Description
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Tom Sosnoff and Scott Sheridan get into the real strategy behind surviving a market crash—spoiler: it's not about timing it, it's about size. They also break down the crypto wash sale loophole the IRS hasn't closed, whether trade journaling actually matters, and Tom's highest conviction trade right now heading into Micron earnings. The OEX pit gets some love too, with wild stories from the floor. Plus: should workers have a seat on corporate boards, how to measure organic startup growth, and a live market rundown with VIX levels, crude oil, gold, silver, and Bitcoin catching a serious bid.
#lossdog #optionstrading #stockmarket #investing #financialfreedom #tradingstrategy
TIMESTAMPS
0:00 Intro
0:10 How to survive the next market crash
2:23 Is 2026 the end of buy the dip?
3:35 IONQ and SOUN: quantum computing stocks
6:35 OpenAI at $850B—is the AI hype real?
7:20 What metric founders ignore that actually signals survival
10:03 Crypto wash sale rule explained
11:30 Should you journal your trades?
14:16 SPX vs XSP iron condor—what's the real difference?
16:37 What does trading small actually mean?
19:12 The problem with trading small: can you make real money?
20:30 Selling options vs. buying options—the insurance analogy
25:41 Better trader: Tom with or without beret
26:13 Should workers have board representation?
28:22 Best trades and craziest moments from the OEX pit
30:59 Books and resources for learning the market maker's playbook
32:22 Advice for your 35-year-old self
33:44 Midterm election year drawdowns and how to position
37:36 One account or three? The $150K split question
40:59 Tom's highest conviction trade to fade
43:55 How to measure organic startup growth
46:02 Explanation of 'bought the put book at a cabinet'
47:37 High Oil and Inflation - interest rates
50:03 Finding your trading edge and entry point
52:57 Adjusting trading style after leaving the floor
56:10 Market Talk: Micron, Bitcoin, gold, silver, VIX, bonds
With the S&P sitting on historically elevated valuations and the average midterm election year drawdown coming in near 19%, 2026 is shaping up to be a year where position sizing and portfolio construction matter more than stock-picking. The crypto wash sale loophole—still active because the IRS classifies crypto as property, not a security—gives active traders a real tax tool that doesn't exist anywhere else in the market. Meanwhile, Micron earnings, triple witching, and a volatile week in crude oil and gold are all reminders that volatility doesn't announce itself—it just shows up. The conversation around whether startup founders are optimizing for the wrong metrics (EBITDA over growth) mirrors a broader tension in the market: are investors pricing in fundamentals or just narrative? These are the questions that separate people who build durable wealth from those who get caught leaning the wrong way.
ABOUT ONE LUCKY DOG LIVE! / LOSSDOG
One Lucky Dog LIVE! is your daily wake-up call for career and financial clarity—streaming live Monday through Thursday, 10-11am ET. Hosts Tom Sosnoff and Scott Sheridan (the founders behind thinkorswim and tastytrade) along with co-host Sol bring decades of experience democratizing finance, now turning their attention to something just as broken: how we understand our professional worth.
Lossdog is the platform they're building to fix it. It's AI-powered software that doesn't just guess what you should earn—it calculates your real market value and shows you exactly how to increase it. No more vague salary ranges. No more wonde...
Tom Sosnoff and Scott Sheridan get into the real strategy behind surviving a market crash—spoiler: it's not about timing it, it's about size. They also break down the crypto wash sale loophole the IRS hasn't closed, whether trade journaling actually matters, and Tom's highest conviction trade right now heading into Micron earnings. The OEX pit gets some love too, with wild stories from the floor. Plus: should workers have a seat on corporate boards, how to measure organic startup growth, and a live market rundown with VIX levels, crude oil, gold, silver, and Bitcoin catching a serious bid.
#lossdog #optionstrading #stockmarket #investing #financialfreedom #tradingstrategy
TIMESTAMPS
0:00 Intro
0:10 How to survive the next market crash
2:23 Is 2026 the end of buy the dip?
3:35 IONQ and SOUN: quantum computing stocks
6:35 OpenAI at $850B—is the AI hype real?
7:20 What metric founders ignore that actually signals survival
10:03 Crypto wash sale rule explained
11:30 Should you journal your trades?
14:16 SPX vs XSP iron condor—what's the real difference?
16:37 What does trading small actually mean?
19:12 The problem with trading small: can you make real money?
20:30 Selling options vs. buying options—the insurance analogy
25:41 Better trader: Tom with or without beret
26:13 Should workers have board representation?
28:22 Best trades and craziest moments from the OEX pit
30:59 Books and resources for learning the market maker's playbook
32:22 Advice for your 35-year-old self
33:44 Midterm election year drawdowns and how to position
37:36 One account or three? The $150K split question
40:59 Tom's highest conviction trade to fade
43:55 How to measure organic startup growth
46:02 Explanation of 'bought the put book at a cabinet'
47:37 High Oil and Inflation - interest rates
50:03 Finding your trading edge and entry point
52:57 Adjusting trading style after leaving the floor
56:10 Market Talk: Micron, Bitcoin, gold, silver, VIX, bonds
With the S&P sitting on historically elevated valuations and the average midterm election year drawdown coming in near 19%, 2026 is shaping up to be a year where position sizing and portfolio construction matter more than stock-picking. The crypto wash sale loophole—still active because the IRS classifies crypto as property, not a security—gives active traders a real tax tool that doesn't exist anywhere else in the market. Meanwhile, Micron earnings, triple witching, and a volatile week in crude oil and gold are all reminders that volatility doesn't announce itself—it just shows up. The conversation around whether startup founders are optimizing for the wrong metrics (EBITDA over growth) mirrors a broader tension in the market: are investors pricing in fundamentals or just narrative? These are the questions that separate people who build durable wealth from those who get caught leaning the wrong way.
ABOUT ONE LUCKY DOG LIVE! / LOSSDOG
One Lucky Dog LIVE! is your daily wake-up call for career and financial clarity—streaming live Monday through Thursday, 10-11am ET. Hosts Tom Sosnoff and Scott Sheridan (the founders behind thinkorswim and tastytrade) along with co-host Sol bring decades of experience democratizing finance, now turning their attention to something just as broken: how we understand our professional worth.
Lossdog is the platform they're building to fix it. It's AI-powered software that doesn't just guess what you should earn—it calculates your real market value and shows you exactly how to increase it. No more vague salary ranges. No more wonde...
