Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff breaks down his overnight silver trading strategy while Scott Sheridan explains why strangles are easier to manage than iron condors for options traders. The crew tackles a father managing his daughter's account with 21-28% annual returns, debates whether engineers should ask employers for part-time status to pursue side projects, and gets brutally honest about why most bosses would say no. Plus, a deep cut on transfer pricing careers, the flawed home loan system that punishes 1099 workers, and why the Bears-Packers rivalry is the best thing happening in sports right now.
#lossdog #optionstrading #careeradvice #salarynegotiation #stockmarket #financialfreedom
TIMESTAMPS
0:00 Intro
3:50 Football weekend food plans and bratwurst debate
8:02 Tom's overnight silver trading breakdown
10:01 When Harry Met Sally and old movies R.I.P. Bob Reiner
12:57 Managing daughter's options account with strangles vs iron condors
15:43 Stay focused: advice from a board meeting
17:52 Saks Global bankruptcy and the future of retail
20:05 Gen Z bringing back mall culture and cigarettes
21:31 Are extended options trading hours coming soon
23:27 What makes a 38-year business partnership work
25:54 Engineer wants part-time status for a side project
29:34 MBA right after undergrad or get work experience first?
32:41 Michael Jordan vs Tom Brady: toughest competitor
36:29 Transfer pricing careers explained
42:15 When would you actually buy options instead of sell?
45:08 How to validate a business idea when starting from scratch
50:32 Poll results and Bears-Packers rivalry is the best thing in sports
54:50 Breaking the W-2 culture and the flawed home loan system
58:45 Market Talk
The home lending system in America is built around W-2 employment as a proxy for stability, even though a salaried employee could lose their job the day after closing on a house. This creates real friction for entrepreneurs, freelancers, and 1099 workers who often have more financial discipline but less paperwork to prove it. The conversation also touches on why banks fail—spoiler: it's rarely bad home loans and almost always mismanaged risk elsewhere in their portfolios.
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 breaks down his overnight silver trading strategy while Scott Sheridan explains why strangles are easier to manage than iron condors for options traders. The crew tackles a father managing his daughter's account with 21-28% annual returns, debates whether engineers should ask employers for part-time status to pursue side projects, and gets brutally honest about why most bosses would say no. Plus, a deep cut on transfer pricing careers, the flawed home loan system that punishes 1099 workers, and why the Bears-Packers rivalry is the best thing happening in sports right now.
#lossdog #optionstrading #careeradvice #salarynegotiation #stockmarket #financialfreedom
TIMESTAMPS
0:00 Intro
3:50 Football weekend food plans and bratwurst debate
8:02 Tom's overnight silver trading breakdown
10:01 When Harry Met Sally and old movies R.I.P. Bob Reiner
12:57 Managing daughter's options account with strangles vs iron condors
15:43 Stay focused: advice from a board meeting
17:52 Saks Global bankruptcy and the future of retail
20:05 Gen Z bringing back mall culture and cigarettes
21:31 Are extended options trading hours coming soon
23:27 What makes a 38-year business partnership work
25:54 Engineer wants part-time status for a side project
29:34 MBA right after undergrad or get work experience first?
32:41 Michael Jordan vs Tom Brady: toughest competitor
36:29 Transfer pricing careers explained
42:15 When would you actually buy options instead of sell?
45:08 How to validate a business idea when starting from scratch
50:32 Poll results and Bears-Packers rivalry is the best thing in sports
54:50 Breaking the W-2 culture and the flawed home loan system
58:45 Market Talk
The home lending system in America is built around W-2 employment as a proxy for stability, even though a salaried employee could lose their job the day after closing on a house. This creates real friction for entrepreneurs, freelancers, and 1099 workers who often have more financial discipline but less paperwork to prove it. The conversation also touches on why banks fail—spoiler: it's rarely bad home loans and almost always mismanaged risk elsewhere in their portfolios.
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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