In this conversation, Guy reflects on working with Steve Jobs, the difference between mission-driven and ego-driven leadership, and why the best products are built by people solving problems for themselves. He shares hard-earned lessons from Silicon Valley on creativity, obsession, grit, and what it really takes to build things that last.

Before becoming one of the most respected surfboard shapers in the world, Bob Pearson built his craft through obsession, experimentation, and more than six decades of hands-on learning. Since shaping his first board in 1964, Bob has remained committed to one belief: mastery is never finished.

In this conversation, Tim reflects on backing category-defining companies, including Tesla, SpaceX, Skype, Hotmail, Twitch, and Robinhood, investments that went on to create hundreds of billions of dollars in enterprise value and permanently change global industries. He also shares the impact of Draper University, where thousands of founders have been trained, leading to thousands of companies launched and multiple billion-dollar outcomes.

In this episode of Divot, we sit down with Aparna Chennapragada, Chief Product Officer for AI at Microsoft, to explore how artificial intelligence is reshaping the way products are built, teams collaborate, and companies scale in an increasingly automated world.

In this episode, Josh breaks down the realities of building and leading a high-growth startup, navigating regulation, designing products for long-term impact, and maintaining culture as teams and responsibilities scale. He explains how focusing on customers, discipline, and long-term thinking has shaped Gusto’s journey and why sustainable growth matters more than chasing short-term wins.

In this conversation, Brandt shares the real stories behind I Was a Stranger, his new film inspired by the Syrian refugee crisis. He explains how meeting smugglers, soldiers, parents, and children across Syria, Turkey, Jordan, and Haiti reshaped his understanding of judgment, fear, and humanity.

In this conversation, David shares the mindset shift that saved his marriage, the four values that rebuilt his identity, and how losing over $100M became the foundation for a healthier, more purposeful life. He explains how faith, gratitude, sleep discipline, and time mastery helped him recover, along with the frameworks he teaches today to serve his mission of empowering over a billion people. From stop-drop-and-roll to emotional chemistry and using failure as fuel, David breaks down the tools that rebuilt his life from the inside out.

In this conversation, Squint breaks down the ingredients of a powerful photograph, motion, eyes, framing, intimacy, and explains why rejection became his greatest superpower. He shares how he wrote a list of dream subjects at age 12 and photographed every name on it, how fatherhood reshaped his purpose, and why staying in the Bay Area defined his career more than any move to LA or New York. Squint reflects on rediscovering black-and-white photography after losing his father and earning Steph Curry’s trust through consistency, humility, and discipline.

In this conversation, she breaks down the traits she’s seen across exceptional founders, the realities of building companies through cycles, and how early-stage investing has evolved over the last decade. She shares lessons on ownership, clarity, adaptability, and speed, and why the most enduring teams evolve faster than the markets around them. Christine reflects on backing thousands of founders worldwide, what she looks for in leaders under pressure, and how a global perspective shapes better decisions and more intentional company building.

In this conversation, he shares how he built his career across organizations with massive community impact, from Qualtrics to Smith Entertainment Group, and the lessons behind navigating billion-dollar city projects, activating live experiences, and helping bring an NHL team to Utah. He breaks down the principles that great leaders use to build trust, make clear decisions, and “never get blocked,” even in environments filled with complexity.

In this conversation, she shares how she went from Detroit public schools to Cass Tech and Wharton, then entered Silicon Valley and scaled teams from 14 to more than 1,000 at Google. From global leadership assignments to becoming a first-time CEO, she breaks down the lessons behind leading with conviction, humility, and principle.

In this conversation, Aaron Levie, co-founder and CEO of Box, shares how he turned a college project into a billion-dollar SaaS company. From building during the early days of the internet to leading through massive technological shifts, Aaron reveals the lessons behind Box’s evolution from a storage startup to a global platform used by 70% of the Fortune 500.

In this conversation, leadership expert Kim Scott, bestselling author of Radical Candor and Radical Respect, reflects on how honesty, empathy, and courage transform the way we work and lead. She shares the real story behind creating Radical Candor, coaching top CEOs at Dropbox and Qualtrics, and how her experiences at Google and Apple University shaped her approach to management and life.

In this conversation, Marc Randolph, co-founder and first CEO of Netflix reflects on how experimentation, rejection, and persistence shaped one of the world’s most influential startups. He shares the real story behind challenging Blockbuster, creating the first subscription model, and learning why curiosity often matters more than certainty.

Known as the father of the video game industry, the founder of Atari, and Chuck E. Cheese has spent five decades at the intersection of play, technology, and entrepreneurship. In this episode, he shares how fun, innovation, and relentless curiosity shaped Silicon Valley, and why the future of learning depends on making it fun.

In this episode, Anne Raimondi, COO and Head of Business at Asana, shares lessons from two decades leading fast-growth companies like Zendesk, SurveyMonkey, and TaskRabbit, serving on boards including Gusto and Patreon, and teaching leadership at Stanford GSB.

In this episode, Neal Harmon, CEO and co-founder of Angel, reveals how he went from a dairy farm in Idaho to building one of the fastest-growing entertainment companies in the world. Angel is behind global hits like Sound of Freedom, The Chosen, and Dry Bar Comedy — all chosen and funded by audiences, not executives.

In this episode, Jeremy Andrus, CEO of Traeger Grills and former CEO of Skullcandy, shares how he transformed two consumer brands into icons. From taking Skullcandy public to reinventing Traeger into the world’s number one wood-pellet grill company, Jeremy reveals the resilience and grit required to lead through chaos, culture shifts, and the toughest year of his career after going public.

In this episode, legendary Silicon Valley investor Navin Chaddha (Managing Partner at Mayfield) lays out a powerful prediction: “Every business will become an AI business — no exceptions.”

In this episode, Waseem Alshikh, co-founder and CTO of Writer, shares his extraordinary story. At 17, he launched his first startup in Syria — only to be imprisoned when the government tried to steal it for one dollar. In retaliation, he shut down the country’s internet and fled to Lebanon. From there, he taught himself English, built groundbreaking NLP tools, and eventually launched one of the world’s most trusted AI platforms.