When Can I Retire? | Tyson Koska from OnTrajectory

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Today’s episode features Tyson Koska from OnTrajectory.

Tyson joined the Army when he didn’t have enough money to go to the college he wanted.

Later, he would end up with an English and Philosophy degree which didn’t land him a job.

He fell back on an old skill of programming and up-skilled his way into eventually making six figures.

Listen, learn, and let us know what you think about Tyson’s amazing turnaround.

Episode Summary

Tyson’s background

  • From a young age, he had jobs and tried to make his own money
  • His goal has always been to be independent
  • When it was time to go to college his parents offered to help
  • But for them to do so he would have to live at home
  • Instead, he decided to join the Army and became a helicopter pilot
  • Tyson admitted he made a lot of missteps when he first started working
  • He blew all his money and racked up credit cards

Reinventing and Up-Skilling

  • He left the military in 1992
  • In the end, he would end up in that little local college after all
  • Tyson decided to study English and philosophy
  • Those majors didn’t provide any job prospects
  • Tyson fell back on his old skill of programming that he learned at age 13
  • This spun into a job and a pipeline for up-skilling
  • Over that stint, he would climb from $30k income to over $100k
  • His income was increasing but so was his spending
  • Tyson says that was largely due to marrying the wrong person
  • Then we discussed what really flipped the switch for him
  • He recalls a friend who wanted to open a McDonald’s
  • His friend said he needed $100k to do so
  • That sounded like a ridiculous amount of money to him but inspired him

Creating OnTrajectory

  • Another big turning point was when his second kid was on the way
  • There was so much unknown and he couldn’t find a tool to help him plan for them
  • This need led him to build OnTrajectory
  • Now he sees both individuals and advisory firms using the tool
  • It’s also available for a free 30-day trial with no credit card needed to sign up
  • Then Tyson walks us through all the incredible detail you can get from the app
  • There are walkthroughs on YouTube as well as several guides
  • It’s a really cool tool that allows you to insert tons of complicated life events into your projections


Key Takeaways

  1. Mistakes Happen: Tyson calls out several missteps but he learns from them instead of dwelling on them
  2. Life is Complicated: OnTrajectory was born out of this idea to model all the crazy life events we can run into

Call to Action

Head on over to OnTrajectory to start your 30-day free trial and see what your plan looks like with all those important life moments.

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T’s Information

His Website: OnTrajectory.com

Via E-Mail: ty@ontrajectory.com or questions@ontrajectory.com


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