Invest Like the Best with Patrick O'Shaughnessy

Karim Atiyeh - Building Ramp - [Invest Like the Best, EP.445]

My guest today is Karim Atiyeh [https://x.com/karimatiyeh]. Karim is the co-founder and CTO of Ramp, the fastest-growing finance automation platform in history, reaching over $1 billion in revenue in just over five years. Ramp is, of course, also our presenting sponsor, so I’m obviously very biased in how highly I think about Ramp and about Karim. But, this interview was not part of that sponsorship, I simply view Karim as one of the best operators active today. Ramp is building what Karim calls "self-driving finance"—using AI agents to automate everything from expense policy enforcement to invoice processing, eliminating the bureaucratic waste that plagues modern businesses. Karim shares his framework for moving from using AI as a productivity tool to programming AI as your actual product, with policy agents that understand context better than humans and improve continuously. Our discussion captures the relentless iteration speed and technical depth required to build generational companies in the age of AI. We explore his systematic approach to building consumer-grade experiences for business software, the psychology behind his "divinely discontent" management style, and why he believes technical founders will dominate this era because they can see possibilities others miss. Please enjoy my conversation with Karim Atiyeh. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/building-ramp/].⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:09) The Competitive Landscape and AI Advancements (00:07:27) Building Self-Driving Finance with AI (00:08:28) Policy Agents and Automation (00:12:14) Ramp's User Experience and Design Philosophy (00:23:10) Kareem's Background and Entrepreneurial Journey (00:28:06) Founding Paribus and Lessons Learned (00:41:57) The Birth of Ramp and Early Challenges (00:54:30) Nurturing Investor Relationships (00:57:10) Challenges in Fundraising (00:58:23) Customer Adoption and Product Evolution (01:01:55) Transition to SaaS Revenue Model (01:06:37) Marketing Innovations and Experiments (01:24:16) Recruiting for Spikiness and Speed (01:31:29) Future of Payments and Business Models (01:39:06) The Kindest Thing

Dan Wang - The US vs China In The 21st Century - [Invest Like the Best, EP.444]

My guest today is Dan Wang [https://x.com/danwwang]. Dan is a technology analyst and author who spent six years living in China studying its manufacturing ecosystem and tech development, best known for his new book Breakneck. Dan offers the most nuanced framework I've encountered for understanding US-China competition.  We explore a critical asymmetry: it's far harder for the US to rebuild manufacturing capacity than for China to improve scientific research, with profound implications for AI, national security, and investment returns. For investors, Dan explains the "ByteDance problem"—why exceptional Chinese companies trade at massive discounts due to Communist Party unpredictability and geopolitical risks. He argues China is a "high agency" society that executes relentlessly while America deliberates endlessly, yet also reveals the societal cost. We discuss innovation, state capacity, and investing across both superpowers. Please enjoy my conversation with Dan Wang. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/the-us-vs-china-%E2%80%A6the-21st-century/].⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:55) China's Engineering State and Social Engineering (00:12:15) US-China Competition: Innovation and Manufacturing (00:19:41) The Future of US and China: Technological and Economic Perspectives (00:25:22) Cultural and Work Ethic Comparisons (00:39:09) Investing in China: Opportunities and Risks (00:44:43) Future Equilibrium States Between US and China (00:48:32) China's High Agency and Infrastructure (00:49:58) Lawyerly Tendencies in US Society (00:53:41) Comparing US and Chinese Societal Structures (00:57:59) China's Historical Lessons and Future Prospects (01:10:39) AI and Technological Competition (01:15:30) Vertical Integration in Chinese Companies (01:26:39) The Kindest Thing

Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]

My guest today is Jesse Zhang [https://www.linkedin.com/in/thejessezhang/]. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and coding have emerged as the two clearest AI use cases for enterprises, and the key business and technical factors behind Decagon's momentum. We discuss the intense competitive dynamics of building in AI today, strategic decisions around building proprietary models, and deploying AI agents at enterprise scale. Please enjoy my conversation with Jesse Zhang. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/building-decagon/].⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:49) Building a Company in a Competitive Market (00:07:26) Personal Background and Competitive Upbringing (00:10:32) Challenges and Lessons from Previous Ventures (00:12:21) Ideation and Customer Discovery Process (00:19:31) Developing and Refining AI Customer Service Agents (00:32:26) Voice AI and Future Prospects (00:38:20) Utilizing Customer Interaction Data (00:39:59) Frameworks for Implementing AI in Business (00:41:48) Evaluating the ROI of Coding Agents (00:42:53) The Future of Company Agents (00:45:15) Brand Personality in AI Agents (00:47:48) Investor Interest in AI Companies (00:54:32) The Competitive Landscape of AI Talent (00:57:21) Building Proprietary AI Models (01:10:36) Customer Qualification and Engagement (01:17:27) The Kindest Thing

Dylan Patel - Inside the Trillion-Dollar AI Buildout - [Invest Like the Best, EP.442]

My guest today is Dylan Patel [https://www.linkedin.com/in/dylanpatelsa/]. Dylan is the founder and CEO of SemiAnalysis. At SemiAnalysis Dylan tracks the semiconductor supply chain and AI infrastructure buildout with unmatched granularity—literally watching data centers get built through satellite imagery and mapping hundreds of billions in capital flows. Our conversation explores the massive industrial buildout powering AI, from the strategic chess game between OpenAI, Nvidia, and Oracle to why we're still in the first innings of post-training and reinforcement learning. Dylan explains infrastructure realities like electrician wages doubling and companies using diesel truck engines for emergency power, while making a sobering case about US-China competition and why America needs AI to succeed. We discuss his framework for where value will accrue in the stack, why traditional SaaS economics are breaking down under AI's high cost of goods sold, and which hardware bottlenecks matter most. This is one of the most comprehensive views of the physical reality underlying the AI revolution you'll hear anywhere. Please enjoy my conversation with Dylan Patel. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠ [https://joincolossus.com/episode/inside-the-trill%E2%80%A6llar-ai-buildout/].⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.ridgelineapps.com/] to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:12) The AI Infrastructure Buildout (00:08:25) Scaling AI Models and Compute Needs (00:11:44) Reinforcement Learning and AI Training (00:14:07) The Future of AI and Compute (00:17:47) AI in Practical Applications (00:22:29) The Importance of Data and Environments in AI Training (00:29:45) Human Analogies in AI Development (00:40:34) The Challenge of Infinite Context in AI Models (00:44:08) The Bullish and Bearish Perspectives on AI (00:48:25) The Talent Wars in AI Research (00:56:54) The Power Dynamics in AI and Tech (01:13:29) The Future of AI and Its Economic Impact (01:18:55) The Gigawatt Data Center Boom (01:21:12) Supply Chain and Workforce Dynamics (01:24:23) US vs. China: AI and Power Dynamics (01:37:16) AI Startups and Innovations (01:52:44) The Changing Economics of Software (01:58:12) The Kindest Thing

Rolex: Timeless Excellence - (Invest Like the Best, CLASSICS)

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. This Business Breakdowns on Rolex is a long-time stand out. The founder and executive chairman of Hodinkee, Ben Clymer [https://www.instagram.com/benclymer?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==], was the perfect person to take us through the ins and outs of this legendary brand. For the full show notes, transcript, and links to the best content to learn more, check out the episode page ⁠here⁠ [https://www.joincolossus.com/episodes/12878745/clymer-rolex-timeless-excellence]. ----- This episode is brought to you by ⁠⁠⁠⁠⁠⁠WorkOS⁠⁠⁠⁠⁠⁠ [https://workos.com/]. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠⁠⁠⁠⁠WorkOS. [https://workos.com/] ----- Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit⁠ joincolossus.com/episodes⁠ [https://www.joincolossus.com/episodes]. Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠ [https://thepodcastconsultant.com/]). Show Notes (00:00:00) Welcome to Business Breakdowns (00:03:01) His favorite Rolex watch ever (00:04:24) What makes the Rolex Daytona such a special watch  (00:07:19) The job-to-be-done for high-end watches beyond just telling them the time (00:12:18) The strategy behind marketing luxury products: ⁠The Luxury Strategy⁠ [https://www.amazon.com/Luxury-Strategy-Break-Marketing-Brands/dp/0749464917] (00:14:34) An overview of the Rolex business (00:19:38) The history of Rolex  (00:38:45) Their genius in marketing and distribution  (00:41:55) How they make decisions and what others can learn from them (00:47:14) The financials of Rolex and other luxury watch brands (00:49:02) Most important business lessons others can learn from Rolex (00:52:54) Other luxury brands worth studying  (00:57:26) Negative lessons gleaned from Rolex