Trust This. | By Joseph E. Seagle, Esq. | 👋 Happy Friday! Memorial Day is behind us, hurricane season starts Sunday, and Florida summer has officially arrived — afternoon thunderstorms, lovebugs on the windshield, and the annual reminder to check the generator before the first named storm. | 🚨 Situation Awareness: Joe is hosting Ask Joe Live, our open Q&A on Florida estate planning and asset protection, this Wednesday, June 3 at 6 PM ET. Register here — bring real questions on dynasty trusts, land trusts, IRA beneficiary designations, or anything else you have been meaning to ask. |
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| | 1 big thing: Congress’s ROAD to Housing Act could reshape Florida investing | | Florida real estate investors, home services contractors, private lenders, and professional practice owners just got a major signal worth pricing into 2026 planning: the biggest federal housing package in a generation is moving toward the President's desk. | The big picture: The 21st Century ROAD to Housing Act (H.R. 1299 / S. 2651) cleared the Senate 89-10 in March and the House 396-16 in May, with a modified version. The two chambers are now reconciling differences. Once the conference report is signed, dozens of provisions kick in — and several of them rewrite the playing field for Florida operators. | The headline items: | Zoning and regulatory preemption — federal incentives for local governments to eliminate restrictive zoning. Florida is already pushing this direction with the Live Local Act and the recently-signed Infill Redevelopment Act. The ROAD Act stacks more weight on the same lever. Section 901 — institutional investor restriction (Senate version) — bars institutional investors controlling 350+ single-family homes from buying or owning additional single-family housing. Whether the final bill keeps Section 901, modifies the threshold, or strips it entirely is the most-watched piece of the reconciliation. But one thing is clear: Mom-and-Pop real estate investors are outside the law’s purview. FHA multifamily expansion — higher maximum statutory loan limits for FHA-insured multifamily projects, useful in high-cost Florida metros. Mortgage delinquency counseling — servicers of FHA, VA, and USDA loans must offer counseling to borrowers 30 days delinquent. New compliance and process work for Florida mortgage operations.
| Why this reshapes Florida planning | Florida has been the favored hunting ground for institutional single-family buyers — Invitation Homes, AMH, and others have concentrated portfolios in Tampa, Orlando, Jacksonville, and Lakeland. If Section 901 survives reconciliation, that competitive lid comes off for sub-350-unit operators. If it dies, the opposite. | What to execute and watch | For Florida real estate investors and private lenders — if Section 901 holds, expect a near-term softening of competition for SFR acquisitions in Central Florida and the I-4 corridor. Reprice your acquisition pipeline for two scenarios and pick a decision date. Private mortgage lenders should also audit servicing protocols for the new FHA/VA/USDA 30-day counseling requirement if they’re originating some loans of this type. For home services businesses — HVAC, plumbing, electrical, painting, carpet cleaning — federal zoning pressure stacked on Florida's existing housing-supply push means more residential density in already-hot corridors. Service-territory mapping and technician hiring should anticipate growth in Orange, Seminole, Osceola, Hillsborough, and Pinellas counties through 2027. For licensed professionals — physicians, dentists, attorneys, pharmacists — new rooftops continue to translate into new patient and client pipelines. Marketing geography should follow construction permits, not zip code maps that are already two years stale.
| The bottom line: Federal housing policy is consolidating in the same direction as Florida state policy: more units, less local resistance, fewer institutional landlords. Position your underwriting and your team for a market with more retail-scale opportunity and tighter compliance overhead. | Watch for: the conference report (expected this summer), whether Section 901 survives, and how Florida cities respond when federal incentives reward eliminating zoning friction. |
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| | 2. The MLS power struggle just hit your deal flow | | Florida real estate investors, brokers, private lenders, and home service operators rely on Zillow as the front door to deal flow and lead flow. That front door just got narrower in one major market — and the same fight could be heading to Florida. | Why it matters: On May 20, 2026, roughly two-thirds of Zillow's Chicago listings vanished overnight. Midwest Real Estate Data (MRED), the Chicago-area multiple listing service, cut off Zillow's data feed in a dispute over Zillow's new April 2026 rule: if a home is marketed on a brokerage's private listing network for more than one business day before hitting the MLS, Zillow refuses to display it. MRED, partnered with Compass International Holdings — the nation's largest brokerage — held the line. Zillow blinked too late. | What's actually moving the market | Compass's private-network strategy is a three-phase sales model. Phase 1: list privately to Compass agents and their clients. Phase 2: a "coming soon" listing on Compass and Redfin without a public price. Phase 3: traditional MLS listing. The model gives the seller pre-market price discovery and lets Compass "double-end" the transaction — keep both sides of the commission. Compass has already partnered with three other MLS providers around the country. Zillow expects them to follow MRED's lead. | Yes, but: the Florida MLS landscape is fragmented — Stellar MLS (Orlando, Tampa), MIAMI Association of Realtors, the Realtor Association of Greater Fort Lauderdale, Northeast Florida Association of Realtors, and others. Each will negotiate its own posture. Florida is not Chicago — but Compass has a meaningful footprint here, and the playbook is portable. | How to use this without getting burned | For Florida real estate investors and private mortgage lenders — diversify deal flow now. If 30% of Florida listings start moving through private brokerage networks first, your buy-side analyst needs direct agent relationships, off-market sourcing channels, and Compass-network access. Underwriting cannot rely on Zillow or even the local MLS as a comprehensive market view. For home services businesses — HVAC, plumbing, electrical, painting — leads that arrive through Zillow ("just bought a house") will thin out in markets where private networks dominate. Build referral pipelines through agents, title companies, and home inspectors directly. The platform-driven lead is at risk; the relationship-driven lead is not. For licensed professionals managing relocation referrals — physicians, dentists, attorneys handling closings — the inventory you can show prospective patients and clients narrows when private networks expand. Lean on local brokerage relationships rather than national portal links.
| Bottom line: A two-player fight over listing access is rapidly becoming a national restructuring of how homes get marketed. The Florida operator who treats Zillow as the only data source is already behind. | What's next: Watch which Florida MLSs partner with Compass-Redfin next, whether Stellar MLS or MIAMI Realtors hold the Zillow line, and whether Florida courts weigh in on fiduciary disclosure rules around “private” listings. |
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| | | This week on an “Ask Joe Anything” edition of the Trust This podcast, I’m explaining the differences between inside and outside creditors and why it’s important to know the difference when designing an asset protection strategy. | Listen in or watch on your favorite streaming platform. |
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| | 3. Dynasty Trusts: building wealth that outlives you | | Most Florida estate plans are built to survive one transfer — yours, to your spouse and your kids. A dynasty trust is built to survive five or six. With so many people talking about these online recently, let’s explain what, when, who, and where they are used. | The big picture: A dynasty trust is an irrevocable trust for ultra-high-net-worth families that is designed to hold assets for multiple generations without triggering federal estate tax or generation-skipping transfer (GST) tax at each generation. Properly funded and properly drafted, the same dollar can pass to your great-grandchildren — and beyond — without being taxed each time the wealth changes hands. | Why it matters: | The federal estate tax rate sits at 40% on amounts above the exemption. Without dynasty planning, the same assets can be taxed at every generational transfer — 40% at your death, 40% again at your child's, 40% again at your grandchild's. Compounded across three generations, that grinds a legacy to a fraction. The GST tax adds another 40% layer when assets skip a generation. The GST exemption ($15 million per individual / $30 million per couple in 2026) is the single biggest planning tool for multi-generational wealth — and it does not automatically refresh from one generation to the next. Asset protection compounds across decades. Properly drafted, the trust protects assets from descendants' divorces, lawsuits, addiction, business failures, and the simple fact that future generations may not be as careful with money as you are.
| What most people don't know: Florida is one of the best jurisdictions in the country for dynasty trusts. Fla. Stat. § 689.225(2)(g) allows a Florida trust to remain in force for up to 1,000 years — among the longest "rule against perpetuities" windows in the country. South Dakota, Nevada, and a handful of other states have abolished the rule entirely, but a millennium is more than enough horizon for any practical legacy. Combined with Florida's lack of state income tax, the Florida dynasty trust often beats the offshore options people pay big retainers to chase. | Key takeaways: | A millennium horizon — Fla. Stat. § 689.225 gives you the runway. No need to "site" the trust in South Dakota for most families. GST exemption is the engine — fund the trust up to the GST exemption while the doubled exemption is still in place. The “One Big Beautiful Bill” — current exemptions ($15M / $30M for 2026) — will adjust up with inflation each year. But the law can always be changed. Use it before another shift. Asset protection compounds — properly structured, descendants' creditors, divorcing spouses, and judgment creditors are blocked from reaching trust assets. Trustee selection drives outcomes — a corporate trustee (an institutional bank or trust company) provides continuity over centuries; a family-member trustee provides discretion and lower fees but limited longevity. No state income tax bonus — Florida-sited trusts avoid the state-level fiduciary income tax that bites in California, New York, and other resident-trustee states.
| Where people go wrong: | Underfunding — putting $500,000 into a structure designed to compound across centuries leaves most of the runway empty. Fund toward the GST exemption ceiling. Forgetting coordination — the dynasty trust has to integrate with the Florida land trust, the LLCs, the revocable living trust, and the retirement account beneficiary designations. Designed in isolation, it fights the rest of the plan. Naming the wrong trustee — choosing a sibling who will be dead before the trust matures, or an institution that charges 1.5% annually for centuries. Treating it as set-and-forget — every 5-10 years, the trust needs a check-up against changes in federal tax law, family circumstances, and asset composition.
| The bottom line: A dynasty trust is not just for the ultra-wealthy. It is for any Florida family that wants the trajectory of their wealth — and the protection of their descendants — to outlast their own lifespan. The architecture exists. The exemption is currently generous. The window does not stay open forever. | Go deeper: Read the full long-form on aspirelegal.com. | This article discusses Florida law. Out-of-state subscribers should consult counsel in their home jurisdiction — dynasty trust mechanics, perpetuities rules, and state fiduciary income tax treatment vary materially by state. |
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| | 4. “How hard could it be?” The most expensive sentence in business |  | For dogs, how hard can it be to open the door and get to that squirrel before it makes it up the tree? |
| Tom Nichols opens The Death of Expertise (Oxford University Press, 2017; second edition 2024) with an observation that should worry every entrepreneur reading this: a Google search, an AI chat, or a confident social media post now produces, in many people, the same conviction that years of training used to. The result is a working population that thinks it knows everything — and a small business class quietly making expensive decisions on the strength of that conviction. | The big idea: confidence is not competence | In 1999, Cornell psychologists David Dunning and Justin Kruger published the study that named the pattern — "Unskilled and Unaware of It." People with limited skill in a domain consistently overestimate their ability in that domain, often dramatically. People with deep skill, by contrast, slightly underestimate themselves because they can see how much they do not yet know. The gap between the two is the Dunning-Kruger effect, a silent tax on entrepreneurship. | The version we see at the firm every month: a Florida business owner uses an online template to form an LLC, names themselves the registered agent at their home address, runs all the money through one bank account, signs every contract personally, and assumes — because the LLC paperwork was filed — that they have "asset protection." They do not. They have paperwork. | How it shows up in your business | DIY legal structuring — a $99 online entity formation that ignores Florida-specific multi-member requirements for full charging-order protection AI-drafted contracts — fast, free, and frequently missing the indemnification, jurisdiction, and limitation-of-liability language that decides who wins a dispute Social-media-driven tax strategy — short-form videos that confidently describe federal tax structures invented for ultra-high-net-worth families, applied to a single-rental-property investor for whom the structure creates more problems than it solves Hiring on confidence rather than credentials — picking the loudest applicant rather than the most qualified one
| Two takeaways from EOS thinking | The Entrepreneurial Operating System has a built-in answer to Dunning-Kruger that most operators miss. Patrick Lencioni's Working Genius framework (a natural complement to EOS) asks each person to name their two natural geniuses — the work that energizes them — and the two natural frustrations, the work they should not be doing. Most owners can list their strengths quickly. Far fewer can name, honestly and out loud, where they are weak. | The discipline: | Audit your last five major decisions. Which were grounded in your actual expertise, an advisor's documented input, or verifiable data — and which were grounded in confident hunch? The second category is where Dunning-Kruger lives. Stack your Accountability Chart against your geniuses. If you are operating in your Frustration zones, you are not just slower — you are confidently wrong more often than you realize. Delegate to someone whose Genius lives there.
| Bottom Line: The cheapest insurance an entrepreneur can buy is a working knowledge of what they do not know. The most expensive sentence in business is "how hard could it be?" — usually said right before someone learns exactly how hard it is. | This Week's Challenge: Identify one decision currently on your plate that sits outside your Working Genius and outside your professional expertise. Before the end of the week, route it to the person — internal or external — whose actual expertise lives there. Resist the urge to "look it up first," or “just ask Chat.” That is the trap. |
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| | We hope you found this helpful — any feedback is appreciated and can be shared by hitting reply or using the feedback feature below. | Was this email forwarded to you? Subscribe here. Have an idea or issue to share? Email us. Connect with us using your preferred social media and website links for MyLandTrustee and Aspire Legal Solutions. My Land Trustee mailing address: PO Box 547945, Orlando, FL 32854-7945 Aspire Legal Solution mailing address: PO Box 547934, Orlando, FL 32854-7934 Our physical address: 1901 West Colonial Drive, First Floor, Orlando, FL 32804
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