The strategic framework that guided Owl Autonomous Imaging through a market pivot, and the methodology behind selective operational curtailment.
Chuck Gershman took my call three weeks after Owl Autonomous Imaging closed an eight figure contract with the Pentagon. I asked him how close the company had come to failing before that contract landed.
“You really don’t want to drive the damn car off the cliff edge,” he told me. “The problem is when you do what we did, you get really, really close to the edge. And sometimes you’re there for a long time.”
I told him the fear probably fades once you’re on the other side of it. He corrected me twice.
“You don’t forget. You want to forget, but you don’t forget. I think we took a couple of tires over the edge. The whole car didn’t go over, but we got a tire over the edge. It was that close.”
For roughly two years before that contract, Chuck built in semi-stealth and ran no campaigns, gave no public talks, and pushed nothing. The market found Owl anyway, because a website that he’d stopped updating was still driving traffic organically.
Chuck runs this company on written rules, and he can recite each one on demand. Every one of them transfers to you, so let me walk you through them in the order that he arrived at them.
Rule one: pick the market you can actually penetrate
Owl started with two candidate markets, and Chuck chose between them roughly six years ago.
“You don’t necessarily want to start a company because you have a great product,” he told me. “You want to start a company because you have a problem that you can solve.”
Owl could solve several. Two adjacent markets looked like they had the most hyper-growth potential:
- Automotive and;
- Drones.
Chuck picked automotive because it had a well-defined customer base and fewer buyers in it, each buying at volume. The drone market in 2020 was fragmented across use cases that nobody had settled yet, and each of those use cases would have demanded a slightly different product.
“As an early stage company, we’re also aware that if you chase multiple markets, you get diluted really quickly. You run out of resources. You run out of money. It’s a good way to go bankrupt.”
That positioning secured 12 pilot programs with major global automotive OEMs. However, transitioning pilots to production presented structural hurdles: automotive buyers require high-volume, cost-optimized finished goods. In Gershman’s assessment, incumbent automotive buyers lack the incentive to nurture emerging technologies through early adoption curves.
Rule two: show a 10x capability or don’t raise at all
Owl’s website was built for those automotive buyers. It laid out the specific problems with nighttime driving, it named the regulatory efforts that were underway in Europe and the United States, and it established that automatic pedestrian braking at night was about to become a requirement. Only then did it explain how Owl’s technology met that requirement.
On top of that sat the proof. Chuck’s team mounted night vision cameras onto vehicles, drove at night and in fog, and published the footage beside a standard visual camera shooting the same conditions.
“You could quickly appreciate visually exactly what the value proposition was,” he said.
People inside the Department of Defense who had deep knowledge of thermal imaging were hunting for commercial companies that solved this differently from whatever they could acquire through normal channels.
They read that page, and they called Chuck. Their first question was whether the night vision capability was real or soon to be real. Their second was whether Owl would sell to them if the Department placed no conditions on Owl’s commercial sales.
The rule underneath that inbound call is blunt:
“It’s not enough, as an early stage company, to show a Me Too capability. The basic rule of thumb is you need to show a 10x capability.”
Chuck applies a stricter version of the same rule to fundraising:
“You don’t take other people’s money unless your unique value proposition is an order of magnitude better than the incumbents. If it’s not, then the incumbent will win, and you’d be wasting the money of your investors.”
Owl sells into a market where incumbents already exist, so that page had to demonstrate that Owl was different. The sequence Chuck used is this. First the video captures the imagination. Then the written numbers close the argument.
“Those videos don’t necessarily provide the 10x metric. They capture imagination, allow people to extrapolate, and then you follow that up with the written numbers.”
Rule three: go passive, don’t go dark
Two things hit Owl at once. The Department of Defense conversation meant a market pivot, and separately, Owl’s first automotive product missed the performance bar that Chuck’s team had set for it.
So he had a company that had just run a real campaign, generated real excitement, and now needed to pivot away from all of it while it rebuilt the product.
He didn’t take the website down, and he didn’t declare an official stealth mode.
“Our objective in the quiet period was to not create a situation where we were forcing inbound inquiry, but be prepared that if an inbound inquiry came in, we would field it, we would answer it, we would encourage it to the best that we could. We just stopped pushing and moved into a completely passive mode.”
In practice, Chuck downsized Owl’s go to market resources and put outbound marketing on hold entirely. The website stayed live and untouched.
One channel never stopped running at all: the newsletter that goes to Owl’s investor community.
Two years of that, and the inbound never actually dried up. “Through the entire quiet period, companies came to us, they found us, even though we weren’t out there.”
For organizations facing periods of restricted campaign activity, the distinction between active silence and total obscurity is critical. Complete silence erodes brand equity, whereas passive positioning maintains market awareness without incurring operational demand.
Rule four: pick one of three ways to win
Chuck holds that there are three ways a founder wins, and that every successful company does one of them far better than the other two:
- You out-manufacture everybody, the way Taiwan Semiconductor Manufacturing Company does.
- You build a categorically superior product, the way NVIDIA does.
- You run customer intimacy, which means you make your customer feel special.
“If you try to hit it right down the middle, you generally fail,” he said. “You need to be all in on one of those three things. If you try to be good at all three of them, that’s a recipe for disaster.”
When Owl took the defense contracts, Chuck committed to customer intimacy deliberately. He’s clear that the choice is temporary. You can migrate from intimacy toward superior product as your company matures. What you cannot do is run two of them at once.
Rule five: grow the contract from inside the contract
This framework represents the most replicable growth vector from Owl’s operational model.
Owl went from contracts in the hundreds of thousands, to contracts in the single digit millions, to an 8 figure one, and Chuck ran the same motion at every step. He’s blunt about why it works at all. You’re not cold-pitching anybody here.
“You have an existing customer. They know you, you know them. So it’s not a throw-it-over-the-wall message.”
The core driver of contract renewal is verifiable progress. A monthly reporting framework provides clear visibility into execution; demonstrating measurable month-over-month advancement directly reinforces account retention.
Reproduce This Win. Every part of this sat inside the engagement that Chuck’s customer was already paying for:
- Commit to a monthly status meeting and hold it live. Not a status email, not a dashboard link. Chuck’s team sat the customer down every 30 days and walked them through the work in PowerPoint, in a live meeting.
- Build the program plan and add real program management. Owl mapped the whole engagement behind the scenes, stood up a dedicated team on detailed schedules, and made sure every engineer and developer knew their role and communicated with the others directly.
- Step the customer through what changed, and map each change to their goal. The analytical rigor of the review is paramount. The session explicitly articulates incremental technical achievements and operational adjustments over the preceding 30 days, mapping each milestone directly to the client’s strategic objectives. This ensures complete transparency regarding value delivery.
- Structure the early contracts so that they test hypotheses. Owl’s first six figure contracts existed to determine what the technology could and couldn’t do, which problems it solved, and where it fell short. “We had a customer that was paying us to do our trade-off studies.”
- Report the bad results as honestly as you can. This is the counterintuitive one, and it’s the hinge. Owl reported the failures straight, and that bought the standing to push for the step function work that Owl actually wanted funded.
- Build each new proposal out of the last contract’s open questions. Every larger contract addressed the unresolved investigative items that the smaller one surfaced, so Owl never started a bid from a blank page.
What compounded across all of that was confidence in how Owl spent the customer’s money. Chuck describes the compounding asset as the customer’s belief that Owl would “spend their money wisely and spend their money effectively,” and he’s clear that the belief came from the reporting cadence, not from the technology.
“It was the same myopic energy of, we are not going to disappoint. We’re not going to disappoint. And we’re going to, to the best of our ability, over-deliver.”
Gershman also noted the underlying financial strain, a factor frequently omitted from growth narratives. Between the third and fourth contract phases, Owl experienced several months of zero contract revenue, presenting significant cash-flow challenges.
Rule six: the 85% rule
Owl is a dual use company, which means that the same technology serves a commercial market and a defense market in parallel. Plenty of founders say that about their own companies. Chuck put a number on it.
A minimum of 85% of every contract dollar has to fund research and development that Owl would have paid for out of investor money anyway.
The test is one question. In the absence of this contract, would Owl spend this money on this research regardless?
In practice they ran between 90 and 98%.
The 85% rule also works as a bid filter. Chuck reads the solicitation abstracts and asks whether the request runs parallel to Owl’s own product roadmap or diverges from it. Parallel requests get a proposal, and that proposal deliberately carries as much of Owl’s own solution as the request will allow. Chuck declines the divergent ones.
The 85% rule applies beyond government contracting. Early-stage founders routinely encounter opportunities that diverge from core strategy. Gershman emphasized the strategic trade-offs inherent in maintaining this focus:
“This is a level of discipline that is incredibly difficult. This is why early stage founders should get paid the big bucks. It’s the tough call.”
He draws a hard line between two things that founders confuse. You want customer feedback that sharpens your product while you hold your course, and you should go and find it. Customer money that pulls you dramatically off your vision statement repositions your entire company, and once you accept it you’re obliged to re-derive every assumption and every market analysis from ground zero.
Then Chuck named the failure mode that kills early stage companies outright:
“If you have multiple customers taking you in multiple directions at the same time, that is the kiss of death. You’re taking your company in three directions at the same time as an early stage company with limited resources. You could burn through all your money, burn through all your resources, and it would never convert.”
And those directions won’t resolve themselves on their own. As he put it, by definition they’re not going to converge.
His word for the fix is focus. He said it six times in a row.
Rule seven: hire for shared vision, not just for smart
I asked Chuck whether he architected the go to market himself, because he knew the mechanics cold in a way that founders usually don’t. He credited his chief business officer, Wade Appelman, and a chief financial officer with 30+ years across different markets. Then he named the screen that he actually hires against.
“You can surround yourself with lots of really smart people who’ve been there, done that. If you don’t have a shared vision, that’s another recipe for disaster.”
He’s specific about where disagreement belongs. Chuck wants his team to argue in the back room and to disagree on decisions freely… he treats that kind of friction as healthy. He requires consensus on vision, and he treats its absence as grounds to part ways.
Two mechanics from Chuck’s team are worth stealing:
- They mind map everything, technical work and product and go to market alike, to get every idea onto paper and congeal it into a plan.
- They run a human Gantt chart when a program needs full company alignment. Everyone goes into a room for 2.5 days, each stakeholder owns a swim lane, and they paste sticky notes onto a wall and move them until every dependency is mapped. Afterward they capture the whole thing into project software.
Rule eight: harden the message in private, then wait for your trigger
This sequence reflects Owl’s current go-to-market protocol and serves as a blueprint for repositioning without market disruption.
Long before anything went public, Owl developed the new drone-centric messaging and tested it under non-disclosure agreement, one to one, over PowerPoint, with potential investors and strategic partners.
“We used potential investors, strategic investors, and strategic partners to hone our message and to really get it to congeal. Be solid, concise, and powerful. But we didn’t put any of that in the public domain.”
The trigger for public disclosure depended on external market dynamics rather than arbitrary internal timelines. Owl recognized that the program would select multiple awardees. When a major incumbent supplier announced its award via press release, the program gained public visibility, enabling Owl to announce its selection once formal clearance was secured.
That press release started the campaign, and notice what it didn’t say:
“It effectively announced a pivot on our part, but we didn’t come out and say, oh, well, we’ve pivoted. We just came out and said, well, we won this award, and here’s what we’re doing.”
Then came the website changes. Chuck re-weighted it instead of rebuilding it. The automotive and autonomy pages stayed live, but they came off the splash page. The splash page became drone-centric, new drone pages went up, and the product pages barely moved, because “it’s just a different use case as opposed to a different product.”
The old market didn’t get deleted either. “We didn’t eliminate a market. We just added the drone market, but we put it front and center.”
Rule nine: don’t break the elasticity
Owl’s first automotive launch is the failure that taught Chuck the most, and he’s built the current relaunch around avoiding a repeat.
Here’s how he describes it:
“Your marketing and sales are like a spring. They have to be ahead. You can stretch that spring out so it gets ahead of the product, but you don’t want to stretch it out until you break the elasticity and it won’t snap back.”
So this time, Chuck and Wade worked backwards from the sample date and held the campaign to within a couple of quarters of release.
“Your gut says go, go, go. It’s time. We’re ready to go. But no, we had to stay disciplined to the clock, to the calendar.”
Two failure modes sit past that line. You build excitement, the product isn’t ready when the excitement peaks, and the momentum drains away. Or you go so early that urgency evaporates before there’s anything for anyone to buy.
The right number is specific to your category, and Owl builds hardware and software together, which lengthens both the time to market and the customer’s own learning curve. Work backwards from your own sample date and find yours.
Rule ten: take the luck, and build the version you can manufacture
The Pentagon pre-sold Owl’s program across the services, across other defense organizations, and into NATO nations, which means Owl’s pilots now arrive predetermined instead of needing to be sold. Chuck won’t take credit for that.
“If you’re a founder of a company, you have to both be good and you have to be lucky. A little bit of serendipity goes a long way. But hey, don’t look a gift horse in the mouth. If they’re going to do it, take it. That’s just golden marketing.”
Then he gave me the version for founders who’ll never get that gift. In other markets you work harder for the same reach, and the mechanism is trade shows, speaking engagements, panels, and thought leadership published in the right periodicals. Owl ran exactly that program during the automotive years, and Chuck plans to restart it.
There’s one more advantage he’s sitting on. Owl’s major incumbent competitor has become a de facto monopoly in its space, and Chuck sees that as the best possible thing to compete against.
“Monopolistic companies all make the same mistake. They piss off their customer base because they can. And this company is doing exactly that. Their customers hate them. So as soon as they get a sense that there’s an alternative, they make a phone call. It’s the best marketing we could ask for.”
And the corollary, which I’d have you write down: one company does not make a market. When you see a monopoly, you’re looking at a market that’s ripe for an additional player.
Flatline
I asked Chuck what he wanted you to take away, and he gave advice.
He calls it flatlining, which he borrowed from the medical term and inverted. Your mood swings hard as a founder, from a win in the morning to a loss by the afternoon, and the discipline is that you train yourself to refuse both the highs and the lows and hold the line through the middle.
The concrete version that he actually operates by is this. Never send an angry email on the day you want to send it. Wait 24 hours. “That email will not be nearly as angry, and won’t piss off nearly as many people, and probably won’t have as many second-order negative effects.”
Every rule Chuck gave me is the same instinct pointed at a different system:
- The 85% rule points it at his contracts.
- The line between feedback and money points it at his customers.
- The elasticity limit points it at his calendar.
- Flatlining points it at himself.
P.S. Chuck also told me about a hire that he didn’t make. Owl never put a product manager in place soon enough on the last launch, because Wade could do that job and so could Chuck, so between them it got covered.
He calls that a mistake now, because nobody owned it. Owl’s first go to market hire this time is a product manager who owns the entire product release structure. When you can do a job yourself, that’s the most common reason the job goes unowned, and the ownership gap doesn’t surface until launch day.
