We’re excited to introduce you to the always interesting and insightful Cristian Ossa. We hope you’ll enjoy our conversation with Cristian below.

Cristian, thanks for joining us, excited to have you contributing your stories and insights. Are you happier as a creative? Do you sometimes think about what it would be like to just have a regular job? Can you talk to us about how you think through these emotions?

I tend to go back and forth on this one. I have worked in restaurants since I was 15. I love interacting with people and having conversations I am a very extraverted person. I went to college to study psychology and education but after I graduated I was sort of fearful of falling into a career right away. I associated it with being tied down and unable to feel ‘free’ so I started working at a restaurant in Manhattan. The late nights and weekends never usually bothered me, I perform and host comedy improv shows now and I feel like working at a restaurant makes it much easier to connect with people and sell tickets. However I have always wondered what the 9-5 life would be like. I am 25 and my friends are starting to settle down, they have weekends off, holidays, vacations, healthcare benefits which is a life I am not accustomed to. I feel envious from time to time but then I remember that I do love the path I’m on and I have certain benefits that they don’t, for example my job has little ‘take home stress’ and the weeks are pretty flexible. It also has allowed me to get this improv group off the ground which I am very blessed to have. I could definitely see myself in a ‘regular’ job but I’m not sure I’d have the same start to the improv group because I would have had less time and energy. I am happy as a creative when my vision is executed but with improv it’s always up to the spur of the moment.

Cristian, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

So I run an improv comedy group called WiseGuise comedy and we are slowly but surely growing. The shows are very similar to Whose Line is it Anyway, we play about 90 minutes of improv games and that’s our show! We have a written sketch in the beginning and a few singing elements like a doo wop game and a freestyle rap game which always get the crowd excited. Audience participation is not required, but it is encouraged. And people always love it when audience members go up and make fools of themselves. We started out by renting a garage in my hometown and we actually sold out that 50 person show, and then we did shows every few months. The next year we performed at the Stress Factory comedy club in Jersey and since then we have performed at various restaurants and comedy clubs in Jersey City, Rutherford, Manhattan and soon Astoria. I did improv in high school and I started a group in my dorm in college and when we graduated I said hey lets keep doing this so I grabbed my friends and we started doing shows. This year we did 9 shows in the span of 6 months which is the most we have done yet! I am now looking into a production team to revolve around the shows like lighting people, sound people, stage managers etc. The shows are super fun and I have big plans that are finally going into motion. We rehearse usually once a week and the shows keep on improving

What’s the most rewarding aspect of being a creative in your experience?

Recently I looked back in a box of old programs I made for shows and it really puts it into perspective seeing how things used to be. I certainly get in my head a lot and feel stuck or taht I am making no progress but that’s because I am typically comparing myself to who I was yesterday or a week ago. When I look back a few years, the growth becomes so apparent. We used to do shows in a schoolhouse in my hometown and now we are selling out bars in New York City and it took us under 2 years to do this. We also just had a show last Friday and afterwards a few people came up to me and asked if they could get involved. Whether it be as a performer or behind the scenes but in that moment I thought: damn I have created something that now OTHER people want to be a part of (and I don’t have to beg them to be a part of it!).

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

I always feel motivated when I’m reading or listening to Malcolm Gladwell. I think as a creative you can’t really use traditional thinking methods especially when it comes to building a brand. To be honest we haven’t boomed yet but I am sure it’s coming.

Contact Info:

• Website: https://wiseguise.godaddysites.com/
• Instagram: @wiseguisecomedy

Image Credits

Cristian Ossa, Gabe Beltran, Collin Nuccio, Caroline Wall, Monty Harris, Michael Leitner