Best The Pineapple Code Podcasts (2026)

1
Mezzanine 30:52

1h ago30:52

30:52

Host Jason uses the hotel mezzanine as a metaphor to explore social tiers in the ethical non‑monogamy community from the high‑visibility "shiny people" and secret side rooms to the lobby of newbies and burnouts. He reflects on inclusion, burnout, and how popularity often masks real connection. The episode validates different ways to engage, warns a…

1
Wildfires, Lawsuits, AI, and M&A: A Look Back at Insurance in 2025 | The Insurance Wrap-Up 20:31

10d ago20:31

20:31

Insurance Journal recaps the biggest stories of 2025, from record-breaking wildfires and climate losses to broker mega-deals, litigation reform, cyber threats, AI-driven layoffs, and signs of recovery in key insurance markets heading into 2026. Watch this end-of-year exclusive with Carrier Management’s Elizabeth Blosfield, Insurance Journal’s Ezra …

1
Come In, Come In: A Lifestyle Christmas Carol 31:32

13d ago31:32

31:32

Good morning, good afternoon, good evening. Jason connects Charles Dickens’ A Christmas Carol (via the Muppet version) to the lifestyle world, using the ghosts of past, present, and future as metaphors for memories, party energy, and long-term consequences. He shares personal holiday stories about raves, parties, shame, joy, boundaries, and communi…

1
Inside the 2025 Claims Digital Experience Study 2:34

14d ago2:34

2:34

A deep dive into JD Power’s 2025 Claims Digital Experience Study, revealing how customers use digital tools during the claims process and what makes those channels clear, helpful, and easy to use. To watch the full episode with host Don Jergler and J.D. Power’s Mark Garrett visit https://www.insurancejournal.tv/videos/26137/ The post Inside the 202…

1
Here Be Dragons 31:52

19d ago31:52

31:52

Jason uses a map-and-sea metaphor to unpack sexual dynamics in the lifestyle: desire, power, connection, and risk. He stresses clear communication, consent, and rejecting shame while exploring examples like FFM vs FMF, full swap nuances, and bisexuality. Practical takeaways include naming preferences, setting boundaries with partners, avoiding esca…

1
EP. 05: Digital Claims Experience Still A Work in Progress, But Pointing Up 12:44

21d ago12:44

12:44

Claims functionality in mobile apps is one of the biggest investment areas for carriers, which are seeing the fruits those investments continue to grow. New data show that customers using these digital claims reporting tools are more satisfied with the process. We spoke with Mark Garrett with J.D. Power about the intelligence firm’s new Claims Digi…

1
Marco Gorelli: Narwhals, ecosystem glue, and the value of boring work 51:41

21d ago51:41

51:41

You’ve probably used Narwhals without realizing it. It’s the compatibility layer helping apps and libraries like Plotly play nice with Pandas, Polars, Arrow, and more — while keeping computation native instead of converting everything to Pandas. In this episode, Marco Gorelli explains how his weekend experiment turned into essential ecosystem infra…

1
How to host a Meetup 50:22

26d ago50:22

50:22

Jason walks through everything you need to know to plan and host a lifestyle meetup, from choosing a venue and talking to managers to promotion, vetting, and managing the crowd. He covers public vs. private events, budgeting and ticketing, safety and discretion, dealing with problem attendees, and tips for welcoming newbies and building lasting eve…

1
Cracking the Code: How AI Turns Messy Insurance Docs into Underwriting Gold 3:42

27d ago3:42

3:42

In this episode preview with Kasey Roh, the U.S. CEO of Upstage AI, Kasey breaks down how AI-powered document intelligence handles messy loss runs and inconsistent supplemental applications, giving carriers a major speed and accuracy advantage in underwriting. Watch the full episode with Carrier Management’s Elizabeth Blosfield as host of the Insur…

1
EP. 16: The Whopper Lawsuit, Pineapple Drama & Insurance Legends Unite 39:55

30d ago39:55

39:55

Join our Golfertainment hosts George Jack, Patrick Wraight, and Kevin Amrhein alongside special guest Frank Pennachio—Florida insurance pro, author, Tampa Bay Rays fan, and all-around great conversationalist—as they dive into a festive mix of holiday cheer, standout insurance cases, and bold predictions for the year ahead. Frank brings wisdom, big …

1
‘Authenticity Travels Well’ 36:57

29d ago36:57

36:57

Jennifer Palmieri is chief people officer at Westfield, which certainly isn’t a regional p/c carrier anymore. She has witnessed growth in specialty lines and international risks. It’s nearing $5 billion in revenues and 4,000 employees. We checked in with Jen on how human resource strategies are playing out. “My leadership philosophy centers on auth…

1
Let's talk to the Flirty Pineapples 1:01:01

1M ago1:01:01

1:01:01

Host Jason sits down with Bella, a retired sex therapist, and her husband Prescott to share their origin story in the lifestyle, how they worked through jealousy, and the tools that strengthened their relationship. The episode covers practical advice for dating app profiles, privacy and validation tips, speed dates and travel strategies, and commun…

1
EP. 103: What Insurers Should Know About Banking for Cannabis Companies 19:14

1M ago19:14

19:14

Banking in the cannabis industry is a niche that few people may understand. It’s not without risk, but there are hundreds of banks offering their services to cannabis operators. In our latest episode, we talk to specialty banker Peter Su with First Central Savings bank about cannabis banking and what insurance and claims professionals should know a…

1
EP. 110: Solving Insurance’s ‘Document Chaos’ with Agentic AI 21:33

1M ago21:33

21:33

In this episode of The Insuring Cyber Podcast, Kasey Roh, U.S. CEO of Upstage AI, discusses how AI is transforming some of the most complex and time-consuming workflows in insurance. Kasey breaks down how Upstage’s document intelligence technology is aiming to reshape underwriting and claims operations, as well as the evolving balance between human…

1
Kelly Bodwin — Quarto hacks, AI in the classroom, and why R should stay weird 51:09

1M ago51:09

51:09

In this episode, we’re joined by Kelly Bodwin — candy corn defender, board game enthusiast, and Associate Professor of Statistics and Data Science at Cal Poly. We discuss her path from English and French to statistics, how she builds teaching tools and navigates AI in the classroom, and what it takes to keep a programming community weird in the bes…

1
Back from the Horizon: Returning to the Lifestyle 36:18

1M ago36:18

36:18

Host Jason returns from a spontaneous hiatus and shares a personal, candid journey through the lifestyle, using elevators and a stolen sailboat as metaphors for transitions, uncertainty, and self-discovery. The episode also serves as a primer on the lifestyle: foundational principles like consent, body positivity, and sexual freedom; practical advi…

1
How CISA Data Is Shaping Smarter Cyber Risk Decisions 1:57

1M ago1:57

1:57

CISA’s threat data helps companies and insurers sharpen their cyber-risk strategies by sharing real-time insights on attack patterns, emerging threats, and proactive defense tactics. Watch this sneak peek at the Insuring Cyber Podcast with host Elizabeth Blosfield and guest Brent Rieth of Aon – to watch the full interview visit https://www.insuranc…

1
Live from Applied Net: Geico and AI Observations 51:32

2M ago51:32

51:32

On this installment we tee up three segments from our onsite discussions at Applied Net 2025, a leading insurance tech conference held recently in Vegas. First: Why was the Geico Gecko basking in the crowd at an independent agent channel exhibit hall? This is intriguing! Take a listen as another direct-response carrier takes an interest in appointi…

1
EP. 109: The Future of Cyber Risk Without CISA: How Insurers and Businesses Can Adapt 17:00

2M ago17:00

17:00

Aon’s Brent Rieth discusses the ripple effects of the Cyber Information Security Act (CISA) not being renewed, warning that insurers now face a major data gap in assessing cyber threats and pricing risk. Without this vital information-sharing platform, both carriers and businesses must find new ways to access real-time insights into emerging attack…

1
James Blair: Part 2 — Solutions engineering, critical thinking, and staying human 42:09

2M ago42:09

42:09

This episode is Part 2 of our conversation with James Blair. He explains how he found his “accidental perfect fit” as a solutions engineer and how that role became a pipeline into product management. Get a peek into the AI-powered tooling he’s now building for the Posit ecosystem, and hear how he’s using Claude Code, Positron Assistant, and DataBot…

1
Care for Musicians 42:00

2M ago42:00

42:00

Yours truly has met many interesting people in my 43 years of hanging around the insurance business. Few are as fascinating, complex and rule-breaking as Peter Anderson. He leads a dominating musical instrument insurance program with 18,000 customers in the U.S. and around the world—90% of them arriving via the website. Listen to his origin story (…

1
Inside Allianz’s Cyber Report – Supply Chain Risks on the Rise 1:48

2M ago1:48

1:48

From ransomware to technical breakdowns, Allianz identifies supply chain disruptions as a major factor behind losses across manufacturing, retail, and professional services sectors. To watch the full interview with Caitlin Ewing, a complex claims analyst in cyber/financial lines with Allianz, visit https://www.insurancejournal.tv/videos/25973/ The …

1
James Blair: Part 1 — Portfolios, practice, and staying curious 29:31

2M ago29:31

29:31

In Part 1 of our conversation with James Blair, we trace his delightfully non-linear path from childhood robotics dreams to journalism to R, with a few stops in between. We hear about the Shiny app that changed his career, plus a candid roundtable with Michael, Hadley, and Wes about whether a data-science master’s still pays off in the age of AI. E…

1
EP. 04: Expert: Contingent Business Interruption Becoming A Bigger Player in Cyber Claims 14:30

2M ago14:30

14:30

Losses caused by a cyber event at a third-party location, somewhere along the supply chain or a key customer, have continued to big a bigger portion of cyber claims. According to Allianz, 6% of claim values were from contingent business interruption last year—this year that’s already up to 15%. “And I think it will continue to be a driver of claims…

1
Breaking Big Problems Into Smart Agents 3:03

2M ago3:03

3:03

Instead of relying on one giant model to do it all, insurers are now building interconnected AI agents that tackle complex insurance tasks step by step, delivering more reliable and scalable automation. Watch this clip from the Insuring Cyber Podcast as host Elizabeth Blosfield talks with John Kain, director of financial services market development…

1
Understanding the Best in People 44:47

2M ago44:47

44:47

Bringing out the best in workplace teams is a passion for organizational consultant Emma Corcoran. On this episode she outlines her journey at Selective Insurance to provide a shared customer experience program for appointed agencies as well as policyholders. Emma discovered the joy of helping teams evaluate customer research and outline actionable…

1
White Hot 30:36

3M ago30:36

30:36

Jason shares a candid, adult story from the lifestyle scene as he watches his wife shine at a rave, reflects on love, compersion, and growth in their relationship, and connects with a new friend. Between vivid moments of desire, vulnerability, and devotion, he announces a brief podcast break to recharge and promises to return with fresh stories and…

1
EP. 108: How Agentic AI is Supercharging the Insurance Workforce 17:28

3M ago17:28

17:28

In this episode, John Kain, director of financial services market development at AWS, shares how insurers are moving beyond traditional generative AI toward intelligent, autonomous workflows that can make decisions, execute tasks, and work together like human employees. From customer service and claims processing to training and onboarding, he says…

1
Julia Silge: Part 2 — Glue work, licensing, and open source in the age of LLMs 28:17

3M ago28:17

28:17

In part two of our conversation with Julia Silge, we discuss how work actually ships: the boundaries, the glue, and the tools that turn noise into signal. From there, we go macro and wonder what the LLM era means for humanity’s contributions, plus how licensing is evolving to protect sustainability without abandoning openness. Episode notes Both pr…

1
Lotus 47:20

3M ago47:20

47:20

Jason reflects on the transformative friendship with a woman he calls Lotus, sharing lessons about emotional space, setting boundaries, protecting your mental health, and navigating the complexities of the non-monogamous lifestyle. This episode blends personal confession, spiritual insight, and practical advice on asking for help, honoring feelings…

1
MGA No Longer a ‘4-Letter Word’ 50:10

3M ago50:10

50:10

Lloyd Yavener, president and COO of Sutton National Group, believes in the future of delegated underwriting authority. It wasn’t always that way. “MGA was a four-letter word when I first got into the business,” he says on this recording. “It was a broker model, which was to write more insurance, while the underwriter’s goal was to write more busine…

1
Spot! 33:34

3M ago33:34

33:34

Good morning, good afternoon, good evening. Wherever you are, this episode breaks down why your physical spot at lifestyle events matters and gives blunt, practical advice for meeting people: accept harsh truths (no one’s watching you), become memorable, use the Rule of Five, read groups, and—most importantly—change your spot to put yourself in the…

1
Julia Silge: Part 1 — Positron, pineapple pizza, and the art of iteration 38:45

3M ago38:45

38:45

In part one of our conversation with Julia Silge, astronomer-turned–data-science leader, we explore why data science needs a different kind of IDE. Julia takes us inside Positron, Posit’s next-generation, data-scientist-first environment, and unpacks the day-to-day realities that make data science work unlike software engineering. Along the way, we…

1
EP. 15: From Panic to Purpose: Finding Humanity in a Changing Industry (and on the Mini Golf Course!) 40:06

3M ago40:06

40:06

In this lively Golfertainment episode, hosts George, Kevin, and Patrick welcome inclusive leadership expert and author Amy Waninger to explore her new book Moving from Panic to Purpose – a candid, emotional, and inspiring guide to leading with empathy through change. Between heartfelt conversations about resilience, thoughts on the Ryder Cup, laugh…

1
AI Actuaries and the Next Frontier in Insurance 5:23

3M ago5:23

5:23

AI is moving beyond pricing models to transform insurance operations—especially claims, where automation can cut costs, speed decisions, and boost customer satisfaction. Alena Kharkavets – North American head of claims for WTW’s insurance consulting and technology business – joined to discuss the shift from AI assistants that handle day-to-day, sim…

1
I don't know 35:25

3M ago35:25

35:25

Jason recounts his weekend at the Pulsify takeover and shares the origin story of how he and his wife found the lifestyle, not for sex, but to build friendships and a social tribe after years of loneliness. He reflects on the emotional moment at the beach that started it all, the awkward early experiences, and lessons learned about communication an…

1
Humans and AI Fight Fraud Together 29:09

3M ago29:09

29:09

Claims fraud is getting more sophisticated. Carriers can fight back with AI to sift through huge amounts of data and find patterns, says Ashley Fong, VP with Carpe Data. Injury fraud thrives in areas where strong legal networks, high population density, heavy tourism, economic hardship, and legal loopholes create opportunities for fraudulent claims…

1
Michael Chow: From psychology and Python to constrained creativity 1:07:24

3M ago1:07:24

1:07:24

For this episode, we turn the mic around. Wes McKinney takes over the interviewer’s chair to chat with his co-host, Michael Chow. Michael’s a principal software engineer at Posit, but he started out studying how people think — literally, with a PhD in cognitive psychology. Somewhere along the way, he got hooked on data science, helped build adaptiv…

1
EP. 107: From Assistants to Actuaries, AI’s Next Leap in Insurance 22:57

4M ago22:57

22:57

On this episode of The Insuring Cyber Podcast, Alena Kharkavets – North American head of claims for WTW’s insurance consulting and technology business – joined to discuss the shift from AI assistants that handle day-to-day, simple tasks, to fully fledged AI actuaries and agents that are planning, decision-making and executing higher level tasks. WT…

1
the mundane 32:33

4M ago32:33

32:33

Host Jason reflects on late-night memories from the lifestyle, celebrating quiet, mundane moments—coffee, slow dances, shared jokes—that often mean more than the wild sexual adventures. Through personal stories, he explores how attention, friendship, and simple human connection deepen relationships in ethical non-monogamy and invites listeners to m…

1
SPG’s Jonah Lipin on AI, Broker Relationships & New Wholesale Division | WSIA Conference 3:34

4M ago3:34

3:34

At the WSIA Annual Marketplace, Peter Van Aartrijk, host of the On Point podcast by Insurance Journal, sits down with Jonah Lipin, Chief Sales Officer at SPG. They discuss how brokers value personal contact with underwriters even as AI enters the industry, and how technology can enable faster, more effective communication without replacing human ex…

1
From AI Hype to Business Outcomes: A Practical Playbook for CMOs | Ragnarokast #22 34:57

4M ago34:57

34:57

Navigating the world of AI can be overwhelming. In this episode of Ragnarokast, we're tackling the big questions with two leaders in the industry: Apply Digital’s Chief Strategy Officer, Lauren Milne, and Chief Technology Officer, Scott Michaels. They share practical advice on where to start, how to spot the difference between AI fantasy and realit…

1
WSIA Annual Marketplace: Peter van Aartrijk Interviews Mary Rimbey, Cardinal E&S 3:49

4M ago3:49

3:49

At the WSIA Annual Marketplace in San Diego, Peter van Aartrijk, host of the On Point podcast by Insurance Journal, interviews Mary Rimbey, VP of Wholesale National Distribution at Cardinal E&S. They explore why AI is an efficiency tool rather than a threat, how broker-underwriter relationships remain the backbone of the industry, and where opportu…

1
Progressive’s Core Values Guide Decisions 45:32

4M ago45:32

45:32

On this installment we visit with the HR pro who oversees a team fielding tens of thousands of job applications each year at Progressive. Neil Lenane joined the carrier 35 years ago. His love of coaching sports got him interested in a career in human resources. “Leadership carries over to sports and HR. You’re recruiting that talent, onboarding, co…

1
Gifts, Pineapples & Pleasure: The Ultimate Lifestyle Present Guide 32:40

4M ago32:40

32:40

Jason celebrates his birthday by sharing playful, practical gift ideas for friends in the lifestyle, from discreet sex toys, robes, and squirt blankets to themed pineapple keepsakes and thoughtful non-sex gifts. He also stresses STI testing with a recommendation for discreet at-home kits and offers do's and don'ts for giving without pressure or exp…

1
Defining AI Risk: A Key Challenge for Insurance Regulators 1:50

4M ago1:50

1:50

In this Insuring Cyber podcast excerpt, the discussion highlights one of the biggest hurdles facing insurance regulators: defining the type of risk AI presents. Regulators are taking a risk-based approach, recognizing that not all risks are the same, with special attention on areas such as life insurance, unfair practices, and algorithmic bias. A m…

1
Hot Tequila 30:53

4M ago30:53

30:53

In this raw, unfiltered episode, Jason shares a personal breakdown and recovery from mental health struggles within the lifestyle community. He explores themes of anxiety, disordered attachment, therapy, the challenges unique to the lifestyle, and the importance of honest communication and support. My links: www.thatotherlifestyle.com https://benab…

1
U.S. AI Action Plan vs. EU AI Act: Competing Approaches to Global Leadership 1:53

4M ago1:53

1:53

In this Insuring Cyber podcast highlight, the discussion shows the key contrasts between the U.S. and EU strategies for artificial intelligence. The U.S. AI Action Plan is positioned as a forward-looking roadmap designed to establish America as a global leader in AI innovation, infrastructure, diplomacy, and security. In contrast, the EU’s AI Act t…

1
Young Founder Seeks Insurance ‘Transparency’ 44:31

4M ago44:31

44:31

Could insurance providers forge a new bond of trust with policyholders? Valkyrie Holmes, age 21, is working toward that better world. She founded an insuretech called Faura to help carriers collect more verifiable data on property risk in disaster-prone areas. The industry currently relies primarily on often-outdated data sources. Instead, Faura en…

1
Tariffs, Supply Chains, and Inflation: Challenges Ahead for Insurance Claims 1:46

4M ago1:46

1:46

In this Claims Journal Podcast excerpt with Paul Kottler, U.S. president — global technical service, with Crawford and Company, he discusses the mounting pressures on the insurance claims sector as global events ripple through supply chains. From tariffs and public unrest to ongoing wars and extreme weather, these factors are driving material cost …

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