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by Hosted by Haley Berkoe
Haley Berkoe asks some of the biggest names in bitcoin and Silicon Valley 21 questions in 21 minutes, from the personalities you know and love to tech’s unsung heroes. A new episode drops when someone stops by Presidio Bitcoin.
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- 3 weeks ago22 min
21 in 21: Calle on Cashu, Clawi, and AI Agents
On this episode of 21 in 21, Calle discusses his work on Cashu, Bitchat, and Clawi. He explores how AI agents could use bitcoin-native payments and why privacy-preserving infrastructure matters in an increasingly agentic internet. Calle also reflects on his journey down the bitcoin rabbit hole, from early work on Lightning infrastructure to building eCash systems, and shares his perspective on the evolution of AI agents. https://x.com/callebtc https://clawi.ai/ https://bitchat.free/ https://cashu.space/
- Apr 16, 202626 min
21 in 21: Linn Bieske on Hack-Nation and Building Global AI Communities
Linn Bieske, Co-Lead of the AI & Technology Track at the MIT Club of Northern California (CNC), AI Product Manager, and Co-Founder of Hack-Nation, joins Haley Berkoe on 21 in 21. They discuss the upcoming Hack-Nation event on April 25 and Spiral’s sponsored challenge exploring what becomes possible when AI agents can earn using the Lightning Network. Linn also shares her perspective on what motivates today’s AI builders, how to design experiences that lead to something more lasting than a 24-hour sprint, and why community and collaboration matter so much. Apply by April 19 to join the upcoming hackathon, or follow along for the next one. https://hack-nation.ai/ https://www.linkedin.com/in/linn-bieske-189b9b138/ https://www.linkedin.com/company/hack-nation/ https://www.linkedin.com/in/haleyberkoe/ https://spiral.xyz/
- Apr 7, 202625 min
21 in 21: Rainey Reitman on Transaction Denied and Financial Censorship
Rainey Reitman joins 21 in 21 for a conversation on financial censorship, free speech, and her new book, Transaction Denied: Big Finance’s Power to Punish Speech. Rainey co-founded Freedom of the Press Foundation and serves on the board as president. She also spent 11 years at the Electronic Frontier Foundation, first as Activism Director and later as Chief Program Officer. Drawing on years of work in civil liberties advocacy, Rainey explains how lawful speech can still lead to frozen accounts, denied payments, and exclusion from the financial system. She also shares how these issues connect to journalism, whistleblowers, privacy, and Bitcoin’s promise, and limits, as a censorship-resistant tool. Links to Book: Amazon: https://a.co/d/04WK0Qek Bookshop: https://bookshop.org/lists/transaction-denied-big-finance-s-power-to-punish-speech Audio: https://www.audible.com/pd/Transaction-Denied-Audiobook/B0FJZRQXXR?source_code=AUDORWS0718179KY7 A portion of every book sale goes to support Freedom of the Press Foundation. “In her timely and necessary book, Reitman illuminates the shocking and widespread censorship exerted by the American banking system, details how Orwellian financial surveillance and control has become the norm, and makes a powerful case for why we must push for change if we want to preserve freedom and privacy in the 21st century.” — Alex Gladstein, Chief Strategy Officer, Human Rights Foundation Follow: https://x.com/RaineyReitman https://x.com/FreedomofPress
- Mar 19, 202622 min
21 in 21: Michael Saylor on Bitcoin, AI, and Advice for Builders
Michael Saylor joined Haley Berkoe on 21 in 21 for a rapid-fire conversation on bitcoin, AI, and what’s coming next. He shares what’s top of mind for 2026, why he sees this year as a major turning point, and how he thinks bitcoin could evolve as digital capital beneath new layers of credit and currency. Then, Saylor gets into how AI will radically transform civilization, and how that shift could make bitcoin even more important in a world where autonomous agents need to transact constantly with digital capital. He points to Strategy’s use of AI in creating digital credit products like Stretch (STRC), and shares the kinds of bitcoin products he hopes to see, from deeper integration into everyday technology to applications powered by bitcoin. Saylor emphasizes that we’re entering one of the most fertile periods ever for building, and encourages builders and young people to spend a lot of time learning AI tools and continually pushing themselves to create something new and useful. There are also a few fun detours into MIT prank stories and the AI-generated X profile images he’s become known for. Follow: https://x.com/saylor https://x.com/HBerkoe https://www.youtube.com/@PresidioBitcoin Links: https://www.michael.com https://www.hope.com https://www.uncute.com/products/here-comes-bitcoin
- Mar 17, 202624 min
21 in 21: Andi Pitt on Bitcoin Venture, AI, and Cognitive Sovereignty
Andi Pitt of Ego Death Capital joined me on 21 in 21 to talk about the rise of new startups in the bitcoin ecosystem, how the funding landscape has changed, and the growing intersection of bitcoin and AI. She also shares what she looks for in founders and offers advice for launching a startup. Beyond venture, Andi discusses her recent research into mind control and cognitive sovereignty. Note: We recorded this while Andi was in town last November for the HRF AI for Individual Rights Summit. https://x.com/1andipitt https://egodeath.capital/ https://clyrapassages.substack.com/
- Jan 13, 202622 min
21 in 21: Mark Suman on Privacy-First AI
Mark Suman, co-founder and CEO of Maple AI, a privacy-first AI chat platform known as “the Signal of AI,” joins Haley Berkoe on 21 in 21. Mark explains how Maple AI uses secure enclaves to deliver a ChatGPT-like experience while getting as close to local-AI privacy as possible, without requiring users to run models on their own machine. He also covers why verifiability is essential for trust, the importance of thought privacy, the shared ethos between Bitcoin and AI, and why AI in schools deserves more scrutiny. Maple AI: https://trymaple.ai/, https://x.com/TryMapleAI Mark Suman: https://x.com/marksuman
- Dec 17, 202523 min
21 in 21: David Gumberg on the Chaincode ₿OSS Challenge and Becoming a Bitcoin Core Contributor
Haley Berkoe sits down with David Gumberg, a Bitcoin Core contributor at Localhost, a bitcoin-focused research center in the Bay Area. David shares how he got into bitcoin, what pushed him from curiosity to contribution, and how completing the Chaincode ₿OSS Challenge in 2024 helped him make the leap to contributing to Bitcoin Core full time. They also dig into what he’s focused on now in Core: Compact Block Relay, block propagation times, and why improving network latency can make mining more fair for smaller miners. bosschallenge.xyz (applications due Dec 31) github.com/davidgumberg x.com/ChaincodeLabs x.com/lclhostresearch x.com/HBerkoe
- Dec 11, 202524 min
21 in 21: Rod Roudi
In this episode of 21 in 21, Haley sits down with Rod Roudi, co-founder of Bitcoin Park in Nashville and Austin. Rod breaks down how Bitcoin Park began, why in-person energy fuels strong communities, and how Nashville grew into a hub for bitcoiners, policymakers, founders, developers, and bitcoin-curious locals. He also shares what he’s learned about bitcoin payments from the business side, why reducing merchant friction is essential, and what he’s looking forward to in 2026. Episode Chapters 00:00 Welcome Rod 01:44 Bitcoin Park Description 03:39 Origin Story 07:08 Engaging Policymakers and Local Community 13:38 Accepting Bitcoin as a Business 16:22 Merchant Adoption and Reducing Friction 20:22 College Basketball Break 21:47 What Rod Is Excited About in 2026 23:06 Where to Follow Rod & Bitcoin Park https://x.com/bitkite https://x.com/bitcoinpark_ https://x.com/HBerkoe
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About 21 in 21
Haley Berkoe asks some of the biggest names in bitcoin and Silicon Valley 21 questions in 21 minutes, from the personalities you know and love to tech’s unsung heroes. A new episode drops when someone stops by Presidio Bitcoin.
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