He Sold Thinkorswim for $750M, Then Built a Billion-Dollar Trading Empire. Now Tom Sosnoff Is Doing It Again

Welcome to Market Movers: Building Brands & Links with Linkifi!
Your go-to podcast for transforming your business into an unforgettable brand where branding meets SEO and link-building. I’m Chris Panteli, Co-Founder and CEO of Linkifi, and I’m joined by my co-host and Co-Founder, Nick Biggs.

In this episode we welcome Tom Sosnoff, trading legend, serial founder, and one of the key figures behind the retail options boom. Tom shares the real story behind building thinkorswim (sold to TD Ameritrade), creating tastytrade (acquired by IG Group), and why he’s now all-in on Lossdog, an AI-powered platform designed to help people understand what they’re worth and negotiate fair pay.

 

Key Talking Points

✅ A Lifelong Derivatives Builder. Tom started as a market maker at the Chicago Board Options Exchange (CBOE), then built trading platforms, brokerages, and even exchanges.
✅ “Only Two Paychecks”. Tom says he’s only ever received two paychecks in his life, tied to the acquisitions of thinkorswim and tastytrade.
✅ Exits Don’t Change the Builder. Selling a company for $750M (thinkorswim) and later a reported ~$1.1B (tastytrade) didn’t change his identity. The fun part is building.
✅ Why Tasty Happened. Tom believed finance content was painfully boring. He wanted to create fun, practical, hands-on financial media and built the first digital streaming finance network in the process.
✅ Branding With “Weird Names”. thinkorswim, tasty, Lossdog. Tom explains how offbeat names create memorability, signal disruption, and can become a brand asset even when people hate them at first.
✅ Serious Tech Behind Playful Branding. Tom’s philosophy: make the name and vibe fun, but make the underlying product world-class.
✅ Media as the Growth Engine. Tom was on the road for decades, answered emails personally, and built trust by making complex strategies understandable and usable for everyday traders.
✅ The Goodwill Model. Tom gives education away for free. The “payment” is simply using the platform. That trust loop created durable distribution.
✅ Beware the Influencer Era. Tom acknowledges there’s more noise and questionable advice online, but overall he prefers free education existing over paywalled gatekeeping.
✅ Owned Distribution vs Algorithms. Tom prefers controlling the ecosystem and keeping the message consistent, even if it limits some growth.
✅ Lossdog: A New Kind of Fintech. Lossdog is building a platform to help people know what they’re worth using massive datasets, resumes, and AI models, with a goal of improving pay fairness.
✅ AI Made It Practical. Lower costs, faster compute, and multiple AI models (not one vendor) make the “what you’re worth” engine feasible at scale.
✅ Free First, Monetize Later. Tom plans to keep the product free initially while validating how the market responds, then build a broader digital ecosystem around it.

 

Quotes from Tom Sosnoff

📢 “The fun part is building something.”
📢 “You never build what somebody else wants.”
📢 “Have some fun branding, but build a really serious kick-ass piece of technology.”
📢 “I believe in a goodwill model. I’ll tell you everything I know.”
📢 “Whatever you do, don’t pay for anything. There’s so much free education out there.”

 

Actionable Insights

🎙️ Build Trust Through Practical Education

• Teach what you actually do, not theory.
• Make complex ideas usable, not “dumbed down”.
• Consistency + competence beats polish.

🧲 Use a “Goodwill Model” to Win Distribution

• Give value away aggressively.
• Let the platform be the “ask” in return.
• Most people want to reciprocate when the value is real.

🧠 Choose a Name People Remember

• “Good” names are often boring.
• Memorable names create conversation, even if some people hate them.
• The product quality is what ultimately makes the name stick.

🤖 AI Opportunity = More Data, Lower Cost, Faster Iteration

• Multi-model stacks can keep you flexible and cost-efficient.
• AI can unlock use cases that were previously too expensive or slow to compute.
• Ship, test, and learn. Don’t over-commit to a monetization model before users prove the value.

💸 Empower People With Real Context

• “You’re underpaid” means nothing without numbers.
• Real benchmarks (role, location, experience) create leverage and clarity.
• Showing “lifetime money left on the table” can be the spark that drives action.

 

About Tom Sosnoff

Tom Sosnoff is a trading industry pioneer and serial entrepreneur. He helped reshape retail trading by co-founding thinkorswim and later building tastytrade, blending entertainment, education, and serious technology into platforms used by millions. He’s now building Lossdog, a new AI-driven platform focused on helping individuals understand compensation benchmarks and negotiate fair pay.

🌍 Join the waitlist: https://lossdog.com/
🔗 LinkedIn: https://www.linkedin.com/in/tom-sosnoff-047627293/ 

🚀 Build Your Brand with Real Links

At Linkifi, we help ambitious brands scale organic visibility through digital PR, brand storytelling, and SEO strategy. Book your FREE strategy session today:
🔗 https://book.linkifi.io/widget/bookings/pr-discovery-call

 

👋 Connect with your hosts:
👉 Chris Panteli on LinkedIn
👉 Nick Biggs on LinkedIn

 

🎧 Listen to more Market Movers episodes:
🌍 https://marketmoverspod.com