Charles Teague had a perfectly reasonable objection to the iPhone. It had no keyboard. He was working at Microsoft, knew his way around software, and thought a device built around touching a screen sounded dreadful. Then somebody put one in his hands. His objections did not survive the demonstration. Before long, neither did his plan to stay at Microsoft.
That reversal is a useful place to meet him. Teague is the co-founder and former CEO of Lose It!, a former ColdFusion engineering leader, and now the CEO of Meridian Labs. The titles suggest a career conducted in conference rooms. His writing keeps returning to the workbench: a slow build, an awkward editor, a small extension that saves a little trouble. He seems most legible with a tool in front of him.
The telephone was the way in
His first opening in technology involved an actual telephone. Teague graduated from Macalester College in St. Paul with a political science degree. He had bought his first computer at nine, but had not chosen computer science. Asked about that decision years later, he recalled that the possibility simply had not occurred to him. A long acquaintance with computers had somehow failed to become an academic plan.
J.J. Allaire needed someone to answer his phones. Teague took the job at $12 an hour, passing on graduate school. He became Allaire Corporation’s first employee and moved through successive responsibilities until he was helping lead the product behind ColdFusion. The distance between answering a call and directing software development is considerable. He covered it inside the same growing organization, finding more consequential work as he went.
Allaire was acquired by Macromedia in 2001. Teague’s responsibilities there included engineering for ColdFusion. The early partnership also lasted beyond that company: he and Allaire went on to co-found Onfolio. Their working relationship would reappear across several chapters of his career. The person who first needed someone on the phones kept finding reasons to build with him.
A better way to keep what you found
Onfolio addressed a familiar indignity of online research: finding something useful and then losing it. Its tools let people collect web material, organize it, and add notes. Microsoft announced the acquisition of Onfolio’s assets in March 2006, incorporating its technology into the Windows Live Toolbar. The acquisition brought a small company’s work into a much larger software operation.
For Teague, Microsoft also fulfilled an ambition. In his later account of leaving, he described working there as a career objective he could now check off. His work included Windows Live Writer, the blog editor that let writers see a page as they composed it. An awkward publishing process could become something closer to using a word processor. That was a problem worth spending time on.
The appeal of the iPhone eventually sent him elsewhere. By September 2008, he had returned with his family to the Boston area and become a Technologist in Residence at General Catalyst. He had lived and worked around Boston for a decade before Microsoft. Coming back felt good. He even noted the timing: the baseball playoffs were approaching. A professional transition could accommodate a sporting calendar.
Counting the shop before opening one
Teague’s mobile curiosity left a trail of spreadsheets. In November 2008, he gathered data across the App Store because the analysis he could find concentrated on popular applications. That bothered him. Studying only the winners would give him a distorted picture of the marketplace. He wanted to see the shelves behind the shop window.
He counted more than 9,000 applications, examined prices, and compared the prevalence of free and paid software. The findings came with uncertainty. He could see people trying to sell expensive applications; he could not establish whether those efforts were working. He also admitted using .NET to collect the data rather than a more fashionable scripting language. The spreadsheet arrived without an outfit change.
Lose It! began in 2008 with Teague, Allaire, and Paul Dicristina. The business eventually provided a much longer lesson in building for a new platform. At General Catalyst, Teague had been studying what mobile companies might become. Now he was responsible for helping one operate. The questions moved from what the marketplace looked like to what a company could sustain.
His experience as a founder also makes an old MacBook Pro post amusing. After switching to a Mac in 2008, he kept Zune software and Windows Live Writer running through virtualization. He liked the new computer; he still wanted those Windows applications. The brown Zune beside the attractive laptop struck him as suitably ridiculous. A preference for useful software could survive a change of allegiance.
Making room in the CEO’s chair
By June 2020, Teague was ready to change his relationship with Lose It!. Patrick Wetherille, who had joined in 2012 and served as vice president of growth, became CEO. Eric Puidokas moved from engineering leadership to president. Teague became executive chairman. The succession came from people who already knew the business, rather than a new cast arriving at the door.
The handover announcement included a revealing measure of the company: five years of positive cash flow. Teague described creating room for Wetherille to lead. In July 2022, Ziff Davis announced that it had acquired Lose It! during the second quarter. Those dates give the company story a clear sequence: a founder’s operating tenure, an internal succession, and an eventual acquisition.
There was another thread already developing. In February 2022, Teague wrote that he had spent the previous 18 months at RStudio working on Quarto. After running a consumer company, he was again building publishing tools. The software even powered the personal blog on which he announced his return to writing. The workshop had become its own demonstration.
“I love products, I love working on technology, I love building things.”
Charles Teague, January 2019
The green checkmark missed something
Quarto supports scientific and technical publishing. Its ambitions include making documents easier to create, share, and reproduce. Teague’s February 2022 engineering post approached the project from a less ceremonial angle. Some automated tasks were getting slower. They were still completing, so a simple success indicator did not expose the problem. A passing build could be taking an unreasonable amount of time.
He assembled a way to track those durations using Amplitude and GitHub Actions, then added rendering performance checks. The purpose was to spot changes and investigate them. He explicitly acknowledged the limits of the measurements. For someone whose current work involves evaluation, this earlier account offers an interesting continuity: decide what to observe, collect it, and resist pretending the result says more than it does.
He kept making smaller conveniences too. In November 2023, he published two Quarto extensions to generate placeholder text and images. Testing documents repeatedly meant fetching sample material repeatedly. He preferred to automate the nuisance. The image extension brought an additional pleasure: it could surprise him with an agreeable picture. Engineering left room for the occasional cat.
In January 2024, another extension let writers embed social posts in Quarto documents with a shortcode. It supported several platforms and included fallback output formats. He invited requests for improvements. The announcement was brief, with a working example and installation instructions: enough to let somebody else try the thing.
713 fixes, with the caveat attached
When Quarto 1.4 arrived in January 2024, Teague measured the release in days and closed issues. It had taken 273 days and closed 713 issues, a longer cycle than usual. His table made the pace visible. He also doubted the team would sustain its recent rate of closing issues. A celebratory post could still include an honest reservation.
His taste in prose is equally direct. In March 2022, he singled out Cormac McCarthy as a favorite author and welcomed the novelist’s advice on scientific writing. He admired short, spare sentences. Beside the software posts, the preference makes sense: language, like an interface, can make somebody do unnecessary work. It can also get out of the way.
The personal details are modest. In 2017, Teague described time away from work spent cheering at his children’s hockey matches and swim meets. He called being a father the coolest experience. Alongside a career of platforms and products, there were seats beside a rink and a pool. A working life can have several audiences, some much less interested in the release notes.
Back with Allaire, asking new questions
In 2025, Teague co-founded Meridian Labs with Allaire and Eric Patey. He now serves as CEO. Before Meridian, he had been a Technology and Security Policy Fellow at RAND, helping develop Inspect AI. The nonprofit builds open-source tools for testing and understanding AI models and agents, with work shared across research and government organizations.
Inspect AI provides the machinery for running evaluations and examining their results. In May 2026, Teague also co-authored the announcement of Petri 3.0, an auditing tool whose development had moved to Meridian. The update separated components so researchers could customize them more easily. Even here, the practical question concerned what someone else would need to build on the work.
The career keeps changing scale: a telephone, a publishing editor, a mobile company, a research framework. Teague has repeatedly moved toward things he wanted to understand by working on them. The old iPhone episode retains its charm because the verdict changed after contact with the object. There is something reassuring about a software career in which trying the software still counts.