Thriving in chaos: top leaders’ strategies from Masters of Scale Summit

Host Bob Safian frames the live session around his “Generation Flux” idea, first developed when he was editor of Fast Company: thriving now requires operating amid constant, accelerating change. He says the discussion will cover skill building, organizational leadership, unplugging, speed versus haste, and prioritization. The guests include chaos theorist and former U.S. Chief Data Scientist DJ Patil, Google X advisor Raina Kumra, Upwork CEO Hayden Brown, media host Baratunde Thurston, Watch Duty CEO John Mills, and Autodesk CMO Dara Treseder with her husband, Arkenstone co-founder William Treseder.

Patil demonstrates the double pendulum he says came from Jim York’s lab; York coined the term “chaos theory.” Although the device is mathematically predictable from two variables describing the pendulums’ positions, tiny changes can eventually produce radically different movements—the “butterfly effect.” Patil compares this with weather forecasting: sometimes forecasts remain accurate two or four weeks out, but in other conditions the useful forecast horizon shrinks to mere hours. For business leaders, the practical question is not simply whether a system is chaotic, but how much forecast range remains and what action is still possible.

Kumra says her career had given her a complete but exhausting “toolkit,” and she no longer wanted to carry the backpack of learning everything herself. She now operates like the CEO of a team of 12 AI agents, including virtual CEOs, CMOs, COOs, and engineers. Some agents outperform her in math while others have “the judgment of a toddler,” so she keeps judgment and clarity close rather than outsourcing them. Her advice to people afraid of falling behind is: “There is no keeping up. There is only keeping calm.” People can outsource some learning, but remain responsible for preventing AI-generated “crap” from reaching the world.

Upwork CEO Brown says teams are grateful to be operating in a remarkable era but still ask, “Now what do we do?” Her answer is to abandon the roadmap that assumes an exact route and instead head toward a changing horizon, learning and iterating daily while reassessing what lies ahead. Upwork has deliberately returned to its startup roots, restoring agility and flexibility after becoming a public company focused on predictability and low risk. Its internal “Crystal Ball” tool uses governed company data to give employees accurate insights in hours rather than requiring analysts weeks, democratizing access to business intelligence.

Thurston leads the audience through a breath and says speed can turn the same physical motion from a gentle touch into a violent attack. He is trying not to become a machine pursuing a pace set by others, though he rejects completely opting out because he enjoys technology and grew up with a coder mother. His test for technology is whether it helps or hinders his relationship with himself, other people, and the rest of life. If tools replace self-knowledge, eye contact, community, or attention to nature, he says he must “remember himself” by looking up, breathing, and reconnecting.

Watch Duty CEO Mills says “move fast and break things” is dangerous in wildfire and flood intelligence, where precision matters more than being fastest. He compares the goal to choosing a precise surgeon rather than boasting about the fastest one: Watch Duty delivers information within minutes, but shaving that to seconds is irrelevant if accuracy suffers. Mills uses AI to process signals and reduce fatigue, but insists humans must interpret the results, like a pilot supervising autopilot. Broadcasting unfiltered signals can mistake training exercises for real fires and, in his words, get people killed.

After hearing the other speakers, Patil says mathematics contains “islands of calm in chaos,” moments when people can regain control despite continual disruption. He connects this to lessons from President Obama and former Defense Secretary Ash Carter: leaders must fight cynicism every day, find calm, and still take action. The double pendulum becomes a reminder that chaotic systems can be observed and used rather than merely feared. Patil’s point is not that uncertainty disappears, but that people can identify workable moments and tools inside it.

Dara Treseder of Autodesk and William Treseder of Arkenstone Defense say they cannot keep every part of life perfectly balanced. They classify marriage, their children’s well-being, health, and family financial stability as glass balls that must not break; sleepovers with friends and other valued activities are rubber balls that may be dropped intentionally or by circumstance. They communicate about whether a rubber ball is becoming a glass ball, and whoever leads a priority asks the other, “What do you need from me?” They also share a journal without critiquing entries, using it to discuss difficult feelings after the fact.

The Treseders bring business language home through a family whiteboard, goals for their children, and a family NPS: one score for the marriage and one for whether their children feel safe, loved, and able to call their parents first. William says Dara has never broken a promise to their children, including attending an event after an international flight. Their hierarchy places faith, family, and then service or vocation, and William is discussing reenlisting in the Marines for four more years with both his wife and children. Dara adds that attention is not automatically deserving of energy; energy should go to what matters over meaningful time and aligns with character.