In 2022, Brian Raymond raised the first $5 million for his startup company Unstructured by using a PowerPoint pitch deck.
It was the summer of 2022, and it was one of the worst times to be raising investor money. There were fears of a pending recession and interest rates were climbing and venture capital investors had been seriously retrenching since the record VC investment year of 2021.
His pitch outlined a problem facing the use of large language models like ChatGPT in accessing myriad file types to make curated information accessible and useful to customers.
Unstructured software makes it easier for customers to access data no matter the file type, document location or layout, so that the user can better use artificial intelligence in a meaningful way for their purposes.
The company raised $25 million in its first full round of funding in July 2023, and then it raised an additional $40 million in March, bringing it to $65 million raised.
The company is still fully remote, which is working out well because 45 of its 50 employees are engineers and they are not reticent to use technology, Raymond said.
“When I received the first investment, I had never met them in person,” Raymond said. It was all video conferences.
Unstructured makes an open-source solution which has been downloaded 10 million times, and its commercial application is used by 45,000 paying customers. At the end of last year, many customers were U.S. government agencies. That mix has changed since then to mostly private industry, many of them in the Fortune 500, Raymond said.
Unstructured charges commercial customers by file accessed. Raymond said its annual revenue is in the high seven figures.
Raymond started Unstructured two years ago after working for three years as a vice president at PrimerAI, a San Francisco-based company specialized in AI-powered data analysis. That company was focused on building custom applications for customers.
While working there, Raymond noticed that a key problem was making artificial intelligence large language models able to get access to information in different file types.
The vast majority of enterprise data lives on formats like HTML, PDF, PNG, CSV, texts and even video, and those formats are difficult to access by large language models like ChatGPT-4 without manually transferring the data. That’s a big problem, because large companies can produce a quarter million new files a day, he said.
Unstructured’s software also allows AI platforms to precisely choose data, including their own internal documents.
To make its customers’ data more useful, Unstructured curates the files so that meaningful files are accessed while random unusable data is not used for the customers' purposes.
“It is rare in venture investing to find a founder who possesses a clarity of vision, deep technical insights and a commercial instinct, but Brian is that rare breed of founder with all these qualities,” said Karan Mehandru, managing director of Seattle-based venture capital firm Madrona Ventures, in an emailed statement. “We were impressed when we first invested last summer, and our level of conviction in the company and Brian has only grown in recent months as we watched customers clamoring for the product.”
Other Unstructured investors include Bain Capital Ventures, M12 (formerly Microsoft Ventures), Mango Capital, MongoDB Ventures, Shield Capital, IBM Ventures, Sacramento Kings Chairman Vivek Ranadivé, New Normal Fund and NVentures, Nvidia Corp.’s (Nasdaq: NVDA) venture capital arm.
Raymond grew up in Roseville. He was an avid motocross racer and dirt bike rider, and had a few broken bones when he was younger. Nowadays, with a wife, three kids and two dogs, and being CEO of a startup company, he leaves the dirt bike in the garage. He still rides, however. He has a Ducati road bike he rides occasionally in the foothills to unwind.
Raymond attended Sierra College before going off to get two degrees at the University of California Davis. At UC Davis, he was recruited into the Career Analyst Program with the CIA, where he worked for five years, including two tours in Iraq, before working on the National Security Council for a year in President Barack Obama's second term.
On the first night of Raymond's first tour in Iraq, his station was shelled. “I slept under by bed with body armor over my head," he said. "Welcome to Iraq.”
He jokes that his career path from the CIA to the White House to investment banking and then to technology appears “nonlinear.” But he said that it's not unusual for people in national security to go into investment banking. “The tools are similar," he said.
During the time he was at the investment bank, he went to a reunion lunch in the Bay Area with some former CIA colleagues, and nearly all of them were working in technology companies and were interested in artificial intelligence.
When he started working at an AI company, he discovered a difficulty for the industry was getting vast data into formats that are usable.
“It was a problem that needed a solution. We started working on the problem and built a team to focus on the problem space,” he said.
The Essentials
Brian S. Raymond
Founder and CEO of Unstructured.io
Age: 38
Education: Bachelor’s and master’s degrees in political science from the University of California Davis; CIA’s Sherman Kent School for Intelligence Analysis; MBA from the Tuck School of Business at Dartmouth College.
Career: Intelligence officer, CIA, 2009-2014; White House National Security Council, director for Iraq, 2015; investment banking, Harris Williams & Co., 2016-2018; vice president at Primer.ai, 2018-2022; founder Unstructured.io, 2022-present.
Personal/family: Married with three kids, ages 6, 3 and 2. Lives in Rocklin.
Something people would be surprised to know: His writing has been published in magazines, including Foreign Policy and Dirt Rider. And he has written for a sitting president, Barack Obama.
Passion (outside of work and family): Motorcycles, spy novels
First job – nonprofessional: Working in motorcycle shops
