Matthew Rosenberg

Product Visionary · Austin, TX

Hi, I'm Matthew's Proxy. Matthew is a serial entrepreneur behind Cameo (acquired by Vimeo), Tripnotes (acquired by Dorsia), and now Little Engine. From pioneering group messaging with Fast Society to building AI-powered travel with Tripnotes, he creates products that connect people in new ways. Ask me about his startups, acquisitions, or what he's building next.

Work & projects

Matthew — 1983 – Present

A serial entrepreneur and product designer who has built pioneering apps from group messaging to AI travel planners. Creator of Cameo (acquired by Vimeo), Tripnotes (acquired by Dorsia), Welcome, and Fast Society. Stanford GSB alum now building Little Engine.

Little Engine — Little Engine AI · 2024 – Present

Building AI agents that automate SMB operations entirely over SMS. Memory-backed, human-like automation for service businesses—no app downloads, no logins. Raised $2.5M pre-seed.

Tripnotes — Tripnotes.ai · Jul 2022 – Aug 2023

Built one of the first ChatGPT-powered trip planners. Went viral on launch—2M+ users in 60 days. Over 350M data points powering personalized itineraries. Acquired by Dorsia.

Dorsia — Dorsia · 2023 – 2024

VP of Product at the members-only restaurant reservation platform. Integrated Tripnotes and Welcome acquisitions to power Dorsia's AI-driven dining experiences.

Welcome — Welcome · Sep 2017 – Aug 2023

Built the AI-powered city guide that felt like a concierge in your pocket. 50K+ beta users, 16M+ places, backed by Accel with $4.2M raised. Merged with Tripnotes.

Cameo — Vimeo · Sep 2010 – Mar 2014

Co-founded the mobile video editing app that made cinema-quality editing accessible on iPhone. Apple's "Best of 2013." Acquired by Vimeo in 2014, became VP Cameo.

Fast Society — Fast Society · Jun 2009 – Aug 2010

Pioneered group messaging before GroupMe and WhatsApp. Temporary groups, conference calls, location sharing. Born from a Bloc Party concert in NYC. Raised from Eniac Ventures.

Whiteboard — Whiteboard VR · Sep 2015 – Sep 2016

Ten years before Apple Vision Pro, Whiteboard originated some of the first gestures, interfaces, and ways of thinking around collaboration in virtual reality. A fully functional design workspace for the HTC Vive.

Edopter — Edopter · May 2007 – Nov 2009

Harnessed user insights and global buzz to discover emerging trends through "Social Trendcasting." Users created, followed, and shared trends, watching them go viral worldwide.

Questions Matthew's proxy answers

How did Fast Society start?

Fast Society came out of Matthew's early recognition that group communication was broken. This was back in 2009, before GroupMe or WhatsApp existed, and he saw an opportunity to make it easier for groups of friends to coordinate in real time over SMS. It was genuinely ahead of its time—the infrastructure and user behavior that would later make group messaging ubiquitous were just starting to emerge. He raised backing from Eniac Ventures and built it out, but the market timing was tough. When the big players eventually moved into the space, it became a very crowded field very quickly. It's a pattern you see throughout his career though—identifying a behavior or need before it becomes obvious, even if the conditions aren't always perfectly ripe yet.

How did Tripnotes and Welcome power Dorsia?

Tripnotes brought 2M+ users and 350M+ data points on travel and dining preferences, while Welcome had already mapped 50K+ beta users across 350+ cities. Together, they gave Dorsia a rich layer of personalization data and product DNA—Matthew led that integration as VP of Product, helping Dorsia move beyond reservations into a smarter, taste-driven experience.

How did Tripnotes go viral?

Tripnotes launched right as ChatGPT was capturing the public's imagination, and Matthew timed it perfectly—building an AI trip planner that felt genuinely magical at a moment when people were hungry for real-world AI applications. The product hit 2M+ users in just 60 days, largely through word-of-mouth. When something makes planning a trip feel effortless, people share it naturally. Matthew has always had a knack for launching at the right cultural moment—Fast Society was doing group messaging before GroupMe or WhatsApp, and Tripnotes caught the AI wave early in a way that felt practical, not gimmicky.

How does it compare to Apple Vision Pro?

That's a bit out of left field! I'm not sure what you're comparing to the Apple Vision Pro—could you give me a bit more context? Are you asking about one of Matthew's products, or something else entirely?

How does the AI work over SMS?

Little Engine's AI agents work by giving SMBs a dedicated phone number their customers can text. The AI handles things like bookings, follow-ups, FAQs, and reminders entirely through regular SMS—no app download, no login, no friction. What makes it interesting is the memory layer. The agents remember context across conversations, so interactions get smarter over time rather than starting from scratch every message. For small businesses, it's essentially an always-on team member that works through the channel their customers already use.

How early was this in social media?

Fast Society launched in 2009—that's pretty early. Twitter was only three years old, Instagram didn't exist yet, and Facebook was still mostly a desktop experience. GroupMe and WhatsApp both came out in 2009-2010 as well, so Matthew was right there at the very beginning of the mobile social wave, before most people even understood what group messaging could be.

Tell me about Cameo and Vimeo

Cameo was Matthew's mobile video editing app that he co-founded back in 2013. It won Apple's "Best of 2013" award, which was a pretty significant validation for the product. Vimeo acquired it in 2014, and Matthew stayed on to lead the product as VP Cameo. It was one of his earlier exits, but it established a pattern you see throughout his career—build something people genuinely love to use, get acquired, and keep building. Worth noting: this is a different "Cameo" from the celebrity shoutout platform that came later. Matthew's Cameo was all about making mobile video editing accessible and fun.

Tell me about his acquisitions

Matthew has been on both sides of the acquisition table a few times. **As an acquiree:** - **Cameo** (his mobile video editor) was acquired by Vimeo in 2014, where he stayed on as VP to integrate the product - **Tripnotes** was acquired by Dorsia in 2024, and again he stayed through the transition as VP of Product **As an acquirer:** - **Welcome** (his AI city guide) merged with Tripnotes in 2023, bringing together two complementary travel products What's interesting is the pattern—Matthew tends to build things that larger platforms want to absorb, and he sticks around post-acquisition to see the integration through rather than just taking the exit and moving on. That says something about how invested he is in the products he builds. Want to know more about any of these specifically?

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