21 in 21

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

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

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/

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

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