Bitcoin 2026 Recap, Stretch Breakdown & The Family Office Launch

20,000 Bitcoiners. Three days in Vegas. More conversations than you can count. Jordan and Wyatt just got back from Bitcoin 2025 and they are breaking down everything that actually happened — from the main stage panels to the back hallway conversations that never get recorded. In this episode, Jordan and Wyatt fly back from Bitcoin Conference 2025 in Las Vegas to give their honest, unfiltered recap of what they saw, who they talked to, and what it all means for the Bitcoin financial services industry. From a packed expo booth to intimate side events to two panels on stage, this one covers the full picture. Wyatt breaks down his two panels — one on Bitcoin-backed lending and scaling debt markets, featuring Salt Lending and Arch Lending, and one on inheritance and wealth building with Jeff Andrew at Unchained, Zach Townsend at Meanwhile, and Jake Calvar at Digital Family Office Group. Jordan covers his panel on 1099-DA reporting, why cost basis schedules are the dark horse issue nobody wants to deal with, and why the IRS forcing mechanism is now unavoidable for anyone who has ever touched an exchange. We dig into the de minimis tax side event hosted at the Venetian, where David Zell from Bitcoin Policy Institute and Janessa Lopez from Block spent an hour with 75 advisors, CPAs, and Bitcoin professionals breaking down where the legislation actually stands — and why getting to crypto tax reform before the midterms is a heavier lift than most people want to admit. Jordan and Wyatt also pull back the curtain on the Bitcoin Family Office initiative they soft-launched at the conference — a fully integrated, Bitcoin-native service model connecting financial planning, tax strategy, estate planning, OTC purchasing, and hosted mining for clients between $5M and $50M in net worth. We get into why the siloed professional model is broken for Bitcoin holders, how data sharing agreements replace the need to tell your story four times, and why the demand they saw on the floor confirmed what they have been building toward for months. We close out with Wyatt's honest breakdown of Stretch — MicroStrategy's preferred equity product paying 11.5% — why it is not a Ponzi scheme, how the dividend liability actually gets paid, and what common shareholders need to understand about dilution versus Bitcoin per share accretion. Jordan adds the tax angle on return of capital treatment and why that structure looks very different from a standard dividend product when April rolls around. Chapters [00:00] Welcome Back and Saylor No-Show [02:53] Why Conferences Actually Work [06:23] Wyatt's Panels: Lending, Inheritance, and Wealth Building [11:07] The De Minimis Tax Side Event Recap [17:16] 1099-DA, Cost Basis, and the Reporting Reality [24:41] Working the Booth and Launching the Family Office [33:00] Stretch Explained: Preferred Equity, Dividends, and Dilution [38:11] Freedom Tech vs. MicroStrategy: The Conference Divide [41:59] Jack Mallers, 21, and Bitcoin Companies Going Public [43:48] Why XRP's Marketing Budget Tells You Everything Host Links Jordan Guess X: x.com/jordanguess LinkedIn: linkedin.com/in/jordan-guess-cpa Website: bitment.co Wyatt O'Rourke X: x.com/wyattorourke_ Website: basilic.io Bitcoin for Financial Services Media X: x.com/bffs_media Website: bffs.media YouTube: / @bffs_media Show Sponsors Basilic Financial — Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. basilic.io Bitment — Tired of messy CSVs and broken cost basis? Bitment is the first Bitcoin-native accounting platform for CPAs, advisors, miners, and serious investors. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co Satoshi Pacioli — Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com