REVISITED: Jackson Olson — From Instacart to the Savannah Bananas

Miss Understood with Rachel Uchitel

Jackson Olson shares his unexpected journey from college baseball star to Instacart delivery driver and TikTok sensation, culminating in a c

Key takeaways

• Jackson's baseball career nearly ended due to the pandemic-induced缩减 of the MLB draft.
• His TikTok content from Instacart deliveries attracted attention, leading to a brand deal and eventually an opportunity with the Savannah Bananas.

Main topics

• From college baseball to Instacart delivery
• Rise through TikTok and social media

Notable quotes

"I was playing in the Cape Cod League... then COVID happened, and MLB draft, instead of picking 1,500 players, they picked 150. End of my baseball career."

Conclusion

Jackson Olson's story is a testament to resilience and reinvention—pro

Transcript preview

Speaker 1 (0:00) Before we get started, I wanted to let you in on a little secret. What you're about to hear is only part of the conversation. Every Speaker 2 (0:06) week, we keep talking Speaker 1 (0:07) over on Patreon, where you'll find exclusive bonus episodes, behind-the-scenes footage, after-show conversations with my guests, and personal stories from my life that I don't share anywhere else. If you love Misunderstood, Patreon is where you'll get the full experience. Just head on over to patreon.com slash misunderstood with Rachel. You could tell. or click the link in the show notes. I'd love to have you join us. This is the story of how I became the third baseman for the most fun team in sports. Speaker 2 (0:38) I was playing in the Cape Cod League, which is the most prestigious college baseball league. The Diamondbacks offered me a contract to forego my next year of college. not drafted, but basically signed. Talked to my coach, talked to my dad, and they were like, go back for your senior year, get drafted. And then COVID happened, and MLB draft, instead of picking 1,500 players in the draft, they picked 150. End of my baseball career, I'm completely done. So I started delivering groceries. No Speaker 1 (1:00) way, you were doing TikTok videos of your deliveries? Speaker 2 (1:03) Instacart reached out to me. They were like, hey, we want to pay you to do this Super Bowl ad. What made me leave that job is I was in the middle of a delivery one day, and I got a message from MLB. It was a direct message. Jackson, we want you to go. to every MLB stadium and rank every MLB stadium. So I was at my 21st stadium on the field recording videos. I had this itch. I'm like, this is fun, but I miss baseball so much. I miss playing so much. Speaker 1 (1:27) Later that night, I was in my hotel and I saw not one, not Speaker 2 (1:30) two, but three banana TikToks. How Speaker 1 (1:32) did you get a hold of them? Speaker 2 (1:33) Yeah, so I made a TikTok. So Speaker 1 (1:34) Jesse Cole reached out directly? Speaker 2 (1:36) Yep, he DMed me and was like, Jackson would love to work with you in any way. Can Speaker 1 (1:40) you explain what banana ball is? Speaker 2 (1:42) It's theater on a baseball field, but we're also playing a real game. We're doing crazy walk-ups. We're singing songs. We're doing dances. We're throwing the ball between our legs. This is a two-hour time limit. If the game's tied at the end of the game, we have a showdown where it's like pitcher versus hitter. It's like very WWE style. Fan catches a foul ball. It's Speaker 1 (1:57) an Speaker 2 (1:57) out. Have Speaker 1 (1:58) you ever been playing and something goes terribly wrong? Speaker 2 (2:00) Oh my gosh, yes. Speaker 1 (2:07) Welcome back to Misunderstood. I'm Rachel. You could tell my guest today is Jackson Olson, the third baseman for the Savannah Bananas, a name you've probably heard a lot lately. But unless you've been to a game, you might not fully understand what makes this team so special. Jackson has had an incredible journey in baseball, playing at collegiate level before joining the Bananas, a team that has taken the sports world by storm with their unique blend of high energy entertainment, unconventional rules and nonstop fan engagement. The Bananas are more than just a baseball team. They're a phenomenon. selling out stadiums across the country and redefining what it means to experience America's pastime. I had the pleasure of sitting down with Jackson and hearing all about how he got his start into TikTok and how he combined his love for being creative with playing baseball. So what's it really like to be part of the most talked about team in baseball? Jackson is here to give us an insider's look at life as a banana from the behind the scenes antics to the pressure of playing a game that's as much about showmanship as it is about skill. Whether you're you're a baseball fan or just love a great story, you're going to love this conversation with Jackson Olson. Let's get into it. Jackson, I'm so excited that you're here with me. I've heard nothing but Savannah Bananas for the last couple months. And it's like such an honor to have you here and ask you all the questions everyone wants to know. So thank you for joining me on Misunderstood. Speaker 2 (3:28) Yeah, thank you for having me. I also love the name Misunderstood. It's really cool. Speaker 1 (3:32) Thank you. I really appreciate that. So I want to start with who you are as a person, because so many people are focused on the team as a whole, but as an individual, I want to know you. So can you tell me a little bit about your upbringing and when your love for baseball started? Speaker 2 (3:46) Yeah, I mean, my love for baseball started immediately. My brother and dad both played. I was a bat boy for my brother's team growing up. So automatically, you're just thrown into the baseball world. Bunch of 18, 17, 18 year old, 19 year olds swearing and just like probably not the best like scenario for me to be in when I was five years old. But it made me love the game. And that's kind of all part of the game. And yeah, so that's when it started. Speaker 2 (4:12) Obviously, I loved baseball my entire life, so I continued it through high school, continued it through college. Luckily, I was able to get a scholarship to the University of Hartford, played shortstop three years there, and then COVID hit. This is all the spark notes of this story, but COVID hit, and I was like, you know what? I've always wanted to play baseball down south. I was playing. I was shoveling snow on our field at Hartford every December, and I'm like, dang, I want to go to the south. I want to see what it's all about. So I transferred to Stetson, played a year there. But before that, I was playing in the Cape Cod League, which is the most prestigious college baseball league and was playing really well. And the Diamondbacks, Arizona Diamondbacks came up to me one day and they were talking to me for a little while. And they were like, hey, like we think that you could be a good fit for our organization, blah, blah, blah. And then they offered me a contract to basically forego my next year of college, like not go to my next year of college. Speaker 2 (5:09) get not drafted but basically signed and i was like whoa like okay obviously i'm gonna say yes to that i want to play professional baseball it's been my goal it's every kid's dream to put on a major league baseball hat um and talk to my coach talk to my dad and they were like go back it was a really small offer it was like five thousand dollars which seemed to like a lot to me at the time right really in the grand scheme of things was not at all which i'd find out later um my dad my coach at hartford was like go back for your senior year get drafted These teams will have more invested in you. If you have a really good senior year and you play really well, these teams will want you even more and they'll give you more money and they'll have basically more invested in you. So I was like, all right, cool. And then COVID happened and MLB draft, instead of picking 1500 players in the draft, they picked 150. Speaker 1 (5:55) So it Speaker 2 (5:56) really went down like a significant amount. And I was unfortunately not in the top 150 best players. I was probably lucky. 500 to a thousand. I don't know what I would have been. But the draft got cut short because of the less teams, less money teams had because of COVID. And then I was like, all right, I'm done. Like this is, this is my end of my baseball career. I am completely done. So I started delivering groceries because I didn't want to get a job yet because I was too immature to get a job in the real world. So I was like, let me just deliver groceries and like document my time because I had started a TikTok channel before that. And I was like, let me just like make videos of delivery. No one's doing this in the entire world. Wait, Speaker 1 (6:38) no way. You were doing TikTok videos of your deliveries? Speaker 2 (6:42) Yes. I have like literally, if you go back to Nolson Instacart, you will literally find probably a hundred or hundreds of videos of me delivering groceries. The funny part about that is that Instacart reached out to me and I didn't even know this was a real thing. This is like my first brand deal. They're like, hey, we want to like pay you to do this Super Bowl ad where you're in full. football gear, running through the store, like grabbing Doritos, grabbing Mountain Dew, putting it in your cart. And they paid me more for that than I made my entire time delivering groceries, actually. So I was like, all right, full circle moment of my entire life. So yeah. That Speaker 1 (7:15) is so cool. Oh my God. So, all right, hold on. I have so many questions. So as a young kid, first of all, so you were good enough, obviously, but so you really wanted to be a baseball player. Speaker 2 (7:27) That was it. That's all I wanted. Speaker 1 (7:28) And was there a plan B? Like, were you going to be an accountant? I mean, what else was there for you if there wasn't? Plan Speaker 2 (7:35) B was to be a professional Instacart driver. That was really what. So Speaker 1 (7:39) that's as far as it went. Speaker 2 (7:41) I literally had nothing else. I mean, I remember my mom texted me this like a month ago. And it was a memory popped up on her phone that we both went to New York City because I was from Connecticut. Went to New York City and I interviewed for a job in New York. I don't even know what job it was. I don't know what company it was. I got a LinkedIn message and this guy was like, hey, you should apply for our job. And I was like, all right, New York City. My brother works there. My sister has worked there. Like, that'd be so cool to live there. And I got, I walked out of the interview. My mom was like, how'd it go? And I was like, it went great. But what am I doing here? I'm not supposed to be in a suit. I'm not supposed to be wearing a suit right now. I'm 21 years old. I have the rest of my life to work like this. I was like, there's something. And that was the moment where it clicked. And I'm like, I have to do something else. And that's when the Instacart started. That's when TikTok started going crazy. And like. basically my whole journey started. Okay. Speaker 1 (8:29) Wait, I'm going to sidestep for a second because I get a lot of Instacart orders. I have a 12 year old. The Instacart people are always at our house. I'm just curious how that works. Are you always like sitting in your car waiting near a place to get a delivery? Like how does it work? Speaker 2 (8:44) Yes. So, I mean, this is a crazy story. So I was delivering in Connecticut and yes, you, you sit in your car, you wait for the order, you get the, you get the $70 Costco order and you're like, let's go. And it takes you like an hour and a half to find everything. You finally find it. But anyway, I moved to New York city. Speaker 1 (9:00) And wait, and you're getting like a $4 tip, right? Speaker 2 (9:03) Yeah. But you're like, if you, I played it right. And I was playing it smart where I was making like probably $400 a day doing Instacart deliveries. And it was over COVID. So it was also like, and after COVID a little bit, so everybody was ordering groceries. But then I moved to New York city with my ex-girlfriend, well, girlfriend at the time, now ex-girlfriend. And we were both Instacarting. We were both like riding city bikes. We're putting groceries, hoping that no one stole our city bike. We would literally park our city bikes outside of the store, go in, hoping, hoping, not like tracking the bike to make sure like if I'm in the back of the store and I can't see it, I'm like tracking the bike to make sure no one stole it, walked outside, put the groceries on the handles, um, park the bike again to bring it up a hundred stories where these rich people were living in New York penthouses. Um, giving good tips though. But, uh, Yeah, that's as much as all I can talk about. Speaker 1 (9:53) So wait, Speaker 2 (9:53) are Speaker 1 (9:53) Instacart people making their money on the tips or are they making it, you get a certain percentage that Instacart gives you? Speaker 2 (9:59) Yeah, there's a percentage Instacart gives you, but then you also make money. The tip, if someone tips you big, like that's most of your money is going to come from. Speaker 1 (10:06) Nice, okay. Speaker 2 (10:08) Yeah, I had some horror stories though. My first time Instacarting in New York City, I was riding a city bike. And I don't know if you've seen, you've ridden on every street in New York City, but there's two streets that have a real... Pretty steep incline that like Manhattan does not have inclines, but there are a couple where it's like, oh, okay. So I was riding my bike, not thinking about this. And I was riding down and my brakes like weren't working as well. It was like an older bike, I guess. And Speaker 1 (10:30) I had, Speaker 2 (10:30) I had nine bags on both sides. Like I'm, I'm holding them and also holding the handles and then holding them and holding the handles. Yeah. Truck flies by me and I stopped the bike and I literally see it in slow motion to this day. All of the groceries, except for like two of the bags. flew out onto the street. I'm really, the whole next like five days, I'm looking on TikTok to make sure no one got my video of me doing this. And I found two, this is turning into like an Instacart podcast. I Speaker