Active Duty at Insight

What did you learn from your experience as a Defense Ventures Fellow at Insight Partners?

Ian: I learned that relationships are your most valuable resource. In just six weeks, we were able to make meaningful relationships across the Defense Ventures cohort, the team at Insight, and the many portfolio companies. These relationships will become even more important as we all move forward and attempt to solve our nation’s toughest challenges.

What was your biggest surprise?

Ian: I think my biggest surprise happened in the first week, as I watched analysts fresh out of college speak to entrepreneurs on behalf of a multi-billion-dollar VC. The amount of trust Insight places into each of its employees is impressive and reminds me of the level of trust the military places in an 18-year-old fresh out of basic training. Both organizations are successful because of the amazing talent they onboard to the team and the professionals that dedicate their time to up-skilling and developing that talent.

What advice do you have for venture-backed companies who want to work with the Air Force?

Ian: My first recommendation is to try and understand DoD “colors of money” and acquisitions authorities. My second recommendation is to take time to focus on the actual problem the DoD is trying to solve. Often, the problem that is presented is simply a symptom of a different problem upstream and if the root problem is not addressed, we will all find ourselves trying to implement the wrong solution.

What are you going to take back to the Air Force? What do you think the Air Force should be doing differently?

Ian: I have an entire book full of notes to take with me back to the Air Force, but one observation is that Insight invests in amazing technical talent. This talent, at both the firm and portfolio company level, can take advantage of best-in-class technology and evolve them as their needs change. This shift is not as easy in the military so I would like to help the Air Force build processes that can more easily adapt to external variables and technological advances.

Ian, you have experience with USAF’s AI efforts, and currently, work in the think tank (strategic studies group) for the Chief of Staff of the Air Force. From those vantage points, and your recent Insight experience, what has been your impression of commercial AI companies, and their ability to serve the mission?

Ian: The artificial intelligence landscape is always changing and so I am constantly impressed when companies can take a new idea and quickly use it to solve a problem in the world. Talented founders and teams mean that the cycle time between ideation and solution is rapidly decreasing, and we need to take advantage of that so our nation can maintain its competitive advantage.

Richard, you have great field experience as a pararescue jumper, combined with your experience at DIU managing a human systems program — how should VCs be thinking about technologies designed for the field?

Richard: DoD organizations develop and advertise requirements in many ways. Sometimes, a company will look at a requirement and conclude that its products don’t quite meet that requirement. My advice is to always look at the whole picture. Even if you can’t provide the entire solution, there may we places where you can insert your technology, begin to build real relationships, and iterate with the defense customer.

How can venture-backed companies figure out what problems the DoD is trying to solve?

Ian: The DoD signals its problems in a variety of ways but there isn’t an easy-to-read website or article titled “Here is where we need help”. Instead, you must read through a variety of sources including the budget, science, and technology strategies, focus areas for the national laboratories, and speeches at military conferences. The signals are always out there, but sometimes, you must read through the tea leaves. In DoD, we need to keep working to make it easier for companies to understand our needs.



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Nick Sinai

Nick Sinai

Senior Advisor at Insight Partners; Adjunct Faculty at Harvard; former US Deputy CTO at White House; Author of Hack Your Bureaucracy