Who Is Jason Simpkins

Jason Simpkins is the editor behind The Crow’s Nest, the newsletter that runs the “Uber Air” promotion. He is a roughly 20-year veteran of financial publishing who specializes in defense, and he leans on a network of Department of Defense contacts to inform his work. That background matters because it shapes how he thinks about the investment behind the pitch, which is Joby Aviation (JOBY), and why he frames it the way he does.

Simpkins joined The Outsider Club in 2013 as assistant managing editor, a shop focused on resource, energy, and macro themes. Over time he moved into editing The Crow’s Nest, a newsletter built around what he calls “big trend” investments, the kind of multi-year shifts that cut across sectors rather than single-stock trades. The Uber Air pitch fits that template: electric air taxis as a big trend with one dominant company at the center.

How His Defense Background Shows Up

The defense angle is the telling detail. Simpkins’s specialty is defense and the military-industrial supply chain, and the Uber Air pitch leans on that expertise in a specific way. Joby’s aircraft is being tested by the U.S. Air Force through its AFWERX Agility Prime program, a real government initiative to evaluate electric vertical takeoff aircraft. For a defense-focused editor, that government relationship is not a side note, it is part of the thesis, a signal that the technology has cleared a bar most startups never reach.

The same logic appears across the flight-and-defense names he and his peers cover. We walked through the broader aerospace supply chain in our aerospace and defense stocks piece, where the difference between a diversified defense contractor and a single-aircraft startup is easiest to see. Simpkins’s framing tends to highlight the startup side of that spectrum.

What The Crow’s Nest Sells

The newsletter itself is a straightforward offer: $99 a year with a six-month refund period. That refund window is worth noting because it tells you something about the confidence level of the publisher, and it lowers the cost of taking a look. The Uber Air promotion is the funnel into it, teasing a “$10 startup” that “could climb to OVER $200” and pointing readers toward Joby.

The gap to watch is the one between the editor and the offer. Simpkins’s reputation is built on defense and big-trend research, which is a real specialty. The promo’s headline number, by contrast, is a marketing construction built on fleet math, roughly 14,000 aircraft earning meaningful profit by 2035, that no eVTOL company has approached. Our Joby Aviation stock analysis separates the company’s actual position from the $200 target, and our What Is Joby Aviation explainer covers the business behind the pitch.

How to Read His Work

The useful way to approach any newsletter editor, Simpkins included, is to separate the underlying idea from the marketing that sells it. The underlying idea here, electric vertical takeoff aircraft are a real technology with a real leader, is sound. The marketing, a $200 stock from a $10 entry, is not supported by the company’s own numbers today.

Simpkins brings a genuine specialty to the table, and that is worth something in a sector where government relationships and defense testing actually move the needle. The Joby pick sits squarely in his area of knowledge, which is more than a lot of financial promos can claim. That is a reason to take the research seriously, and a separate reason to check the price target yourself before acting on it.

The Honest Read

Jason Simpkins is a seasoned defense-focused editor with a two-decade track record and a real network, not a faceless promo name. His Uber Air pitch points at a genuine leader in Joby, and his defense lens is a legitimate edge. But the jump from a good editor to a good price target is exactly where careful readers slow down. The background earns a hearing; the math still has to work on its own.

The Defense Lens in Practice

The most concrete way to see Simpkins’s defense background at work is to look at what the Uber Air pitch emphasizes that a generalist editor might not. The pitch leans on the U.S. Air Force’s AFWERX Agility Prime program, the government initiative testing Joby Aviation’s (JOBY) aircraft, and treats that as a validation signal. For a defense specialist, that is a natural instinct: a government program is a serious technical filter, and it also opens a second revenue channel beyond civilian shuttle routes.

The same lens shows up across the broader flight supply chain, where diversified aerospace contractors earn steady defense revenue today. Joby’s defense revenue, by contrast, is still a program and a possibility rather than a booked stream. That distinction is exactly where a careful reader of Simpkins’s work should draw the line: the defense instinct is sound, and the commercial payoff is still pending. His background earns the thesis a hearing; it does not settle the price.

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