Trading Secrets Episode 240: Jackson Olson – From Instacart to Gatorade Deals with the Savannah Bananas
Podcast Information:
- Title: Trading Secrets
- Host/Author: Audioboom Studios
- Episode: 240
- Guest: Jackson Olson
- Release Date: June 23, 2025
Introduction
In this captivating episode of Trading Secrets, host Jason Tardick welcomes social media personality and Savannah Bananas baseball star, Jackson Olson. Recorded in Nashville, Tennessee, the conversation delves deep into Jackson's unconventional career path, remarkable social media growth, and his pivotal role with the fan-centric Savannah Bananas team.
Jackson Olson's Early Career and MLB Draft [04:23]
Jackson Olson, a former collegiate baseball player, shared his journey from aspiring to be drafted into Major League Baseball (MLB) to redefining his career through content creation.
Key Points:
- College Success: Jackson excelled at Hartford, boasting a 3.20 GPA and being named Scholar Athlete of the Year.
- Draft Decision: Despite receiving an offer from the Arizona Diamondbacks, Jackson declined to return for his senior year to secure a better draft position and potentially higher signing bonuses. This decision, although initially daunting, led him to his "second dream."
- Change in MLB Draft Rules: The COVID-19 pandemic reduced the MLB draft from 40 rounds to only 5, limiting opportunities for players like Jackson who weren't in the top tier.
Notable Quote:
"It was the best decision I ever made to decline that because now I'm living my second dream." — [04:41]
Transition to Content Creation [09:43]
After not being drafted, Jackson pivoted to content creation while delivering groceries for Instacart in New York City. This period was crucial in building his social media presence.
Key Points:
- Instacart Gig: Making approximately $300 a day by delivering groceries on a city bike.
- Content Creation: Filming and posting about his Instacart experiences on TikTok, amassing over 2.5 million followers.
- Financial Insight: Jackson earned more from TikTok’s Creator Fund ($12 million views) than from his Instacart job.
Notable Quote:
"I was making money on TikTok from those videos than I was actually making from doing Instacart." — [13:19]
Growth of Social Media Presence [16:35]
Jackson's proactive approach to content creation led to significant opportunities beyond Instagram and TikTok.
Key Points:
- MLB Partnership: Becoming part of MLB’s inaugural class of social media content creators in 2021. Jackson exceeded expectations by producing 75 videos instead of the required 12, positioning himself as MLB’s top creator.
- GameTime Collaboration: Partnered with GameTime to rank California stadiums, integrating promotional codes and driving ticket sales.
- Savannah Bananas Connection: A viral video about the Savannah Bananas caught the attention of Jesse Cole, the team’s owner, resulting in Jackson joining the team.
Notable Quote:
"I was trying to flood the feed. And they sent me out a Major League baseball tour. And they were like, let's rank every single stadium." — [17:01]
Joining the Savannah Bananas [21:32]
Jackson details his transition to the Savannah Bananas, a semi-pro baseball team known for their entertainment-focused "Banana Ball."
Key Points:
- Initial Involvement: Initially hired to create content, Jackson soon participated in tryouts and secured a permanent spot on the team.
- Banana Ball Rules: Emphasizes fan engagement with unique rules like foul balls caught by fans resulting in outs and rapid-paced games lasting only two hours.
- Fan-Centric Approach: The team prioritizes interactions, autographs, and in-game entertainment, attracting large crowds by breaking down traditional barriers between players and fans.
Notable Quote:
"We break down the barrier between fan and player. Banana ball is baseball with nine rules... it's like WWE a little bit with crazy antics." — [28:31]
Brand Deals and Sponsorships [33:04]
Jackson’s growing influence has attracted significant brand deals, enhancing both his personal brand and the Savannah Bananas' visibility.
Key Points:
- Reebok Partnership: Joined a roster including sports legends, benefiting from Reebok’s extensive marketing reach.
- Gatorade Athlete: Secured a full-year partnership with Gatorade, marking a milestone in athlete-influencer collaborations.
- Capital One Collaboration: Ongoing partnerships showcasing Capital One cardholder benefits at major sporting events.
- Creative Freedom: Unlike traditional athletes constrained by exclusivity clauses, Jackson enjoys the flexibility to engage with multiple brands freely.
Notable Quote:
"Gatorade's pretty legit... it's a full-blown year partnership. Gatorade athlete." — [34:55]
Future Aspirations [36:52]
Looking ahead, Jackson envisions a multifaceted career blending sports, media, and personal passions.
Key Points:
- Long-Term with Bananas: Aims to continue his role with the Savannah Bananas while exploring other ventures.
- Media Opportunities: Open to hosting game shows or creating a food-focused series, inspired by personalities like Anthony Bourdain.
- No Fixed Dreams: Focused on following his energy and passions without rigid long-term plans.
Notable Quote:
"I'm just posting shorts... Where can people find everything you have going on on social media? Jackson Olsen underscore on everything." — [49:20]
Personal Insights and Advice [43:24]
Jackson shares practical tips for emerging content creators and insights into maintaining authenticity.
Key Points:
- Stay Authentic: Emphasizes being true to oneself and focusing on the fan experience.
- Content Strategy: Advises new creators to hook viewers within the first five seconds by clearly stating the video's purpose.
- Financial Prudence: Despite his success, Jackson remains a disciplined spender, prioritizing family and essential expenditures over lavish purchases.
Notable Quote:
"Just be yourself and be fans first... think about that 12-year-old that's watching you and emulating everything you're doing." — [43:24]
Conclusion and Final Thoughts [47:47]
As the episode wraps up, Jackson reflects on the synergistic relationship between fan engagement and personal branding, highlighting the transformative potential of blending sports with digital influence.
Key Points:
- Fan First Philosophy: The Savannah Bananas' focus on fans has revolutionized their business model, surpassing traditional MLB attendance rates.
- Influence Over Salary: Jackson suggests that brand deals and social media influence can potentially out-earn conventional MLB salaries.
- Changing Sports Landscape: The merging of entertainment and sports, driven by social media, signals a new era where fan-centric approaches can redefine success.
Notable Quote:
"The only reason I'm a Savannah Banana, only reason I worked with MLB, only reason I'm here right now is because I was able to keep people invested." — [47:47]
Notable Quotes with Timestamps
- [04:41] Jackson Olson: "It was the best decision I ever made to decline that because now I'm living my second dream."
- [13:19] Jackson Olson: "I was making money on TikTok from those videos than I was actually making from doing Instacart."
- [28:31] Jackson Olson: "We break down the barrier between fan and player. Banana ball is baseball with nine rules... it's like WWE a little bit with crazy antics."
- [34:55] Jackson Olson: "Gatorade's pretty legit... it's a full-blown year partnership. Gatorade athlete."
- [43:24] Jackson Olson: "Just be yourself and be fans first... think about that 12-year-old that's watching you and emulating everything you're doing."
- [47:47] Jackson Olson: "The only reason I'm a Savannah Banana, only reason I worked with MLB, only reason I'm here right now is because I was able to keep people invested."
Key Takeaways
- Unconventional Career Path: Jackson’s journey illustrates the power of adaptability and leveraging digital platforms to create unique career opportunities beyond traditional sports pathways.
- Power of Content Creation: Building a substantial social media presence can lead to significant brand partnerships and influence, often surpassing traditional income streams in emerging industries.
- Fan-Centric Models: Emphasizing fan engagement and entertainment can revolutionize sports teams’ business models, attracting larger audiences and enhancing brand loyalty.
- Authenticity and Consistency: Staying true to one’s personality and consistently delivering engaging content is crucial for sustained growth and influence.
- Future of Sports and Entertainment: The integration of digital media with traditional sports is reshaping how athletes engage with fans and monetize their talents, paving the way for new business models in the sports industry.
Final Thoughts
Episode 240 of Trading Secrets offers an inspiring glimpse into the evolving landscape of sports and digital media through Jackson Olson’s story. From delivering groceries to securing multi-million dollar brand deals, Jackson exemplifies the modern athlete-influencer who leverages authenticity and fan engagement to carve a unique and lucrative career path. As sports continue to adapt to changing audience preferences, models like the Savannah Bananas highlight the potential for fan-centric approaches to redefine success in the industry.
Connect with Jackson Olson:
- TikTok: @JacksonOlson_
- Instagram: @JacksonOlson_
- YouTube: Jackson Olson Shorts
Stay Tuned: Don’t miss upcoming episodes where Trading Secrets explores more groundbreaking stories and strategies to help you navigate the financial and professional world successfully.