From Army Green Beret to crypto CEO and a16z deal partner? It's not as unusual as you might think. Alex Pruden, now CEO of the Aleo Foundation, recognized a connection between terrorism, economic inequality, and the lack of secure digital identity while serving on three different battlefields. In this episode, he shares how his experiences led him from the military to the world of venture capital at a16z, and ultimately to zero-knowledge cryptography, exploring how this technology can help address some of the most fundamental but poorly understood human rights: privacy and digital identity.

In this episode, we dive into the origins and impact of social media with one of its OGs, Evan-Henshaw Plath, better known as Rabble.

Rabble is one of the original minds behind X, then known as Twitter. We explore his serendipitous journey from Odeo to Twitter, candidly address both the overwhelming net good and unintended consequences of social media, and weigh the impact of disinformation and societal division on democracy and participation. We also tackle the complexities of content moderation, privacy, and the challenges of fostering healthy online communities. This episode offers a nuanced perspective on the tech world, blending personal anecdotes with deep insights into the ever-evolving relationship between technology, society, and ethics.

Jon Wu is head of growth at Aztec, a privacy preserving Layer 2 for Ethereum that took home an impressive Series B last year, led by A16Z. As arguably the public face of Aztec for the past several years Jon speaks and writes some of the most consistently cogent content on everything from encryption and privacy to DeFi and finance to civil liberties and the future of open societies. He's never boring, and you'd never regret being 20 tweets into any X thread that he's written. Here, we compare crypto to casinos and what casinos do right versus what crypto does wrong, examine the multi-hundred year bet Apple made on trust, and understand cryptographic privacy as an insurance policy against volatile times when things don't "just work" as expected.

The soap opera-level drama that unfolded after the surprise ouster of Sam Altman from OpenAI, a company he founded, truly surpasses the hallucinations of even the most imaginative generative AI model.

The revelation that OpenAI, probably the most consequential and certainly the fastest growing tech company in Silicon Valley history, was governed by just 4 staggeringly incompetent directors, felt deeply destablizing.

Thanks to OpenAI, public trust in…well…trustworthy AI seems to be at an all time low. So it’s very lucky that Chad and I had the opportunity to speak with Ben Colman, co-founder and CEO of Reality Defender, a company that provides enterprises with deepfake detection for AI-generated and manipulated content.

Reality Defender sits squarely in the trustworthy AI space, and Ben, formerly a VP at Goldman Sachs, has a unique perspective on protecting trust by defending critical sectors such as finance and banking against an onslaught of synthetic data, fraud, and reality manipulation.

Kurt Opsahl is the Associate General Counsel for Cybersecurity and Civil Liberties at Filecoin Foundation, and previously served as Deputy Executive Director and General Counsel at Electronic Frontier Foundation for almost 20 years. EFF is a sought-after source for deeply thought-through, detailed, and often lacerating research and advocacy on all things digital privacy, free speech, and technological innovation. As a lawyer, Kurt offers a perspective on privacy rooted in Constitutional and case law, a side of privacy we haven’t explored yet on the podcast. And having watched the intersection of law and technology evolve for well over twenty years, there's no one better to speak to these issues than Kurt.

Gordon is building Subconscious, an AI-powered “knowledge graph” that stores your thoughts and thinks with you.

But how do you augment human consciousness without giving companies unfettered access to your private thoughts -- and without network effects that keep your personal AI on a platform you don't own?

The modern internet has turned oversharing into a business model. Your address and phone number are confetti'd across a thousand websites and ad networks. Your Likes and link trail are meticulously analyzed by machine learning models for precision nudging and irresistible microtargeting to get you to think, buy, or vote a certain way.

Your data exhaust is the economic engine of the 21st century. Is it possible to imagine a different digital reality?

Elena Nadolinski, founder and "chief instigator" of IronFish, shows how she's using zero knowledge cryptography to build a fully-compliant, privacy-preserving Layer 1 blockchain to minimize the shards of you that are strewn across the internet and give you back agency over who sees your data, what they see, why, and when.