In a wide-ranging conversation, the speaker delves into his personal history, professional philosophy, and observations on the world, prompted by reflections on his book. He begins by noting that writing his family's history was an "unexpected gift," allowing him to understand "who I am and why I became whatever it is that I've become." He highlights the indelible "imprint" parents leave during formative years, shaping both "angels and demons" that stay with an individual for life.
His upbringing as a child of Jewish refugees from Nazi Germany in Wales instilled a "drive and grit." His parents, though never in camps, "survived" as refugees, leading to a profound need to be vigilant and suspicious of others' motives. This survival instinct, he notes, wasn't conveyed through stories – his parents rarely spoke of the past – but through their daily behavior and sense of impending doom. He contrasts his grandfathers: his paternal grandfather, a civil servant, believed in the state's endurance and delayed leaving Germany until it was too late, perishing in the Holocaust. His maternal grandfather, a "more streetwise" and entrepreneurial cattle trader, escaped 72 hours before war broke out. The lesson learned from this, he shares, is the necessity of having a "bolt hole," a place to go if things get too hot, metaphorically saying, "you can never have enough passports."
Reflecting on the current global state, he finds it an "uncomfortable place for minorities," citing insecurity among various groups in the US and Europe. While he accepts anti-Semitism as a constant, he warns of economic distress fueling authoritarian impulses. Despite this, he holds some optimism, noting historical pushes to the center and the potential for new technologies, though he acknowledges the internet's role in amplifying extremes.
Professionally, he explains his method of investigating a person's first 14 years, a technique refined after observing Lee Iacocca's outsider identity stemming from his childhood as the son of Italian immigrants. He views this "outsider energy" as a powerful driver but notes that its intensity may diminish over time, though the "inner being doesn't change." He collects "dots" from conversations to form a composite portrait of an individual, often asking what one thing they would do differently, a question that once moved an interviewee to tears over a childhood transgression. For himself, he wishes he had handled interactions with his parents differently, attributing early conflicts to a natural drive for independence, arrogance, and a lack of understanding of their experiences.
He recounts the story of Anna, a Roman Catholic nanny who, with her husband, bravely sheltered his grandparents and father in Nazi Germany, embodying "one of the righteous" who possessed an unyielding "ethical compass." This led him to ponder the "resistors, the silent, and the collabos" during the COVID pandemic, concluding that true resistors are very rare.
His career took a turn when Bill Deeds, editor of the Daily Telegraph, advised him to go to America, leading to his first big break at Time magazine. A "painful" episode with Steve Jobs resulted from a malicious Time profile, severing their relationship. He was not "in awe" of Jobs, respecting and admiring him while being aware of his "darker shades." He notes the role of "monomania" – complete obsession – in creating anything of value, citing Frank Auerbach, an artist who dedicated his life almost entirely to his craft. The primary cost of monomania, he believes, is typically relationships.
His entry into venture capital at Sequoia was unconventional, as he lacked a technical background. Don Valentine, Sequoia's founder, took a risk on him, believing in observation and a "survivalist instinct" over formal training. He reflects that today's venture business is far more complex than in his early days, with abundant information and numerous players making it harder for individuals to build close relationships. As he took over Sequoia, his main goal was "not to screw it up" and to ensure accountability to investors, particularly non-profits. He learned "tolerance" from his partnership with Doug and observed Alex Ferguson's skill in understanding and supporting individual players.
He firmly believes in the "great person theory" of history, citing Elon Musk as a contemporary exemplar whose achievements are "beyond comprehension." Regarding AI, he is "more hopeful than others," acknowledging potential disruption but believing it will create more jobs than it destroys, citing historical precedents where technological advancements ultimately led to overall employment growth.
He defines "extraordinary writing" as hearing the "unmistakable voice of the author," achieved by being in touch with one's inner feelings and voice. He resonates with Joseph Campbell's idea that "the privilege of a lifetime is becoming who you are," though he feels he hasn't fully achieved it, often being "too prone to... live up to the pressures or expectations from the outside." He attributes this to his mother, who "always felt that disaster was always around the corner" and found fault even in his successes. Stepping back from Sequoia allowed him to pursue diverse interests like writing, philanthropy, and launching the San Francisco Standard, a media business aiming to show local journalism can be profitable and provide a balanced voice.
In the final analysis, he believes two things matter: "relationships with the people that you care about" and "trying to leave things a little better... than they were." The kindest thing anyone has ever done for him, he concludes, is marrying him, and from his wife, he has learned "tolerance."