Meet Rich Sheridan, CEO and Co-founder of Menlo Innovations, Author of ‘Joy Inc.’ and ‘Chief Joy Officer’

The first time Rich Sheridan touched a computer was in 1971. The CEO and Co-founder of Menlo Innovations, who went on to write “Joy Inc.” and “Chief Joy Officer,” was then a freshman in high school who instantly fell in love with the idea of writing software.

For Rich, who refers to himself as a “pure Michigan kid,” software was an artistic medium. He started by typing the names and stats of Major League Baseball players into a computer so he and his friends could “play” baseball in the winter. That programming won a contest and essentially launched his career.

He got his first software programming job shortly thereafter and went on to earn degrees in computer science and engineering. But when he entered the workforce, the world of software development wasn’t what he thought it would be.

“It was chaos,” he says. “It was firefighting every single day, delivering poor quality all the time. There is nothing satisfying in that kind of career. I don’t care how much money you make; I don’t care how many stock options are thrown at you.” 

Eventually, Rich became a vice president of research and development for a public company, where he could make the kinds of changes he dreamed of. Unfortunately, he lost that job in 2001 when the dot-com bubble burst, but he took it as a sign to become an entrepreneur. 

Rich founded Menlo Innovations later that year with a mission to bring joy back into an industry that he always thought could, and should, be joyful.

Themes discussed in this episode:

●     The books that influenced Rich’s career

●     The two types of business culture

●     Why Rich hates the word failure

●     Taking action versus taking a meeting

●     Why spending time together is one of the most important ways to build trust

●     How to break out of the "numbers game"

●     Why entrepreneurship is really about self-discovery

Featured Guest: Rich Sheridan

📽️ What he does: Rich is the author of “Joy Inc.” and “Chief Joy Officer” as well as the CEO and co-founder of Menlo Innovations, which aims to bring joy back into software development with a stated mission to “end human suffering in the world as it relates to technology.”

💡 On Gravitas: “When I hear that word, I hear gravity,” says Rich.”Which is [about] grounding. We entrepreneurs have our heads up in the clouds. But it’s our feet on the ground, taking one step each day, held down by that gravity, that’s important. It keeps us connected to reality.”

Episode Highlights

Timestamped inflection points from the show

[4:34] Origin story: Rich discusses his upbringing as a “pure Michigan kid,” how he got started in software and how he knew the industry needed a change.

[8:49] Becoming an entrepreneur: When Rich lost his job in 2001, he knew it was time to make the change he always wanted to see, so he started Menlo Innovations.

[12:20] When teacher becomes student: Rich’s advice to leaders: Read more books. He encourages us to “become students again.” He also touches on unlocking your dreams when you’re stuck in a rut.

[17:29] Clash of two cultures: The way Rich sees it, it’s important to distinguish between two types of business cultures — the “intentional” culture and the “default” one. He explains that, often, default cultures lead to “hero-based cultures,” in which the only way to scale the hero is by [working] overtime. 

[19:51] Run the experiment: It’s a given that experiments don’t always work, but that shouldn’t be a reason to stay within the company comfort zone. Rich shares an example of why running experiments is so important — and how he got his team on board to try something new.

[24:47] Nobody’s perfect: Rich doesn’t like the word fail. In fact, he encourages his team to “make mistakes faster.” Here, Rich explains why making early, small mistakes can help in the long run.

[29:23] Building trust: Rich says the only way to build serious relationships is through quality, in-person time. “You don’t get to build trust by just waving your hands, saying, ‘Okay, guys, let’s get past the trust thing. We all trust one another,’” he explains. “No, that’s not how trust works. We literally have to spend time together.”

[36:05] Avoid Groundhog Day: If you’ve ever felt like you’re Bill Murray in “Groundhog Day,” you’re not alone. Most of us have the same daily routines, but that monotony does not lend itself to new ideas. Rich talks about WeWork and the benefits of new “office” environments.

[46:04] Fear is just a four-letter word: Rich has a simple motto for transparency: “Fear doesn’t make bad news go away. Fear makes bad news go into hiding.” Here, he dives into the importance of frequent transparency and communication.

[57:56] A journey of self-discovery: Many careers, especially those that involve entrepreneurship, are a journey to self-discovery, Rich says: “The easiest place to identify where to start is the hardest place to begin, and that’s inside of you.” 

[1:03:26] On Gravitas: When asked what gravitas means to him, Rich talks about being grounded and taking one step at a time.

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