Trust This with Joseph Seagle

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Jun 2026

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I’m Joe Seagle, founder and CEO of Aspire Legal Solutions and My Land Trustee, the largest and fastest-growing land trust company in Florida. Our passion is helping people aspire to a better life. One of the many ways we do that is by helping them remain anonymous when it comes to their real estate holdings as they build their wealth. But it also extends to everyone else we touch each day. We’re fortunate to work with some of the most successful entrepreneurs in the country who share our mission of aspiring to a better life, and we hope others will benefit from hearing their journeys, tips, strategies, and tactics to get there. Thanks for listening to this edition of Trust This. If you got something out of it, please press like and subscribe and give us a five-star review to help us reach others who may benefit from this series.

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June 11, 20263 min

Florida Land Trusts and 1031 Exchanges: Understanding the Same Taxpayer Rule for Real Estate Investors

Are Florida Land Trusts compatible with a 1031 exchange? In many cases, yes—but maintaining tax-deferred treatment depends on understanding how the IRS applies the same-taxpayer rule and whether your trust structure is recognized as the same taxpayer throughout the transaction. In this episode of Trust This, Attorney Joe Seagle explores the relationship between Florida Land Trusts, 1031 exchanges, revocable trusts, irrevocable trusts, and Delaware Statutory Trusts (DSTs). He explains how the IRS evaluates different trust structures, why taxpayer classification matters, and how ownership changes between the sale and purchase of investment property can impact exchange eligibility. If you own rental property, investment real estate, or assets held in trusts and LLCs, this episode offers valuable guidance on avoiding common 1031 exchange pitfalls while maximizing asset protection and tax-deferral opportunities. Discover how trust-owned real estate is treated under IRS rules and what investors should consider before selling or exchanging a property. Download the Florida Land Trust 1031 Compatibility Guide to learn how different trust structures can affect your 1031 exchange strategy: https://aspirelegal.com/florida-land-trust-1031-compatibility-guide/ Looking to strengthen your asset protection plan? Contact Aspire Legal Solutions to learn more about Florida Land Trusts, estate planning, business structuring, and wealth preservation strategies. Schedule your complimentary Discovery Call today: https://aspirelegal.com/contact/ Chapters (00:00:00) - What Is the Same Taxpayer Rule under 1031?

June 4, 20261 hr 2 min

Ask Joe Live Q & A – Florida Land Trusts, LLCs, and Estate Plans

Ever wonder if the legal advice you're hearing online actually works in the real world? In this episode of Ask Joe Live, Attorney Joe Seagle answers real questions from investors, entrepreneurs, and families navigating everything from asset protection and Florida land trusts to LLC structuring, estate planning, and long-term wealth preservation. No scripts, no canned presentations—just practical answers to the questions people are asking right now. Joe shares insights from decades of experience helping clients protect assets, avoid probate, structure rental properties, maintain privacy, and build legal frameworks that support long-term growth. Along the way, he tackles common misconceptions, discusses real-world scenarios, and explains why some of the most effective strategies are often the simplest. Whether you're a seasoned real estate investor, a business owner looking to reduce risk, or someone who wants to create a stronger plan for the future, this conversation is packed with valuable takeaways. Tune in to hear Joe's candid perspective, learn from questions submitted by listeners, and discover strategies that could help you protect what you've worked so hard to build. Have a question you want answered on our next Ask Joe episode? Leave a comment below! Subscribe: Don’t miss out on future episodes of our Trust This podcast —subscribe now! https://www.youtube.com/@TrustThisTV Unlock the power of land trusts to protect your assets and enhance your privacy with Land Trusts in Florida, 11th Edition by experts Mark Warda and Joe Seagle—get your copy now! https://mylandtrustee.com/book/ Next Trust This Newsletter Alert: Stay tuned for more valuable tips and updates! https://trustthis.beehiiv.com/subscribe Protect what matters most—reach out today to explore our asset protection services, including estate planning, land trust creation, and business structuring. Book a Free Discovery Call today! https://aspirelegal.com/contact/ Chapters (00:00:01) - The podcast focuses on asset protection and estate planning issues for Florida investors(00:01:21) - Is There a Best Way to Do Estate Planning?(00:06:21) - Should I Put My Homestead in a Trust?(00:10:25) - Does a Land Trust Really Work?(00:16:14) - Does the Beneficiary Have a Right to Sign Leases and Applications(00:19:13) - Do you need a homestead exemption on your property?(00:23:31) - What About the HOA?(00:29:37) - How to Best Structure Rental Properties for Asset Protection(00:32:22) - What changes should be made to a single member LLC to provide better(00:36:39) - Does a Spouse or Adult Child Subsume as Additional Members(00:40:41) - Florida Land Trust(00:42:35) - Land Trust and Limited Liability Companies(00:47:02) - House Hacking and Co-Living(00:54:15) - Florida LLC Management Trust(00:57:58) - Can I Make a Homestead Property a Investment Property?(01:01:12) - A Day In the Life

May 28, 20269 min

Inside vs Outside Creditors Explained | Attorney Joe Seagle on Asset Protection

Attorney Joe Seagle explains the important difference between inside creditors and outside creditors in a clear, real-world discussion centered around asset protection strategies for business owners, professionals, and real estate investors. He walks through how inside creditors are connected to specific assets — such as mortgage lenders, tenants, contractors with liens, or banks with claims against accounts — while outside creditors are tied to personal liabilities like lawsuits, accidents, employment disputes, or other legal claims. Joe also shares how certain situations, like a foreclosure leading to a deficiency judgment, can turn an inside creditor into an outside creditor with the ability to pursue additional assets. Throughout the episode, Attorney Joe Seagle highlights how proactive asset protection planning can help reduce risk before legal or financial issues arise. He discusses the role of LLCs, land trusts, layered ownership structures, and privacy strategies designed to help safeguard wealth and limit creditor exposure. If you want to better understand how experienced asset protection attorneys structure plans to help protect long-term financial security, listen to the full episode now. Have a question you want answered on our next Ask Joe episode? Leave a comment below! Subscribe: Don’t miss out on future episodes of our Trust This podcast —subscribe now! https://www.youtube.com/@TrustThisTV Unlock the power of land trusts to protect your assets and enhance your privacy with Land Trusts in Florida, 11th Edition by experts Mark Warda and Joe Seagle—get your copy now! https://mylandtrustee.com/book/ Next Trust This Newsletter Alert: Stay tuned for more valuable tips and updates! https://trustthis.beehiiv.com/subscribe Protect what matters most—reach out today to explore our asset protection services, including estate planning, land trust creation, and business structuring. Book a Free Discovery Call today! https://aspirelegal.com/contact/ Chapters (00:00:00) - Inside creditors vs Outside creditors in asset protection

May 7, 202644 min

Wills vs. Trusts with Attorney Joe Seagle

What happens to everything you’ve built when you’re gone — and will your family be protected or stuck in probate court? In this episode of Trust This, Attorney Joseph E. Seagle breaks down the real differences between wills and trusts, why many estate plans fail when families need them most, and how proper planning can help protect your assets, business, and legacy. Drawing from more than 30 years of legal experience, Joe shares practical insights on probate, real estate, business succession, trustee selection, and strategies designed to keep your affairs private and your loved ones out of unnecessary legal battles. He also explains common mistakes people make with outdated plans, how trusts can protect heirs from creditors and poor financial decisions, and why flexibility is critical for long-term wealth preservation. Whether you’re a business owner, real estate investor, or simply want peace of mind for your family’s future, this episode delivers clear and actionable guidance. Listen to the full episode now and learn how to create a plan that protects what you’ve built for the next generation. Have a question you want answered on our next Ask Joe episode? Leave a comment below! Subscribe: Don’t miss out on future episodes of our Trust This podcast —subscribe now! https://www.youtube.com/@TrustThisTV Unlock the power of land trusts to protect your assets and enhance your privacy with Land Trusts in Florida, 11th Edition by experts Mark Warda and Joe Seagle—get your copy now! https://mylandtrustee.com/book/ Next Trust This Newsletter Alert: Stay tuned for more valuable tips and updates! https://trustthis.beehiiv.com/subscribe Protect what matters most—reach out today to explore our asset protection services, including estate planning, land trust creation, and business structuring. Book a Free Discovery Call today! https://aspirelegal.com/contact/ Chapters (00:00:00) - Wheels vs Truss(00:00:52) - Will vs. Trust: Estate Planning and Liability in Florida(00:04:46) - Will vs Trust: What's the Difference?(00:06:45) - Do Will and Probate Cases overlap?(00:13:17) - Florida probate: Will and Trust in Florida(00:21:10) - Will & Estate: Trust Protection vs Probate(00:30:08) - Should You Trust Your Own Money?(00:34:22) - Trusts and Estate Tax Planning(00:38:29) - Estate Tax and Long Term Care Planning

April 30, 202619 min

You WILL Get Sued… Here’s How Smart Investors Protect Their Assets

If you think asset protection means you’ll never get sued, think again. In this episode, Attorney Joe Seagle breaks down one of the biggest misconceptions in asset protection: there is no such thing as 100% protection from lawsuits. Instead of chasing a false sense of security, smart entrepreneurs and real estate investors focus on what actually works—layering strategies that make it difficult, expensive, and time-consuming for creditors to reach your assets. Inside this episode, you’ll learn: Why lawsuits are not a matter of if, but when for business owners and investors The difference between inside creditors vs. outside creditors How horizontal and vertical asset protection creates powerful legal barriers Why insurance alone is not enough to protect your wealth How tools like LLCs, land trusts, and entity structuring help “muddy the waters” Real-world scenarios (rental properties, accidents, business disputes) that put your assets at risk How proper structuring can give you leverage to settle lawsuits for less Whether you’re a real estate investor, entrepreneur, or business owner, understanding these strategies can mean the difference between losing everything—or protecting what you’ve built. The goal isn’t to avoid lawsuits. The goal is to make yourself hard to collect from. Have a question you want answered on a future Ask Joe episode? Reach out and let us know. Subscribe so you don’t miss future episodes of the Trust This podcast: https://www.youtube.com/@TrustThisTV Unlock the power of land trusts to protect your assets and enhance your privacy with Land Trusts in Florida, 11th Edition by Mark Warda and Joe Seagle: https://mylandtrustee.com/book/ Stay connected and get more insights from the Trust This newsletter: https://trustthis.beehiiv.com/subscribe Protect what matters most. Learn more about asset protection, estate planning, and business structuring: https://aspirelegal.com/contact/ Chapters (00:00:00) - Is Asset Protection Necessary?(00:10:55) - Married Couple: Multi-

April 23, 202631 min

Bitcoin Investing + Estate Planning: The Strategy Most Investors Overlook

What happens to your Bitcoin if something happens to you? In this episode, Asset Protection Attorney Joe Seagle sits down with Lindsay Faust of River.com to explore how Bitcoin fits into long-term wealth planning, estate strategy, and asset protection. Lindsay breaks down why River.com focuses exclusively on Bitcoin, emphasizing its decentralized structure, fixed supply of 21 million coins, and its track record as a resilient digital asset. The discussion also highlights how Bitcoin differs from traditional fiat currency, particularly in its resistance to inflation and centralized control. They walk through practical strategies for investors, including dollar-cost averaging, maintaining a long-term mindset, and avoiding emotional decisions in a volatile market. Lindsay explains how River simplifies the process with recurring purchases, zero-fee incentives, and tools designed to help investors stay consistent. A key part of the conversation focuses on estate planning—an area many Bitcoin holders overlook. Lindsay outlines how River supports trusts and LLCs, offering a streamlined onboarding experience, secure cold storage custody, and a clear path for transferring assets to beneficiaries. The episode also looks ahead at River’s broader vision, including “banking with Bitcoin,” where users can earn interest, pay bills, and even direct deposit income while continuing to build long-term holdings. If you are an investor, entrepreneur, or professional holding digital assets, this episode offers a practical look at how to protect and plan for the future. Connect with River.com: 614.381.4876 https://river.com Have a question you want answered on a future Ask Joe episode? Submit it and it may be featured. Subscribe to the Trust This podcast to stay up to date on future episodes. https://www.youtube.com/@TrustThisTV Learn more about protecting your assets with Land Trusts in Florida, 11th Edition by Mark Warda and Joe Seagle: https://mylandtrustee.com/book/ Stay connected with the Trust This newsletter for more insights and updates: https://trustthis.beehiiv.com/subscribe Protect what matters most. Explore asset protection services, including estate planning, land trust creation, and business structuring: https://aspirelegal.com/contact/

April 16, 202628 min

Seller Financing Secrets Every Seller Needs to Know (Before You Sign)

Selling your property and thinking about offering financing? That decision could either create long-term wealth or long-term headaches. In this episode, Attorney Joe Seagle pulls back the curtain on what really happens when sellers become the bank. He walks through how seller financing works, what terms truly matter, and why approaching the deal like a lender, not just a seller, can make all the difference. From setting the right interest rate and securing a solid down payment to properly vetting the buyer, Joe breaks down the key moves that separate smart deals from risky ones. He also highlights the often-overlooked dangers, including foreclosure delays, insurance gaps, and weak borrower protections. But it’s not all risk, seller financing can unlock major advantages, like consistent income, tax deferral, and even the ability to sell the note later for liquidity. If you’re considering seller financing, this episode delivers the clarity and strategy you need before putting pen to paper. Before you agree to any seller financing terms, make sure you’re structuring the deal the right way. Use our Free Seller Financing Evaluation Tool to quickly assess your deal, understand your risk, and see how your terms stack up.https://aspirelegal.com/seller-financing-evaluator/ Unlock the power of land trusts to protect your assets and enhance your privacy with Land Trusts in Florida, 11th Edition by experts Mark Warda and Joe Seagle—get your copy now! https://mylandtrustee.com/book/ Next Trust This Newsletter Alert: Stay tuned for more valuable tips and updates! https://trustthis.beehiiv.com/subscribe Protect what matters most—reach out today to explore our asset protection services, including estate planning, land trust creation, and business structuring. Book a Free Discovery Call today! https://aspirelegal.com/contact/

March 26, 202635 min

FinCEN's Ruling Blocked: What Does It Mean?

FinCEN just dropped new guidance on the real estate reporting rule—and it’s raising more questions than answers. In this quick update, we break down what’s actually changed, what’s not being enforced, and what real estate investors, title agents, attorneys, and closing professionals should be doing right now. Key takeaways:• No FinCEN reporting required (for now)• No penalties for not reporting• But required information still needs to be collected With conflicting federal rulings out of Florida and Texas, the future of this rule remains uncertain—so staying compliant without overreacting is critical. If you’re involved in cash transactions, land trusts, or entity-based purchases, this directly impacts your workflow. Tune in to get clear on what matters right now. Have a question for a future Ask Joe episode? Send it our way. Subscribe for more episodes of Trust This and stay ahead of what’s changing in asset protection and real estate. Learn more about land trusts: https://mylandtrustee.com/book/Stay updated with the Trust This newsletter: https://trustthis.beehiiv.com/subscribeExplore asset protection services: https://aspirelegal.com/contact/

March 12, 202655 min

Ask Joe Q & A - Asset Protection, Estate Planning and More!

In this episode, Attorney Joe Seagle hosted a candid, unscripted Q&A focused on the real legal questions entrepreneurs and real estate investors face every day. Drawing from decades of experience, Joe tackled topics ranging from advanced asset protection strategies and Florida land trusts to estate planning, business structuring, and investor-focused legal planning. As the co-author of Land Trusts in Florida and founder of Aspire Legal Solutions, Joe shared practical insights gained from helping thousands of investors, business owners, and families protect what they’ve built. Throughout the conversation, he simplified complex legal concepts and translated them into clear, actionable guidance listeners can apply to their own businesses, investments, and long-term planning. Listeners submitted real-world scenarios, giving Joe the opportunity to explain how strategic structuring can prevent costly mistakes, strengthen asset protection, and create a more durable legal foundation for growth. The discussion emphasized the importance of thinking proactively about legal planning, especially for entrepreneurs and investors building wealth through real estate or business ownership. By the end of the episode, the takeaway was clear: the right legal structure isn’t just about protection—it’s about clarity, confidence, and long-term strategy. #AspireLegalSolutions #AssetProtectionAttorney #EstatePlanning

February 26, 202648 min

Understanding FinCEN’s RERRR: Land Trusts, Entities, and Reporting Triggers

Beginning March 1, 2026, new federal reporting requirements will reshape certain non-financed real estate transfers — and many investors misunderstand how broad the rule really is. In this episode, real estate and asset protection attorney Joe Seagle breaks down FinCEN’s Residential Real Estate Reporting Rule and addresses a common myth: that simply using a land trust avoids federal reporting. FinCEN is focused on substance over form, meaning the real question is whether beneficial ownership or control actually changes. Joe explains who may qualify as a “reporting party,” how responsibility is determined, and why layered structuring or trust assignments designed to mask a sale can create serious legal exposure. Attempting to outmaneuver the rule could invite federal scrutiny and significant penalties. For investors, attorneys, and title professionals, understanding the rule is no longer optional — it’s part of modern risk management. Listen to the full episode to learn what triggers reporting, how to evaluate your land trust transfers, and what steps to take before the March 2026 deadline. Have a question you want answered on our next Ask Joe episode? Reach out and let us know. Subscribe so you don’t miss future episodes of Trust This: https://www.youtube.com/@TrustThisTV Learn more about land trusts in Land Trusts in Florida, 11th Edition by Mark Warda and Joe Seagle: https://mylandtrustee.com/book/ Stay informed with the Trust This Newsletter: https://trustthis.beehiiv.com/subscribe Protect what matters most. To explore asset protection, estate planning, and business strategies, book your Free Discovery Call today: https://aspirelegal.com/contact/ #FinCEN2026 #FinCENReportingRequirements #LandTrusts #PropertyTransfer