After dropping out of college with a 1.2 GPA, Jordan found himself at a crossroads that would unexpectedly lead to his entrepreneurial calling. Enlisting in the United States Air Force, he served as a network engineer, where he witnessed firsthand the bureaucratic maze that veteran contractors faced when dealing with the Department of Veterans Affairs.
Jordan’s own transition out of military service brought this problem painfully home when he was billed $15,000 for inadequate VA claim assistance that yielded minimal results. Refusing to accept defeat, he threw himself into researching the complex VA system on his own. His tireless efforts paid off when he successfully secured a maxed out 100% permanent and total VA rating — a rare achievement that typically eludes many veterans.
This personal victory became the catalyst for his mission: to create a better system for veterans navigating their benefits. “I realized this wasn’t just my problem,” Jordan explains. “Thousands of veterans were being underserved by a system they’d sacrificed to defend.”
Starting with nothing but his laptop and firsthand experience, Jordan launched VA Claims Academy, democratizing access to VA claim information through straightforward, actionable content. His no-nonsense approach and genuine
commitment to fellow veterans quickly resonated, amassing over 80,000 YouTube subscribers and millions of views documenting the intricacies of the VA benefits system.
Today, Jordan’s venture has helped thousands of veterans successfully navigate their claims, recovering millions of dollars in earned benefits. His unlikely journey from college dropout to military service to disruptive entrepreneur demonstrates how personal challenges can fuel innovation when paired with authentic passion and persistence.
“The best solutions come from the people who’ve experienced the problem,” Jordan says. “Sometimes your greatest setback becomes your greatest comeback.”
What is your typical day, and how do you make it productive?
My typical day involves writing evidence drafts for my clients, conceptualizing or filming YouTube videos, and meetings with my incredible team. Then at night it’s time to get out of my own head and get some salsa dancing in. The key for my productivity is sleeping until I wake up naturally. I feel sharper.
How do you bring ideas to life?
Not all ideas deserve to be brought to life.
I follow what I call “problem-solution mapping.” First, I immerse myself in understanding the problem completely — with VA claims, this meant documenting every frustrating step, confusing form, and bureaucratic roadblock veterans face. I spent hundreds of hours studying regulations that most people never read.
Then, I break complex systems down into teachable frameworks. For VA Claims Academy, I created a step-by-step approach that transforms overwhelming processes into manageable actions. I test everything personally or with a small group of veterans before scaling.
What sets my approach apart is my commitment to transparency. I share both successes and failures publicly through my YouTube channel, allowing the veteran community to learn alongside me. This creates a feedback loop that constantly improves the solution.
The final piece is accessibility — ensuring the information reaches those who need it most. I deliberately use straightforward language instead of government jargon, and make sure core resources are available to veterans regardless of their financial situation.
What’s one trend that excites you?
There is a trend of veterans realizing they aren’t alone in their quiet suffering and are now able to come to terms with the fact that their service impacted them in a serious way, and are willing to finally set the record straight.
What is one habit that helps you be productive?
Staying physically active, sleep until I wake up naturally.
What advice would you give your younger self?
Don’t let the system mislead you into thinking you’re dumb.
Tell us something you believe almost nobody agrees with you.
I believe all asset growth, including enterprise value growth should be measured against gold instead of dollars. This will help you determine value instead of just price.
What is the one thing you repeatedly do and recommend everyone else do?
I repeatedly search for ways to avoid reinventing the wheel. Chances are, you don’t have to start from scratch on anything, refine what someone else has already started.
When you feel overwhelmed or unfocused, what do you do?
I listen to music and dance. Gets me out of my head and into my body.
What is one strategy that has helped you grow your business or advance in your career?
One strategy that has helped grow my business is to truly keep it simple. Avoid engineering complex solutions to problems that don’t even exist.
My 3 strengths are the ability to think simply, the willingness to do nothing about something, and my willingness to say “no”, to opportunities. This has helped avoid chasing “the girl in the red dress” as some call it.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
I used to think that doing additional things was the answer to scaling, and found out it really is just doing more of what already works, or doing it better.
What is one business idea you’re willing to give away to our readers?
A virtual medical clinic that has doctors who write evidence for veterans through telehealth.
What is one piece of software that helps you be productive? How do you use it?
I use Google sheets to keep track of which clients I have completed evidence drafts for.
What is the best $100 you recently spent?
The best $100 I spent was on dinner with my lovely wife.
Do you have a favorite book or podcast from which you’ve received much value?
The Fruits of Graft by Wayne Jett. It allows you to understand the monetary system, which is truly the only way to know you’re gaining wealth.
What’s a movie or series you recently enjoyed and why?
I enjoy the anime My Hero Academia because it’s a perfect depiction of the concept of flow or groove, and how once it abandons you as a vessel, you cannot forcefully grasp it again.
Key learnings:
- The importance of determining value instead of price
- Greatness is outside the box
- Don’t let traditional education convince you you’re dumb
- The importance of keeping it simple
- Never reinvent the wheel