He Sold His Newsletter To Barstool, Then Bought It Back
Feb 17, 2025
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Tyler Morin, founder of The Water Coolest, shares his remarkable journey from financial consulting to creating a humor-infused newsletter. He candidly discusses audience growth strategies and lessons learned from his early sponsorships. Tyler delves into the intriguing experience of selling his newsletter to Barstool Sports and the challenges of reclaiming it. He also tackles the evolving landscape of ad monetization and emphasizes the importance of authenticity in a competitive email newsletter market.
Tyler Morin's journey in creating The Water Coolest stemmed from a desire to provide engaging and relatable financial news for younger audiences.
Strategic partnerships with social media influencers played a crucial role in rapidly growing the newsletter's subscriber base and establishing its presence in the finance community.
After reacquiring The Water Coolest from Barstool Sports, Morin transitioned to consulting, sharing valuable insights on audience engagement and monetization strategies for aspiring media creators.
Deep dives
Founding The Water Coolest
The journey of creating The Water Coolest began from a personal need for engaging financial news. Having worked in financial services and grown tired of the monotonous reporting from major outlets like the Wall Street Journal and Bloomberg, the founder sought to provide a voice that resonated with the younger demographic. Initially starting with a blog called Entry Revel, the transition took place when the founder recognized the potential for a newsletter that combined finance with humor and relatability. Ultimately, this led to the birth of The Water Coolest in 2017, marked by a distinctively irreverent tone aimed at making finance both informative and enjoyable.
Building an Audience Through Collaborations
The initial growth of The Water Coolest was largely attributed to strategic partnerships with social media influencers in the finance niche. By leveraging relationships with meme accounts and finance personalities, the newsletter gained significant exposure and traction, leading to thousands of new subscribers. These influencers helped cement the newsletter's position within the finance community, allowing the founder to attract individuals from prestigious firms like Morgan Stanley and Goldman Sachs. This approach exemplified the importance of finding the right channels and engaging early adopters to kickstart audience building.
Monetization Strategy and Growth Challenges
The transition from a growing subscriber base to monetization proved to be a nuanced process, with the founder initially hesitant to pursue revenue opportunities. Recognizing the need to sustain the newsletter, monetization began around the 25,000 to 30,000 subscriber mark after much deliberation. This involved offering paid advertising space to relevant brands targeting a professional audience. With hindsight, the founder emphasized the importance of monetizing sooner to better understand the audience and provide value, a lesson drawn from the overall slow grind of growing The Water Coolest.
Acquisition by Barstool Sports
The acquisition of The Water Coolest by Barstool Sports in late 2021 represented a significant turning point for the newsletter. Embracing the success of meme stocks and the surge in retail investing, Barstool sought to expand its presence in the finance sector and recognized the potential of The Water Coolest. The founder was drawn to Barstool due to its alignment with the brand's irreverent style, making it a natural fit. While navigating negotiations, the founder aimed to retain the distinct voice of the newsletter while also leveraging Barstool's expansive platform for growth.
Post-Barstool Transition and Consulting Services
After reacquiring The Water Coolest following its fluctuating partnership with Barstool, the founder faced new challenges in rebuilding the brand independently. Recognizing the valuable insights gained from this experience, the founder began offering consulting services to other aspiring media creators. The consulting focuses on helping individuals progress from initial stages of their newsletters to more established businesses, emphasizing the importance of audience engagement and monetization strategies. This pivot allows the founder to share knowledge in an ever-evolving media landscape while continuing to push The Water Coolest forward.
Tyler Morin is the founder of The Water Coolest, a newsletter that offers irreverent takes on business and finance news. He shares insights on audience growth, monetization, Barstool Sports’ acquisition, reclaiming his newsletter, and the future of ad-driven and B2B content.
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