"Somehow Amazon and Google positioned themselves as the open source-friendly companies, which seems to be the opposite of reality."Rowan Trollope — CEO, Redis
From WarGames to Billion-Dollar Companies
Trollope grew up in Hollywood, surrounded by artists. His father gave him a Texas Instruments computer. He borrowed a Commodore 64 at Radio Shack. He watched WarGames and tried to build the AI bots the movie described - on a machine with 64 kilobytes of RAM. By 15, he had his first professional programming job in a data processing center.
None of that is surprising in isolation. What is unusual is that the technical curiosity never got displaced by the executive career. He still writes code. He still reads commits. He is the kind of CEO who, when transitioning to a new company leading a data platform, actually uses the data platform for something real before deciding what to do with it.
He also, separately, was a break dancer. And in his late 20s, he painted - seriously enough to host his own gallery show. A mountain climber who survived a failed anchor at 20 hours into an Eastern Sierra ascent. He describes himself as a "renaissance man." The self-description is irritating in lesser hands. With Trollope, the resume makes it plausible.
"I became more focused on doing things right and paying attention to every little detail."
That near-death experience on the mountain reshaped him. Not as metaphor - he talks about it practically: he had installed a backup anchor despite exhaustion, because something instinctive told him to. The backup saved his life. The lesson migrated directly into his management philosophy: redundancy, thoroughness, attention to the detail everyone else skips when they are tired.
At Symantec, Trollope was Group President of the SMB and SaaS business. At Cisco - which he joined in 2012 - he ran the Collaboration Technology Group, overseeing a sprawling portfolio: WebEx Teams (the product that would eventually become the foundation of Cisco's pandemic pivot), TelePresence, UC Manager, and the Unified Contact Center. These were not niche products. They were the communication infrastructure for Fortune 500 companies, rebuilt for a cloud-first world.
His pivot from Cisco - a $200B company - to Five9, a cloud contact-center software company with a fraction of the resources, raised eyebrows. He did not blink. He quadrupled Five9's revenue over four and a half years. He pushed the market cap past $5.4 billion. In 2021, Zoom tried to acquire Five9 for $14.7 billion. The deal collapsed when Five9 shareholders balked. Trollope resigned in October 2022.
At Five9, he built the company into a billion-dollar business - quadrupling revenue while expanding profitability, and steering a near-$15 billion acquisition attempt from Zoom that ultimately fell apart at shareholder vote.
The months between Five9 and Redis were not idle. He was reverse-engineering Redis - literally. Building with it. Understanding why developers loved it in a way that could not be absorbed from a pitch deck or an analyst report. "I understand why it's one of the most successful and one of the most loved products in the world," he would say later. "It's so easy to use, it's so simple."
Making the Fastest Database Even More Essential
The License Pivot
Trollope moved Redis to dual source-available licenses in 2024, preventing hyperscalers from monetizing Redis innovations without contributing. His verdict: "We've had record growth since we switched the license."
LangCache
Redis's fully managed semantic caching layer for LLMs. Cache hits deliver 15x faster response times and cut LLM API costs by up to 70%. Launched 2025. Trollope's clearest statement yet that Redis is AI infrastructure, not just a database.
Decodable Acquisition
September 2025: Redis acquires real-time data platform Decodable to strengthen its data pipeline capabilities. Trollope: "the context and memory that intelligent agents depend on."
Trollope's Redis thesis is straightforward: AI applications need context. Context requires data. Data needs to be fast. Redis is already the world's fastest data platform. The step from "developer caching tool" to "AI agent memory layer" is not a pivot - it is an upgrade.
But the path required hard choices. The licensing change - moving away from the open-source BSD license for advanced features including Redis Search, RedisJSON, and the vector database modules - was the most controversial. It alienated some open-source purists. It triggered a community fork. Trollope shrugged off both. He had heard the arguments before: that the change would drive developers away, that the brand would suffer, that the community would splinter.
"You have to have the arrogance to say: 'Thanks for your opinions. I disagree.'"
The metrics sided with him. Redis reported record growth following the license change. The company began positioning itself for an IPO - not under pressure, but on its own timeline. "My intent is to IPO the company," Trollope has said. "That's very much in the cards." He is in no rush. The balance sheet is healthy. The AI tailwind is real. The developer brand is intact.
His team assembly reflects the contrarian hiring philosophy he has made explicit: "Don't hire people that look and operate like you." The Redis leadership team he built - CTO Benjamin Renaud, CRO Spencer Tuttle, CMO Keith Messick, CCO Tom Rabaut, CFO Tony Tiscornia, CAO Diane Honda - is deliberately not a mirror image of Trollope. He seeks candidates who are "slightly rebellious" and who "question everything." The hires he was most uncertain about, he says, became his best performers.
"As AI enters its next phase, the challenge isn't proving what language models can do; it's giving them the context and memory to act with relevance and reliability."Rowan Trollope — Redis Released 2025
30 Years in One Line
Things That Don't Make the Bio
Break Dancer
As a teenager growing up in Hollywood surrounded by artists, Trollope was a break dancer. The same kid building AI bots on a Commodore 64 was also spinning on the floor.
Painter
In his late 20s, Trollope pursued painting seriously enough to host his own art gallery show. He has written a blog covering both his artistic and mountaineering pursuits.
Mountain Climber - Almost Didn't Make It
During a 20-hour Eastern Sierra climb, his primary anchor failed. He survived because, despite exhaustion, he had installed a backup anchor. The experience reshaped how he thinks about thoroughness.
Commodore 64 Graduate
Trollope taught himself to code at age 11 using equipment at a Radio Shack, inspired by the 1983 film WarGames. His father had given him a Texas Instruments TI-99/4A. Radio Shack had the Commodore 64.
Patent Holder
Holds multiple patents in computer security and operating systems. US Patent 9,946,852 B2 (issued 2018) covers a commodity hardware-based parental control device using a USB-like key - filed in 2009.
The Zoom Deal That Wasn't
While Trollope was Five9 CEO, Zoom offered to acquire the company for ~$14.7 billion. Five9 shareholders voted it down. The number still sits on the record as one of the largest terminated tech acquisitions of 2021.
On Record
"Don't hire people that look and operate like you."
"Redis has established such a strong brand, it's clear we're poised for a podium spot."
"We're on a level playing field now; we get to compete on product."
"There weren't any questions in my mind that this was the right call."
"If you're willing to put in the time and effort, anything can happen."
"It is not the mountains we conquer but ourselves."
The Bet He's Making
The Redis IPO is coming. Trollope has said it plainly. The company is well-funded ($357M total raised, last round at $110M Series G in April 2021), and the market conditions matter more than urgency. There is no distress driving the timeline. Redis can wait for the window it wants.
The larger bet is architectural. Trollope believes the generative AI era needs a different kind of data infrastructure: one that is fast enough to feed AI agents in real-time, flexible enough to handle vectors alongside traditional data structures, and reliable enough to serve as memory for systems that cannot afford to re-query a database every time they need context. Redis, he argues, is already most of that. LangCache and Decodable fill in the rest.
He is not wrong that the timing is good. Every company building on LLMs is wrestling with latency, cost, and context. The companies that solve those problems at the infrastructure level - not the application level - tend to become dependencies. Dependencies become categories. Categories produce IPOs.
Trollope's aspiration: transform Redis from the world's most loved caching database into the essential data and memory layer for the AI era - positioning it alongside MongoDB, Snowflake, and Databricks as enterprise data infrastructure that developers chose first, and CFOs followed later.
The man who taught himself to code on a Commodore 64 while reimagining what a fictional teenage hacker could do is now running a company that may become foundational to how AI agents remember what they know. There is a continuity there that is not accidental.