When Data Isn’t Enough: Leadership, Risk, and Resilience with Tim Delisle
By Susan Hunt
February 9, 2026
What Does It Mean to Truly “Stare Down the Bull” in Leadership?
On this episode of Stare Down the Bull, host Susan Hunt sits down with Tim Delisle, founder of 514 and former Head of Development at Nike, for an honest conversation about leadership, conviction, and building through uncertainty.
Tim’s career is marked by bold transitions—from founder to enterprise leader and back again—and by moments where clarity only came after taking the leap.
From Rejection to Resilience
Tim’s journey didn’t begin with confidence—it began with rejection.
Early in his career, he was told he wasn’t “technical enough” to enter an engineering program. Instead of accepting the decision, he pushed back, made his case, and earned a second chance. That moment shaped how he approaches business, leadership, and opportunity to this day.
It taught him that rejection is rarely final—and that persistence often matters more than credentials.
Founding, Selling, and Letting Go
Selling his first company to Nike was one of the most difficult decisions Tim has ever made—not because of the money, but because of what it represented. As a founder, the company was deeply personal.
The decision forced him to weigh:
- Financial outcomes against responsibility to employees
- Personal identity against future opportunity
Ultimately, reframing the choice as an investment in what came next helped him move forward with conviction.
Leadership Inside Complexity at Nike
Joining Nike meant stepping into one of the most complex, matrixed organizations in the world—and doing so at a very young age.
Tim learned quickly that success in large enterprises isn’t just about having the right ideas. It’s about understanding culture, earning alignment, and learning how to be effective inside existing systems.
One of his boldest initiatives ultimately failed, not because it lacked merit, but because the organization wasn’t ready for it. That experience became one of his most valuable leadership lessons.
Why Tim Founded 514
Tim founded 514 after repeatedly seeing the same issue inside large enterprises: data locked away in systems that don’t serve the people doing the real work.
Rather than focusing exclusively on centralized data teams, 514 is built around a different belief:
- Real business value is created inside end-user applications
- Software engineers need direct access to data to build those tools effectively
By leveraging AI and lightweight, developer-first data systems, 514 aims to activate data where it actually drives outcomes.
The Real “Stare Down the Bull” Moment
Tim’s most recent stare down the bull moment wasn’t external—it was internal.
As a CEO surrounded by exceptionally smart executives, he realized that constantly revisiting strategy was weakening execution. Data was being used to second-guess conviction rather than support it.
His key leadership insight:
- Data should inform conviction, not replace it
- Execution suffers when leaders constantly change direction
Learning when to stop debating and start committing became one of the hardest—and most important—leadership muscles he’s had to build.
Final Takeaway
This episode is a thoughtful exploration of modern leadership.
It’s about resilience, conviction, and learning when to trust your judgment—even in the presence of uncertainty and brilliant people with strong opinions.
For founders, executives, and leaders navigating complexity, Tim Delisle’s story offers a clear reminder:
You don’t grow by avoiding the bull. You grow by facing it—and moving forward anyway.
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