In this episode, Laura and Kevin chat with Walter Haydock, whose path from Marine intelligence to Capitol Hill to AI governance gives him a rare view of what “security” actually means in the age of AI and generative models. Walter talks about why he thinks governance is becoming the next real defense layer, and how to sort actual AI risks from the odd glitches everyone loves to talk about. He breaks down common myths he hears from non-tech folks, what recent cloud outages say about the shortcuts companies take, and whether the latest hospital ransomware attacks signal a true AI-driven threat wave or just better marketing from bad actors.

We also get into the personal side: what feels high-stakes after years in national security, and which unexpected habits from that world turned out to be useful in tech. Walter closes by looking ahead at what might trigger the first serious AI crackdown in the U.S. and whether a federal AI law is finally on the horizon. It’s a grounded, candid look at where the field is headed from someone who’s seen the stakes up close.

Walter Haydock is the Founder and CEO of StackAware, where he helps AI-driven companies handle cybersecurity, privacy, and compliance risk. He’s one of the leading voices on ISO 42001 and has guided organizations through the audit process as AI governance becomes a core part of security. Before building StackAware, Walter worked in national security as a staff member on the House Homeland Security Committee, an analyst at the National Counterterrorism Center, and a Marine Corps intelligence officer. He’s a graduate of the Naval Academy, Georgetown’s School of Foreign Service, and Harvard Business School.

This week’s post-Thanksgiving episode is a full smorgasbord of random stories, internet rabbit holes, and tech-adjacent tangents. Laura and Kevin skip the usual guest and run through a pile of listener-requested topics. They start with the viral Tinder profile of a man who openly admitted to abusing women yet pulled in more than 800 matches, which leads them into the strange world of dating-while-incarcerated sites. From there, they jump to Japan’s businesses that help people legally disappear without a trace, and how that even works in a world where everything leaves a digital footprint. Things keep escalating, including a true story about a man who robbed a bank to get away from his wife, only to be sentenced to house arrest. It’s messy and funny and they somehow still land the plane with a tech angle at the end. Perfect listening if you want something light but still genuinely interesting after the holiday.

This week on the pod, Laura and Kevin sit down with Janna Scott, founder of DeFi Tax, to unpack one of crypto’s most confusing and controversial topics: taxes. Janna shares how she went from frustrated accountant to tech founder after realizing how broken the crypto tax ecosystem was. She explains why the IRS treats digital assets differently than stocks, how compliance rules can border on entrapment, and what it will take for fairer regulation to emerge.

We talk about the darker side of crypto: market manipulation, whales, and whether regulation is actually working or just pushing bad behavior further underground. Through it all, Janna brings a mix of technical insight and practical insight, reminding us that the hardest part of crypto isn’t the technology, it’s the system built around it. Between murky IRS rules and hidden market forces, it’s easy to understand why so many investors feel lost or opt out. But as Janna makes clear, accountability isn't out of reach. You just have to do the math.

Janna Scott is the founder of DeFi Tax, a platform bringing clarity and compliance to cryptocurrency tax reporting. Her journey began in 2021 after her accounting clients raised concerns about unreliable crypto tax tools. Over the next two years, Janna collaborated with the SEC, IRS, and top universities to identify and fix major compliance gaps. Her work set new standards in the field and earned recognition from regulators and academics. Today, DeFi Tax is known for its audit-ready reports, direct blockchain integration, and user-focused design. Janna’s mission is to help individuals and businesses navigate crypto taxes with confidence and transparency.