Divot

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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LinkedIn: https://www.linkedin.com/company/divotdotorg
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:
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

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

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
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Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:
#JulieBornstein #AIShopping #FutureOfCommerce #ConsumerAI #FashionTech #RetailInnovation #Startups #Founders #Technology #DivotPodcast