What does it take to turn a felony conviction into a story of triumph? In this powerful episode, Derek Tsuboi opens up about his transformation—from legal struggles and hidden truths to Spartan race glory and entrepreneurial success. With raw honesty, he shares how embracing authenticity, enduring hardship, and redefining failure led him to reclaim his life. Don’t miss this exclusive conversation about resilience, redemption, and the power of owning your story.

Based on Derek’s post on Facebook I really wanted to go through all of this with him and see what I could learn:

No Matter How Far Down You Go There’s Always a Way Back Up

10 years ago I was a completely different person. I’m sure you can tell from this photo.

Since I can remember, I guess you could say one of my first businesses was “the hustle”.

2014: Josh and I were trying to make money from Rediscover Productions (yes we had a slightly different name back then). We were the agency for bands. We booked shows, made merch, & gave bands advice. Karem and I started getting serious around this time. I was just getting started in trying to do my own thing with online business. I knew at this time that I wanted the freedom to call the shots in my life.

2015: I went down on felony charges. Karem and I were 2 months into our first apartment together. If there was ever a time to leave this would’ve been it. I had to complete a year-long rehab program and deal with a plethora of legal fees while balancing my full-time job and keeping this hidden from everyone.

2016: I completed the program and was exonerated by the state of Florida. Right after this I bought my first house in FL & married Karem in Bogota, Colombia. I almost missed my own wedding because I couldn’t leave the county until my case was closed.

2017: We had our daughter Wren and I became a father.

2018: I quit my corporate job, sold our house, and moved us back to my hometown with my parents, right before our second child Atlas was born. I picked up a job at UPS to make ends meet.

2019: I relentlessly sought out opportunities online to learn from people doing what I wanted to do (Thank you Alex Taylor) and I finally started making enough internet money to stop working BS gigs.

From this point on, my life’s been a dream, but It hasn’t been easy by any means.

I started my journey growing my business online in the thick of it.

I couldn’t have picked a worse time to do it, which is why I feel like it’s worked out for me.

Your mistakes don’t have to define you.

I never tried to get the photos removed because I knew one day I’d share this story. This is the first time my family has seen this. Sorry, y’all. 

If you thought this was shocking wait till you hear what else I’ve got to share…. Stay tuned.

——— EPISODE CHAPTERS WITH SHORT KEY POINTS ———

(0:00:01) – Journey From Felony to Spartan Races
Derek Tsuboi’s journey from felony conviction to successful online business and passion for Spartan races and Zombie Run.

(0:06:14) – Journey of Redemption and Transformation
Personal growth and authenticity through sharing hidden past, courage to inspire change and redemption, and the role of environment and perception in shaping mindset and success.

(0:20:07) – Navigating the Road to Redemption
Dealing with aftermath of legal issue, rehabilitation challenges, release from jail, drug program, perseverance.

(0:32:27) – Courthouse Wedding Miracle
Derek risks missing his wedding due to a court program, but successfully completes it and proceeds with his plans.

(0:39:39) – Learning From Mistakes, Building a Future
Permanence of online content, owning past mistakes, moving back to Columbia for community and balanced lifestyle.

(0:43:19) – Enduring Challenges of Entrepreneurship
Sharing personal story online, transparency, authenticity, integrity in business, financial pressures, perseverance, entrepreneurship, finding meaning.

(0:53:14) – Failure on Path to Success
Embracing failure leads to success through resilience, support, health, family, mindset, and financial prudence.