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The Daily Checkout Podcast

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Hosted by seasoned industry insiders Jeremy Gant and Jason Kibby, each episode brings you inside the world of hospitality: the good, the bad, and the absolutely bizarre. From interviews with hotel executives and managers to deep dives into brand strategy, operations, staffing, revenue management, tech, and guest service trends — this show delivers the real talk behind the front desk.
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Chicago’s daily news podcast, fresh every weekday at 6 a.m. Host Jacoby Cochran brings you timely conversations with news and culture makers; activists and artists; bus drivers and students; those who love and hate this place—all in 15 minutes a day. It’s a smart and delightful new way to connect with the city we share. Learn more and subscribe to our morning newsletter at citycast.fm/chicago.
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The Retail Podcast

The Retail Podcast

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Retail reinvents itself daily. The Retail Podcast arms founders, operators, and retail technologists with battle-tested tactics to outpace change. Each week candid conversations with store chiefs, DTC disruptors, and tech visionaries reveal how to turn AI, data, and culture into margin and loyalty. No jargon just hard numbers, honest lessons, and plays you can run before next Monday. Press play; lead the future of commerce.
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Pooche’s Picks

Pooche’s Picks

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Welcome to Pooche’s Picks Daily Fantasy Football Podcast hosted by two high school students from Long Island, NY named Aaron (Schnitz) and Jason. Each week we will go through the best players at each position, the best value players to include on your week’s roster depending on your strategy, the best match-ups to exploit, and of course, our own personal picks of the week. Be sure to checkout each week’s podcast for the best tips to win!!!
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Brian, Winston, and Tony talk anal sensor nerves, more brainrot, punchbaby, touch starvation, para social relationships, tango spin world records, bigger taller skeletons, manosphere, not a Bob, Thor, vanity watches, and nut cream master. Original music by DeJuan Boyd of Rabbitt Productions. podcastxwhyz.podbean.com twitch.tv/podcastxwhyz instagram…
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M&S launches a dedicated resale shop on eBay (with Reskinned), the ONS delays July retail sales to 5 Sept, TikTok Shop’s GMV Max becomes the only supported campaign type, Sainsbury’s begins a facial‑recognition trial, Lush closes UK stores for a day in solidarity with Gaza, and Charlotte Tilbury drives experiential shade‑matching at John Lewis and …
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Five Things Friday — APAC edition. Guest Ryf Quail (NRF: Retail’s Big Show APAC) breaks down why retail media in APAC is set to lead globally, then we dive into Thailand’s mall renaissance, Uniqlo’s recycling roadmap, MUSINSA×ANTA’s China JV, and Urban Revivo’s global expansion. Chapters below. Sources and links at the end. Subscribe for weekly, no…
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For the last few weeks, the Trump administration has increased threats to send National Guard Troops to Chicago. Now we are getting word that the administration has notified the Naval Station Great Lakes, an hour north of Chicago, that it will serve as a command station for forthcoming ICE operations during Mexican Independence Day celebrations. Ax…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Corti has shifted its focus to providing AI models, tools, and data center capacity to other healthcare AI companies, amid concerns about job loss due to automation in industries like software development and customer service. Studies show a de…
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Four years ago, Chicago launched Crisis Assistance Response and Engagement (CARE) teams. Initially made up of police officers, paramedics, and mental health professionals, the goal was to deescalate emergency calls that involved mental health. But a new series shows results of the pilot have been mixed, with funding and bureaucracy issues, and that…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.In a recent Google antitrust case ruling, a federal judge decided that Google does not have to sell off key assets like its Chrome web browser, although it must share some search data with competitors. The ruling acknowledged the impact of rapi…
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Catching the end of farmers market season was near the top of our list in our September guide. That makes it a good time to revisit these advanced tips for Chicago farmers markets. Earlier in the season, host Jacoby Cochran, executive producer Simone Alicea, and social media manager Rick Homuth discussed some common mistakes and how to make the mos…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world. Corti, a Danish medical AI company, has shifted its focus to providing AI infrastructure for healthcare applications, partnering with organizations like VoicePoint to offer services such as diagnostic support. The CEO believes that specialized…
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It’s after Labor Day, which means for some of us it’s already fall while others are trying to hold on to summer. Host Jacoby Cochran, executive producer Simone Alicea, and Chicago artist Al Scorch discuss what they are looking forward to in September, including Chicagohenge, the Bears’ return, and pumpkin spice offerings. Plus, they’re watching som…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.##Title: Google launches new AI tool to detect skin conditionsGoogle recently announced the launch of a new AI tool that can detect over 288 skin conditions. The tool, called Derm Assist, can analyze images of skin conditions and provide a list…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Transitioning from the Labor Day weekend, the tech world saw the launch of a new super PAC focused on AI policy and regulation called Leading the Future. Companies like HP and Nvidia released their tech earnings reports, while public figures li…
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Five Things Friday UK Edition with Simone Oloman UK retail news this week: Aldi boosts wages, Topshop returns to Liberty, Asda expands Express, JD Sports shares rise, and The Very launches an immersive fashion experience. Aldi: link Topshop: link Asda: link JD Sports: link The Very Group: link 👉 Subscribe for weekly UK retail insights. 00:00 Intro …
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Chicago Public Schools has yet to place about 200 students with disabilities in classrooms, despite it being the second week of school. While the district says it is working quickly to place students in cluster programs, we ask Chalkbeat Chicago education reporter Samantha Smylie how families are managing this waiting period. Plus, Injustice Watch …
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US retail news: Walmart marketplace AI and next‑day delivery, Gap’s denim push, Best Buy’s refurb engine, Cracker Barrel’s logo U‑turn, plus A&F × NFL. Subscribe for weekly retail strategy. American Eagle’s latest ambassador buzz & denim wars Gap’s creative burst and the renewed denim cycle Best Buy repairs/refurb: sustainability with margins Crack…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Nvidia is focusing on data center sales, introducing technology like Spectrum-XGS to connect smaller data centers. The company is preparing for various scenarios in the future of AI, including the potential for an "AI winter" or a shift towards…
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APAC retail briefing: LABUBU/Pop Mart’s blind‑box momentum, China’s Gen Z wellness shift, Australia Post’s US‑parcel pause (de minimis), “dopamine village” malls in PH, and JD.com’s new Dubai warehouse. Subscribe + comment with your action. LABUBU/Pop Mart = modern playbook: scarcity, social currency, collaborations (host commentary). Gen Z wellnes…
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With the threat of the National Guard looming over the city, it’s important to remember immigration raids are still happening across Chicagoland. Host Jacoby Cochran talks with Diego Morales with the Pilsen Rapid Response Network about how organizers are responding and what Chicagoans should do if they encounter ICE operations. Want some more City …
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world. The secondary market for venture capital (VC) has seen significant growth, reaching $61.1 billion in the second quarter of 2025, according to PitchBook. Secondaries have become a vital part of the private markets, allowing VC firms to generate…
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There’s still at least a few weeks left in patio season, which means there’s still time to meet some patio dogs. Bringing your dog to a restaurant patio or brewery has become a more common sight in Chicago, but what are the rules? City Cast contributor Leigh Giangreco talked with diners, dog owners, and restaurant workers in Roscoe Village to learn…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Microsoft AI CEO Mustafa Suleyman has expressed concerns about "seemingly-conscious AI" (SCAI) that imitates consciousness to the point of being indistinguishable from truly conscious beings. The rise of conversational AI with empathy and memor…
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Kaave Pour (ex‑SPACE10/IKEA) breaks down the home as retail’s #1 touchpoint: from layered home systems to utilities as technology (heat pumps, batteries, air/water quality), the Matter standard, robots, renting vs. owning, and how energy economics reshapes behaviour. You’ll learn: The home stack:structure → furnishings → utilities → interfaces/data…
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President Donald Trump is reiterating threats to send National Guard troops to Chicago. A new report indicates they could come as soon as September. Host Jacoby Cochran and executive producer Simone Alicea discuss how local leaders are responding. Plus, they discuss the city’s progress (or lack thereof) on its Vision Zero goals, and they play Raddl…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Robinhood is currently embroiled in lawsuits over its attempt to allow customers to invest in sports outcomes through prediction markets. The platform Kalshi, supported by Sequoia, has already won a court case permitting it to offer political-b…
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In 2000, Chicago Mayor Richard M. Daley unveiled the “Plan for Transformation,” a decade-long initiative that demolished Chicago’s public highrises, overhauled the city's public housing system, and displaced thousands of Chicagoans. Author Natalie Moore and investigative reporter Mick Dumke have both covered the legacy of the Plan for Transformatio…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Private equity dealmaking in the aerospace and defense sector saw a significant 32% decline in Q2, according to PitchBook. This drop is attributed to tariffs and broader geopolitical uncertainty, leading to a surprising slowdown in defense deal…
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Glossier joins TikTok Shop, Adidas rewrites nostalgia, back‑to‑school spend pulls forward, Prime vs Walmart deals, UK ultrafast delivery, loyalty reboots, agentic AI pilots, France’s “Drive,” Mango’s stylist AI, Gulf luxury momentum, Reliance x Shein, live commerce scale. Welcome to a four‑region special of Five Things Friday. USA with Jill Dvorak …
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Brian, Winston, and Tony talk dial up shut down, hanging out at the salt mines, Moleman warfare, Pit Boss Grappling, roll for series, limited supply or time, Shelly in the courtroom, profiled by AI drive thru, and smoking skinny cigs. Original music by DeJuan Boyd of Rabbitt Productions. podcastxwhyz.podbean.com twitch.tv/podcastxwhyz instagram.com…
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As Chicago Public Schools return for the 2025-2026 school year, major questions remain, like the future of the CPS budget gap, protections for immigrant students, and the relationship between the governor and district leaders. WBEZ Education reporter Sarah Karp and freelance journalist Brandon Pope are here to break down the pressing challenges fac…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world. An MIT report found that 95% of AI pilot projects fail due to a "learning gap" in how companies implement AI tools, rather than limitations of the technology itself. The report recommended creating more agentic AI systems using the Nanda proto…
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The city’s House Music Festival and Conference is back, which means it’s time for a dance break. We’re revisiting a conversation we had in 2022 with the co-hosts of WNUR’s Vintage House Show, DJ Lori Branch and archivist Lauren Lowery, about the roots of house music, the legacy of the now-landmarked Warehouse, and modern reinterpretations of the ge…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Tether, a stablecoin giant, has hired top Trump crypto advisor Bo Hines in an effort to distance itself from past controversies. Despite being a successful company with a $167 billion market cap, Tether has faced accusations of opacity and comp…
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Steve Dolinsky made his name as ABC7’s “Hungry Hound” before retiring as NBC5’s “The Food Guy” earlier this year. This weekend, he’s bringing Pizza City Fest back to Chicago after a disastrous run two years ago. Dolinsky tells host Jacoby Cochran what’s new this year and hesitates to say if Chicago is still the country’s greatest pizza town. Plus, …
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.The text discusses Sam Altman's contradictory statements on AI, warning of a bubble in the market while planning trillions in OpenAI's buildout. Despite concerns, OpenAI has raised record funds. Tech giants like Microsoft and Meta are investing…
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Heavy rain over the weekend left thousands without power while streets, highways and basements continued to deal with flooding. Host Jacoby Cochran and executive producer Simone Alicea discuss an effort to install new flood detection systems across the city. Plus, we’re covering the latest stadium news for the Fire and Bears, and exploring Chicago'…
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Good morning from OWITH.ai, the podcast that gives you only what's important to hear in AI and tech world.Fintech and crypto companies are engaging in a battle over open banking rules, with a shift in power dynamics in Washington D.C. The financial technology industry is evolving rapidly, with new players and technologies reshaping the landscape of…
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Our city, our schools, and our transit system are all in a budget crisis. University of Chicago professor and director of the Center for Municipal Finance, Justin Marlowe, tells host Jacoby Cochran why Chicago’s public institutions are all feeling financial pressure and where these structural deficits come from. We’re doing our annual survey to lea…
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From AI-powered supermarket lanes to shifting consumer habits, Alexandra Boisson & The Retail Podcast team unpack Europe’s retail trends. In this Five Things Friday – EU Edition, Alexandra Boisson and Alex from The Retail Podcast dive into the latest shifts in the European retail market. We cover: Colruyt’s Easy Checkout: AI-powered cameras speedin…
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From Currys’ Action AI rollout to Space NK’s Willy Wonka-style flagship, this week’s top UK retail stories. In this summer edition of Five Things Friday, Alex from The Retail Podcast is joined by Simone Oloman (Co-Founder, NIFT) and Dave to unpack the hottest retail stories in the UK right now. We cover: Store closures & uncertainty — Claire’s admi…
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After growing concern and anxiety about how Chicago Public Schools would close a $700 million deficit before the end of August, we finally got our first look at the district’s 2026 budget proposal. We are breaking down the key points with author and professor Arionne Nettles and Block Club Chicago’s Atavia Reed. Plus, will the Uptown Theatre ever g…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Meta had a strong second quarter, with significant revenue growth and surpassing analyst expectations. The company's core advertising business remains robust, fueled by heavy investments in artificial intelligence. Mark Zuckerberg's increased A…
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We’re midway through August. School’s starting next week. Maybe you feel like summertime Chi is winding down. But not so fast, our host Jacoby Cochran and Hey Chicago newsletter editor Emmi Mack are describing their most Chicago day. Wanna see these spots on a map? Check out our list on Overlook. Want some more City Cast Chicago news? Then make sur…
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Good morning from OWITH.ai: the podcast that gives you only what's important to hear in AI and tech world.Rebecca Lynn, a seasoned venture capitalist, advises against being a first mover in the market. Instead, she recommends being a second mover and watching where the market is going to come in with a better product and marketing strategy. Lynn fo…
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Local Style Chips is a homegrown snack that pays homage to classic Chicago foods, such as Italian beef, deep-dish pizza, and the Chicago hot dog. Earlier this year, host Jacoby Cochran and producer Michelle Navarro tested the potato chips when they started to hit Chicago shelves to find out if they’re any good. They talked to Local Style founder La…
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