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149 | On Trajectory With Tyson Koska

Tyson Koska shares his On Trajectory tool and what led him to his own path of Financial Independence. They discuss how Tyson got started with FI and how On Trajectory tools cover net worth tracking and digital options.

Tyson’s Story

Brad and Jonathan had heard about Tyson from many members in the FI community. His tool, On Trajectory, is a comprehensive way to digitally track your net worth. He had been a part of the FI community even before he built this tool. Although he started practicing FI principles on his own, he joined the community with full force once he found it.

I mean, I couldn’t sleep at night if I didn’t have some sort of plan to know that there was a time when I could just stand up and walk off my job and not have to worry about the, you know, where I was going to get my next meal.

However, Tyson was not always inclined to follow the path towards FI.

Early Days

Tyson grew up in an affluent area without actually being very affluent. Due to that, he was constantly comparing himself to others. He knew that he had no chance of getting the things they had unless he had a plan to get there.

After graduating high school in 1986, Tyson joined the military and started earning a steady paycheck. He went into the Army as a warrant officer in order to learn how to fly helicopters. As a warrant officer, you get paid almost the same as a regular officer but you don’t need a college degree.

At that point in his life, he felt a strong desire to ‘keep up with the Joneses.’ That desire caused him to start spending more than he was making.

With that, he got himself into the biggest debt of his life. Opening store cards and purchasing a new vehicle were just a few of the choices he made during this period. It led to thousands of dollars of credit card debt to carry around. He quickly realized that this feeling was not a good one.

Turning Point

At some point, Tyson decided that he wanted to turn his financial picture around. Around this time, he was sent to a combat zone in Iraq. Tyson says jokingly that this order got him out of debt. He was living in a combat zone without anything to spend money on. Plus, he was earning more money because he was in a combat zone.

As soon as he got out of the military, he decided to pay everything off and start investing.

That sense of safety and security that was created, knowing that I had a path that was an upward trajectory instead of the downward trajectory that I had been on, having that sense of freedom and wellness was an emotional moment for me and I never wanted to lose that again.

From there, Tyson started moving along his path to Financial Independence.


After the military, Tyson left with all his debt paid off and extra money in the bank. Plus, he was entitled to the GI Bill. He chose to double major in English with a concentration in writing, and a minor in Philosophy.

Although he did not have immediate job prospects upon graduation with a liberal arts degree, he still valued that degree. It taught him skills such as thinking, writing, and argumentation that have served him well.

I really value the skills that I learned in my liberal arts time. The thinking and the writing and the clarity of argumentation and all of those great things. Plus, I fed my brain, all the nourishment that it wanted.

Listen: A Military Path To FI With The Military Dollar

Inflection Point

Without any job prospects, Tyson turned to teaching. He became a long-term substitute teacher for 7th grade English. However, that did not last long.

Tyson did not seem to have a path. But he had always been tech-savvy, so he switched to teaching computer courses. The adults taking the classes were much easier to work with than middle school kids. At the same time, it allowed him to rekindle his tech background and build on it. While he taught classes, he took other tech classes at the same school for free. Within 18 months, he landed a programming job and transitioned to a career in IT.

It is likely still possible to land a similar gig. Learning centers for adults still exist and it is a way to get your foot in the door.

Don’t let your own limiting beliefs hold you back. The struggle with imposter syndrome can be difficult to overcome for new teachers. Tyson struggled with this, yet his professor ratings online are very high.

Career In Tech

Once Tyson transitioned into tech, he never left. With a larger paycheck, Tyson’s savings went through the roof. Although he had always managed to save something, a bigger paycheck meant more possibilities.

Along the way, he started tracking his journey to FI with a smattering of spreadsheets and calculators.

On Trajectory

Tyson founded On Trajectory within the last five years. The impetus for building this tool was the arrival of his second child and the unknown impacts on his FI goals. It was not a simple process to calculate these changes even with a robust spreadsheet.

He knew what he wanted and was tired of waiting for someone else to build it. So, he used his software engineering background to build his own prototype in Excel. It was built with the FI community in mind and is regularly tweaked to add new interests.

Everything is built for a regular consumer, a regular person just to find out the answer to that question ‘What does the arch of my financial life look like? If I add this complexity in and do this other stuff, when can I be done or what are the options that I have?’ It’s built just to answer that question.

On Trajectory is responsive to the communities’ needs as they arise. However, the larger pieces have remained consistent for years.

The tool is meant to be a complementary tool to Mint and YNAB and a direct competitor to Personal Capital. On Trajectory is very similar to Personal Capital, but it came out two years earlier. On Trajectory offers the chance to add smaller pieces to your financial life such as modeled expense stream across different periods of your life. It also takes different steps to reflect the inflation of certain expense streams.

The kind of control that you get is well well past anything that Personal Capital offers but from a basic usability standpoint that’s probably the closest competitor out there.

Check out On Trajectory here.

Building A Business

In order to get started with a software tool, the idea of a minimum viable product is important. There is always something more that you could add but you need to work through iterations quickly.

The “minimum viable product” thing is key. You have to, hopefully you’ve got a pretty good idea of [what] the market place could use and hopefully you’ve got some support around you, you’re not doing it completely alone…but you do have to get something out quickly and not be afraid of criticism.

At first, he thought that everyone would love it. Of course, every consumer has a different opinion. However, Tyson says the tool only exists because he likes to use it himself. With that, he knows there will always be at least one person in his audience.

Keeping that fun, that enjoyment, that passion–let’s just say it this way; you’ll never be able to keep your passion, about your whatever product you’re trying to build or lifestyle you’re trying to pursue, you’ll never keep up that passion if it’s not something you don’t really love and enjoy doing.

The On Trajectory team consists of four key partners. As the tool continues to grow, Tyson is learning to manage a business in addition to maintaining a useful FI calculator.

If On Trajectory sounds useful to you, then check it out here.

Listen to the Friday Roundup of this episode here.

How To Connect

You can connect with Tyson through He has links to his personal phone number and email at [email protected]

The Hot Seat

Favorite Blog: Budgets Are Sexy

Favorite Article: A Ted Talk about building a tower of spaghetti with a marshmallow on top. 

Favorite Life Hack: Credit card reward points.

Resource: Learn about travel rewards with ChooseFI’s free course.

Biggest Financial Mistake: Signing up for and maxing out every credit card he could.

The advice you would give your younger self: Try saving a little earlier.

What is the purchase that you’ve made in the last 12 months that has added the most value to your life? A retractable Bluetooth headset.

Related Articles

New to FI? Be sure to check out Episode 100: Welcome To The FI Community!

Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a ChooseFI advertiser. Disclosures.
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