Q: Kindly give our readers an introduction to your business. Please include what your business is all about, in which city you are located and if you have offices in multiple locations/ cities.

A: The Comedian Company is the largest booking agency for stand up comedians in the USA. We specialize in comedians for corporate events. With a database of over 2,000 comedians from coast to coast we pride ourselves on being able to book a comedian anywhere in the U.S. and Canada. We have offices in Michigan, Minnesota, Florida, and New York.

Q: Kindly give us a brief description about yourself (it should include your brief educational or entrepreneurial background and list some of your major achievements).

A: Jason Douglas began doing comedy in 1998 at the age of 18. To date he’s appeared on several TV shows, worked casinos in Las Vegas and appeared on cruise ships. In 2002 he started The Comedian Company with a dream of revolutionizing the comedian booking business by changing the way “things had always been done”. He modeled The Comedian Company after a tech company and looked for ways to make the process easier for both the customers and the comedians. By 2007 The Comedian Company was the largest booker of comedians by volume in the USA.

What inspired you to (start a new business venture) or (to make significant changes in an existing business)? How did the idea for your business come about?

A: As a comedian I wanted to make the process easier for both the comedians and the customers. Comedy should be fun – Not hard. I saw so many issues with the way things were being done by the regional booking agents that I knew adding the technology factor and routing comedians nationally would revolutionize the way things were done.

Q: What three pieces of advice would you give to budding entrepreneurs?

A: Learn from others – both their wins and loses.

Set realistic goals and work to beat them.

If you’re not passionate enough to work 7 days a week at first then you don’t have the passion your business needs.

Q: What would you say are the top three skills needed to be a successful entrepreneur?

A: Passion. Determination. Common sense.

Q: How many hours do you work a day on average?


Q: To what do you most attribute your success?

A: Working harder than my competition.

How do you go about marketing your business? What has been your most successful form of marketing?

A: Non stop advertising on all platforms – internet, print, social media, etc. We encourage our comedians to help market. That gives us 2,000 sales people. We’re one team.

Q: Where did your organizations funding/capital come from and how did you go about getting it? How did you obtain investors for your venture?

A: I started this company with my life savings of about $5,000. That didn’t go too far but for the first three years I put all my profits back in to the company.

Q: What is the best way to achieve long-term success?

A: Think about your industry and where you see it going one, five, and ten years down the road. Like chess you need to be thinking many moves ahead all while anticipating the market, your competition, and other factors you cannot control.

Q: Where you see yourself and your business in 5 – 10 years?

A: Steady growth. Taking a larger piece of the market share each year. Developing new talent!

Q: Excluding yours, what company or business do you admire the most?

A: Tesla. I often tell people my goal is to be the Elon Musk of stand up comedy. I want to disrupt the industry and give the customers a better experience.

Q:How important have good employees been to your success?

A: A staff you can trust is key. It took me years to find the right group and when I did my business exploded!

Q: How long do you stick with an idea before giving up?

A: Depends on the idea. If I’m passionate, years!

Q: What motivates you?

A: Several things motivate me to get up at 6:00am each day. # 1 Generational wealth for my family. # 2 Helping my fellow comedians work and support themselves and their families. # 3 Bringing people laughter.

Q: What are your ideals?
A: I’m someone who sticks to their word. That’s the most important ideal or value for me.

Q: How do you generate new ideas?
A: I just let them pop in my head naturally. When an idea pops in your head write in down! Don’t forget it. 99/100 times it goes no where but there is that 1 time that makes it worth it.

Q: How do you define success?
A: I define success as being financial able to never work again if I choose. When you work because it’s a passion it’s way more fun. My biggest success is helping comedians work every week. It’s a great source of pride.

Q: How do you build a successful customer base?
A: Keep them informed in every step of the booking process. Make sure they feel comfortable. Follow up with them after the event too. People want to feel appreciated. I’m grateful for each customer and they know it.

Q: What is your favorite aspect of being an entrepreneur?
A: The ability to succeed or fail based on my own ideas.

Q: What has been your most satisfying moment in business?
A: When famous comedians started to come to me looking to expand their work. That’s when I knew I had made it.

Q: What do you feel is the major difference between entrepreneurs and those who work for someone else?

A: Risk tolerance maybe? I think most people have the entrepreneurial spirit somewhere in them.

Q: What kind of culture exists in your organization? How did you establish this tone and why did you institute this particular type of culture?

A: First and foremost, openness. We talk about the good, bad, and ugly. I don’t have time to have things sugarcoated. We communicate daily and all have the same goals.

Q: In one word, characterize your life as an entrepreneur.
A: Fun

Q: If you had the chance to start your career over again, what would you do differently?
A: At the beginning I made a lot of mistakes. I learned from them though which is all you can ask. Only thing I’d change is having more confidence in myself and my ideas.

Q: How has being an entrepreneur affected your family life?
A: I have a wife that flies for the U.S. Air Force. I’m very lucky that because we are both career motivated that we understand each other and encourage each other. As a new father I’m able to delegate things to my staff which helps.

Q: What is your greatest fear, and how do you manage fear?
A: I fear the up and coming hungry kid who wants to revolutionize the business like I did. So, it keeps me from getting lazy.

Q: How did you decide on the location for your business?
A: As an internet based company I was lucky that location wasn’t an issue.

Q: Do you believe there is some sort of pattern or formula to becoming a successful entrepreneur?
A: Hard work multiplied by thinking = success

Q: If you could talk to one person from history, who would it be and why?
A: That’s a tough one … Moses from the bible maybe? Guy had to lead a nation through a desert for 40 years.