We were lucky to catch up with Michael Oldroyd recently and have shared our conversation below.
Michael , thanks for taking the time to share your stories with us today It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
Risk-taking is what defines capitalism. It is the only thing we have that helps level the playing field. I’m not saying all is fair because it’s not, but we all have the opportunity to enter the poker game of American capitalism, even if we don’t have many chips. The more chips and skill we have, the greater chance we have of winning of course, but the willingness to take risks is everything… & the greater the risk, the greater the reward. Everything great I’ve ever achieved in my life required great amounts of risk. I’ve failed over and over and over again, and that is why I succeed. Remember when Michael Jordan said that? Well, I also say it because it’s true. People don’t remember how many times you fail. They remember the Superbowl rings, the championships, the achievements, the nuggets of gold that nobody can ever take away from you. They remember the apex or pinnacle of your efforts which are the victories (the Yahtzee’s), & every successful person has a deep pyramid of failures under that apex of achievement. Another analogy, success is the tip of the iceberg & most of the iceberg is underwater. The part underwater is, well you can fill in the blank. I’ve failed with football, women, comedy, business, and more… But I’ve also achieved more than most in each category. In each category I mentioned, I took lots of risks. If you max out the level of risk you take in a venture, you max out your potential for success & if you want to achieve success on the highest level, it is required to risk everything. I could go into an entire essay about what I’ve achieved in each category and the countless failures in each as well, but I’ll keep it brief for now. I’ve experienced love, being part of a D1 college football team that took the number one spot in the nation, individual player achievements that still match NFL combine standouts to this day, being in movies and on TV, performing for thousands of people, and being part of a startup from the ground floor of its inception that sold for millions of dollars, and more. For now, I’ll just write one of my favorite quotes to summarize: “The master has failed more times than the doubter has tried.”
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My personal mission statement is to bring infinite love and laughter to this world. I got into comedy because I’m hilarious and always have been. Every day I do my best to give my darndest in both categories, and that’s all I can do. I am not claiming that I am perfect or trying to be the source of all love and all laughter, but I am a love child, conceived on Valentine’s Day on my parents’s wedding night during their first official try on the books. Shout out to my Dad for that hole-in-one! There is love all around us already, and there are plenty of outstanding comedians that I’m honored to have shared stages with. There are also funny people we all know who aren’t comedians either. Humor, laughter, and joy can happen every day in life. I encourage you to keep an eye out for it.
Long story short, I just want to emit the love and the humor within me and be a reflector of both when needed for the rest, or maybe I just want to be a vessel that reflects love and humor in God’s cloud (pun intended). Basically, I want to shake the world with the sound of laughter as I give it multiple GirthQuakes and eargasms!
Let’s talk about resilience next – do you have a story you can share with us?
I helped a friend build a startup from the ground floor as the company’s first full-time operational employee. We were very small when I joined. Imagine if you had a friend tell you they had a map to some buried treasure and a boat to get there & he hired you for under-market value to help him get there and to find pirates to help get there as well, and you took the job because you knew if you achieved success (found the pirates booty), you’d share the spoils. You didn’t discuss any split of spoils because you didn’t want to disrespect your friendship. Yet, you had faith because it’s what a good friend would do and it’s what you’d do for a good friend if the roles were reversed. Imagine if you actually made it to the treasure one day, finally, after a long journey full of both accomplishments and setbacks, having given up the opportunity cost of time). You found treasure you weren’t even sure actually existed at one point because you did everything you could to make sure your friend didn’t fail because you had already failed hard enough at a dream to play in the NFL to know you didn’t want to see a friend have to experience that failure too. And imagine if when you arrived at the treasure, your friend didn’t show the appreciation you knew/felt you deserved, and he walked away with pretty much everything and then got in a helicopter or a penis-shaped rocket like Bezos and flew away out of your life after handing the ship captain title to somebody else that no longer treated you like a friend, but as a subordinate where they/them tried to get you to wear a ball-gag non-consensually. Imagine staying on board because of the others you’d brought into this venture and the fact that you didn’t want to abandon them, and because you also needed a way to get home… & because the ball gag really wasn’t that bad after all (kidding – I’m no sub!) Anyway, this new captain told you to find more treasure and to do the same thing you did before. Imagine if one day this new creature (that looked like Jabba the Hutt) claiming to be captain realized there was no more treasure to extract, and they told you to walk the plank. Imagine how that would feel. And then imagine finding the resilience to never give up on your friend regardless of everything, even though you realize he didn’t view you as a friend anymore. He didn’t even invite you to his wedding after all you’d done for him and after him promising you to make you a groomsman at his wedding someday. Regardless, you sent him a genuine card congratulating him and his wife, wishing them love. That’s me.
Have you ever had to pivot?
The answer to this question picks up where the previous question answer ended after I walked the plank. Keep in mind that while helping the person I thought was my friend who sold me to Jabba The Hutt, I was doing comedy the entire time. To give proper context, our business was in healthcare. I had the luxury of making an impact in healthcare by day for 7 years, all while doing comedy at night. In 2018, I walked the plank from a global consulting firm known as Jabba the Hutt, which had acquired our successful startup two years prior in 2015. Instead of finding a similar role in healthcare with a competitor, I decided to take all my chips and say, “I’m investing 100% in what I love and where my heart is, my comedy.’ I founded Droyd Entertainment through the state of New York. I truly do appreciate NY for their help. The mission statement of Droyd Entertainment is to bring infinite love and laughter to the world. My resilience allows me to keep on being a loving friend to all as best as I can, regardless of having been deeply hurt. My love for others and creating laughter fuels me. Seeing people smile and laugh and cry from happiness gives me great joy and meaning. I can remember performing in Times Square often while living in the city, and people from the audience, visiting from all over the world approaching me after shows thanking me for being the highlight of their trip to NYC.
Contact Info:
- Website: www.michaeloldroyd.com
- Instagram: @thedroyd
- Facebook: https://www.facebook.com/Michelangeloldroyd/
- Linkedin: https://www.linkedin.com/in/michaeloldroydpro/
- Youtube: https://www.imdb.com/name/nm6358378/?ref_=fn_al_nm_1
- Other: imdb.me/TheDroyd
Image Credits
Nate Roscoe, Sean Stratton, Ben Mead