Matt Ruby Gets Overit: Key Takeaways and Actionable Advice

Matt Ruby Event

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The team at Overit was excited to interview Matt Ruby in our state-of-the-art studio. While a comedian, Matt has also been on the ground floor of some impressive companies. So, he had a lot of insights that can help brands be disruptive in their industries.

Who is Matt Ruby?

 He was the first employee at the project management software Basecamp and developed a cult following (that continues to grow) with Vooza, the video comic strip about startups and the tech world. His contribution to the book “REWORK” should be of interest to anyone in business, as well as how to change careers and follow your passions.

His specialty is taking drab tech/business topics and making them interesting and accessible to regular people.

He also just happens to be a world-famous stand-up comedian. His comedy has been filmed by Comedy Central, MTV, NBC/Seeso, and FOX and his most recent special Feels Like Matt Ruby (“funny” according to The NY Times) is available on YouTube.

His two albums, Feels Like Matt Ruby and Hot Flashes are in regular rotation on Sirius and also went top 10 on the iTunes Comedy charts. He’s also been featured on CNN, The Huffington Post, New York, and Time Out.

He also produces the Rubesletter, a weekly newsletter that perfectly blends Matt’s comedy and deep musings from his vast life experiences.

Overit Interviews Matt Ruby

Our very own Michelle Dinsmore interviewed Matt in Overit’s awesome yet intimate recording studio. This post outlines the key takeaways, but we highly recommend you watch the interview.

How to Put Your Ideas Into Writing

Writing things down is the basis of all ideas. Carry a journal with you wherever you go, who knows when inspiration may strike!?

Writing down your ideas can lead to creative new campaigns, a book, new business models, video ideas, and more.

Matt writes a lot of ideas in his phone, so if this is more your style than carrying a journal, it’s proven to work. “I’m able to capture in the moment and in flow, and then if it sticks around or seems worthwhile, eventually turns it into something.”

Promoting Your New Ideas

As an early employee of Basecamp, Matt Ruby had to help market the new brainchild and offered “the way we would promote ourselves was by teaching other people how to do what we had done.”

If you have an idea and a small budget, there are many things you can do to promote your vision, and like Matt said, you can teach through your marketing content.

Become a thought leader in your industry by offering educational and thought leadership content. Teach your target consumers how to get ahead, and they will be loyal to your brand. Matt did this through blogging, making videos, speaking at conferences, and even writing books.

Open Yourself to New Ideas and Experiments

Matt has been so successful at so many things, and he’s truly an inspiration.

From starting a band to starting a tech start-up to stand-up comedy and so much more, Matt is proof that if you’re open and willing to be a risk-taker, you can succeed in anything you choose.

That lines up well with Overit’s philosophy of disruptive marketing. Doing something different to stand out from the noise and resonate with a particular audience.

Trying new things in your industry leads to authentic and actionable results.

Don’t Be Afraid to Fail

As we just mentioned, you need to keep yourself open to new ideas and experiments, this gives you room to fail. However, don’t be afraid to fail, as it’s a great learning experience that clues you into what works with your audience and what doesn’t.

Matt said, “it’s a willingness to be bad at stuff and to fail. I think a lot of people have success, and then they get sort of accustomed to that.”

Maybe what you’re doing now is successful, but if you experiment with riskier strategies, you may see even more success.

Matt has always been a risk-taker in his endeavors. Even if the future was uncertain. 

Be Funny When it Makes Sense

Matt pushes the boundaries with his comedy, and it made us here at Overit think, how can we help our clients be funny without risking their reputation?

A word of caution from Matt, “And comedy really doesn’t age well. You kind of want it out as soon as possible. And then it also limits the viewership. A lot of times, especially with comedy and for comedians, just being on YouTube and getting as many views as you can is actually the wisest path.”

Your Community Matters

When you have something to say through your content, it matters which platforms and communities your brand is part of.

In terms of Matt’s own community, he explained, “because really where we’re monetizing, or what we’re trying to do, is get butts in seats on the road and sell tickets. And so the more people seeing your stuff, the more tickets you can sell. And that’s actually sort of a wiser path. So I think it’ll probably wind up on YouTube because I think it’s really good, and I would like to get as many eyeballs on it as possible.”

Think outside the box when engaging your audience. Human beings don’t scale online the way Facebook wants you to believe. Get out and see your fellow humans in 3-D for authentic experience and connection. Nothing replaces that kind of share. 

Disruptive and Risky Content Can Speak for Itself

Matt gets a lot of organic PR because his ideas are so unique. We aren’t saying don’t promote your new campaigns and initiatives, but to also realize the fact that disruptive content gets noticed and shared more than standard content.

Matt summed up his thoughts on this topic: “I’m probably too lone wolf about stuff. Like sometimes, I think it would be helpful to collaborate more with others and the promotional side of things. But I’m always surprised when people notice whatever I’m doing and happy about it and confused.”

If you can check the boxes of content that is surprising, truthful, and provocative, that is the magic sauce.

Do Experiments and Gather Information

When you try something new, compare it against previous concepts. Constantly experiment and analyze the data.

Matt’s experience with experimenting: “I think that’s been a mindset that has branched out to other modes of thinking or acts of creation or things like that.  Being like, okay, that joke didn’t work, but if the setup working okay… “

At the end of the day, we can all take a page out of Matt’s book and be risk-takers with how we promote our brand. This also requires a data-driven approach and lots of experimenting. Lastly, Matt is a good reminder to keep things funny when it makes sense!

Are you interested in doing a live event at Overit’s Studios just like Matt Ruby did? Contact us, and we will help you create an event that is prolific.