Miss Understood with Rachel Uchitel
Sep 18, 2026 · 47 min · 20 segments
Before Jackson Olson stepped onto the Dancing with the Stars stage, he sat down with Rachel Uchitel to share the unlikely journey that brought him to the Savannah Bananas. In this special encore…
What made me leave that job is I was in the middle of a delivery one day, and I got a message from MLB.
They wanted me to create videos for them along with nine other creators, and I was like, "All right.
Like, I'm gonna take advantage of this." Um, made a video applying for it, 'cause I had to apply for it, um, and they picked me.
And then, yeah, we had to make 12 videos for the Creator Class, what- whatever you want them to be.
If you're at a stadium eating a hot dog, it was just promoting MLB in any way.
I almost see it as, like, a competition, like I wanna be the best one out of all nine of us-
... get the most views, the most engagement, all of this stuff, so that if there's another opportunity next year, 'cause this is not gonna go on forever, they'll pick me.
If they're gonna- if they're deciding between one person, they're gonna pick me, and that ended up happening.
Yeah, this is my next step, but I still knew that it was, like, once the 30 stadium was over, then what? Like-
What made me leave that job is I was in the middle of a delivery one day, and I got a message from MLB.
They wanted me to create videos for them along with nine other creators, and I was like, "All right.
Like, I'm gonna take advantage of this." Um, made a video applying for it, 'cause I had to apply for it, um, and they picked me.
And then, yeah, we had to make 12 videos for the Creator Class, what- whatever you want them to be.
If you're at a stadium eating a hot dog, it was just promoting MLB in any way.
I almost see it as, like, a competition, like I wanna be the best one out of all nine of us-
... get the most views, the most engagement, all of this stuff, so that if there's another opportunity next year, 'cause this is not gonna go on forever, they'll pick me.
If they're gonna- if they're deciding between one person, they're gonna pick me, and that ended up happening.
Yeah, this is my next step, but I still knew that it was, like, once the 30 stadium was over, then what? Like-
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