We love grabbing drinks with our entrepreneur friends because they always have the craziest stories. Sometimes it’s a big, unexpected win. Other times it’s a problem that came out of nowhere and couldn’t possibly have been foreseen. There is so much to learn from these stories and so we asked some of the brightest entrepreneurs and creatives in the community to share some of those stories below. 

Peter Allen

One of the craziest and most rewarding experiences in my business journey was building 953 JAMZ from the ground up while people doubted whether it could even succeed. There were times when I questioned if all the sacrifices, long nights, and challenges were worth it. Then something amazing started happening. Artists, business owners, and community leaders began reaching out to us for interviews and partnerships. Read More>>

Guillermo Ursini

I moved with my family from Argentina to Miami in the USA in 2017, seeking to advance my career as a sound engineer. I truly never imagined that my dream would come true, step by step. Read More>>

Sarah Banks

Eleven Years Later June 4, 2026 Eleven years ago, my life changed forever. I didn’t know it at the time, but that accident would divide my life into two distinct chapters: before and after. Before the pain. Before the trauma had a name. Before my body became a battlefield. Before I learned what it truly meant to survive. Read More>>

parris balazs

Early in my career, I experienced something that no planner expects. The officiant for one of my couples, who was also a close friend of theirs, passed away unexpectedly after the rehearsal dinner. The couple ultimately chose not to proceed with the ceremony and instead used the day they had planned as a memorial to honor him. Read More>>

Jean Ketcham

One of the things I am most proud of is our ‘Tastefullly Nude Calendar’. Women 50 to 86 tastefully posing (important parts covered) and writing below their picture, how they felt about aging. After the first Calendar came out – I was at a graduation party in Chicago and everyone was talking about the Calendar. Read More>>

Kerrie Campbell

If someone had told me that one of my best business decisions would happen in an airport departure lounge while I was emotionally preparing to fly across the world to see my 19-year-old son, for the first time in over a year, as he had joined the military and was stationed overseas, I probably wouldn’t have believed them. But that is exactly what happened. Read More>>

Emmie Levy

One of the most unexpected parts of being an entrepreneur is that you can spend years working toward a goal, only to have the moments that change your life happen when you least expect them. A few years ago, I was just a girl with a dream. Read More>>

Jason Pietruszka

The craziest thing that’s ever happened in my business wasn’t a lawsuit, a difficult client, or a project gone wrong. It was waking up and realizing that an entire community where we had built homes, relationships, and friendships was burning. As the Pacific Palisades fire unfolded, I wasn’t watching it on the news as a distant event. Read More>>

Jill Kaufman

One of the biggest challenges I’ve faced in my business involved something completely outside of my control: my Facebook Ad account. For years, Facebook ads have been one of the primary ways I’ve reached new clients and grown my business. Several years ago, my ad account was hacked, and someone fraudulently spent tens of thousands of dollars. Read More>>

Tamara Stavrianoudakis

Debbie Reynolds’ son came into my store and asked if we wanted any furs or wardrobe which was used in movies that his mother collected. I said, ‘Sure!’ He invited us out to his warehouses where I saw all the costumes from Gone With The Wind, Forrest Gump and so many others. I was like a kid in a candy store! Read More>>

Jeff Schwartz

Most of my visibility comes from publishing whiskey reviews. I remember a time about three years ago when a reader disagreed with my rating and went so far as to say I have no idea what I’m doing. Those kinds of comments come with the territory, and they’re easy to brush off. My ratings take several factors into account, including value. Read More>>