A traditional VPN sends your entire internet history through one company that also has your name, address and payment details. Liam sits down with Carl Dong, founder of Obscura VPN and former Bitcoin Core developer, on why two hops beat one and why AI makes privacy urgent.
Guest: Carl Dong, founder of Obscura VPN and former Bitcoin Core developer:
X: https://x.com/obscuravpn
Website: https://obscura.com/
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ABOUT THIS EPISODE
Carl Dong grew up building ways around China's Great Firewall, then worked at Blockstream and Chaincode Labs on Bitcoin Core, where his focus was software supply chain security. He explains reproducible builds and fuzzing, and why AI's infinite patience turns theoretical attacks into real ones. He makes the case that a traditional VPN swaps your ISP for one unregulated company that sees all of your traffic, and walks through Obscura's two-party relay with Mullvad, where neither company knows both who you are and where you go. He covers disguising VPN traffic as HTTP/3 to get through firewalls in airports, hotels and China, and why privacy tools have to be as easy as the alternatives. Liam and Carl also discuss AI agents overtaking human web traffic, connected AI that may know you better than anyone, private and local models, and how recent hardware wallet supply chain attacks harden the industry.
CHAPTERS
00:00 - Carl Dong: from the Great Firewall to Bitcoin Core
03:15 - The VPN trust problem and the two-party relay idea
06:29 - AI, infinite patience and software supply chain attacks
08:41 - Reproducible builds: verifying Bitcoin Core downloads
11:15 - How a traditional VPN works and what it can see
14:25 - VPNs as custodians: don't trust, verify
15:31 - Beating censorship by looking like normal traffic
18:38 - Mimicking HTTP/3 so VPNs don't get blocked
19:18 - Freedom tech has to be easy to use
22:07 - AI traffic passes human traffic: what changes online
24:59 - AI that knows everything about you, and private AI
29:58 - Local AI models on your phone
30:57 - What's next for Obscura: Linux and automatic protection
32:15 - Supply chain attacks and a hardened Bitcoin industry
34:24 - Where to find Carl and Obscura
ABOUT THE SHOW
Final Settlement Interview Series: a one on one interview series hosted by Liam Nelson, Partner at Early Riders. One guest, and a deep conversation on the deals, the capital and the technology moving through bitcoin, so you can hear how the people actually doing the work think about where the future is going. Presented by Early Riders and Onramp Media.
• Connect with Early Riders: https://www.earlyriders.com/contact
• Liam: https://x.com/Lnelson_21
• Obscura: https://x.com/obscuravpn
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Onramp does not provide financial, tax, or legal advice. Nothing here is a recommendation to buy or sell any asset. This episode is for entertainment purposes only.
