Divot

By Derek AndersenBusiness

Divot episodes

November 05, 2025 #23: The Box Story: Startup Lessons, AI Disruption, and the Future of Work
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
45 min
October 29, 2025 #22: The Radical Candor Mindset: Honest Leadership, Feedback, and the Power of Truth
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
1 hr 12 min
October 22, 2025 #21: The Netflix Story: Building, Failing, and Finding Balance from the Early Days of the Streaming
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
1 hr 32 min
October 15, 2025 #20: Founding Atari & Chuck E. Cheese, Shaping Silicon Valley, and Reinventing Education with AI
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
55 min
October 08, 2025 #19: Leading with Curiosity, Building Culture, and Finding Joy at Work
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
55 min
October 01, 2025 #18: Building Angel, Disrupting Hollywood, and Surviving $60M Disney Lawsuit
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
1 hr 9 min
September 24, 2025 #17: Reinventing Traeger, Building Skullcandy, and Leading Through Crisis
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
1 hr 20 min
June 25, 2025 #16: AI Will Turn Every Business Into an AI Business (No Exceptions)
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 people can become builders — simply by describing what they want. He shares why SaaS is dying, how vertical AI models will dominate entire industries, and why physical AGI will transform the real world — from robots to logistics to healthcare.
He also explains how billion-dollar companies will soon be built by teams of two or three people, thanks to the power of AI-native architecture.
This episode is a wake-up call for every founder, builder, and leader who wants to stay ahead in the new AI era.
Follow Navin Chaddha – X (Twitter): https://twitter.com/NavinChaddha
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
00:00 - Introduction
00:38 - The Excitement of AI Technology
02:10 - The Future of Coding and Development
04:20 - Collaborative Intelligence in Action
05:00 - The Era of 8 Billion Builders
06:01 - Democratizing Entrepreneurship with AI
07:42 - The Impact on Venture Capital
08:54 - The Renaissance of Hardware
11:44 - AI's Role in Physical Applications
13:50 - Disruption in Home Appliances
19:20 - Barriers to Physical AGI
20:52 - Reimagining Industries with AI
26:15 - The Great Equalizer of AI
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotdotorg
TikTok: https://www.tiktok.com/@divot.org
LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #VerticalAI #AGI #FutureOfWork #NavinChaddha #MayfieldFund #VibeCoding #StartupStrategy #Innovation #TechInvesting #SaaSIsDead
29 min
June 18, 2025 #15: Escaping Dictatorship, Hacking the Internet, and Building a World-Class AI Platform
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 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.
We explore how Writer built its own LLMs to serve enterprises like Uber, Deloitte, and Spotify; how AI agents are replacing outdated internal tools; and how a new generation of founders is reshaping pricing, trust, and innovation in the AI era.
This episode is a masterclass in surviving chaos, scaling with focus, and building AI-first from Day One.
Follow Waseem Alshikh - X (Twitter): https://x.com/waseem_s
Follow Derek Andersen - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
00:00 - Introduction to the Syrian Regime Collapse
00:49 - Early Success with Digital Mapping
01:42 - Government Takeover and Jail Experience
04:00 - Hacking the Internet for Revenge
05:36 - Escape to Lebanon and New Beginnings
06:44 - Learning English and Computer Science
08:08 - Transitioning to AI and Open Source
09:22 - Building Generative AI Models
10:15 - The Challenge of Language Localization
12:44 - Why We Built Our Own AI Models
13:30 - Enterprise Solutions and Customer Trust
18:04 - The Role of AI in Productivity
24:11 - Evolving Business Models in AI
28:35 - Future of AI in Regulated Industries
32:29 - Open Source vs. Proprietary AI
34:08 - Starting an AI Company Today
38:11 - The Journey from Startup to Growth
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotdotorg
TikTok: https://www.tiktok.com/@divot.org
LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #Innovation #StartupJourney #EnterpriseAI #MissionDriven #Resilience #WriterAI #FutureOfWork #Leadership #CTO #SaaS #DerekAndersen
41 min
June 11, 2025 #14: Choosing Good Quests: Innovation, AI, and Winning in a World of Regulation
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 transform defense and national security, why the future of warfare is distributed and AI-driven, and how entrepreneurs can navigate government sales and political opposition.
From raising capital to surviving regulated markets, this is a tactical and inspiring conversation for anyone building in ambitious, frontier spaces.
This episode is a masterclass in mission-driven entrepreneurship, AI strategy, and playing to win in a changing world.
Follow Trae Stephens – X (Twitter): https://twitter.com/traestephens
Follow Derek Andersen – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - Introduction: The Naivety of Building Products
0:20 - Welcome to Divot and Episode Overview
1:10 - Guest Introduction: Trae Stephens
1:32 - The Concept of Good Quests for Founders
3:50 - Identifying a Good Quest and Its Importance
6:40 - Market Size and Its Relevance to Good Quests
8:42 - Governance and Board Seats in Venture Capital
10:02 - Coaching Founders on Ethical Considerations
11:21 - Founding Anduril: Early Data Points and Insights
14:58 - Raising Capital: Strategies for Founders
17:55 - Selling to the U.S. Government and International Markets
21:18 - The Role of AI in Defense and Future Implications
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotdotorg
TikTok: https://www.tiktok.com/@divot.org
LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #Innovation #DefenseTech #Entrepreneurship #GoodQuest #MissionDriven #StartupLessons #Regulation #Leadership #TraeStephens
24 min

About Divot

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Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment.