Matt Ruby on How to Build Workplace Relationship Trust

In Chapter 2 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Do You Establish Trust When Building Relationships?" Ruby finds building trust in the workplace comes down to communicating honestly and openly with others, from editors to clients, in a way he also would like to be treated. For him that means getting and giving constructive feedback that comes across not as criticism but as a sincere way to help others improve their work.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on How Filming a Web Series Advances Comedy Career

In Chapter 3 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Has Building the Vooza Web Series Opened New Possibilities in Your Comedy Career?" Creating nearly 100 webisodes for the Vooza online series teaches Ruby new skills, from screenwriting and acting to filmmaking and producing. Working on Vooza gives him skills and a growing confidence he can use to continue his work as well as to work on a pilot for a new comedy series.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Creating New Ways to Help Comedians Make It in Comedy

In Chapter 4 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Do You Enjoy Most About Creating Ways to Help Other Comedians Succeed?" As a comedy screenwriter and producer as well as an organizer and host of several standup comedy shows, Ruby finds happiness giving people trying to make it in comedy a chance to thrive and succeed. He enjoys the experimentation that comes with working with creative comedic talents and finds ways to build upon doing it booking standup acts by casting comedians in acting roles.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Being Comfortable Not Getting Asked For Advice

In Chapter 5 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Have You Learned to Give Better Advice When People Ask You For Help?" Ruby shares how he is not often approached for advice. He finds it may be due to coming across as unapproachable or doing work that is not fully understood by others. While Ruby does not try to avoid people, he shares that not being asked for advice is fine with him and allows him to be left alone.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Learning to Act in a Comedy Web Series

In Chapter 6 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Have You Approached the Process of Becoming an Actor and Acting in a Comedy Series?" Ruby shares how he has transitioned from performing on stage as a standup to acting on film for a web series. After taking Meisner acting classes, Ruby learns by doing and working through the process of acting in Vooza webisodes. He finds acting on camera more nuanced than performing on stage in front of audiences and adjusts his approach accordingly.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Creating Web Series Characters for Comedian Actors

In Chapter 7 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Have You Found Most Interesting About Creating New Characters for Other People to Play?" Writing comedy for Vooza, a web series satiring startup culture, Ruby finds creating characters for standup comedians to play is about understanding their strengths and building structure in the role to bring out their best in both scripted and unscripted moments.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Developing Characters for a New Comedy Series Pilot

In Chapter 8 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Are You Challenging Yourself to Improve as a Writer?" As a comedic screenwriter working on a new comedy series pilot, Ruby learns to write characters that balance being grounded in reality with being absurd and silly. He avoids writing canned jokes and instead focuses his screenwriting to make fictional characters more human, relatable, and approachable.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Two Ways to Improve Comedy Screenwriting Skills

In Chapter 9 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Skills Are You Working on Right Now to Become Better at Your Job?" Ruby shares two ways he is improving as a comedy screenwriter. First, he finds it helpful to invite feedback and give ownership to his creative team of writers and actors. The added ownership gives his team an opportunity to personalize the characters and scripts to their strengths. Second, Ruby works on building better narrative arcs to improve story flow and structure. Working on short-form web videos averaging three minutes, he finds that structure makes the storyline more interesting and the characters more compelling.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Learning the Nuances of Filmmaking and Scriptwriting

In Chapter 10 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Experiences in the Past Year Have Most Influenced the Direction of Your Work?" Producing the Vooza web series, Ruby finds it educational learning from experience creating webisodes and evolving the tone when writing new segments. As an established standup comedian now working in a screen format, he also learns nuances of presenting comedy in a video medium and the filmmaking styles, such as cross-cutting, used to do this well.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Improving Web Comedy Project Collaboration

In Chapter 11 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Have You Found to Be the Keys to Creating More Successful Project Collaborations?" To start, Ruby finds it essential to be working with a funny idea and script. If this core is not in place, then no amount of funding or talent will make the comedy program funny. Once the core is in place, Ruby finds building more successful collaborations is about giving creative team members ownership to feel part of creating a good work product.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Building Team Chemistry Filming a Comedy Series

In Chapter 12 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Are You Learning to Work More Collaboratively With Different Personality Types?" Ruby finds it critical to build teams that believe in the project and have a willingness to be open and experimental on the film shoot. From the cast to the director to the cameraman and sound engineer, Ruby sees this shared value as a non-negotiable when filming, no matter how different a film team may be.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on How Repetition Improves Creative Team Dynamics

In Chapter 13 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Are Your Team Dynamics Changing as Your Company Completes More Creative Projects?" Ruby shares how going through the process of learning how to plan, shoot and produce a web series has incrementally built team confidence. Over time, the creative film team develops a rhythm working through nearly 100 episodes.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Running a Profitable Online Entertainment Startup

In Chapter 14 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Does It Mean to Be a Leader in What You Do?" Ruby compares what he is building at Vooza with an entrepreneur story about starting a lawn care business. The lawn care business grows slowly and makes money but does not receive attention because it is not glamorous. In the same way, rather than raising venture capital and measuring success by whether or not a major network picks up his show, Ruby takes a nontraditional route, building a profitable online business selling branded content episodes for a web series.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Handling Work Pressures of Making People Happy

In Chapter 15 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Does It Mean to Perform Under Pressure in the Work That You Do?" For Ruby, work pressures from writing and producing a web series comes down to making people happy. This encompasses both client relationships and keeping them happy with the branded content and product placement advertising he creates as well as audience relationships and keeping them consistently entertained.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on How to Build an Online Community for a Web Series

In Chapter 16 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "What Has Your Experience Developing Vooza Taught You About Building an Online Community?" Ruby finds two things are key to building audience relationships: having a consistent frequency of contact and staying open and approachable to communicating with his audience. The challenge with these online marketing initiatives is to find the time for them amidst the many other parts of the business.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on Monetizing Web Video With Branded Content Advertising

In Chapter 17 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How Did You Decide to Make Branded Content and Product Placement Central to the Vooza Business Model?" By talking to advertisers, Ruby learns they are more interested in product integration into web series episodes than in running pre-roll advertising. Ruby finds this also benefits his audience, who is more accepting of branded content and product placement than of 30-second block pre-roll commercials.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on How to Find Branded Content Advertisers for a Web Series

In Chapter 18 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "In television, we see the big automotive brands making big plays and obviously there is an Apple computer in every HBO show, but you also tailored your branded content and product placement to your audience with Vooza. So how did you go about finding the right fit for potential advertisers to put on a show?" Ruby shares how finding advertisers for his web series starts with reaching out to people to start a conversation. From there he has been able to find people doing similar projects and websites and look at who is advertising with them. As he has built audience and advertiser relationships for branded content and product placement, Ruby returns to existing relationships - people who understand his business - for new campaigns and projects.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University. 

Matt Ruby on How to Improve a Web Series Business Model

In Chapter 19 of 19 in his 2014 Capture Your Flag interview, standup comedian and Vooza founder Matt Ruby answers "How is Your Company Business Model Evolving as You Gain Experience?" Ruby finds he is evolving his business model by simplifying it. He reduces the number of options he offers potential clients so when writing a one-page proposal, it is even more clear what the client gets and how much it costs. As the company grows, Ruby and his team experiment with viewer subscription options to complement advertiser revenue streams.

Matt Ruby is a standup comedian based in New York City. He also founded Vooza, on online comic strip web series that makes fun of tech startup culture. As an actor, director, writer and producer, Ruby leads the creative direction for the team. Before his comedy career, Matt was employee #1 at 37Signals. He graduated from Northwestern University.