Shark Tank Star Built a $1M Side Hustle Mailing History Letters

A simple love for history turned into a unique subscription business. It later grew into a million-dollar success and earned a spot on Shark Tank.

Liya Shanawas
Ari Siegel
Ari Siegel on Shark Tank (Image Credit: ABC)

Some business ideas come from deep research or market gaps. Others start with personal passion. That’s exactly what happened with Ari Siegel, who turned his love for history into a unique subscription business. What began as a small project eventually grew into a $1M+ business and has since crossed $2M in revenue, even earning a spot on Shark Tank Season 16.

This story is about curiosity, persistence, and finding a creative way to connect people with the past. It also stands out as a strong example of Shark Tank subscription business success and a growing direct-to-consumer brand.

A Simple Idea Inspired by History

Ari Siegel always loved history. Growing up, he listened to stories from his grandfathers, who had both served in World War II. These early experiences helped him build a strong connection with the past and made history feel real to him.

That feeling grew even stronger when he worked as an intern at the U.S. Senate. One day, while visiting the Library of Congress, he came across a letter written by President Abraham Lincoln. Seeing it in person left a strong impression on him and later inspired what would eventually become a successful niche e-commerce business.

Siegel decided to recreate historical documents and share them with family and friends. They asked for them regularly. That’s when the idea of a subscription began to take shape. In 2019, Siegel launched History By Mail using Shopify and spent a small amount on Facebook ads.

Turning that inspiration into a business was the next challenge.

Building the Business From Scratch

In the early stages, all aspects of the business were handled independently, from product creation to marketing and customer service. Each document required careful work. This included finding meaningful historical pieces, securing rights to use them, and recreating them in a way that felt authentic.

Along with the document, he also wrote a story to explain its importance. This added depth and made the experience more engaging for customers. Over time, what started as a one-person effort grew into a small remote team handling different parts of this subscription business.

However, the journey was not without challenges. Scaling logistics, maintaining consistent quality, and managing customer churn in subscription services became important areas to address as the business expanded.

The Power of Partnerships

One big turning point came in 2020 when Siegel partnered with Uncommon Goods. Getting this partnership was not straightforward. He spent a lot of time reaching out, sending samples, and trying to stand out in a competitive space.

This partnership became a turning point in scaling the business. Eventually, a buyer decided to take a chance on his idea. Interestingly, his product became one of the first subscription-style offerings on the platform. This exposure helped grow the History By Mail revenue significantly.

It also introduced new challenges. Managing a subscription business is more complex than selling a one-time product. Customers may pause, cancel, or change plans, requiring better systems and customer support.

Preparing for Shark Tank

Getting the chance to appear on Shark Tank was a big moment. Siegel knew how competitive the show was, so he prepared intensely. He practiced for months, studying past episodes and predicting the kinds of questions the sharks might ask.

He even created mock setups with cardboard cutouts of the sharks to simulate the experience. On top of that, he worked with a Broadway producer to improve his presentation skills. This preparation played a key role in the eventual Ari Siegel Shark Tank deal.

The Shark Tank Deal

When Siegel finally stepped onto the Shark Tank stage, he was ready. He showcased several documents, including the check used to purchase Alaska. These unique pieces helped grab attention and sparked curiosity among the Sharks.

The Sharks questioned scalability, customer retention, and long-term demand, making the pitch more intense. Despite this, he impressed them with his clarity and product uniqueness.

He secured a deal with Barbara Corcoran and Daniel Lubetzky, though only Daniel continued after due diligence. Having the right partner made a big difference. With Daniel’s support and experience, the business gained valuable guidance and resources.

After appearing on Shark Tank, the exposure brought in new customers and helped build trust in the brand. While it initially focused on gifting, Siegel realized that this approach made sales seasonal. He started exploring new areas like corporate gifting, schools, and museums.

Impressive Growth Over the Years

The growth of this direct-to-consumer brand has been remarkable. In 2019, it made just $2,300. Within a year, that number jumped significantly after the Uncommon Goods partnership.

By 2023, the business crossed $1 million in revenue and continued growing into the multi-million-dollar range. This more realistic phrasing strengthens credibility around History By Mail revenue.

One of the most meaningful milestones came when the company sent out its one millionth letter. For Siegel, this represented more than numbers. It showed the emotional impact of the product.

For many customers, these letters are a tangible connection to history. This emotional angle is what makes the history subscription service stand out from typical subscription boxes or general educational products.

The Real Lesson Behind the Success

While passion helped start this journey, it was not the only factor behind success. Building a niche e-commerce business requires constant problem-solving and adaptability.

This model shares similarities with other subscription box businesses but stands out because of its educational and emotional value. It shows how even simple ideas can evolve into scalable ventures.

What started as a passion project turned into a scalable business, proving that even niche ideas can build powerful, lasting brands.

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Liya Shanawas is a writer, editor, and brand strategist whose work has appeared in major publications, including The New York Times, HuffPost, Vogue, InStyle, Khaleej Times, and HelloGiggles. She previously served as a features editor at Dua Lipa’s editorial platform Service95 and has written widely on culture, fashion, business, and lifestyle. With a background in journalism, storytelling, and brand strategy, Liya writes about business, culture, and innovation, bringing clarity and perspective to modern ideas and emerging trends.
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