A.J. Thomas, the CEO of Troublemaker Lab and Founder and General Partner of Good Trouble Ventures, where she helps extraordinary founders build enduring companies through coaching, strategy, and mindful innovation. She ran global talent and human experience design groups at X—the "moonshot factory" known as Google X—and served as CXO-in-residence at A.Team.
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1. Making "Good Trouble": Leading with the Heart in a High-Tech World
A.J. explains her dual approach to supporting entrepreneurs through her two main projects:
Troublemaker Lab: Unlike traditional accelerators that only focus on business metrics, this lab focuses on the leader’s personal ecosystem. It balances three core pillars: Self, Health, and Wealth.
Good Trouble Ventures: An all-female venture fund that invests in the sweet spot where technology, creativity, and culture meet.
While many business leaders follow Simon Sinek’s famous "Start with Why" philosophy, A.J. suggests we need to go deeper. She introduces the concept of the "Who." Before you can understand why you are doing something, you must understand who you are.
She argues that in the fast-paced world of investing, self-awareness is often used as a tool for manipulation or productivity. Instead, she advocates for using it to build genuine curiosity and better human connections.
Drawing from her work at UC Berkeley, A.J. shares four simple but powerful principles for showing up as a better leader and person:
Show up and be present: Don't just be in the room; be intentional about why you are there.
Listen for heart and meaning: Pay attention to the "leaks"—the words or themes a person repeats—to understand what they truly care about.
Tell the truth without judgment: Create a safe space where you can be honest about challenges without pointing fingers.
Be open to the outcome, not attached to it: Avoid "tunnel vision." When you aren't obsessed with one specific result, you become more creative and see possibilities you might have otherwise missed.
Where you would typically think of a startup accelerator or a business accelerator, we focus really on the human in the middle of that entire ecosystem they're trying to create. (A.J. Thomas)
2. The Final Frontier: Why the Best Leaders Explore Inward
While we often think of exploration as traveling to new places or launching into space, A.J. argues that the "last frontier" is the human self. * Fulfillment vs. Achievement: Leaders who hit their targets but feel empty often focus only on external wins. Truly fulfilled leaders are those who "explore inward," connecting their heart and feelings to their work.
The Power of Presence: When a leader is grounded in who they are, you can feel it. This "embodied" leadership leads to clearer communication and a stronger company vision.
The conversation shifts to a provocative idea: Money and power don't change who you are; they reveal who you are. A.J. notes that many founders struggle when they suddenly receive massive funding because they haven't done the "internal work" first. At her Lab, she helps leaders bridge the gap between their public persona and their private self. They reframe wealth to be about more than just a bank account—it’s about having control over your time, your health, and the quality of your relationships.
Alex shares a vulnerable insight that many professionals can relate to: the patterns that cause trouble at work are often the same ones causing friction at home.
Patterns of Behavior: We often use "work behaviors" (like pitching or trying to influence) in our personal lives, only to find they don't work with our partners or children.
The "Vulnerability" Trap: They critique the common business school advice to "be vulnerable to influence others." If you are only being vulnerable to get what you want, you’re missing the point. True vulnerability isn't a tactic for manipulation; it's a path to genuine connection.
If you haven't done that internal work before getting there, we find a conflict between how someone wants to show up externally versus how they think about themselves personally. (A.J. Thomas)
3. Beyond the "Success Mask": Creating Portals and Finding Presence
A.J. clears up a major misconception: vulnerability doesn't mean sharing your deepest secrets or childhood traumas with everyone you meet. Instead, she defines it as being open in the present moment.
The "Astronaut" Perspective: Drawing from her work with NASA candidates, she explains that vulnerability is simply the act of holding space for someone else and saying, "I see you."
Letting Go of Control: Alex adds that vulnerability often looks like accepting imperfection—whether in a business result or a child’s behavior—without immediately trying to "fix" or control it.
A.J. shares her own remarkable journey, revealing that despite her high-level success at places like Google X, she once lived in her car while attending grad school as an undocumented immigrant.
Creating New Doors: Rather than just opening doors that already exist, A.J. sees her mission as "creating portals"—building opportunities for people (like first-generation immigrants or women in tech) who were never supposed to be in those rooms in the first place.
The Abundance Mindset: She reflects on how starting from a place of "lack" eventually led her to a mindset of abundance. She doesn't have a "chip on her shoulder" about her past; instead, she uses it as fuel to help the next generation.
How does a high-powered CEO and venture capitalist stay grounded? A.J. credits her three children. She views them as her biggest teachers because they require her to use the same "curiosity" she brings to her business strategy.
The Micro-Moments: Whether it's a board meeting or a crying toddler, the question remains the same: "I’m curious—what is happening here?"
Hindsight and Growth: A.J. notes that many people spend their lives performing to reach the top, only to find that worldly success feels empty. The antidote is staying grounded in your personal "why" and realizing that you don't have to "do it all" alone.
It’s easy to open doors that are already there. But are there doors we can create where there never was a portal? (A.J. Thomas)
4. The "Monkey Bar" Mindset: Why the Best Leaders Never Grow Up
The conversation starts with a powerful reversal of roles: parents don't just raise kids; kids raise their parents. A.J. argues that the "battle cry" of a great leader should be the courage to be curious—the same unbridled, honest curiosity we see in children.
The Monkey Bar Theory: Jumping from one market or industry to another is just like jumping between monkey bars on a playground. It requires a lack of "blocks" and a willingness to try.
The "Secret" of the Boardroom: Alex and A.J. joke that behind every serious executive is a "12-year-old" self. The key to staying grounded is to not take yourself too seriously—or, as A.J. puts it, "Rule number one: Don’t take yourself so seriously. Rule number two: See rule number one.
A.J. shares two brilliant acronyms she learned from her own children that have become her guiding principles in business:
FAIL (First Attempt In Learning): If you view failure as a first attempt, you stop fearing it. (Though she notes that doing the exact same thing twice is a mistake that needs a "corrective action"!)
UGLY (U Gotta Love Yourself): To have the courage to fail in public, you have to have a foundation of self-love.
As a venture capitalist, A.J. faces a tough reality: she has to say "no" to hundreds of people. However, she balances the "venture mind" with the "human mind" by sticking to a unique investment thesis at Good Trouble Ventures.
Putting Artists First: Most investors look at technology first. A.J. looks at the creator (the artist, athlete, or musician) and builds the technology around them. She focuses on "picks and shovels"—the tools and infrastructure that allow creative people to actually make a living.
The "I Don't Know" Test: When evaluating a founder, she doesn't just look at the product; she looks at their character. "If a founder says, 'We don't have competitors,' it makes me bristle. I’d much rather have a founder say, 'That’s a great question, I don’t know, let me get back to you.'"
If a founder says, 'We don't have competitors,' it makes me bristle. I’d much rather have a founder say, 'That’s a great question, I don’t know, let me get back to you.' (A.J. Thomas)
5. The "Humbitious" Leader: Innovation Through Constraints and Curiosity
Having worked at Google’s famous "Moonshot Factory" (X), A.J. reveals a surprising truth: innovation doesn't happen because you have an endless budget. It happens because of constraints.
Revel in Constraints: A.J. argues that true innovation occurs when you have "both hands tied behind your back." When resources are tight, you are forced to be more resourceful.
Kill Criteria: At Google X, they didn't just look for reasons to keep projects alive; they looked for reasons to "kill" them. If the signals (the underlying human or scientific factors) were off, they ended the project—even if the metrics looked good.
Metrics vs. Signals: Metrics tell you how much money you might make, but signals tell you if the foundation is actually strong enough to survive long-term.
A.J. observes a major shift in the world of AI and technology. In the beginning, founders built "point solutions"—tools that did one specific thing, like recording a meeting or managing a calendar.
Now, the "enlightened" founders are systems thinkers. They aren't just looking at one pain point; they are looking at the entire ecosystem. They ask how their product fits into the user's whole life and purpose, rather than just being a temporary fix that a larger company (like Google or Adobe) will eventually build into their own platforms.
Alex and A.J. redefine what it means to be a "creator" in the age of AI. It isn't just for artists or YouTubers; it’s for anyone who takes a proactive step to move an idea forward.
The Definition of "Humbitious": A.J.’s favorite founders are "humbitious"—a mix of humble enough to admit they don't have all the answers and ambitious enough to think 20 years ahead.
The "Boring" Industries: Even if you work in a highly regulated field like compliance or insurance, you are a creator if you are helping people make better decisions or see around corners.
The Goal: To move from a "pain point" (a small problem) to a "purpose" (a meaningful impact).
Innovation doesn't happen when you’re comfortable; it happens when you revel in your constraints—when you have both hands tied behind your back. (A.J. Thomas)
Check the episode's Transcript (AI-generated) HERE.