Investing Through Volatility
In this insightful conversation, the host sits down with Scott Sheridan, CEO of TastyTrade and co-founder of the revolutionary trading platform Thinkorswim, who shares his decades of experience navigating volatile markets and building successful financial technology companies.
Scott discusses his contrarian approach to current market trends, explaining why he remains skeptical of popular investments like cryptocurrency and gold while emphasizing the importance of options trading during periods of high volatility like we’re experiencing now.
The interview explores Scott’s entrepreneurial journey from floor trader at the Chicago Board Options Exchange to creating two major brokerage firms, focusing on how he built strong company cultures and the critical importance of timing, team building, and maintaining vision while staying flexible enough to pivot when necessary.
Scott and the host delve into practical investment strategies for uncertain times, with Scott advocating for consistent market participation through dollar-cost averaging and his current preference for selling puts in quality stocks during high-volatility periods.
Key Takeaways:
- Trade small and trade often – consistent market participation with manageable risk beats trying to hit home runs, especially for those just starting their investment journey
- Focus on what you can control and maintain strong risk management – whether in trading or business, calculate your risks and never invest more than you can afford to lose
- Build businesses and hire teams based on trust and complementary skills – successful partnerships require people you’d trust with your financial future, and company culture flows from authentic leadership rather than corporate buzzwords
TRADING WISDOM FROM THE TRENCHES: SCOTT SHERIDAN ON BUILDING FINANCIAL EMPIRES
Scott Sheridan has transformed decades of market experience into extraordinary business success—without relying on speculation, trend-chasing, or conventional investment wisdom. As CEO of TastyTrade and co-founder of the revolutionary Thinkorswim platform, he shares the contrarian philosophy that has helped him navigate multiple market crashes while building two nine-figure exits that fundamentally changed how retail investors access financial markets.
With his evolution from Chicago floor trader to fintech pioneer, Scott brings a refreshingly honest, math-based approach to both trading and business building. His method emphasizes calculated risk-taking, authentic team building, and learning through direct market engagement—proving that sustainable wealth creation requires both unwavering conviction and tactical discipline to achieve remarkable results.
WHY MOST INVESTORS FAIL TO BUILD LASTING WEALTH
In this conversation, Scott reveals the biggest obstacles preventing traders from breaking through—like chasing popular investments instead of developing disciplined systems, becoming emotionally attached to positions, and failing to understand risk management fundamentals. He explains why traditional investment approaches often create anxiety rather than returns, and how shifting to a probability-based mindset leads to sustainable outcomes even during unprecedented market volatility.
THE CONSISTENCY ADVANTAGE: MASTERING MARKET PARTICIPATION
Scott breaks down his proven system for developing genuine wealth through persistent market engagement. He explains why understanding both options mathematics and personal risk tolerance is crucial to sustained success and how his approach to position sizing, volatility trading, and team culture creates organizational resilience that withstands even the most challenging market circumstances.
His methodology demonstrates why traders must be willing to “trade small, trade often,” creating systems of consistent participation and calculated risk-taking rather than emotional speculation that inevitably fails when markets face real stress and uncertainty.
KEY POINTS:
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02:34 – From floor trader to tech pioneer: How Scott transitioned from trading at the Chicago Board Options Exchange to co-founding Thinkorswim, revolutionizing online trading by creating sophisticated platforms that retail investors could actually use.
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05:35 – Why this market crash was different: Scott explains how the recent volatility was completely self-induced by political decisions, making it unlike previous crashes and creating unique opportunities for prepared traders.
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06:09 – The young investor’s advantage: Why people in their 20s and 30s need to take significant risks and stay engaged with volatile markets, since they have 40-year time horizons that virtually guarantee higher returns.
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13:01 – The psychology of trading size: Scott’s gambling wisdom about getting opponents to play for more than they’re comfortable with, and how to know immediately if you’re trading too big by your physical reaction.
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35:00 – Selling flood insurance after the flood: Scott’s current strategy of selling puts during high volatility periods, explaining how elevated option premiums create profit opportunities for patient investors.
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39:40 – Building culture through trust: How Scott creates family-like company environments by challenging employees beyond their comfort zones while promising that any mistake can be fixed with time and money.
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52:54 – The entrepreneur’s regret insurance: Scott’s passionate plea to anyone considering starting a business – the worst outcome is working for someone else again, but the regret of never trying lasts a lifetime.
The Bottom Line
If you’re tired of investment anxiety, feeling overwhelmed by market complexity, or questioning your ability to build wealth in volatile times, this episode is your blueprint for mastering both risk management and wealth creation using proven market-tested techniques.
Scott Sheridan’s strategies have helped him transform floor trading insights into fuel for continued business growth, and in this conversation, he’s laying out exactly how you can apply similar principles to your own financial and entrepreneurial journey.
Get in Touch with Scott
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