The Sheddy Show

Serial entrepreneur Ed DuCoin joins the show to talk about four decades of building companies, starting with a telemarketing business he launched at 18 and grew onto the Inc. 500 thanks to a dialer his brother built at the dining room table. We get into how Orpical went from a tiny marketing agency to an AI-native operations firm, why growth for the sake of growth can sink a profitable business, a...

Software veteran Alex Trefilov joins the show to talk about a career that runs from BlackBerry to Amazon to an AI startup. He takes us inside BlackBerry when the iPhone launched, and explains why trying to win both business and consumer buyers at once helped sink the company. From there, it’s packing up his whole life for a four-week move to Seattle, working on Alexa, and building Amazon’s Prime A...

Angel Salazar joins the show a week after trading Chicago for Washington, DC. He looks back on eight years and seven neighborhoods in the city, why Pilsen felt most like home, and how growing up Mexican American in Springdale, Arkansas shaped him, from dirt roads to potato farms. Then we get into energy: why nobody thought about the power grid until AI data centers showed up, the story of his gran...

Shiv breaks down the Manchester City financial scandal: the 115 Premier League charges, the hacked emails that started it all, and why this Man United fan thinks a transfer ban beats relegation once you factor in what the club has done for East Manchester. That leads into Elizabeth Holmes, Theranos, and why white-collar prison time can look a lot like a getaway. Then it's our Q3 recap: best purcha...

Edgardo is back from Italy and ranks his trips so far: London, then Rome, Florence and Paris. We walk through 12 packed hours in Rome: the Sistine Chapel, a Colosseum still standing almost 2,000 years later, and the Trevi Fountain at 12:30 a.m. Then we slow down in Florence for the Duomo, the Arno and a hole-in-the-wall trattoria that beat Carbone. That leads into why London and New York have an e...

Ed and Shiv revisit their very first Bitcoin call from episode 15 (now up huge), break down the wild story of a fake NFL player who scammed 26 women out of over $1.3M, and go deep on AI slop flooding YouTube — plus why their alma mater NIU can't fill seats anymore

Special guest Mark Parages joins the show to talk about No Pain No Game, the card game he just released built around getting your friends off the couch and actually moving. We get into where the idea came from, how a deck of cards turns a normal hangout into something active, and what it took to go from concept to a finished product people can buy. From there the conversation heads to India. Mark...

Nola, a French-Moroccan project finance associate in energy who moved to the U.S in 2023, joins hosts Edgardo and Shiv to cover her adjustment to the US (weather, customer service, tipping), the contrast between French and American work-life boundaries, and why she has no plans to pursue US citizenship despite liking her life there, before moving into the professional side — the E-2 visa process,...

Edgardo and Shiv dig into the Miami vs. New York affordability debate sparked by a recent Bloomberg podcast, with Edgardo making the case for why Miami's rising costs don't tell the whole story compared to NYC. The conversation then shifts to the Fed, breaking down the latest FOMC meeting's decision to hold rates steady and what Kevin Warsh's ascension to Fed Chair could mean for monetary policy g...

Edgardo and Shiv kick off with a birthday check-in before digging into the state of consumer spending — pointing to rising credit card debt and a personal savings rate that's compressed from 6.2% to 4%, they make the case for a more K-shaped economy and predict food delivery and streaming subscriptions are first on the chopping block as households tighten up. That leads into a debate on whether AI...

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...