The Sheddy Show

Bosnia, Crash Reports & Feral Hogs: Reis O'Donnell | EP 148

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.

Goals, Bans & Blockchain | EP 147

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.

The $50K Average, Amex vs. Airlines & Spirit's Bankruptcy | EP 146

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.

AI Agents & Career Agility: Adam Leber (Morningstar CCO) on the Future of Work | EP 145

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.

One Year After Liberation Day + America's Most Over & Underrated Cities | Ep. 144

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.