Admiral Eric Olson Explains What Emerging Technology Companies Get Wrong When Working with the Military
Last November, Secretary of War Pete Hegseth announced sweeping proposed changes to the way the U.S. Department of War (DoW) acquires solutions and services in an attempt to clear bureaucracy and expedite the provision of mission-critical tools and technologies for the warfighter. Many of these proposed changes are designed to accelerate the acquisition of innovative technologies – making it faster and easier for the DoW to get the newest technological capabilities into the hands of operators at the tactical edge.
If realized, these changes to the acquisition process will open the door for entrepreneurial technology startups and innovative emerging technology companies to bring their cutting-edge solutions to bear for the warfighter. However, many of these companies have historically struggled to do business with the DoW not because of bureaucracy, but because of a lack of understanding of the military’s challenges and other cultural issues.
To get a better understanding of these issues and how emerging technology companies can overcome them, we sat down with Admiral Eric T. Olson, a retired Navy SEAL, former U.S. Special Operations Command (SOCOM) Commander, and current advisory board member at AstraNav—a navigation technology company specializing in resilient positioning solutions for mission-critical applications.
The Last Mile (TLM): You were the first Navy SEAL to reach four-star rank and led the U.S. Special Operations Command (USSOCOM) during a critical period in the Global War on Terror. In your experience, what do companies tend to get wrong when they first start working with government—and especially military—customers?

Admiral Olson: Small companies often behave as if they fully understand the military’s complexity and operating environment, and very few do. Even if a company understood it in the past, that understanding may no longer be current. The military changes constantly, week by week and month by month, and if you’re not part of the military, it’s difficult to stay up to date.
Another mistake some companies make is stereotyping. Companies that have real, experienced veterans from the military and the intelligence community don’t fall into this trap the way others do. But some companies rely too heavily on movies they’ve seen or books they’ve read to shape their understanding of the environment and the people they’re engaging with.
When those are your primary reference points, it’s very easy to get it wrong.
TLM: Why do you think it’s important to educate end users on new technology, and how can companies tactically do this without coming across as trying to sell a product or service? What are some critical things to educate users on when deploying new tech?
Admiral Olson: Typical marketing strategies assume you already have the answer to the problem and understand the full depth and complexity of that problem, well enough to present a ready-made solution. That’s a risky assumption.
It’s important to educate and explain why a product was developed the way it was and what its capabilities are, rather than positioning it as the answer to everything. If you do that, you allow the end user to determine how best to apply it to their specific situation. That’s very different from presenting something as a universal solution.
Education tends to be mutual. It’s less about teaching and more about discussion and creating an exchange where both sides gain insight. When that happens, understanding improves on both ends, and the product itself becomes better.
TLM: New military technology often fails due to integration challenges or slow procurement cycles. How can companies overcome these obstacles?
Admiral Olson: One of the phrases that became popular over the years—and I think led us astray—was the idea of the “speed of war.” People instinctively interpreted that as tactical speed. But I think the real speed of war is the speed of procurement and logistics. Without those, nothing happens at the front end.
Anything that improves procurement cycles and logistics cycles matters. The companies I’ve seen do this best tend to do two things well.
“If a company can help the end user articulate that requirement through a partnership, it significantly speeds up the process and helps get needed capabilities to the field faster.” –Admiral Olson
First, they work closely with the end user and develop a genuine partnership. Sometimes that partnership is built with former teammates, but the approach is the same: tell me what you need, I’ll tell you what we can do, and we’ll figure it out together. Through that partnership, they iterate toward a solution, and those solutions tend to be better.
SOCOM had an advantage here. It still had to follow acquisition laws and regulations, but it also had some special authorities. We could shorten the operational test and evaluation cycle to get capabilities into the field faster and see if they actually worked. We still did safety and effectiveness testing, but we didn’t have to put everything through months or years of evaluation.
That ability to move faster was tied directly to partnerships. You iterate a solution to about 80 or 90 percent, get it into the field, and see how it performs. Companies operating that way helped everyone involved.
“If you want to equip the warfighter, you need to think about the men and women in the field who have to carry everything.” –Admiral Olson
Second, they have someone inside the company who understands how to write a requirement. Companies like AstraNav and goTenna often think faster than the military acquisition system. One of the system’s structural challenges is that, in order to buy something, there has to be a formal requirement. Unfortunately, that requirement often doesn’t exist because a company has created a solution for a problem that hasn’t yet been articulated.
If a company can help the end user articulate that requirement through a partnership, it significantly speeds up the process and helps get needed capabilities to the field faster.
TLM: Special Operations relies heavily on strong interagency and international partnerships. In the technological domain, how critical is it for USSOCOM to actively seek partnerships with commercial tech ventures?
Admiral Olson: I agree it’s important to build partnerships, but the goal isn’t entrenchment – it’s an active, engaged, and mutually beneficial relationship.
Companies need to reach out to the military, and the military needs to reach out to companies when new capabilities come onto their radar. One of the fundamental flaws in the system is that it’s hard for small companies to know who to talk to in order to get their capabilities in front of the people who might find them valuable or essential.
“…the real speed of war is the speed of procurement and logistics. Without those, nothing happens at the front end.” –Admiral Olson
Once you figure that out, keeping the door open matters. Relationships have to be nurtured in both directions. Everyone is busy, and a relationship that gets ignored for too long tends to be replaced by another one. So once those doors open—even just a crack—it’s important to keep that relationship going.
TLM: For companies that are in the business of equipping our warfighters, what are the most important things to consider when taking on this task?
Admiral Olson: If you want to equip the warfighter, you need to think about the men and women in the field who have to carry everything. Simplifying equipment for use in the field is critical. You have to assume that every piece of gear will be used in extreme conditions – when it’s hot or cold, wet or dusty, in total darkness or blinding light.
Power sources matter as well. We had far too many different batteries in inventory. Equipment that could operate with common or flexible energy sources was far more valuable than gear that required a unique battery. Power draw, adapters, connectors, and battery commonality are important in the field.
Understanding how operators use equipment also matters. They’re using it with night vision goggles on, wearing gloves, under stress, in inclement weather, and in difficult terrain. When those realities are built into the design from the start, the equipment becomes far more useful for the men or women carrying it into the field.
In the second part of our two-part conversation with Admiral Olson, we look at some of the specific challenges the DoW faces as it shifts its focus from the asymmetrical Global War on Terror to a new generation of peer and near-peer adversaries.
Header image was sourced from the Defense Visual Information Distribution Service (DVIDS).


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