Episode Details

David Karandish, founder and CEO of Capacity, returns to Ten Thousand Miles to unpack how his company rocketed from $5M to over $100M in annual recurring revenue in just three and a half years. David breaks down the three (soon to be four) big bets that built Capacity: automating customer support with AI, raising capital outside the traditional VC path, and running a "compound startup" playbook — a strategy borrowed from Rippling's Parker Conrad — to build, partner, and acquire (19 acquisitions in 39 months) their way into an all-in-one customer experience platform. Vic and David dig into how founder-to-founder relationships and a reputation for closing deals fuel Capacity's M&A engine, how agentic coding unexpectedly solved the "impossible" problem of integrating 19 acquired companies, and why differentiated AI models — not one-size-fits-all LLMs — will define the next wave of AI economics. The conversation also covers AI's role in education, why "problem describing, selecting, and solving" should never be collapsed into one step, how Capacity thinks about competition when everyone claims to be an AI company, and what inning we're really in when it comes to enterprise AI adoption. Chapters 00:00 – Welcome Back: David Karandish Returns 01:16 – From $5M to $100M ARR: The Three Big Bets 05:05 – The Compound Startup Playbook (Parker Conrad's Framework) 12:23 – How Capacity Finds, Diligences, and Closes Acquisitions 20:15 – Agentic Coding: The Hidden Unlock for M&A Integration 25:42 – Token Costs, Model Economics, and the Future of Compute 42:20 – AI in Education, Work, and the "Agents Everywhere" Bet 52:33 – Competing on the Oval: Problem-Solving Framework and What's Next Guest: David Karandish, Founder & CEO of Capacity, previously founder of Answers.com