Divot

Before becoming one of the most influential venture capitalists in Silicon Valley, Tim Draper built a career defined by early conviction, independent thinking, and a willingness to back ideas long before they reached mainstream belief. Over decades, Tim has invested in and supported some of the most transformational companies of the modern era, shaping how the world communicates, moves money, expl...

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. Aparna has spent her career at the intersection of technology and human behavior, from leading product at Google and YouTube to shaping...

Josh Reeves, co-founder and CEO of Gusto , shares how he built one of the most trusted platforms for small businesses, and what it truly takes to scale a company with purpose. 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...

Before he became an award-winning filmmaker and humanitarian, Brandt Andersen built a tech company from scratch, scaled it to tens of millions in revenue, and sold it before moving into filmmaking, where he went on to produce major films like Everest, Lone Survivor, and American Made. But behind the success is a life shaped by extremes: a skydiving accident that nearly killed him, surviving the Ma...

Before he became chairman of the Napoleon Hill Institute, David Meltzer lived a life driven by scarcity, ambition, and the need to prove himself. Raised by a single mother in Akron, he chased success to change their future, eventually becoming a multimillionaire and CEO in the sports world. But behind the achievements was an identity built on ego, bad habits, and external validation, leading to th...

Before becoming the photographer trusted by the world’s biggest icons, Squint built his path on discipline, creativity, and a lifelong commitment to mastering storytelling. Raised in Palo Alto and shaped by years inside a TV studio before he turned 18, he grew from a kid with a camera into a filmmaker and cinematographer behind iconic portraits of Nas, Michael B. Jordan, Dave Chappelle, Draymond G...

Before helping elevate the rise of global entrepreneurship, Christine Tsai , CEO & Founding Partner of 500 Global , built her path on curiosity, consistency, and an instinct for spotting potential early. From her beginnings in tech to guiding an investing platform that now reaches founders across dozens of countries, her journey reflects a belief that great companies can start anywhere, and that h...

Before helping lead the transformation of Salt Lake City’s urban core, Mike Maughan’s journey was shaped by discipline, faith, service, and a belief that leadership is defined by integrity above everything else. 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 b...

Before leading global teams and raising more than $170 million to back exceptional founders, this journey started in a crowded home on the West Side of Detroit filled with Motown, discipline, and faith. 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 le...

Before the cloud powered the modern enterprise, it started with a college dorm, a borrowed garage, and a vision to make work simpler. 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 be...

Before Radical Candor reshaped how leaders give feedback, it began with a simple idea, that caring personally and challenging directly can coexist. 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, c...

Before Netflix changed entertainment forever, it began with a small idea, mailed in an envelope, and a lot of doubt. 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, a...

The journey from playful ideas to world-changing companies is never simple. 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 i...

Work is changing fast, but how do you build cultures and teams that thrive through it? 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. She opens up about growing up as the child of immigr...

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. Neal shares the painful story of surviving a Disney lawsuit, why The Chosen spl...

The journey from startup to global brand is never easy, but it’s the moments of crisis that define true leaders. 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 gri...

The world is changing fast — and there’s no going back. 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.” We dive into what that really means for founders, industries, and the future of work. Navin introduces the concept of “ vibe coding ”, where 8 billion peop...

How do you build an AI company trusted by the world's top enterprises, while surviving political oppression, hacking a country's internet, and rewriting the future of work? 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 retal...

How do you choose the right quest — the kind of mission that truly matters, and can survive in today’s world of regulation, politics, and entrenched incumbents? In this episode, Founders Fund General Partner and Anduril co-founder Trae Stephens shares his philosophy of “Good Quests” — and what entrepreneurs must get right when tackling hard, meaningful problems. We dive deep into how AI will trans...

In this inspiring conversation, we explore how AI will transform the future of business and work, and what it means for us as humans. You’ll hear why AI will soon perform 80% of human jobs, why full AI-first tools will surpass today’s co-pilots, and why most of AI’s impact will happen outside of tech. But this is also a powerful life masterclass. From building billion-dollar startups to raising a...

In this episode, Kobie Fuller invites us into his home gym — and into the mindset that’s driven him through elite athletics, startup investing, fatherhood, and personal growth. From sprint workouts to 24-hour fasts, Kobie shares how he uses physical discipline to sharpen mental clarity and lead with purpose. He breaks down two core ideas that changed his life: “It takes what it takes” and neutral...

Most people fail at leadership because they complicate what should be simple. Greg Osborn’s approach is different. After leading in Vietnam, raising a family with old-school work ethic, and building businesses in Silicon Valley as the tech boom took off, he learned that success comes from two things: giving people the right training and keeping them motivated. In this conversation, Greg breaks dow...

America used to lead the world in innovation. Now, it's falling behind — and no one in power wants to face the truth. In Part 2 of this eye-opening conversation, we dive into how the U.S. lost its edge in science, technology, and defense. From bloated bureaucracies to outdated mindsets, the systems that once fueled American greatness are now holding it back. You'll hear war stories from th...

Most founders follow advice that sets them up to fail. In this episode of Divot , we sit down with one of the most influential minds in startup history — Steve Blank . Before reshaping modern entrepreneurship, Steve co-founded E.piphany , a CRM company that went public in 1999 and soared to an $8 billion valuation. After multiple startups and hard-won lessons, he created the startup playbook that...

Liz Wiseman is one of the world’s leading voices on leadership and talent development. A Wall Street Journal best-selling author of Multipliers and Impact Players, Liz’s work has helped shape leaders at Apple, Google, Meta, and beyond. In this episode, she shares how growing up in Silicon Valley, facing early life challenges, and leading major teams taught her the power of multiplying — not dimini...