The Pentagon Has Learned From 1928. What Can It Learn From 1917?

In "Learning to Fly Again," I described how the United States entered World War One three years behind in the air, and how it caught up. On October 19, 2026, the Pentagon issued a memo and Owen West, who leads Project Agincourt, subsequently laid out how the department will build an Autonomous Warfare Command. His memo deserves a close reading against the record of 1917.

The Pentagon Remembers 1928

West opens by recalling 1928 when Secretary of War Dwight Davis ordered the Army to test a unified mechanized force of tanks, armored trucks and motorized infantry. The Army soon disbanded that unified force and split mechanization among the existing branches as add-ons. It took the German blitzkrieg of 1940 to force the creation of the US Armored Force.

Agincourt aims to avoid repeating 1928. It will stand up a four-star Autonomous Warfare Command (AUTOWARCOM) by 1 October 2027. The command's commander will have the authority to "drive the largest institutional change since the interwar years." West states the goal plainly: "The goal is not a particular drone. It is a system built to adapt at scale."

Where The Memo Echoes 1917

On four points, the memo reads as if its authors had studied the American air effort of 1917–18.

Asking for evidence. In 1917, planners promised to darken the skies over Germany, and the causes of that ultimately failed promise ended up being the subject of the Hughes investigation. West writes that new systems "will not be declared ready on paper." Competitions, exercises and combat performance will decide which systems scale. Every auditable dollar must lower the cost per kill or the risk to the force. The memo will measure success by how long a fielded solution takes to solve an operational problem.

Learning at the edge. In 1917, the Bolling Mission went to the front and asked the people who flew and maintained the aircraft which types to build. Agincourt pairs companies directly with operational units and calls those units "incubators."

Valuing the operator. American pilots were trained in French and British schools and learned from the American veterans of the Lafayette Escadrille. West highlights "an unmatched NCO corps" as one of two American strengths.

Building an institution. NACA, founded in 1915, mattered more than any single aircraft of 1918. AUTOWARCOM aims to make adaptation itself the main product of a permanent command.

1917 Asks Three More Questions

Who will build at scale? The Liberty engine succeeded because Detroit could build a stable, standardized component by the thousands, and because Allied orders had already built American capacity.
The Agincourt memo says nothing about industrial capacity: A command that cuts systems quickly after each competition protects the taxpayer, but will suppliers build factories for a demand that can disappear the next quarter?

Where is the front? In 1917, the United States learned at the front of a war it had not yet joined. The Agincourt memo relies on competitions, exercises and combat performance, yet never mentions Ukraine, where combat performance is measured every day.

Whose designs will American forces use? Most aircraft the American Expeditionary Forces received in 1918 were superior French designs and necessity had overcome national pride. Will American forces adopt Ukrainian designs where those designs outperform domestic programs?

The Clock Is Running

West quotes the Chairman of the Joint Chiefs of Staff General Caine: "If not us, who? If not now, when?" 

For investors, the questions are of  a different nature. In 1917, Detroit built the Liberty engine, and the front left the DH-4 behind. In today’s context, the questions would be “Which companies build what every winner will need in this conflict and the next? And who pays to scale them while they wait for a buyer?”

In my next post, I will turn to what these questions mean for early-stage investors in defense, intelligence and aerospace.

Learning to Fly Again: Arming for a War You Are Not Fighting

Russia invaded Ukraine on 24 February 2022, 1,707 days ago at the time of writing. This war has already lasted 140 days longer than World War One.

The United States is not a combatant in Ukraine. It also did not fight in World War One until April 1917, almost three years into the war. Until then, US banks lent the Allies billions of dollars and American factories filled their orders. A nation that watches a war from outside finds it hard to know where to invest, because the combatants change their weapons faster than an outsider can follow. The United States had to learn this in 1917, and its armed forces face the same challenge today.

America started three years behind

Since 1914, Europe's air forces had moved through several generations of fighters and had split air power into pursuit, reconnaissance, bombing and ground attack. When Congress declared war on 6 April 1917, the Army's air arm was a section of the Signal Corps. It owned fewer than 300 aircraft, none fit to fight over the Western Front, and a few dozen qualified pilots. It had no combat-tested design, no military engine in volume production, and no doctrine.

The United States did have assets Europe lacked: a vast automotive industry, money, and young men eager to fly. Allied orders had already expanded its munitions, steel and machine-tool capacity. Congress had also laid institutional groundwork: It created the National Advisory Committee for Aeronautics (NACA) in 1915, and the National Research Council followed in 1916. Both shaped American aviation for decades.

Rapid innovation outpaced America's late start In July 1917 Congress appropriated $640 million for aviation, then the largest single appropriation in American history. Planners promised more than 20,000 aircraft.

To reach that volume, the Army chose the British DH-4 two-seater,  an airplane that had first flown a year back in August 1916, fitted it with the American Liberty engine, and tooled up.
The front moved on while the factories retooled and the first American-built DH-4s reached France only in mid-1918. Crews judged the type outdated and called it the “flaming coffin” because its fuel tank caught fire easily. Only about 1,200 had crossed the Atlantic when Germany collapsed. Most of the American-built aircraft never left the United States.

America caught up by learning, borrowing and building

The United States still closed the gap within 18 months.

• It learned from the front. In June 1917 the Bolling Mission went to France, Britain and Italy and asked the people who flew and maintained aircraft which types to build. In the end, most of the roughly 6,000 aircraft the American Expeditionary Forces received were French, among them the SPAD XIII and the Nieuport 28. National pride gave way to necessity and effectiveness.

• It mass-produced what industry did best. Engineers designed the Liberty L-12 engine in about a week in May 1917. Detroit knew how to make a standardized, high-volume component, and Packard, Ford, Lincoln and others built more than 13,000 by the armistice. 

• It trained with the allies. American pilots learned at French and British schools and at the American center at Issoudun. Veterans of the Lafayette Escadrille, Americans who had flown for France since 1916, formed an experienced cadre.
  
  

Ukraine innovates in weeks

In Ukraine, measure and countermeasure follow each other within weeks. Cheap first-person-view drones made armor vulnerable. Electronic jamming answered them, and fiber-optic guided drones answered the jamming. Interceptor drones now hunt long-range attack drones. 

Both sides now build millions of drones a year, by their own accounts, mostly from commercial parts. Software, radio links, seekers and operator skill decide the outcome, and all of them change faster than an airframe.

US acquisition runs on a slower clock. A major program takes years to move from requirement to fielding. The Pentagon's Replicator initiative, launched in 2023, aimed to field thousands of attritable systems within two years, a pace the department considered fast. In Ukraine, two years span many generations of drone design.


Learnings are easy to state but difficult to act on

The lessons for today’s forces are well known and will not be repeated here. Many of them threaten the interests of the established defense industry, which explains why they are easier to state than to act on.  In my next posts, I will take a look at Project Agincourt and then turn to what this means for early stage investors in defense, intelligence and aerospace.

Same Angel Investor, Different Advice: Changes From Pre-Seed To Series A

The last piece was about how an angel’s posture changes from an informal relationship in the SAFE-and-no-board years to a more formal, renegotiated role once a board is constituted at Series A. This one is about something narrower and, in the day-to-day, more useful: what the content of good advice actually is at each transition, and why giving seed-stage advice to a pre-seed company or Series A advice to a seed company is a failure mode.

Disclaimer: Most companies raise on SAFEs for both pre-seed and seed, sometimes stacking several SAFEs across rounds that blur into each other with no priced round to mark a clean line. That ambiguity is exactly why the advice has to be anchored in what the company is actually proving at a given moment and not on the label of the round.

Pre-seed to seed: Underwriting whether the problem is real

At this stage, the founder's job is to prove the problem is real and to find signal fast. The central risk an active angel should be watching for is drift into vanity activity that looks like progress but isn't evidence of anything.

Four things are worth pressure-testing, and none of them are about the business model:

1. Founder-market fit and execution cadence
   Is the team learning quickly and shipping against a tight loop, or spinning on features nobody actually asked for? The question is whether the business is converting into signal.

2. Founder coachability, and specifically how they handle bad news
   At this stage the investor is underwriting the person even more than the plan. The plan will likely change several times before it's right. How a founder reacts the first time the investor tells them something they don't want to hear is a better predictor of the next eighteen months than anything in the deck.

3. Burn versus runway to the next real milestone
   Runway to a milestone that will justify the next raise is a forecast, and it's the number that determines whether the founder raises from strength or from desperation. 

4. Signs of premature scaling
   Hiring, spend, or a process built for a company that doesn't exist yet are the earliest version of a mistake that gets much more expensive to unwind after the next round.
   
   

Seed to Series A: Underwriting whether it's repeatable

By seed, the problem-is-real question should have mostly been answered. What Series A investors are underwriting is whether growth is repeatable and not just dependent on the founder hustle, and whether the organization is starting to look like something that can run without the founder personally closing every deal.

1. Unit economics and repeatability
   Growth that depends on the founder's personal charisma in every sales call isn't a business yet; it is a founder with a good pitch. 

2. Customer concentration and retention
   Is revenue durable, or is it resting on two or three accounts that could walk and take the growth story with them?

3. Organizational readiness
   Series A usually demands the founder shift from doer to builder-of-systems — from closing every deal personally to managing managers who close deals. 

4. Narrative discipline for fundraising
   Can the founder now tell a consistent, evidence-backed growth story to investors who weren't there for the early pivots and don't have the relationship context an angel does?
   
   

Installing the habit matters as much as naming the problem

There's a window of opportunity angel investors should use deliberately: the best moment to install the governance habits the next stage will require is right after each financing closes, and before the next fire drill starts while the founder still has bandwidth and goodwill for a process that doesn't yet feel urgent.

How that advice and governance get delivered matters as much as what gets delivered. The angel's actual edge, across both transitions, isn't reading a different checklist than the founder. It's knowing which item on that checklist is the one worth asking about this quarter. 

The socratic method of asking questions is a time proven method that lets the founder arrive at the concern themselves and not let the angel declare a problem. Founders own conclusions they reach on their own.

Your Angel Mandate Has an Expiration Date. Here's How to Renegotiate It

Zoom out from any single company, and an angel's career follows a fairly consistent shape in three time-bound phases for any invested cohort.

Phase	Typical duration	What's actually happening
Active deployment	Year 0 - 4	Capital goes out. A diversified angel typically writes 15–30 checks in this window.
Management & follow-on	Year 0 - 6 years	Focus shifts to mentoring existing founders, monitoring the portfolio, and deciding where to defend a position with follow-on capital.
Waiting & liquidity	Year 3 to 15+	Most of the calendar. Angel-backed companies take roughly 9–11 years, on average, to reach an acquisition or IPO, so even a short active window is followed by a long one spent simply waiting for an outcome.

Two structural forces compress the active window. One is capital: angels invest personal money, and once the "high-risk" allocation is deployed, new checks wait on prior ones returning capital. The other is fatigue: with 60 - 70% of individual investments returning zero and full-cycle exits often a decade out,  many solo angels burn out and step back after ten to fifteen years. 

Somewhere around Series A, the governance picture most angels have been informally operating on disappears and a real one replaces it. It's worth spelling out what actually changes, because the instinct to keep doing what worked until then is usually the wrong one.

A few things happen at once. The company converts from SAFEs to preferred stock and a board gets formally constituted. Typically the lead Series A investor takes a seat, sometimes a second institutional investor, hopefully an independent director. Board members now carry fiduciary duties such as care and loyalty to the company and its shareholders as a whole. This is a materially different obligation than an angel casually advising a founder. Information starts flowing through formal channels: board decks, monthly or quarterly board packets, sometimes committees for compensation or audit. And the founder's time, which used to be available for an unscheduled call with a helpful early check-writer, now is formally claimed by the people with a board seat and a fiduciary reason to use it.

Most angels do not end up with a seat at that table. Check sizes at seed are usually too small relative to the Series A lead to justify one, and a crowded cap table of individual board seats is exactly what a new institutional investor will resist. So the realistic question isn't "how do I get a board seat", it is how to define a role that still adds value. In practice, that tends to land in one of three places:

• A board observer seat, negotiated into the side letter at the seed round rather than requested after the fact. It carries forward, gives visibility into board-level decisions without a fiduciary vote, and is far easier to secure before the cap table gets competitive.
  
  

• A formal advisory agreement, with an explicitly scoped mandate and sometimes a modest equity refresh. This is the mechanism by which the "audit your superpower" boundary from the seed stage gets written down rather than left as an informal understanding.
  
  

• A narrower Strategic Connector role, where the angel steps back from day-to-day operating involvement because the company now has real executives and a real board doing that job, and the highest-value contribution left is network access when it matters: the enterprise intro, the next-round investor, the exec hire.

This is more of a recalibration of the role than a downgrade. The Operational Co-Pilot role that was genuinely useful when a company had no VP of Sales and no board is often actively unhelpful once it has both. The angels who navigate this well are the ones who treat the arrival of a board as a scheduled renegotiation of their own mandate and not a demotion.

These transitions happen because the angel decided, at each stage, what role was actually useful and asked for it. The angels who stay relevant longest are the ones who keep renegotiating the mandate as the company's governance catches up with its ambition.

The Three Postures of an Angel Investor

There's a version of angel investing that looks like this: write the check, read the quarterly update, vote yes on the board resolution, wait. Disciplined, systematic, and almost entirely passive. It's a legitimate way to run a portfolio. It is also the version that adds the least value both to the founder and, over a long enough horizon, to the investor's own return.

The more useful frame is that angel investing isn't one job. It's a sequence of different jobs, and the job changes on a schedule the angel doesn't control. It is set partly by how much capital the angel has deployed, and partly by the governance event most angels underweight: the point at which the company gets a board.

Three ways to show up after the check clears

Once capital has been committed, angels tend to settle into one of three postures.

The Analytical Monitor behaves like a mini-VC: reads the financials, exercises information rights, votes on resolutions, waits for the outcome. Systematic, low-effort, low-friction — and largely detached from the thing that actually determines whether the investment works.

The Strategic Connector doesn't do the day-to-day work but compounds a career's worth of relationships on the founder's behalf: introductions to enterprise buyers, key hires, and the introductions to Seed and Series A firms that will decide whether this company gets to exist in eighteen months.

The Operational Co-Pilot goes further: a fractional executive who helps build the first sales playbook, pressure-tests the financial model, or shapes the early engineering org design.

None of these is wrong or right. The case for leaning toward Connector and Co-Pilot, deliberately, is a de-risking argument. Early-stage startups don’t fail because of macro cycles, they fail because of an unwillingness to learn and pivot and of execution mistakes: the wrong first sales hire, a pricing model that doesn't hold, a go-to-market motion targeting the wrong buyer. An angel who actively coaches a founder through those specific decisions is actively helping reduce the 50+% failure rate to the next round. 

Why the early window runs on relationships, not rights

What makes the active posture possible in the first place, and that most first-time angels miss, is that there usually is no board at pre-seed.

Most early checks go in via SAFEs, a security explicitly designed to be fast and light on governance. There is no board seat that comes with it. No formal voting rights, no contractual claim on the founder's time, no table to sit at. Whatever influence an angel has in this window is not codified on paper. It's earned, offered, or simply taken, through the relationship.

It means the "value-add" angel isn't leaning on some formal governance lever. It means access is a function of how useful, low-friction, and trustworthy the angel actually is to the founder without any fiduciary structure enforcing the relationship. And it means the angel who wants to be more than a name on the cap table has to design that role on purpose, because nothing about the SAFE requires the founder to give it to them.

A few ways angels who take this seriously can structure it before it becomes a governance question

1. Audit your superpower and say so explicitly
   Identify the one thing you're good at, ideally better than most people in the founder's network: enterprise sales motion, pricing, a regulatory domain, hiring a first VP. Tell the founder plainly not to just send general updates but to call when they hit a wall in this specific area.
   
   

2. Agree on the cadence instead of leaving it open-ended
   A recurring 30 - 45 minute monthly call beats being on call for ad hoc late night texts. It's more sustainable for the angel and more predictable for the founder.
   
   

3. Define the triggers that warrant an unscheduled call
   Name the handful of situations that justify going off-cadence, so both sides know what "urgent" means: A competitor move, a hiring decision in your domain, a fundraising strategy question.

The key takeaway from all of this is that "angel investor" describes a capital commitment, not a fixed job description. The job is Analytical Monitor, Connector, or Co-Pilot from pre-seed onwards, operating on relationships because there's no board to formalize anything. 

The practical implication: whatever role an angel wants to play -  Connector, Co-Pilot, or some mix - the window to play it actively is genuinely short relative to the decade-plus the capital stays locked up.

What Four Investments Taught Me About Defense Tech Before I Knew I Was Learning It

Last week I was asked to co-chair the Defense, Intelligence and Aerospace Special Interest Group at the Band of Angels, alongside Rick Lu of Pacific Defense.

How did I get here?

One day you're an angel investor writing about industrial software, robotics and startup mechanics, the next you're co-chairing a group that vets seed-stage defense deals.

Aside from writings about military doctrine and satellites, it was only in going back through my portfolio to think about what I'd bring to the DIA SIG that I noticed four investments over the last several years that, at the time, I would not have filed under "defense tech." I filed them under "great technical team, differentiated tech, real customer pain." All four shared a second property: every one of them builds something a commercial customer needs and that a military customer needs for the same underlying reason.

Geosite built geospatial intelligence and property-risk analytics, the kind of thing an insurer needs to price risk on a piece of land, and the kind of thing an intelligence analyst needs to understand what's happening on that same piece of land. Descartes Labs, which does a substantial amount of work with the geospatial intelligence community, acquired the company in April 2024, and both were in turn acquired by Earth Daily Analytics (EDA).

Metalware is building security for firmware for the operators who build and run it, which turns out to be exactly what the Department of Defense and its suppliers need when they think about their own systems infrastructure. The company has been doing work for government primes on its way into direct DoD relationships.

Okapi Orbits is the clearest version of the pattern. As the number of satellites in orbit keeps climbing, someone has to manage the traffic and avoid the collisions. This is a space domain awareness problem for every commercial satellite operator and for every government that operates satellites of its own. The company raised a 13M seed round in 2025 to build that infrastructure.

Nobility Space builds air-breathing electric propulsion for satellites operating in Very Low Earth Orbit (VLEO), altitudes low enough for most spacecraft to sustain orbit. The promise of VLEO is enticing: sharper imagery, faster communications links, more frequent revisit rates, and a harder target to track. VLEO is naturally attractive for persistent intelligence, surveillance, and reconnaissance (ISR) and space domain awareness called out in the U.S. Space Force doctrine in April 2025. 

These are companies where the underlying technical problem is the same problem, viewed from two markets with different sales cycles, procurement processes, and risk tolerances. 

It is also the underlying theme of most of what I've written about military doctrine, innovation, and space over the years, including a piece I wrote in December on the Pentagon's Portfolio Acquisition Executive (PAE) model, where individual PAEs are given combined financial and product authority over a mission portfolio and are judged, as I put it then, not by compliance metrics but by "how quickly solutions are delivered, how relevant they are."

The Long Middle of the Founder’s Journey: Board Alignment, Trade-Offs, and Realism

Nobody talks about the long middle of the founder's journey. The years after conviction, but before clarity. It is the time where most startup stories are decided and characters are shaped.

I have watched a version of this play out with an industrial SaaS founder I am privileged to advise. From the onset everything looked great. The company solved a hard problem uniquely, had real customers, recurring revenue, credible investors and a friendly board.

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The friction showed up as the company scaled: the expectation an industrial company should grow like a SaaS unicorn, timelines not matching reality, a bulging capital structure. Not every good business can be stretched into someone else's success story. Founder and board constantly negotiated about control vs. trust, founder ambition vs. realism, speed vs. durability. Board meetings started optimizing for a clean narrative instead of hard trade-offs. Fundraising logic started dictating operating decisions. 

The founder was working harder and controlling less and the runway no longer was just financial, it became psychological.

Industrial software startups very rarely IPO. They are acquired by large industrial companies if they manage to become really large. If they are on the smaller side they get bought by private equity platforms that price EBITDA over growth.

Once those choices become explicit, everything come into focus: product calls get easier, conversations with acquirers become deliberate instead of reactive, and an exit stops feeling like failure and starts looking like completion. 

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This particularly ending did not produce a 10x outcome for the investors. 

It forged a founder who deeply understood the system, the trade-offs it demanded, and the cost of pretending otherwise.

It also delivered a very lucrative exit for a founder already focused on his next venture.