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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 digita...

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/ ...

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 Suma...

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/davi...

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 <...

Haley Berkoe sits down with Joe Carlo, co-owner of Pink Owl Coffee, a café that began in San Rafael, California, and has since expanded to three locations across the Bay Area. Pink Owl is one of the earliest Square merchants to integrate bitcoin into its business model. For several years, Joe and his partner Saandra have been converting a percentage of sales into bitcoin as part of their long-term savings strategy, and they recently joined Square’s beta program to begin accepting bitcoin payments directly, ahead of the public launch on November 10th. Joe shares how he fir...

Kyle Olney joins Haley Berkoe to talk about defending bitcoin’s foundational freedoms. A longtime Silicon Valley product leader turned bitcoin advocate, Kyle helped launch Save Our Wallets, a coalition fighting for Section 109 of the Clarity Act, and the Satoshi Needs You campaign, a national call to action to protect open-source developers and the right to self-custody. Kyle shares his journey from seizing banks for the U.S. government during the 2008 financial crisis to championing bitcoin’s political and legislative future. He explains the legislative nuances of the Clarity Act, how the wrong version of this bill coul...

In this episode of 21 in 21, Nick Slaney joins Haley Berkoe during Presidio Bitcoin Design Week. Nick is the founder of Money Dev Kit, a new startup building tools that make it easy for developers to add bitcoin and Lightning payments to their applications. Previously, he was at Block, where he helped build Bitkey and c=, whose LDK node became one of the Lightning Network’s largest and most active. He shares why he’s betting on bitcoin over stablecoins, how Lightning service providers (LSPs) improve Lightning usability, and what gives him hope for bitcoin’s future. FOLLOW: ...

During Bitcoin Design Week at Presidio Bitcoin, product designer and HRF grantee Erik Cativo joined the show to talk about designing the future of money. We get into his experiments with ecash and bitchat, the magic of bump-to-pay interactions, and how thoughtful UX can make bitcoin feel intuitive, private, and fun. Erik also shares lessons from living in a nearly cashless society, ideas for building “throw-cash” experiences inside apps like Cash App, and why anyone can help design better bitcoin products simply by giving feedback. FOLLOW: Erik Cativo: https://x.com/uxerik_, https://www...

Haley Berkoe is joined by Kyle Fletcher, Principal Design Director at Block, to explore the intersection of bitcoin, design, and culture. They discuss why artists and designers play a critical role in shaping bitcoin’s future, the sats vs. bitcoin denomination debate, and how thoughtful design can help bring bitcoin to the masses. Kyle also shares personal influences, dream projects, and why onboarding artists, local merchants, and creative communities is key to bitcoin adoption. CHAPTER HIGHLIGHTS: 00:00 Intro & Kyle’s background at Block 01:01 State of Bitcoin brand creative 02:59 Designing future money: local and...

In this episode of 21 in 21, Haley is joined by Christoph Ono, co-founder of the Bitcoin Design Foundation and longtime contributor to the Bitcoin Design Community. They talk about Bitcoin Design Week in San Francisco, the effort to redesign the Bitcoin Core wallet, and why design plays such a critical role in shaping the future of money. Christoph also shares how newcomers can get involved in the Bitcoin Design Community and why making bitcoin feel magical matters. Chapter Timestamps: 00:00 Intro & Christoph’s background 01:05 Bitcoin Design Week in San Francisco 02:51 Designing future money...

In this episode, Haley Berkoe interviews Conor Okus, a Product Manager at Spiral. Conor shares his journey from playing football to becoming a grantee at Spiral and now managing the grant program. He addresses common misconceptions about bitcoin contributors, emphasizes the importance of user experience in promoting adoption, and discusses the emergence of user-friendly (easy) bitcoin addresses. Conor also shares his thoughts on the intersection of AI and bitcoin, the ongoing debate about using "₿ " instead of "sats" to display bitcoin denominations, and offers valuable advice for newcomers to the bitcoin space. EPISODE TIMESTAMPS: 00:00 Co...