Reis O'Donnell joins Edgardo and Shiv for his third appearance on the show, this time fresh off a three-week trip through the Balkans, Greece, and Turkey. The conversation opens with Reis's travels through Serbia (including getting caught in a massive anti-government student protest in Belgrade), a road trip through Bosnia's Dineric Alps and Mostar, island-hopping through Mykonos and Paros, and a whirlwind stop in Istanbul and Athens. From there the trio pivots to Reis's day job as an urban planner, digging into how crash-report data and traffic analysis actually shape infrastructure recommendations, before spiraling into a wide-ranging riff on Chicago transit gripes (the I-88/I-294 exit chaos, Metra vs. CTA, the long-dead Circle Line and STAR Line proposals, and rumors of a Blue Line extension to a potential Bears stadium). The back half covers lighter terrain — feral hogs as an underrated American crisis, Pablo Escobar's wild hippo population in Colombia, China's panda diplomacy, and a spirited World Cup discussion covering red-card calls, Mexico's home-field advantage, and title predictions. It's a classic Reis episode: travel, infrastructure, and a few detours nobody saw coming.

We kick things off with Illinois's new crypto tax, making the case that taxing digital assets on top of existing capital gains amounts to nothing more than double taxation — a policy that ultimately hurts everyday investors more than it protects them. They then shift gears to the 2026 World Cup and how the tournament is doing what few events can — bringing Americans together and bridging cultures across borders. The guys wrap things up across the Atlantic, where the U.K.'s expanding smoking ban is raising serious questions about government overreach and where the line between public health and personal freedom gets drawn.

Edgardo and Shiv kick things off with a candid reflection on what it actually takes to get better at golf — and why raw reps alone won't cut it without deliberate coaching. From the fairway, the conversation shifts to the used car market, where Shiv breaks down the depreciation math on new vs. used and shares his hunt for the right sedan in a world where the average new car is pushing $50K. The guys then get into the credit card game — Amex Platinum vs. airline-specific cards, how to actually calculate the value of perks, and why the welcome bonus is usually where the real money is. They wrap with a timely take on Spirit Airlines' collapse, what it means for budget travelers, and whether the free market will course-correct or just hand the big carriers a blank check to raise prices.

Joined by Adam Leber, Global Chief Compliance Officer at Morningstar, to pull back the curtain on the intersection of high-level finance, emerging tech, and professional agility. We dive deep into the real-world impact of AI in the workplace, exploring how LLM capabilities are transforming the compliance landscape from a "check-the-box" function into a strategic engine. Adam shares pivotal lessons from his time at Alera Group, where he navigated massive organizational growth by blending regulatory expertise with business strategy. The core of the conversation, however, moves beyond the technical; it’s an exploration of career progression defined not by a rigid map, but by the readiness to seize unexpected opportunities and the courage to say "yes" when high-stakes doors swing open.

It's been one year since Liberation Day, and we are taking stock of what the tariff experiment actually delivered — the promises, the pain, and what the data says versus the narrative.Then they flip the script and get personal — ranking six American cities on the only scale that matters: properly rated, overrated, or underrated. Miami, Vegas, Phoenix, LA, New York, and Chicago all go under the microscope. Cost of living, vibes, economic trajectory, who's actually moving there versus who just talks about it — no city gets a free pass.

Edgardo and Shiv break down the economic fallout from the Iran war — spiking oil prices, fertilizer shortages, flight route cuts, and a surprising helium shortage that's threatening AI data center operations. They pivot to the U.S. vs. China energy gap, where China's grid surplus and faster project completion rates are giving them a major AI infrastructure advantage while the U.S. heads toward a demand deficit. They wrap with real AI use cases — Shiv's custom workout agent, Eddy's Claude-powered podcast research system — and land on a shared take: AI won't end the world or steal your job, but how fast you learn to use it will define who pulls ahead in the next decade.

We sat down with Kacper Rutkiewicz — AI educator, YouTuber, and founder of Deep Rooted AI — for a conversation all about the practical power of artificial intelligence. Kacper is building a growing YouTube channel dedicated to making AI accessible, with a focus on tools like Claude, Claude Code, and Claude Cowork, showing his audience not just what these tools can do, but how to actually use them to get real results. We explore why Kacper has become such a strong advocate for the Anthropic ecosystem and dive into real-world use cases across each platform. Beyond his content creation, Kacper runs Deep Rooted AI, a consultancy helping small business owners integrate AI into their products and workflows — meeting them where they are and building sustainable, AI-powered systems that don't require a technical background to maintain.

In this podcast episode, Edgardo, Shiv, and Mike Bockwoldt engage in a lively discussion about music, engineering, and personal interests. The conversation kicks off with a debate over which iconic rap albums should stay or go, featuring artists like Kanye West, Kendrick Lamar, and Drake. Mike shares insights into his work at an automotive manufacturing company, focusing on sound solutions for cars, and discusses the impact of electric vehicles on noise priorities. The episode also touches on personal anecdotes, such as Mike's journey from mechanical engineering to his current role, and his passion for music and watches.

We are joined by our good friend John Cygnarowicz for the 3rd time for a wide-ranging conversation that touches on global perspective, finance, and professional discipline. We talk about John’s trip to Manila and the Philippines, discussing daily life and the extreme lengths many people go just to get to work, and how those realities contrast with what many take for granted. We also dive into the Bernie Madoff scandal, unpacking why the scheme lasted as long as it did and the structural and behavioral reasons it was eventually exposed. The conversation wraps around the CPA exam—what makes it uniquely demanding, what it signals about long-term commitment, and how it shapes careers in accounting and finance. The episode blends travel insight, financial history, and career perspective into a thoughtful, grounded discussion.

Pack your bags as we dive into Shiv’s latest adventures through the vibrant streets of New Orleans. We’re breaking down why these major hubs still hold magic while also revealing the best-kept secrets among America's most underrated cities. From hidden culinary spots to local travel hacks, this conversation is designed to inspire your next domestic getaway. We also pull back the curtain on what's coming next for The Sheddy Show as we look toward a massive year of growth. Get ready for a preview of our 2025 roadmap and a fresh perspective on exploring your own backyard.