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!
Jun 23, 2025
01:06:19
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
Stay connected with the Trading Secrets Podcast!
Instagram: @tradingsecretspodcast
Youtube: Trading Secrets
Facebook: Join the Group
All Access: Free 30-Day Trial
Trading Secrets Steals & Deals!
IDEO U:
Feel like you're falling behind on Al? Boost your impact and drive your team forward with IDEO U's online learning experiences, including their new Al & Design Thinking Programs. You'll master machine learning with IDEO's signature human-centered approach. Class starts soon, so enroll today! For a limited time, IDEO U is offering 15% OFF SITEWIDE! Go to IDEOU.com/TRADINGSECRETS.
UpWork:
Upwork is the hiring platform designed for the modern playbook, where you can find, hire, and pay expert freelancers who can deliver results from day one. Perfect for businesses on tight budgets, fast timelines, and zero room for error. For a $200 credit after spending $1,000 in your first thirty days, Visit Upwork.com/save right now for this great offer.
Quince:
As the temps start rising, fulfill that familiar urge to refresh your closet with Quince. Their clothes are timeless, lightweight, and far more elevated than anything else at this price. Give your summer closet an upgrade-with Quince. Go to Quince.com/tradingsecrets for free shipping on your order and 365-day returns.
This Is Small Business Podcast:
if you're building something, dreaming big, or just constantly thinking about your next move... I've got a podcast you need to check out. It's called This Is Small Business hosted by Andrea Marquez, and Season 6 just dropped. If you're plotting your next move - maybe launching that side hustle, scaling a business, or pivoting hard - go check out This Is Small Business.
Avelo Air
Tired of long layovers and airport chaos? Let's change that by saying Hello to Avelo. Avelo Airlines offers nonstop service to over 50 destinations across the U.S, including Nonstop service to 30 cities from New Haven and Hartford. That vacation you've been thinking about? It's just a click away. Book your trip now at AveloAir.com and use promo code SECRETS20 for $20 off round trip base fares* when you book by 6/30/25
*Restrictions apply. Discount applies to round trip base fares only. Valid for travel through 11/30/25. Must be purchased by 11:59 p.m. PT on 6/30/25. See AveloAir.com Contract of Carriage for full details.
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
Stay connected with the Trading Secrets Podcast!
Instagram: @tradingsecretspodcast
Youtube: Trading Secrets
Facebook: Join the Group
All Access: Free 30-Day Trial
Trading Secrets Steals & Deals!
IDEO U:
Feel like you're falling behind on Al? Boost your impact and drive your team forward with IDEO U's online learning experiences, including their new Al & Design Thinking Programs. You'll master machine learning with IDEO's signature human-centered approach. Class starts soon, so enroll today! For a limited time, IDEO U is offering 15% OFF SITEWIDE! Go to IDEOU.com/TRADINGSECRETS.
UpWork:
Upwork is the hiring platform designed for the modern playbook, where you can find, hire, and pay expert freelancers who can deliver results from day one. Perfect for businesses on tight budgets, fast timelines, and zero room for error. For a $200 credit after spending $1,000 in your first thirty days, Visit Upwork.com/save right now for this great offer.
Quince:
As the temps start rising, fulfill that familiar urge to refresh your closet with Quince. Their clothes are timeless, lightweight, and far more elevated than anything else at this price. Give your summer closet an upgrade-with Quince. Go to Quince.com/tradingsecrets for free shipping on your order and 365-day returns.
This Is Small Business Podcast:
if you're building something, dreaming big, or just constantly thinking about your next move... I've got a podcast you need to check out. It's called This Is Small Business hosted by Andrea Marquez, and Season 6 just dropped. If you're plotting your next move - maybe launching that side hustle, scaling a business, or pivoting hard - go check out This Is Small Business.
Avelo Air
Tired of long layovers and airport chaos? Let's change that by saying Hello to Avelo. Avelo Airlines offers nonstop service to over 50 destinations across the U.S, including Nonstop service to 30 cities from New Haven and Hartford. That vacation you've been thinking about? It's just a click away. Book your trip now at AveloAir.com and use promo code SECRETS20 for $20 off round trip base fares* when you book by 6/30/25
*Restrictions apply. Discount applies to round trip base fares only. Valid for travel through 11/30/25. Must be purchased by 11:59 p.m. PT on 6/30/25. See AveloAir.com Contract of Carriage for full details.