The Sheddy Show

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.

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.

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.

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 demand deficit. They wrap with real AI use cases — Shiv's custom workout agent, Eddy's Claude-powered podcast research system — and land on a shared take: AI won't end the world or steal your job, but how fast you learn to use it will define who pulls ahead in the next decade.

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 to get real results. We explore why Kacper has become such a strong advocate for the Anthropic ecosystem and dive into real-world use cases across each platform. Beyond his content creation, Kacper runs Deep Rooted AI, a consultancy helping small business owners integrate AI into their products and workflows — meeting them where they are and building sustainable, AI-powered systems that don't require a technical background to maintain.

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 cars, and discusses the impact of electric vehicles on noise priorities. The episode also touches on personal anecdotes, such as Mike's journey from mechanical engineering to his current role, and his passion for music and watches.

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 Bernie Madoff scandal, unpacking why the scheme lasted as long as it did and the structural and behavioral reasons it was eventually exposed. The conversation wraps around the CPA exam—what makes it uniquely demanding, what it signals about long-term commitment, and how it shapes careers in accounting and finance. The episode blends travel insight, financial history, and career perspective into a thoughtful, grounded discussion.

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 coming next for The Sheddy Show as we look toward a massive year of growth. Get ready for a preview of our 2025 roadmap and a fresh perspective on exploring your own backyard.

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 world obsessed with youth.

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 demographics, and what actually draws different audiences to particular stories.From there, the conversation shifts into tech and markets: we break down the influence of the “Magnificent 7,” the accelerating role of AI in both creative and corporate worlds, and even touch on Michael Burry’s macro takes. It’s an episode that connects imagination with analysis — perfect for anyone interested in how storytelling and technology shape each other.

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 living.

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 on the impact of AI in insurance—from efficiency gains to the way technology is reshaping client relationships.A mix of business insight, personal growth, and future-focused conversation.FOLLOW US: @thesheddyshow

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 how to actually win with your card in 2025.We wrap with a quick hit on the credit score debate: what happens to landlords if FICO fades away?Follow us on IG, TikTok, and X @thesheddyshow for extra takes and behind-the-scenes moments.

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 clashing with populist figures and what it reveals about the state of American discourse. We then explore the concept of being “antifragile,” drawing from Taleb’s work to look at how individuals and systems can actually benefit from disorder—whether in markets, careers, or daily life. Throughout the episode, themes of reinvention, disruption, and long-term thinking take center stage. To ground it all, Edgardo shares where he’s at in his CFA study grind, breaking down what’s working, what’s overwhelming, and why consistency is proving to be the real edge. His insights tie back to the antifragile mindset—leaning into challenge, not avoiding it. The episode moves fast but hits deep. One for the thinkers, hustlers, and anyone reworking their playbook.

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 also take a trip down memory lane to his high school days, where he earned the title of salutatorian, and reflect on the habits and mindset that got him there. It’s a laid-back but thoughtful convo about careers, growth, and finding your rhythm post-grad.

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_moganFollow us: @thesheddyshow

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 realities of running a family business. Kyle also talks about his relationship with entrepreneur and investor John Cerasani, and how that connection has influenced his growth as a young business leader.Whether you’re into entrepreneurship, family business stories, or behind-the-scenes insights from a niche industry—this one’s worth a listen.

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 and free-market perspectives. Are tariffs necessary safeguards or economic barriers? We analyze the historical context and modern implications. Finally, we follow Edgardo’s journey in London, and Shiv's journey in Mexico.Tune in for a thought-provoking mix of pop culture, economics, and personal anecdotes!

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 in the industry, helping homeowners and landscapers create stunning aquatic ecosystems.FOLLOW GREG: @GregWittstockthepondguy FOLLOW US: @thesheddyshow

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 advancements, potential use cases, and what the future of AI innovation might look like. And of course, we wrap things up with a chat about Chicago sports—the highs, the lows, and everything in between. Tune in for another packed episode of finance, tech, and sports!🎧 Listen now on your favorite podcast platform! #TheSheddyShow #Investing #OpenAI #ChicagoSports

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 are a form of self-expression or part of a calculated strategy to stay relevant in the ever-changing pop culture landscape.Additionally, we switch gears and reflect on the evolution of the podcast itself. We review past episodes, highlight our favorite moments, and discuss the direction we see the show heading as we continue to explore topics ranging from politics to global trends to cultural phenomena. It's a more introspective episode, with plenty of insights on what’s coming next forThe Sheddy Show.Tune in for candid commentary, analysis, and a look at the state of the podcast after 120 episodes!

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

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 events, and insightful commentary! FOLLOW US: @thesheddyshow

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 of the episode, they conduct a retrospective review of 2024, reflecting on the year's most significant moments, personal growth, and key learnings.

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 confidence and athletic prowess that have propelled him to success in his sport.The conversation delves into Dylan's experiences in bobsledding, discussing the rigorous training and mental fortitude required to compete at such a high level. He also expresses his deep ties to Chicago, highlighting how the city has influenced his athletic career and personal development. Throughout the episode, Dylan's passion for representing the USA and his love for his hometown resonate strongly, making for an inspiring discussion about ambition, community, and the drive to excel in sports. FOLLOW OUR GUEST: @dylgil15 FOLLOW US: @thesheddyshow

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!

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 delves into India's emerging economic potential, exploring growth sectors, technological innovation, and the country's evolving role in the global economy. Additionally, they discuss Bitcoin, covering current market trends, institutional adoption, future price predictions, and the regulatory landscape surrounding the cryptocurrency. FOLLOW OUR GUEST: @Connor Onak - Linkedin FOLLOW US: @thesheddyshow - Instagram & TikTok

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, sharing his perspective on the island's unique challenges and resilience. FOLLOW US: @thesheddyshow

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 in both nations. We also tackle the monopoly held by Boeing in the aerospace industry, examining the implications of their dominance on innovation and competition. Additionally, we chat about the popular TikTok duo, AJ and Big Justice, known for their entertaining takes on Costco shopping and the value of bulk buying. The conversation touches on insights from StockNews.ai, emphasizing how data-driven analytics can guide investment decisions in today's fast-paced market. Tune in for a nuanced exploration of these intriguing topics! FOLLOW US: @thesheddyshow

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 and its impact on sports media. Finally, we tackle the complex topic of America's "forever wars," analyzing the implications of prolonged military engagement on both foreign policy and domestic perspectives. Join us for an engaging conversation that weaves together these diverse themes! FOLLOW US: @thesheddyshow

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. In addition, we provide a comprehensive update on developments in Chicago, focusing on the implications of ShotSpotter technology for community safety. Lastly, Edgardo offers a detailed overview of the real estate market, highlighting current trends and investment opportunities. This discussion provides a thoughtful exploration of personal growth, financial philosophy, and urban dynamics. FOLLOW US: @thesheddyshow

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 in for an insightful exploration of these urgent developments shaking both society and markets. FOLLOW US: @thesheddyshow

Eddie shares a new musical revelation. The boys discuss the Paris Olympics and some of the fun events that the've seen so far. In other news, Celsius (NASDAQ: CELH) gives the fellas some love this week, and the crew discusses the future of Bitcoin from the recent bitcoin confrence and the implications of a future with a bitcoin currency reserve.

Things heat up with one of our rare disagreements! We dive into the big news of the week: Joe Biden's unexpected announcement to step down as the Democratic nominee. What does this mean for the upcoming election and the political landscape? We also switch gears to sports, discussing the latest season of "Hard Knocks" featuring the New York Giants. We break down the Saquon Barkley contract fiasco and its impact on the team. Tune in for a lively debate and all the latest updates! FOLLOW US: @thesheddyshow

We delve into the recent assassination attempt on Trump's life, exploring the implications and reactions. We also take a deep dive into personality tests, discussing our results and what they reveal about our traits and behaviors. Additionally, we tackle the tricky topic of hiring and firing friends, sharing advice on navigating these challenging situations. Join us for an insightful and engaging discussion on these diverse and compelling topics! FOLLOW US: @thesheddyshow

In a recent episode of The Sheddy Show, the hosts tackled a variety of topics, starting with effective strategies to achieve a shredded physique. They emphasized the importance of combining strength training with cardio exercises, highlighting high-intensity interval training (HIIT) and steady-state cardio as the best types to complement strength workouts and enhance fat loss. The discussion then shifted to the media portrayal of Chicago, often focusing on crime and negative aspects, and included a comparison with Los Angeles, noting the differences in lifestyle, culture, and public perception between the two cities. Additionally, the hosts shared recommendations of great books they have read recently, offering insights and takeaways from their personal reading lists, which provided listeners with a variety of book suggestions across different genres and themes. Overall, the episode combined fitness advice, cultural commentary, and literary discussions, giving listeners a well-rounded and informative experience. FOLLOW US: @thesheddyshow

In Episode 104 of The Sheddy Show, we welcome special guest Andrew Freed to discuss his incredible journey in real estate investing. Andrew shares how he scaled his portfolio from a single condo to an impressive 180 units in just three years. The conversation covers essential topics such as multifamily investing, where Andrew highlights the benefits and challenges, and the key factors to consider when selecting properties. They also delve into the strategic use of Home Equity Lines of Credit (HELOCs), with Andrew explaining how he leveraged home equity to finance his ventures, the associated risks, and practical tips for investors. Furthermore, Andrew offers a detailed look at his approach to rapid portfolio scaling, emphasizing the importance of networking, mentorship, and continuous learning. Filled with success stories, lessons learned, and actionable advice, this episode provides valuable insights for both seasoned investors and newcomers. FOLLOW US: @thesheddyshow

The Sheddy gents dive into several intriguing topics in episode 103. We start by discussing Keith Gill and the GameStop fiasco, exploring how Gill's online posts and the subsequent Reddit-driven stock surge turned Wall Street on its head. The conversation then shifts to the concept of luck, with compelling arguments presented both for and against its existence. Finally, the hosts examine the electric vehicle craze, analyzing its rapid global adoption and the factors driving this significant shift in the automotive industry. The episode offers a blend of financial insights, philosophical debate, and technological trends. FOLLOW US: @thesheddyshow

In the recent episode of The Sheddy Show podcast featuring Luis Hernandez, a well-known entrepreneur and real estate investor, several engaging topics are discussed. Luis shares insights on flipping homes in Baltimore, highlighting the unique opportunities and challenges of this market, and discusses his ventures in buying apartment complexes in Denver, detailing the strategies and considerations involved in such investments. He also recounts his recent attendance at a Berkshire Hathaway event, discussing key takeaways and the importance of such events for industry knowledge and networking. Additionally, listeners are encouraged to check out Luis's own podcast, The Wayfinder Show, and to follow The Sheddy Show on TikTok and Instagram at @thesheddyshow

In this captivating episode of The SHEDDY Show, we sit down with the inspiring Kalan Green to delve into his remarkable journey through the tech giants, Meta and Google. Kalan shares his experiences working at these leading companies, providing an insider's perspective on the dynamic world of big tech. We explore Kalan's expertise in mastering algorithms, uncovering the secrets behind some of the most influential algorithms shaping our digital lives today. Kalan's deep understanding and innovative approaches offer valuable insights for anyone interested in the tech industry. In a poignant segment, Kalan recounts a touching story of compassion and humanity. He shares his experience of giving $100 to a homeless felon, a gesture that not only changed the recipient's day but also left a lasting impact on Kalan. This heartfelt story highlights the importance of kindness and the powerful ripple effects of small acts of generosity. Join us for this enlightening and moving episode as we navigate the intersections of technology, personal growth, and the human spirit with the incredible Kalan Green. Tune in to The SHEDDY Show for more inspiring conversations and thought-provoking discussions!

EPISODE 100! Thank you everyone for tuning in and listening to 100 episodes of the Sheddy Show. We saw your favorite guest episodes this past year and decided to combine them both in this special roundtable format podcast! The boys discuss some of the happenings in Chicago, upcoming world sporting events like the world cup and the olympics, and we discuss being single along with pros and cons it brings. Follow our GUESTS: @aedgar_ @kyle_lietz Follow US: @thesheddyshow

Enjoy this short unreleased clip from episode 99! Let us know what you think is better, ChatGPT or Co PILOT!

How are you all enjoying the shorter podcasts? Let us know in the comments of our social media pages below! Follow US: @thesheddyshow

Finance, finance, and more finance! We discuss SBF’s sentencing, the ways markets work and how they are fueled, and if lack of flood insurance kills property value.