The Troublemaker Mindset: Building Culture and Value for High-Impact Business Exits

Aaron and A.J. dive into the transformative concept of "making good trouble" in business: challenging the status quo, fostering innovative thinking, and balancing ambition with humility. From the importance of self-care as a founder to building resilient operating systems and cultures that can thrive independently of their founder.

Author

Aaron Alpeter
October 29, 2025

This week’s episode features an energizing conversation between Aaron Alpeter and A.J. Thomas, founder/GP at Good Trouble Ventures and former Google X operator, on how to spark “good trouble” that drives REAL enterprise value.

Here’s what you’ll take away from this episode:

1. Good Trouble Isn’t Just Noise—It’s Innovation with Humility A.J. took us back to the roots of “good trouble” (thanks, John Lewis!) and translated it into the business context: challenging the status quo, asking courageous questions, and—most importantly—doing so with the humility to admit when you’re wrong and learn faster. That’s the seed of innovation.

2. Founder Mode: Great for the Grind, Terrible for Longevity You know the grind—founders are celebrated for their headstrong drive, but A.J. cautions that burning the candle at both ends leads nowhere fast. She advocates treating yourself like an athlete: recognize when your “business optimism” is actually just sleep deprivation and stress, then pause and reset. True sustainability = caring for founder self, health, and wealth.

3. Architecting Culture: The Tech Stack Approach for Humans A.J. broke down her “mission acceleration” philosophy: treat your org like a tech stack!

  • The Operating System (Mission, Vision, Values)

  • The Application Layer (Individuals, Teams, Systems)

  • The Features (Goals, KPIs) Problems at the feature level (“we missed a goal”) often stem from deeper misalignments in your OS. Diagnose before you debug!

4. Google X’s Moonshot Mentality = Kill Criteria + Sharing Learnings A.J. gave us a peek inside Google X, where the goal isn’t incremental improvement but 10x leaps. Teams are rewarded for shutting down projects that don’t meet strict signal-based “kill criteria”—and learnings are shared, compost-style, for others to build on. You don’t need a Google R&D budget: apply the same “R&D mindset” to your own experimentation, partnerships, and humility.

5. Building a Business Worth Buying Today A.J.’s parting advice? Articulate the right questions, leverage data and AI for market signals, and audit not just financials but the culture and leadership behind a company. Sustainable businesses WORTH buying are built when leaders innovate with both courage and humility, and when culture is ready to scale beyond the founder.

Your Next Steps:

  • Diagnose YOUR company’s core—are you debugging at the feature level or is it an OS issue?

  • Institute a “good trouble” culture: reward curiosity, not just headstrong decisions.

  • If you’re thinking about selling, start building processes and systems that can outlast you—the founder.

How to Scale Supply Chain Wargames for Small, Mid-Size, and Global Brands

Supply chain stress tests aren’t just for Fortune 500s. Whether you’re running a $50M brand or coordinating global operations, scenario workshops—what we call wargames—reveal the blind spots that SOPs can’t.

But one-size-fits-all doesn’t work. The right workshop depends on your size, risk profile, and decision complexity.

Most brands are rethinking their sourcing. Are you?

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