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_tsai
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Early Curiosity, Identity & Finding Her Path
3:12 — Lessons From Google & YouTube's Early Days
6:58 — The Decision to Build a Global Investing Platform
10:45 — Launching 500 & the Chaos of the First Years
14:40 — How Early-Stage Investing Changed Over a Decade
18:26 — The Traits She Sees in Exceptional Founders
22:51 — Speed, Humility & the Signals That Truly Matter
26:33 — Surviving Cycles & Leading Through Volatility
30:55 — What Backing 3,000+ Founders Teaches You
35:18 — Global Perspective: Why Innovation Comes From Everywhere
39:07 — Leadership Moments That Define a CEO
43:50 — Legacy, Purpose & Why Relationships Are the Real Scorecard

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#GlobalFounders #VentureCapital #StartupLeadership #EarlyStageInvesting #FounderMindset #ScalingStartups #GlobalInnovation #WomenInVC #LeadershipLessons #BuildingEnduringCompanies #Entrepreneurship #500Global

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 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.

He reflects on the power of in-person connection in the age of AI, the importance of working with good people, and why ego and humility must coexist for leaders to scale. From frameworks for choosing what matters to the truth about toxic cultures, he explains why solving meaningful problems creates better careers than chasing passion.

A grounded masterclass in clarity, purpose, and impact, proving that real leadership is built on service, courage, and the commitment to make things happen.

Follow Mike - X (Twitter): https://twitter.com/MikeMaughan
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Why Being Different Beats Being 10x Better
1:25 — Transforming Salt Lake City’s Urban Core
5:26 — The Value of In-Person Connection in the AI Era
8:42 — A Framework for Choosing What Actually Matters
10:02 — Working With Good People & Recognizing Integrity
14:15 — The Cost of Toxic Environments
19:03 — Don’t Chase Passion — Solve Big Problems
25:05 — Ego + Humility: The Rare Leadership Combo
31:01 — Building Five for the Fight & Meaningful Causes
36:23 — Service as a Competitive Advantage
43:36 — How Great Leaders Deliver Hard News
57:44 — Bringing an NHL Team to Utah & Making Vision Real

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#Leadership #PurposeDriven #ScalingImpact #CommunityBuilding #HighPerformance #AIandHumanConnection #SportsBusiness #FoundersMindset

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 leadership assignments to becoming a first-time CEO, she breaks down the lessons behind leading with conviction, humility, and principle.

She reflects on navigating high-stakes decisions, building trust at the executive level, and helping guide a major strategic transaction with one of the world’s most iconic companies. From serving on public company boards to investing at the Series A and B stage, she explains how operating experience shapes venture judgment and why she built a fund designed to support underestimated talent at scale.

A masterclass in purpose-driven leadership, discipline, and belief, proving that success does not require sacrificing values, family, or faith, and that building with integrity is not a weakness, but a competitive advantage.

Follow Stacy - X (Twitter): https://x.com/sbp04
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Growing Up in Detroit: Faith, Family & Strong Women
2:18 — Motown Culture, Community & Early Joy
4:01 — Hard Things Young: Grit & Gratitude in Scarcity
5:47 — “God Will Make a Way”: Faith in Difficult Moments
6:58 — Two Things Can Be True: Effort vs Surrender
8:32 — Education as Escape: Earning a Shot at Cass Tech
10:12 — Wharton Dreams Without a Roadmap
12:45 — Breaking Into Tech & Entering Silicon Valley
16:22 — From 14 to 1,000 Employees: Learning to Lead at Scale
19:06 — Leading in India: Humility, Culture & Listening
22:54 — Becoming CEO: Pressure, Confidence & Faith
28:30 — The IKEA Deal: Inside a Transformational Acquisition
33:44 — How Great Boards Really Work (No Surprises Rule)
48:10 — Building Cherry Rock Capital & Investing With Purpose
50:20 — How She Chooses Founders & Helps Them Scale
1:11:26 — Mind Over Matter: Overcoming Hard Seasons
1:12:12 — Marriage Strength & Building a Life Together
1:12:42 — Legacy: Faith, Kids, Meaning & Life’s Real Scorecard

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#Leadership #SiliconValley #WomenInTech #TaskRabbit #Google #VentureCapital #FaithInBusiness #Entrepreneurship #FounderMindset #ScalingStartups

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 behind Box’s evolution from a storage startup to a global platform used by 70% of the Fortune 500.

He reflects on the rise of AI, how it’s reshaping the software industry, and why this moment mirrors the early days of cloud computing. From the changing economics of software to the new era of AI agents, Aaron explains what it takes to stay relevant and keep innovating when the rules of business change overnight.

A masterclass in resilience, adaptability, and leadership from one of Silicon Valley’s most curious minds, proving that innovation is less about technology and more about the people who dare to rethink it.

Follow Aaron - X (Twitter): https://x.com/levie
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 – Welcome to Divot: Making Your Mark on the World
0:19 – From College Project to $4 Billion Company
1:31 – Free Rent, Big Dreams & Dropping Out
2:43 – The Birth of Box and the Cloud Idea
3:49 – The Pivot That Changed Everything
6:45 – AI Disruption: Startups vs Incumbents
10:56 – The New Economics of AI and Software
13:07 – What Clay Christensen Still Teaches Us
15:31 – AI Agents and the Future of Work
20:17 – Managing Teams in the AI Era
26:10 – How Box Shifted to an AI-First Company
40:41 – Leadership, Abundance Mindset & Life Lessons

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#AI #FutureOfWork #Leadership #Startups #Entrepreneurship #SaaS #CloudComputing #AIInnovation #AaronLevie #Box #TechLeadership #DivotPodcast

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, coaching top CEOs at Dropbox and Qualtrics, and how her experiences at Google and Apple University shaped her approach to management and life.

You'll learn how to give feedback that inspires growth, build teams rooted in respect, and create cultures where truth replaces fear. From her first lessons in Moscow to building global impact in Silicon Valley, Kim reveals why clarity is kindness, and why radical candor is the foundation of lasting trust.

A timeless conversation for founders, creators, and leaders searching for authenticity, courage, and connection in a noisy world.

Kim – X (Twitter): https://x.com/kimballscott
Follow Derek – X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 – Love and Truth: The Heart of Radical Candor
0:32 – Meet Kim Scott: Redefining Modern Leadership
1:09 – From Google and Apple to a Global Movement
5:07 – From Moscow to Silicon Valley: An Unlikely Journey
10:20 – The Birth of Radical Candor with Dan Pink
13:22 – The “Bob Story”: When Kindness Becomes Cruel
20:15 – The Radical Candor Framework Explained
24:25 – Why the Feedback Sandwich Doesn't Work
31:15 – Speaking Truth to Power: Feedback Up, Down & Sideways
39:00 – Radical Respect: Humanity over Hierarchy
50:07 – Coaching Tech CEOs and Building Trust
58:42 – Radical Candor at Home and Final Reflections

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#RadicalCandor #Leadership #FeedbackCulture #HonestLeadership #RadicalRespect #WorkCulture #StartupLeadership #EmotionalIntelligence #LeadershipDevelopment #DivotPodcast

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, and learning why curiosity often matters more than certainty.

You’ll hear rare insights on how to test ideas quickly, stay optimistic through failure, and build a lasting culture without losing yourself in the process. More than a story of business success, this is about designing a meaningful life, where ambition and balance can coexist.

A timeless reflection for founders, creators, and leaders searching for clarity, courage, and direction in their own journey.

Marc - X (Twitter): https://x.com/mbrandolph
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 - Intro & Early Lessons - Learning to love the hard parts of the journey
1:00 - Founding Netflix - The idea, early experiments, and the DVD-by-mail breakthrough
8:00 - Beating Blockbuster - Finding product-market fit and using subscription to win
17:00 - That Will Never Work - Rejection, optimism, and lessons from failure
26:00 - Customer Obsession - Testing, talking to users, and learning fast
35:00 - Subscription Revolution - Reinventing media and business models
44:00 - Disruption Strategy - Why big companies can’t pivot and how startups win
54:00 - Looker Story - Building again, scaling a B2B SaaS, and selling to Google
1:03:00 - Redefining Success - What truly matters after billions made
1:12:00 - Work-Life Balance - Designing a life that scales with your ambition
1:20:00 - Founder Mindset - Focus, intuition, and ignoring noise
1:27:00 - Legacy & Wisdom - Optimism, empathy, and success beyond work

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#NetflixStory #Entrepreneurship #Innovation #Leadership #StartupLessons #WorkLifeBalance #Resilience #SiliconValley #BusinessGrowth #FoundersJourney #Inspiration #StreamingRevolution

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 it fun.

From pioneering the first home video games and building Atari into a cultural phenomenon, to creating Chuck E. Cheese and inspiring a generation of entrepreneurs, including Steve Jobs, he has shaped industries and defined eras. Today, his focus is on AI and education through his new venture, Exodexa, which he believes can transform how children learn by turning school into play.

He reflects on the happy accidents that led him to Atari, the unconventional culture that made Atari thrive, and why playfulness is essential to creativity and innovation. He opens up about raising eight children, the lessons he learned from mentors like Intel's Bob Noyce, and why persistence and relentlessness have been his greatest tools in overcoming challenges.

This is a raw and inspiring conversation for entrepreneurs, creators, and leaders who want to shape the future by rethinking what's possible.

Nolan - X (Twitter): https://x.com/nolbushnell
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 - Introduction
3:10 - Childhood & influence of play
7:30 - The early “happy accidents” that led to Atari
12:45 - Chuck E. Cheese origin & branding
17:50 - Short fun vs long fun in product design
22:30 - Culture at Atari / Silicon Valley roots
27:15 - AI's future and reinvention of education
31:40 - Passion, intensity, and entrepreneurial mindset
36:55 - Thoughts on raising eight children
41:20 - Lessons from mentors, especially Bob Noyce
45:30 - Advice on persistence and relentlessness
50:10 - Legacy: fun, learning, and transformation

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#Entrepreneurship #Leadership #Atari #ChuckECheese #ArtificialIntelligence #Education #Startups #Resilience #Innovation #SiliconValley #Gaming #FutureOfLearning

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/anneraimondi
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 - From San Jose roots to Asana's COO
1:13 - Childhood lessons from immigrant parents
2:21 - Seeing herself as a problem solver
2:46 - Curiosity as a leadership superpower
4:12 - Building advocacy with customers and employees
5:15 - Staying lighthearted in high-pressure rooms
7:19 - Using humor and honesty to diffuse tension
9:03 - Leading without yelling: turning up the right "dials"
11:04 - Rallying teams around the customer's voice
13:03 - What makes someone have outsized impact
14:34 - Healthy ambition vs. territorial behavior
17:24 - Why fun and joy matter at work
18:26 - Defining culture: mission + values + norms
20:17 - How to evaluate a company's culture
23:01 - Can you change culture or must you choose it?
24:34 - Leadership training and conscious leadership at Asana
26:07 - Serving on boards: how she got her first seat
29:07 - How board work makes you a better operator
33:49 - Why she wanted to be in the boardroom
33:57 - On being a "recovering perfectionist"
34:54 - Balancing family, career, and letting go of perfection
35:57 - What her kids might say about her work
39:45 - Privilege, gratitude, and immigrant perspective
39:45 - AI's impact on how teams are built
42:02 - How to bring AI into a resistant culture
43:19 - Asana's "AI first" approach
46:07 - The leader she most admires
48:16 - The one idea she'd implant in everyone's mind
49:08 - Hardest accomplishment: 30-year marriage
50:20 - Her best advice on resilience and bouncing back
50:55 - What she's most proud of in her career
52:02 - The measure of a life well lived
53:11 - The impact she hopes to leave on the world

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#DivotPodcast #Leadership #Culture #Curiosity #JoyAtWork #Asana #Entrepreneurship #Resilience #TeamBuilding #AI

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 split was harder than Disney, and how resilience, faith, and community helped Angel scale against all odds. He explains the secrets to viral storytelling, why constant testing wins, and how community-driven content is rewriting the rules of media.

This is a story of resilience, disruption, and purpose, a blueprint for every builder, leader, and creator who wants to build something that lasts.

Follow Neal Harmon - X (Twitter): https://x.com/nealsharmon
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 - Intro: from Idaho farm to Hollywood disruptor
2:30 - Why Angel gives audiences the power to greenlight stories
6:00 - Building hits like Sound of Freedom, The Chosen, and Dry Bar Comedy
10:00 - Lessons from AuraBrush, Squatty Potty, and viral ads
15:00 - Surviving Disney's $62M lawsuit and crowdfunding $11M in 5 days
21:00 - Why lawsuits can build resilience, not break it
26:00 - The pain of The Chosen split and lessons learned
33:00 - Angel Guild and the future of audience-driven entertainment
38:00 - Preparing for AMGX: scaling with community investors
44:00 - Family, faith, and raising 10 kids while building a company
50:00 - What makes Angel Studios different from Hollywood
55:00 - Neal's advice: why failure isn't real until you quit
1:00:00 - Final reflections: leadership, humility, and legacy

Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#DivotPodcast #Entrepreneurship #Leadership #Resilience #AngelStudios #SoundOfFreedom #TheChosen #DryBarComedy #DisruptHollywood #BusinessStrategy #StartupStories #CommunityBuilding #FaithInBusiness

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 grit required to lead through chaos, culture shifts, and the toughest year of his career after going public.

We dive into the formula for building products people love, why culture and community fuel legendary brands, and how Jeremy redefined success from chasing money to creating meaning. He also opens up about raising a family of six, designing daily habits for strength, and why joy, not status, is the ultimate measure of life.

This is a raw and inspiring conversation for entrepreneurs, leaders, and anyone who wants to build with purpose and lead with resilience.

Follow Jeremy Andrus – Instagram: https://www.instagram.com/jeremy_andrus/
Follow Derek – X (Twitter): https://twitter.com/derekjandersen

Timestamps:

0:00 – Intro: turning products into experiences
2:00 – Food, community, and the emotional power of brand
6:00 – Why Traeger is about more than grills
10:00 – TVAC: the formula for building products that people love
13:00 – From financial pressure to purpose-driven leadership
18:00 – Sharing success with your team and rewarding loyalty
26:30 – Surviving IPO challenges and leading through 2022
28:30 – Finding happiness while going through pain
34:00 – Ego, humility, and separating identity from success
40:00 – Family, partnership, and redefining balance
48:00 – Morning routines, mini-habits, and building daily strength
57:00 – Teaching grit and tenacity to the next generation
1:03:00 – Core principles for building an authentic brand
1:09:00 – Culture, community, and scaling values worldwide
1:13:00 – Rapid fire: best advice, resilience, and measuring life

Follow Divot:

YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags

#DivotPodcast #Leadership #Entrepreneurship #Resilience #BusinessGrowth #BrandBuilding #WorkLifeBalance #PersonalGrowth #CommunityBuilding #Success #Traeger #Skullcandy