Sleepy Hallow Net Worth 2025, Age, Income, Real Name, Bio

Timothy Daniel Pool Bio

Sleepy Hallow, the Brooklyn-based rapper recognized for his melodic drill sound and emotionally layered lyrics, has become a leading name in modern hip-hop. As of 2025, Sleepy Hallow’s net worth stands at 6 million USD, thanks to a flourishing music career, viral streaming success, and smart business decisions. He emerged from the underground drill scene to charting success, solidifying his position among the most authentic voices of his generation.

The rapper’s journey, marked by pain, authenticity, and resilience, continues to inspire fans worldwide. His influence extends beyond music and into culture, fashion, and mental health discussions. With a blend of artistry and business acumen, Sleepy Hallow has steadily built wealth without sacrificing his originality.

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Early Beginnings and Breakthroughs in Music

Born as Tegan Chambers in Flatbush, Brooklyn, Sleepy Hallow faced the tough realities of inner-city life from an early age. These experiences shaped his storytelling and emotional depth. He began releasing music in his teens, often collaborating with Sheff G, another prominent name in the Brooklyn drill scene. His career took off when he and Sheff G dropped “Flows” and later “Breakin Bad (Okay),” which gained local traction. However, the real turning point was the release of “Deep End Freestyle” in 2020. Fueled by a viral TikTok trend, the song caught fire online and was streamed over 200 million times, generating massive royalty revenue and putting Sleepy Hallow in the national spotlight.

The overnight success of that single gave him leverage with labels, higher streaming payouts, and a broader fan base. From that point, Sleepy was no longer just a local artist—he became a national name with global appeal.

Revenue From Music and Streaming Platforms

Music remains Sleepy Hallow’s core source of wealth. With over 2 billion combined streams across platforms like Spotify, Apple Music, and YouTube, he earns significant royalty income annually. By 2021, his streaming revenues had crossed 1 million USD, driven by the success of “2055,” “Die Young,” and other hits.

In 2022, Sleepy released his highly anticipated album, which pushed his yearly music earnings to 1.4 million USD. With every new track, his catalog continues to generate passive income from fans replaying his earlier works. By 2023, the total streaming revenue from all platforms combined reached 1.8 million USD, and by 2024, his cumulative music earnings stood at 4.5 million USD.

He has consistently been featured on popular playlists like RapCaviar and Most Necessary, which greatly boost visibility. This consistent presence on curated lists ensures long-term income flow, helping maintain a steady stream of royalty payments every month.

Touring and Performance-Based Earnings

Live shows and tours significantly contribute to Sleepy Hallow’s income. In 2022, he embarked on his first headlining tour across the United States. Performing in 40+ cities, he earned approximately 15,000 USD per show, bringing his total earnings from touring that year to around 600,000 USD. By 2023, due to his increased popularity and growing audience, he began commanding higher booking fees of 30,000 USD to 50,000 USD per concert. He also featured in major festivals, including Rolling Loud and Summer Jam, which paid upwards of 80,000 USD for a single performance.

From 2022 to 2024, his live appearances generated over 2 million USD, with the bulk coming from ticket sales, festival fees, and merchandise sold at events. These earnings not only added to his net worth but also helped expand his brand’s recognition in markets outside of New York.

Clothing Merchandise and Brand Presence

Sleepy Hallow ventured into fashion by launching limited-edition clothing drops. His merchandise lines include hoodies, beanies, and tees inspired by his lyrics and album artwork. These were sold primarily through his website and at concerts, where demand was consistently high. Between 2021 and 2024, his clothing brand’s sales generated an estimated 900,000 USD. Fans often shared their Sleepy Hallow gear on social media, fueling organic promotion and driving up demand with every new design drop.

His understanding of youth fashion trends allowed him to keep his brand authentic while tapping into an additional income stream that required relatively low investment. This merchandise’s success not only reflected his cultural relevance but also contributed meaningfully to his total wealth.

Major Record Deals and Label Collaborations

Sleepy Hallow’s signing with RCA Records in partnership with Winners Circle Entertainment played a crucial role in his financial growth. This record deal came with an upfront advance of approximately 500,000 USD, along with performance-based royalties and bonuses tied to album success. Unlike many artists under major labels, Sleepy retained partial ownership of his masters through Winners Circle, allowing him to receive a larger share of long-term royalties. This deal structure benefited him enormously by giving him creative freedom and better profit margins.

In addition, his role within the Winners Circle collective gave him equity-like participation in group projects and allowed him to benefit from Sheff G’s success and other affiliated artists. These internal royalties added another 300,000 USD to his net worth between 2022 and 2024.

Social Media Impact and Influencer Revenue

With over 1.5 million Instagram followers and millions of views across TikTok and YouTube, Sleepy Hallow holds valuable digital influence. He uses his platforms to promote upcoming tracks, share lifestyle content, and engage with fans on a personal level. This digital presence translated into brand deals and influencer earnings. Companies in fashion, music tech, and lifestyle sectors offered Sleepy promotional contracts, earning him an additional 250,000 USD in 2023 and 300,000 USD in 2024.

More than just monetization, his social media strategy enhances fan loyalty and makes every music drop feel like a major event. The direct-to-fan connection boosts pre-saves, first-week sales, and merchandise sell-outs.

Personal Investments and Asset Building

Sleepy Hallow has used a portion of his earnings to build long-term assets. He purchased a house in New York valued at 850,000 USD, which serves both as a residence and a studio space. This investment reflects his preference for staying close to his roots while building equity. In recent years, he began exploring real estate investment, acquiring a rental property in New Jersey estimated at 500,000 USD. Additionally, he invested approximately 100,000 USD in cryptocurrency and digital art NFTs, though he remains cautious in that space.

His focus has been on sustainable financial growth, not flashy spending. While he owns luxury items like a Range Rover and custom jewelry worth around 200,000 USD, he avoids excessive displays of wealth and prefers reinvesting earnings into music and business ventures.

Legal Challenges and Financial Consequences

In 2022, Sleepy Hallow and members of the Winners Circle crew were indicted on conspiracy charges, resulting in a temporary halt to some of his activities. Though he was not the central figure in the case, the association brought challenges. Legal expenses, public relations damage control, and tour cancellations led to a temporary financial setback. Reports indicate that he spent close to 300,000 USD handling the case, including legal fees and canceled appearances.

Despite this, Sleepy Hallow rebounded by returning to music quickly, releasing new singles that climbed the charts and reestablishing himself as a consistent performer. The situation may have affected his short-term earnings, but ultimately made his brand even more resilient.

Year-to-Year Financial Success

Sleepy Hallow’s journey to financial success has been steady, shaped by both consistency and big career moments. His income has grown each year, even with challenges like legal issues and industry changes. In 2020, his viral hit “Deep End Freestyle” earned him around 400,000 USD, mostly from streaming and downloads. Although live shows were limited due to the pandemic, his popularity surged. In 2021, his income jumped to 1.1 million USD, thanks to hit songs, local shows, and a 500,000 USD deal with RCA Records. By 2022, he earned around 1.6 million USD, supported by national tours, music sales, and merchandise. In 2023, even with legal troubles, he still made 1.9 million USD, mainly from streaming and brand deals. His comeback in 2024 was strong, bringing in 2.3 million USD with new music, tours, and digital growth. Now in 2025, he is expected to earn more than 2.5 million USD, with strong support from fans and new projects.

Sleepy Hollow’s Influence on Hip-Hop and Youth Culture

Beyond numbers, Sleepy Hallow holds cultural weight, especially among young listeners navigating emotional and social challenges. His music often addresses themes like depression, betrayal, and personal growth, connecting deeply with fans looking for more than just catchy beats. He has been praised for normalizing mental health conversations in hip-hop, often speaking openly about anxiety and sadness. This honesty gives him credibility, not just as a rapper but as a voice for vulnerable youth. His rise represents a shift in the genre, where emotion and reflection can be just as powerful as bravado and aggression.

Sleepy Hallow’s style, a blend of trap beats, melodic flow, and dark lyrical content, has inspired a new wave of artists in Brooklyn and beyond. The authenticity he brings to the table allows him to stand out in a crowded industry.

Expansion Through Collaborations and Partnerships

Collaborations have been a critical driver of Sleepy Hallow’s visibility and financial growth. Working with Sheff G from the beginning gave his career the initial momentum. Together, their chemistry brought hits that resonated in clubs, cars, and headphones across America. As his reach grew, Sleepy Hallow began collaborating with other rising stars and established names, including Lil Tjay and Polo G. These joint ventures not only expanded his sound but brought new audiences into his fan base. Every collaboration also translated into new revenue streams—shared YouTube monetization, cross-merchandising opportunities, and streaming boosts on platforms where these artists had stronger footholds.

In 2024 and 2025, Sleepy Hallow started eyeing partnerships beyond music. He held talks with fashion startups for capsule collections and explored mental health tech collaborations. These non-traditional collaborations are expected to bring in 500,000 USD in 2025 alone, further increasing his net worth and extending his brand’s impact.

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Lifestyle, Spending Habits, and Financial Discipline

While Sleepy Hollow does indulge in luxury occasionally, his lifestyle is more restrained compared to some of his peers. He’s known to keep a relatively low profile, avoiding media attention outside of music. He currently owns two properties, his main residence in New York, worth around 850,000 USD, and a rental apartment in New Jersey valued at 500,000 USD. Together, these add real equity to his wealth portfolio. Sleepy’s car collection is modest but stylish, including a Range Rover, a custom Dodge Charger, and a BMW X6. The total value of his cars is approximately 200,000 USD.

He’s also invested in studio equipment and sound engineering gear, treating his work as both passion and business. His focus remains on building sustainable income streams rather than engaging in flashy spending sprees. Financial advisors close to him suggest that he save over 40 percent of his annual income and is working towards establishing a business entity for managing artist rights and royalties, a move that could eventually add millions more to his long-term net worth.

Real Estate and Business Ventures

Real estate has become a secondary but reliable source of income for Sleepy Hallow. The New Jersey property, which he rents out, yields approximately 3,000 USD monthly in rental income. He plans to expand this portfolio with another residential property in Atlanta by the end of 2025. Apart from real estate, He is exploring business ventures in the music industry. He is rumored to be developing a creative agency under the Winners Circle brand that would provide studio access, mentorship, and promotional support for emerging artists. Initial investments in the venture are estimated at 100,000 USD, with a projected growth of 500,000 USD in valuation within two years.

This strategic diversification positions him not just as an artist but as an entrepreneur with the potential to shape the next generation of hip-hop talent.

Social Impact and Mental Health Advocacy

Sleepy Hallow has not only built wealth but is also building a legacy. His fans often credit his music with helping them through dark times. Recognizing this, he has become more vocal about the importance of mental health awareness. He frequently uses his social media platforms to post messages about healing, growth, and self-care. In 2025, he is expected to launch a non-profit focused on youth mental health awareness in urban communities. The organization, tentatively named “Mind of Mine,” will offer music therapy, counseling sessions, and safe spaces for inner-city youth.

This endeavor is not only meaningful socially but also adds another layer of respect and depth to Sleepy Hallow’s public image. He is shaping his legacy not only through his lyrics but through concrete actions that uplift others.

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Upcoming Projects and Future Growth

Sleepy Hallow is not slowing down. He is currently working on his next full-length album, expected to drop in late 2025. Insiders report that the album features collaborations with top-tier producers and possibly an international artist, marking his push into global markets. He’s also planning an international tour in 2026, covering cities in Europe, Australia, and Canada. This tour is expected to earn him around 3 million USD, given his increasing demand outside the United States.

Additionally, a documentary project chronicling his journey from Flatbush to fame is in pre-production. If released on platforms like Netflix or Hulu, it could earn Sleepy a one-time licensing fee of approximately 1 million USD, further cementing his financial and cultural footprint.

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Final Verdict

Sleepy Hallow’s rise from the streets of Brooklyn to becoming one of the most recognized melodic drill artists in the world is a powerful example of talent meeting opportunity. His story is one of steady progress, resilience in the face of adversity, and a deep connection with fans that goes far beyond music charts. From a viral TikTok moment in 2020 to headlining tours, major label deals, and expanding brand partnerships, he has transformed every milestone into meaningful financial gain. As of 2025, Sleepy Hallow’s net worth stands confidently at 6 million USD, built on strong foundations like streaming royalties, live performances, merchandise sales, and real estate.

Looking ahead, Sleepy Hallow is more than capable of surpassing 10 million USD in net worth within the next few years, especially if he continues delivering hit projects and leveraging his influence into broader ventures. He is not just a rapper; he is an evolving entrepreneur, cultural icon, and voice for the unheard. His journey so far proves that when authenticity meets strategy, both fame and fortune follow.