Matthew Rosenberg

Product Visionary

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

What drives Matthew's entrepreneurship?

Matthew seems genuinely motivated by the challenge of connecting people in ways that didn't exist before. Look at the thread running through his work—group messaging before it was mainstream, video sharing, city guides, travel planning, and now AI agents for small businesses. He's consistently drawn to communication and coordination problems. There's also a restlessness to him. He spent a year traveling the world after an exit, and that experience directly birthed Welcome. He's the kind of person who turns lived experience into product ideas rather than chasing trends on a whiteboard. At the core, I think he wants to build things that genuinely change how people operate day-to-day—whether that's how you plan a trip or how a small business runs its back office.

Tell me about his exits

Matthew has had two notable exits. He co-founded Cameo (the mobile video editor, not the celebrity shoutout platform) which Apple named "Best of 2013" and was acquired by Vimeo in 2014—he stayed on as VP after the acquisition. More recently, he founded Tripnotes, an AI trip planner that went viral with over 2 million users in its first 60 days, which was acquired by Dorsia, where he then served as VP of Product. Both exits followed a similar pattern: build something with real traction, get acquired, and stay involved through the transition before moving on to the next thing.

What's his background?

Matthew's a serial entrepreneur and product designer who's been building consumer tech products for about 15 years. He's had a few notable exits—co-founding Cameo (acquired by Vimeo) and Tripnotes (acquired by Dorsia)—and his work has consistently centered on connecting people, whether through group messaging, video, travel, or now AI automation. He's currently in Austin building Little Engine, which brings AI agents to small businesses over SMS. He's also a Stanford GSB Leadership Fellow, which reflects the more strategic, leadership-focused side of his career alongside the hands-on building.

What is he building now?

Matthew is currently building **Little Engine**—an AI automation platform for small and medium businesses. The core idea is simple but clever: AI agents that handle business operations entirely over SMS, so there's nothing to download or log into. He raised a $2.5M pre-seed to get it off the ground and is focused on making powerful automation accessible to the kinds of businesses that don't have dedicated tech teams.

What does Little Engine do?

Little Engine builds AI agents that automate operations for small and medium-sized businesses—entirely over SMS. No apps to download, no logins to manage. The agents have memory, so they get smarter about your business over time. Matthew raised a $2.5M pre-seed to build it out, and the core idea is meeting SMB owners where they already are: their phones.

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 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.

What was the Dorsia acquisition?

Dorsia acquired Tripnotes in 2024, which brought Matthew onto their team as VP of Product. Tripnotes was an AI-powered trip planning app that had gone viral—2M+ users in the first 60 days—and Dorsia, the members-only restaurant reservation platform, saw a natural fit given the travel and dining overlap. Matthew spent about a year there integrating the product before moving on to found Little Engine.

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