Failing to Save the World

In this episode of Failing to Tell a Story I dive into the story of Experimatch —an app concept born out of one simple problem: Where should my wife and I go for a night out? What started as a way to make date nights effortless quickly evolved into a full-fledged startup idea. I’ll take you through the journey of conceptualizing the app, the challenges of bringing it to life, and the decision to j...

In today’s episode of Failing to Tell a Story , Timothy shares the tale of his overly ambitious—and ultimately disastrous—attempt to start a LEGO reselling side hustle. What began as an exciting new venture quickly spiraled into a cluttered, overwhelming mess, with unsorted bricks taking over his home and testing the patience of his supportive (and long-suffering) wife. From the thrill of scoring...

In this episode, I share a personal reflection on the fleeting moments of parenthood and the realization that time with our kids moves faster than we think. I discuss how this led me to start a daily video journal, capturing the highs, lows, and everything in between. From cute toddler refusals to family chalk drawings and even a newborn’s first days, each video has become a cherished way to prese...

In this hilarious and slightly chaotic episode of Failing to Tell a Story , I take you through the whirlwind journey of my reselling adventures—starting with neckties and ending in a mountain of dress shirts, pants, and even a backyard zipline! What began as a simple side hustle spiraled into an addiction to thrift store treasures, leaving me with over 500 articles of clothing, a lot of frustratio...

In this episode of Failing to Save Finances , we take a look back at 2019, when it was just Timothy and his wife living in a small apartment, navigating the challenges of managing finances (or a lack of accountability, at all). This series will eventually take a retrospective journey through their spending month by month, identifying areas where costs could have been reduced and lessons learned. B...

In this follow-up episode of Failing to Tell a Story , Timothy shares how past mistakes in reselling led to an unexpected success: neckties. After learning from the pitfalls of trying to sell random items with no focus, Timothy discovered that specializing in neckties was the key to finding consistent success. Hear how a bumpy start turned into steady sales and what this journey taught him about h...

In this episode of Failing to Tell a Story , Timothy shares the highs and lows of starting a reselling business with Keenvintageeye. From the excitement of launching to the missteps of buying the wrong products, this story covers it all. Discover how lack of research led to reselling mishaps like fine china that no one wanted, a warped vinyl record, and a torn WWII book. It’s a tale of trial, erro...

In this episode of Let's Talk , we explore how to approach arguments with a focus on understanding rather than winning. Arguments don’t have to be about winners and losers—real progress happens when both sides come with the best intentions. Timothy shares insights on how to view the other person's perspective with empathy, aiming for a constructive exchange instead of a battle. Learn how to naviga...

In 2014, [Host's Name] had a bold idea: a platform called SoComAnon that would allow college students to anonymously share their thoughts and struggles. It was a promising concept, aimed at giving students a voice and fostering connection, but like many great ideas, it didn’t go as planned. In this episode of Failing to Tell a Story , Timothy takes you through the rise and fall of SoComAnon, shari...

In this candid episode of Let's Talk we tackle the tricky topic of defeat—starting with a personal story about how even trying to make a podcast on defeat led to... well, defeat. Timothy opens up about succumbing to that feeling of failure, but more importantly, the lessons it brought. Discover how embracing defeat and reflecting on its lessons can actually become a stepping stone to growth. It’s...

In this episode of Let's Talk , we dive into the common struggle of sticking with a project after the initial excitement fades. Whether it's a personal goal, a new business idea, or a passion project, it’s easy to lose momentum—even when we've set realistic, attainable goals. Timothy Olsen shares personal stories and practical advice on how celebrating small victories can reignite your passion and...