The Sheddy Show
by Edgardo Jove
Shiv Kapoor and Eddy Jove have decided to take their POD public. We cover everything on this Podcast from sports, to finance, to everyday life; so if you wanna listen to two guys who are starting off their corporate journey, tag along with us for the ride, it should be a fun one.
Episodes
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Entrepreneurs vs. Business Owners: Ed DuCoin | EP 158
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…
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BlackBerry, Amazon Drones & AI Coding: Aleksej Trefilov | EP 157
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...
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Angel Salazar: Power Grid, DeepSeek & Local AI | EP 156
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...
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Man City Scandal, Prison Perks & Our Q3 Recap | EP 155
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,...
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Florence, the FED & the iPhone Duo | EP 154
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…
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Episode 15 Redux: Bitcoin, Daejon Love & the AI Slop Problem | EP 153
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
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Mark Parages on No Pain No Game, India & Where AI Is Headed | EP 152
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…
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Nola on the E-2 Visa, Renewable Energy, and Life as a French Expat in Chicago | Ep. 151
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...
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Miami Money, Flat Rates & Warsh's Fed | EP 150
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...
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Streaming Cuts, AI Subscriptions & the World Cup Final | EP 149
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...
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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)…
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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…
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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.…
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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...
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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…
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Iran War Economics, Grid Constraints & the U.S.-China AI Race | EP 143
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…
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Stop Sleeping on AI: Kacper Rutkiewicz on Claude, Small Business, and Why the Window Is Closing | EP 142
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,...
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Michael Bockwoldt | EP 141
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...
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John Cygnarowicz #3 | EP 140
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…
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USA Travel Guide: New Orleans Hidden Gems, San Francisco Tips & 2025 Plans | EP 139
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...
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Hollywood's Billion-Dollar Bidding War and The Secret Cost of Getting Older | EP 138
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…
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Discipline, Deals & Decentralization | EP 137
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.
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Griffin Lynch | EP 136
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...
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Why Running Hurts and LinkedIn Feels Boring | EP 135
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.
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Texas Is Booming, Dallas Is Shaking, and Scottsdale Is Rising | EP 134
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...
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Nik Champion #2 | EP 133
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...
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Devynn Dominguez | EP 132
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.
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Jeanie Buss Sells the Lakers — The End of an Era | EP 131
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…
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Communism in New York City | EP 130
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
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Are Woolly Mammoths Back? | EP 129
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
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Bridget Mendler, Trump vs Harvard, Anti-Fragile | EP 128
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…
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Anthony Mazzenga | EP 127
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,...
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WARREN BUFFETT RETIRES | EP 126
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…
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Chad Mogan | EP 125
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...
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Kyle Lim | EP 124
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...
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ASHTON HALL, WHAT ARE TARIFFS, LOSING WEIGHT IN LONDON | EP 123
We dive into Ashton Hall, discussing his use of saratoga water and this new wave of alpha male mentality. Next, we take an in-depth look at tariffs and free trade, breaking down how tariffs impact economies, businesses, and consumers. We debate their effectiveness, considering both protectionist...
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Greg Wittstock | EP 122
We sit down with Greg Wittstock, aka The Pond Guy, to dive into the world of backyard water features, entrepreneurship, and scaling a niche business into a multi-million-dollar enterprise. Greg, the founder of Aquascape, shares how he turned his childhood passion for ponds into a dominant brand…
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PLTR, OPEN AI DEEP RESEARCH, JUSTIN ISHBIA | EP 121
In this episode of The Sheddy Show, we dive into the world of investing with a breakdown of Price-to-Earnings (P/E) ratios—how they work, when they matter, and whether they’re still relevant in today’s market. Then, we shift gears to discuss the latest in OpenAI’s deep research, covering recent...
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KANYE'S BACK, PODCAST REVIEW | EP 120
In Episode 120 ofThe Sheddy Show, we take a deep dive into Kanye West's latest tweets, dissecting the content, the potential implications on his public image, and how they fit into the larger conversation on celebrity influence in today's social media-driven world. We explore whether his words…
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SILK ROAD FOUNDER FREE, NYC CONGESTION PRICING, JFK FILES | EP 119
This installment of The Sheddy Show dives into the big issues shaping headlines, from the debate over NYC's congestion pricing plan to the far-reaching impacts of Trump’s executive orders. FOLLOW US: @thesheddyshow
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Reis O'Donnell #2 | EP 118
Reis O'Donnell returns for a second appearance! We dive into Reis's adventures across Europe, sharing stories from his travels. We also discuss the excitement building around the 2026 World Cup and reflect on the implications of the Palisades fire. Tune in for a mix of personal stories, global...
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DUB APP, LESSONS LEARNED, 2024 RECAP | EP 117
The episode explores the dub app, discussing its features, potential applications, and significance in their professional or personal lives. Drawing from Shiv's recent three-month immersion in India, the host shares valuable lessons and cultural insights gained from his experience. As a highlight...
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Dylan Gilbert #2 | EP 116
In this episode of the Sheddy Show, host Sheddy welcomes back special guest Dylan Gilbert, marking his second appearance on the podcast. Dylan, who has recently joined Team USA as a member of the World Cup Bobsled team, shares his journey to this prestigious position and reflects on the…
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SINGAPORE, AMERICAN CLUB, 50 MILLION DOLLAR LOSS | EP 115
We explore a mix of intriguing topics: a deep dive into the vibrant city of Singapore, the exclusive world of the American Club in Hong Kong, and the story behind Ken Griffin's loss on his iconic Chicago penthouse. Tune in for a blend of global insights, luxury, and real estate!
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Connor Onak | EP 114
Sheddy welcomes Connor Onak, a professional in software sales who shares his inspiring personal development journey. Over the past few years, Connor has experienced significant growth and transformation, positioning himself in an exciting place both professionally and personally. The conversation...
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DONALD TRUMP, DUBAI WHIPS, PUERTO RICO | EP 113
Tune in to episode 113 of the Sheddy Show as the hosts discuss the recent United States election and its implications for the nation. Shiv shares his experiences in Dubai, offering insights into the vibrant culture and lifestyle of the city. Meanwhile, Edgardo reflects on his time in Puerto Rico,...
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BOEING 777, COSTCO GUYS, STOCKNEWS.AI | EP 112
In this discussion, we dive into the cultural and economic differences between the USA and India, exploring what factors might influence someone’s decision to live in either country. The conversation highlights the unique lifestyle, job opportunities, and societal norms that shape everyday life…
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FOREVER WARS, VOTE WISELY, BARSTOOL SPORTSBOOK | EP 111
In this episode, we dive into the vibrant contrasts between Delhi and Bengaluru, exploring their unique cultures, lifestyles, and economic landscapes. We then shift gears to discuss Dave Portnoy and the evolution of Barstool Sports, examining how his entrepreneurial spirit has shaped the brand…
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LIVING IN INDIA FOR 3 MONTHS, DIE WITH ZERO, SHOTSPOTTER | EP 110
Shiv is currently immersing himself in the diverse culture of India for the next three months, and he shares valuable insights from his experiences. We also examine key ideas from Bill Perkins' Die With Zero, which advocates for prioritizing meaningful experiences over the accumulation of wealth....
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RIOTS IN THE UK, JAPAN's MARKET BUST | EP 109
Join us as we delve into the turmoil of the recent UK riots, uncovering the root causes and their wider social implications. Then, we pivot to dissect last week's sudden crash in the Japanese stock market. What set off this financial shockwave, and what could it mean for the global economy? Tune…
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About this show
Shiv Kapoor and Eddy Jove have decided to take their POD public. We cover everything on this Podcast from sports, to finance, to everyday life; so if you wanna listen to two guys who are starting off their corporate journey, tag along with us for the ride, it should be a fun one.
Hosted by
Edgardo Jove
Categories