164: Matt Sly Podcast
An interview with the founder of FutureMe.
Earlier this year, Rob Greig and I released ttyl - a free tool for audio journaling. A few months later, Rob and I got connected with Matt Sly, the founder of FutureMe.org.
In this interview, Matt shares his two-decade journey founding and scaling FutureMe to millions of users, and becoming the OG tool for sending letters to your future self.
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[ 48 min watch ]We discuss creative side projects, good/bad luck, time capsules, early 1990s internet culture, design, tech cycles, new AI tools, battling cancer, and his life-changing exit.
Clickable chapter links via YouTube
00:46 - Early life, beginnings
04:10 - Early days of the 1990s internet
05:12 - FutureMe origin story
09:12 - Side project motivations
09:48 - Matt's personal use cases
14:20 - The original architecture
16:21 - Growth and marketing strategy
17:52 - Infrastructure during viral moments
20:40 - Security considerations
23:26 - From art project to business
26:22 - Considering VC investment
29:07 - Time to sell or raise money?
30:38 - Post-sale reflections
33:14 - What Matt's up to now
35:05 - Side projects in 2025
37:11 - Matt's battle with cancer
40:49 - Collaborating with others
42:00 - Reflecting on unconventional success
45:50 - The role of luck
47:06 - Get in touch w Matt
Curious?
Check out ttyl ⏳
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