Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan break down the best strategies for shorting the market when you're leaning bearish, from naked calls in SPY to micro futures in the ES and NQ. They get into why long put verticals don't give you the "oomph" you're looking for on big down moves, how to manage accounts once they exceed $10 million (spoiler: it's nearly impossible), and why yesterday's 2% selloff isn't the buying opportunity everyone on TV thinks it is. Plus a caller asks if her money is safe at tastytrade after Tom and Scott left, and a mother-daughter duo calls in back to back.
#lossdog #optionstrading #stockmarket #shortingthemarket #tradingstrategies #spyfutures
TIMESTAMPS
0:00 Intro
0:18 Best strategies to short the market
3:37 Why long put verticals lack oomph
3:41 Short skewed strangles warning
6:00 Netflix earnings trade breakdown
6:59 VIX cash vs futures spread
7:46 Private investment philosophy
10:23 Account size limits for active trading
14:33 Nvidia market cap vs Germany's stock market
15:50 The 100-step binomial strategy explained
17:55 The 390 order rule for professional traders
26:26 Bitcoin and NASDAQ correlation as pairs trade
28:35 Startup funding and presenting metrics to investors
32:48 Caller Beth asks about account safety in brokerage firms
38:20 Adapting options strategies in low volatility
44:45 Career pivot advice for a 51-year-old teacher
49:20 Bitcoin allocation and portfolio percentage
53:29 Caller Shay asks how to start from scratch
57:02 Market talk and why Tom is short
The 2026 market rally has pushed the S&P 500 to within 2% of all-time highs, compressing implied volatility and shrinking the edge for premium sellers. For traders looking to position short, the challenge isn't just picking direction—it's maintaining delta exposure when gamma works against you on big moves. Meanwhile, the Bitcoin volatility collapse to mid-40s IV levels now puts it in the same risk bucket as Nvidia and Tesla, fundamentally changing its role as a portfolio diversifier.
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 wondering if you're being underpaid. Just clarity, backed by data.
The show is the conversation. The platform is the tool. Together, they're designed to help you stop leaving money on the table and start building the career you actually deserve.
📺 Watch live: Mon-Thu 10-11am ET
📞 Call in: 989-LOSSDOG
📧 oneluckydog@lossdog.com
🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog
Everyone has a number. Lossdog helps you know your number, and grow your number.
👉 Join the waitlist at https://lossdog.com/
Tom Sosnoff and Scott Sheridan break down the best strategies for shorting the market when you're leaning bearish, from naked calls in SPY to micro futures in the ES and NQ. They get into why long put verticals don't give you the "oomph" you're looking for on big down moves, how to manage accounts once they exceed $10 million (spoiler: it's nearly impossible), and why yesterday's 2% selloff isn't the buying opportunity everyone on TV thinks it is. Plus a caller asks if her money is safe at tastytrade after Tom and Scott left, and a mother-daughter duo calls in back to back.
#lossdog #optionstrading #stockmarket #shortingthemarket #tradingstrategies #spyfutures
TIMESTAMPS
0:00 Intro
0:18 Best strategies to short the market
3:37 Why long put verticals lack oomph
3:41 Short skewed strangles warning
6:00 Netflix earnings trade breakdown
6:59 VIX cash vs futures spread
7:46 Private investment philosophy
10:23 Account size limits for active trading
14:33 Nvidia market cap vs Germany's stock market
15:50 The 100-step binomial strategy explained
17:55 The 390 order rule for professional traders
26:26 Bitcoin and NASDAQ correlation as pairs trade
28:35 Startup funding and presenting metrics to investors
32:48 Caller Beth asks about account safety in brokerage firms
38:20 Adapting options strategies in low volatility
44:45 Career pivot advice for a 51-year-old teacher
49:20 Bitcoin allocation and portfolio percentage
53:29 Caller Shay asks how to start from scratch
57:02 Market talk and why Tom is short
The 2026 market rally has pushed the S&P 500 to within 2% of all-time highs, compressing implied volatility and shrinking the edge for premium sellers. For traders looking to position short, the challenge isn't just picking direction—it's maintaining delta exposure when gamma works against you on big moves. Meanwhile, the Bitcoin volatility collapse to mid-40s IV levels now puts it in the same risk bucket as Nvidia and Tesla, fundamentally changing its role as a portfolio diversifier.
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 wondering if you're being underpaid. Just clarity, backed by data.
The show is the conversation. The platform is the tool. Together, they're designed to help you stop leaving money on the table and start building the career you actually deserve.
📺 Watch live: Mon-Thu 10-11am ET
📞 Call in: 989-LOSSDOG
📧 oneluckydog@lossdog.com
🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog
Everyone has a number. Lossdog helps you know your number, and grow your number.
👉 Join the waitlist at https://lossdog.com/
Hosted on Ausha. See ausha.co/privacy-policy for more information.
