The Sheddy Show

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...

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...

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 gu...

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 less...

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 mi...

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 d...

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...

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 car...

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...

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...

Edgardo and Shiv dive deep into the media landscape's most explosive story: the Paramount hostile takeover bid for Warner Bros. Why does their offer crush Netflix's, and what does this mean for every major studio? Then, we get personal. Discover how both hosts are navigating the practical realities of age—from daily routines to long-term career goals—and unpack the concept of getting older in a wo...

We dive into the shrinking sneaker resale market, break down the pros and cons of Bitcoin, and talk about what it really takes to pursue the CFA exam. From discipline and long-term thinking to market cycles and crypto risk, we cover it all.

In Episode 136 of The Sheddy Show , we sit down with Griffin Lynch — writer, storyteller, and computer scientist — for a conversation that blends creativity, data, and big-picture thinking. Griffin walks us through his creative writing process and gives a behind-the-scenes look at the book he’s currently working on publishing. We dive into the world of fiction, discussing reading trends, genre dem...

We’re talking movement — on two wheels, on foot, and online. From marathon training to the freedom of biking, and why LinkedIn sometimes feels like it’s standing still, this episode explores how to keep momentum when everything else feels static.

Texas is quickly staking its claim as the new capital of corporate headquarters, and we break down the tax benefits, lifestyle factors, and big-name moves driving the shift. We also unpack the blockbuster Micah Parsons trade and what it signals for the Cowboys’ future. To wrap it up, we head to Scottsdale, Arizona, spotlighting its growing reputation as a hotspot for both leisure and long-term liv...

We sit down with Nik Champion to talk about the journey of growing his insurance brokerage and the lessons learned along the way. We get into the M&A landscape within the insurance industry , the challenges and opportunities of scaling, and how leadership evolves as a business expands. Beyond business, Nik opens up about fatherhood and balancing family life with entrepreneurship. We also touch...

Episode 132 of The Sheddy Show features Devynn Dominguez, wedding content creator and fiancée of Edgardo. Devynn shares how she built her business capturing candid, behind-the-scenes moments at weddings, her favorite stories from past events, and tips for couples to make the most of their big day.

The Lakers have officially changed hands. Jeanie Buss, after decades of family control, has sold the franchise — and the ripple effects are just getting started. We break down what this means for LA, the NBA, and the high-stakes world of sports ownership. Then it’s over to the points game: American Express is still the king of perks... or is it? We unpack what’s real value, what’s just vibes, and...

Hope you had a fantastic fourth! This episode we talk a new Kobe documentary, Zohran Mamdani's bid for NYC mayor and the implications, and Shiv's recent trip to Maine. FOLLOW US: @thesheddyshow

The OG duo talks MIT research on AI and its impacts on the brain, Colossal Biosciences and their mission to bring back the Woolly Mammoth, and Weddings! FOLLOW US: @thesheddyshow

In Episode 128 of The Sheddy Show , we kick things off with Bridget Mendler’s surprising transition from Disney Channel star to aerospace entrepreneur, diving into how she’s helping launch Northwood Space and what it signals about the future of talent in tech. That momentum carries us into a charged discussion on Trump vs Harvard, where we unpack the broader implications of elite institutions clas...

In this episode of The Sheddy Show , we sit down with Anthony Mazzenga to chat about his role at FM , where he dives into the world of risk engineering and the unique challenges that come with protecting commercial properties from loss. Anthony shares what it's like living in Madison, Wisconsin , offering insights on the local culture, lifestyle, and how it compares to other places he’s lived. We...

We dive into our recent trip to Omaha, Nebraska for the legendary Warren Buffett Annual Shareholders Meeting —a.k.a. the "Woodstock for Capitalists." We talk about everything from our experiene road tripping to Omaha, to Buffett and Greg Abel's thoughts on Berkshire's future, balance sheets, and the company you keep around you. Follow US: @thesheddyshow on all platforms

Today on The Sheddy Show, we chat with Chad Mogan, a seasoned sales representative in the roofing and renovation world. We break down the real-life struggles of navigating insurance, explore the ins and outs of the roofing business, and take a surprising detour into the world of trading cards. A great conversation blending business insights and personal passions. Follow our guest: @chad_mogan Foll...

We’re joined by Kyle Lim , CEO of Power Dental Group , a second-generation dental manufacturing company. Kyle shares his journey of taking the reins from his father, stepping into leadership, and carving out his own path while honoring the company’s legacy. The conversation dives into the evolution of Power Dental’s product development, what it takes to innovate in a traditional industry, and the...