The Artist as Entrepreneur – an Interview with Rob Santos – Comedian

Written by Rinnie Orr

Last week, I had the privilege to chat with a very special friend, comedian Rob Santos. 

Rob has been performing comedy since he was a kid and in 2008 he decided to move to New York City to really learn and hone his craft. While out in the city putting in the work to the be the best comedian he could be, his daughter (who is way more dope than he is) decided to show up and change his life for the better. Due to the shift of the amazing life event of becoming a dad, he moved back to Hartford in 2012 to excel as a man, as well as a stand up comedian. He is widely known as Connecticut’s Dave Chappelle due to his raw, honest, and insightful brand of humor. 

Rob has created a web series in Connecticut titled Beige on Both Sides which the Hartford Courant praised as an up and coming web show for their area. He is now currently in the process of rebooting the show entitled “Beige” where it has received much praise in the greater Hartford area. 

Rob has also developed the web talk show “Toilet Time” on YouTube and Facebook where he interviews stand up comedians and musical guests in his bathroom. The show was also in development for a pilot in the Hartford area. 

Other accomplishments that Rob has thus far are being the winner on Amazon’s Comic’s Watching Comics, the amazing success of his comedy/music concert show Rob’s Speak-Easy, being a regular comic at some of New York’s best comedy clubs and being on various Sirius XM radio shows. Additionally, he’s been a mentor to many comics and performers in Connecticut and Massachusetts. But his most important accolade is being the father of an amazing 9-year-old girl.

I’m so happy to sit down and talk with Rob. He has graciously agreed to fly to North Carolina to be part of our WEBB Squared launch and fundraising gala in October. We’re so excited to have him be with us for that event.


The Interview

Rinnie: Hey Rob, I’ve known you for a few months now through our Commonwealth Network of heart-centered entrepreneurs. While it’s a really great group, I think that there are some particular challenges of entrepreneurship when you are an artist such as yourself. Your business is selling yourself. 

Maybe you can start by telling me a little bit about yourself. Who are you, Rob? Who are you at the core, deep down? Share whatever you feel comfortable sharing…

Rob: Wow, okay…

I am someone who’s always thought of myself less than what I really am. I’ve always been too hard on myself. I know that I have the ability and the social skills to be great – but I’ve always put myself down at the core. .

That’s me – now – in that regard. 

Also, I’m a dad at heart. I have a nine-year-old little girl named Brooklyn. 

When I think about it, the two places where I feel most comfortable and most safe – where I feel 100% myself – is when I’m with my daughter and when I’m on stage performing  talking to people.

 How did you get started with being a stand up and comedy? 

 I was totally infatuated with it as a kid, since eight or nine years old. As I got older, I just started performing on street corners for homeless people in my hometown.

By the time I was about 14 or 15 years old, I got on stage. Comedy just sunk in. It was my everything. I didn’t want to do anything else.

Compared to where you started, how have your dreams and aspirations changed?  What are your current dreams and aspirations?

When I was young and doing comedy, it was something I just wanted to do.  I never shied away from that goal. It wasn’t until I moved to New York City, though, when I realized that it could be a real possibility. I saw an opportunity to get to another level. But there was also a lot of shady things that were happening. I felt like I wasn’t reaching my potential in New York City. 

When I came back home to Connecticut, I started getting help with my mental health. I started learning to be a man, how to be a good father, a good husband, a good person, a good boyfriend, a good person to my girlfriend. That’s when everything opened up. I was able to see who I was.  I was able to see that the New York route wasn’t for me.  I started learning how to hold myself accountable, and also how to promote myself differently. And I really started on myself more so than getting on stage.

As an entrepreneur – what kind of things do you have to do to promote your work and to sell yourself? What are some of your strategies you’ve developed to promote yourself as an artist and comedian?  

Honestly, thank God for social media. Before social media, you had to go through gatekeepers. They’re still there – you had to go through New York City and Los Angeles, – the bigger cities where there are bigger markets, opening up. But with social media, you can be in Milwaukee, Wisconsin, and still be just as big – if not bigger – than someone who’s been doing it for 20 to 30 years. 

With social media, you’re building it from the ground up. What I’m doing now is building myself locally, regionally and internationally. Locally, I’m strong. And now, meeting you guys, I’m expanding further out nationally. I’m starting to expand regionally – not just in Connecticut – but also New York, Massachusetts, and Rhode Island. It’s all because of social media. That’s what social media helps with. That’s what I’ve been using to promote myself and get people to see who I am. 

Do you have any advice for other comedians, artists, people who have to promote themselves as part of their business?

Yeah…if you’re going to be an entrepreneur as an entertainer, don’t do it because you want to get paid. Also don’t do it so you don’t have to get a “real job.” Because it is a real job – and it is hard enough on its own. 

Let your career grow naturally. Don’t push yourself into a situation that you may or may not be ready for. You don’t want to put too much pressure on yourself.

Understand who you are.  Know your intentions – know what you want. Write down your goals. Remember that staying the course is the biggest thing. There’s gonna be some days that will  be awful. They’re gonna suck. But as long as you stay the course, the person you are supposed to be will be. Also keep an open mind, because you may not be a stand up comedian – you might turn into a promoter or an actor. Just keep an open mind -because you never know where this business can take you.

There’s one more thing I want to mention. Most people don’t see the nuts and bolts of what we do as artists.  We often don’t know our value – and fall into extremes – we may overvalue ourselves or undervalue ourselves. It’s important to figure out a way to know what our value is and know what we bring to the table. 

There are times I don’t believe in myself enough. I mean, you guys invited me to North Carolina. But it’s a little bit scary. I want to be seen as a professional. You guys see me as a professional. So me coming to North Carolina means everything – it’s gonna change who I am – not just as an artist, but as a man. We’re going to have our moment and do our thing. But after that, everything’s gonna change for me. I believe that wholeheartedly. 

What I’m trying to say is I want all artists to believe that as well.

Right? That it’s okay to take a risk once in a while – that the risk will help you grow and help you get to the next level, even if you don’t know what the next level is. 

 Yes, as an artist, you’ve got to trust in yourself. Many people have said the same thing to me “Rob, you got to trust yourself.” 

And I’m having faith with you guys –  I can’t wait to experience what you guys have to offer.

Yeah, we’re gonna have a good time. We can’t wait to meet you in person.

All right, let’s finish this up with a few rapid fire answer questions. Don’t think too hard – just answer quickly what pops in your head. Question #1 –  what’s your favorite day of the week?

Wednesday because it’s the one no one likes.

Where’s your next vacation going to be?

Either Greece or Nova Scotia.

 Okay. Do you listen to podcasts?

Not so much, but I do. I listened your podcast, The Remedy.  I’ve listened to Howard Stern a lot. 

Okay, what’s your superpower?

Being able to control my emotions.

Who’s gonna play you in the movie version of your life?

This young kid I know named Noah. He’s a very, very funny kid.

Are you a morning or night person?

Oh, man, I’ve noticed that I’m a little bit of both, actually.

What fortune would you like to get from a fortune cookie?

Keep on the path.

All right – a couple more question – Andy Warhol said that every person will get 15 minutes of fame. What are you going to do with your 15 minutes?

Make sure that I am famous enough in that moment so that people will know who my daughter is.

What terrible movie do you love? 

Beautician and the Beast. Oh, great question.

 And then your final question, what is your catchphrase?

 I’m actually wearing it on my shirt right now. “Let’s get these hoes.”

When I was a kid, this guy I knew said it in a derogatory term. I wasn’t a fan of it. So, I just figured out use it in reference to garden tools. 

Okay that’s a wrap. Look forward to meeting you in a couple weeks.

You’re so kind. Thank you so much for being so kind.
Yes, for sure. Thank you so much. Take it easy. Bye.

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