HoldCo Bros are back! In this episode, Nik shares what he learned from 30+ conversations with entrepreneurs using AI in their businesses—what tools they’re using, what’s actually working, and some surprising patterns that came up. We also talk about how he built a full workflow using Google CoLab and OpenAI to analyze all the data.
I also share my experiment with a real-world billboard ad for the podcast, how I’m testing taglines with Facebook ads, and different ways I’m tracking the results. We even get into some fun ideas around using AI for things like relationship advice and business mediation.
00:00 Highlights 00:33 ChatGPT's Bias and Trustworthiness vs. Google 02:58 Seeking Unbiased Feedback from AI (and its Challenges) 07:38 AI for Business Mediation and Conflict Resolution 10:04 Most Popular LLMs and Their Use Cases (ChatGPT, Claude, Perplexity) 12:33 Claude’s Advanced Project Structure & Writing Strengths 15:02 Cursor vs. Replit: Coding Tools and Usability vs. Functionality 17:26 AI Tools Summary: Use Cases and Strengths by Model 19:52 Cleaning and Analyzing Podcast Transcripts Using AI & Google Colab 22:20 Automating Insights: Creating Lead Magnets and Quizzes with AI 24:40 The Importance of Data for Personal AI Assistants 27:07 Billboard A/B Testing Strategy for Podcast Growth 29:27 The Power of “Best” in Marketing and Ratings Psychology 31:54 Measuring Billboard Effectiveness via Download Geography 34:19 Saturating Small Cities with Ads: A Contagion-Style Growth Idea