73: Say Yes Anyway with Jason Middleton (From Eco Challenge Survival To Aviation Leadership, Jason Shares What Hard Seasons Teach About Growth)

Jason Middleton didn’t just reinvent himself once. He built an entire life around jumping into the unknown. Growing up as an overweight kid in Bakersfield with little confidence and no clear direction, he found salvation in endurance sports, eventually becoming a professional triathlete before pushing himself even further into the savage world of Eco Challenge adventure racing, battling jungles, oceans, sleep deprivation, and seven-day races that pushed human limits. When the sport began to outgrow him, he pivoted again, discovering aviation almost by accident and chasing a completely new dream as a pilot. Then 9/11 shattered his career plans overnight. What followed were years marked by devastating personal loss, financial collapse, divorce, and moments where he nearly lost himself entirely, yet every setback became fuel for another transformation. Today, as the founder and CEO of Silver Air Private Jets, Jason’s story is proof that second acts aren’t born from comfort or certainty. They’re forged by people willing to suffer, risk, evolve, and keep saying yes long after most would quit. Starring: Michael Newborn (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@michaelnewborn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) John Ballenger (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@john-ballenger53⁠) Guest: Jason Middleton https://www.linkedin.com/in/jason-middleton-03882978/ https://www.silverair.com/ Network/Produced by: Seltzer Kings (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@seltzerkings⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠seltzerkings.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Theme Music by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Saint Josh⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Listen Here: Spotify: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://open.spotify.com/show/71Uji4fPLsnGEJjeAqomiJ?si=77e3d7bb636c422a⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Apple: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://podcasts.apple.com/us/podcast/the-second-act-with-michael-and-john/id1707412739⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Amazon: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://music.amazon.com/podcasts/a6b369bb-36a9-47ab-9f22-1bacfcff6166/the-second-act-with-michael-and-john⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ iHeart: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.iheart.com/podcast/269-the-second-act-with-michae-123242148/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Socials: Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠secondactmovement.com⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@secondactmovement⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@secondactmovement⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@secondactmovement⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@secondactmovement⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AI-powered coach-client matching platform: ⁠⁠⁠trysam.ai⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices