From the Streets to Apple: How Curiosity, Trust, and One Idea Built a $40M Deal | Jay Strommen
Mon Feb 02 2026
How do you go from survival mode at 15… to building a company that supports global product launches in 52 countries?
In this powerful conversation, Charles Eide interviews Jay Strommen, the “man behind the curtain” who helped Apple scale its iconic retail experiences—starting with one table, one bold yes, and one life-altering moment: Steve Jobs walked up, inspected the build, and said, “It’s good.”
But this episode isn’t just about brand-name wins. Jay opens up about the childhood trauma that fueled his drive, the internal “not good enough” story that followed him even through massive success, and the personal transformation that changed how he leads today.
You’ll hear what he learned from building relationships with leaders at brands like Disney, Nike, and Nordstrom—and why the best leaders don’t lead with numbers… They lead with intention.
In this episode you'll learn:
Curiosity is a leadership superpower. Jay’s “be curious” philosophy becomes the bridge to trust, influence, and better decision-making.
Empathy isn’t fixing—it's sitting with someone. He explains compassion as the ability to make people feel seen without trying to solve them.
Relationships beat transactions. Jay built long-term trust before he “had anything to sell”—and that trust became his unfair advantage.
The real flex is reliability. “We say yes when others say no” only works if your team consistently delivers under pressure.
Success won’t heal self-worth. Even at the peak—big revenue, big projects—Jay realized achievement doesn’t automatically create peace.
Belonging scales performance. The strongest cultures “don’t make it personal”—they rally around solving the problem together.
Lead with intention, not numbers. Numbers matter, but when you start with a number, people become transactional. Start with values and support, and the number follows.
About Jay Strommen:
Jay Strommen is a business builder and relationship-driven leader known for helping iconic brands bring retail experiences to life at massive scale. He played a key role in transforming PD In-store from a legacy printing company into a global execution partner supporting high-stakes product launches, complex deployments, and “impossible” timelines—earning trust with teams inside Apple and beyond.
Jay’s story is defined by contrast: early hardship and survival, followed by building a high-growth company—while learning that external success doesn’t automatically create internal peace. Today, he speaks openly about leadership, intention, curiosity, and the responsibility leaders have to create a true sense of belonging for the people they serve.
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How do you go from survival mode at 15… to building a company that supports global product launches in 52 countries? In this powerful conversation, Charles Eide interviews Jay Strommen, the “man behind the curtain” who helped Apple scale its iconic retail experiences—starting with one table, one bold yes, and one life-altering moment: Steve Jobs walked up, inspected the build, and said, “It’s good.” But this episode isn’t just about brand-name wins. Jay opens up about the childhood trauma that fueled his drive, the internal “not good enough” story that followed him even through massive success, and the personal transformation that changed how he leads today. You’ll hear what he learned from building relationships with leaders at brands like Disney, Nike, and Nordstrom—and why the best leaders don’t lead with numbers… They lead with intention. In this episode you'll learn: Curiosity is a leadership superpower. Jay’s “be curious” philosophy becomes the bridge to trust, influence, and better decision-making. Empathy isn’t fixing—it's sitting with someone. He explains compassion as the ability to make people feel seen without trying to solve them. Relationships beat transactions. Jay built long-term trust before he “had anything to sell”—and that trust became his unfair advantage. The real flex is reliability. “We say yes when others say no” only works if your team consistently delivers under pressure. Success won’t heal self-worth. Even at the peak—big revenue, big projects—Jay realized achievement doesn’t automatically create peace. Belonging scales performance. The strongest cultures “don’t make it personal”—they rally around solving the problem together. Lead with intention, not numbers. Numbers matter, but when you start with a number, people become transactional. Start with values and support, and the number follows. About Jay Strommen: Jay Strommen is a business builder and relationship-driven leader known for helping iconic brands bring retail experiences to life at massive scale. He played a key role in transforming PD In-store from a legacy printing company into a global execution partner supporting high-stakes product launches, complex deployments, and “impossible” timelines—earning trust with teams inside Apple and beyond. Jay’s story is defined by contrast: early hardship and survival, followed by building a high-growth company—while learning that external success doesn’t automatically create internal peace. Today, he speaks openly about leadership, intention, curiosity, and the responsibility leaders have to create a true sense of belonging for the people they serve.