Chet Harding

You’re more likely to regret the chance you didn’t take than the chance you did and failed, so don’t let the risk of failure hold you back.


Comedian and actor Chet Harding first began performing at talent nights in high school. He graduated magna cum laude from Amherst College with a major in environmental economics and law in 1992.

During his sophomore year, Chet Harding began doing stand up comedy performances. He entered a competition at the University of Massachusetts and performed very well. That summer, he entered the Boston Comedy Riots competition and came in second place, and that led to him booking stand up gigs at nearby colleges while he finished school.

After graduation, Chet Harding got a job in Chicago working for international advertising agency Leo Burnett. He joined Second City Comedy and began taking classes to learn more about improv.

In 1996, a job offer from Polaroid returned Harding to Boston. He launched the ‘Improv Asylum’ comedy theater in 1998 with two other comedians and left his corporate job shortly after.

Where did the idea for your company come from?

When I moved to Chicago to work for Leo Burnett, I got involved with the Second City comedy club where I took improv classes to learn more. I loved it and wanted to keep doing improvisation when I moved back to Boston but there wasn’t much around for it that I knew of.

I eventually found one group called ‘Rock Hard Improv’, and I started acting with them in the basement of the Hard Rock Cafe. But come Spring, the Hard Rock wanted that room for private parties instead. We then heard about an empty theater in the north end of Boston up for lease. The three of us decided to take a small business loan, lease it, and launched Improv Asylum. It started taking off from there and I left my corporate job shortly after to start directing, acting, writing, and producing at Improv Asylum.

What does your typical day look like and how do you make it productive?

When it comes to running your own business, there is no real typical day. Your day involves anything from maintenance of the theater to business deals to people contacting you about private shows, holding rehearsals, writing, etc. It’s kind of all over the place here, but it keeps it interesting this way. When it’s your own thing, it’s your passion project, and it doesn’t necessarily feel like work even though you are working very hard in a number of different areas, you’re on call all of the time, and there’s no typical to your day at all.

How do you bring ideas to life?

This is something that has significantly changed over the course of 20 years. Initially, if you had an idea and it’s standup comedy, you just kind of write it and put it in your act and see how it goes. And then you’d shape it or tweak it based on audience feedback and what you think might work better. But that could be brought to life by just getting out there and putting it onstage.

When it comes to a comedy ensemble, it’s kind of the same thing but there’s a little bit more vetting of the material with the group.

But if you’ve got an idea, there are more tools now at your disposal to give it a shot, and either an audience will tell you whether it’s good, or a good friend will tell you if it’s good, or for better or for worse, the internet will tell you whether it’s good or not.

What’s one trend that excites you?

I think the idea of virtual reality opens up a world of possibilities for entertainment, and it will be interesting to see how that plays out for comedy. I think there could be a pretty interesting application to do a virtual reality comedy thing where you can have your heavier background, your sets, etc. all within the virtual reality and anybody could watch it from anywhere.

What is one habit of yours that makes you more productive as an entrepreneur?

I think it goes with the core ideas of improvisation, which is to sync with a “yes, and” mindset. What I mean by that is I think we can very easily and quickly have knee jerk reactions to say no or to find why things wouldn’t work. The “yes, and” mindset is much more about, ‘how do I listen more effectively to someone?’ And even if I don’t agree with them or, but I don’t think their idea is the best idea out there, what about their idea can I use and build off of to make an idea that would work? Or what’s the root of their idea and how do I make it come to life?

So I think that, especially as an entrepreneur because you’re looking for ways to find a competitive edge and to keep your business going, it’s important to be in the moment and the mindset of ‘yes’. I think is something that really helps me.

What advice would you give your younger self?

I thought of this question in reverse when I was younger when I had to decide between taking on the potential financial burden of launching a company and leaving a highly paid corporate job to follow a dream. There was a lot of risk involved, but then I thought, 20 years from now, do I want to look back and say, oh, it’s too bad I tried it and failed? Or do I want to look back with regret and wonder why I didn’t try it? And I realized at the time that I would much rather look back and know I tried instead of wonder what if. So I’d tell my younger self that I was right, I did the right thing, and to always keep that mindset.

Tell us something that’s true that almost nobody agrees with you on.

It’s a silly one, but not all Canadians are nice. When I mention it to people, a lot of them come back at me saying, “what are you talking about? Everyone who lives in Canada is really nice.” I will say that the majority of people are, and it’s a much friendlier country overall compared to the people I’ve met in the U.S.

But I’ve done a lot of work with WestJet Airlines all throughout Canada, and they were awesome. The people I met there were awesome, although I will say the Canadian border patrol is not always friendly. I’ve gotten secondarily interviewed a handful of times. Maybe it’s because I had a lot of business there and I was flying in a fair amount to meet with them.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I’ll continue to push an idea instead of settling. I’ll try and find a way we can make it better, keep questioning and saying “what if” because of those what if moments can lead to big ideas. Particularly as you start finding success, I think it can be easy to say, okay, I’ve done it, I’ll put it in cruise control for a while, but I think for a successful entrepreneur you need to keep saying what if or how can I do something better.

What is one strategy that has helped you grow your business?

Once I had people working for me, I think my strategy of letting them do things their own way has really helped. It’s not so much a strategy as a way of handling people, kind of empowering and engaging people to say “you’re important”. I try not to tell people how to do something, just what needs to be done.

Another thing we’ve tried to do along the way whenever I’ve employed actors is to treat people well. We probably could have made more money off of people, paid people less. But treating them well is important because it can come back to you, it can certainly have them engaged longer with you. I think so many times, particularly in our industry, actors aren’t treated very well (unless they’re famous), so I always want people to know that they belong, that they are important, and that I value them.

What is one failure you had as an entrepreneur, and how did you overcome it?

Probably the biggest failure was when we tried to expand to Ireland. We found a theater in Dublin and we thought it would be a great market for comedy because there’s certainly plenty of places that provide comedy there, but nothing quite like an established theater. So we approached the people who ran the theater and made a deal. But when you’re not in charge of your own venue, it becomes difficult. They wanted to have sold out shows from day one, but our approach was much more organic, to build a loyal audience over time.

So the lesson we learned is to really understand that you’re all on the same page as you create a partnership together.

What is one business idea that you’re willing to give away to our readers?

I think the idea of using virtual reality to connect people. For example, instead of people flying to different cities or states for business meetings, you could put on a headset and connect with each other as though you’re in the same room.

And for the entertainment industry, imagine there was a band or performance you wanted to see but they weren’t coming to your city. You could do something like pay-per-view, but instead of paying and watching it on TV, you could put on a headset, put in the access code and then it would be like you were actually at the show or concert amongst the audience. It would be a whole different kind of experience.

What is the best $100 you recently spent? What and why?

It was for an online refresher course for my DiSC certification. I know the philosophy behind it, but I wanted to refresh myself so I could be more up to date with the current trends.

What is one piece of software or a web service that helps you be productive?

Social media and developing digital content is really important for this industry to keep your brand out there. We need to stay on top of it to get our message out in a much more cost effective way, to target our audience better, and to extend our brand personality. We need to be able to engage with people so that they’ll want to be part of our brand.

What is the one book that you recommend our community should read and why?

A Short History of Nearly Everything by Bill Bryson. It gets into a lot of metaphysical things and deep philosophy of life and where we come from. It is sort of a short foray into all of that, and he writes it in a very accessible way… kind of like a Neil Degrasse Tyson sort of way, but not as scientific.

Another is the 2010 Pulitzer Prize winner in fiction, Tinkers by Paul Harding. It follows the thoughts of George Washington Crosby, an elderly man on his deathbed, as he relives his childhood and reveals the life of his estranged father.

What is your favorite quote?

“Well, if you want to sing out, sing out, and if you want to be free, be free, ’cause there’s a million things to be.” – Cat Stevens

“You miss 100% of the shots you don’t take.” – Wayne Gretzky.

Key Learnings:

● You’re more likely to regret the chance you didn’t take than the chance you did and failed, so don’t let the risk of failure hold you back.
● Having a “yes, and” mindset will help keep your mind more open to someone’s ideas and how you can build on them rather than shut them down immediately.
● There’s no such thing as a typical day when running a business.
● Brand personality is important for comedians.