EP 151: Smarter Tax Strategy for Real Estate & Crypto Investors – with Zach Gordon
Release Date: 06/11/2025
EP 169: The 5 Hidden Risk Factors That Crush Real Estate Fortunes
Unlock Your Life
In this week's episode of Unlock Your Life, Jennings breaks down the five critical risk factors every real estate investor must know. Drawing from personal experience, Jennings explains why failure is a better teacher than success and how overconfidence can lead to heartbreak. He methodically explores why investing out-of-market, purchasing older buildings, ignoring location fundamentals, venturing into unfamiliar asset classes, and taking on too many deals simultaneously can devastate your portfolio. This episode delivers a masterclass in risk management and emphasizes that operational...
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EP 168: Money Wounds: How Your Past Shapes Your Finances with Shannon Ryan
Unlock Your Life
In this week's episode, Jennings sits down with financial advisor and author Shannon Ryan to explore the psychology of money. Shannon reveals how our emotional "money wounds" shape financial decisions and why confidence with money isn't about your net worth; it's about aligning finances with your values. Discover why we keep "moving the goalposts" of financial security, how to have honest money conversations with your partner, and practical strategies for breaking free from limiting money beliefs. Shannon shares wisdom on building cash reserves, especially with irregular income, and finding...
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EP 167: No Investors Needed: How to Own 100% of Your Real Estate Deals
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In this week's episode, discover a game-changing real estate investment strategy that eliminates the need to raise capital or dilute equity. You'll learn how to leverage seller financing in today's market conditions, where prices remain high despite rising interest rates, creating perfect opportunities for creative deals. Jennings breaks down exactly how to find ideal sellers, structure attractive offers, and solve the three critical problems in every seller-financed transaction. Plus, get insights on debt serviceability, value-add opportunities for refinancing, and an invitation to access...
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EP 166: Inside Grant Cardone's Real Estate Investment Strategy with Chris Skinner
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In this week's episode, Jennings interviews Chris Skinner, a seasoned real estate investor and tax strategist. Chris shares his remarkable journey from a 30-year sales career to becoming a successful real estate investor. After experiencing setbacks during the 2008 housing crash, Chris discovered the power of cost segregation and other tax strategies that the wealthy use to build and preserve wealth. The conversation dives into Chris's recent investments, including a 72-unit property in Panama City and his experience investing with Grant Cardone's real estate fund. Chris offers...
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EP 165: Billionaire Secrets: Interviewing an Advisor to the Most Powerful Families in the World
Unlock Your Life
In this episode of Unlock Your Life, Jennings sits down with Richard Wilson, founder of Family Office Clubs, who shares his expertise on building meaningful relationships with high-net-worth investors. Wilson reveals why community building trumps transactional approaches, emphasizing that trust developed over time is the foundation for successful deals. He breaks down his practical three-part strategy for capital raising: crafting a compelling one-liner, creating a concise video pitch, and developing a powerful one-page document. The conversation explores Wilson's innovative AI platform, which...
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EP 164: The Way This Deal Was Structured Changed His Whole Life
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This episode dives into one incredible transformative real estate deal: an innovative 103-unit motel-to-apartment conversion with creative zero-interest financing. Learn how this deal was structured to minimize risk while maximizing returns, and discover the strategies that can help you identify similar opportunities in today's market. Also, Jennings provides an update on his ongoing flex warehouse project that successfully raised $1.5M with a 12% guaranteed return on investment. If you're looking for some inspiration on creative financing, you don't want to miss...
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EP 163: He Told Me To Sell-Not Hold: Advice From A Billionaire
Unlock Your Life
In this week's episode, Jennings dives into smart real estate investment strategy beyond the typical "buy and hold" approach. He breaks down the three essential income buckets every investor needs: immediate cash for bills, mid-term income for reinvestment, and long-term passive income for retirement. Jennings shares a cautionary tale about a property where doubling insurance costs decimated cash flow, and reveals crucial advice from a billionaire investor about establishing "bomb-proof" passive income before taking bigger risks. Learn why liquidity might be your...
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EP 162: Why People Are Quitting Real Estate Now More Than Ever
Unlock Your Life
Let's be real- it's a tough real estate landscape right now. We've seen people leaving real estate, struggling to keep money in the bank, pay investors/lenders, etc. But we've seen good times, bad times, bubbles, and corrections, and real estate is all about the long game! 3 things from this episode: 1. If you’re still in the real estate game, or have expanded during difficult seasons, hats off to you! 2. If you’re newer and you're hanging in there now, you may not even know what the great times are like. So keep going! 3. If you’ve given up, let it be for a season. There’s always time...
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EP 161: Find Your Motivation
Unlock Your Life
Do you find yourself struggling to find motivation? Do you see others who appear to be insanely disciplined and ask yourself, "What is their secret to success?" On today's episode, we look at the mindset with which we approach things like discipline, laziness, and motivation. Maybe you're not actually lazy or lacking motivation and discipline! Maybe you've allowed yourself to focus on the stress/obstacle of the cost instead of letting yourself be driven and inspired by the outcome! This mindset shift has helped others step off the struggle bus and start making meaningful moves in their lives...
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EP 160: Getting Started In Real Estate (with Ben Gammon)
Unlock Your Life
In this week's episode, Jennings is joined by real estate investor Ben Gammon. Like many of you, Ben looked at his long term financial outlook and considered what his retirement would look like. He began asking himself if he would be financially ready to retire when the time came. With a background in property management, Ben saw others realizing the financial goals he had for himself in the world of real estate investment. This began the journey that would eventually lead Ben into full time real estate. In this episode, Ben shares insights into how he made this transition, pitfalls he...
info_outlineIn this episode of Unlock Your Life, Jennings sits down with Zach Gordon, co-founder of Forward- a CPA firm tailored for real estate professionals, crypto investors, and high-growth entrepreneurs.
Zach shares actionable insights on minimizing tax liability, the pros and cons of cost segregation, and how to avoid massive depreciation recapture surprises. They also explore crypto tax strategy, entity structure best practices, and why traditional CPA firms are failing today’s investors.
If you're building wealth through real estate or digital assets, this conversation is packed with practical advice to help you stay compliant, strategic, and ahead of the game.
Thanks for listening!