The contrarian who runs toward the red tape.
Founder · CEO · Investor
Justin
Wenig
He sold one company for nine figures, then walked straight back into the market every other founder swears off: selling to the government.
He sold one company for nine figures, then walked straight back into the market every other founder swears off: selling to the government.
Most founders treat government sales the way swimmers treat jellyfish. Wenig went looking for the swarm. The bureaucracy everyone fears, he reads as a moat.
In October 2025, Starbridge closed a $42 million Series A led by Craft Ventures. The check arrived for a company doing the unglamorous thing: helping businesses find and win contracts inside the roughly $2 trillion that U.S. state, local, and education agencies spend every year. That budget is enormous and almost nobody chases it well, because the buying signals are buried in PDFs, agency websites, meeting minutes, and directories that go stale the week they're published.
Justin Wenig knows that maze by hand. At his last company he spent hours combing through hundreds of pages of school-board minutes and filing Freedom of Information Act requests just to learn which districts might be ready to buy. Starbridge is the product he wished existed back then - software that reads the public record at machine speed and tells a sales team where to focus and when to act.
The pitch is deceptively plain. Watch every public agency, rank accounts by how ready they are to buy, flag the leadership changes and new projects that precede a purchase, then surface the contract before the request-for-proposal is even written. By early 2025 more than 160 enterprise sales teams were using it, names like Instructure, Clever, and SimpliGov among them.
What makes the bet interesting isn't the AI. It's the choice of battlefield. Government sales are slow, relationship-heavy, and allergic to scale - which is exactly why incumbents avoid them and why, once you're in, you're hard to dislodge. Wenig has spent his whole career in that gap.
Instead of chasing noise, our customers have a clear view of where to focus and when to act.
- Justin Wenig, on what Starbridge actually sells"The most pressing challenges of our time can only be solved through bold collaboration between innovative businesses and visionary government."
- The thesis on his personal siteIn 2019 Wenig went through Y Combinator with Coursedog, a platform that modernized the operational guts of universities and public agencies - the scheduling, the curriculum, the unglamorous machinery that keeps an institution running. He's described the scene plainly: "Among hundreds of startups, there were just a few of us trying to bring modernization to the interplay between government and education."
Investors warned him off. Public-sector sales were slow and didn't scale; smart money went elsewhere. He kept going. Coursedog reached more than 300 institutions, and in 2021 he sold it to JMI Equity for a nine-figure sum and stayed on the board. The same year, Forbes put him on its 30 Under 30 list.
The exit could have been an off-ramp. Instead it was research. Every painful FOIA request, every page of minutes he'd read by hand, became the spec sheet for what came next.
Co-founds a higher-ed and public-sector operations platform - the corner of the market other founders skip.
Sells Coursedog to JMI Equity, stays on the board, lands on the Forbes list.
Builds the AI tool he wished he'd had at Coursedog: find, engage, and win public-sector contracts.
Craft Ventures leads, with YC's Michael Seibel and OpenGov's Zac Bookman joining. Total raised hits $52M.
He didn't study the public-sector problem. He bled it at Coursedog, FOIA request by FOIA request.
A nine-figure sale to JMI Equity is the kind of receipt that shortens a fundraising conversation.
Craft Ventures credited his "rare insight and intensity" for the job of cracking public data open.
What once took hours of manual research by an account executive now happens in seconds. From there, insight turns into action.
- Justin Wenig, on the Series ABetween board meetings, Wenig runs a busy side ledger. He's an active seed investor in more than 50 early-stage AI companies, and reportedly the second-largest seed backer of the chip startup Etched. The roster runs wide - Span, Juicebox, Finny AI, Henry AI, Anthrogen, Parallel, Vitalize Care - a spread that looks less like a thesis and more like a founder who can't stop betting on other builders.
Then there's the part that has nothing to do with software. He created The Watermill Cup, a summer games experience for adults out on Long Island - a homemade Olympics for grown-ups. It's the kind of detail that explains the rest: a person who, faced with something that doesn't exist yet, simply makes it.
A short on Justin Wenig and the Starbridge mission.
Wenig on EdTech Insiders, unpacking how to actually sell into schools and agencies.
A featured speaker on AI and the future of public-sector and education markets.