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Michael Sullivan joins the show to explain why he published the most bullish piece of his bear market at $63K, and why Bitcoin ripped 15% in 48 hours right after. Michael spent thirteen years as a fintech engineer and writes fiction on the side, and he's turned both into a methodology: measuring the emotion in how Bitcoiners actually talk, cohort by cohort, week by week. His argument is that when every trader is bored, fearful, and rotating into AI and quantum, that isn't a bear signal. TIMESTAMPS: 0:00 Intro 0:21 From boredom to a 15% move in 48 hours 2:34 Why apathy produces the biggest moves 5:27 The trader cohort and the rotation to AI and quantum 7:35 The price heat map: nobody talking about price 9:55 Bessent, liquidity, and why narratives get rewritten 12:26 From fintech engineer and novelist to language analysis 15:50 What he actually measures 19:13 Signal versus noise: bots, aggregators, and cohorting by hand 22:15 Why MSTR holders got more convicted 25:51 Fundamentalists versus capitalists 28:40 The treasury investor is a different investor 31:59 Modeling institutional sentiment 34:56 Why X is the highest-signal source 36:29 BIP 110 and the echo chamber 40:52 mNAV is sentiment 44:52 STRC narrative volatility 49:08 The bear case: what would flip him 50:38 Fading the four-year cycle 54:50 Is the four-year cycle dead? 57:14 Where to follow Michael 🎙️ Featured Guest: Michael Sullivan — author of Bitcoin Sentiment Weekly, fintech engineer, and novelist Kalshi Perps Sign up at https://kalshi.com/p/bitcointreasuries Please carefully consider if it is appropriate for you in light of your personal financial circumstances. Kalshi products are not available in all jurisdictions. See kalshi.com/regulatory for more information. Leverage amplifies both potential gains and potential losses, and losses can exceed the amount deposited. Leverage limits are determined by KalshiEX LLC or the FCM based on its own risk assessment and each customer's individual risk profile, and are subject to change. Perpetual Futures are listed on Kalshi Ex LLC, a CFTC-regulated exchange, and may be traded directly as an exchange member or through an approved broker. This video is sponsored by Kalshi. 🤝 SUPPORT OUR SHOW: BitGo is the institutional-grade digital asset infrastructure trusted by thousands of institutions worldwide. A publicly traded company on the NYSE, BitGo offers regulated custody, OTC trading, financing, and settlement under one roof — and holds a federally chartered national bank license from the OCC. Learn more at https://bit.ly/bitGo Arch Lending offers the most transparent Bitcoin-backed borrowing experience in crypto — industry-leading rates from 8.49%, qualified custody, no rehypothecation, and verifiable segregated addresses. Simple terms and public pricing at every size. Learn more at https://bit.ly/archlending XCE Connecting Excellence Group is the UK's listed Bitcoin treasury recruitment company — placing senior talent into Bitcoin companies globally and helping operating businesses build on a Bitcoin standard. Learn more at https://bit.ly/XCEio Hemi — Activate compliant Bitcoin yield without leaving custody. Built by Bitcoin OG Jeff Garzik, Hemi is the only blockchain that embeds a full Bitcoin node inside an Ethereum node for true Bitcoin finality. Follow them at https://twitter.com/@hemi_xyz and learn more at https://hemi.xyz

Matt Tuttle is CEO of Tuttle Capital Management, an ETF issuer running roughly four to five billion dollars across thematic, options-based and event-driven funds. He has been on Wall Street since 1990 and came to Bitcoin through the ETF wrapper rather than through conviction. His argument is that the wrapper was the entire event: once BlackRock launched IBIT the skeptic case stopped being arguable, and his client portfolios now carry 6.25% Bitcoin against an industry standard of one to two percent. TIMESTAMPS: 00:00 Cold Open 00:52 Trading Since the Eighties 01:51 The iBit Turning Point 02:52 The Argument Wall Street Can No Longer Make 05:08 Why 1% Bitcoin Doesn't Move the Needle 06:30 The HEAT Formula 08:54 The Hard Money Hedge 10:58 What Actually Broke the Treasury Trade 12:30 Bitcoin Fell 50%, the S&P Fell 60% 15:24 How to Play Pre-Merger SPACs 20:44 Why He Hates Covered Calls 22:27 All of Bitcoin's Upside, Not Most of It 25:41 Partnering With Strive on Digital Credit 28:06 A Million Dollars and $40,000 a Year 30:02 Inside the Leveraged Credit ETF 34:58 Why Volatility Isn't Maturing Yet 38:01 Schiff, Pomp, and the Debate That Misses 45:27 Wiped Out at 21 48:15 Zero Percent Bonds at 57 50:14 The Longevity Problem Nobody Plans For 51:46 Grading Powell, Sizing Up Warsh 53:56 Guys Like You Are Screwed 56:36 Where to Find Matt 🎙️ Featured Guest: Matt Tuttle — CEO, Tuttle Capital Management Kalshi Perps Sign up at https://kalshi.com/p/bitcointreasuries Please carefully consider if it is appropriate for you in light  of your personal financial circumstances. Kalshi products are not available in all jurisdictions.  See kalshi.com/regulatory for more information.   Leverage amplifies both potential gains and potential losses, and losses can exceed the amount deposited. Leverage limits are determined by KalshiEX LLC or the FCM based on its own risk assessment and each customer's individual risk profile, and are subject to change.  Perpetual Futures are listed on Kalshi Ex LLC, a CFTC-regulated exchange, and may be traded directly as an exchange member or through an approved broker. This video is sponsored by Kalshi. 🤝 SUPPORT OUR SHOW: BitGo is the institutional-grade digital asset infrastructure trusted by thousands of institutions worldwide. A publicly traded company on the NYSE, BitGo offers regulated custody, OTC trading, financing, and settlement under one roof — and holds a federally chartered national bank license from the OCC. Learn more at https://bit.ly/bitGo Arch Lending offers the most transparent Bitcoin-backed borrowing experience in crypto — industry-leading rates from 8.49%, qualified custody, no rehypothecation, and verifiable segregated addresses. Simple terms and public pricing at every size. Learn more at https://bit.ly/archlending XCE Connecting Excellence Group is the UK's listed Bitcoin treasury recruitment company — placing senior talent into Bitcoin companies globally and helping operating businesses build on a Bitcoin standard. Learn more at https://bit.ly/XCEio Hemi — Activate compliant Bitcoin yield without leaving custody. Built by Bitcoin OG Jeff Garzik, Hemi is the only blockchain that embeds a full Bitcoin node inside an Ethereum node for true Bitcoin finality. Follow them at   / @hemi_xyz   and learn more at https://hemi.xyz

Matt Cole is back. The last time Strive's CEO sat down with Bitcoin Treasuries, they had roughly 6,000 Bitcoin. Today they're closing in on 20,000 — a top seven public holder — and they did it while Bitcoin fell close to 50%. He covers how the digital credit engine kept running through the bear market, the super cycle thesis, why the $60 trillion income market's structural breakdown created a permanent bid for SATA, the controlled burn that trapped a $100M+ short position, the investor protections institutions actually care about, his candid take on Saylor's missteps with the cash reserve, why the death of crypto is bullish for Bitcoin, and why every company without Bitcoin should be scared of AI. Follow Matt: ⁠https://twitter.com/@ColeMacro⁠ Learn more: ⁠https://strive.com⁠ 🎟️ Bitcoin Treasuries Conference — September 28, New York CitySave 10% on tickets: ⁠https://bit.ly/4f1kGV5⁠   TIMESTAMPS: ⁠00:00⁠ Cold Open⁠ 01:21⁠ Why This Bear Market Was Different ⁠05:03⁠ Income Investing Is Broken ⁠07:05⁠ When Matt Knew SATA Would Work⁠ 15:49⁠ Credit Risks Of Digital Credit ⁠18:40⁠ Strive's Capacity To Issue More Prefs ⁠21:04⁠ Building a Track Record & Institutional Trust ⁠26:57⁠ The Engine Behind Strategic Decisions⁠ 33:17⁠ Amplification & USD Runway⁠ 40:30⁠ M&A in the Bitcoin Space ⁠44:09⁠ Semler Merger Story & Industry Networking⁠ 47:24⁠ Criticism From Bitcoiners⁠ 53:14⁠ SATA's Controlled Burn Strategy⁠ 59:42⁠ Super Cycles, AI & Crypto's Death ⁠1:04:55⁠ Stay Orange   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Jeff Garzik was one of Bitcoin's first core developers. He emailed patches directly to Satoshi, helped build the foundational software Bitcoin still runs on, and bought the domain that became BitcoinTalk.org. Now he's building Hemi — a Bitcoin-secured L2 — and he has a message for every Bitcoin treasury company: you're leaving money on the table. He covers the Great Slashdotting of July 2010, why the white paper almost didn't matter without the code, the early fear of being arrested for open source development, why 99% of crypto going to zero is actually great news, what Hemi is and why Bitcoin programmability has existed since the genesis block, the De-Genslerification that unlocked institutional Bitcoin, and why yield is the missing step every treasury company is skipping. Follow Jeff: https://twitter.com/@jgarzik Learn more: https://hemi.xyz 🎟️ Bitcoin Treasuries Conference — September 28, New York City Save 10% on tickets: https://bit.ly/4f1kGV5 CHAPTERS: 00:00 Cold Open 00:55 Bitcoin's Exciting Earliest Days 10:03 The Excitement of Early Bitcoin Days 15:58 Bitcoin Can't Be Stopped 21:50 Darwinian Competition In Crypto 28:02 Understanding Hemi: A New Layer for Bitcoin 38:30 Treasury Companies Are Missing Yield Opportunity 46:15 Is Centralization A Concern? 50:50 Stay Orange 🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Dylan LeClair is the first Metaplanet executive to speak publicly in English about Metaplanet Securities — the newly acquired Type 1 securities license that the company says changes everything about how Japan accesses Bitcoin. He joins Miller Cole for the full breakdown. They cover what a Type 1 license actually unlocks, $7 trillion in idle Japanese savings, why institutional career risk hasn't been stripped away in Japan yet and what flips it, the MSTR rerun Dylan sees playing out, Project Nova, the tokenization rails being built for daily dividends, the Mars and Mercury preferred instruments, and why 27 months of unwavering conviction through a bear market is the most important thing Metaplanet has built. Follow Dylan: ⁠https://twitter.com/@DylanLeClair⁠ Follow Miller: ⁠https://twitter.com/@medc3005⁠ Learn more: ⁠https://metaplanet.com⁠   🎟️ Bitcoin Treasuries Conference — September 28, New York CitySave 10% on tickets: ⁠https://bit.ly/4f1kGV5⁠   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Tim Enneking has been in crypto for thirteen years and previously ran the best-performing hedge fund in the world in 2021. He joins Alec Beckman of Psalion for a conversation on the death of the four-year cycle, why Bitcoin is being mislabeled as a risk-on asset, and why Strategy's concentration may now be a risk to the very market it helped build. They cover Enneking's Law, the long squeeze risk in leveraged Bitcoin buying, what Strategy's endgame actually has to look like, the Clarity Act as the next major catalyst, and how Psalion generates Bitcoin yield through automated market maker liquidity — with self-custody preserved on the lending side. Learn more: https://psalion.com   CHAPTERS: 00:00 Cold Open 01:13 The End of the Four-Year Cycle 04:59 Bitcoin as a Risk-On Asset 13:16 Institutional Influence on Bitcoin 18:59 Bitcoin and Fiat's Runway 31:47 Saylor's Dilemma & Concentration Risk 37:22 Strategy Buying The Top Forever? 45:02 MSTR Endgame & BTC Yield   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Sponsored content produced in partnership with Psalion. Not financial advice. Do your own research.

Robbie Mitchnick is Managing Director and Global Head of Digital Assets at BlackRock — the world's largest asset manager. He led the launch of IBIT, the most successful ETF in Wall Street history. Now BlackRock has launched BITA, a covered call Bitcoin product targeting high teens yield while retaining 70% of Bitcoin's upside. Bitcoin Treasuries President and The Bitcoin Historian Pete Rizzo joins Tyler Rowe for the full conversation. They cover the IBIT inflow and outflow data, the hodler thesis ($48B of IBIT's $50B drop was Bitcoin's price, not outflows), why Bitcoin's narrative was badly mismanaged, the machine native money thesis, the debt and deficit catalyst, and why BlackRock now says the question isn't whether Bitcoin is too risky — it's whether it's risky not to hold any. Follow Robbie: https://twitter.com/@RMitchnick Follow Pete: https://twitter.com/@pete_rizzo_ 🎟️ Bitcoin Treasuries Conference — September 28, New York City Save 10% on tickets: https://bit.ly/4f1kGV5   CHAPTERS: 00:00 Cold Open 01:48 IBIT 2.5 Years In - Smashing ETF Records 07:15 IBIT Investors Are Hardcore HODLers 08:41 Bitcoin Portfolio Guidance 12:42 Demand For Institutional BTC Exposure 14:01 Bitcoin Yield & Investor Profiles 16:05 Bitcoin ETFs vs Strategy or Strive 17:37 Demand For Derivatives & Volatility 20:54 Onshoring BTC Options Market 22:22 BITA vs STRC, SATA & Digital Credit 23:14 What Robbie Thinks About Saylor's Strategy 24:43 How Larry Fink Evolved On Bitcoin 27:28 BTC Narrative Problems & Debt, Deficit & AI 37:03 BTC Infrastructure Maturity 39:10 BlackRock's Roadmap & Restraint 41:33 Tokenization & The Broader Ecosystem 44:05 When Does Crypto Cross The Chasm? 45:26 Is It Risky To NOT Hold Bitcoin? 47:37 Robbie's Message To The Institutional Skeptics 48:38 Stay Orange   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Strategy dropped a five-point digital credit framework on a Monday morning. By midweek MSTR was up 11% with Bitcoin flat. Alexandre Laizet of Capital B and Soleil of True North break down why — and why the story isn't that Saylor sold Bitcoin, it's that he built a balance sheet with more firepower than any traditional company has ever had. They cover the $2.55B USD reserve policy, the STRC dividend raise to 12%, the $2B in buyback programs, and the BTC monetization framework. Alexandre makes the case that June and early July 2026 marked the passage from a retail-driven digital credit market to genuine institutional participation. Soleil breaks down the SATA short squeeze mechanics, the 62% overnight borrow rate, and why the soybean analogy explains everything critics are getting wrong about Strategy selling Bitcoin. Follow Alexandre: https://twitter.com/@AlexandreLaizet | https://twitter.com/@_ALCPB Follow Soleil: https://twitter.com/@nithusezni   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Andrew Webley IPO'd The Smarter Web Company in April 2025 when nobody in the UK believed a Bitcoin treasury model would work. Fourteen months later, SWC has raised nearly a quarter of a billion pounds, holds 2,878 BTC, uplisted to the London Stock Exchange, achieved FTSE index inclusion, and acquired Squarebird Agency — and Andrew says the best is still ahead and he can't talk about it yet. He covers the full origin story, what Saylor told him when they met in London, why the UK is the perfect market for Bitcoin preferred equity, what he learned watching STRC and SATA get stress-tested, why FTSE 250 is in touching distance, and his one-sentence answer to every Bitcoin treasury critic. Follow Andrew: ⁠https://twitter.com/@ASJWebley⁠ Learn more: ⁠https://smarterwebcompany.co.uk⁠   CHAPTERS: 00:00 Cold Open 01:35 Andrew's Journey with Bitcoin and Smarter Web Company 09:06 The SWC IPO & Initial Challenges 14:07 Building A Strong Shareholder Base & Community 19:47 Optionality and Mergers & Acquisitions 29:23 Market Positioning In The UK (FTSE 250 & Beyond) 34:13 Preferred Equities In Europe 38:16 Learning From Michael Saylor & Strategy 46:27 The Evolution of STRC & Digital Credit 53:18 Competition Between Bitcoin Treasuries 56:53 Addressing Criticism in the Bitcoin Community 1:02:39 Stay Orange   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net   ⚠️ Not financial advice. Do your own research.   🟠 Stay Orange.

Sam Callahan, Nick Payton, and Alexandre Laizet join Tyler Rowe to break down why STRC at $84 is a 13.7% yield opportunity, what caused the cascading peg breach, and why being bearish on Strategy means being bearish on Bitcoin. *In this episode:* ✅ Why STRC at $84 represents a 13.7% effective yield — and Sam Callahan's case for why the numbers say it recovers ✅ The cascading liquidation event explained — leveraged carry trades in traditional finance, not DeFi, hit the same level and broke the peg in a cascade from 90 to 82 ✅ Why Strategy retiring convertible debt actually improved credit quality — and why the market got it backwards ✅ If you're bearish on Strategy, you're bearish on Bitcoin over the next five to ten years — Sam Callahan makes the case ✅ Three buckets for Bitcoin investors — self-custody Bitcoin, digital equity (MSTR), digital credit (STRC/SATA) — and who each is for ✅ Alexandre's framework: Strike offers Bitcoin-backed loans, Strategy issues digital credit — different sides of the same trade ✅ Odell's tweet — "never put yourself in a position where you need Bitcoin price to go up in the short term" — and why four analysts think that's exactly what Strategy has avoided ✅ BitGo hits Fortune 500 at #273 — and how the inventor of Bitcoin's 2-of-3 multisig became the first infrastructure play to go public ✅ Orange BTC's World Cup campaign — buying 1 Bitcoin for every Brazil goal *TIMESTAMPS:* 00:00 Cold Open 01:58 Navigating BTC / MSTR Bear Market 02:34 STRC, SATA Digital Credit Price Shocks 18:29 Market (Over)Reactions To Strategy 20:24 The Role of Investor Relations 28:37 Durable Bitcoin Treasury Strategies 39:02 Bitcoiner Criticism of Treasuries 59:52 Competition vs. Collaboration in BTC 1:06:57 Expanding Leveraged BTC Exposure 1:10:02 Oranje's World Cup Promotion 1:12:48 BitGo's Impact on Bitcoin Adoption *🎙️ Featured Guests:* Sam Callahan — Director of Bitcoin Strategy and Research, OranjeBTC. Follow Sam at https://twitter.com/@samcallah OranjeBTC: https://oranjebtc.com Nick Payton — VP of Marketing, BitGo. Follow Nick at https://twitter.com/@NickDPayton BitGo: https://bitgo.com Alexandre Laizet — Board Director of Bitcoin Strategy, Capital B. Follow Alexandre at https://twitter.com/@AlexandreLaizet Capital B: https://cptlb.com/ *🤝 SUPPORT OUR SHOW:* BitGo is the institutional-grade digital asset infrastructure trusted by thousands of institutions worldwide. A publicly traded company on the NYSE, BitGo offers regulated custody, OTC trading, financing, and settlement under one roof — and holds a federally chartered national bank license from the OCC. Learn more at https://bit.ly/bitGo COLDCARD is the industry-leading Bitcoin hardware wallet. Secure your Bitcoin at https://bit.ly/coinkiteStore — use referral code 6BT to get 6% off at checkout! Arch Lending offers the most transparent Bitcoin-backed borrowing experience in crypto — industry-leading rates from 8.49%, qualified custody, no rehypothecation, and verifiable segregated addresses. Simple terms and public pricing at every size. Learn more at https://bit.ly/archlending XCE Connecting Excellence Group is the UK's listed Bitcoin treasury recruitment company — placing senior talent into Bitcoin companies globally and helping operating businesses build on a Bitcoin standard. Learn more at https://bit.ly/XCEio Hemi — Activate compliant Bitcoin yield without leaving custody. Follow them at https://twitter.com/@hemi_xyz and learn more at https://bit.ly/hemiXYZ *🔗 Resources:* 🔔 Follow Bitcoin Treasuries: https://twitter.com/@btctreasuries 🔔 Follow Tyler: https://twitter.com/@tylercompiler 🔔 Subscribe: https://youtube.com/@bitcointreasuriesnet 📊 Track every Bitcoin treasury company at https://bitcointreasuries.net *🎬 About the Show:* Bitcoin Treasuries with Tyler Rowe interviews executives, investors, and industry leaders navigating the Bitcoin treasury revolution. *⚠️ Disclaimer:* This podcast is for informational purposes only. Not financial advice. Always do your own research. 🟠 Stay Orange.

Soleil covers why Bitcoin bottoms in August when a hidden network war over blockchain spam reaches resolution, three hard fork scenarios and what Strategy does with 850K forked coins, why STRC is easier to short than SATA in a way that explains the current price divergence, Saylor's Bitcoin selling walkback and why it's giving haters legitimate fuel, and the tidal wave thesis — capital is receding before a Bitcoin tsunami. Follow Soleil: https://twitter.com/@nithusezni YouTube: https://youtube.com/@nithuseznisezni | True North: https://youtube.com/@btctruenorth CHAPTERS: 00:00 COLD OPEN 05:26 Spam War And Network Policy 13:20 BIP 110: Potential Outcomes 24:35 Game Theory & Bitcoin's Future 29:55 Community Divide On Treasury Companies 35:25 Saylor's Controversial Statements 42:24 Saylor's Impact on Bitcoin Adoption 45:14 mNAV Debates 52:36 Options Trading Strategies 1:02:32 AI & SpaceX Stealing The Spotlight   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Brian Phillips built the country's first Bitcoin-only Opportunity Zone fund. Tim Enneking ran his own OZ fund at a near ten-digit family office for nine years — and had never thought to combine the two. In this Psalion series episode, Tim and Alec Beckman sit down with Brian to walk through a structure that lets long-term Bitcoin holders exit completely tax-free after a 10-year hold, with a 30-year window, 30-day liquidity, and trust mechanics that pass the clock to heirs. They cover the One Big Beautiful Bill's rolling 5-year deferral, the wash-sale window Bitcoin holders can still exploit, Tim's advice for Saylor, and why Brian's synthesis of TradFi tax law and Bitcoin antithesis is — in Tim's words — the ultimate Hegelian synthesis fund. Institutional stack: Anchorage Digital, Morgan Stanley, HC Global, Deloitte. Follow Psalion: https://psalion.com Learn more about Psalion Yield and the groundbreaking Psalion Lend -- where you keep custody of your bitcoin at market-leading rates Follow Pearl Bitcoin Fund: https://thepearl.fund   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research.

The most common mistake in a first Bitcoin allocation is not the price paid. It is assuming the execution will take care of itself. Teams make the buy decision, line up the approval, and then route a seven-figure order through the same retail venue they would use to buy a few hundred dollars of Bitcoin. The order fills, but not at the price they saw. The gap between the quoted price and what they actually paid can be significant, and on a large order it is real money. Buying Bitcoin is operationally straightforward. Buying it well, at size, is not. Michael Geraci, derivatives trader at Secure Digital Markets, covers the exchange, execution, and OTC relationships institutional Bitcoin holders need to understand before the first dollar moves. Will Reeves, CEO of Fold, joins with the operator’s view from running a public company that holds Bitcoin on its own balance sheet. “At a million dollars and up is really where the OTC markets offer depth and liquidity.”  — Michael Geraci, Secure Digital Markets What this session covers When a retail exchange stops being enough     Past a certain size, execution cost becomes real. Slippage becomes material around $250K in notional and is unambiguous past $1M, where retail order books cannot absorb the trade cleanly.     A $1M Bitcoin buy typically runs 5 to 60 bps in execution cost. On a single trade that looks small; across a recurring accumulation program it is the difference that decides your cost basis.     OTC desks exist to solve this, offering real depth, bilateral pricing, and a counterparty accountable on the other end of the phone. How a large order actually gets worked     Size is worked, not clicked. A meaningful order is sliced across venues and over time rather than dropped into a single book that it would move against itself.     Execution is benchmarked. Working an order against TWAP or VWAP lets it track the market instead of running ahead of it, which is the difference between a fill a treasurer can defend to a board and one they cannot.     Discretion matters. Bilateral pricing keeps a large order off the public tape, so the trade does not signal its own size to the rest of the market. The operational groundwork that makes execution clean     Tier-1 banking relationships matter. Fiat needs to move cleanly, and wires to crypto venues are routinely flagged or blocked at banks that are not set up for them. Established banking rails remove that friction.     Work with a firm that picks up the phone. Setting up to trade at size involves real onboarding, banking, and compliance questions, and the answers are specific to each entity. A client-centric desk walks you through them with a named person on the other end of the line, rather than leaving you to a support inbox or a contact form.     Settlement speed is an edge. Pre-funded trades that settle T+0 to T+1 reduce the window in which anything can go wrong, rather than leaving funds in transit for days.     Flexibility is the point of a desk. Bespoke, bilateral structuring gives a treasury options a public order book cannot, from how an order is filled to how a position is later hedged or financed. Get these pieces right and the first allocation stops being a leap of faith. The price you pay is defensible, the execution is clean, and you have a counterparty who answers when you call. From there, the same desk can help the position do more than sit, structuring yield, downside protection, and financing against Bitcoin you already hold, which is exactly the role a desk like SDM is built to play. About Secure Digital Markets SDM is a crypto-native institutional brokerage offering spot execution, derivatives, and structured lending. It specializes in bilateral transactions that give treasuries the depth, flexibility, and privacy a retail exchange cannot match, while clients retain custody of their own assets. You can learn more at SDM.co.

Brandon Quittem wrote some of the most widely read essays in Bitcoin — The Mycelium of Money, Bitcoin Is A Pioneer Species, Bitcoin In The Rhythms Of History — and spent six and a half years at Swan helping people understand Bitcoin from the ground up. He traces Bitcoin's roots through biomimicry and the cypherpunks, explains why the 21 million cap is arbitrary but "hard to change" is what actually matters, takes on Bitcoin's civil war between cypherpunk purists and treasury company buyers, covers Sean Bill's junk bond analogy for digital credit, asks whether Bitcoin could become BitTorrent, and closes with the Fermi Paradox, multiplanetary civilization, and Bitcoin on Mars. Follow Brandon: https://twitter.com/@bquittem Swan: https://swan.com | Swan Private: https://swan.com/private   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.

Strategy sold 32 Bitcoin. Then bought 1,550 the same week. X imploded anyway. Zynx BTC — the Sovereign Individual who tracks STRC and SATA every single day since inception — joins Alexandre Laizet to break down the STRC de-peg trade, why Bitcoin maxis criticizing digital credit are suffering from cognitive dissonance, why STRC already does more volume than every other preferred equity combined, and why institutions with 10–15% return targets are quietly circling. Follow Zynx: ⁠https://twitter.com/@ZynxBTC⁠ Follow Alexandre: ⁠https://twitter.com/@AlexandreLaizet⁠   🏛️ Institutional custody & OTC at bit.ly/bitGo 🔒 Secure your Bitcoin with COLDCARD — use code 6BT for 6% off at bit.ly/coinkiteStore 🏦 Borrow against your BTC from 8.49% at bit.ly/archlending 💼 Bitcoin executive recruitment at bit.ly/XCEio ⚡️ Bitcoin yield without leaving custody at bit.ly/hemiXYZ   📊 Track every Bitcoin treasury company at bitcointreasuries.net ⚠️ Not financial advice. Do your own research. 🟠 Stay Orange.