Entrepreneur Perspectives

Tastytrade: How a Trading & Media Empire Was Built by Giving Everything Away | Scott Sheridan CEO — EP189

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Scott Sheridan is the CEO of Tastytrade, a trading platform and brokerage he co-founded with longtime partner Tom Sosnoff. Together with their amazing team, they’ve built a trading and media empire using a counterintuitive strategy: giving away their best content for free.

In this episode, Scott explains how their “goodwill model” works — from free education on Tastylive to transparent customer service — and why betting everything on authentic content paid off. You’ll also hear his thoughts on broken systems, the future of education, and what separates genuine content from noise.

This isn’t Scott’s first rodeo. He and Tom previously built Thinkorswim — you’ve probably heard of it — which was acquired by TD Ameritrade (now part of Charles Schwab). Today, Tastytrade serves thousands of active traders while Tastylive produces 10 hours of live market content daily, has 447K+ and growing subscribers on YouTube, and their videos regularly get hundreds of thousands of views! Tastytrade is the brokerage platform where viewers can actually execute trades — turning educational content into trading customers.

Inside This Episode with Tastytrade CEO, Scott Sheridan:
  • Why “that’s the way it is” is a terrible excuse
  • The real reason customer service is falling apart
  • How AI can remove gatekeepers and speed things up
  • Why insurance and financial products are too complicated
  • How Scott thinks about risk-taking in your 20s
  • College, cheating, and what education is (and isn’t) worth
  • Autonomous vehicles, safety, and the future of driving
  • Why Scott has never been on social media
  • What makes Tastytrade content actually trustworthy
  • The culture loss in remote work — and what to do about it
    • Chapters:
    • 00:34 – Building Tastytrade through free, educational content
    • 04:51 – Using goodwill as a business strategy
    • 08:06 – Why most firms can’t copy Tastytrade’s model
    • 12:25 – Real customer service vs. being treated like a number
    • 18:06 – What’s broken in big industries
    • 20:17 – “Change the industry” as a mindset
    • 26:15 – Encouraging young people to take risks
    • 28:40 – College isn’t for everyone (and that’s okay)
    • 32:27 – How AI will reshape learning — and teaching
    • 34:17 – Riding in a Waymo and the case for autonomous driving
    • 40:11 – Social media, screen time, and mental health
    • 44:37 – Creating honest content in a hype-driven world
    • 46:55 – Why they brought employees back to the office
    • 52:06 – From Thinkorswim to Tastytrade
    • 54:09 – Who Tastytrade is really for (and how it’s evolving)
      • Scott Sheridan & Tastytrade:
      • Tastytrade: website
      • Tastylive: YouTube Channel

        • Related Episodes:

        • Ankit Somani | Ex-Google, Rare-Earth-Free Motors, $20M Seed, Rethinking College
        • Dr. Shalabh Gupta | Biotech, AI, and Making Dialysis Optional
        • Remote Work in Today’s Financial Advisory Industry | Joe Cantanucci

          • Entrepreneur Perspectives is produced by QuietLoud Studios — a modern media network and a KazSource brand.

          Get in touch with Eric Kasimov:

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          Credits:

          Music by Jess & Ricky: SoundCloud

          The post Tastytrade: How a Trading & Media Empire Was Built by Giving Everything Away | Scott Sheridan CEO — EP189 appeared first on KazSource.

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