Some leaders are specialists, climbing one ladder their entire lives. Others move across industries, reinventing themselves at every turn. AJ Thomas belongs to the second group, a rare kind of leader who thrives at intersections, weaving together creativity, technology, and culture into something new.
Today, she is the Founder and CEO of The Troublemaker Lab, a leadership accelerator for bold founders, and the General Partner of Good Trouble Ventures, an early-stage fund investing in companies that shape culture as much as markets. Her resume includes leading human experience design at Google X, advising through A.Team, and authoring award-winning books on leadership.
What makes AJ stand out is not just her achievements, but her ability to reimagine what leadership looks like for every era she steps into.
A Nonlinear Path
AJ’s career began in music. Creativity was her first language, and performance taught her lessons about storytelling and audience connection that she carries into business today.
From there, she transitioned into leadership roles in high-growth companies. At Auction.com, she learned what it meant to scale at speed. At Google X, she helped design the culture behind moonshot projects, reminding innovators that the boldest technologies only succeed if the teams behind them trust each other enough to take risks.
Each chapter may look unrelated, but together they form a clear pattern. AJ thrives at the edges where creativity and systems collide, where innovation needs culture, and where leaders need courage.
The Troublemaker Lab
With The Troublemaker Lab, AJ distilled these experiences into a platform for others. The accelerator helps founders and executives grow differently, not just faster. Its mission is simple but radical: help leaders scale without losing their soul.
For AJ, this means more than coaching. It means creating a space where bold ideas are nurtured without burning out the people behind them. It means building companies that value creativity, community, and courage as much as capital. It also means reminding leaders that success defined only by speed and profit is fragile. Success defined by purpose is sustainable.
Good Trouble Ventures
Good Trouble Ventures is the investment arm of AJ’s philosophy. Inspired by John Lewis’s call to make “good trouble,” the fund backs founders who challenge outdated systems and offer new cultural narratives.
Instead of only asking about TAM or exit strategy, AJ asks: What culture are you shaping? How will your company change the way people live, connect, and imagine the future?
The result is a portfolio that blends financial potential with cultural impact. From media platforms to AI tools to community-driven startups, Good Trouble Ventures focuses on founders who see business as a force for both profit and progress.
Leadership for the Future
AJ’s career also includes writing for Forbes and speaking on global stages, where she challenges leaders to rethink their playbooks. Her perspective on the future of work is clear: efficiency is not enough. In the AI era, leaders must prioritize imagination, humanity, and courage.
She often describes leadership as less about controlling outcomes and more about creating conditions where others can thrive. In practice, that means building ecosystems instead of silos, encouraging collaboration across disciplines, and reminding teams that culture is not just “soft stuff.” It is infrastructure.
Courage as a Constant
Through all the reinventions in her career, one theme runs consistently: courage. AJ became a licensed pilot partly because she was fascinated by flight, but also because it mirrored leadership. Flying demands calm in turbulence, trust in your instruments, and the willingness to take off even when conditions are not perfect.
For AJ, that is what leadership requires too. The courage to move forward even without certainty. The courage to hold onto values when pressure builds. The courage to imagine a different future when the present feels fixed.
Looking Ahead
AJ Thomas is still building. She is expanding The Troublemaker Lab into a premier hub for braver leadership. She is scaling Good Trouble Ventures to back creatives and technologists shaping global culture. And she continues to use her platform as a writer and speaker to advocate for leadership that blends creativity, technology, and humanity.
Her story is not about one straight climb. It is about reinvention, resilience, and the power of working at intersections. In a world that often rewards narrow expertise, AJ proves there is another way, one where courage and creativity fuel a different kind of success.
