Today we’d like to introduce you to Dave Siegel.
Hi Dave, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I worked as a doorman at the DC Improv while a college student in Washington, DC. It was a perfect job for me because it paid me to be able to watch stand-up multitalented times/week. When you’d see a comedian perform four times in a row, it’s a peak behind the curtain as opposed to the typical audience experience, see them once and heading home. You see the nuances, the adjustments, the differences in crowd work and how good they may or may not be off the cuff. It was them that I went from comedy fan to wanting to try it myself.
Cut to about ten years later and I was headlining the same club for which I was once a doorman and recording my album there.
With 20 years of stand-up comedy and television writing experience, in February of 2021, my family and I moved to Boca Raton. It was the luckiest break ever because we closed on our house on March 1, about ten days before the pandemic shutdown.
During the height of the pandemic, we would take family drives and we happened upon the Boca Raton Amphitheater, which is just an aesthetically beautiful space. My wife Stephanie, knowing what I sacrificed in the performing stand-up realm in a move from Manhattan to Boca said “We should produce shows here,” and that’s what we did. The city got very much behind us and the idea and yes, it had major delays and obstacles due to COVID but the end product is amazing comedians from NY and LA coming to town to perform outside in a beautiful setting under the stars.
We even gave it the name ‘Comedy on the Green’ as it takes place on the lawn of the amphitheater but also as an homage to our old stomping grounds, Central Park’s ‘Tavern on the Green.’
We all face challenges, but looking back would you describe it as a relatively smooth road?
There are struggles in launching any business. Now imagine launching one during the pandemic and while both people involved also have separate full-time jobs. I’m a former writer for Anderson Cooper, Don Lemon and Diane Sawyer and currently a writer/producer for Ashleigh Banfield on the NewsNation show ‘Banfield.’
My wife is a former on-air news reporter who runs a company called ‘Reel Media Group,’ which provides media training for journalists, athletes and podcasters.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I’ve been a stand-up comedian for 20 years but for better or for worse, most know me for an original YouTube character I created called ‘White Guy Indifferent,’ who is an unapologetically a-passionate observer. He finds himself unwillingly immersed in various locale and national news packages in which everyone else is losing their minds over anything from Popeyes running out of chicken to the Women’s March Against Trump, but he… just happens to be there… and usually eating a salad as others are losing their minds. WGI has garnered over 60 million views over various aggregators and has caught the attention of numerous celebrities and influencers.
We’d love to hear about how you think about risk taking?
I do wholeheartedly believe in risk-taking. I’m at my most driven in life when tackling a new venture and believe that at the end of the day, success or failure… the work I’ve put in is going to positively impact what I do next. My wife and I have ZERO experience in the hospitality field short of having waited tables in our youths. We are now running this show, dealing with vendors, security, and a million things we never even thought of. The 140 “sling chairs” we marketed for the priciest section of the shows arrived from China 5 days prior to the first show.
One of us was going to get murdered had those chairs not arrived… it was probably going to me despite the fact that the chairs were her baby!
But we took a risk because we didn’t want our show to be a typical comedy experience. We want people lounging under the stars, not in bridge chairs, sharing a table with strangers.
Pricing:
- VIP experience gets you 4 sling chairs in you own little area with your own cocktail table, closest to the stage and it runs about $71 per seat
- The urban picnic gets you a blanket for 2 on the lawn and comes out to about $42/head
- General Admission gets you a more traditional seat for $38
Contact Info:
- Email: [email protected]
- Website: comedyonthegreen.org
- Instagram: Instagram.com/comedyonthegreen
- Twitter: https://mobile.twitter.com/standupdave
- Youtube: https://m.youtube.com/user/dasxxii
- Other: https://www.davesiegel.com/

