Founder Focus: Startup Comedian, Matt Ruby

By | 2018-05-11T14:34:17+00:00 March 29th, 2016|Startup Culture|

It was a mid-week evening in the Chelsea neighborhood of Manhattan, a boisterous crowd assembled in the basement of the Meatball Shop for a networking dinner, and who did I get seated next to? The comic startup founder, Matt Ruby. I’m a cheap laugh and Matt is darn funny. And the fact that he pokes fun at startups, the perks of startups (free lunch anyone?) and the terminology of startups, is, well, endlessly funny, which is good for Matt, as the global fixation on startups keeps delivering up quality material for his video production company, Vooza.

I’ve previously interviewed Matt on why creating great video content was essential for brands (doh! video and mobile are eating the world). Here were a few of the tips Matt offered up during that interview for really connecting  with your audience by using video on mobile:

  • It is always about the audience first. Figure out who you’re trying to reach with your content and then start creating your content from there.
  • Plan to roll out a lot of high-quality content, consistently over time. Sorry, there are no shortcuts to building up real audience.
  • Be able to answer this question: “Why would people want to share this?” If people don’t share your content organically, it is unlikely to go far.

Meet the startup founder, with a wicked sense of humor, Matt Ruby.

Q: You’re the founder of the “the Spinal Tap of startups”. What’s the story behind Vooza?

A: I’ll make it quick: I was employee #1 at 37signals (now Basecamp) and began doing standup comedy while employed there (still do too). I then started making funny videos. Then I started making funny videos about the tech world at And guess what happened next? The site goes viral! I then started selling ads and sponsored content on the site. Then another funny thing happened: clients (such as Turkish Airlines) started hiring us to make funny videos for them. Now I have realized I own a video production company that makes funny videos. Phew!

Is Vooza your first startup venture?

I was at 37signals at the very beginning. It was an interesting ride! And I’m still pursuing a startup venture.

Colleges students and new grads are encouraged to take their first job in a startup, as it is a great training ground and opportunity to take on lots of responsibility. Any advice you can provide on being an early-stage employee?

Get equity or die tryin’. Also, don’t make it your entire life. If it bombs, you’ll regret losing those years of your life.

What’s the best trait in a collaborator or team member?

Self-sufficiency. Nothing better than someone who can “own” a project and get things done on their own without lots of handholding. Also, it’s nice if they like Tom Petty and/or Mitch Hedberg.

I know we’re obsessed with our mobile devices and a big part of that obsession is the consumption of video content. With that in mind, what’s the real reason “why” companies should have a mobile video strategy for connecting with customers?

The phone is the medium. That’s where people consume content. You can ignore it but you’ll get left behind.

What makes for great branded content?

80/20 in favor of making great content over mentioning the brand. If it’s too over-the-top product pluggy, then people will tune out. Also, work with pros. You wouldn’t let comedians do your programming yet lots of companies think programmers/marketers/CEO/etc can be performers.

When are you working at your best?

Onstage at a standup comedy show in front of some tourists after a shot of bourbon.

I assume you, like the rest of us, get distracted by instant messages containing cat videos. What’s your trick or tactic for getting back on track after a distraction at work?

I like this app called Freedom. You type in a number of minutes and it keeps you offline for that time. Then again, it’s pretty damn ridiculous that I now pay someone to take the internet AWAY from me. Sigh.

What’s your favorite gadget at the office?

I don’t really do gadgets. I’m proud to be an extremely late adopter. However, I do love my Keysmart keychain.

Is there a productivity app or tool you can’t live without?

I like Evernote and TextExpander and Airfoil.

What’s the one thing at work everyone takes just a little too seriously?

Mission statements. Get back to me when any of these silly apps actually “change the world.”

Any suggestions on how to handle that really awkward moment when a joke falls flat?

Enjoy it. Few things will make you feel as alive as intense shame.

If you weren’t doing what you’re doing now, what occupation would you pursue?


J. Kelly Hoey is a problem solver who believes that most professional challenges—whether funding, landing a board position or getting a new job—are solved by tapping into networks.Kelly is a popular speaker on networking, community building and investing issues, especially as they relate to women, and has worked with the IEEE, PGA, Bank of America, Apple and countless others. Follow Kelly on Twitter @jkhoey and on Instagram @jkellyhoey.