future within an email from your past self – that's the essence of FutureMe, the brainchild of Matt Sly. A fifth-grade assignment on writing a letter to the future stuck with Matt and eventually transformed into a life-altering concept.

Today, we take a deep dive into the inspiring narrative of how a seemingly simple act of creativity turned into a revolutionary business idea that has resonated with millions around the globe.

 I remembered as a 5th grader writing my future self a (physical) letter and handing it to my teacher. I never got that letter back. And on that run, I wondered what I'd written - realizing I'd never know. I also recognized that building software to "deliver letters to the future" wouldn't be all that hard. - Matt Sly.

Setting the Stage in Tech's Accidental Playground

Before the dawn of FutureMe, Matt had his fair share of stints in the tech industry during its volatile early days.

The dot-com bust of the early 2000s saw him pivot from high-flying startups to the more stable, yet equally fulfilling, arena of teaching high school math and computer science.

But as fate would have it, Matt's heart never strayed far from the tech world, and a childhood assignment would soon catalyse his entrepreneurial spirit.

A Letter to the Future, A World of Opportunity

Matt Sly wasn't just about to build his future; he wanted to share that potential with the world. With a vision to digitize the raw emotion and introspection in a letter addressed to one's future self, he embarked on a mission to create a digital time capsule.

When he sold FutureMe for what he modestly terms as "life-changing money," he not only made his future self proud but also struck a chord with countless individuals who found solace and inspiration within the realm of his creation.

Living in San Francisco, post dot-com boom and bust, we told a few friends, who said a few others...and in the intervening decades, through an admittedly mystifying mix of persistence, creativity and (most of all) luck, FutureMe grew into an enduring "indie" Internet brand, with many millions of users writing and receiving letters, and sharing their experience. - Matt Sly.

Coding the Consistent and Simple Future

Matt kept the FutureMe interface disarmingly uncomplicated in the nascent stages, comprising just five PHP files. This simplicity facilitated a conversion rate that most businesses can only dream of, with 32% of website visitors becoming heartfelt letter writers.

The early essence of FutureMe was akin to therapy – a stream of consciousness dispatched to the future, clearing the mental clutter along the way.

A Community of Visionaries

FutureMe didn't just become a platform for self-reflection; it fostered a vibrant community. Testimonials weren't solicited – they were shared expansively on social media and by the press, propelling the concept to new heights with each heartfelt story.

From apprehensive teens to nostalgic grandparents, the platform welcomed a spectrum of users who found a sense of humanity and connectivity in this unique act.

An Unfolding Future

The path could have been smoother sailing. Financial prudence and an unwavering belief in his service's value meant that Matt drove FutureMe's growth with parsimony.

The dedication yielded an unexpected lesson when Matt introduced a "pay-what-you-want" model, discovering that users often paid more when given a choice. The subsequent revenue stream allowed for organic, self-sustained progress.

Time Captured, Legacy Secured

With hard work and an unyielding commitment to his creation, FutureMe evolved from a side project into a thriving business that generated six figures in revenue annually. And when the acquisition offers started knocking, Matt's resolve remained steadfast.

He turned down tantalizing proposals, choosing organic growth and the insights of his vast user base over a quick sale.

Matt's patience and dedication paid off when he finally found the right match in Memories Group Limited, a company dedicated to preserving digital legacies. The acquisition culminated FutureMe's remarkable 20-year saga and opened new horizons for its future.

Lessons from the Future

Reflecting on his arduous but fulfilling entrepreneurial voyage, Matt's story underlines the inherent value of authenticity and resilience in business. His willingness to adapt, engage with a diverse audience, and maintain an affordable yet sustainable business model speaks volumes about the success of FutureMe.

Matt's remarkable tale is an inspiring case study for aspiring entrepreneurs and startups. From cultivated childhood ideas to lifelong lessons in patience and perseverance, Matt's story is an inspirational testament to the possibilities that can grow from the roots of early creativity.

Matt on helping the future generation - 

Matt is eager to support upcoming entrepreneurs working on side hustle projects that align with his experience with FutureMe.

He is particularly interested in helping those developing consumer products, as he believes it is possible to build a successful consumer indie business rather than focusing only on creating a dull B2B SaaS product.

Matt emphasizes the importance of simplicity, taking things slow and steady to avoid mistakes, and embracing a slightly unconventional approach. He plans to share more insights about these critical principles soon.

Mar 23, 2024
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