In a recent episode of Anthony Scaramucci’s podcast, Shark Tank investor Kevin O’Leary drew an intriguing parallel between two of the biggest names in technology: Steve Jobs and Elon Musk. Released on May 5, 2025, this conversation provided an insightful look into O’Leary’s experiences with these influential leaders.
Reflecting on his time working with Jobs, O’Leary did not hold back. He characterized the late co-founder of Apple as:
“About 80% signal, 10% noise… not easy to work with, very unpopular, really nasty guy, but he really got it,” he shared.
While acknowledging the challenges of collaborating with Jobs, O’Leary expressed deep respect for his visionary outlook. However, O’Leary’s description of Musk was notably different. He noted that his own son is currently employed at Tesla, which perhaps added a personal dimension to his praise.
“He wastes zero time in his day. He has zero time to waste. There’s never been a man like him,” O’Leary remarked.
The discussion traversed various topics, including artificial intelligence, cryptocurrency, and leadership styles. Nevertheless, O’Leary’s comparative analysis of Jobs and Musk emerged as a focal point, highlighting the contrasting impacts these iconic figures have had on him as an investor.
Reflections on Steve Jobs: The Tough Reality of Leadership
Listen to the full interview here
O’Leary’s reflections on working with Steve Jobs left an enduring mark. In the Open Book interview, he shared candid insights into Jobs’ formidable work ethic. Describing Jobs’ approach, O’Leary noted that while Jobs had a sharp focus on achieving results, his domineering nature often made collaboration difficult.
“He was not a nice guy,” O’Leary recalled, reiterating many of the well-documented challenges faced by those in Jobs’ orbit. He pointed out that Jobs was “really nasty” and “very unpopular” among coworkers. However, O’Leary acknowledged that Jobs’ high expectations often spurred people to excel.
In previous remarks, O’Leary has echoed similar sentiments. In a Facebook post, he stated:
“What was it like working for Steve Jobs? It was BRUTAL! He was NOT a nice guy,” he declared.
O’Leary elaborated on Jobs’ management style, recalling instances where Jobs would “walk into a room and absolutely berate everybody in there.”Despite such harsh tactics, O’Leary recognized that this “brutal but effective”approach led to significant achievements.
The stark reality of Jobs’ personality has also been reflected in public accounts, including insights from his daughter, Lisa Brennan-Jobs, in her memoir Small Fry. O’Leary’s experiences with Jobs enhanced his perspective on leadership in the tech sector today.
Elon Musk: A Study in Productivity and Leadership
When discussing Elon Musk, O’Leary’s tone shifted to one of admiration. He praised Musk for his unwavering commitment to maximizing efficiency, emphasizing that Musk “wastes zero time.” O’Leary described conversations with Musk as remarkably focused and purposeful.
“He’ll walk away from a conversation with you if he’s wasting time. There’s never been a man like him,” O’Leary stated.
O’Leary highlighted that Musk’s relentless dedication to his ventures, including Tesla and SpaceX, is integral to his success. He mentioned that his son Trevor frequently shares positive feedback about Musk’s leadership style, aligning with O’Leary’s impressions of Musk as quick-thinking and driven.
In his dialogue with Scaramucci, O’Leary also touched on AI pioneers like Sam Altman but quickly returned to Musk, emphasizing how the latter’s unparalleled ability to bypass distractions allows him to achieve remarkable outcomes. “Elon has no noise. He’s 100% signal,” O’Leary noted, illustrating Musk’s knack for maximizing productivity by eschewing trivial discussions.
For more insights and discussions, catch the latest episodes of Shark Tank, now available for streaming on ABC.