Founder's Story Episode Summary: "I Bootstrapped OddsJam to $160M—Everything I Learned Along the Way | Ep 221 with Alexander Monahan"

Release Date: May 16, 2025
Host: IBH Media

Introduction

In Episode 221 of "Founder's Story" by IBH Media, host Alex Monahan, the founder of OddsJam, shares his remarkable journey from a Stanford graduate and engineer to a successful entrepreneur who bootstrapped his company to a $160 million sale. This episode delves deep into the challenges, strategies, and personal experiences that defined Monahan's path to success in the burgeoning sports betting industry.

Early Entrepreneurship Journey

Alex Monahan opens up about his initial forays into entrepreneurship, highlighting the myriad of ideas he experimented with during his college years. Despite his passion for gambling and sports betting, none of his early ventures gained traction.

"Everyone has ideas for businesses, but they never really took off. I never really had an edge," says Monahan (02:26).

His pivotal moment came when he took a job at Susquehanna, a trading firm in Pennsylvania, just as sports betting was gaining legalization momentum. Immersed in an environment where sports betting became a common topic, Monahan's passion ignited, leading him to immerse himself deeply into data-driven sports betting.

Building OddsJam: Identifying the Gap

Monahan identified a significant gap in the sports betting market: the lack of comprehensive, data-driven tools for bettors. He envisioned OddsJam as the "Bloomberg Terminal of sports betting", aiming to provide real-time odds, consolidated data, and insightful content that could empower bettors to make informed decisions.

"There's nothing like it. All the content is horrible. It's just guys flexing Rolexes and Ferraris and claiming they can see the future," Monahan remarks (04:15).

This vision was born out of his personal frustration with the existing sports betting platforms, which lacked the depth and quality of information he sought as a serious bettor.

Bootstrapping and Early Growth

Monahan and his co-founder made the bold decision to quit their jobs and focus entirely on OddsJam. At just 24 years old, this move was both risky and exhilarating.

"We made some posts on Reddit, we made some posts in sports betting groups. And the product initially was priced at like $6 and very quickly started getting subscribers," Monahan explains (06:39).

Their initial strategy involved leveraging social media influencers to gain traction. However, they soon realized the limitations of this approach and pivoted to creating their own content. Monahan overcame his fear of public speaking by producing tutorials and educational videos, which significantly boosted their subscriber base.

"We kept making YouTube videos and saw immediate customer spikes. It was when we started creating our own content that we really took off," he notes (09:45).

Focusing primarily on YouTube and Twitter, OddsJam provided valuable, data-driven content that resonated with the sports betting community, facilitating rapid growth without relying heavily on paid influencers.

Navigating Challenges and Scaling Up

As OddsJam grew, Monahan faced typical entrepreneurial challenges, including hiring and management. Transitioning from a private life to a public-facing role required him to develop new skills and embrace content creation.

"I had to overcome a fear of public speaking and put myself out there consistently. It was a steep learning curve," he shares (14:02).

Monahan's strategic acquisition of smaller competitors and data providers gave OddsJam a competitive edge, enhancing their data accuracy and product offerings. This move solidified their position as a market leader.

The Acquisition: Selling for $160 Million

When OddsJam attracted the attention of larger players in the sports betting ecosystem, Monahan approached the acquisition process with deliberate focus and emotional balance.

"We had good bankers and lawyers during the sale process. I stayed heads down, focused on daily operations, ensuring that if the deal fell through, we still had a great business," Monahan explains (17:36).

The sale to a prominent company was not a sudden event but the culmination of sustained growth, strategic positioning, and robust financial metrics. Monahan emphasized the importance of building a resilient business that could thrive irrespective of the acquisition outcome.

Post-Acquisition Life and Continued Growth

Post-acquisition, Monahan remains actively involved with OddsJam, now part of a larger organization. Contrary to some entrepreneurs who face identity crises post-exit, Monahan finds stability and continued passion in his work.

"I'm still working on the same things, which I like. Life hasn't really changed since the company was bought," he states (24:16).

His approach to wealth accumulation was gradual and strategic, avoiding the pitfalls of sudden wealth-induced pressures. This steady growth allowed him to maintain work-life balance while still dedicating significant effort to expanding OddsJam's reach.

Insights on Entrepreneurship and Work-Life Balance

Monahan offers valuable insights for aspiring entrepreneurs, emphasizing the importance of passion and expertise in one's chosen field to sustain long working hours without burnout.

"I never felt burnt out because it's something I truly enjoy doing. If you're passionate and good at something, you can work long hours without it feeling like a grind," Monahan shares (28:28).

He also underscores the necessity of working smart, focusing on strategic growth, and outworking the competition by maintaining relentless dedication and avoiding distractions.

Final Thoughts and Advice

In closing, Monahan reflects on the essence of building a successful business:

"You have to work a lot, but it also boils down to working smart. Focus on driving customer value, executing on the right ideas, and maintaining a solid team," he advises (30:21).

His journey with OddsJam serves as an inspiring blueprint for entrepreneurs aiming to identify market gaps, leverage data-driven strategies, and build businesses that stand the test of time.

Key Quotes with Timestamps

• Alex Monahan (02:26): "Everyone has ideas for businesses, but they never really took off. I never really had an edge."

• Alex Monahan (04:15): "All the content is horrible. It's just guys flexing Rolexes and Ferraris and claiming they can see the future."

• Alex Monahan (06:39): "We made some posts on Reddit, we made some posts in sports betting groups. And the product initially was priced at like $6 and very quickly started getting subscribers."

• Alex Monahan (09:45): "We kept making YouTube videos and saw immediate customer spikes. It was when we started creating our own content that we really took off."

• Alex Monahan (14:02): "I had to overcome a fear of public speaking and put myself out there consistently. It was a steep learning curve."

• Alex Monahan (17:36): "We had good bankers and lawyers during the sale process. I stayed heads down, focused on daily operations, ensuring that if the deal fell through, we still had a great business."

• Alex Monahan (24:16): "I'm still working on the same things, which I like. Life hasn't really changed since the company was bought."

• Alex Monahan (28:28): "I never felt burnt out because it's something I truly enjoy doing. If you're passionate and good at something, you can work long hours without it feeling like a grind."

• Alex Monahan (30:21): "You have to work a lot, but it also boils down to working smart. Focus on driving customer value, executing on the right ideas, and maintaining a solid team."

Conclusion

Alex Monahan's story is a testament to the power of passion, resilience, and strategic thinking in entrepreneurship. By identifying a niche in the sports betting industry and meticulously building OddsJam from the ground up, Monahan exemplifies how dedication and smart work can lead to extraordinary success. His insights provide invaluable lessons for current and aspiring entrepreneurs aiming to navigate their own paths to greatness.

For more inspiring entrepreneurial stories, tune into "Founder's Story" by IBH Media.