Business Breakdowns

Today we are breaking down the cybersecurity giant, Cloudflare. 

Today, Cloudflare controls over 20% of the world’s web traffic, and more impressively, absorbs 2.5mn cyber attacks per second.

My guest is Sam Eden, Investor at Square Peg’s Global Tech Fund. And while I understood on the surface what Cloudflare does, Sam helped me get into the weeds on how the digital pipes actually work.

So we go through the rise of Cloudflare and how they differentiated themselves vs. the incumbents and fellow upstarts. Through this story, Sam details the product offerings that led to Cloudflare's leading market share, and what growth looks like moving forward. 

Please enjoy this episode on Cloudflare. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠⁠⁠⁠⁠⁠⁠ here.⁠⁠⁠⁠⁠⁠⁠

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This episode is brought to you by ⁠⁠⁠⁠Portrait Analytics⁠⁠⁠⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before.

Sign-up for a free trial today at ⁠⁠⁠⁠⁠portraitresearch.com⁠⁠⁠⁠⁠

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Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit ⁠⁠⁠⁠⁠⁠⁠joincolossus.com/episodes⁠⁠⁠⁠⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠).

Timestamps 

(00:00:00) Welcome to Business Breakdowns

(00:02:33) Episode Intro: Cloudflare

(00:03:56) What Cloudflare Does: A Digital Postal Service

(00:06:24) How Shopify Uses Cloudflare

(00:07:29) Serving 20% of the Internet’s Traffic

(00:08:19) The Internet Before Cloudflare

(00:12:01) Cloudflare’s Founding Story

(00:14:32) Easy Onboarding, Powerful Network Effects

(00:16:05) Why Hackers Were Early Customers

(00:16:58) How Cloudflare Benefited from the Innovator’s Dilemma

(00:19:38) Why Partnering with ISPs Was a Win-Win

(00:20:44) Bigger is Better: Cloudflare’s Reinforcing Loop

(00:22:50) Product Evolution Over Time

(00:26:37) How the Internal Security Offering Works

(00:27:53) Act 3: Developing a Proprietary Software Stack

(00:33:21) Four Ways AI Impacts the Business

(00:37:04) Building Out the Enterprise Sales Function 

(00:40:06) The “Pool of Funds” Bundling Strategy

(00:43:55) How Channel Partners Drive Growth

(00:46:58) Revenue in 3 Acts

(00:48:23) Mastering the Freemium Model

(00:51:00) Margins & EBITDA

(00:52:47) Capital Allocation: Reinvestment Rules

(00:54:09) Potential New Competitors and Threats

(00:55:17) Lessons Learned From November 2025’s Outage

(00:59:17) Why Cloudflare’s Competitive Position is Strong

(01:01:19) How Canva Uses Cloudflare

(01:02:29) How Sam is Thinking About Risks

(01:04:36) 25x Sales Requires Flawless Execution

(01:07:21) 4 Lessons from Studying Cloudflare

Today we have a special episode breaking down how investors are using AI. 

This is a question I get from many of you, and while there is no shortage of content on the implications of AI, I know there's an appetite to learn more about tangible use cases, how to make sure you're getting the most out of these tools, how to think about advancements in the technology, and ensuring that you're keeping pace with the innovation curve.

So my guest today is David Plon, Founder of Portrait Analytics. Now, David and Portrait have been partners of Business Breakdowns since last year, but I specifically asked David to do this episode because, one, he is really front and center to how investors are using and applying AI. But two, and maybe more importantly, he and his team come with a background in investing. 

So while the conversation doesn’t really focus on Portrait, you’ll hear references to what he and his team are building and how they’ve shaped it for investors, you’ll very much understand when you hear David talk that he is someone who understands the pain points of an investor.

I think everyone will find something in this episode that will benefit them in their day to day, and I would love to hear the feedback. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠⁠⁠⁠⁠⁠⁠ here.⁠⁠⁠⁠⁠⁠⁠

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This episode is brought to you by ⁠⁠⁠⁠Portrait Analytics⁠⁠⁠⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before.

Sign-up for a free trial today at ⁠⁠⁠⁠⁠portraitresearch.com⁠⁠⁠⁠⁠

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Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit ⁠⁠⁠⁠⁠⁠⁠joincolossus.com/episodes⁠⁠⁠⁠⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠).

Timestamps 

(00:00:00) Welcome to Business Breakdowns

(00:04:05) Meet David Plon: Investor to Founder

(00:05:54) Pain Points in the Investment Process

(00:09:08) AI as a “Smart Filter” for News

(00:11:54) AI’s Role in the Pre-Buy Process

(00:14:34) How AI Enables Specific Quantitative Analysis

(00:17:24) Using AI for Investment Idea Generation

(00:21:42) How to Write Good Prompts for LLMs

(00:25:27) Structured vs. Creative Tasks

(00:27:47) The Value of Experimentation & Real-Time Feedback

(00:32:28) Best Practices for Deploying AI in an Institutional Setting

(00:35:57) Why Documenting Decision Making is Essential

(00:39:19) How Models Have Improved at Using Provided Context

(00:42:02) Memory in LLMs: Near-Term Limitations, Long-Term Potential

(00:46:24) Applying Agentic AI in Investment Research

Today we are breaking down Games Workshop. This episode is another examination of the business of IP. Whether it's Disney, Electronic Arts, or Nintendo, there are so many businesses built around core IP. And while Games Workshop and its Warhammer franchise may not be as familiar to our North America listeners - this episode will tell you why that may be changing very soon.

My guest is Todd Wenning, President and CIO of KNA Capital. Todd shares his own personal story uncovering Games Workshop many years ago, he gets into the fun evolution of this business which ties into the vertical integration today, and he shares what lies ahead as awareness of Warhammer’s loyal enthusiasts welcome more into their world.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠⁠⁠⁠⁠⁠⁠ here.⁠⁠⁠⁠⁠⁠⁠

—

This episode is brought to you by⁠⁠⁠⁠ ⁠Portrait Analytics⁠⁠⁠⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before.

Sign-up for a free trial today at⁠⁠⁠⁠ ⁠portraitresearch.com⁠⁠⁠⁠⁠

—

Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit⁠⁠⁠⁠⁠⁠⁠ colossus.com/episodes⁠⁠⁠⁠⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠).

Timestamps 

(00:00:00) Welcome to Business Breakdowns

(00:03:55) Introduction to Games Workshop 

(00:05:31) History of the Warhammer IP 

(00:09:14) Games Workshop's Evolution 

(00:10:59) Warhammer Retail Stores 

(00:12:37) The Numbers Behind Warhammer's Popularity 

(00:14:03) Geographic and Demographic Concentration 

(00:16:36) Competition from Other Games & Hobbies 

(00:18:49) Events and Community: Hidden Network Effects 

(00:19:48) Margins and Cash Generation 

(00:21:31) Growth Drivers & Prime Potential 

(00:24:51) Licensing Model & Tariff Volatility 

(00:26:49) Why the Business is Defensible 

(00:28:33) The Relevance Risk 

(00:31:43) Games Workshop's Unique Flat Structure 

(00:32:52) Capital Allocation & Dividend Focus 

(00:34:16) Valuing Games Workshop 

(00:35:25) Three Man Risks for the Business 

(00:38:33) Riches in Niches & Other Lessons

Today we’re breaking down Databricks, a $130B private company that helps companies collect, store, and process very large amounts of data, and then use that data to run analytics and train machine learning models.

Databricks sits in the middle of modern data systems, connecting raw data pipelines to the tools teams use to analyze information and build AI. If you’ve worked on large-scale data or AI projects, there’s a good chance Databricks was part of the stack, often operating behind the scenes.

My guest is Alan Tu, portfolio manager and analyst at WCM Investment Management, which invested in Databricks in late 2024. Alan explains what Databricks actually does for customers, why it remains one of the least understood large private software companies, and how its academic origins and founding team shaped its evolution from an early data-engineering product into a broad commercial platform.

We also discuss common misconceptions about the business, how Databricks fits into the modern AI stack, what has changed since the last time we covered the company, and how its scale, product strategy, and capital position differentiate it from competitors.

Note: This conversation was recorded on December 10, 2025, so all numbers are reflective of what was publicly available on that date.

Please enjoy this breakdown of Databricks.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠⁠⁠⁠⁠⁠⁠ here.⁠⁠⁠⁠⁠⁠⁠

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This episode is brought to you by⁠⁠⁠⁠ ⁠Portrait Analytics⁠⁠⁠⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before.

Sign-up for a free trial today at⁠⁠⁠⁠ ⁠portraitresearch.com⁠⁠⁠⁠⁠

—

Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit⁠⁠⁠⁠⁠⁠⁠ joincolossus.com/episodes⁠⁠⁠⁠⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠).

Timestamps 

(00:00:00) Welcome to Business Breakdowns

(00:02:34) Introducing Databricks and Guest Alan Tu

(00:03:22) Understanding Databricks' Core Functionality

(00:09:15) The Founding Story of Databricks

(00:23:54) Databricks' Evolution and Product Expansion

(00:30:06) Databricks vs. Snowflake: Market Competition

(00:35:36) Databricks' Strategic Vision and Market Impact

(00:38:14) The Rise of Big Data and Databricks' Core Value

(00:39:27) Understanding Databricks Through a Credit Card Fraud Use Case

(00:44:35) Databricks' Role in AI and Machine Learning

(00:51:12) The Competitive Landscape and Cloud Partnerships

(00:54:54) Financial Dynamics and Pricing Strategies

(01:09:37) The Future of Databricks: Risks and Long-Term Vision

(01:12:54) Conclusion and Final Thoughts

Today we are breaking down Amadeus, the dominant infrastructure powering global travel bookings. If you've used a travel agent or corporate booking system, you've likely interacted with Amadeus's technology—though most of what they do happens behind the scenes in airline operations, hotel inventory management, and logistics coordination.

Ben Needham, portfolio manager at Ninety One Asset Management, explains how Amadeus built its market-leading position, common investor misconceptions about the business, and the company's value proposition across the travel ecosystem. We also explore AI's potential impact on the industry and how Amadeus's balance sheet strength positions it relative to competitors. Please enjoy this breakdown of Amadeus. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page⁠⁠⁠⁠⁠⁠ here.⁠⁠⁠⁠⁠⁠

—-

This episode is brought to you by⁠⁠⁠ ⁠Portrait Analytics⁠⁠⁠⁠ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before.

Sign-up for a free trial today at⁠⁠⁠ ⁠portraitresearch.com⁠⁠⁠⁠

—

Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit⁠⁠⁠⁠⁠⁠ joincolossus.com/episodes⁠⁠⁠⁠⁠⁠.

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠).

Show Notes

(00:00:00) Introduction to Amadeus

(00:02:49) Understanding Amadeus' Business Model

(00:04:11) Amadeus' Market Position and Competitors

(00:05:35) Historical Background of Amadeus

(00:07:25) Revenue Streams and Profitability

(00:10:50) Impact of AI and Technology on Amadeus

(00:13:07) Revenue Models and Pricing Mechanics

(00:22:35) Growth Opportunities and Market Dynamics

(00:25:47) Execution and Future Prospects

(00:30:01) Financial Health and Capital Allocation

(00:31:57) Valuation and Market Perception

(00:34:21) Risks and Challenges

(00:37:13) Lessons From Amadeus