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Trading Secrets

240. Jackson Olson: From delivering for Instacart to 6 figure deals with Gatorade?! Savannah Bananas star reveals the full-circle moments in his career within content creation & baseball, being fan-focused, and the business behind it all!

Trading Secrets

Audioboom Studios

News, Business News, Business, Entrepreneurship, Education, Self-improvement

55.5K Ratings

🗓️ 23 June 2025

⏱️ 68 minutes

🧾️ Download transcript

Summary

This week, Jason is joined by  social media personality, content creator, and star of the Savannah Bananas baseball team, Jackson Olson!
Jackson, a former collegiate baseball player who had inspirations to go pro after school, gained recognition from his baseball related TikTok content. After raking in over 2.5 million followers, he caught the eye of the MLB and Savannah Bananas, eventually giving him roles in social media and on the team and becoming the star attraction. The Savannah Bananas are the semi-pro baseball team focused around the fan experience with their brand of banana ball similar to the decades long format of the Harlem Globetrotters. 
Jackson shares why he turned down being drafted by the Diamondbacks and how the pandemic reshaped the MLB draft. He opens up about the financial realities of minor league life compared to the majors, the decision to work for Instacart and document it online, and the full-circle moments that followed in his social media journey. From joining the first wave of MLB content creators in 2021 to carving out a role with the Savannah Bananas, Jackson dives into the business side of baseball entertainment, how he handles negotiations, and what it means to break the barrier between fan and player. He also touches on landing his Reebok deal, why he follows his energy over just his dreams, what keeps him mindful of his online presence, his current relationship status, spending habits, and more.
Jackson reveals all this and so much more in another episode you can’t afford to miss!
Host: Jason Tartick
Co-Host: David Arduin
Audio: John Gurney
Guest: Jackson Olson

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Transcript

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0:00.0

Welcome back to another episode of Trading Secrets. I'm your host, Jason Tarduk. We haven't done an intro in a second, but what a better time to do it than right here, right now,

0:22.2

while David Ardwin is sitting to my right. We are in Nashville, Tennessee. We just had a

0:25.6

boy's weekend. It was one hell of a time. David, just give people a little tease for what they

0:31.5

can expect this episode and in the recap. Yeah, this episode, great. Great learning about a new

0:35.8

industry. Great getting inspired by, you know, an up-and-coming social media star and athlete

0:40.6

who has a really unique story of, you know, how he got there from instacarting groceries

0:45.9

to playing in baseball, not in the MLB in front of 100,000 people.

0:51.4

Really, really amazing episode. And yeah, a little teaser, an amazing weekend

0:57.1

with the boys. Amazing week with the boys. We do have a giveaway. So make sure you stay tuned for the

1:01.4

winner that we announce in the recap. If you can give us five stars right now, we have things to give

1:05.7

away. Just make sure you put your Instagram handle and or your username so we can announce it in

1:10.7

the recaps.

1:11.6

The one thing I'll tell you about this episode is whether you're into sports or not,

1:15.6

there's something happening at a larger level with entertainment and the crowds that are

1:22.0

navigating and being, I would just say drawn to different forms of things that are

1:27.3

occurring within these

1:28.4

forms of entertainment. And you see that with Savannah bananas. And it's changing the game in ways

1:33.6

that we can't ignore no matter what you do for work, where you live, or what your interests are.

1:39.4

So stay tuned to this episode, and especially the recap. One quick little thing I want to tell you

1:43.7

about an article I read

1:44.4

this morning, the number of homes for sale is finally rising. Buyers aren't interested after years

1:52.7

of frustration with fast rising prices and bidding wars. Buyers now have the upper hand in many

...

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