From The System2 Podcast, November 2025: After 21 years in the Marine Corps, Brian “Tosh” Chontosh has a pretty simple way of thinking about leadership: start with being a good human being. Tosh joined Matei on The System2 Podcast for a conversation about his career in the Marines, from enlisting at 18 and later becoming an officer to combat in Iraq and teaching leadership at the Naval Academy. In this clip, he talks about what he tried to teach the young officers there, and why character matters just as much as being good at the technical parts of the job. The full conversation gets into trust and team building, some of his experiences in combat, his transition out of the military, and the work he now does with veterans through Big Fish Foundation, which he founded in 2020. Full episode: youtube.com/watch?v=DFDdp0DX…

From The System2 Podcast, December 2025: Long before Amazon became what it is today, Wes Shepherd was looking at a different corner of e-commerce: what happens to all the products people send back. He saw an opportunity to connect returned, refurbished and excess inventory from major brands with the rapidly growing market on eBay. That eventually turned into a business working with companies like Philips and Nespresso, and later led Wes into data and analytics. Wes, now Chairman & CEO of Hoodie Analytics, joined Matei on The System2 Podcast to talk about that path from growing up in Alaska and getting into e-commerce in the ’90s, to building and selling Channel IQ, starting Unifyd Insights, and eventually building Hoodie in the cannabis data market. The conversation gets into how he’s found new businesses, what he learned from the ones that worked better than others, and why he now spends a lot more time finding the customer before building the product. Full episode: youtube.com/watch?v=cxUlQ_6C…

From The System2 Podcast, December 2025: When Brett Donnelly decided to sell Acacia Counseling & Wellness, he spoke with a few investment bankers, and then decided he’d rather try selling the company himself. In this clip, Brett tells Matei how he ran the process, got multiple buyers competing for the company, and ultimately beat the valuation range the bankers had given him. Brett is a psychologist, entrepreneur and founder of LMTLSS. The full conversation goes well beyond the sale: how he built Acacia from a small practice into a company with roughly 200 employees, what changed for him after the exit, his relationship with money and ambition, and why relationships and community have become a much bigger part of what he wants to work on now. They also talk about his book Rich From Trauma and the experiences behind it. Full episode: youtube.com/watch?v=6RpqvqHs…

From The System2 Podcast, January 2026: Having cash on the sidelines can feel like you’re missing out. James Wilcox makes the case for why that isn’t always a bad thing. James is a Senior Investment Advisor at General Catalyst and has spent more than two decades in investing and wealth management, including at Goldman Sachs and First Republic. He joined Matei on The System2 Podcast to talk about investing, working with founders, and some of the lessons he’s picked up over his career. In this clip, they get into liquidity and why having some dry powder can matter most when markets are having a bad year. The conversation also covers venture capital, career decisions, dealing with difficult feedback, and James’ somewhat unexpected path from politics into finance. Full episode: youtube.com/watch?v=mIuxMFl0…

From The System2 Podcast, January 2026: People connect with people, not polished corporate stories. Scott Mann, retired Green Beret, bestselling author and founder of Rooftop Leadership, joins Matei Zatreanu on The System2 Podcast for a conversation about leadership, trust and why personal storytelling can be such a powerful way to connect with people. Scott spent more than two decades in the Army and Special Operations before moving into storytelling, theater and leadership training. In this clip, he explains why sharing a real experience can help someone see their own story in yours, and build trust before you ever get to the pitch. The full conversation gets into his path to becoming a Green Beret, his difficult transition back to civilian life, the role storytelling played in that transition, Operation Pineapple Express during the withdrawal from Afghanistan, and what his experiences have taught him about communicating and leading in low-trust environments. Scott has continued bringing those experiences to the stage, most recently through 11 Days, his one-man play about Operation Pineapple Express. Watch the full episode: youtube.com/watch?v=t5sOCTHD…

From The System2 Podcast, January 2026: Demian Costa’s career has taken him from the Navy SEALs to Under Armour, investing, entrepreneurship and, more recently, building businesses in Kosovo. In this clip, Demian tells Matei Zatreanu how a need for outsourced talent led him to Kosovo and eventually became Outsorcy, a business built around connecting companies with teams in the Balkans and Eastern Europe. The full conversation goes well beyond outsourcing. Demian talks about his path into the SEALs, what military training taught him about leadership and teamwork, his transition into the private sector, and how he thinks about building strong teams and cultures. Watch the full episode: youtube.com/watch?v=VOodYTb4…

From The System2 Podcast, February 2026: What makes it easier to take the risk of starting a company later in your career? For Iulian Bobe and David Culp, part of the answer is experience: knowing the industry, understanding the financials and being less afraid of making mistakes. Iulian, CEO, and David, COO, are the co-founders of UpCycle Fiber, a company building systems to keep textile waste out of landfills by sorting and recycling discarded textiles and turning the recovered fibers into new materials and products. They join Matei Zatreanu on The System2 Podcast to talk about how they built the company, the economics of textile recycling, what happens to the enormous amount of clothing we throw away, and how their backgrounds in polymer science and textile manufacturing helped them find a practical way to turn waste into something valuable. Watch the full episode: youtube.com/watch?v=51s5uoGo…

From The System2 Podcast, February 2026: AI has made it much faster to turn an idea into something you can actually test. But the fundamentals of building a good business haven’t changed. Evan Shy, entrepreneur, investor and Operating Partner at Vitamin Capital, joins Matei Zatreanu on The System2 Podcast to talk about building companies, developing tech talent and how AI is changing the way we work. In this clip, Evan explains why AI can dramatically shorten the path from idea to prototype, while the things that make a business durable (solving a real customer problem, differentiating what you’re building and finding a repeatable way to acquire customers) still matter just as much. The full conversation also gets into Evan’s path from entrepreneurship to investing and back into the operator seat, the changing market for tech talent, and which skills may become more valuable as AI takes on more execution-heavy work. Watch the full episode: youtube.com/watch?v=QG4qnQ3h…

From The System2 Podcast, February 2026: What happens to service businesses when everyone has access to the same AI tools? @dgcattaneo , Co-founder of Coologee and leadership and executive coach at Authentic Leadership for Everyday People, joins Matei Zatreanu on The System2 Podcast to talk about his career across investment banking, consulting and digital marketing, and why he eventually left the traditional executive path for coaching. They get into leadership, the difference between managing people and actually understanding how they work, what Dino learned from growing up in a family of business leaders in Italy, and how his definition of a successful career changed over time. In this clip, Dino talks about what AI could mean for service businesses: some of the more mechanical work will become easier to automate, while human experience, judgment and a differentiated point of view may become more valuable. Watch the full episode: youtube.com/watch?v=DKy9RGys…

From The System2 Podcast, March 2026: Some of the best opportunities for technology are hiding in industries where the people closest to the problems don’t necessarily have the tools to build the solutions. Lara VandenBergh, a policy professor at the University of Denver Graduate School of Social Work, joins Matei Zatreanu on The System2 Podcast to talk about her career in social work and what she’s learned working with very different populations, from people with disabilities in New York to aging veterans at the VA. They get into why Lara moved from clinical work toward policy, the bureaucracy that can make healthcare harder to navigate, and where technology could help solve problems that still rely on phone calls, faxes and highly manual processes. The conversation also touches on her family and the influence of her grandfather, cartoonist Will Elder, her work with veterans and families of people with disabilities, and how she thinks about purpose and raising her own children. Watch the full episode: youtube.com/watch?v=Fb9drE-V…