Most financial planning tools either oversimplify your future or drown you in complexity you can't act on. Tyson, founder of OnTrajectory.com, built something different after watching his own financial trajectory shift from debt-laden college graduate to financially independent — and he did it by treating his finances like a flight plan, not a wish list. Brad and Jonathan sit down with Tyson to unpack how he went from accumulating debt in his youth to creating one of the most robust (yet intuitive) financial planning calculators in the FI community. Tyson shares how leveraging the GI Bill, adopting a proactive mindset, and visualizing his financial arc transformed not just his own path, but also sparked a tool that's helped thousands map theirs. Introduction to OnTrajectory [00:00:40] Overview of OnTrajectory as a financial planning tool and the role of technology in making complex projections accessible. Tyson's Journey to Financial Independence [00:01:49] Tyson's early financial missteps, lessons from military service, and how the GI Bill became a cornerstone of his wealth-building strategy. Understanding Financial Planning Tools [00:24:55] The gap in user-friendly financial calculators and Tyson's motivation for building OnTrajectory based on his own need to answer: "What does the arc of my financial life look like?" The Importance of Community Feedback [00:32:10] How Tyson iterates on OnTrajectory by releasing early, embracing criticism, and letting user input shape the tool's evolution. Tyson's Hot Seat Questions [00:38:18] Personal insights on favorite resources, biggest mistakes, and life hacks. Key Quotes: "Understanding your financial trajectory is key." [00:27:30] "Embrace feedback to improve your financial tools." [00:32:10] "Teaching reinforces learning." [00:19:11] "Pursuing passions can lead to unexpected outcomes." [00:12:06] "Start saving now for a better financial future." [00:41:32] Actionable Takeaways: Start budgeting to understand your financial picture better. [00:09:00] Use OnTrajectory to model your financial future and stress-test different scenarios. [00:27:54] Seek community feedback for your financial decisions and tools. [00:32:10] Resources: OnTrajectory Website [00:44:00] Related Episode: 095: Military Dollar: Understanding the GI Bill [00:15:02]