Tyler Jackowski: From Teaching to Content Creation

In this episode of First Round’s On Me, we sit down with Tyler Jackowski — better known online as Fishing for Clout — a Boston-bred teacher turned viral storyteller who’s built one of the most positive corners of the internet.Tyler opens up about his journey from classroom chaos to content creation, what teaching taught him about empathy, and how he’s redefining what it means to connect online. We talk about the Boston vs LA mindset, the illusion of influence, education reform, and his mission to give teachers the recognition (and paychecks) they deserve through America’s Heroes.This one’s equal parts hilarious and heartfelt — from kids roasting their teacher on Zoom to tackling the future of connection in an AI-driven world.💬 In the comments: Which teacher had the biggest impact on your life?00:00 – Tyler Jackowski joins the show00:45 – Boston vs LA accents & social culture03:15 – Life as a teacher turned creator05:20 – Going viral with student stories07:05 – Kids, humor & classroom chaos09:45 – From teaching to TikTok fame12:00 – Moving from Boston → LA → NY14:10 – The LA social scene & authenticity17:00 – Building real connections online19:20 – Creating community through content22:00 – Teaching during Covid24:00 – How Fishing for Clout began26:30 – Mental health, empathy & influence30:00 – The birth of America’s Heroes33:10 – Fixing education through opportunity36:00 – The power of good teachers38:00 – Incentives that change classrooms40:20 – Rewarding teachers globally43:00 – Tech, AI & human connection47:00 – The meaning of imperfection51:00 – Outro & future collabs