One of the most under-the-radar benefits of entrepreneurship is its ability to build fortitude and make the entrepreneur a more formidable person. Challenges – particularly the crazy, unexpected ones that take on a life of their own – build character and confidence. And the unexpected surprises to the upside, the crazy good moments offer a high that’s hard to reproduce elsewhere. The charm and the challenge of entrepreneurship is dealing with the crazy things that happen and so we’ve asked some fantastic business owners and leaders to share some of their stories with us below.

Alice Hu

One of my clients was experiencing delays selling his business. Something would always come up with the buyer. Debt was accumulating and it was becoming more stressful with each day. He booked a reading with me and I shared some insights – specifically some dates and why this deal wasn’t going through. Six months later when he had a follow-up reading, he told me that he had sold the business! He listened to what I shared with him and was able to negotiate a sale with a buyer! Read more>>

Kayla Rose

“My path into the jewelry business evolved in an unexpected way. Before diving into this world, I built my foundation in styling, where I honed my eye for aesthetics, trends, and visual storytelling. This experience ignited my passion for fashion and ultimately led me to explore jewelry design. Joining a venture founded by my current husband and his ex-wife was not an easy feat. What started as a collaboration was incredibly challenging and created a lot of hardship and problems. Yet, through determination and resilience, we overcame those obstacles and emerged stronger. His ex partnerand wife was bought out and we moved in a new direction. Read more>>

JJ DiGeronimo

For a long time, I believed that money was the key to security, success, and even my sense of worth. Growing up, we didn’t have an abundance of it, and I internalized the idea that more money meant more stability—more control over my life. So, I chased it. I worked hard, climbed ladders, and made decisions that I thought would bring me the financial safety I craved. But beneath that drive was fear—the fear of not having enough, of not being enough, of losing what I had worked so hard for. No amount of money could truly quiet that fear because security isn’t just about numbers in a bank account. It’s about my relationship with money, how I hold it, trust it, and allow it to flow. Read more>>

Anthony Caldiero

I just lost $4000, basically all of the money to my name. I was 21 years old, and still deciding If I could make it, or if it was worth it to play poker full time. I had less than $7000 to my name at the time. My absolute dream was to be able to make a living making content about my life, my journey, and the poker games I played. As any “business” goes, it was by no means easy. I had to go through some of the toughest days of my life to get to where I currently am. Many days, I wanted to quit, and this is the story of the first day I wanted to quit, but fate had something else in store. Read more>>