Divot

By Derek AndersenBusiness

Divot episodes

April 01 #43: Success Won’t Fix You (What a $4B CEO Learned Too Late)
Before leading a $4B company, Adam Edmunds spent years trying to prove he was good enough. From cold emailing CEOs as a student to building his first company, his journey started with uncertainty and a relentless need for validation.
In this conversation with Derek Andersen, Adam shares how he became CEO of Entrata, a platform powering over 20,000 apartment communities worldwide, raising $700M+ and reaching a $4B+ valuation. He breaks down what it really takes to scale a company at that level.
Adam explains why relationships are the most valuable currency in business, how great leaders recruit over years, not weeks, and why reputation determines the ceiling of your success. He also shares hard lessons on hiring, culture, and long-term thinking.
The episode goes deeper into identity, failure, and self-worth, why success doesn’t fix how you feel about yourself, and how learning to stop seeking external validation changed everything about how he leads and lives.
Follow Adam - X (Twitter): https://x.com/adamedmunds
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Everything you need to build and scale AI agents, from tools to expert guidance: g.co/startupagentguide
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride: https://tinyurl.com/PulleyPartner
Timestamps:
03:52 — The Power of Starting Before You’re Ready
07:41 — Cold Emails That Changed His Life Forever
12:58 — Building His First Company From Scratch
18:36 — Inside a $4B Company (Entrata Breakdown)
24:11 — How Great CEOs Think About Hiring Talent
30:27 — Why Relationships Are the Ultimate Business Asset
36:48 — Leadership, Culture, and Scaling Teams
43:55 — The Hidden Cost of Success and Achievement
50:12 — Why Success Doesn’t Fix Your Self-Worth
56:34 — Redefining Identity Beyond Business
1:01:22 — What Actually Matters at the End
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:
#ceomindset #startupgrowth #scalingbusiness #founderjourney #leadershipskills #buildinginpublic #entrepreneurmindset #businessstrategy #personalgrowth #divotpodcast
1 hr 9 min
March 25 #42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie
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, A/B testing, and viral growth turned a simple idea into a national brand.
Jason breaks down why product matters more than marketing, how customer obsession drives growth, and how Crumbl built a viral experience through sharing, weekly drops, and community feedback.
The episode also explores leadership, success, and why money doesn’t create lasting happiness. Jason reflects on family, purpose, and what truly matters after building a billion-dollar company.
Follow Jason - X (Twitter): https://x.com/jasonmcgowan
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
04:32 — Building the Perfect Cookie With A/B Testing
07:18 — The Bubblegum Cookie Failure (Hard Lesson)
08:54 — The Simple Idea Behind Crumbl’s Viral Growth
17:58 — Owning the Customer (Lessons from Facebook)
20:03 — How Crumbl Accidentally Became a Franchise
22:43 — Why Product Matters More Than Marketing
26:18 — Reading Reddit as CEO (Customer Obsession)
30:34 — Scaling Crumbl Nationwide
34:16 — Weekly Drops: The Genius Behind the Menu
44:48 — Money Doesn’t Buy Happiness (Real Talk)
46:25 — Family, Purpose, and What Actually Matters
54:53 — The Truth About Success and Fulfillment
59:26 — Just Get Started (Final Advice)
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:
#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast
1 hr 2 min
March 18 #41: Stanford Negotiation Expert Reveals the Psychology of Winning Any Negotiation
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.
In this conversation with Derek Andersen, Stan explains why most people misunderstand negotiation. Instead of treating it like a battle where one side wins and the other loses, he argues that the best negotiators focus on preparation, deep listening, and creative problem-solving to build outcomes where both sides leave stronger.
Stan shares lessons from venture capital negotiations, startup fundraising, job offer negotiations, and company acquisitions. He explains why founders should never negotiate with only one investor, why controlling the process matters when selling a company, and why the biggest mistake negotiators make is agreeing to deals they should walk away from.
The episode goes deeper into leadership, persuasion, and human psychology, exploring why negotiation is ultimately about relationships.
Subscribe to Stan’s Podcast - YouTube: https://www.youtube.com/@AllThingsNegotiation
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
00:04:06 — The Steve Young Story: Giving People What They Value Most
00:05:18 — Why Fairness Matters in Negotiation
00:06:12 — Preparing for High-Stakes Negotiations
00:07:34 — Why the Best Negotiators Listen More Than They Speak
00:08:45 — Why Negotiation Is Creative Problem Solving
00:11:06 — The Biggest Mistake in Business Negotiations
00:12:29 — How to Negotiate a Job Offer (Early vs Senior Career)
00:17:30 — Venture Capital Negotiations: Why Founders Need Leverage
00:29:51 — Selling a Company: Why You Must Control the Process
00:39:27 — The Story That Solved a 100-Year Conflict
00:46:07 — How Stan Measures Success in 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:
#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast
48 min
March 11 #40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform
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, a legal tech platform now serving nearly 6,000 customers, employing more than 700 people, and generating more than $200 million in annual revenue. He explains how AI is transforming legal work and why technology can dramatically improve outcomes for lawyers and their clients.
Ryan also opens up about rebuilding Filevine to become an AI-native company. From rewriting years of engineering work to navigating one of the fastest-moving industries in the world, he reflects on leadership, conviction, and what it takes to adapt when technology changes everything.
The episode goes deeper into entrepreneurship, justice, and purpose, exploring why access to legal systems is expanding and why great lawyers will become even more powerful with AI.
Follow Ryan - X (Twitter): https://x.com/ryanm_anderson
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
02:42 — What Filevine Actually Does (Legal AI Explained)
04:08 — The Problem That Inspired Filevine
05:03 — The Risk Conversation With His Wife
09:03 — Meeting the Engineer Who Built the Vision
11:56 — The Founder Mindset: “I’ll Figure It Out”
18:20 — The Day Ryan Quit His Job
22:14 — Rewriting Filevine for the AI Era
25:41 — How AI Is Changing Software Teams
31:28 — Why the Legal Industry Could Grow 100x
44:55 — The Future of Law: AI Running Legal Work
55:20 — The Mindset to Build a Billion-Dollar Company
01:06:10 — Ryan’s Real Definition of Success
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:
#RyanAnderson #LegalAI #LegalTech #Entrepreneurship #SaaS #ArtificialIntelligence #Leadership #Justice #Innovation #DivotPodcast
1 hr 8 min
March 04 #39: How Master Mechanic Dave Bell Built an 8M-Follower YouTube Empire
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 recession into a 33,000-square-foot auto center with 35 employees, and how an unexpected leap into social media led to more than 8 million followers across YouTube, TikTok, and Instagram. He explains why opposition is an opportunity, how elite mechanics think, and why authenticity online outperforms any marketing budget.
Dave also opens up about addiction, faith, jail, and the turning points that changed his trajectory. From reading Atlas Shrugged behind bars to building one of the largest independent automotive brands in the world, he reflects on agency, momentum, and the power of choosing who you become.
The episode goes deeper into leadership, fatherhood, and legacy, exploring what it means to master yourself, redefine a misunderstood industry, and live by a simple philosophy: never let anyone else define who you are.
Follow Dave - Instagram: https://www.instagram.com/davesautocenter
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
02:42 — From 300 Followers to 8 Million: The Unexpected Breakthrough
09:07 — “Who Are You?” The Identity Wake-Up Call
13:19 — A Mission Bigger Than Cars: Changing an Entire Industry
16:55 — Fearless: What Separates Elite Mechanics from Everyone Else
26:42 — “Don’t Ever Let Anyone Define You” (A Father’s Turning Point)
33:14 — The 4 O’s: Turning Opposition Into Opportunity
45:17 — Drugs, Fast Money & Walking Away Before It Was Too Late
50:48 — Rock Bottom at 35: Addiction, Faith & Choosing a Different Path
57:35 — Six Months in Jail & The Book That Rewired His Mind
01:01:50 — The Hard Truth: The Moment You Blame, You Lose
01:09:40 — Momentum, Waves & The “Perfect Soup” Theory of Life
01:10:11 — In the End, Only One Thing Matters
Follow Divot:
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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:
#DaveBell #Entrepreneurship #AddictionRecovery #MechanicLife #Leadership #BusinessGrowth #SocialMediaSuccess #AtlasShrugged #PersonalDevelopment #Agency #Momentum #AutoIndustry #DivotPodcast
1 hr 17 min
February 25 #38: Building Great Products, Product Leadership & the Future of Work with Tomer Cohen (LinkedIn)
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 evolved into a mobile-first platform, and what product leadership really means when operating at massive scale.
The discussion expands into AI and the future of work, where Tomer explains the rise of the full-stack product builder, how AI is collapsing traditional roles across product, design, and engineering, and why builders who combine vision, empathy, and execution will define the next generation of companies.
The episode closes with deeply personal reflections on growth mindset, restraint, resilience, faith, and the idea that true freedom lives in the space between stimulus and response.
Follow Tomer - LinkedIn: https://www.linkedin.com/in/tomercohen
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
00:00 — Between Stimulus and Response: Where Freedom Truly Lives
08:55 — Rebuilding LinkedIn for Mobile Before It Was Obvious
11:02 — Turning LinkedIn Into a Daily Habit, Not a Transaction
13:34 — Why Authentic Voices Beat Corporate Talk Every Time
18:24 — Conviction Over Titles: Choosing Where to Make Impact
20:28 — The Rider and the Elephant: How Organizations Really Move
24:42 — What Separates a Good Product from a Truly Great One
31:34 — Restraint: The Hidden Skill Behind Billion-Dollar Products
35:09 — Slowing Down to Fix the Core Before Scaling
39:12 — The Rise of the Full-Stack Product Builder
42:02 — How AI Is Collapsing Roles and Restoring Meritocracy
53:25 — The Truth About Success: There Are No Shortcuts
59:55 — The Final Lesson: Choosing How You Respond
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:
#TomerCohen #LinkedIn #ProductLeadership #BuildingGreatProducts #AI #FutureOfWork #ProductManagement #StartupLeadership #GrowthMindset #DivotPodcast
1 hr 8 min
February 18 #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)
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 Andersen, Mamoon breaks down how great investors evaluate founders, why conviction starts with why, and what separates category creators from incremental startups.
The discussion expands into AI, where Mamoon shares why this cycle is fundamentally different from every prior technology wave. He explains why AI is not just software but labor, how it’s reshaping productivity across professions, and why adoption and monetization are happening faster than ever, from copilots to autonomous agents transforming how work gets done.
The episode closes with deeply personal reflections on resilience, immigration, parenting, faith, and purpose.
Follow Mamoon - X (Twitter): https://x.com/mamoonha
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
00:00 — “God Is the Best of Planners” — Faith, Loss & Letting Go of Control
01:40 — Inside the Most Powerful Room in Silicon Valley (Why It’s Rarely Used)
05:05 — What Elite Investors Actually Listen For in Founder Pitches
06:55 — Why Metrics Don’t Matter If You Can’t Explain Your “Why”
10:30 — How Slack & Box Were Backed When the Market Didn’t Exist
14:25 — Why AI Is the Biggest Technology Shift in 30 Years
18:50 — AI Isn’t Software — It’s Labor (And That Changes Everything)
23:30 — The Future of Work: What Humans Will Do Better Than AI
27:10 — Leaving Your Own Firm to Rebuild a Legendary One
31:05 — The Apprenticeship Model That Built Venture Capital Giants
35:45 — Growing Up Between Germany & Pakistan — Lessons in Resilience
39:30 — How Do You Raise Resilient Kids in an Easy World?
42:55 — Why Sports Might Be the Best Teacher of Grit
49:55 — The Hajj: Witnessing the Best of Humanity Under Extreme Conditions
56:20 — Inshallah — Ambition, Failure & Accepting God’s Will
59:35 — How Mamoon Hamid Measures a Life Well Lived
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:
#MamoonHamid #KleinerPerkins #VentureCapital #AI #FutureOfWork #Startups #Founders #FaithAndWork #Leadership #DivotPodcast
1 hr 2 min
February 11 #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech
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 people discover what they wear.
In this conversation, Julie shares what she learned building and scaling consumer products and why fashion is one of the most complex categories for technology to understand.
Julie also reflects on the rapid shift now underway in commerce, as AI begins to reshape how people search, discover, and decide. She discusses why traditional e-commerce search fails in taste-based categories, how large language models unlock new possibilities for personalization, and what this moment has in common with earlier platform shifts like social and mobile.
The episode goes deeper into purpose and long-term thinking, exploring trust, incentive alignment, and how technology should serve people rather than manipulate them.
Follow Julie - X (Twitter): https://x.com/juliebornstein
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
02:18 — She Broke Into Fashion by Writing Letters (No Network, No Shortcuts)
05:01 — The Business of Fashion Explained Simply (How Brands Really Make Money)
06:40 — Why Online Shopping Became Overwhelming (Too Much Choice Kills Confidence)
07:28 — Why Most Fashion Brands Fail (No Point of View, Wrong Pricing)
10:29 — Who Really Decides Fashion Trends? (Luxury, Runways & Fast Fashion)
14:28 — The Nordstrom Leader Who Saw E-Commerce Before Anyone Else
16:03 — Why Stitch Fix Didn’t Work for People With Real Taste
18:29 — Selling a Startup: 40K Customers vs 400M Users at Pinterest
23:52 — The 3 Reasons She Sold Her Company (Price, Market Crash, Team)
26:33 — Why ChatGPT Made AI Shopping Finally Possible
30:49 — Why Fashion Search Is Broken (Taste-Based, Not Keyword-Based)
34:10 — The Rule Behind Daydream: If the Customer Wins, We Win
44:30 — The Legacy She Wants to Leave (Making Shopping Smarter & Better)
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:
#JulieBornstein #AIShopping #FutureOfCommerce #ConsumerAI #FashionTech #RetailInnovation #Startups #Founders #Technology #DivotPodcast
47 min
February 04 #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win
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 ideas became obvious to the world.
In this conversation, Niko shares what he learned investing through multiple technology cycles and why most successful companies don’t start with the right idea.
Niko also reflects on the resurgence of San Francisco as the center of the AI revolution, how ChatGPT reshaped the startup landscape almost overnight, and why this moment feels similar to the early days of social networking and mobile. From recognizing momentum before metrics to investing in overlooked builders, he offers a rare inside look at how early-stage conviction is actually formed.
The episode goes deeper into purpose and legacy, exploring immigration, perseverance, parenting, and how Niko measures a life well lived. Rather than chasing status, money, or permanence, he explains why helping deeply obsessed builders bring their dreams to life and empowering others along the way is the mark that truly matters.
Follow Niko - X (Twitter): https://x.com/bonatsos
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
02:42 — Stanford & Silicon Valley: One Intertwined Ecosystem
06:18 — Why Founders Keep Chasing the Same Startup Ideas
07:37 — Investing Before Consensus: The Real Seed Advantage
08:22 — Why Most Successful Companies Don’t Start With the Right Idea
09:49 — San Francisco Is Back: The AI Gravity Shift
13:24 — Why Niko Invested Early in Snap
15:44 — Discord: How a Failed Startup Became a Generational Company
18:42 — Talent Is Universal, Opportunity Is Not
21:17 — The Signals That Make an Investor Lean In
26:49 — Can AI Replace Venture Capitalists?
31:30 — The Rise of Tiny Teams and Explosive Growth
34:01 — Why Non-AI Companies Are Fighting a Knife Fight
38:13 — Leaving General Catalyst: A New Chapter
42:18 — Alexander the Great & the Question of Legacy
48:19 — “Just Get Started”: The One Idea He’d Give Everyone
50:51 — How Niko Measures a Life Well Lived
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:
#NikoBonatsos #VentureCapital #AI #Startups #SiliconValley #EarlyStageInvesting #Founders #Snap #Discord #GeneralCatalyst #Entrepreneurship #Innovation #DivotPodcast
54 min
January 28 #34: Creativity, Obsession & Building Products That Change the World
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 reflects on working with Steve Jobs, the difference between mission-driven and ego-driven leadership, and why the best products are built by people solving problems for themselves. He shares hard-earned lessons from Silicon Valley on creativity, obsession, grit, and what it really takes to build things that last.
Guy also discusses his role as Chief Evangelist of Canva, the global design platform democratizing creativity for millions worldwide, and how recognizing great products early shaped his journey. From writing 18 books to advising startups and founders, he explains why authenticity consistently outperforms imitation in entrepreneurship and product building.
The episode goes deeper into purpose and legacy, exploring learning later in life, embracing setbacks, redefining success, and measuring impact not by status or money, but by one simple idea: empowering people.
Follow Guy - Instagram: https://www.instagram.com/guykawasaki
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Delve
Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
Timestamps:
1:09 — Starting Surfing at 60: Obsession Beats Talent
3:49 — Growing Up in Hawaii: Identity, Culture & Perspective
6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom
12:44 — Writing 18 Books: Why Most People Shouldn’t Write One
16:57 — Build for Yourself: The Origin of Great Products
18:20 — Working With Steve Jobs: Mission Over Ego
19:40 — Mission-Driven vs Ego-Driven Leadership
22:35 — The Halo Effect: Why You Should Be Skeptical of Authority
27:22 — Steve Jobs vs Elon Musk: Focus vs Scale
30:51 — Don’t Be the Next Steve Jobs. Be the First You
33:08 — Finding Your Calling: Loving the Entire “Sandwich”
46:31 — Jane Goodall: Purpose Without Retirement
52:19 — Guy’s Golden Touch: Finding Gold Early
57:24 — Grit as the Real Advantage
58:25 — Family, Legacy & Measuring a 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:
#GuyKawasaki #SteveJobs #ElonMusk #Apple #Canva #Entrepreneurship #Startups #Creativity #ProductBuilding #Leadership #Innovation #SiliconValley #Grit #Purpose #DivotPodcast
1 hr 2 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.