Divot

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 humility, resilience, and long-term thinking still define the world's strongest leaders.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.A grounded masterclass in global insight, founder psychology, and building with purpose, offering a rare perspective on what it takes to scale, endure, and create lasting impact in a rapidly shifting world.Follow Christine - X (Twitter): https://x.com/christine_tsaiFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 — Early Curiosity, Identity & Finding Her Path3:12 — Lessons From Google & YouTube's Early Days6:58 — The Decision to Build a Global Investing Platform10:45 — Launching 500 & the Chaos of the First Years14:40 — How Early-Stage Investing Changed Over a Decade18:26 — The Traits She Sees in Exceptional Founders22:51 — Speed, Humility & the Signals That Truly Matter26:33 — Surviving Cycles & Leading Through Volatility30:55 — What Backing 3,000+ Founders Teaches You35:18 — Global Perspective: Why Innovation Comes From Everywhere39:07 — Leadership Moments That Define a CEO43:50 — Legacy, Purpose & Why Relationships Are the Real ScorecardFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#GlobalFounders #VentureCapital #StartupLeadership #EarlyStageInvesting #FounderMindset #ScalingStartups #GlobalInnovation #WomenInVC #LeadershipLessons #BuildingEnduringCompanies #Entrepreneurship #500Global

Mike Maughan, an executive with Smith Entertainment Group and co-founder of Five for the Fight, dives into the essence of impactful leadership. He discusses his transformative work on Salt Lake City's urban core, emphasizing the importance of community in billion-dollar projects. Maughan shares insights on the growing value of in-person connections amidst AI's rise, and the necessity of integrity and collaboration in leadership. He argues against chasing passion, instead advocating for solving meaningful problems, and highlights the importance of humility in leadership.

Stacy Brown Philpott, founder of Cherry Rock Capital and former CEO of TaskRabbit, reflects on her inspiring journey from a challenging upbringing in Detroit to leading teams at tech giants. She discusses lessons in grit and faith, breaking barriers to attend Wharton, and managing teams at scale. Stacy dives into the complexities of transitioning from COO to CEO, shares insights on investing in underrepresented founders, and emphasizes the importance of integrity in leadership. Her narrative is a powerful reminder that success can coexist with values and family.

Aaron Levie, co-founder and CEO of Box, transformed a college project into a billion-dollar SaaS platform. He dives into the lessons learned from Box's evolution and discusses the current AI disruption. Aaron explains why startups may thrive in new markets while incumbents should focus on adaptation. He highlights AI's potential to enhance productivity and the necessity for human oversight in automated processes. Plus, he shares insights on the changing role of CEOs in the AI landscape and emphasizes the importance of maintaining human relationships in business.

Kim Scott, New York Times bestselling author and leadership coach, dives into the principles of Radical Candor. She shares how her experiences at Google and Apple influenced her feedback-driven approach. Scott explores the origins of Radical Candor, emphasizing the balance of caring personally while challenging directly. She critiques the ineffective feedback sandwich and highlights the importance of honest communication in fostering trust. Valuable insights are offered on applying these ideas not just at work, but also in personal relationships.

Marc Randolph, co-founder and first CEO of Netflix, shares his entrepreneurial journey from a simple idea to challenging Blockbuster. He discusses the importance of experimentation, revealing that failure can lead to unexpected breakthroughs. The conversation touches on customer obsession, rapid-testing ideas, and cultivating a positive culture without losing personal balance. With insights on defining success, Marc emphasizes that ambition can coexist with a meaningful life, highlighting the moments that truly shape our paths.

Nolan Bushnell, the visionary behind Atari and Chuck E. Cheese, reflects on the playful origins of his groundbreaking companies. He delves into how fun and innovation shaped Silicon Valley, shares his thoughts on the importance of game-based learning through his venture, Exodexa, and explores the impact of AI in education. Nolan discusses lessons from mentors, the concept of 'marinating' ideas, and offers candid parenting advice. His insights reveal why creativity and persistence are crucial in facing challenges and shaping the future.

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 immigrants, why curiosity became her leadership superpower, and how she balances ambition with humility. You'll hear her talk about building resilient culture, using humor in high-pressure rooms, navigating perfectionism, and bringing AI into teams with trust and clarity.Follow Anne Raimondi - X (Twitter): https://x.com/anneraimondiFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - From San Jose roots to Asana's COO1:13 - Childhood lessons from immigrant parents2:21 - Seeing herself as a problem solver2:46 - Curiosity as a leadership superpower4:12 - Building advocacy with customers and employees5:15 - Staying lighthearted in high-pressure rooms7:19 - Using humor and honesty to diffuse tension9:03 - Leading without yelling: turning up the right "dials"11:04 - Rallying teams around the customer's voice13:03 - What makes someone have outsized impact14:34 - Healthy ambition vs. territorial behavior17:24 - Why fun and joy matter at work18:26 - Defining culture: mission + values + norms20:17 - How to evaluate a company's culture23:01 - Can you change culture or must you choose it?24:34 - Leadership training and conscious leadership at Asana26:07 - Serving on boards: how she got her first seat29:07 - How board work makes you a better operator33:49 - Why she wanted to be in the boardroom33:57 - On being a "recovering perfectionist"34:54 - Balancing family, career, and letting go of perfection35:57 - What her kids might say about her work39:45 - Privilege, gratitude, and immigrant perspective39:45 - AI's impact on how teams are built42:02 - How to bring AI into a resistant culture43:19 - Asana's "AI first" approach46:07 - The leader she most admires48:16 - The one idea she'd implant in everyone's mind49:08 - Hardest accomplishment: 30-year marriage50:20 - Her best advice on resilience and bouncing back50:55 - What she's most proud of in her career52:02 - The measure of a life well lived53:11 - The impact she hopes to leave on the worldFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#DivotPodcast #Leadership #Culture #Curiosity #JoyAtWork #Asana #Entrepreneurship #Resilience #TeamBuilding #AI

Neal Harmon, CEO and co-founder of Angel, transitioned from a dairy farm in Idaho to disrupt Hollywood by creating audience-driven hits like Sound of Freedom and The Chosen. He shares insights on surviving a $62 million lawsuit from Disney, emphasizing how hardships can foster resilience. Neal discusses the power of community-driven content and the innovative Angel Guild model that lets audiences greenlight projects. He also reveals lessons from viral marketing strategies that have helped shape Angel's success and the importance of balancing family life with ambitious goals.

In this discussion, Jeremy Andrus, CEO of Traeger Grills and former CEO of Skullcandy, delves into his journey of transforming brands into cultural icons. He shares insights on overcoming crises, particularly after Traeger's IPO, and emphasizes the shift from financial success to meaningful leadership. Jeremy also explores building products that foster community, the importance of daily habits, and how he instills tenacity in his six children. His candid perspective redefines success as creating joy and connection, not just profit.