SAN FRANCISCO and SEATTLE—Galvanize, a meeting place for emerging tech startups in San Francisco, isn’t the type of place one would expect to find the head of the Pentagon and his posse of business-suited officials. The hipster chic campus is populated with young, multicultural entrepreneurs, who sip coffee brewed by an in-house barista while working on their laptops at butcher’s block tables.

Yet on March 1, that’s where Defense Secretary Ashton Carter met with five business leaders eager to pitch their ideas in a “Shark Tank”-like scenario where companies were given 10 minutes to make their case to the secretary and Pentagon top weapons buyer Frank Kendall. The event was the brainchild of Carter’s Defense Innovation Unit Experimental (DIUx), the outpost he set up in 2015 to engage with Silicon Valley companies that have created groundbreaking technologies that might be the answer to some the Pentagon’s most pressing problems.

Reporters—including sister publication Defense Daily, which traveled with Carter during his West Coast trip the week of Feb. 29—were allowed to watch the first pitch for a technology called Bromium, a software created to protect computers, networks and applications against zero day attacks by isolating computational tasks that originate from an unknown source. He also heard pitches from other businesses such as Saildrone, which offers small unmanned sailboats capable of collecting and transmitting information, and Quid, a big data analytics company based in San Francisco.

Throughout Bromium’s pitch, Carter peppered Sherban Naum, regional vice president for the company’s federal business, with pointed questions about the product’s competitors and limitations.

“I’m asking myself why wasn’t this thought up earlier, let me put it that way,” Carter said, interrupting Naum’s speech. “What happens if it’s not something bad and you actually want to use it, and you do want it to talk to the rest of your system?”

Carter has made repairing the Pentagon’s frayed relationship between Silicon Valley a cornerstone of his tenure. His trip to the technology hub last April, when he announced the formation of DIUx, ended a 20-year standstill during which no defense secretary had visited the region. The Feb. 29 week marked Carter’s third visit in less than a year’s time.

Since DIUx kicked off operations last August, its 21-person staff have met with “hundreds” of companies in the region, according to the department. The unit has created pilot programs with cloud computing company Salesforce [CRM] and software firm Huddle, among others. It also interfaces with other parts of the department such as U.S. Cyber Command in order to determine when emerging technologies could fit an existing requirement.

After the pitch, Naum was emphatic that having an office like DIUx in the region is necessary for making a real, tangible impact in Silicon Valley. “This should have been done a long time ago,” he told reporters.

Bromium has been in contact with the outpost for about four months, and since then has had weekly conversations with department officials.

“They’re actually helping us identify who could use this technology, so it is a very interactive thing. It’s very cool. It’s very un-governmental. You’d expect this to be big bureaucracy. This is nimble, it’s agile, and they actually do care,” he said.

“There are already conversations about what’s next,” he added, though he declined to comment on potential outcomes the department is considering.  “Hopefully this will accelerate all of that.”

DIUx will work not only to connect companies with the right parts of the department, but also could connect commercial industry to defense contractors that already work regularly with the military, Carter said.

“Introducing our problems to these bright people, that’s what it’s all about,” he told reporters after the Shark Tank event. “I could do this all day…It’s endlessly fascinating.”

Over the course of the week, Carter added to the list of initiatives he’s established to try to court commercial tech businesses and startups. On March 2, he formed a new innovation advisory board to be chaired by Google [GOOG] parent company Alphabet exec Eric Schmidt and announced a “bug bounty” program that will allow vetted coders to try to hack selected Pentagon websites. He addressed the RSA security conference in San Francisco, where he pressed young scientists and technologists to spend a year working for the Defense Department.

“If you don’t take risk, and you’re not willing to fail, then you’re never going to get anywhere. And you all know that and that’s one of the things that’s imbued in the innovative community out here,” Carter said at RSA. “We have to try to imbue our own folks with the same kind of spirit. Go out there and try something new. We can’t just keep doing what we’re doing because the world changes too fast. Our competitors change too fast. So it’s a serious matter for us to remain open. And government does tend to be closed. The defense establishment especially just tends to be closed.”

In Washington, D.C., a defense secretary keynote speech practically guarantees a packed house, but the middling attendance at RSA proved Carter is less of a draw in Silicon Valley–although a staff member noted that after the speech, audience members crowded around to offer business cards.

DIUx and other outreach efforts are changing the relationship between the Defense Department and the technology sector, said DJ Patil, the chief data scientist at White House Office of Science and Technology Policy.

“The number one thing I’ve found as a Silicon Valley person is everybody wants to figure out how to help. They struggle to figure out how do you actually do it,” he said following Carter’s rollout of the bug bounty program. “What they’re realizing now is, oh, through DIUx, through all of these other mechanisms.”

In Seattle, Carter swung by Microsoft’s [MSFT] campus, where he toured its digital cybercrimes unit. Later that day, he met with Amazon [AMZN] CEO Jeff Bezos and received a briefing on the company’s cloud computing technologies.

The Defense Department has been slow to adopt some of Amazon’s computing products compared to civilian government agencies like the Department of Health and Human Services or even the intelligence community, which has procured its own secure cloud “region” that is owned and operated by the company, said Mark Ryland, Amazon’s chief solutions architect for worldwide public sector. However, efforts such as DIUx and Carter’s continued outreach to the commercial sector have boosted confidence that things are changing.

“I would say DoD is definitely lagging, but we’re very hopeful. The secretary of defense seems like a very forward looking guy who is making some good things happen. Even just this week seems like a real breath of fresh air,” Ryland said March 3. “We’re seeing the advent of things like his move to bring the digital services into DoD. That could be highly impactful.”

Other industry executives reiterated that many of the obstacles separating the department from commercial businesses are cultural in nature. For instance, Bromium doesn’t need regulatory changes to defense acquisition policy to sell to the government, Naum said. However, the process itself can be more onerous simply because of the nature of the Defense Department and the risks involved with its missions.

“The challenge that the government is facing is they can’t allow anything to get in the way of the mission, so they have to vet technologies, they have to evaluate them,” he said. “We’re going through those processes. Is it harder just because it’s the federal government? Absolutely.”