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, and the time a racing school offered him a full refund to go home before he got behind the wheel.

From there we dig into what separates an entrepreneur from a business owner, whether you need Michael Jordan–level drive to succeed, and how an employee earns their way to co-founder. Ed also shares how he’d use AI to stress-test whether you’re ready to leave a corporate job, why the journey beats the Ferrari, and why 24-year-olds should already be building a voice as thought leaders.

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 Air drone delivery program, including why drone delivery still struggles in big cities and makes more sense in rural and suburban areas. We get into what AI is really changing for software developers, why critical thinking matters more than ever, what “vibe coding” gets wrong, and why bosses now expect a month of work done overnight. Alex also shares how he evaluates startups as an investor, makes the case for why VR and AR glasses are the next step after smartphones, and tells us about his AI music project, Veiled Vessels, on Spotify.

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 grandfather raising money for shovels to bring electricity to a tiny town in Oaxaca, and why slow permitting and paper-based processes are holding up new projects. Angel and Eddy also break down how electricity actually gets priced, using a highway traffic jam to explain it, and why the UK does it differently.

From there we turn to AI. Angel explains why DeepSeek is his favorite outside of Claude, how to run a model locally on your own laptop, and why privacy makes that worth the effort, with Shiv adding the client confidentiality angle. We close with what finance was really like before 2008 and Angel’s take on why information is becoming one of the most important commodities.

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 purchase (a custom tux and an $80 marriage certificate), best trip (Vegas), biggest lesson (take the early flight, and simple systems beat elaborate ones), and worst decision (an Xbox collecting dust and a summer of overspending before the wedding). Plus, the time AI turned a 15-minute task into 45, and a quick correction on the Florence Duomo.

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 energy no other city matches. Back in the States, we react to the Fed's 25-basis-point rate hike and ask whether it touches what we actually feel, like a nearly $3,000 iPhone Duo. We close on the new Siri AI finally being useful, why it could win over AI skeptics, and why it's worth taking the AirPods out now and then.

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 walks us through his time in Bengaluru — the food, the pace of the city, the tech scene, and the things that surprised him most about living and working there versus visiting.

We hit on AI: where it's actually useful right now, what's hype, how it's already reshaping work, and where we each think things are headed over the next few years.

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, why she chose Chicago over the Middle East for utility-scale renewable projects, and the differences between financing large utility-scale deals versus smaller distributed generation and community solar — then into energy policy, touching on France's nuclear-heavy grid versus aging infrastructure across Europe, the case against full privatization of utilities, and how AI data centers are driving new demand and making the energy sector "sexy" in both the US and France, before closing on lighter cultural observations (French leisure vs. American urgency, tipping norms, WeChat's all-in-one integration in China) and travel recommendations for Morocco, Albania, China, Chile-Bolivia-Peru, and the south of France.

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 going forward. The episode wraps with a lighter, rapid-fire round covering a mix of fun and whimsical questions.

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 subscriptions are next: Shiv argues frontier model subscriptions (Claude, ChatGPT, Gemini) are largely recession-proof while task-specific tools built on top of them are the real risk, and the two riff on the Japanese aggregator model Sakana Fugu as a possible future test case. They close out with a World Cup wrap-up, reflecting on Spain vs. Argentina in the final, England's surprise run, and a few hot takes on the tournament's biggest storylines.