Work Relationships and Mistakes: Joe Perello on Leadership and Learning Culture

CEO of Props -- ⁠Episode page with video, transcript, links and more⁠

My guest for Episode #196 of the ⁠My Favorite Mistake⁠ podcast is Joe Perello, president and CEO of Props, a first-of-its-kind, marketing technology platform enabling DTC brands. Joe is also a member of the board of directors of New York Cruise Lines.

Prior to Props, he co-founded and led an NYC-based digital agency and bootstrapped it into an award-winning shop.

In 2003, Mayor Michael Bloomberg appointed Joe as the first Chief Marketing Officer of the City of New York. Joe and his team created the first self-funded marketing and promotional engine in the City's history, generating more than $100 million and paving the way for unprecedented results in tourism.

Joe was the Vice President of Business Development for the New York Yankees during some of their most successful seasons, reporting to the late George M. Steinbrenner.

In this episode, Joe tells his favorite mistake story about a “work divorce” that was “really hard” — was it a mistake to separate himself from a company and certain workplace relationships? How did he learn to take responsibility for those relationships? We also discuss how to create a culture of learning from mistakes and creating an environment where you can be wrong.

Questions and Topics:

• Work divorces are hard… it WAS the right thing to do
• Felt like it WAS a mistake as it happened – turned out to be best…
• Fear — no idea what I was going to do next…. — uncertainty or a mistake
• It’s always a judgment call – a mistake or not??
• The founder dynamic made it more difficult – personal pride
• Lessons learned to prevent future work divorces??
• Culture of learning from mistakes? “Create an environment where you can be wrong…”
• Getting things wrong helps us get it right??
• “I don’t want to be right I just want to win”
• Direct marketing – test and learn, test and learn
• Fail fast, fail often?
• Props – how did the company pivot??
• Mistakes that marketers make? Being inauthentic or failed attempt at authenticity that didn’t ring true?
• Mistaken perceptions of the late George Steinbrenner… public perception vs reality?

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