. Whether you're stuck in s...

How AI Can Power Your Business with Blair Gatchel 26.08.2025

In this episode of Breakaway Wealth, Jim is joined by Blair Gatchell of Breva.ai to discuss how business owners can use artificial intelligence to make better acquisition and management decisions. They examine how replacing gut instinct with real-time analytics can reduce risk, improve cash flow, and create a sustainable framework for growth. 3 Key Takeaways: The Value of a Defined Process – A cle...

The Science of Bravery: Overcoming Fear with Jill Schulman 19.08.2025

In this episode of Breakaway Wealth Podcast, Jim sits down with Jill Schulman—US Marine veteran and positive psychology expert—to break down the science of bravery and why action - not motivation - moves outcomes. They map a practical path to confront fear, build daily reps, and apply courage to business and money decisions. 3 Key Takeaways: Bravery reframed: not heroics, but voluntary action in t...

Break the Rules to Build Your Wealth with Chris Prefontaine 12.08.2025

In this episode, Jim welcomes the extraordinary Chris Prefontaine, founder of Smart Real Estate Coach, for a deep dive into the mindset, structure, and discipline required to build financial freedom through creative real estate investing. Prefontaine shares lessons from the 2008 crash, explains why coaching matters, and offers practical pathways for people looking to break free from traditional fi...

What Really Drives Returns in Private Real Estate with Jacob Vanderslice 05.08.2025

In a market flooded with pitch decks and pro forma promises, what actually drives durable returns in private real estate?  In this episode, Jim sits down with Jacob Vanderslice of VanWest Partners to dissect the operational backbone of self-storage, the risks behind the spreadsheets, and why real investors focus on downside protection more than projected upside. Key Takeaways: Self-storage is an o...

Inside the Minds of Multi-Millionaires: Wealth, Legacy, and Risk in 2025 with Tad Fallows 29.07.2025

In this episode of Breakaway Wealth, Jim speaks with Tad Fallows, entrepreneur and founder of Long Angle, a private community for individuals with $2.2M+ in investable assets. They discuss how wealth creators think about investing, raising children without entitlement, and maintaining purpose after a business exit. 3 Key Takeaways: Portfolio strategy beyond Wall Street: High-net-worth individuals...

Scarcity to Control: The Mindset Shift Behind Financial Freedom with Jim Oliver 22.07.2025

In this episode, Jim walks through the shift that changed everything: from chasing returns to building freedom through ownership and control. He shares the early lessons—from a casket factory in Gary, Indiana to Wall Street boardrooms—that forced him to question the financial playbook most people follow. The real breakthrough? Understanding that freedom isn't about having more—it's about controlli...

Why Strategic Metals Are the New Oil with Louis O'Connor 15.07.2025

In this episode, Jim talks with Louis O'Connor, founder of Strategic Metals Invest, about a little-known asset class that's playing an outsized role in energy, defense, and global manufacturing: rare earth and strategic metals. Louis breaks down how investors can position themselves ahead of the demand curve—and why most people have never heard of these assets. 3 Key Takeaways: Critical inputs, li...

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