Jake Hurwitz

Men are struggling. And most of us are doing it silently. Welcome to The Optimist; a podcast for people who want to live bolder, deeper, and more emotionally connected lives. Hosted by Jake Hurwitz, this series is part confession, part conversation, and part rebellion against the two extremes of modern masculinity: the hyper-feminine “feel your feelings” camp and the toxic red pill chaos. There’s a third path. One where men can be grounded, vulnerable, funny, messy, ambitious, emotional, disciplined, and wild…all at once. Each week, Jake sits down with world-class thinkers, coaches, athletes, and artists to explore the stuff we don’t talk about enough: heartbreak, identity, fatherhood, freedom, failure, adventure, legacy, emotional intelligence, and how to actually be okay. It’s not therapy. But it’s close. And it’s not just for men. It’s for anyone who gives a damn about the men in their life. Whether you’re in the gym, on a solo hike, rebuilding after a breakup, or just tired of pretending everything’s fine, this is your invitation to start getting real. New episodes weekly. Subscribe and join the movement.

In this episode, Caleb Ulffers joins Jake Hurwitz to explore a powerful mindset shift: Everything is Easy. From embracing rejection and stepping fearlessly into new experiences, to optimizing your life with mindfulness, style, and authentic leadership, Caleb delivers practical insights you can apply immediately. Caleb shares his personal journey of growth, overcoming major setbacks, and building a fulfilling life through intentionality and relentless curiosity. Whether you're starting fresh or seeking deeper clarity, this episode offers tools to optimize your mindset and build a purposeful life.

Join Jake Hurwitz on The Optimist for a profound conversation with Lee Povey about men's groups, emotional intelligence, and modern masculinity. From his early work in therapy to founding transformative men's communities, Lee shares insights on helping men develop emotional awareness and authentic connections.Timestamps:2:38 - Early experiences with men's groups11:31 - Understanding feelings and emotional intelligence14:18 - History of masculinity and societal expectations23:52 - How to become a better listener37:33 - Creating healthy men's communities49:52 - Redefining masculinity and strength1:17:13 - Success stories from men's groups1:24:47 - What it means to be a man todayA must-listen for anyone interested in personal development, emotional intelligence, and building stronger relationships. Lee shares practical wisdom on leading with vulnerability while maintaining strength and purpose in the modern world.

Some of you asked for it; we needed zero excuse to record it. Have a listen to The Pit Wall, a Headgum original pilot! Headgum's Jake Hurwitz, Geoffrey James, Marika Brownlee, Andrew Pile and Casey Donahue discuss and recap the latest Formula 1 Grand Prix and all the little boys who drive the little cars. Join them as they recap the 2022 Belgian Grand Prix and discuss Lewis Hamilton's traipse through the Ardennes Forest, how Jake wants Toto Wolff to choke him, and where we think Daniel Ricciardo should go after this year. If you want more episodes of The Pit Wall, let us know by subscribing to and rating the show on Apple Podcasts and Spotify ! You can also tweet at us, but only if it includes your favorite photo of Guenther Steiner smiling. See omnystudio.com/listener for privacy information. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

This week on The Easy Chair, it’s Shoulda Swiped Left with Hannah and Jake. This is their final SSL podcast. For the last time on The Easy Chair they discuss Hannah’s on-line and current old-school matchmaker dating life. It’s the sweetest, funniest, most self-aware episode ever. Fact: I am going to miss this monthly podcast so much. For me, it was a chance to hear my wonderful kids speaking to each other openly and publicly about love and the unsinkable hope of finding it, through chance or technology. I got to know both Hannah and Jake in a different way, and one thing that I take away from the experience is the mutual respect and kindheartedness of their relationship. If you, like me, hate to see their conversations end, write to me at easychairpodcast@gmail.com suggestions for alternative directions Hannah and Jake might take. Travel? Politics? Any and all ideas are welcome. Next week: It's Mightier Than the Sword where Steph Spaulding and I take on how to start a blog with special guest and blog creator in progress Deborah Zervas. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today on The Easy Chair: It’s another candid episode of Shoulda Swiped Left with Hannah and Jake. It’s always a complete surprise to me what makes it onto the podcast, and this episode is no exception. Join us for a spirited and essentially unedited episode (we all had a busy week with only last-minute recording time) so enjoy the largely uncut content. And huge congratulations to Rana Othman, who won a dozen of Jake’s Mom’s Chocolate Chip Cookies by correctly identifying the ad-lib moment in last week's progressive Hurwitz family story. (It was when Jake called out “ciao, bitches”). Next week, Steph Spaulding and I will be back with an original short story by writer Keith Eldred. This week’s episode is brought to you by Squarespace. Whatever your website needs, check out Squarespace.com. If you’re like me, you’ll fall in love. In fact, I am using Squarespace for my own website, https://www.jakesmomscookies.com. Here's some additional incentive: when you’re ready to launch your site, just enter promo code easychair for 10% off! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on The Easy Chair: Shoulda Swiped Left Episode 20. That’s right, 20 episodes, and still, after all that time, Hannah and Jake never fail to surprise me. They share the same strange phobia (you’ll never guess). They talk dating, travel, waterfalls, and legit old-school matchmaking. It’s a uniquely freewheeling and enlightening episode, even by Shoulda Swiped Left standards. In fact, it is one of my all-time favorites. It isn't often you can say audio file editing was a pleasure, but this time, it was. Tune in and you’ll see what I mean. Next week: Mightier Than the Sword with co-host Steph Spaulding returns, and the week after that, another Hurwitz family progressive story (remember Trouble in Paradise?). For writing questions or dating stories, email me and Steph or me, Jake, and Hannah at easychairpodcast@gmail.com. We want to hear from you! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week, It's The Easy Chair episode 100!!! To mark this momentous podcasting milestone: Shoulda Swiped Left with Hannah and Jake. Of course there’s dating talk but also career talk, house talk, and a smattering of observations and opinions. My greatest joy as host and podcast editor is once a month, I get to appreciate the special dynamic between my two oldest kids. They might not always agree but they never fail to support each other. It’s a wide-ranging, relaxed, and largely unedited podcast. Celebrate with me by tuning in to this 100% genuine special anniversary episode. Next week, on Mightier Than the Sword: In preparation for sending our books out into the world, Steph Spaulding and I exchanged manuscripts to edit. We talk about the rules of engagement, when it comes to editing, and offer some advice to editors and those seeking editorial help. We also share our hopes and fears. As always, if writing advice is something you seek or would like to share, or if you have a dating story to tell, email us at easychairpodcast@gmail.com with Mightier Than the Sword or Shoulda Swiped Left in the subject line. We want to hear from you! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week’s episode: Shoulda Swiped Left, with Hannah and Jake. It has been a busy month in lots of ways and believe me when I tell you Hannah’s got stuff to talk about. The news is not all bad, but human relationships are never without complications. Jake and Hannah have different approaches to dealing with guys who go M.I.A.. You’ll see what I mean when you tune in to this interesting and enlightening episode. Next week: it’s a return to Mightier Than the Sword, the advice podcast for writers! Co-host Stephanie Spaulding has a question from an astrophysicist who hopes to try his hand at writing but is challenged by the prospect of creating character through dialogue. (One of our less orthodox suggestions: eavesdropping). We also have some slightly more socially acceptable strategies. As always, if you have dating stories or are seeking writing advice or the chance to add your two cents on either subject, send an email to easychairpodcast@gmail.com, with either “Shoulda Swiped Left” or “Mightier Than the Sword” in the subject line. We ALL want to hear from you! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It’s Shoulda Swiped Left #17, and it’s totally THE BEST. So much gets discussed: the virtues and rewards of being your true self. Breaking up, both badly and less so. Guilt. Ghosting. An earnest email from a fan with a link to …porn? Maybe we’re just confused. Join me, Hannah, and Jake for a super long, even more super worth it Shoulda Swiped Left episode that’s funny, real, and surprising. Next week: “Mightier Than The Sword” with Stephanie Spaulding. We’d love to take on your writing related questions! Send them to easychairpodcast@gmail.com, with Mightier Than the Sword in the subject line. Daters out there: same email address, with “Shoulda Swiped Left” in the subject line. We want to hear from you. This Easy Chair episode is brought to you by none other than Blue Apron. It’s the #1 fresh food delivery service for a reason! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.