Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan break down how to build a core-satellite options portfolio, share wild stories from their early trading floor days including a trader who lost $4 million in a single afternoon, and explain why selling naked puts beats put spreads almost every time. They also get into the 401k vs Roth debate, overnight futures orders, and why disciplined smart people sometimes fail at trading while high school dropouts crush it. Plus, a heated debate continues on whether politicians should be allowed to trade.
#lossdog #optionstrading #nakedputs #401k #tradingpsychology #futurestrading
TIMESTAMPS
0:00 Intro
0:19 Building a core-satellite options portfolio
2:39 Why lowering your cost basis is the real goal
4:44 How much trading capital do you need to start trading
6:22 Tom's first trading stake and losing it in two weeks
7:56 The stranger who lent Tom $100K in 1980s Chicago
12:35 Overnight resting futures orders: open vs close
15:34 How to convert a leveraged ETF into a futures position
20:55 Widening spreads and using more buying power
22:23 Caller Loki asks about 401k contributions and Roth vs traditional
26:33 Should you stop trading after hitting your annual goal
28:49 Put and call skew across stocks, ETFs, and indices
30:50 Caller Charlie asks about naked puts vs spreads
32:50 Trading with 70-80% of your net worth
37:18 Caller Steve reignites the politician trading debate
46:15 VIX and S&P correlation explained
52:17 Why smart, disciplined people fail at trading
59:24 Caller from Utah Crypto allocation: how much is too much
1:01:57 Market talk and earnings plays
The conversation about politician trading restrictions continues to divide audiences, with 72% of viewers favoring more restrictions while Tom argues that allowing politicians to trade keeps them financially literate and connected to market structure. Meanwhile, the hosts share hard-earned wisdom about trading psychology: the difference between hearing a closing order fill at 3 AM versus an opening order is the difference between sleeping soundly and staring at the ceiling. With the S&P flirting with 7000 and volatility compression finally hitting precious metals, the current market environment rewards traders who understand position sizing and know when to stay in the game.
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 how to build a core-satellite options portfolio, share wild stories from their early trading floor days including a trader who lost $4 million in a single afternoon, and explain why selling naked puts beats put spreads almost every time. They also get into the 401k vs Roth debate, overnight futures orders, and why disciplined smart people sometimes fail at trading while high school dropouts crush it. Plus, a heated debate continues on whether politicians should be allowed to trade.
#lossdog #optionstrading #nakedputs #401k #tradingpsychology #futurestrading
TIMESTAMPS
0:00 Intro
0:19 Building a core-satellite options portfolio
2:39 Why lowering your cost basis is the real goal
4:44 How much trading capital do you need to start trading
6:22 Tom's first trading stake and losing it in two weeks
7:56 The stranger who lent Tom $100K in 1980s Chicago
12:35 Overnight resting futures orders: open vs close
15:34 How to convert a leveraged ETF into a futures position
20:55 Widening spreads and using more buying power
22:23 Caller Loki asks about 401k contributions and Roth vs traditional
26:33 Should you stop trading after hitting your annual goal
28:49 Put and call skew across stocks, ETFs, and indices
30:50 Caller Charlie asks about naked puts vs spreads
32:50 Trading with 70-80% of your net worth
37:18 Caller Steve reignites the politician trading debate
46:15 VIX and S&P correlation explained
52:17 Why smart, disciplined people fail at trading
59:24 Caller from Utah Crypto allocation: how much is too much
1:01:57 Market talk and earnings plays
The conversation about politician trading restrictions continues to divide audiences, with 72% of viewers favoring more restrictions while Tom argues that allowing politicians to trade keeps them financially literate and connected to market structure. Meanwhile, the hosts share hard-earned wisdom about trading psychology: the difference between hearing a closing order fill at 3 AM versus an opening order is the difference between sleeping soundly and staring at the ceiling. With the S&P flirting with 7000 and volatility compression finally hitting precious metals, the current market environment rewards traders who understand position sizing and know when to stay in the game.
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/
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