In this episode of *The Real Estate Note Show*, Dave and Nathan welcome investor David Meyerowitz to explore a powerful yet often overlooked niche: **structured settlements and lottery prize payments**.

David shares how he transitioned from mortgage investing to purchasing guaranteed payment streams backed by top-tier insurance companies.

**What you’ll learn:**

- How structured settlements work and where they come from.

- The court-approval process that makes these investments highly secure.

- Types of payment streams David buys: lottery winnings, legal fee payouts, life-contingent annuities, and more.

- How investors can buy at a discount for steady, predictable returns.

- Why this niche offers fixed-income style security without the headaches of property management.

If you’re looking to diversify your portfolio with safe, hands-off investments that still deliver strong returns, this episode will open your eyes to an alternative cash flow goldmine.

To obtain this week's Real Estate Notes Show guest David Meyerowitz's information, use this link https://bit.ly/4l3Gyil

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[00:00:00] Show Intro and Guest Update[00:01:07] Breaking Rules Buying in Chicago[00:02:03] Recent Influx of Note Assets[00:03:02] Unpredictable Note Performance Stories[00:04:13] Structuring Notes for Maximum Value[00:05:28] Importance of Compliance and Dodd-Frank[00:06:10] Hidden Property Issues on Street View[00:06:29] Shifting to Structured Note Investing[00:07:29] Guest David’s Background Story[00:08:54] Birth of the Lottery Payment Market[00:10:16] Rise of Structured Settlement Annuities[00:12:23] Court Approval Process Explained[00:14:19] Evolution of Lottery Winnings Payouts[00:16:11] Buying Lifetime and Contingent Payments[00:17:27] Why Sports Contracts Are Risky[00:18:09] Interest Rates in Structured Settlements[00:19:32] Security and Risk in Payments[00:20:59] Competition and Pricing Challenges[00:22:42] Investing with Retirement Accounts[00:24:09] How Payments Are Serviced[00:25:19] Reselling Payments Without Court Approval[00:26:24] Rare Disputes and Resolutions[00:27:14] Buying Direct vs. Through Funds[00:28:07] No Reserves Needed for These Deals[00:29:20] Typical Returns Over Time[00:30:17] How Deals Are Sourced[00:31:32] Navigating Broker Relationships[00:31:52] Annual Deal Volume[00:32:34] Ways to Work with David’s Company[00:33:27] Assignment of Payments Process[00:34:03] Minimum Investment Amounts[00:35:31] Matching Investor Payment Preferences[00:36:54] Why This is Great Fixed Income[00:38:24] Smallest and Largest Deals Ever[00:39:19] Secondary Market Advantage over Annuities[00:40:01] Market Fluctuations and Equity Plays[00:40:34] Buying Nationwide, Including Territories[00:41:32] Final Thoughts and Contact Info[00:44:00] Lazy Investing with Guaranteed Payments[00:44:32] Thank You and Closing Remarks