Best Total Conundrum Podcasts (2026)

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Episode 73 - Kelly Blackheart 1:25:56

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25d ago1:25:56

1:25:56

Today we sit down with the incomparable Kelly Blackheart — also known as Kelly Zabielski — whose journey is nothing short of fearless, hilarious, and wildly inspiring. Kelly has lived multiple lives: from playing collegiate volleyball to working in renewable-energy finance, to acting in commercials and appearing on MTV… all before pivoting hard int…

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Open Source Outside the Box 25:24

8d ago25:24

25:24

Open source has always played a big role at 37signals. This week, Jason Fried and David Heinemeier Hansson share why they’re drawn to working in the open, and how that mindset carries into their newest product, Fizzy. Key Takeaways 00:12 – Why open source continues to matter at 37signals 05:12 – Sharing work publicly pushes quality higher 09:55 – H…

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When is enough, enough? 17:34

15d ago17:34

17:34

There’s a moment in every product where you have to stop tweaking and actually launch. This week, Jason Fried and David Heinemeier Hansson reflect on how 37signals decides when a product is truly ready for its first release. They share how they think about simplifying, sharpening, and ultimately knowing when it’s time to ship. Key Takeaways 00:12 –…

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Picking Pricing 35:12

22d ago35:12

35:12

How do you land on the right price for a product? This week, 37signals co-founders Jason Fried and David Heinemeier Hansson pull back the curtain on the pricing choices they’ve made over the years, including the options the public never saw. They talk about why chasing giant enterprise deals isn’t for them, and why simple, steady pricing beats clev…

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Monsters, Metaphors & the Midwest: An Interview with Minnesota Author Patrick W. Marsh 1:08:35

1M ago1:08:35

1:08:35

This week on Total Conundrum, we sit down with Minnesota author Patrick W. Marsh, creator of The Greenland Diaries series and a master of monsters both real and symbolic. We dive into:• How Patrick builds terrifying (and emotional) creatures• Using monsters as metaphors for mental health• His writing process and creative rituals• Minnesota’s unique…

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Episode 71 - Inside the Oman House: Hauntings, Hollywood & Hellish Encounters with David Oman 1:31:37

2M ago1:31:37

1:31:37

Tonight, we’re taking you straight into one of the most haunted houses in America — The Oman House, perched just steps from the infamous Sharon Tate murder site on Cielo Drive. We’re joined by paranormal investigator and homeowner David Oman, who’s spent over two decades documenting and living among intense supernatural phenomena. David spills behi…

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Out of Office, Together 29:48

1M ago29:48

29:48

Twice a year, the entire 37signals team meets up in person. This week, co-founders Jason Fried and David Heinemeier Hansson talk about how these gatherings work, what they’re really for, and why the structure is intentionally loose. They share how the mix of optional hangouts and focused work sessions helps their fully remote team reconnect, rechar…

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Episode 70 - Spirit Guides & Healing with Deborah Roque of Paranormal Paradigma 1:30:17

2M ago1:30:17

1:30:17

In this transformative episode of Total Conundrum, we welcome Deborah Roque—a medium, healer, and the visionary behind Paranormal Paradigma. With over 20 years in education and a lifetime of spiritual experiences, Deborah shares how she transitioned from academia to spirit work, what it’s like to collaborate with Spirit Guides, and how we can all b…

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Soft openings aren't just for restaurants 14:48

2M ago14:48

14:48

This week, the team shares a behind-the-scenes look at how they bring in outside beta testers before a product launch. Jason Fried and David Heinemeier Hansson share how they invite early users into the mix, what they’re looking for, and how it all shapes the final version. It’s a rare peek into the “guests are coming over” phase of building Fizzy.…

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The itch for a new version 23:08

2M ago23:08

23:08

In software development, there are updates, and then there are complete overhauls. This week, Jason Fried joins Kimberly Rhodes to talk about how the team decides when it’s time to rebuild from the ground up. They dig into the transition between versions, how customer feedback fits in, and even drop a few hints about what’s coming in Basecamp 5. Ke…

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Fizzy Q's and A's 26:36

2M ago26:36

26:36

With the launch of Fizzy getting closer, 37signals co-founders Jason Fried and David Heinemeier Hansson use this episode to answer listener questions about the upcoming product. They talk about how Fizzy and Basecamp will coexist, why aesthetic design choices matter, and which AI features are actually worth using. Key Takeaways 00:11 – Fizzy and Ba…

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Episode 69 - Ty Olsson 2:35:54

2M ago2:35:54

2:35:54

Grab your favorite salt rounds and a flask of vampire blood, Conundrum Crew — because this week, Jeremy and Traci sit down with the legendary Ty Olsson! You know him as Benny Lafitte from Supernatural, Niko Zimmer from The 100, and the unforgettable Original Dragon from Dragon Tales (yes, seriously — that’s range!). Ty opens up about life behind th…

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Revisiting the good old days 16:27

2M ago16:27

16:27

Time has a way of reshaping what we believe, and sometimes, what we’ve published. In this week’s episode, CEO and co-founder Jason Fried chats with Kimberly Rhodes to explore one particular chapter of REWORK that no longer rings true. Jason reflects on their current stance on having multiple products vs. just one, what company's should consider bef…

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Episode 68 - Bridging Worlds: Rob Gutro on Spirits, Pets & the Afterlife 1:04:11

3M ago1:04:11

1:04:11

In this chilling and heartwarming episode of Total Conundrum, Jeremy and Traci welcome Rob Gutro — medium, paranormal researcher, and author of several books on spirits and the afterlife. Rob has a unique gift: he communicates not only with human spirits, but also with pets who’ve crossed over.From exploring the science of energy to sharing moving …

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Traditional marketing doesn't work for us 30:09

3M ago30:09

30:09

For 37signals, flashy ad campaigns and traditional brand promos have never been the way to go. This week, Jason Fried and David Heinemeier Hansson share why traditional marketing methods like billboards, paid social media posts, and keyword ads don’t give them results. They talk about how meaningful marketing comes from genuine support and real con…

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Episode 67 - The Roff House Gets Conundrum’d, TWATTED, and Screamed At 1:42:19

3M ago1:42:19

1:42:19

In this extra-special crossover, we’re teaming up with T.W.A.T.S. (The Wisconsin Apparition Tracking Society) and our paranormal podcast friends over at I Scream You Scream to bring you a chilling and hilarious deep dive into one of America’s first documented spirit possession cases — the infamous Roff House in Watseka, Illinois. We unpack the eeri…

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Built on Trust 27:59

3M ago27:59

27:59

Trust is the foundation of any strong company. In this episode of The REWORK Podcast, 37signals co-founder and CTO David Heinemeier Hansson joins host Kimberly Rhodes to explore what it really means to build a high-trust organization. David shares how trust shapes the culture and success of a team, even when working remotely. Key Takeaways 00:23 – …

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Refining before release 24:43

3M ago24:43

24:43

As 37signals gets closer to launching their newest product, Fizzy, Jason Fried joins host Kimberly Rhodes to reflect on the final stretch of development. He shares the trade-offs of setting your own deadlines, the importance of onboarding new customers, and the company's process for marketing a product. Key Takeaways 00:11 – What the “11th hour” lo…

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Episode 66 - Worlds Most Haunted Island 1:04:07

3M ago1:04:07

1:04:07

This week, we’re teaming up with our creepy-cool neighbor from Wisconsin — Star from Creepy Shit Podcast! She’s joining us to share her favorite kind of nightmare fuel: the chilling history and hauntings of Poveglia Island, Italy’s most cursed speck of land. We dive into the dark past of plague pits, tortured souls, and paranormal investigations th…

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Escaping Workaholism 21:39

3M ago21:39

21:39

In their book REWORK, 37signals' co-founders Jason Fried and David Heinemeier Hansson caution against glorifying nonstop work. In this week's podcast, they tackle a listener's questions related to the chapter Workaholism and dig into employee management including how to measure productivity and how to track progress. They explain why simple convers…

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Episode 65 - Locked Up, Lost Souls: The Secrets & Spirits of Alcatraz 1:05:24

4M ago1:05:24

1:05:24

What do Al Capone’s ghost, a raincoat raft, and a haunted prison hospital have in common? They’re all part of the chilling history of Alcatraz—“The Rock.” Join Traci & Jeremy as they dive into the eerie past and lingering paranormal of America’s most infamous prison. From failed escapes and ghost banjos to cold spots in solitary confinement, this e…

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Finding focus 24:12

4M ago24:12

24:12

Curious how Jason Fried and David Heinemeier Hansson keep their attention where it counts? In this episode of The REWORK Podcast, the 37signals co-founders join host Kimberly Rhodes to talk about the different ways they approach focus. From procrastination that sometimes pays off to meditation and visualization, Jason and David share their tips for…

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Episode 64 - Sealed in Tragedy: The Chicago Tylenol Murders 58:44

4M ago58:44

58:44

In 1982, a wave of terror swept across Chicago—not with a gun or a knife, but with something found in nearly every medicine cabinet: Tylenol. In this emotionally charged deep-dive, Traci and Jeremy walk through the heartbreaking, minute-by-minute unfolding of the Tylenol murders.From 12-year-old Mary Kellerman’s tragic collapse to the devastating l…

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Episode 63 - Ghosts, Gadgets, and the Midwest: Chatting with Dave from Midwest Spirit Seekers 1:00:01

4M ago1:00:01

1:00:01

Join us as we talk with Dave from Midwest Spirit Seekers — one of the most passionate and experienced paranormal investigators in the Midwest! In this episode, we explore haunted locations, discuss the most effective paranormal equipment, and hear about some truly spine-tingling experiences. Dave opens up about the realities of ghost hunting, from …

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Total transparency 17:59

4M ago17:59

17:59

37signals' co-founders Jason Fried and David Heinemeier Hansson share more about their business than many founders. In this episode of The REWORK Podcast, they chat with host Kimberly Rhodes about why transparency is important to them. They talk about how sharing openly can double as marketing, the upside of showing work that's still in progress, a…

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Episode 62 - The Van Meter Visitor: Iowa’s Winged Nightmare 39:24

4M ago39:24

39:24

In 1903, the quiet little town of Van Meter, Iowa, got a visit from something strange — an eight-foot, bat-winged, bulletproof, sulfur-smelling nightmare with a glowing horn. And no, this isn’t a rejected Marvel villain. Jeremy and Traci dig into one of Iowa’s strangest cryptid tales — The Van Meter Visitor. From eyewitness accounts and old newspap…

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It Started with a Blog 24:52

4M ago24:52

24:52

37signals' co-founders Jason Fried and David Heinemeier Hansson revisit how their approach to marketing began with a simple blog. They share why writing with authenticity matters, how patience pays off when building an audience, and why staying true to your own voice is important. Key Takeaways: 00:12 – How 37signals' marketing started organically …

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Episode 61 - The Unsolved Murder of Missy Bevers: A Chilling Case of Deception and Mystery 43:01

5M ago43:01

43:01

Description:Before dawn on April 18, 2016, fitness instructor and devoted mother of three, Missy Bevers, arrived at Creekside Church of Christ in Midlothian, Texas, ready to lead her early-morning Camp Gladiator boot camp. But within minutes, she was brutally murdered by an unknown figure dressed head-to-toe in SWAT-style tactical gear. In this epi…

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Building with LLMs, Finding a Co-founder & Other Listener Questions 25:54

5M ago25:54

25:54

Jason Fried and David Heinemeier Hansson sit down with host Kimberly Rhodes to field a fresh round of listener questions. They share perspectives on when coding assistance makes sense, finding a co-founder to compliment your skills, business succession planning, and more. Key Takeaways: 00:17 – When AI coding tools help vs. when they get in the way…

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Episode 60 - The Ariel School UFO Encounter: 60 Kids, One Unforgettable Day in Zimbabwe 44:05

5M ago44:05

44:05

Description:September 16, 1994 — Ruwa, Zimbabwe.Sixty-two schoolchildren ran screaming across the playground, claiming they had just seen something that would haunt them for the rest of their lives. Silver discs in the sky. Small black-clad beings with massive eyes. And a telepathic warning about Earth’s future. No adults saw it. But the kids’ stor…

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Titles, tenure, and paths don't matter 25:51

5M ago25:51

25:51

In this episode, 37signals co-founders Jason Fried and David Heinemeier Hansson talk about why résumés, job titles, and career timelines take a back seat to what really matters when hiring — your actual work. They share how real-world examples cut through the noise, and open doors for people who may not have a traditional path. Key Takeaways: 00:00…

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The Final Episode 1:09:05

5M ago1:09:05

1:09:05

Cousin Sal is joined by the D3 and former producers, Jim Cunningham, Tate Frazier, and Babyface Joel Solomon, to bring the podcast to an end. Hosts: Cousin Sal, Darren Szokoli, Brian Szokoli, Harry Gagnon Producer: Michael Szokoli The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and help…

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NFL and NCAA Future Bets 1:13:01

5M ago1:13:01

1:13:01

Sal and the D3 give out futures for the upcoming NFL (7:37) and NCAA (32:50) season before giving out betaches from this weekend (57:29). Hosts: Cousin Sal, Darren Szokoli, Brian Szokoli, Harry Gagnon Producer: Michael Szokoli The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and helpline…

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BONUS EPISODE: 37signals is moving to Omarchy 35:07

5M ago35:07

35:07

In this bonus episode of REWORK, 37signals' co-founder and CTO David Heinemeier Hansson shares his exploration into Linux, development of Omarchy, and the company's decision to go all-in. Key Takeaways: 00:43 – David's exploration into Linux and development of Omarchy 04:27 – How Omarchy is different, Hyprland, and tiling windows managers 11:05 – T…

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Against All Odds Rewind with David Wright and Eric Allen 43:53

5M ago43:53

43:53

In today's episode we look back at two Hall of Fame interviews with Mets legend, David Wright, and NFL legend Eric Allen. Hosts: Cousin Sal Guest: David Wright, Eric Allen Producer: Michael Szokoli The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and helplines available, and listen to th…

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Software as art 23:50

5M ago23:50

23:50

This week on The REWORK Podcast, 37signals' co-founders Jason Fried and David Heinemeier Hansson explore a listener question about approaching software as art. They discuss the importance of having a point of view as you're building products. Key Takeaways: 00:15 – Great software helps customers see things from the creator’s perspective 07:31 – A c…

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Against All Odds Rewind with The Miz and Jeff Ross 37:37

5M ago37:37

37:37

In today's episode, we look back on two great interviews from this past year that featured The Miz and Jeff Ross. Hosts: Cousin Sal Guest: The Miz, Jeff Ross Producer: Michael Szokoli The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and helplines available, and listen to the end of the e…

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Balancing it all 29:55

5M ago29:55

29:55

37signals' co-founders Jason Fried and David Heinemeier Hansson are back behind the mic with host Kimberly Rhodes. This week, they’re discussing balancing personal interests, health, and hobbies with business success. They discuss building a healthy company without it taking over your life. Key Takeaways: 01:12 – Why business health is all about ba…

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The State of Sports Betting With Todd Fuhrman 55:17

6M ago55:17

55:17

Todd Fuhrman joins Sal to discuss the state of sports betting across the U.S., including when it might be legalized in California. Hosts: Cousin Sal Guest: Todd Fuhrman Producer: Michael SzokoliThe Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and helplines available, and listen to the en…

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Episode 59 - Carroll Edward Cole: The 8 Year Old Serial Killer 42:57

6M ago42:57

42:57

He was just eight years old when he killed for the first time… and no one noticed. In this episode of Total Conundrum, Jeremy and Traci unravel the disturbing life of Carroll Edward Cole, a serial killer whose crimes went undetected for decades—despite confessions, hospital warnings, and chilling early behavior. From his traumatic childhood and ear…

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The Baseball Hall of Fame, New York's Best Baseball Players, and a Career in Stand-up 46:48

6M ago46:48

46:48

Sal is joined by MLB writer Rob Parker to discuss the Baseball Hall of Fame, the best players in Yankees and Mets history, and his stand-up career. Hosts: Cousin Sal Guest: Rob Parker Producer: Michael Szokoli The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the resources and helplines available, and …

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Best of Cuz's Conundrums | Cousin Sal's Winning Weekend 52:41

6M ago52:41

52:41

We revisit the best of the 'Cuz's Conundrums' segment from season 2! Host: Cousin Sal Producers: Michael Szokoli, Joel Solomon, Jack Wilson, Sirushi Witte, Jonathan Frias, Drew Van Steenbergen, Felipe Guilhermino, Oscar De La Luz, Chris Wohlers The Ringer is committed to responsible gaming, please visit theringer.com/RG to learn more about the reso…

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Favorite Football Win Total and the British Open with Paul Koehorst 1:15:29

6M ago1:15:29

1:15:29

Sal and the D3 recap the Home Run Derby, go over their favorite win total bet for the NFL (11:50) and NCAA (21:24), and are joined by Paul Koehorst to give out their best bets for the British Open (31:09). Hosts: Cousin Sal, Harry Gagnon, Darren Szokoli, Brian Szokoli Guest: Paul Koehorst Producer: Michael Szokoli The Ringer is committed to respons…