Michael Pryor ’98, Trello CEO + Co-Founder, talks with Dartmouth students
On Valentine’s Day, Michael Pryor ’98, CEO and Co-Founder of NYC-based Trello, stopped by the DartmouthWest office for a live Q&A with Dartmouth students back in the DALI Lab (Digital Arts, Leadership & Innovation) in Hanover.
Michael was in town to tell the Trello story at the SaaSTr Annual Conference, and you can find a quick recap of his talk here from Diego Gomes. Trello was acquired by Atlassian early this year.
Though he admits he doesn’t have the chance to code as much as he’d like to anymore, Michael has come a long way since creating Dartmouth’s first electronic voting system for student elections, or crashing Blitzmail while trying to run a script that would collect — and then email to every student — information about all the parties on campus.
Despite his orientation toward independent technology projects and his CS degree, he did feel some pressure to move forward on a traditional trajectory, and joined an investment firm after graduation. The firm had some technology investments, which inspired him to jump fully into the tech sector at early internet service provider Juno during the first dotcom boom.
Seeing his stock options eventually fizzle out as the boom became the bust inspired Michael to recalibrate his thinking around work. He embraced the freedom many recent grads have early in their careers to explore different paths, to take risks, and to optimize for the career experiences that inspired him intellectually.
“The real question is what do you want to do? Where do you want to make a difference?” -Michael Pryor
Fully leveraging his CS degree, he and Joel Spolsky co-founded Fog Creek Software with two key missions: to provide developers with a great place to work, and to build quality products. Over the last 16 years, the Fog Creek team built a number of products before Trello, primarily tools for developers. Successful products brought the firm profits that were distributed to employees, and both hits and misses offered lessons on growth, market development, strategy, and management.
One of its earliest products, FogBugz, was successful enough to provide working capital while other projects like Copilot, and eventually Stack Exchange and Trello, were developed.
When Trello was in its early days, the lessons learned from these projects were pivotal in the decisions made about Trello’s future. One key strategy: profits from the Trello product were reinvested into the product and employees’ equity value grew. Trello’s rapid growth validated this leap of faith and the departure from the company’s previous norm of profit-sharing.
Another key decision was to orient Trello to a much bigger market opportunity — the process management market, vs. the project management market, a subtle difference that made Trello a much more flexible and adaptable tool that could be used by anyone from software teams to little league teams. The Dartmouth West team, in fact relies on Trello for at least 3 different use cases with very different setups — event planning, team workflow, and project management.
After launching Trello in 2011, Fog Creek spent several million dollars in internal development and then spun out the product as an independent company with Michael as CEO, raising $10 million in outside capital to help the company scale. Late last year, Trello announced they’d surpassed 17 million users.
It was a conversation with Atlassian’s Mike Cannon-Brookes over coffee in NYC that started Trello down the track to a $425 million acquisition. One of Michael’s goals was to drive Trello to 100 million users — a goal they shared with Atlassian — and after hearing about Atlassian’s vision for its product suite, he asked himself, “Can I get to 100 million users faster by myself or together with Atlasssian?”
Reflecting on the choice to build a company in New York in response to a student’s question, Michael agreed that there are tradeoffs. He loves that the tech industry isn’t as ubiquitous in NYC as it is in Silicon Valley, leaving room for a lot more in NYC’s urban culture, but concedes that the access to capital and talent is tighter. As a result, Michael and his co-founders grew their products with a strong revenue orientation, and built a team that is 60% remote.
Michael attributes part of his success to luck (having the right product at the right time) and privilege (the ability to come to Dartmouth in the first place and the freedom to take some early entrepreneurial risk), but also abides by three very simple rules as CEO: don’t run out of money, keep to the vision you outline for your product or company, and recruit top talent for your team.
Before returning to Atlassian’s SF office to continue integrating their teams, Michael left the students with a thought about finding an idea to pursue, telling them “You have to believe in the way the world will work a few years down the road — and maybe be the only person who believes that.” It’s fitting that Michael stopped by on Valentine’s Day. Entrepreneurship, like love, might be the biggest leap of faith we can take.
Have an idea about other Dartmouth alumni whose stories we should share? Feel free to drop us a line or suggest them in the comments.
