Late last month at Mix N’ Mentor Beirut, we got to play the role of nosy reporters, dragging five mentors away from their sessions and getting them to answer personal questions on camera.

The resulting videos offer a unique snapshot into the life of an entrepreneur, showing that people who have achieved the designation of ‘Wamda mentor’ struggle with the same daily challenges as people who are just starting out. Just because these five entrepreneurship experts – Sohrab Jahanbani, founder of GoNabit.com; Elie Habib, founder of Anghami; Rabih Nassar, founder of Apstrata; Dr. Philip Boigner, VP of Investments at Dubai Silicon Oasis Authority; and Oussama Ammar, founder of French accelerator/investment fund TheFamily have achieved a measure of success in their respective sectors, doesn't mean that running their businesses is suddenly a walk in the park.

In the first video in the series, Jahanbani, Habib, Nassar, and Ammar share their most embarrassing professional moments. For Jahanbani and Ammar, these have featured emails gone wrong (Ammar mixed up an email to his girlfriend and one to someone he’d been chasing for advice for two years!). Habib and Jahanbani also engage with the idea of pride: for Habib, pitching endlessly to “everyone who had VC on their LinkedIn profiles” was a humbling experience; Jahanbani recalls being “treated differently” after the failure of one of his ventures. Nassar recounts a story when he wasn’t as responsible as he could have been with an early client, who as it turned out had been struggling with a personal tragedy.

These mentors shared their most embarrassing moments on video for our benefit; feel free to share yours in the comments below.