When Things Don’t Go To Plan (Why I Keep The Faith)

There are a lot of things we like to think we have control over, but how much of that is our wants just aligning with chance?

Nov 10 • Jake Freudinger

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October 2026

Why It’s Important to Bet on Yourself

Living up to everyone else’s expectations can leave very little room for your own. So why do we keep asking for permission to build a life we actually…

Oct 19 • Jake Freudinger

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Wedding Planning, Vows & DJ Mishaps | Hayley & David • Win The Night Ep. 85

David built his vows from song titles and lyrics he’d saved for years. Hayley’s dad secretly requested a song. David had a promise ready: “I’ll take…

Oct 19 • Jake Freudinger

58:23

Burnout Almost Broke Us: Grief, ADHD & Friendship with Jake Freudinger • Win The Night Ep. 84

Burnout, depression, ADHD, autism and grief. No guest this time: this is the Win The Night check-in, the real conversation Josh and I (@froydinger…

Oct 19 • Jake Freudinger and Joshua Lopez

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57:23

September 2026

The Kid Who Held Everyone Together with Stephanie Bird • Win The Night EP. 83

Stephanie was the kid everything was "okay” for, who could truck through anything. The mediator, the comforter, the one her parents looked to to get a…

Sep 3 • Joshua Lopez and Jake Freudinger

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1:15:36

August 2026

Bombing, Day Jobs, And Doing It Anyway with Erik (Big Goose) • Win The Night EP. 82

We get into bombing two open mics in one night, making “technically bombs” for the government, growing up in a Florida trailer with an inventive coping…

Aug 20 • Jake Freudinger

1:14:00

Therapy Is NOT Forever with Curley Lawson • Win The Night Ep. 81

In this in-person conversation, Air Force veteran and trauma therapist Curley Lawson talks with us about emotional triggers, childhood neglect…

Aug 20 • Jake Freudinger

1:05:57

How Music Carried Me Through with Billy Mays III • Win The Night Ep. 80

Billy Mays III joins Josh to talk about how music played an important roll in his healing, and how he has told the live story of his emotions through…

Aug 5 • Jake Freudinger and Billy Mays III

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45:10

July 2026

I Was Betrayed. What’s Next?

The pieces were finally talking to each other, and the idea that had been living in my head was suddenly doing stuff on a screen. Then the arrangement…

Jul 30 • Jake Freudinger

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June 2026

We forgot how to be bored.

My daughter picked up some dirt, and taught me the most valuable life lesson I have had in a while.

Jun 28 • Jake Freudinger

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Learning to Move with the Storm

Sometimes it can be hard to face the cold hard reality that you have to ride this one out. Here are some things that help make the storm a bit easier to…

Jun 22 • Jake Freudinger

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Reframing ADHD for Creativity: From Nurse to Drone Pilot • Win The Night Ep. 78

Learn how he turned ADHD into a strength for cinematic storytelling and why he believes the "learn, fly, crash, and build" mindset applies just as much…

Jun 9 • Joshua Lopez and Jake Freudinger

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49:45