Divot

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

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

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

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

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