The 4:30 a.m. CEO: How discipline and sacrifice built a $16B empire

Khozema Shipchandler, the chief executive officer of Twilio Inc. , maintains an intense and highly structured daily routine that reflects his long-standing belief in the value of sacrifice and discipline in leadership. According to a Fortune interview, Shipchandler begins his day at 4:30 a.m., scanning emails, Slack messages, and texts for any urgent issues that require immediate attention [1]. He follows this with a morning workout, breakfast—often a smoothie—and a review of news headlines [1]. By 7:30 a.m., he is officially at work, well ahead of most of Twilio’s engineering team, which typically begins their day at 9 a.m. [1].

Shipchandler, 51, has maintained this routine for decades, crediting his immigrant background and early drive as key to his rapid career progression. His parents, who moved from Mumbai to the United States, instilled in him a strong work ethic and the idea that hard work and play must coexist. By the age of 31, he had already become the CFO of a multi-billion-dollar GE business [1]. His current position as CEO of Twilio , a $16 billion company with more than 5,500 employees, is the result of what he describes as consistent work-life choices that prioritize long hours and personal sacrifice [1].

While many in Gen Z and millennial generations increasingly value flexibility and work-life balance, Shipchandler is skeptical of the feasibility of achieving high-level leadership without a similar commitment to time and effort. “Every one of us has to make certain work-life choices,” he stated, acknowledging the trade-offs involved, such as missing important events in his son’s life [1]. He added that he has never met a peer who is in the C-suite without a comparable routine [1].

Despite his rigorous schedule, Shipchandler emphasizes working smarter rather than simply longer. He is selective with his meetings, often limiting them to 25 or 50 minutes within a 30- or 60-minute block, respectively, and uses the intervening time for brief physical activity, such as running laps around his house or walking on a treadmill [1]. These habits, he says, help him stay energized and focused while minimizing distractions [1]. He also avoids social media, which he believes is a major time sink for many professionals.

On weekends, Shipchandler’s routine is slightly less intense, though he still works most Sundays. He reserves six to eight hours on Saturdays as a break from work, a rare reprieve from the demands of his role [1]. His day ends at 9:30 p.m., after a final hour of work and a brief unwind—either watching SportsCenter during travel or whatever “his wife falls asleep to fastest” when at home [1].

Shipchandler’s approach to leadership and personal productivity highlights a stark contrast to evolving workplace norms. As the younger workforce increasingly values autonomy and flexibility, Shipchandler remains a staunch advocate for long hours and strategic habit-building. His disciplined approach has been instrumental in his career success, and he continues to apply it at the helm of one of the world’s most valuable communication technology companies.

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