Virtual Event Recap
During a recent private LEAP Alumni & Community virtual call, members gathered for a candid conversation with Nick Tran, President of CÎROC & Logo 1707 and former Global Head of Marketing at TikTok, and Ricky Engelberg, Partner & Head of Sports at Maximum Effort. Together, they explored how bold ideas take shape and what it really takes to move them through complex organizations.
These calls offer a rare, off-the-record space where senior marketing leaders can hear real stories behind the moments, lessons and skills that have shaped how they lead. Read on for the highlights:
Ricky has seen firsthand that even the most innovative organizations stall without a clear direction. “The best companies often have very clear moonshots, shared north stars and also really embrace ambiguity.”
Nick’s learning emerged from intentionally choosing roles where the stakes were high and the path forward wasn’t obvious. As he describes it, “My story has been landing in places that are in the midst of a crisis.”
Those environments taught him that bold ideas usually fail not from overambition, but from organizational hesitation in the face of uncertainty. “A moonshot is essentially a calculated risk to make a huge leap… and the odds of it panning out are slim to none, but when it hits, it hits in a big way. And the learnings along the way are incredibly beneficial.”
What both leaders have learned is that it’s one thing to have a bold idea, but real leadership means clearing the way for real ideas to take flight.
Build coalitions that move faster than hierarchy.
Ricky learned early at Nike that big ideas don’t move because they’re approved — they move because people believe in them. As he put it, “All I have to do is go and find the seven people at the company who like the idea, and put together a coalition of the willing.”
And what began as a scrappy group of enthusiasts in the early 2000's became the catalyst for Nike shoes appearing in NBA video games. The coalition didn’t wait for a lane to be cleared, they simply created one.
Push teams to move faster than the system expects.
Both leaders see speed as non-negotiable. Ricky views decisive pace as a competitive advantage: “The ability for companies to say yes or no fast is a superpower.”
At Maximum Effort, this pace drives everything — especially culturally responsive work.
“The Peloton response ad… only worked by releasing it 24 hours later. Waiting three weeks, the moment is over at that point.”
Nick shares the same instinct, but from a cultural-timing perspective. He rejects the legacy marketing cycle outright: “I don't believe that a two-month campaign is the current playbook… as an example, we developed a process to implement campaigns in 72 hours and dubbed the initiative Project Cheetah.”
What drives that urgency is his recognition that timing directly shapes the level of impact: “By the time it goes out, they'll be over a month behind the relevance of that moment.”
For both leaders, clearing the path means shortening loops, removing bottlenecks, and creating an environment where action beats hesitation — because momentum, not polish, is what keeps ideas alive.
Redefine our relationship with failure — and help our teams do the same.
Clearing the path requires removing not just procedural barriers, but emotional ones. Ricky is clear-eyed about the cost of ambition: “All caps FAILURE SUCKS.”
But he also challenges leaders to interrogate their own hesitation: “Ask yourself the question of why do you think it's not gonna work—because it didn't work for you before, or because you don't think it works now?”
Nick reframes failure as proof of effort, not a mark against credibility. “I don't mind trying something so out of this world that it fails spectacularly… it's actually just a really good case study and a great lesson anyway. And those learnings yield other paths to success.”
When failure becomes insight rather than danger, teams stop tiptoeing and start moving.
Clearing the path is what transforms ambition into action. It’s what converts moonshots into traction, and traction into momentum. Ricky and Nick show that organizations move faster when:
As Ricky put it, the choice is always on the table: “In the end, you have a choice. Do you want to do normal things or radical things?”
And Nick captures what clearing the path ultimately protects: “Some of my biggest ideas… were done early in my career when I had nothing to lose. And I try to keep that spirit even now.”
Great leaders make sure their teams never lose that freedom.
Ricky Engelberg is Partner & Head of Sports at Maximum Effort, overseeing brand, content, and commercial strategy across their sports portfolio including Wrexham AFC and the BONDS Flying Roos, and investments in HOMAGE. He previously served as CMO & Head of Product at Vistaprint and spent nearly 20 years leading digital and brand innovation at Nike and Converse and has served as a LEAP Essentials 2025 mentor.
Nick Tran is President of CÎROC & Logo 1707 and former Global Head of Marketing at TikTok. He has also held leadership roles at Samsung, Hulu, Taco Bell, and Farfetch, and is an active angel investor with more than 75 investments including Liquid Death. Nick has also served as a LEAP Essentials 2025 Professor and Mentor.