Divot

Before building Crumbl, Jason McGowan was a tech founder focused on virality, creating products used by over 120 million people. He then made a bold move: leaving tech to start a simple cookie business. In this conversation with Derek Andersen, Jason shares how Crumbl grew from one chocolate chip cookie into a $1B+ franchise with 1,000+ locations across the U.S. He explains how product-market fit,...

Before teaching negotiation at Stanford, Stan Christensen spent decades advising leaders on high-stakes negotiations around the world. From corporate finance on Wall Street to the consulting arm of the Harvard Negotiation Project, he has worked across more than 75 countries helping leaders navigate complex negotiations where the outcome can shape companies, careers, and international relationships...

Before building one of the fastest-growing legal technology companies in the United States, Ryan Anderson was a practicing lawyer frustrated by deadlines, paperwork, and systems that made it easy to miss critical details. Instead of accepting the chaos of legal operations, he decided to build a better system. In this conversation with Derek Andersen, Ryan shares how that decision became Filevine,...

Before becoming one of the most respected independent mechanics in the United States, Dave Bell was a young man battling addiction, jail time, and the fear of losing everything. Over the past 36 years, he rebuilt his life the same way he rebuilds engines, with discipline, precision, and relentless ownership. In this conversation, Dave shares how he grew from a one-bay storage unit during the 1990...

Recorded at LinkedIn headquarters in Mountain View, this episode features Tomer Cohen, former Chief Product Officer of LinkedIn and one of the product leaders behind how over one billion professionals connect, work, and create economic opportunity at global scale. In conversation with Derek Andersen, Tomer breaks down what it takes to build great products inside large organizations, how LinkedIn e...

Recorded on Sand Hill Road at the iconic offices of Kleiner Perkins , this episode features Mamoon Hamid , one of the most influential investors of this generation. Mamoon has backed category-defining companies, including Slack, Figma, Box, Yammer, Glean, Intercom, and more, and now serves as a partner stewarding one of Silicon Valley’s most historic venture firms. In conversation with Derek Ander...

Before becoming a leader at the intersection of fashion, retail, and technology, Julie Bornstein built her career through persistence, curiosity, and conviction. Early on, she broke into the industry by reaching out directly to designers she admired, setting the foundation for a career that would later span Nordstrom, Sephora, Stitch Fix, and multiple consumer technology companies shaping how peop...

Before becoming one of the most respected early-stage investors in Silicon Valley, Niko Bonatsos was an immigrant from Greece navigating academia, visas, and uncertainty while searching for opportunity in the United States. Over the next 15 years, he became a Managing Director at General Catalyst, investing in iconic companies like Snap and Discord and backing technical founders long before their...

Before becoming one of the most influential evangelists in the history of technology, Guy Kawasaki was part of Apple’s original Macintosh team, working directly with Steve Jobs during the early days of personal computing. His career has been defined by independent thinking, deep curiosity, and a lifelong commitment to building and evangelizing products that truly matter. In this conversation, Guy...

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. Over his career, Bob has shaped more than 100,000 surfboards , becoming a defining force in modern surfboa...

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...