10 Most Embarrassing Moments as an Entrepreneur

Think of the most embarrassing business story you have as an entrepreneur and see if they compare to Patrick Bet-David’s 10 most embarrassing moments from his own career as an entrepreneur.

“Listen, here’s the moral of the story. I’ve had a lot of embarrassing moments and I’m not really worried about it. I’m probably going to have many, many more. Business is ugly. It’s not always going to be perfect. You’re going to have embarrassing moments, scary moments or dumb mistakes, but the key is to keep going and not let it slow you down.” -PBD

10 Most Embarrassing Moments as an Entrepreneur

  1. False Alarm

    1. Back in 2006, Patrick was giving a talk and he really wanted everyone’s undivided attention. He said, “If you do need to use the restroom or you’re pregnant, that’s totally okay to step out. But if you’re not pregnant, please stay with me.” A woman got up to leave and Patrick told her, after looking at her, “Your pregnant, I understand, the bathrooms are on your left.” She immediately got mad and said, “How dare you. I’m not pregnant!” Patrick just wanted to crawl into the smallest hole he could find. The good news was the room felt bad for him and he got them back on his side after that embarrassment. He won’t make that mistake again.
  2. Lost Luggage

    1. Patrick was accepting an award in Bermuda and wouldn’t you know it, the airline lost his luggage in Miami. He waited until the day of the award ceremony, hoping his bag would come but it didn’t. He could find a suit, but no shoes fit him, so he wore flip-flops to the ceremony. Patrick accepted the award and walked across the stage wearing flip-flops. He has a video of it, everybody from that award ceremony does.
  3. “Sorry, Pastor”

    1. In 2010, Patrick scored tickets to Game 7 of the NBA Finals, Celtics vs Lakers. He asks his friend and die-hard Laker fan, Pastor Dudley, to come with him. On the drive to the game, in a cell phone dead zone of the 210 Freeway, he runs out of gas. Side note, Patrick has run out of gas at least 50 times in his life. They just make it to the game on time and everything is great, right?
    2. A few weeks later Pastor Dudley invites Patrick and his whole family to a service where Pastor Dudley tells his whole 15,000-person congregation how Patrick ran out of gas. But Pastor Dudley wasn’t done there, he wrote a book and chapter one is all about Patrick running out of gas on the way to The Laker game. Patrick became the guy that ran out of gas to everybody he meets from then on. But it becomes the best conversation starter helping out Patrick’s business.
  4. “Your Machine is Broken”

    1. Way back when Patrick was coming up, he had maybe five dollars to his name and $49,000 in debt. He had a dinner with a huge client that if the deal went through it would net him $6,000. Big money for Patrick at that time. So, Patrick offers to pay for dinner and the waiter says his card is declined. Naturally, Patrick tells the waiter that the machine is broken, and his card is fine. Of course, he knows his card was going to be declined. The waiter goes to run the card again, but Patrick is thinking one step ahead. He excuses himself to go to the bathroom, finds the waiter, and works something out to cover the bill. Patrick comes back tells everyone that it was the restaurant’s machine and he saves his reputation and the deal. That same situation happened a few times during his first year of business and he is living proof that it is okay if it does happen.
  5. Lucky Day

    1. One day, Patrick was driving around with a new salesman he hired and was so excited about mentoring.  This salesman was a killer and with Patrick’s help, he was going to be big. But Patrick gets pulled over and the cop puts him in handcuffs. Apparently, Patrick had 16 unpaid speeding tickets and his license was suspended for the last eight months. All of this is going on in front of this new killer salesman who Patrick was going to mentor and on his very first day. Then as luck would have it, another emergency calls the cop away and Patrick is let go. He had to clear up the tickets in court, but he was very lucky he didn’t have to go to lock up that afternoon.  
  6. Kitchen HQ

    1. In order to cut costs on office space, Patrick wanted to move his office from LA County to Burbank. He found the perfect place and sub-let his old office to someone else. But because he did not sign a contract, the new place fell through because another buyer was willing to pay more. For 90 days his team had to work in a rented kitchen space that was way too tiny. Everyone was miserable and they all wanted to kill each other. It goes without saying they absolutely didn’t let anyone come and see it. They would hold meetings in the parking lot because it was so embarrassing.
  7. The Magical Sound

    1. Wardrobe malfunctions are hard to bounce back from. Patrick was giving an impassioned speech to a room full of at least one hundred fifty people, trying to get them fired up about delivering and executing. When he noticed people laughing in the front row. So, he calls them out and asks what’s so funny? They whisper to him, “Patrick, your zipper is down.” Patrick, not quietly enough, pulls his zipper up but the room heard it and it erupts with laughter. Afterward, people came up to him and told him, “It was your best talk. We felt like, were you relatable because your zipper’s down. It was so awesome.” Next time this happens to you remember, Pat’s had this happen to him as well.
  8. “Fore!”

    1. Golf is huge in the insurance industry because they buy so much advertising space. After years of avoiding playing golf, Pat got invited to a tournament. Thinking it couldn’t be any harder than baseball, he felt ready to crush it. “Think about the most embarrassing moment anybody could have in golf in one day. I don’t think anybody’s was more embarrassing than mine.” -PBD
    2. Patrick might have hit a few birds instead of birdies. Sweet relief came when they reached the 9th hole and Patrick graciously and mercifully took a break. His partners were encouraging but it was not a surprise his play was the talk of the clubhouse, and not because it was so good.
  9. The Stinky Salesman

    1. Always remember that your stuff stinks just as much as the next guy. Patrick was on a sales appointment and from the moment he sat down with the guy he could smell something awful. There was no way he was going to spend an hour with this stinky guy, so he cut the appointment short. After the appointment, Patrick goes into the bathroom and looks down, his tie had his little kid’s poop on it from the morning. Patrick was the stinky salesman. The other man was so kind and never brought it up and for that Patrick thanks him and can’t apologize enough.
  10. The Special Connection

    1. Back in 2005, Patrick was working at an office that he regularly went into on Sundays to get some work done in peace and quiet. When he pulled up, he saw two cars already parked. It was strange, but he went in any way. As he opened the door to the office, he caught two of his employees in the act. They gave the excuse that since they live with their parents the office is the only place to do their business. They got dressed and left after scaring Patrick for life.
    2. The next day, Patrick was standing right next to where it happened, in a meeting, and he calls out the employees out by saying, “So listen, let me tell you something. One of the things that impresses me the most is when I see people show up on Sundays to prepare for their week and let me tell you who showed up this Sunday to the office.” He has the two of them, beet red, stand up and Patrick says he’s proud of them for taking their game to the next level.

Next Steps: Watch these two videos. First, watch 11 Scariest Moments in Business as an Entrepreneur and then watch 12 Dumbest Mistakes I Made My First Year as an Entrepreneur

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