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, 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:
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Hashtags:
#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast

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:
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Hashtags:
#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast

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:
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LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#RyanAnderson #LegalAI #LegalTech #Entrepreneurship #SaaS #ArtificialIntelligence #Leadership #Justice #Innovation #DivotPodcast

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/divotPulley
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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Hashtags:
#DaveBell #Entrepreneurship #AddictionRecovery #MechanicLife #Leadership #BusinessGrowth #SocialMediaSuccess #AtlasShrugged #PersonalDevelopment #Agency #Momentum #AutoIndustry #DivotPodcast

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:
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Hashtags:
#TomerCohen #LinkedIn #ProductLeadership #BuildingGreatProducts #AI #FutureOfWork #ProductManagement #StartupLeadership #GrowthMindset #DivotPodcast