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To my fellow Veteran Entrepreneurs,
The hardest battle isn’t the one we fought overseas.
It’s the one many of us are fighting right now, against versions of ourselves that no longer exist.
We spent years becoming an operator. A Marine. A SEAL. A Soldier. We mastered our crafts, earned our identities, and led teams in some of the most hostile and challenging environments on earth. The mission mattered.
Then, in the blink of an eye, it was over.
I spent ten years in the military myself.
My first five years began with one year at the Naval Academy Preparatory School in Newport, Rhode Island, followed by four years at the United States Naval Academy in Annapolis, Maryland. After graduation, I served five years as a Marine Corps Infantry Officer, with deployments to Afghanistan, Japan, and the Philippines, before transitioning off active duty in 2015.
I relocated to Newark, NJ, and took a job at St. Benedict’s Prep—an all-boys school in the heart of downtown Newark. I oversaw the residence hall, which allowed me to work in the evenings and start a boxing team at the school. I later spun this out into a nonprofit, IRONBOUND Boxing, in 2016.
Most vets take the safe path when reentering civilian life.
They get a job with a steady paycheck, a benefits package, and a new chain of command. For some, that works. There’s no shame in it. Some of us transition out with families and responsibilities that we can’t ignore.
But if you’re like me, you looked at the corporate ladder and saw a cage.
You couldn’t stomach the politics or the feeling that your work didn’t matter.
You didn’t survive what you survived to push buttons for a paycheck.
You didn’t lead teams under fire to become middle management.
So you did what you’ve always done when the mission demanded it.
You adapted.
You decided to build your own business with purpose and a mission that matters.
You’ve raised seed capital or self-funded your idea. You’ve built a prototype or landed your first contract. You’ve proven you can make something real. Now, you’re trying to figure out how to make people care.
You’ve done the hard part. But it’s time to scale it.
Let’s be clear: This rally cry isn’t for every vet who’s ever talked about starting a business, whether venture-backed or self-funded.
It’s for the ones already in the fight.
The ones who don’t have a marketing team or an agency on retainer yet. The ones who want actuals talking to actuals—leader to leader, not relayed through staff or middleman, with straight talk, no buzzwords.
Veteran Entrepreneurs are built different, so they’re uniquely positioned to build different businesses.
You’re a Veteran Entrepreneur if your service didn’t end when you took off the uniform.
You carry the same sense of mission into the marketplace. You see business as another form of service—measured in impact, not rank. You don’t wait for orders. You create the mission.
You share the five core values of all Veteran Entrepreneurs:
Grit
Impact
Service
Leadership
Adaptability
Money matters, but meaning and people drive the mission. You’ll go down swinging to make sure your people get paid, no matter the circumstances, whether it’s a global pandemic or otherwise. You build things that matter and make moves that count. You design new terrain. It’s how you’re wired.
If that’s you, welcome. You’re in the right place, so keep reading.
Being a Veteran Entrepreneur doesn’t make business easier. It means you’re equipped to handle the chaos better than most. You’ve been conditioned to “suffer in silence,” even when fighting battles you don’t know exist.
Let’s call them what they are.
The 5 Battles Veteran Entrepreneurs Fight
I see vets who got the grit, brains, and work ethic, but can’t get their business to move.
That doesn’t mean you’re weak or lacking in talent. It’s because you’re running the wrong playbook. The habits that kept you alive in the military can hold you back in business.
Once you spot them, you can fix them.
There is an approach that helps you redirect the discipline, problem-solving, and strategic thinking you already have toward the kind of mission entrepreneurship requires. But before I explain it, you need to understand what you’re up against.
1. You’re waging the wrong war in existing terrain.
This happens when your business is trapped competing in someone else’s category.
You’re trying to solve a problem or offer a product that directly competes with an existing business. So, you study your competitors obsessively to figure out how to be a better, faster, or cheaper version.
But the market doesn’t respond.
You know something is fundamentally wrong with your approach, but you can’t see what it is because you’re too deep in the weeds.
James Samuel knows this fight.
James is a former F-15C fighter pilot and Air Force Academy grad. After service, he built ANJEL Tech—a personal safety app that turns your smartphone into a body camera, live-stream device, and GPS locator. He launched it after George Floyd’s murder to give Black and Brown families a way to protect themselves during police encounters.
The product was solid, and the mission mattered.
But after two years of pitching universities and nonprofits, the business had limited traction and modest revenue.
Here’s how the company positioned itself:
When James brought me on as Chief Category Officer, the problem was obvious: He was fighting the wrong war.
He’d positioned ANJEL Tech as a social justice app in a saturated consumer market, competing with Life360 and other family safety apps. Buried in his business was something far more valuable. He’d built a defense-grade safety system and secured a Small Business Innovation Research (SBIR) grant to pilot it with the U.S. Air Force.
The military cared about base security and operational readiness.
Together, we reframed the battlefield:
Dropped the political language
Renamed the company to Guardian ANJEL
Repositioned it as “real-time safety technology for the DoD”
Built a company narrative around protection
It was the same product, but in a different terrain.
Today, Guardian ANJEL has contracts with four different Air Force bases and is growing. The same company that universities once ignored is now getting calls from procurement officers and generals. God willing, it will be on every military base by 2028.
Here’s how the company positions itself today:
If you’re working twice as hard as your competitors but not seeing results, you’re probably fighting the wrong war.
Don’t ask yourself: “How do I execute better?”
Ask: “Am I fighting on the right terrain?”
2. You feel like a misfit.
You left the military thinking your skills would translate, but the civilian business world doesn’t have the perfect place for you.
You’re too creative for traditional operations roles and too operational for creative work. You don’t fit the Silicon Valley founder archetype. You’re not interested in playing the networking game. You can’t stomach corporate politics or the emptiness of work that doesn’t matter.
Your soul is hurting because you went from leading missions that mattered to pushing products nobody cares about.
You thought entrepreneurship would give you purpose again.
Instead, you feel more lost than ever.
I know this fight intimately.
After 10 years in the military and transitioning out in 2015, I spent years trying to figure out where I fit. I taught boxing classes in New York City, training CEOs one-on-one and running group classes. I also ran a nonprofit gym in Newark, which I wasn’t taking a salary from.
It wasn’t the Marine Corps, but I had a purpose and was serving people.
Then the pandemic hit.
Overnight, there was no market need for in-person boxing. When they canceled the NBA, I knew it was over for me. My income disappeared. I was down on the canvas, literally and figuratively, in my one-bedroom apartment, staring at the ceiling, wondering what the hell I was supposed to do next.
Then I got a call from a West Point grad who said, “Mike, get back in the fight.”
That’s the day I started calling myself IRON Mike.
I was in that apartment with nothing but a laptop and a microphone. I’d taught myself how to podcast earlier, so I said, “I’m going to spin something out of this.” No one was coming to save me. There were no guarantees. Some people spent the pandemic learning new skills. Some sat around eating Chipotle and watching Netflix.
I took a business from zero to one with a laptop and a microphone.
Feeling like a misfit is a feature, not a bug.
Going through that time under tension gave me the conviction that maybe, just maybe, I could be a successful entrepreneur. The young me would have never believed it. Sometimes you have to go through the heat, come out on the other side, and realize you’re stronger than you think.
If you feel like you don’t fit into existing boxes, it’s because you’re built to create new ones.
That misfit feeling doesn’t go away, but you can redirect it toward something worth building.
3. You’re carrying too much weight.
As a vet, you’re wired to be an operator, to get the mission done, and to carry the load yourself.
In combat, that made you exceptional. You could carry a 100-pound ruck for miles, execute the mission, and bring your team home. When things got hard, you just carried more weight.
In business, trying to carry everything yourself doesn’t make you strong—it makes you slow.
You can build the product. You can close the deals. You can will the company forward through sheer effort. But if you’re the only one who can tell the story, you’re carrying weight that should be distributed across your team.
You can’t carry the weight of your business alone.
When you haven’t taken the time to articulate what you’re building—clearly, repeatedly, in a way others can understand and run with—you become the bottleneck. Your team can’t sell. Your investors can’t evangelize. Your employees can’t execute with confidence because they don’t fully understand the mission.
You’re rucking alone when you should be leading a formation.
Paul Lwin, founder of Havoc AI, was carrying too much weight for his company.
Paul is a U.S. Navy, NFO, and Test Pilot School Graduate who wanted to prevent conflict in the Pacific. He founded Havoc AI to build autonomous surface vessels (USVs) for the Department of Defense.
The company was flying. His team built 12 USVs in eight months. They raised $11 million in SEED capital. Paul was closing deals and getting attention.
But Paul was doing most of the selling.
He could tell the story. He understood what Havoc AI was building. So, when people asked his team, “What does Havoc AI do?” the answer was unclear.
Were they building boats? A technology platform?
The technology was revolutionary, but the team struggled to effectively articulate it.
He knew he was building a new category.
He could feel it. But he hadn’t taken the time to define it, name it, and align his team around it. So he became the single point of failure, the only person who could effectively communicate the vision.
He was stuck in operator mode: executing flawlessly, carrying the weight himself, but unable to distribute the load across his team.
The first thing I noticed when helping with Havoc AI’s category strategy was that they weren’t building boats.
They were building the first scalable autonomy platform for maritime defense—a system that could coordinate thousands of vessels simultaneously, while communicating and collaborating in real time.
We articulated a new POV: “Collaborative Autonomy.”
That phrase became the unlock. It was the strategic frame that gave the entire team a shared language. Suddenly, Paul wasn’t carrying the weight alone:
The product team knew they were building the platform, not perfecting individual boats.
The investor pitch positioned Havoc AI as a category creator, not a boat manufacturer.
The sales team could articulate the vision without Paul in the room.
Recruiting became easier because the mission was clear.
Since locking in that clarity, HavocAI raised $85 million and solidified its path to unicorn status.
Not because the tech changed. Because Paul stopped carrying the entire mission alone. He took time to create the clarity that allowed his team to carry it with him.
You can’t scale what you can’t distribute.
In combat, you sometimes had to carry the weight yourself. In business, if you’re carrying it alone, you’re doing it wrong.
Building a category takes time. It takes thinking. It takes articulating your vision clearly enough that someone who’s never heard of you can repeat it back. Once you do it, you unlock scale.
Your team can carry the mission forward with you.
4. You know you’re capable but can’t get traction.
You’ve led teams in combat, but you can’t stand out in the market—and it kills you inside.
You solve real problems, but you can’t articulate your value in a way that makes customers say “hell yes!” You need to learn how to identify markets, communicate your value, understand what customers actually want, and get them to buy.
You have the discipline and resilience (you’ve proven that a thousand times over), but you don’t have a framework that works for the kind of business you want to build. You know you’re solving a unique problem, with a unique point of view, but you struggle to stand out.
You don’t need generic business advice or a “translate your military skills” workshop. You need a system designed for people like you: mission-driven, operationally minded, willing to do the work, but stuck fighting for your company’s life.
The skills that kept you alive in combat don’t map cleanly to the skills required to build a business. So, the gap between what you know and what you need to know keeps growing.
Tim Hsia fought this battle when founding Context VC.
Tim is a West Point graduate, combat veteran, and seasoned entrepreneur. When he started Context Ventures in 2021, he had everything on paper: the pedigree, the network, the track record, the capital to deploy. But he knew venture capital was a saturated market.
Hundreds of VC firms competed to attract the best founders. Most VCs pitch the same generic line: “We invest in great founders building big markets.” In other words, they’re selling money. And the market has plenty of that.
Tim had already figured out his edge.
He’d led soldiers in combat. He’d bootstrapped multiple seven-figure businesses. He was passionate about veteran-led startups and understood the founders in a way that traditional VCs never could. So, Tim decided not to compete with Andreessen Horowitz or Sequoia. Instead, he chose to back veteran-led startups at the pre-seed stage—what he calls “inception capital.” Friends, family, and fools. No pitch deck, no product, no revenue, no problem.
Most VCs won’t touch founders at that stage.
But Tim knew elite military operators are built different. They’ve been tested under fire. They know how to execute under impossible conditions. They can handle the chaos of zero-to-one better than most Stanford grads with a pitch deck.
Tim also had a vision for how Context should feel. He told me, “I think of us like X-Men. I’m Professor Xavier. Our network is Cerebro. We find exceptional veteran founders before anyone else knows their names.”
The problem was clarifying that vision.
Tim knew what he was building. He just hadn’t taken the time to articulate it, name it, and package it in a way his team, his LPs, and his founders could run with.
When Tim brought me into Context as a Venture Partner, it was already a solid early-stage VC fund with a smart team, good founders, and deal flow. He had a vision, but he had never formally articulated it to his team or the public.
Together, we turned Tim’s X-Men metaphor into a POV:
The X-Men Thesis is the belief that the world doesn’t need more founders. It needs more X-Men—elite military veteran operators who build what others can’t even see yet.
With that POV, everything clicked.
LPs understood the differentiation immediately: “You’re not competing with Sequoia. You’re creating a new category.”
Veteran founders knew Context was built for them: “Finally, a fund that gets us.”
The pitch became clear: “We don’t invest in pitch decks. We invest in people who’ve already been tested under fire.”
Tim had the capability all along. He just needed the framework to articulate it clearly.
Today, Context Ventures is the category leader in inception capital for veteran founders—backing exceptional military operators at the pre-seed stage.
That’s the battle. You’re not lacking talent, work ethic, or potential. You’re lacking the system to turn what you know into something the market can understand and buy.
5. You’re leaving extraordinary value on the table.
Veterans own 1.6 million firms in the U.S., employing 3.3 million people and generating $922 billion in revenue annually.
These aren’t lifestyle businesses or side hustles. By any measure, veterans are a powerful entrepreneurial force in the American economy. Too many people write us off as damaged goods instead of recognizing the fight we bring to the business world.
(There was a moment when civilians thought “Veteran Entrepreneur” meant primarily t-shirt, coffee, and alcohol brands.)
But the stats don’t reveal:
Whether businesses are truly thriving versus merely surviving
Which founders are working twice as hard as their competitors for half the margin
How many are trapped in commoditized markets, competing on price instead of value
The number of Veteran Entrepreneurs who lie awake at night wondering why their discipline, problem-solving abilities, and willingness to outwork everyone else don’t matter in the market
Veteran Entrepreneurs are a valuable part of the economy, but we often fail in business because we apply exceptional execution to the wrong strategy. We compete in categories that have already been won by someone else. We try to be better when the market rewards being different.
You can’t bring a tactical mindset to a strategic problem.
If you’re losing in business without firing a shot, it’s because nobody taught you there’s a different way to fight.
In the summer of 2021, Haley Marie McClain Hill—former Air Force officer and NFL cheerleader—overslept for work. As she tugged off a civilian bodysuit to put on her uniform, she thought, “Why doesn’t something like this exist for women in the military?”
That question became a business.
Within days, she created a new category of athleisure built for women who serve.
Where Nike and Under Armor design for the masses, TORCH Warriorwear designs for a minority—women in uniform who want to feel confident, feminine, and strong. Since launching, TORCH has generated more than $1.3M in revenue, grown fast, and even landed Haley on Shark Tank in 2024. She bootstrapped everything herself. No outside funding. Just vision, grit, and a mission to prove that service and style can coexist.
Her company is still young, but she created net-new demand and built a category around it. Haley didn’t compete with anyone. She created a space that didn’t exist before.
This is a fundamentally different approach to business.
It’s essential for all Veteran Entrepreneurs, including those who went to elite schools like Stanford, Harvard, or Wharton.
The marketplace doesn’t care about your pedigree, your rank, or the fact that you’ve been through things most people can’t imagine. It doesn’t consider that you led a platoon in Ramadi or Sangin, or that you landed Jets & Helicopters on an Aircraft Carrier in the Persian Gulf. It doesn’t want to know that you planned complex operations with zero margin for error.
The market only responds to value it didn’t know it needed, delivered by people brave enough to create new categories instead of competing in existing ones.
You’ve already learned about many legendary Veteran Entrepreneurs who’ve proven this strategy works. Here are a few more:
FedEx: Fred Smith (Marine) didn’t try to compete in the shipping industry. He created overnight delivery, a category that didn’t exist until he invented it.
Talea Beer Co.: LeAnn Darland (Navy) didn’t compete in craft beer. She created hospitality-forward, female-friendly craft beer experiences, changing who belongs in the category.
Nike: Phil Knight (Army) didn’t compete in athletic shoes. He created the athletic lifestyle category, turning sneakers into culture.
Black Enterprise Magazine: Earl Graves (Army) didn’t compete in business media. He created business media for Black entrepreneurs, by Black entrepreneurs.
GoDaddy: Bob Parsons (Marine) didn’t compete in tech services. He created mass-market domain registration, making the internet accessible to everyone.
GORUCK: Jason McCarthy (Special Forces) didn’t compete in backpacks. He created rucking as a lifestyle category, building a movement instead of a product.
Each of them understood The Law of Category by Al Reis and Jack Trout in their book The 22 Immutable Laws of Marketing, which states: “If you can’t be first in a category, set up a new one you can be first in.”
None of them tried to be the best. They chose to be different and created categories where they could be kings. They made competition irrelevant by designing entirely new terrain.
You can do the same.
You have everything those founders had: discipline, problem-solving, leadership under pressure, and the ability to execute in chaos. You’ve been tested in ways most entrepreneurs never will be.
So, why are you stuck?
These five battles exist because you carry the conditioning from your military service. This traps you in a competitive mindset. Once you understand what parts of this conditioning no longer serve you, you can drop them. You’re left with only what’s necessary to grow your business.
Let’s break it down.
The Military Training Trap
In the military, you’re trained to operate within established frameworks.
Doctrine
Chain of command
Defined mission parameters
Standard Operating Procedures
This conditioning turns you into a world-class operator who can execute under impossible conditions. It also hardwires habits into your brain that don’t translate to entrepreneurship. And in some cases, actively undermines your success.
It’s the residue of training that served you in one context but fails you in another.
The Military Training Trap affects Veteran Entrepreneurs in four ways:
1. Competing instead of creating
You’re wired to see every market as a battlefield where the mission is to outperform the enemy. You study their movements and exploit their weaknesses. You execute better, faster, and more precisely. That mindset wins firefights.
But in business, the best competitors rarely win.
Category creators do.
Category creators design entirely new terrain by solving problems no one else is solving. They ask, ‘What battle should we be fighting that doesn’t exist yet?’ They set the rules of engagement and make competition irrelevant by being the only player in a space they invented.
You’ve been conditioned to compete when you need to create, and that is a fundamentally different mission requiring fundamentally different strategies.
2. Perfectionism that kills momentum
In combat, mistakes cost lives.
You were trained to eliminate error, to triple-check everything, to ensure mission success before execution. That’s not just good practice—it’s survival. For you, and for your team.
But in business, perfectionism is a death sentence.
The market rewards speed and iteration. Perfect is too late. And while you’re polishing, your competitors are learning. They’re not smarter or more capable than you. They’re just willing to ship messy work, learn from real customers, and iterate in public.
Meanwhile, you’re still perfecting the product, the pitch deck, the website. You’re waiting for some imaginary standard of “ready” that never comes. You won’t launch because it’s not flawless, which means you never launch at all.
The solution is to redirect your perfectionism.
Maintain your personal standard for discipline and follow-through. But ship version 1.0, get real customer feedback, and iterate based on what the market actually wants, not what you think it should want.
3. Waiting for orders instead of taking initiative
You were trained to execute the mission, not design it.
Someone higher up the chain determined the objective, allocated resources, and gave you parameters. Your job was to make it happen with excellence. That created a subtle but powerful habit: looking for the “right” way to do things. Waiting for someone to tell you the proven path. Seeking the playbook, the framework, the doctrine.
Entrepreneurship doesn’t have a manual.
Nobody is coming to give you orders. The market doesn’t care what you’re waiting for. And while you’re looking for permission, your competitors are moving.
The solution is to operate from Commander’s Intent, not Standard Operating Procedures.
In the military, Commander’s Intent gives you the “why” and the end state, then trusts you to figure out the “how.” Apply that to your business: Define your strategic objective clearly, then give yourself permission to find your own path to achieve it.
There is no doctrine for entrepreneurship. There’s only experimentation, feedback, and adaptation. You already know how to operate with autonomy in uncertain environments.
You just need to execute on the mission.
4. Risk aversion that masquerades as wisdom
Calculated risk-taking is critical in combat because recklessness gets people killed.
You learned to assess threats, minimize exposure, and avoid unnecessary chances. Your nervous system was trained to treat failure as catastrophic. That kept you alive.
In business, failure isn’t life-or-death. It’s data.
Every failed experiment teaches you something the market needs you to know. Every mistake is feedback. But your body doesn’t know the difference. So when you face business decisions that require risk—shipping before you’re ready, charging what you’re worth, pivoting when the data says pivot—your nervous system screams danger.
You freeze. You overthink. You avoid making moves that could be “wrong.”
As a result, the business stalls.
The solution is to distinguish between reversible and irreversible decisions.
In combat, most decisions are irreversible. You can’t undo a casualty or retry a mission. But most business decisions are reversible.
You can change your pricing.
You can pivot your product.
You can rewrite your positioning.
You can undo almost everything except inaction.
Amazon’s Jeff Bezos calls these “two-way door decisions.” You can walk back through if it doesn’t work. The way to do it is to assess risk the way you were trained: Identify the threat, determine the probability, and calculate the potential loss. But recalibrate your scale. The worst case is usually “we learn something and try again.”
The only irreversible decision in business is not making one at all.
These four conditioning patterns (competing, perfectionism, waiting, and risk aversion) are the Military Training Trap.
The Military Training Trap is bad enough on its own. But it becomes a prison when it fuses with ego—the belief that your past achievements should guarantee future success, that your pedigree should open doors, that grit alone will overcome strategic misalignment.
Ego hits veterans differently than other entrepreneurs.
We’re taught to suffer in silence. Asking for help feels like weakness, and admitting you don’t know something feels like failure. So instead of pivoting when the market tells you to, you dig in. You double down. You convince yourself that if you just work harder, push longer, refuse to quit…you’ll break through.
This creates a sunk cost fallacy that kills businesses.
You won’t pivot or shut it down, even when there’s no market, no revenue, no traction. Why? Because you feel like you only get one shot at the plate. You’d rather be right than be an entrepreneur. You’d rather prove you could do it than actually do it.
Business is an infinite game, not a single mission.
In combat, you got one shot. The plan had to work. Failure wasn’t an option. In business, you get infinite shots. The first plan almost never works. Failure is feedback, and pivoting is adapting.
Too many Veteran Entrepreneurs don’t see it that way. We see pivoting as admitting defeat. We see asking for help as showing weakness. We see changing course as failing the mission.
That’s ego talking, and it’s the heaviest thing you carry.
In business, ego shows up in several deadly forms.
Pedigree Ego is the belief that your resume should open doors.
The belief that your resume should open doors is insidious because it feels justified.
You earned those credentials. You were a SEAL, a Ranger, a Marine. Maybe you went to a Service Academy or an Elite Business School. You led teams, earned medals, and accomplished things most people never will.
But the market doesn’t care about what you’ve done.
It cares about what you can do next.
Pedigree ego makes you lean on your background instead of building new value. It makes you tell your origin story when you should be telling your customer’s transformation story. It makes you wait for investors to recognize your potential when you should be proving it. It makes you expect doors to open that won’t open.
Your pedigree might get you a meeting, but it won’t close a deal.
Clinging to it keeps you from doing the unglamorous work of proving value every single day.
Your credibility is a starting point, not a destination. Use it to open doors, then prove value every single day through results, not a résumé.
Customers don’t care that you can ruck 50 miles or that you graduated top of your class. They care whether you can solve their problem better than anyone else. So, stop introducing yourself as a former pilot, team member, or Marine. Start by introducing yourself with the problem you solve. Or better yet, who you aspire to be. Let the world know what you want to be known for.
Show people the potential of what you can build.
Operational Ego is the belief that superior execution guarantees success.
You know how to build systems and run processes. You know how to take a complex operation and break it down into repeatable, scalable steps. You believe that if you just execute well enough, you’ll win.
Perfect execution of the wrong strategy is still failure.
You can’t operationalize your way to success in a market that doesn’t want what you’re selling. You tell yourself, “I just need to tweak the system.” But what you actually need is to stop fighting the wrong battle and design a different one. The market rewards the company that creates a new category and solves a high-value problem.
Operations is a tool. Use it when the strategy is sound and the market is responding.
Don’t use it to force a bad idea into existence. Learn to recognize when operations become self-destruction. The strongest thing you can do sometimes is stop, assess, and change direction.
That’s wisdom, not weakness.
Perfectionist Ego is the belief that excellence requires flawlessness.
You were trained that “good enough” gets people killed. Standards exist for a reason. You carry that into business, refusing to ship anything that isn’t perfect.
You tell yourself it’s about professionalism, maintaining standards, respecting your customers.
Really, it’s about fear.
Fear of judgment. Fear of looking incompetent. Fear of putting something into the world that might fail. Perfectionist ego tells you that messy work reflects poorly on you, that iteration is for amateurs, that real professionals get it right the first time.
But business isn’t combat. Shipping a flawed product doesn’t cost lives, it generates feedback.
Done and shipped beats perfect and stuck.
Business is a reps game. You learn more from shipping a flawed product to ten real customers than from spending six more months polishing it in isolation. Keep your standards—that’s part of what makes you excellent—but apply them strategically, not universally. Don’t let them be an unnecessary cage.
Ship a “good enough” version. Get feedback. Iterate in public. Learn fast.
Perfect later, if ever.
The market rewards speed, adaptation, and the courage to put imperfect work into the world. This goes for not only your product, but also your marketing and thought leadership pieces. You can’t be a good writer if you don’t publish.
Your perfectionist ego is costing you the one thing you can’t get back: time.
Resiliency Ego is the belief that grit conquers all.
You survived BUD/S, Ranger School, Selection, and combat deployments. You’ve proven you can endure anything, and you think resilience will carry you through business. You’ll eventually break through if you work harder, push longer, and refuse to quit.
Grit doesn’t create demand.
Willpower doesn’t fix strategy.
You can’t outwork a market that doesn’t want what you’re selling.
As veterans, we hate giving up. We hate quitting. That makes us dangerous in combat but stubborn in business. We grind away at ventures that should have pivoted or been shut down months or years ago, burning time and capital on ideas the market has already rejected, confusing persistence with wisdom.
Resiliency ego tells us that quitting is a weakness.
Sometimes the strongest thing you can do is take a knee.
You can escape the Military Training Trap and drop the ego you carry.
But you can’t stop there. You can’t walk away empty-handed, ready to build your business. You have to reload with what serves your next mission.
Here’s how I did this for myself and for every Veteran Entrepreneur I’ve worked with.
The Rucksack Reset
In the military, your rucksack is life.
Every ounce matters: ounces equal pounds, and pounds equal pain. On a long movement, dead weight slows you down, exhausts you, and compromises the mission. So you become ruthless about what goes in the ruck.
You carry only what helps you complete the mission. Everything else gets left behind.
Business works the same way. But most Veteran Entrepreneurs pack their entrepreneurial rucksack with dead weight: habits that no longer serve you, beliefs that worked in one context but fail in another, identities that anchor you to the past instead of propelling you forward.
The Rucksack Reset gives you freedom through subtraction.
It happens in two steps:
Drop the dead weight.
Keep only the mission-critical gear.
This isn’t a rejection of your military service or pretending it didn’t matter. It’s honoring your service by refusing to let it become a burden. It’s acknowledging some of what made you excellent in the service will make you mediocre at business—unless you’re willing to drop it.
Here’s how to reset.
Step 1: Reframe your military identity.
I know this is easier said than done.
The belief that “being a SEAL” or “being a Marine” is who you are is the first thing you need to reframe. It’s also the hardest. Because that identity cost you something. You earned it through suffering, sacrifice, and selection.
It defined you for years, maybe decades.
Letting go feels like betrayal and dishonoring what you built.
But the more you lean into your future self, the stronger the category you can create.
The skills you earned are life-long tools in your kit. But the identity itself keeps you tethered to a version of yourself that no longer exists. It makes you market yourself as “the SEAL consultant” instead of the person who solves a specific problem better than anyone else. It expects the market to care about your rank when it only cares about outcomes.
All Veteran Entrepreneurs grapple with identity.
Fellow Veteran Kevin Seiff, a Navy SEAL turned entrepreneur, said it best in a LinkedIn post:
“It took a long time to separate my identity from being a Team Guy. I was forced to realize the unfortunate reality that being a SEAL wasn’t who I was—no matter how much time I spent perfecting those skills. I am me. A Special Operator was simply what I did.”
Read that again. I know it took incredible courage for him to write it, let alone share it publicly.
Your rank, your title, and your job reflect what you did, not who you are.
Too many Veteran Entrepreneurs struggle with that separation. So you try to be a SEAL in the business world, a Marine in the marketplace, a Ranger in revenue operations. You cling to the identity because letting go feels like dishonoring the sacrifice.
The thing you worked hardest to become no longer defines you.
This is where ego becomes an unbearable weight.
As long as your self-worth is tied to who you were instead of who you’re becoming, you’ll always feel out of place. Kevin (the baker from above) now teaches veteran entrepreneurship and runs Crafted Coastal Bakery, a sourdough bakery based in Encinitas, California, with his wife Kristen. He said, “I’m comfortable in my masculinity and rock an apron to work.”
That’s not a rejection of his SEAL identity. That’s freedom to become a new version of himself. His value is in doing work that gives him purpose.
Earl Graves also figured this out.
After serving in the Army as a Green Beret, he didn’t build his business by leading with “Army vet Earl Graves.”
He built Black Enterprise Magazine, one of the largest and most successful minority business publications of its era, by identifying a problem nobody else was solving: Black professionals and entrepreneurs had no business media designed specifically for them, and by them.
Earl could have made his veteran status central to his brand, emphasizing it every chance he got. Instead, he became known for the category he created and the community he served. His military experience shaped his discipline and work ethic, but it didn’t define his business identity.
He became Earl Graves, founder and publisher.
(He’s more known for his elaborate mutton chops than his time in the Army.)
Your service gave you tools, and your identity as a Veteran Entrepreneur is how you use them.
Step 2: Keep the mission-critical gear.
The Rucksack Reset is designed to let go of what no longer serves you.
When you drop your identity and ego, you have room for the skills and traits that will help you design categories and build businesses that win.
Keep the discipline. The ability to do hard things consistently, even when you don’t feel like it, is yours. It’s not going anywhere. The difference is how you apply it.
In the military, discipline meant following SOPs, maintaining standards, and executing the mission as designed.
In business, discipline means showing up every day to do the work nobody sees. The 20 customer calls, the unglamorous iteration, the daily writing, and the relentless focus on the one thing that moves the needle.
Discipline isn’t rigidity. It’s consistency in service of the mission.
Keep the problem-solving. The creativity to find solutions under constraints, to make decisions with incomplete information, and to adapt when the plan falls apart is one of your greatest assets.
Veterans are exceptional at this because you’ve done it under the most extreme conditions. The shift is applying your problem-solving to strategic challenges, not just operational ones. Don’t just solve “how do we execute better.”
Solve “Are we fighting the right battle in the first place?”
Keep the adaptability. The willingness to change tactics when the mission demands it is critical. You learned this in service: no plan survives contact with the enemy. In business, no strategy survives contact with the market.
The companies that win are willing to change course fastest when the market gives them feedback.
Keep the mission focus. The ability to know what matters and ignore what doesn’t is rare. Most entrepreneurs get distracted by every shiny tactic, every new trend, every competitor’s move. You’ve been trained to maintain focus under chaos. Use that.
Define your mission with clarity. Then ignore everything that doesn’t serve it.
Say no to opportunities that dilute your focus. Say no to tactics that don’t move the primary objective. Mission focus is your competitive advantage.
Keep the leadership. The ability to inspire and align people around a vision, to build trust under pressure, to make hard calls when nobody else will—that matters in business as much as it mattered in service.
The shift is understanding that leadership in business isn’t about rank or authority. It’s about influence, trust, and the ability to articulate a future worth building. You don’t lead through command.
You lead through clarity, conviction, and the willingness to go first.
Zack Keller and Priscilla Pesci did the Rucksack Reset for Thrival Energy.
Thrival Energy was founded by Priscilla Pesci—a serial entrepreneur, investor, and Media executive—and Zack Keller, a former U.S. Navy SEAL turned innovation specialist. The goal was to bring a dense alternative to sugar-packed bars, energy drinks, and caffeine (without the crash) for the military and first responder community.
The connection between poor nutrition and rising rates of burnout, anxiety, and depression was clear and ignored.
They launched “Apex Performance Fuel” targeting cyclists, swimmers, and the fitness crowd. But the market didn’t respond. Unfortunately, when they soft-launched in 2022-2023, it was apparent the brand was conflicted.
On one hand, they wanted to go after the military and the first responder community.
On the other hand, their category and visual brand identity featured cyclists, swimmers, and other elite athletes.
The disconnect threatened to make Thrival another “me too” nutrition brand in a sea of entrenched competition.
While helping Zack and Priscilla think through their category strategy, it became apparent that they wanted to create a replacement for the MRE (Meals Ready to Eat), the standard-issue nutrition pack given to those in combat. We said, “Wouldn’t it be great if instead of packing MREs in your pack, you could throw in a couple packs of Thrival?”
I asked Zack one question:
“Who are you really fueling?”
He paused, then said:
“Honestly? The people who have to stay ready. Soldiers. Firefighters. First responders.”
That’s all I needed to hear.
We repositioned everything around that one truth. We dropped the gym talk and reframed the brand as “Readiness Nutrition”—fuel for the mission, not the mirror. Packaging, copy, and visuals all changed. Once we started talking to the right people in the right language, the brand began to click.
We stopped trying to be the next RXBAR and became the first Thrival.
With a strong category and a better understanding of where to play and how to win, Thrival is still in the process of rebranding. They’re expected to re-engage with another soft launch, built around the “Readiness Nutrition” in January 2026.
The Rucksack Reset builds your business with precision.
It helps you unpack the habits, identities, and beliefs that no longer serve your mission as a Veteran Entrepreneur. A heavy ruck makes you slow. A light and purposeful ruck makes you lethal.
Once you’ve done the reset work, you’re ready to execute. The FIRE Plan is a strategic approach to help your business move light, fast, and with purpose.
Here’s how it works and why it helps you win.
The FIRE Plan: How to Coordinate, Aim, and Win Your Market
In the military, a FIRE Plan is a continuous process of synchronizing and integrating all available fire support assets—such as artillery, air support, and naval guns—with a unit’s maneuver plan to achieve specific objectives.
You make sure every move, every unit, every action lands where it’s supposed to.
Business is no different.
For a former grunt like me, this translates to “setting conditions” for the main effort: sales.
Most Veteran Entrepreneurs struggle in business because they failed to set conditions.
They launched without doing the necessary grunt work ahead of time.
They fell into the Military Training Trap and built a business before identifying the correct category for their product.
They didn’t align their team with clear and consistent messaging.
They avoid talking to customers until it’s too late. As a result, they’re building blind.
They have zero clarity on where the battlefield is, who the real enemy is, or what the mission actually demands.
The FIRE Plan framework fixes that.
It’s the same system I use with every client—from defense-tech founders raising Series A rounds to veteran-led startups working for their first million in revenue. Each phase turns what you already know (clarity, communication, coordination, execution) into a new kind of mission: building a business that wins by design, not by accident.
Here’s how to run the play:
Phase 1: Frame – Clarify your battlefield, so you know what category to create or reframe.
Phase 2: Identify – Choose your perfect target customer and beachhead market.
Phase 3: Rally – Align your point of view, so your team can rally behind it.
Phase 4: Execute – Fire and adjust your go-to-market plan for your target.
Each phase builds on the one before it. By the end, you’ll have a clear mission, a focused market, an aligned team, and the discipline to execute fast.
Let’s get into it.
Phase 1: FRAME – Clarify the Category Battlefield
Most veteran entrepreneurs build their business the same way they planned missions: gather intel, study the enemy, and get ready to out-execute everyone around them.
That works in combat.
In business, it gets you killed. Because this battlefield isn’t about geography. It’s about perception. You can have the best team, tech, and intent, and still lose because you’re fighting on the wrong terrain, which often means choosing the wrong category and customer segment.
If you’re not number one (at the very least, number two) in your category, you’ve already lost.
VetraFi: Clarifying the Battlefield
Each year, between 150,000 and 200,000 service members join the military.
Unfortunately, about 15% to 20% of new recruits are underbanked—they lack access to mainstream financial services and rely on alternatives like payday lenders or check cashers. Many are digital natives (millennials and Gen Z) who’ve never physically touched money. They keep their funds in fintech products like Cash App or Zelle.
This demographic represents an underserved opportunity for a new type of neobank for today’s service members.
VetraFi is a digital-first military banking startup that emerged from Context Ventures’ venture studio. By the time I got brought on as an advisor in the summer of 2025, VetraFi’s co-founders and Context’s GP, Tim Hsia, described VetraFi as “Chime for the military.”
The category designer in me cringed when I heard this.
I knew by describing VetraFi that way, the company instantly trapped itself in a comparison game with a product and category it didn’t create.
Chime is a U.S. neobank founded in 2012, aimed at offering fee-free banking for everyday Americans. Positioning VetraFi as “Chime for the military” put them up against a multi-billion-dollar fintech and legacy military banks like USAA and Navy Federal. These are giant companies with decades of experience, billions in assets, and tens of thousands of employees.
Competing head-to-head meant suicide, especially going from zero to one.
“Not only would that put us up against Chime, a multi-billion-dollar fintech,” I said. “But it’s also a great way to get buried by USAA and the Old Guard of military banking.”
I challenged the VetraFi team to find and exploit a gap in the terrain. A niche in the market we could own. A category shift everyone else ignored.
The Frame phase is about considering your terrain, knowing your threat, and deciding what kind of business you want to build.
Are you going to be the best? Be better? Or be different?
You can do this by asking yourself:
Where do I have an unfair tactical advantage? (Background, connections, etc)
What adjacent opportunities am I not paying attention to?
Where is the demand signal coming from currently in the form of revenue?
If you skip that step, you risk fighting with the wrong weapons, in the wrong place, for the wrong prize. Frame the battlefield first. You’ll spot opportunities that everyone else is too busy executing to see.
Only then are you ready for what’s next.
Phase 2: IDENTIFY – Choose Your Target Customers
Once you’ve framed the battlefield, your next mission is to identify your ideal customers.
You don’t want to boil the ocean, spreading yourself too thin by trying to do too much too soon. You need to focus your efforts where it matters most. This includes selecting a beachhead category and customer—a narrowly defined, high-leverage segment where you establish dominance first.
Most founders mistakenly use the spray and pray approach.
They do a bunch of random acts of marketing and sales activity because they don’t know who their perfect customer is, let alone how to differentiate themselves. They try to sell to everyone: “the military,” “veterans,” or “anyone who trains hard.” That’s not a market. That’s just noise.
In combat, focus keeps you alive.
In business, focus keeps you funded with capital from customers and investors.
VetraFi: Identifying the Target
Instead of fighting head-to-head with USAA and Chime, I encouraged the VetraFi team to find a gap in the terrain.
We landed on: The Digital Native Service Member—particularly junior enlisted (E1-E3) and the soon-to-serve segment.
A digital native service member is someone who grew up on smartphones, social media, and the 24/7 internet. They have a fundamentally different relationship with technology that many of the “Old Guard” military banks fail to cater to.
This segment includes:
1.3 million active-duty service members
750,000+ reserve and National Guard personnel who are constantly moving, underbanked, and underserved by legacy systems built for retirees and officers
550,000–700,000 junior enlisted troops (E1–E4), the group most vulnerable to financial stress
150,000–200,000 soon-to-serve recruits entering the force each year
They don’t just need a bank.
They need a financial system that leverages the benefits of AI, is mobile-friendly, and is purpose-built for those who serve. Digital Native Service Members interact with money the way they interact with Cash App, Venmo, and Zelle—instantly, digitally, seamlessly.
With the target in mind, we reframed VetraFi’s product design, messaging, and investor pitch.
VetraFi put itself on a path to category domination the moment it stopped trying to be “better” and started being different. Today, VetraFi has closed its SEED round. With the category and capital behind us, VetraFi is positioned to launch in 2026 and create a new era of military banking.
The Identify phase is about finding existing demand, then figuring out a way to redirect it toward you:
Who feels the pain most acutely?
Who can pay for the solution now?
Whose problem will prove your category right?
Precision is liberating, not limiting. When you focus on the right target, the noise fades.
Phase 3: RALLY – Align Your Point of View
Once you’ve framed the battlefield and locked in on your target, it’s time to rally the troops around a clear point of view.
Here’s the mistake I see over and over again: Founders skip straight to tactics.
They start building the product, creating the pitch deck, and designing the website. The don’t first align the team around why this category needs to exist and what’s fundamentally broken about the status quo.
In the military, clarity doesn’t trickle down. You’ve got to issue the order, repeat it, and make sure every squad knows exactly what “right” looks like. In the Marines, this is commonly referred to as “Commander’s Intent”—a clear, concise statement that defines the desired end state of a mission (the “what” and “why”) so everyone acts decisively even when the plan falls apart.
In business, this is your Point of View (POV).
Your POV is your company’s thesis about the world:
What’s broken about the way things work today?
Why is now the time for something different?
What future are you trying to create?
If your team can’t articulate your POV the same way you do, you don’t have alignment. You have cross-fire.
VetraFi: Developing the Point of View
Once we identified the Digital Native Service Member as VetraFi’s target, we had to answer a harder question: Why does this category need to exist?
Not why is it a good business idea? Or why can we make money? But why is the status quo fundamentally broken for this customer?
The team gathered to map out the terrain. Here’s what we saw:
The Old Guard (USAA, Navy Federal) was built for a different era.
Branch-first, not mobile-first
Designed for officers and retirees, not junior enlisted
Built on legacy infrastructure that can’t move at the speed of fintech
Digital Native Service Members have a fundamentally different relationship with money.
They grew up on Cash App, Venmo, and Zelle that’s instant, seamless, mobile
Many have never physically touched money or a bank card, let alone walked into a branch
15-20% are underbanked, relying on payday lenders and check cashers because legacy banks don’t serve them
Military banking is stuck in the past while the force moves into the future.
That became VetraFi’s POV: You already earned it. Now it’s time to keep it.
This aligned every decision:
Product team: Build mobile-first, AI-powered financial tools that meet digital natives where they are
Marketing team: Speak to junior enlisted and soon-to-serve recruits in their language, not the language of retirees
Investor pitch: Position VetraFi as the category leader redefining military banking for a new era
Recruiting: Attract talent who believe the old way is broken and want to build the future
Once the POV was locked, we translated it into a rally cry the entire team could repeat: “At VetraFi, we’re building the premier AI-Native banking platform for the U.S. military—those who serve, those who’ve served, and the families who stand beside them.” That phrase became the through-line. Every deck, demo, and conversation laddered up to that idea.
Since then, VetraFi closed its SEED round and is now building toward launch.
Not because the tech changed, but because the POV did.
Most founders skip the POV phase because it feels abstract.
They want to execute by building the product, running ads, and closing deals.
When you skip POV, your team builds features that don’t align with the category. Your messaging feels generic because it’s not anchored to a belief. You can’t articulate why customers should choose you over the competition.
A strong POV is:
Clear: Anyone on the team can repeat it. This aligns your team around a shared belief about what needs to change.
Defensible: It’s backed by market insight, not just opinion. This differentiates your positioning by staking a claim about the future.
Provocative: It challenges the status quo, not just incremental improvement. This attracts evangelists like customers, investors, and employees who believe what you believe.
When everyone is on the same frequency, everything accelerates. The mission gets lighter. Decisions get faster. You move as one.
To build your POV, pull your team into the war room and map out the terrain.
What’s broken about the way things work today?
What does the incumbent get wrong?
What customer pain are they ignoring or underserving?
Why is now the time for something different?
What’s changed in the market, technology, or customer behavior?
Why couldn’t this category exist five years ago?
What future are you trying to create?
What does the world look like if you win?
How is it fundamentally different from today?
Once you have your POV, you want to translate it into a single phrase rally cry that captures the essence of what you’re building and why it matters. Then repeat it. Over and over. In every deck, demo, pitch, and internal meeting.
Rally your forces. Get your people, partners, and investors speaking the same language.
This is where you turn your category positioning into a story that makes people give a damn. You explain the problem you see, why the old way is broken, and why now is the time for something different. Then, you design your strategic narrative and launch assets.
The key is to execute this phase fast.
Too many Veteran Founders get stuck here. They want everything to be perfect before they launch. They want to “get it right” before they put it out into the world. But you only get clear by shipping, getting feedback, and iterating.
Think of this like a sprint. You can’t spend six months iterating on your messaging. You want to build, ship, and learn. Because when everyone is on the same frequency, everything accelerates.
The mission gets lighter, decisions get faster, and you move as one.
Phase 4: EXECUTE – Fire Your GTM Plan and Adjust
Once the POV is locked and the team’s aligned, there’s only one thing left to do.
Get off the whiteboard and into the fight. This means talking to customers, driving email sign-ups, onboarding users, whatever it takes!
Execution is where most Veteran Entrepreneurs stall out. They want to keep planning, keep refining, keep making one more slide before they ship. But you can’t plan your way to traction.
This is the toughest phase because most Veteran Entrepreneurs hate selling.
They’ll build a product. They’ll create content. They’ll work on their brand. But when it comes time to actually get on sales calls and close deals?
They freeze.
They’re more focused on being right than staying in the fight and being an entrepreneur!
At first, selling feels uncomfortable. It feels pushy, like you’re asking for something instead of earning it. If you’ve designed a category that solves a real problem for real people, then selling is serving. You help people understand why your solution is the right fit.
This is important because you have to validate your category and POV with customers. Until then, it’s just a thesis. You won’t always get it right the first time. Once you start talking to customers, you realize it actually falls flat.
From there, you improvise, adapt, and overcome.
No plan survives first contact with the market.
That’s how I learned to think as an infantry officer—fire and adjust. Not perfect or polished. Just precise enough to make contact and smart enough to adapt once you do.
You can have the perfect strategy and still have to pivot once you’re in the fight.
The best Veteran Entrepreneurs I know operate like the best leaders I served under. They’re decisive under pressure and humble in the face of reality. They don’t freeze when feedback comes in. They adapt and keep moving.
Fire. Adjust. Fire again.
Choose Your Hard
There’s nothing easy about the path you chose.
As a Veteran Entrepreneur, you choose to live your life in “hard mode” by pouring your blood, sweat, and tears into building something that didn’t exist before. Not only sacrificing money, but more importantly, you’re sacrificing time away from your friends and family, which you won’t get back.
But you’ll never have to go to sleep wondering if you have what it takes to be a Veteran Entrepreneur.
In the words of Theodore Roosevelt:
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”
As a Veteran Entrepreneur, you win by taking time to think, articulate, and align your category strategy so your team can execute it with you.
This is the work.
Define your mission and unique POV.
Build a business that matters.
Own your category.
You now have the structure to move fast and the ability to adapt as you learn.
You don’t need to chase tactics or accolades anymore—your focus is on running missions. You’re learning with every rep, sharpening with every customer, and getting stronger with every iteration. You already had the courage to build a business. You now have the framework to execute.
So lighten your ruck. Lock in your mission. And get back in the fight.
– “IRON” Mike
Special shout to writing partner in crime, Katrina Kirsch, for being in my corner and helping me bring this piece to life. I couldn’t have done it without her. There’s an old African proverb that says, “If you want to go fast, go alone; if you want to go far, go together.
P.S. - Ready to articulate your category strategy and POV?
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The Category Design Reading Lists
Wow lots of great stuff in here. I'm bookmarking for reference later.
I’ve always felt like a misfit in corporate life. After the Army, arguably the biggest corporation in the world, the idea of jumping into another hierarchy never sat right with me. I’d rather build something from scratch, solve real problems I experience in business, and build cool shit that makes people’s lives better.
But entrepreneurship is insane. Working with limited resources. Typically your own. Sacrificing a steady paycheck today for the hope of success later. Creating a story and then selling it to a world that doesn’t believe in it yet, while putting your name and reputation behind it. It’s a rough, lonely road.
I’ve leaned into the military angle as part of my founder story, but Mike’s right. The benefits are limiting, and the risks of pigeonholing yourself are real, both publicly and more dangerously in your own head. This piece hit me at exactly the right moment. A moment of grind. A moment of weakness. That moment founders know. Wondering if all the time and sacrifice will ever be validated.
It lifted me up, changed my perspective at the perfect moment, and gave me the motivation I needed to keep punching. Founder to founder, thanks Mike.