By: Natalie Johnson
Courage Takes Flight is more than the title of AJ Thomas’s award-winning book. It also embodies a theme that runs through her life and work. From her early days as an undocumented immigrant to leading at Google X, to founding The Troublemaker Lab and Good Trouble Ventures, AJ has built a career centered around resilience, imagination, and leadership.
In this conversation, AJ reflects on her journey, her philosophy, and what it means to lead in uncertain times.
Q: Your career has spanned music, technology, venture capital, and coaching. Looking back, what connects all of these chapters?
AJ Thomas: At first glance, those paths might seem quite different. But the common thread across them all is creativity. Whether I was making music, designing human experiences at Google X, or building The Troublemaker Lab, the constant has been helping people imagine something bigger and then making it a reality. Creativity is not just an artistic skill; it’s a leadership skill.
Q: You often talk about scaling without losing your soul. What does that mean in practice?
AJ Thomas: In the startup world, scale often seems like the ultimate goal. But growth without intention can lead to burnout, create poor cultures, and undermine companies. Scaling without losing your soul means remembering that success isn’t solely about numbers; it’s also about staying true to your values as you grow. At The Troublemaker Lab, I work with founders to help them build companies that remain sustainable, human, and resilient.
Q: Where did that philosophy come from?
AJ Thomas: My own journey showed me that resilience and imagination are essential. I lived in my car when I first moved to the Bay Area. I was undocumented for part of my life. Those experiences could have broken me, but instead, they demonstrated that you can still build a meaningful life and career, even when the odds seem stacked against you. That’s why I created The Troublemaker Lab and later Good Trouble Ventures—I wanted to give underestimated leaders the support and platform I wish I had.
Q: How do you decide which founders to back at Good Trouble Ventures?
AJ Thomas: I look for vision and courage. Of course, numbers matter, but what I’m most interested in is the culture the founder is creating. Are they building something that connects people? Are they considering equity and impact? Are they willing to lead in ways that challenge the norms? These are the types of leaders who can shift industries, not just companies. At Good Trouble Ventures, we call it making “good trouble” because it’s about questioning old rules to make space for better ones.
Q: You were once Global Head of Talent and Human Experience Design at Google X, the Moonshot Factory. How did that experience shape your current work?
AJ Thomas: Google X taught me that even the boldest technologies need a strong culture to thrive. You can have the best engineers and the most ambitious ideas, but without trust and imagination, moonshots won’t succeed. That lesson carries over everywhere. Whether I’m coaching a founder or investing in a startup, I pay close attention to how they are shaping their culture. Because culture is not just a support system—it’s a strategy for innovation.
Q: You titled your book Courage Takes Flight. Why courage?
AJ Thomas: Courage is the foundation of everything. It’s what helps us move forward, even when the path ahead is uncertain. I’m also a licensed pilot, and flying taught me that leadership is a lot like aviation. You need to trust your instruments, stay calm in turbulence, and know when to adjust your course. But above all, you need the courage to take off in the first place. That’s true for flying, and it’s true for leadership.
Q: What challenges do you see leaders facing most often today?
AJ Thomas: Many leaders are caught between the pressure to scale quickly and the need to protect their teams and culture. Add in AI, economic uncertainty, and global complexities, and it’s easy to feel overwhelmed. The challenge is not just about growing quickly—it’s about growing thoughtfully. Leaders need the courage to slow down where it matters, ask the tougher questions, and hold onto the values that make them unique.
Q: What advice would you give to founders or executives who feel like they are at a breaking point?
AJ Thomas: First, remember that you’re not alone. Community isn’t just emotional support; it’s also a strategic asset. Lean on peers, mentors, and allies. Second, define what success truly means for you—not just what investors or headlines tell you it should be. Finally, give yourself permission to imagine a future that’s bigger and bolder than your current reality. That imagination is fuel.
Q: Looking ahead, what excites you most?
AJ Thomas: I’m excited about expanding The Troublemaker Lab into a leading accelerator for founders who want to build companies that matter. I’m also focused on growing Good Trouble Ventures to back creatives and technologists reshaping entertainment, media, and human connection. More than anything, I’m energized by the next generation of leaders proving that you can scale with soul, lead with courage, and transform culture in the process.
Closing Thought
Courage Takes Flight is more than just a book title or philosophy. It’s an invitation—to founders, leaders, and anyone who wants to make a real impact. As AJ Thomas’s journey demonstrates, the most extraordinary outcomes don’t come from following the old rules. They come from the courage to write new ones.
