1 Nov 2026
Chat_180 - Invalid Checksum: How I Almost Lost My Bitcoin Stack with STACKTOTHEFUTURE
"There's a lot of emphasis on the moment at how AI is making everything less secure, and that is a part of the story. Of course, any tool, any powerful tool has its advantages and disadvantages or has the thing bad guys can use it, good guys can use it. But the power that I think this actually gives the individual for doing stuff like recovery, I think that in the long run, there's going to be way more people who use this to recover their funds than people who use it and manage to steal someone else's funds. Because of the information you can give it, I got it to interview me: how did I store the seed words? Did I do it in columns or did I do it in rows? Did I mix it? All that stuff I can choose selectively to give to the AI, whereas an attacker, they're basically going in with a kind of like a blank slate and trying to do an attack from relatively low amounts of knowledge in terms of your setup."
~ STACKTOTHEFUTURE
In this Chat, I sit down with my producer and good friend STACKTOTHEFUTURE to unpack how he almost lost half his Bitcoin stack to hardware wallet failures. First from the Coldcard entropy bug scare, then from a degraded Ledger screen and an “invalid checksum” seed.
We walk through his AI-assisted recovery process, why tools like BTCRecover and careful prompting can let you fix mistakes without trusting anyone with your keys, and how this led him to build Keybackup, an open-source printable paper backup for Bitcoin wallets.
Along the way we dive into AI as a net security positive, self-custody tradeoffs, wallet UX for normies, and the Opsec tradeoffs of being public about Bitcoin.
Chapters
(00:00:00) - Introduction
(00:03:42) - Pearcast and AI workflow
(00:06:47) - STACKTOTHEFUTURE joins the show
(00:12:12) - Coldcard vulnerability and Ledger screen fail
(00:20:47) - More supply chain attacks and fake wallet apps
(00:36:00) - Invalid checksum & AI-assisted recovery
(00:58:30) - Red-teaming code and the singularity stack
(01:30:35) - Upgrading paper seed backups with keybackup
(01:42:58) - Opsec, physical security, and PO boxes
Guest Links
STACKTOTHEFUTURE on X (Link: https://twitter.com/stack2thefuture)
KeyBackup's Website (Link: https://keybackup.org/)
Affiliate Links
Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/)
Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1)
Host Links
Guy on Nostr (Link: http://tinyurl.com/2xc96ney)
Guy on X (Link: https://twitter.com/theguyswann)
Guy on Instagram (Link: https://www.instagram.com/theguyswann)
Guy on TikTok (Link: https://www.tiktok.com/@theguyswann)
Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake)
Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann)
Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible)
The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)
bitcoin #economics #freedom
Chapters
(00:00:00) - Introduction
(00:03:42) - Pearcast and AI workflow
(00:06:47) - STACKTOTHEFUTURE joins the show
(00:12:12) - Coldcard vulnerability and Ledger screen fail
(00:20:47) - More supply chain attacks and fake wallet apps
(00:36:00) - Invalid checksum & AI-assisted recovery
(00:58:30) - Red-teaming code and the singularity stack
(01:30:35) - Upgrading paper seed backups with keybackup
(01:42:58) - Opsec, physical security, and PO boxes
Affiliate Links
Become sovereign, hold your keys, be censorship resistant with the BitBox hardware wallet. Get 5% off everything in the store with code GUY. (Link: https://bitbox.swiss/guy/ (https://bitbox.swiss/guy/))
Get 10% off the best Bitcoin board game in the world, HODLUP, or any of the other great games from The Free Market Kids. Use code GUY10 at checkout for 10% off your cart. (Link: https://www.freemarketkids.com/collections/games-1 (https://www.freemarketkids.com/collections/games-1))
Host Links
Guy on Nostr (Link: http://tinyurl.com/2xc96ney (http://tinyurl.com/2xc96ney))
Guy on X (Link: https://twitter.com/theguyswann (https://twitter.com/theguyswann))
Guy on Instagram (Link: https://www.instagram.com/theguyswann (https://www.instagram.com/theguyswann))
Guy on TikTok (Link: https://www.tiktok.com/@theguyswann (https://www.tiktok.com/@theguyswann))
Guy's Take on YouTube (Link: https://www.youtube.com/@GuysTake (https://www.youtube.com/@GuysTake))
Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann (https://www.youtube.com/@theguyswann))
Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible (https://twitter.com/BitcoinAudible))
The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839 (https://tinyurl.com/3na6v839))
