Flip Your Friday

Follow Flip Your Friday
Share on
Copy link to clipboard

Flip Your Friday (FYF) is an unapologetic, in-your-face podcast about going the extra mile when others tend to shy away from delivering what matters: winning. Co-Hosted by sports agent Wynn Silberman and dynamic CEO, entrepreneur, and investor Casey LeBlanc, guests will share their fascinating stories about what it’s taken them to win. Whether it’s professional athletes, serial entrepreneurs, Wall Street Stockbrokers, or reformed criminals, the theme is that consistent paradigms exist to formulate a win: hard work, perseverance, and belief without evidence. FYF delivers a functional blend of real-life storytelling with hard-nosed facts about how to succeed in life. The conversations are raw and revealing; a much-needed anecdote for those waning in a sea of uncertainty but thirsty for culture, identity, and a will to win. New episodes every other Friday.

Casey LeBlanc and Wynn Silberman


    • Jan 5, 2024 LATEST EPISODE
    • infrequent NEW EPISODES
    • 55m AVG DURATION
    • 31 EPISODES

    Ivy Insights

    The Flip Your Friday podcast is an exciting new addition to the world of sports podcasts. With its first episode, it has already managed to captivate listeners with its insightful and entertaining content. The hosts offer a unique perspective on life behind the curtains of being an NFL player and delve into the intricate business aspects of professional football. It's a refreshing take that keeps the audience engaged and wanting more.

    One of the best aspects of this podcast is the fascinating insights shared by the hosts. They provide valuable behind-the-scenes information that gives listeners a glimpse into the reality of being an NFL player. It's rare to find such intimate knowledge shared so openly, and it adds depth to the listening experience. Additionally, their storytelling skills are commendable, as they seamlessly move the narrative forward, holding interest throughout.

    Another standout aspect of The Flip Your Friday podcast is the chemistry between the hosts. Casey brings a great sense of humor that adds levity to the discussions, while his counterpart does an excellent job at keeping things on track. Their dynamic reminds me of legendary commentator duo John Madden and Pat Summerall, which only enhances the enjoyment factor for listeners.

    While it's hard to find any major flaws in this podcast, one minor aspect that could be improved upon is occasionally providing more context or background information for those less familiar with football terminology or players. This would make the podcast more accessible to a wider audience who may not have extensive knowledge about professional football.

    In conclusion, The Flip Your Friday podcast has made a strong debut with its first episode and promises to deliver even more value-packed and enjoyable content in future episodes. The hosts' insider perspective on life as an NFL player combined with their storytelling abilities make for an engaging and educational listening experience. Whether you're a football fan or simply interested in gaining unique insights into professional sports, this podcast is definitely worth tuning in to.



    Search for episodes from Flip Your Friday with a specific topic:

    Latest episodes from Flip Your Friday

    University of Michigan MVP and NFL star Chase Winovich talks Business and Tech

    Play Episode Listen Later Jan 5, 2024 79:36


    Flip Your Friday is back! In this episode Wynn Silberman & Casey LeBlanc are joined by special guest Chase Winovich as they dive deep into the fascinating world of NFL, Business, and Technology. Chase shares valuable insights and experiences that bridge the gap between sports, entrepreneurship, and innovation.

    Hoops Business and Leadership

    Play Episode Listen Later Feb 10, 2023 68:20


    Flip Your Friday hosts head coach Frank Robinson, a former professional basketball for NBA teams including the Atlanta Hawks and LA Lakers; whose coaching style was first noticed by artist Kanye West and his Donda Basketball Academy located in Los Angeles, CA. After completion of one successful, Frank choose to exit Donda and form a basketball refinery with fellow teammate Horace Wormely called The DSTRKT to disrupt what they see as a failing culture of not only youth basketball but youth sports as a whole. In this interview Casey and Wynn take a deep dive into the dichotomy between highschool basketball and basketball academies, discuss why children should play multiple sports in order to develop into elite athletes and how the game of basketball prepares the youth as successful business leaders and good humans.

    The DSTRKT- the Game of Basketball as Life

    Play Episode Listen Later Jan 27, 2023 48:31


    In this episode Casey and Wynn interview co-founder of The DSTRKT Horace Wormely, a basketball centric foundation based in Chatsworth, California whose professional basketball career alone extended over six continents for twelve seasons. While only 5' 7” tall, Horace shares how his height in the game was seen as nothing more than advantageous through out his career as a pro. In addition he reflects on how the game of basketball prepares him as a global thinker and a seasoned entrepreneur and how the game of basketball prepared him to compete at an elite level in business and the game of life.

    FYF Season 3: Episode 1 "Bowl Season": San Jose State versus Eastern Michigan University

    Play Episode Listen Later Jan 13, 2023 13:31


    Casey and Wynn launch Season three with an offsite venture to Boise, Idaho to interview star San Jose State football quarterback Chevan Cordeiro and Nfl prospect wide receiver Elijah Cooks just days before their final game of the season against Las Vegas Raider superstar Maxx Crosby and Hard Knocks star Brogan Robacks' Alma Mater Eastern Michigan University in the Potato Bowl. In the interview Casey and Wynn dive into the world of NILS and the transfer portal from the NCAA athletes' perspective. In addition, they speak candidly with their guests on what it's like to chase a childhood dream of making an NFL roster.

    FYF Season 3: Episode 1 "Bowl Season": San Jose State vs Eastern Michigan University

    Play Episode Listen Later Jan 13, 2023 14:33


    Casey and Wynn launch Season three with an offsite venture to Boise, Idaho to interview star San Jose State football quarterback Chevan Cordeiro and Nfl prospect wide receiver Elijah Cooks just days before their final game of the season against Las Vegas Raider superstar Maxx Crosby and Hard Knocks star Brogan Robacks' Alma Mater Eastern Michigan University in the Potato Bowl. In the interview Casey and Wynn dive into the world of NILS and the transfer portal from the NCAA athletes' perspective. In addition, they speak candidly with their guests on what it's like to chase a childhood dream of making an NFL roster.

    The Flip Your Friday 2022 Leadership and Business Recap final episode.

    Play Episode Listen Later Dec 30, 2022 34:24


    Tune in to Casey and Wynn's season-ending episode of Flip Your Friday. This recap shares a vivid glimpse into each and every special guest interview. They help guide the listener to key takeaways that can teach one how to lead and succeed in a world where change is the only constant:From George Whitfield's intimate knowledge and perspective on the football life of Johnny Manziel to J Valentine and the creative process on how hit songs manifest to Brandi Chastain and her thoughts on leadership, USA Women's Soccer and the World Cup to San Jose States head coach Brent Brennan's perspective on NIL deals, the NCAA and the transfer portal this episode provides a perfect road map on what to look for and how to convert each guest interview into a learning experience that applies to life and business.

    NFL Quarterback Specialist George Whitfield JR.

    Play Episode Listen Later Sep 16, 2022 78:37


    In this episode, Casey and Wynn explore the world of raising an NFL Quarterback from childhood to being selected in the NFL Draft. More specifically, their guest George Whitfield walks them into the journey of his client and friend Heisman Quarterback Johnny Manziel to illustrate the challenges these men go through in their search for identity, leadership skills, and success.

    Brandi Chastain USA Soccer and Leadership

    Play Episode Listen Later Sep 2, 2022 37:07


    n this week's episode Casey and Wynn interview iconic Olympic Gold Medalist and and World Cup Champion Brandi Chastain a litany of topics that include the role of women and leadership as it applies to the playing field, business and life. In particular, Brandi's reflection on whether leaders are born and can be molded is nothing short brilliant and well worth the listen.

    4 X Pro Bowl Quarterback and San Francisco 49er Jeff Garcia

    Play Episode Listen Later Aug 5, 2022 64:51


    In this episode, Casey and Wynn interview 4 X NFL Pro Bowl San Francisco 49er quarterback Jeff Garcia. Jeff shares an in depth and tantalizing reflection not only on the highs and lows of his NFL career but also poignant moments of his personal life that include the tragic loss of not one but two siblings at a young age and how playing ball at an young age helped heal not only himself but his entire family from their tragic loss.

    Marlon Webb, Social Influencer opens up

    Play Episode Listen Later Jul 15, 2022 57:15


    In this episode Marlon Webb leads a fascinating fyf discussion that includes important milestones in his personal life's journey, the impact social media plays in mental health, perspective on the role of humor in today's censor-centric world and the evolution of his own identity from autistic child therapist to cinematic artist and director.

    The Sleep Whisperer!

    Play Episode Listen Later Jun 17, 2022 95:19


    Join Casey and Wynn's journey into the realm of sleep, health and business with JD “the Sleep Whisperer”. In this episode JD shares how to shape the importance of sleep into an explosive and lucrative business of slinging sleep mattresses. A larger than life character JD delivers a cacophony of important life lessons and gems that include how to handle adversity and flip any perceived struggle into a rewarding and meaningful victory.

    Music mogul J. Valentine reflects, responds, and reacts to all things music and the impact in his life

    Play Episode Listen Later May 27, 2022 66:38


    Casey and Wynn sit down with bay area legendary singer, song writer, producer and business manager Johnnie Newt, “J Valentine” to reflect on topics ranging from: the role imagination plays in song writing to the nuts and bolts of a record label and how to succeed in all aspects of the music business.

    San Jose State Head Football Coach Brent Brennan Discusses Winning in Football & Life

    Play Episode Listen Later May 13, 2022 47:49


    FYF Season 2 launches today: This first episode of the season features Wynn Silberman and Casey LeBlanc's engaging discussion with San Jose State Head Football Coach Brent Brennan on topics that include: leadership, the NCAA's dilemma with transfer portals and NILS for collegiate athletes and the key to a multifaceted success in life.

    16. "I tend to always be looking forward." | Hanson Hsu

    Play Episode Listen Later Dec 17, 2021 59:28


    Hanson Hsu is the founder and CEO of Delta H Design Inc., which is revolutionary acoustics and architecture firm that focuses on beauty, performance, and innovation. Hanson chats with Casey and Wynn about some of the award-winning music artists that he has worked with, touches on quantum acoustics, and his innovative line of what he calls "ZR Acoustics" products. To quote Hanson himself, he declares that "Everything we design must look beautiful and sound beautiful." and we're giving you the inside scoop on what that means and how it's done! Be sure an LIKE and FOLLOW!

    15. "I've had the opportunity to represent four of the greatest athletes of all time, in their sport" | Rich Nichols

    Play Episode Listen Later Dec 3, 2021 55:40


    Super sports attorney Rich Nichols has represented some of the most elite athletes of all time, in their respective sports. With more than thirty years of experience in the business of sports, law, politics, finance, venture capital, and technology, Rich has had some incredible experiences and has been given some truly incredible insights into the minds, emotions, and psyches of professional athletes. As a two-time NCAA Division 1 All-American and a competing member of the US Track and Field team, Rich gives us insight into his own experience and parallels between sports, law, high achievement, and life's challenges. Enjoy, and don't forget to SUBSCRIBE and FOLLOW!

    14. "You want to know what's really happening in Thailand?" | Louis Ziskin 2.0

    Play Episode Listen Later Nov 12, 2021 65:12


    You may remember our second episode ever, where we hosted LA entrepreneur, Louis Ziskin. After we had Louis on the show, he was arrested in Bangkok, Thailand, and accused of being involved in a kidnapping plot. Since May, there have been all kinds of updates and developments in this tangled web, and we've got Louis back on the show to tell you in his own words what REALLY happened in Thailand. Get ready, this one is a real ride! Remember to like and subscribe!

    13. "If no one's going to give you the opportunity, then give the opportunity to yourself" | Noel G

    Play Episode Listen Later Sep 24, 2021 46:52


    Noel G is a professional Hollywood actor, acting coach, producer, and business owner with decades of experience and commercial success. He has had roles in numerous movies from The Dark Knight Rises to Training Day to Bruce Almighty, and he has perfected his craft over the years. Noel dives deep into how he got started acting, being at the right place at the right time, and what kind of mentality and strategy to use in order to stay relevant and successful as time passes as an actor. In true FYF fashion, Wynn and Casey chat with Noel G about how his mentality and mindset have given him the upper hand and allowed him to stay on top of his game. You'll LOVE this episode! Happy FYF! Remember to LIKE and SUBSCRIBE!

    12. "Fighting for those who can't fight for themselves really resonated with me" | Nate Boyer

    Play Episode Listen Later Sep 10, 2021 64:29


    Nate Boyer is a former college and pro athlete (Seattle Seahawks), former active-duty Green Beret, mentor, actor, and producer. Nate discusses the incredible journeys and adventures that he has had in his life with Wynn and Casey, going in-depth about the mindset it took to achieve what he has and how his viewpoint on problems and challenges has allowed him to operate differently than most other people. From Boyer's time working on a fishing boat in San Diego to his deployment in Afghanistan, This episode is full of impactful insight! You'll love the journey! We know we did... Be sure to LIKE and SUBSCRIBE!

    11. “I think the mental side of it is 99%." | Mike Rathje

    Play Episode Listen Later Aug 27, 2021 48:33


    Mike Rathje is a Canadian former pro NHL player who conquered 13 seasons and played for both the San Jose Sharks and the Philadelphia Flyers. Mike takes us on a journey through his beginnings and what it took to get into the NHL and also how coaching styles and emotional intelligence have changed and shifted in the game today compared to how it was when he first started. He believes that 99% of the game is mental, and the new mentorship program that he is testing out could be a total games changer for the future. Remember to like and subscribe!

    10. “You have to be willing to do what other people aren't willing to do." | Joe Sai

    Play Episode Listen Later Aug 6, 2021 51:18


    Joe Sai is a businessman, entrepreneur, and the Chief of Staff at Harvest Health & Recreation, which is a vertically integrated cannabis company and MSO. Joe tells us about life lessons that have served him well throughout his successful career, how the cannabis biz works, and his unique perspective on having money and success and what that means. There's a wealth of great insight and high-level perspective in this episode!  Don't forget to subscribe!

    chief recreation mso harvest health
    09. “When I walked into that ring, the game plan just clicked." | Mikaela Mayer

    Play Episode Listen Later Jul 23, 2021 64:46


    Mikaela Mayer is an American professional boxer and Olympian who has held the WBO super featherweight title since 2020. Mayer talks with Wynn and Casey about her journey from the beginning to how she got to where she is today.  She reflects on the Olympics, training, and the mindset and discipline she had to harness to achieve her world champion status. Learn more about Mikaela by following the link below!

    08. “Our primary purpose was to flip the TGIF culture on its head." | Casey LeBlanc & Wynn Silberman

    Play Episode Listen Later Jul 9, 2021 48:51


    Wynn and Casey reflect on highlights, guests, and some of the amazing life experiences that FYF guests have shared on the show so far.  The guys also discuss the guest experience, share what happens behind the scenes, and talk about their future vision for the podcast.  Get the key takeaways and highlights from episodes featuring Kyle Williams, Louis Ziskin, Bud Dupree, Marquette King, Guy McIntyre, Rashied Davis, Ben Pechetti, and more! Remember to follow, rate, review and subscribe wherever you get your podcasts, and check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    07. “In my world, the brand is bigger than the farm.” | Ben Pechetti

    Play Episode Listen Later Jun 18, 2021 57:26


    Founder of Sticker Farmer, a full-scale cannabis branding and design firm, Ben Pechetti, joins Wynn and Casey for a conversation about the growing industry, being a life-long entrepreneur, and the hustle it took to build his agency.  The trio will dive into what obstacles and mental challenges it takes to grow a business, how you can't be afraid to leave your comfort zone, and how you define success when you're constantly pushing the bar. Remember to follow, rate, review and subscribe wherever you get your podcasts, and check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    06. “What helped me to survive is not necessarily what is going to help me thrive.” | Rashied Davis

    Play Episode Listen Later Jun 4, 2021 67:44


    Former teammate of Casey's and former client of Wynn's, Rashied Davis joins the duo for a raw conversation about mental toughness, teachable moments, maintaining confidence through adversity, and the thin line between compartmentalization and shutting down. On this episode of FYF, Davis speaks to the role that sports played as an outlet and how he has grown through the traumatic events of his life. They also reminisce about college football and the bonds that teammates share. Davis' foundation, Saturday Place, is his full-circle moment. Built from a deep understanding of how his community helped shape his life, Davis hopes to open young children's eyes to the potential of possibility beyond their carpet square. For more information on Saturday Place visit: https://www.saturdayplace.org/about/ If you have enjoyed FYF so far, please remember to rate, review, and subscribe to be notified when new episodes are available. Check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    05. “Once I cross that chalk line, it's on.” | Guy McIntyre

    Play Episode Listen Later May 21, 2021 54:52


    Guy McIntyre had a 13-year NFL career, he played in three Super Bowls and five Pro Bowls, and this week he joins Wynn and Casey for a dive into leadership styles and living your life with self-awareness. The trio discusses turning “it” on while on the field, building loyalty, and recognizing individual human nature. Of course, they also talk about Casey's hero, Joe Montana, and how the NFL had fun during McIntyre's tenure. If you have enjoyed FYF so far, please remember to rate, review, and subscribe to be notified when new episodes are available. Check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    04. “If you don't adjust, you're going to stay behind.” | Marquette King

    Play Episode Listen Later May 7, 2021 61:56


    NFL free agent, Marquette King, joins Wynn and Casey for a very candid conversation about being one of the top punters in the league, overcoming adversity, his expectations for himself, and how music has allowed him to express himself beyond the field. Check out his music here: https://open.spotify.com/artist/7sBwSfsV3RhTKdg4HNRW5p?si=iTrD6OaIQLy4yreRMJciaQ If you have enjoyed FYF so far, please remember to rate, review, and subscribe to be notified when new episodes are available. Check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    BONUS | "You have to choose what it takes to get what you want." | Casey LeBlanc and Wynn Silberman

    Play Episode Listen Later Apr 23, 2021 36:45


    On this bonus episode of FYF, our hosts interview each other (and a bottle of whiskey). Casey and Wynn dive into the motivation behind starting this podcast, their personal philosophies, and how they lost their virginity. The friends share stories they've never told each other and answer the ultimate question: what do you want your legacy to be? If you have enjoyed FYF so far, please remember to rate, review, and subscribe to be notified when new episodes are available. Check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    03. “Money can't hide the real you.” | Bud Dupree

    Play Episode Listen Later Apr 9, 2021 65:11


    NFL player Bud Dupree joins Wynn and Casey this week to talk about how he determines success and what makes a team successful, how football was his safe haven, and what he's learned about leadership through his journey. Dupree, an outside linebacker drafted in the first round by the Pittsburgh Steelers in 2015, recently signed with the Tennessee Titans. If you have enjoyed FYF so far, please remember to rate, review, and subscribe to be notified when new episodes are available. Check out our YouTube channel: https://www.youtube.com/channel/UCoUILDhjt6ejea70Ez9fJaA

    02. “Getting arrested was probably the best day of my life.” | Louis Ziskin

    Play Episode Listen Later Mar 26, 2021 86:29


    From living behind bars for 12 years to being one of Entrepreneur's 2016 Top 8 Tech Pioneers to Watch, Louis Ziskin has always had a mind for business. In this episode, Wynn and Casey speak to Ziskin about each of his ventures (illegal and legal), representing himself in court, developing self-awareness, and how he approaches adversity in everyday life.

    01. “I would have played with a gunshot wound.” | Kyle Williams

    Play Episode Listen Later Mar 12, 2021 74:58


    Former NFL player, Kyle Williams, joins Wynn and Casey to discuss how he finds that extra 20% needed for success. In this conversation, Williams gets candid about that fateful game against the Giants, the ups and downs of his career, different leadership styles he's encountered, and what it takes to be an elite athlete.

    Our Origin Story

    Play Episode Listen Later Mar 3, 2021 2:53


    We know our name is unconventional, but it comes from an experience that has defined co-host Casey LeBlanc's life. F*ck You Friday (FYF) is an unapologetic, in-your-face podcast about going the extra mile when others tend to shy away from delivering what matters: winning.

    Claim Flip Your Friday

    In order to claim this podcast we'll send an email to with a verification link. Simply click the link and you will be able to edit tags, request a refresh, and other features to take control of your podcast page!

    Claim Cancel