About Ben

Ben Cipperley spent 26 years in the Navy. The first 18 he served as an Explosive Ordnance Disposal office, with three tours across the Indo-Pacific, three years between Iraq and Afghanistan, and command in Guam. Which is to say, he has more experience than most.

What makes his background unusual isn’t the operational experience; plenty of veterans make the transition. It’s the Pentagon chapter that came after. A fellowship at the Stimson Center led to a resource sponsor role writing the Navy’s budget, which led to being pulled onto the team drafting the 2022 National Defense Strategy (mid-process, while Russian forces were marshaling in Belarus). Which led to working under the CNO on what became the Navy’s first force design document in 50 years. It’s a classified vision for the fleet in 2045 that, he notes, had quite a few robots in it.

He put an “Open to Work” banner on LinkedIn when he retired. The CEO of Havoc called him 20 minutes later.

About Havoc AI

Havoc AI is a collaborative autonomy software company. The pitch is deceptively simple: one operator, thousands of autonomous systems. The technology is the connective tissue, the software layer that lets a surface drone, an aerial drone, and a ground vehicle share a common operational picture and respond to commands from a single interface, rather than requiring separate operators, separate control systems, and separate data pipes for each platform.

The company was born from a conference convened by then-Undersecretary of Defense Heidi Shyu around the concept of “Hellscape,” IndoPaCom’s deterrence concept for a Taiwan scenario involving massive swarms of autonomous systems. The question in the room wasn’t whether the platforms existed. It was: how do you make thousands of them work together when a human brain can only track so many things at once? Founders Paul Lwin and Joe Turner quit their jobs the next day and started building the answer.

Early validation came through Silent Swarm, an exercise run by Naval Surface Warfare Center Crane. Havoc showed up with 12 prototypes of their Rampage platform. Representatives from NIWC Atlantic watched, then bought the prototypes on the spot. Those units shipped to Portugal to support Task Force 66. That’s the loop Havoc is now trying to close, and why they recently acquired Mavrik (air) and Teleo (ground) to make good on the multi-domain part of the pitch.

The business model is worth understanding clearly. The government is bad at buying software. It tends to need software wrapped in a hardware container before it can conceptually acquire it. Havoc has internalized this and partnered with eight different maritime platform builders, plus air and ground hardware partners, so that their autonomy stack arrives pre-integrated with best-of-breed hardware. They’re not trying to be the OS layer that makes everyone else’s platforms work together. But they’ll sell you the hardware too, because that’s how you get the check.

For more about Havoc AI: https://havocai.com/

Follow Ben: https://www.linkedin.com/in/bencipperley/

For more Crossing the Valley: valleycrossers.com

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

Crossing the Valley explores the journey from proof of concept to production in defense technology. New episodes weekly.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Luke Fischer

Luke Fischer is the CEO and co-founder of SkyFi. He is a former U.S. Army helicopter pilot and Special Operations veteran who transitioned through DIU (Defense Innovation Unit), Uber Elevate (as Head of Flight Operations), and Joby Aviation (leading government operations) before founding SkyFi in late 2021. He also spent time as an Entrepreneur in Residence in VC, which gave him direct exposure to what gets funded — and what doesn’t. That multi-domain journey across military, Big Tech, and venture is core to how he built SkyFi.

About SkyFi

SkyFi is a geospatial intelligence marketplace and platform that aggregates satellite imagery and analytics from hundreds of commercial satellite operators — making it accessible to any customer, anywhere, via web or mobile app. Rather than owning or launching satellites, SkyFi sits at the aggregation layer: abstracting away which provider owns the satellite and letting users task imagery or pull analytics with a button press. The business is currently approximately 80% government / 20% commercial, serving customers ranging from top global hedge funds and agriculture companies to Special Operations Forces, NATO, and allied governments across Asia. SkyFi closed its Series A in December 2024.

For more SkyFi: skyfi.com

For more Crossing the Valley: valleycrossers.com

Follow Luke: https://www.linkedin.com/in/lukemfischer/

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Todd Stiefler

Todd Stiefler is VP of Enterprise at WHOOP, overseeing the company’s B2B and B2G business lines. He brings an unusually cross-functional background to the role: a decade as a Senate defense staffer focused on missile defense and strategic nuclear deterrent, followed by product and commercial leadership roles at GE’s industrial IoT division, LMI, and Palantir. A self-described “tech nerd” and ultra-marathoner who finished the Leadville 100 in 27 hours, Todd found WHOOP the way most people find things that change their lives — by accident, scrolling LinkedIn late one night. He’s been building the company’s defense business ever since.

About WHOOP

WHOOP is a Boston-based wearable technology company focused exclusively on human performance and health optimization. Unlike general-purpose smartwatches, WHOOP does one thing: continuously measures high-fidelity physiological data — heart rate variability, resting heart rate, respiratory rate, skin temperature, and strain — and translates it into actionable metrics around sleep, recovery, and readiness. Its early customers included elite professional athletes, and it has since grown into a mass-market product worn by hundreds of thousands of consumers and, increasingly, military personnel. WHOOP is actively pursuing the DOD enterprise market, partnering with programs like SOCOM’s POTD and the Army’s Holistic Health and Fitness (H2F) initiative. The company’s enterprise division, led by Todd, handles everything from individual unit programs to large-scale institutional deployments.

Key Takeaways

1. Build for your most demanding user first.

In contrast to the “minimally viable product” framework, WHOOP’s early decision to build exclusively for elite athletes — with LeBron James and Michael Phelps among their first 100 customers — wasn’t a marketing stunt, but a product strategy. By targeting the most demanding performance environment, they built something rigorous enough to eventually serve everyone else. That same logic attracted special operators before conventional forces, and conventional forces before institutional DOD programs. They solved for the “edge cases” first rather than the average user, because they were solving their distribution challenge through their product design.

2. But the right product alone isn’t enough… you still have to solve the process.

Todd was direct about what WHOOP got wrong in its early defense push: they had a best-in-class product but hadn’t built the surrounding infrastructure. No contract vehicles. No data sharing agreements. No pricing architecture tuned to government procurement. “The DOD buys from people that solve their process, not their problem.” Getting that right — not just shipping a great device — is what actually enables scale. So while many of us laugh at high-ceiling IDIQs without real funding, the vehicle is a key ingredient.

3. The wearable itself is actually not the intervention.

This was one of the most important points from the episode: motivated, self-selected consumers who buy WHOOP on their own are signaling their desire to change their behavior. Warfighters handed a device in a conference room, with no context, no coaching, and no program design, often won’t. Even though the average warfighter may be more attuned to their body than the average civilian, in this case, if the warfighter doesn’t opt in, the product won’t deliver. This insight is why Todd never sees WHOOP going to a “push to all” rather than a “pull” based sales motion. If it’s foisted upon people, it will not produce the desired effect.

4. In federal sales, relationships and strategic partnerships beat conference booths.

Todd assesses that in the defense market, niche events where you can have real conversations, and partnerships with athlete management system providers who can pull WHOOP into their stack, have been the most valuable sources of leads. Trade show booths? Much less effective. As always, your mileage may vary, but it’s another reinforcing data point suggesting deep, niche relationships beat a larger breadth with high impressions.

5. Sell sustainable programs, not hardware deployments.

Todd’s north star for WHOOP’s next 12 months is helping customers build programs that will still be running in five years. That means bringing in WHOOP’s human performance experts and solution architects early, co-designing integration with existing data platforms, and being the vendor who asks, “What are you actually trying to achieve?” before taking the purchase order.

For more Crossing the Valley: valleycrossers.com | LinkedIn

For more on WHOOP: WHOOP.com

Follow Todd: https://www.linkedin.com/in/toddstiefler/

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Byron Boots

Byron Boots is the co-founder and CEO of Overland AI. Prior to starting the company, he was an associate professor in computer science at the University of Washington, where his research focused on machine learning and robot autonomy. Byron served as principal investigator on DARPA’s Racer program, one of the most ambitious off-road ground autonomy challenges the agency has run since its landmark Grand Challenge series in 2004–2005. It was in that role — out in the field, iterating under adversarial test conditions — that the insight and technology behind Overland AI took shape.

About Overland AI

Overland AI builds autonomous ground vehicle software and systems for the U.S. military. Their flagship platform, ULTRA, is a purpose-built unmanned ground vehicle with upgraded suspension, miniaturized compute, and a suite of sensors including stereo cameras, LiDAR, thermal cameras, and Starlink — capable of GPS-denied navigation in extreme off-road terrain.

The company operates across four primary concept of operations: ISR (intelligence, surveillance, and reconnaissance), logistics and resupply, layered protection (including counter-UAS), and breaching. Their go-to-market approach has been almost entirely driven by demonstrated field performance. Initially this came through DARPA experiments, then through DIU and direct work with Army and Marine Corps units. Overland has won contracts including the DIU Ground Vehicle Autonomous Pathways program and is currently focused on scaling into formations and establishing a permanent operational presence with the services.

Key Takeaways

Five principles from Byron’s journey that apply broadly to defense tech founders:

* Field, first. One of the most counterintuitive decisions Byron made at University of Washington was to hire strong vehicle mechanics as some of his first team members. It’s a simple but counterintuitive logic. You don’t have to build the perfect software in the lab before you put it on the vehicle because if vehicles could be repaired rapidly in the field, the software team could test more aggressively, fail faster, and iterate without fear. Thus, the vehicle mechanics gave the rest of the team leverage.

* The best BD is performance (with the lights on). Overland AI’s early business development was almost entirely organic. I pressed him on DARPA’s checkered history of transitioning programs, but in this case, DARPA invited the other services to watch their field experiments. Those experiments were credible, because the company often didn’t know what was coming. It wasn’t a PowerPoints brief or a table top conversation; it was an opportunity for customers to see the tech in action. That credibility dramatically accelerated their sales path.

* Build on top of what works. Byron’s framework for capability development is deliberate: get one robot working reliably, then add a second, then build multi-vehicle coordination. Don’t architect for the end state. Prove each layer before adding the next. This mirrors successful product development in commercial software but is even more important in defense, where integration failures in the field are immediately visible and costly.

* “If it’s not seamless, it won’t survive contact with the warfighter.” Despite the old saying “good enough for government work,” the operational bar for defense products is actually quite amorphous. Byron observed that “a slow or unreliable robot simply gets abandoned.” In other words, your project might die without you even knowing. The product actually has to perform well enough that operators don’t think about it. Only then can you expand the mission set, add payloads, or introduce multi-vehicle coordination.

* It’s not about your tech. The sooner you embrace this, the faster you’ll win.

Winning a contract gets you in the door, but a contract isn’t the same thing as winning warfighter trust. Byron draws a clear distinction between them. Overland's next 12 months aren't going to be defined by new contracts as much as they are going to be defined by creating "a permanent presence" with Army and Marine Corps units. I love this point because it suggests a totally different motion. It’s not about closing the deal or renewing it. It’s not about another slide or another meeting. It’s about doing things that don’t scale, having people side by side with the mission owners, and obsessing over the question of how to make your technology invisible inside existing workflows rather than celebrated as a novelty.

For more Crossing the Valley: valleycrossers.com

For more on Overland AI: www.overland.ai

Follow Byron: https://www.linkedin.com/in/byron-boots/

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

What happens when a Friday morning coffee turns into a term sheet by Sunday night?

In this episode, Forterra CEO Josh Araujo is joined by Ari Schuler, a returning CTV guest, to take us inside Forterra’s acquisition of goTenna.

Company Overview

About Forterra: Ground autonomy company enabling war fighters to shoot, move, and communicate more effectively. Technical stack includes autonomous driving systems, mission payload integration, and now mesh communications through the goTenna acquisition. Working with military customers across operational theaters. Founded 20+ years ago (as Robotic Research), recently closed Series C while simultaneously acquiring goTenna.

About goTenna: Mesh networking communications company providing interoperable comms, born from Hurricane Sandy in Brooklyn. Pivoted from consumer to military/public safety after discovering product-market fit with operators in Afghanistan, Iraq, and the southern border. Technology enables high node-count networks (100+ devices) sending low-bandwidth position/location data, critical for blue force tracking and preventing friendly fire.

About our Guests

About Josh Araujo: CEO of Forterra, building autonomous ground vehicle technology for military operations. Retired Marine, and Jefferies investment banker covering aerospace and defense. Joined Forterra (then Robotic Research) in 2021 as the first non-technical hire, now leading a company with 20+ years of autonomy innovation transitioning to programs of record.

About Ari Schuler: Former CEO of goTenna, now leading the communications division at Forterra. Built goTenna’s pivot from consumer to B2G, deploying mesh networking technology in conflict zones globally. Former DHS official who created Customs and Border Protection (CBP)’s innovation team, bringing government operator perspective to commercial tech development.

Key Takeaways

1. Skip the vitamin, find the medicine.

Ari’s mentor gave him a deceptively simple framework: are you selling something people want (vitamins), or something they can’t live without (medicine)? goTenna started as a consumer product, but product-market fit became unmistakable once the technology hit Afghanistan, Iraq, and the southern border. Ari explains that when you found the true medicinal use case, you go all in. Straddling consumer and government markets wastes capital and credibility that companies don’t have to spare.

2. The ability to sustain operations in the field is the real moat.

Both Forterra and goTenna had extraordinary technical pedigrees: Forterra’s co-founder holds 100+ patents, and goTenna’s mesh protocols are proprietary and deeply differentiated. But Josh was explicit: deploying at scale into combat environments is “miles apart” from having a cool demo. The muscle required to do customer success, field maintenance, and operational support in places like Afghanistan or Ukraine is not taught in any graduate program.

3. In M&A, cultural alignment is what ultimately determines deal success or failure.

The core of the conversation centers on how Josh turned a term sheet around in 72 hours, from a Friday morning coffee between Ari and Scott Sanders (another CTV alum), to an afternoon board meeting, to a signed term sheet by Sunday night. This kind of speed is not only a function of high caliber financial modeling and expertise, but of a clear strategic rationale and cultural fit. Josh talked about his view that even the best business alignment in the world can’t overcome a cultural mismatch. Culture doesn’t mean squishy values in this case. It refers to the companies’ shared mission focus, values, and tech stack (NetSuite, Arena, JIRA).

4. The defense VC funding model is creating a structural problem for which consolidation is the only solution.

Josh flagged a concern that most defense tech founders are quietly aware of: many of the best companies in this space have great technology, great teams, and genuine product-market fit, but lack venture-scale TAMs. VC math requires one in a hundred to go 100x. At the risk of sounding trite, that calculus alone will not support the entire ecosystem of mission-critical hardware businesses. As a result, if venture is the primary tool, companies that shouldn’t fail will fail because of capital structure problems. This is why Josh is shaping Forterra into a leading consolidator to create a home for these companies.

5. In a post-merger integration, the first priority is “do not break what’s working for the customer.”

Too many post-merger integration efforts try to move fast, combine everything, and extract synergies. In this deal, Josh and Forterra explicitly rejected this. The approach has been phased and deliberate: first, validate the technology combination (goTenna’s X2m module was physically integrated into Forterra’s Vector platform within 30 days, achieving 25x the range of the previous radio). Second, resource the acquired team to execute on their existing pipeline. Third, after the teams have developed organic trust, start to combine go-to-market and engineering functions. This cadence matters because defense vendors cannot afford to push artificial disruptions on their customers. As Ari explains, “We can figure out the HR systems. What we can’t do is mess up operational deployments.” The customer relationship is paramount.

For more:

* Website: Forterra | goTenna

* LinkedIn: Forterra | goTenna

* Follow Josh: https://www.linkedin.com/in/josh-araujo/

* Follow Ari: https://www.linkedin.com/in/ari-schuler-1ab93239/

* Follow Crossing the Valley: https://www.linkedin.com/company/102082197/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Dino Mavrookas

Dino Mavrookas is the CEO and co-founder of Saronic. He served 11 years in the U.S. Navy SEALs (2004–2015), with his final five years on SEAL Team Six. After leaving the military, he transitioned to private equity at Vista Equity Partners, where he spent roughly five years before the pull of mission-driven work drew him back to defense. Dino describes his transition as a gradual realization, like being a “frog in boiling water,” that he wanted to dedicate his career to building solutions that protect the country. He founded Saronic in September 2022 with backing from 8VC and a slew of other high profile investors.

About Saronic

Saronic is a maritime autonomy and shipbuilding company headquartered in Austin, Texas. Founded in September 2022, the company designs, builds, and deploys autonomous surface vessels for the U.S. Navy and allied forces. In just over three years, Saronic has grown to approximately 1,000 employees across six U.S. locations and two international offices (Australia and UK). The company’s flagship products are Corsair, a 24-foot autonomous speedboat built at their 500,000 sq. ft. Austin facility (capacity: 2,000+ units/year), and Marauder, a 180-foot autonomous ship being built at their shipyard in Franklin, Louisiana. Saronic secured a $392 million contract with the U.S. Navy in late 2025, with the Secretary of the Navy publicly endorsing their approach as the model for future procurement. The company has announced Port Alpha, a $5B+ initiative to build the world’s largest and most advanced shipyard, with the goal of producing 10 million gross tons annually. This would effectively 100x current U.S. shipbuilding capacity.

For more on Saronic:

* Website: saronic.com

* LinkedIn: https://www.linkedin.com/company/saronic-technologies/

* Follow Dino: https://www.linkedin.com/in/dino-mavrookas-190244127/

* For Careers: https://jobs.lever.co/saronic

For more Crossing the Valley: www.valleycrossers.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

How Wirescreen is Turning Investigative Journalism Into a National Security Intelligence Tool

About our Guests

David Barboza is the CEO and Co-Founder of Wirescreen. Before founding the company, David spent over two decades as a journalist at The New York Times, where he served as Shanghai bureau chief for 12 years and won a Pulitzer Prize for his investigative reporting on the hidden wealth of Chinese political elites. A history major by training, David’s career was defined by painstaking, multi-year investigations that required connecting vast networks of corporate records, government documents, and financial data across borders. He also co-founded The Wire China, an independent publication covering the U.S.-China relationship.

Bradley Martinez is the Head of Go-to-Market at Wirescreen. Bradley’s career has centered on using data and analytics to drive risk-based and opportunistic decisions, primarily in financial services. Before joining Wirescreen (shortly after the company’s Series A), Bradley held roles at FactSet and other data-driven firms. At Wirescreen, he has overseen the company’s pivot from a financial services focus to a government-first go-to-market strategy, building the partner networks and sales infrastructure needed to scale in the federal market.

About Wirescreen

Wirescreen is a Sequoia-backed intelligence platform that maps Chinese business networks and their global connections for the U.S. government, defense contractors, and the broader national security community. The platform aggregates millions of Chinese corporate records (including ownership structures, investment flows, patent filings, supply chain relationships), translates them into English, and connects them to reveal hidden relationships between commercial entities and state/military actors. Originally conceived as a business intelligence tool for financial services, Wirescreen found its strongest product-market fit serving government agencies dealing with the complexities of great power competition. Use cases span export controls, IP theft investigations, CFIUS reviews, fentanyl precursor tracking, university research security, critical minerals mapping, and defense supply chain vetting. The company also operates The Wire China, a journalism division that both generates revenue and serves as a data quality feedback loop for the platform.

--

For more on Wirescreen: https://wirescreen.ai/

Follow David: https://www.linkedin.com/in/david-barboza-7bba4325

Follow Bradley: https://www.linkedin.com/in/bradleymartinez/

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

Subscribe to Crossing the Valley: youtube.com/@CrossingtheValley

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Our Guests

AJ Piplica is the CEO and co-founder of Hermeus, a defense technology company developing hypersonic aircraft powered by air-breathing engines. His technical background centers on aerodynamics and hypersonics, with early career work on rocket engines and re-entry systems. Unlike many defense tech founders who come from software or commercial tech, AJ’s obsession with speed and aviation started in childhood and led him down the space track in college before gravitating toward the aviation side of hypersonics. He chose this path specifically because he wanted to push boundaries rather than spend a career optimizing incremental performance improvements on existing turbine technology.

Zach Shore was recently promoted from Chief Revenue Officer to President of Hermeus. After beginning his career as a Marine Corps Intelligence Officer, Zach served in a variety of industry roles, including as a consultant at Deloitte, Sr Director of Business Development for JAD C2 at Anduril, and Vice President of Product at Vertafore before joining Hermeus in 2022.

About Hermeus

Hermeus builds hypersonic aircraft designed to operate in what AJ calls “the final frontier of aviation.” The company focuses on air-breathing, reusable systems rather than expendable rockets or boost-glide vehicles. Their approach mirrors the commercial space industry’s transformation of launch: prove you can iterate rapidly on full-scale hardware by treating vehicle loss as an acceptable cost of learning when no crew is involved. Hermeus has won Other Transaction Authority (OTA) awards like Chimera and Antares, where the government pays for data and milestone achievements rather than traditional cost-plus development contracts. The company is building 30,000-60,000 pound aircraft, which requires substantial upfront capital and a production-first mindset from day one.

Key Takeaways

1. Separate mission assurance from safety to unlock hardware iteration

The most critical insight from the commercial space revolution applies directly to hypersonics: hardware risk and human safety risk are fundamentally different categories. Traditional aerospace culture treats hardware loss with nearly the same level of concern as human casualties, creating a risk-averse engineering environment that prevents the kind of rapid iteration required to advance into new flight regimes. The regulatory frameworks inherited from crewed aviation assume that preventing crashes is paramount, but autonomous vehicles enable a different approach where controlled crash scenarios become acceptable learning opportunities. This shift in mindset allowed SpaceX to iterate at full vehicle scale, and Hermeus is applying the same principle to air-breathing hypersonics.

2. Build products for operators from day one, not technology looking for a mission

The traditional research lab model follows a sequential path: develop interesting technology, demonstrate it works, then attempt to transition it to an operational program. This approach has a poor track record because it separates technology development from real operational requirements. Hermeus inverts this by starting with the operator and ensuring every development decision solves an actual warfighter problem that delivers substantial value. This explains why product companies often struggle to work with organizations like the Air Force Research Laboratory (AFRL), which see themselves as architects who design capabilities and expect contractors to build to spec. When you show up with your own product vision, there’s inherent friction with a “not built here” culture.

3. Concentration of capital beats diversification for hard tech at scale

The Defense Innovation Unit’s hedge strategy tapped into a fundamental reality of complex hardware systems: you cannot prototype your way to a 60,000 pound aircraft on Small Business Innovation Research funding. The temptation in government innovation programs is to spread risk by funding many small bets, but this approach fails for systems that require immense upfront investment to de-risk both technology and production scalability. While giving 25 companies $5 million each might work for low cost attritable systems, in capital intensive hard tech the Hermeus team would prefer to see the government fund five companies with $25 million and pick some winners. This requires clear accountability and transition pathways, but it enables companies to actually build hardware that can reach production scale.

4. OTA structures unlock speed by paying for outcomes instead of activities

Hermeus had success with awards structured as Other Transaction Authority contracts because they changed what the government was buying. Rather than paying for development activities and managing the technical approach, OTA programs pay for data generated along the way and for milestone achievements that deliver specific capabilities. This shifts the focus from process compliance to outcome delivery. For a company like Hermeus, this means the government isn’t dictating how to develop the aircraft or micromanaging spending decisions. Instead, they define what capability they need, and the company has the flexibility to build the infrastructure and processes required to deliver it efficiently.

Summary

Counterintuitively, the hypersonics race may not be about who has the most PhD researchers or the biggest simulation clusters. The Hermeus team suggests it will come down to who is willing to take hardware risk at full scale, iterate based on flight test data, and build products that solve real operational problems from day one. Hermeus represents a new generation of defense companies that learned from commercial space: embrace hardware iteration, separate mission assurance from safety, focus on operators instead of technology for its own sake, pursue concentrated capital rather than diffuse funding, and hold yourself publicly accountable through concrete metrics.

For more: hermeus.com

Follow AJ: https://www.linkedin.com/in/ajpiplica/

Follow Zach: https://www.linkedin.com/in/zacharyshore/

Subscribe to Crossing the Valley: valleycrossers.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

About Ian

Ian Cinnamon is the co-founder and CEO of Apex Space, which he launched to solve a fundamental bottleneck in the space industry: the lack of available, high-quality satellite platforms. Prior to Apex, Ian worked in aerospace engineering and identified the satellite bus as a critical constraint for the growing commercial and defense space ecosystem.

About Apex Space

Apex Space is a merchant supplier of satellite platforms (buses), building standardized, high-volume spacecraft that customers can purchase off-the-shelf and customize for their missions. The company has raised over $400M across its Series C and D rounds from investors including Andreessen Horowitz, 8VC, Shield Capital, and Interlagos. Apex differentiates itself through production speed, vertical integration, and a focus on unit economics. Surprisingly, they make money on every bus they sell. By mid-2026, the company expects to have approximately six satellites on orbit across various customer missions.

Key Updates (One Year Later)

1. DOGE Resilience: At the start of 2025, DOGE caused significant turbulence, cutting programs, shifting priorities, and forcing sales leaders to rebuild pipelines. Apex learned to “bend with the wind” rather than rigidly pursuing predetermined opportunities. Today, the company’s opportunity set is 10x larger than a year ago, but composed of entirely different programs than originally anticipated.

2. Raising Capital on Their Terms: Apex closed two major rounds in 2025, a $200M Series C and a $200M Series D. The Series D came unsolicited from Interlagos, who saw Apex’s execution and customer traction and pushed to invest even when the company wasn’t actively fundraising.

3. Vertical Integration as Strategic Imperative: As Apex scaled, external suppliers couldn’t keep pace. So they’ve brought almost everything in-house. By mid-2026, 70% of Apex’s subsystems will have in-space heritage. By year-end, the target is full vertical integration. This required significant capital investment but ensures supply chain resilience as production scales.

4. Betting Ahead of Demand: Apex announced Project Shadow, a self-funded ($15M) space-based interceptor technology maturation program. They are positioning for massive opportunities even before demand.

5. Building for the Bubble: Ian believes defense tech and space are in a bubble that will eventually pop. So his goal is to ensure Apex never needs another dollar of outside capital to survive. The company is profitable on every satellite bus it sells. This operational discipline means Apex can weather a market correction while competitors dependent on continuous fundraising may struggle.

Learn more: apexspace.com

Subscribe to Crossing the Valley: www.valleycrossers.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com

ABOUT BEN

Ben Van Roo is the CEO and Founder of Legion Intelligence. He comes from a military family (his brother is currently on active duty), giving him both personal connection to and deep understanding of the defense community’s needs. His career encompasses a combination of academic rigor and operational execution.

ABOUT LEGION INTELLIGENCE

Legion Intelligence is an applied AI company that connects AI capabilities to the actual workflows, processes, and legacy applications used across the Department of Defense.

The Core Problem: AI models have gotten remarkably good, but they remain disconnected from how work actually gets done.

The Legion Product: Legion builds the infrastructure that makes any workflow, across any environment, AI-enabled. The company’s offerings runs on edge, cloud, or hybrid environments; connect to legacy applications without requiring expensive system integrator rebuilds; and are model-agnostic (e.g., work with open source, proprietary, and government models). Ben also says they are the first to deploy an agentic workflow platform in IL5 and IL6 classified environments.

KEY TAKEAWAYS

1. The Plumbing Problem Is the Real Problem

When Ben was at Primer in 2017, he watched open source models become “terrifyingly good.” But nobody was actually using them across their workflows. He realized it wasn’t as much about the model as it was about connecting AI to the six or seven systems people actually touch to get work done.

2. Find Champions Who See the Future

General Fenton at SOCOM was “light years ahead of everyone, including venture capitalists” in understanding enterprise AI. He wanted to bring AI across the enterprise before ChatGPT made it obvious. Legion secured their initial IDIQ contract because one visionary leader saw where things were going.

3. Get Technology Into Users’ Hands Immediately

The most important lesson Ben took from Primer was that feedback cycles are everything. At Legion, the philosophy became: “Any exercise, any event, anything where we can go—we’re going to be there.” Bring your own hardware, do all the work to get there, and prove it works.

4. Make Early Technical Bets That Seem Confusing

Legion was first to deploy GenAI on small form factors for national security. First on-prem. First on IL5. First on IL6. These investments seemed odd at the time, when others were just focused on the cloud. But they created defensible positioning as the market evolved.

For more on Legion: legionintel.com

Follow Ben: https://www.linkedin.com/in/vanroo/

Follow Noah: https://www.linkedin.com/in/noahsheinbaum/

Subscribe to Crossing the Valley: valleycrossers.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.valleycrossers.com