From Skateboards to Boardrooms: How a CEO Paved Her Way to Her Dream Job

For many of us, following our passions doesn’t always pay the bills. But sometimes, the right idea (and a little grit) can change that. In this special episode created in partnership with Capital One Venture X Business Card, we sat down with Kristen Dermer, a CEO who took her childhood passion for skateboarding and turned it into a career. Kirsten, the co-founder of Spohn Ranch, told us all about how she built her award-winning skatepark design-build business from the ground up. Click play, lean back, and prepare to get inspired.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Josh Allen and Hailee Steinfeld are expecting their first child together. Hailee shared the news in her “Beau Society” newsletter. But Josh Allen kinda gave it away with his empathic morning sickness on the sidelines. We wrap the last episode of the year with our annual Wellies, including categories like “Most Exhausted PR Team” and “Diva of the Year.” Disagree with the nominees? Sound off in the comments. In this episode of Well Played, we also cover:  An update on the Sherrone Moore case out of the University of Michigan  Why motherhood made Olivia Culpo mourn who she was before having her baby How Ann Michael Maye’s “Bakemas” killed Drake Maye’s win Why we’re not surprised A’ja Wilson is a co-chair for the Met Gala’s host committee  Introducing the greenest flag in college football, Fernando Mendoza Thanks to our presenting sponsor Capital One Venture X Business Card! Visit ⁠https://skimmth.is/48YzMGy⁠ to learn more. Well Played will be on winter break for the next few weeks. Until then – thank you for all of the support in 2025. This show would be nothing without you! See you in the New Year, love you mean it byeeeeeeee! - Blake & Caroline Follow Olivia Culpo on IG: @oliviaculpo  Follow Olivia Culpo on TikTok: @oliviadangerculpo Follow Blake on IG: @blaaakkkke Follow Caroline on IG: @cghendy Follow theSkimm on IG: @theskimm Learn more about your ad choices. Visit megaphone.fm/adchoices

The hottest show in sports right now has nothing to do with quarterbacks or point guards, but it has everything to do with gay guys who play pro-hockey – and we’re into it. Blake recaps the hockey smut show, Heated Rivalry, while Caroline breaks down the Notre Dame college football playoff drama, à la Regina George and the Plastics. Plus, the WTA’s no. 4 tennis player, Amanda Anisimova, drops by the studio to chat about going pro at 15, what happened when she prioritized her mental health, and more.  In this episode, we also cover: The Chiefs sh*tting the bed in front of the girl gang, aka: Taylor Swift, Selena Gomez, and Lena Dunham Alix Earle and Braxton Berrios calling it quits  The effectiveness of the positive vibes bunny in the Eagles locker room  Which game NFL fans dubbed “Pookie Bowl”  SEND ITS:  Tampa Bay Bucs support women in sports: https://www.instagram.com/p/DR-BirwDvCT/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==  The auntie who loved up on AJ Brown: https://www.instagram.com/p/DR0Q2khkbId/?img_index=1&igsh=MXJ6OTQzYW9jZG40Yw%3D%3D  Angel Reese x Paige Bueckers collab when??? Right now: https://www.si.com/wnba/sky/news/sky-star-angel-reese-paige-bueckers-unite-marketing-campaign Lando Norris becomes the F1 World Championship with McLaren: https://www.instagram.com/reel/DR-J9mYCUU-/?utm_source=ig_web_copy_link&igsh=NTc4MTIwNjQ2YQ==  Follow Blake on IG: @blaaakkkke Follow Caroline on IG: @cghendy Follow theSkimm on IG: @theskimm Learn more about your ad choices. Visit megaphone.fm/adchoices

Caroline breaks down the soap opera drama of Lane Kiffin’s recent divorce from Ole Miss for the younger, hotter LSU. Who knew a middle-aged white guy would occupy so much of our brain space? It’s also high-season for celeb-watch on the NBA sidelines, from Benny Blanco and Selena Gomez cuddling up to Conrad and Steven giving us an alternate ending for “The Summer I Turned Pretty” on the kiss cam. In this episode, we also cover:  The NWSL’s Sydney Leroux reveals how her silent health struggle is more prevalent in women’s sports than we believe Recapping DWTS season 13, plus Alix Earle shutting down rumors about her boyfriend, Braxton Berrios Why Ben Johnson went shirtless for the city of Chicago  How Post Malone’s Cowboys fandom goes beyond hometown loyalty  Petty Boys of the NFL week 13 edition, ft. Aaron Rodgers, Shelby Harris, and Cam Heyward SEND IT:  “The Summer I Turned Pretty” alternate ending at the Knicks game: https://www.instagram.com/reel/DRp7Uq8ASOA/  The Ottawa Charge proposal: https://www.instagram.com/reel/DRisb8ejTMp/?utm_source=ig_web_copy_link&utm_medium=email  Bald man finds solution for women athletes (yes, his baldness *is* relevant): https://www.espn.com/college-sports/story/_/id/47109557/2025-ncaa-volleyball-tournament-players-hair-band-tiy-brand-jerritt-elliott  Megan thee Stallion and Klay Thompson are the gift that keeps on giving: https://www.instagram.com/p/DRm2Y2dD0yf/  Follow Blake on IG: @blaaakkkke Follow Caroline on IG: @cghendy Learn more about your ad choices. Visit megaphone.fm/adchoices

Well Played headed to the West Coast for a LIVE podcast recording at the NWSL Championship weekend. Joined by special guests Sarah Spain, we recapped the NWSL awards, handed out a few of our own (hi, Midge Purce), and set the scene for the title match, including alll the drama the led to the big game. Plus, we mentioned our favorite storylines from a season that proved — yet again — that women’s soccer is operating on another level. theSkimm’s IG: @theskimm Blake’s IG: @blaaakkkke Caroline’s IG: @cghendy Sarah's IG: spain2323 Want more sports? Sign up for theSkimm’s sports newsletter at theskimm.com/sports. Learn more about your ad choices. Visit megaphone.fm/adchoices

Since at least late 2024, Russell Wilson has left thirsty comments on his wife Ciara’s Instagram posts asking for baby number five – aka, “Cinco.” Blake and Caroline join Ciara in her public plea to give her uterus a break. In other ick-worthy news, Sky Sports addressed the patronizing launch of their women-centric sports TikTok account, “Halo”. Matcha lattes and hot girl walks not included – thank God. In this episode, we also cover:  How LeBron and Bronny body swapped, “Freaky Friday” style The case for why Golden State Warriors player Draymond Green needs therapy  NFL week 12 highlights, including the Bills bouncing back, the return of spitgate, and the Chiefs dynasty…ending? The Knicks ultra fan who used his visit to the Vatican to give Pope Leo a custom jersey  Jordyn Woods’s heartfelt gift for Karl Anthony Towns’ 30th birthday  Why Adam Sandler and Timothée Chalamet were at a high school gym together SEND IT:  Jordyn Woods x KAT’s 30th birthday: https://www.instagram.com/p/DRGb3TiDQut/?img_index=1  Pope Leo gets his Knicks jersey: https://www.instagram.com/p/DRFILiOjIj8/?hl=en  Adam and Timmy ball out: https://www.instagram.com/p/DRLBtYvkS0S/?img_index=1  OTHER STUFF TO KNOW:  We will be at the NWSL Championships this weekend! Join us for a LIVE recording of Well Played at 2 PM on Saturday at the lot at creekside, 140 S. Montgomery Street in San Jose, California. ICYMI, our interview with Gotham FC’s Jaedyn Shaw: https://youtu.be/zriAtGJiXzA?si=sdr015p-ZC0YE--p&t=2066  Follow Blake on IG: @blaaakkkke Follow Caroline on IG: @cghendy Follow the pod on IG: @wellplayedpod    Learn more about your ad choices. Visit megaphone.fm/adchoices

Bengals fans, rejoice. The streets are saying Joe Burrow will return by Thanksgiving after healing his turf toe. Shocked he’s already making a comeback? Us too. Blake and Caroline suspect it’s all thanks to an Etsy witch – with a side of Joe’s crystal collection. Meanwhile, Dua Lipa spends a sporty day off.  In this episode, we also cover: Why Prince Harry issued an apology to Canadians post-World Series  Dak Prescott’s heartfelt speech surrounding the death of Cowboys defensive end, Marshawn Kneeland Which swatch of red lipstick Daniel Jones wore during the Colts game  Why Jaedyn Shaw shut down the “underdog” comments surrounding Gotham FC  Serena Williams and Ciara break it down – and which one of them couldn’t get back up SEND IT: Klay Thompson is the greenest flag: https://www.instagram.com/reel/DQw_i1qEsvK/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==  Jonas Brothers + Jason Kelce – aka girl dads – unite: https://www.instagram.com/reel/DQ4N2THCvud/?igsh=MTNuc3Q2MzZ5NWszMQ==  Origins of Dua LaPeep: https://www.youtube.com/watch?v=4jar6nzgmm4 Dua Lipa’s book club: https://tertulia.com/editorial-list/dua-lipa-complete-book-club-picks?srsltid=AfmBOoryU4Vl7KA_lYJvoyJ3_21MKtbkGI78xO-NB33wz-brVyLWOdo3 Ciara, Serena, and Venus: https://www.instagram.com/p/DQzWxmCiUEW/  Blake’s IG: @blaaakkkke Caroline’s IG: @cghendy theSkimm’s IG: @theskimm Want more sports? Sign up for theSkimm’s sports newsletter at theskimm.com/sports. Learn more about your ad choices. Visit megaphone.fm/adchoices

Bengals fans, rejoice. The streets are saying Joe Burrow will return by Thanksgiving after healing his turf toe. Shocked he’s already making a comeback? Us too. Blake and Caroline suspect it’s all thanks to an Etsy witch – with a side of Joe’s crystal collection. Meanwhile, Dua Lipa spends a sporty day off.  In this episode, we also cover: Why Prince Harry issued an apology to Canadians post-World Series  Dak Prescott’s heartfelt speech surrounding the death of Cowboys defensive end, Marshawn Kneeland Which swatch of red lipstick Daniel Jones wore during the Colts game  Why Jaedyn Shaw shut down the “underdog” comments surrounding Gotham FC  Serena Williams and Ciara break it down – and which one of them couldn’t get back up Learn more about your ad choices. Visit megaphone.fm/adchoices

David and Victoria Beckham graduated from “Mr. and Mrs.” to “Sir and Lady” after the soccer legend was knighted for his service in sport and charity. It was a decade-long process – and apparently included some expletive-filled emails when he got passed over years ago. The family gathered to celebrate, but we couldn’t help but notice one noticeably absent Beckham. Meanwhile, Simone Biles shared a “get unready with me” TikTok we didn’t know we needed full of cultural confessions. Simone, if you’re reading this: it would be our honor to show you how to use a dishwasher.  In this week’s episode, we also discuss:  Caroline’s crash out over the Jets trade of Sauce Gardner and Quinnen Williams Hellen Obiri breaking the NYC Marathon course record – and her parents adorable reaction Clayton Kershaw’s dad bod on full display, plus whether Shohei Ohtani is secretly fluent in English  What we want out of the next Cardi B and Robert Kraft sighting Joe Burrow’s Halloween costume that had us asking…why so serious?  Send Its:  Cardi B and Kraft are suite-side besties: https://www.instagram.com/reel/DQkokwUgEBU/?igsh=MThyaHZyY3F6bmNzbA==  Simone Biles’ “get unready with me” confessions: https://www.tiktok.com/@simonebilesowens/video/7566672113323560222?lang=en  Chappell Roan at the National Horse Show: https://www.instagram.com/p/DQf0kTcDv_t/  Miley Stewart isn’t Hannah Montana…Cam Dicker is: https://www.tiktok.com/@chargers/video/7567119748417195295?lang=en  Ms. Terry (aka Nick Saban’s wife)  is all of us: https://www.instagram.com/p/DQnRrDjDrxA/  Blake’s IG: @blaaakkkke Caroline’s IG: @cghendy theSkimm’s IG: @theskimm Want more sports? Sign up for theSkimm’s sports newsletter at theskimm.com/sports. Learn more about your ad choices. Visit megaphone.fm/adchoices

It was a big week in basketball news. Justin Bieber played in a rec league designed for “CEOs, VIPs, and people from all walks of life” (you may raise your eyebrows) while the NBA faces two scandals of its own. One deals with illegal sports betting and rigged poker games. The other? Jaylen Brown’s hairline. Also: Blake and Caroline surprise each other with sporty Halloween costumes for the pod, so watching on YouTube or Spotify is a must this week. In this week’s episode, we also discuss:  The moment we became Justin Fields stans A World Series game so crazy, Blake and Caroline are even intrigued  U.S. Soccer’s work to support pregnant and post-partum players on the USWNT  Why getting fired as a college football coach is almost as lucrative as being an active one  How to watch the NWSL Decision Day games this coming Sunday Send Its:  The Lions fan who welcomed a new member into the fandom: https://www.instagram.com/p/DQPezPlgcIC/?img_index=2&igsh=NHU0NWI4ajRuYW14 Panthers players got us feeling old: https://www.instagram.com/reel/DQKT1fSkRJC/?utm_source=ig_web_copy_link  The A’ja Wilson effect on Bam Adebayo’s game: https://www.instagram.com/p/DQO_avMga6L/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==  Travis Kelce hits the “The Fate of Ophelia” touchdown celly: https://www.tiktok.com/@courtneymarycrain/video/7566093931478273335  Blake’s IG: @blaaakkkke Caroline’s IG: @cghendy theSkimm’s IG: @theskimm Want more sports? Sign up for theSkimm’s sports newsletter at theskimm.com/sports. Learn more about your ad choices. Visit megaphone.fm/adchoices