Description
YOUTUBE DESCRIPTION
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff, Scott Sheridan, and Sol get into one of the sharpest career debates on the show yet: is there ever a real reason to change your career path just for the sake of change? Sixty-eight percent of the audience says yes — Tom and Scott disagree on why. They also answer a new investor's two-part question: where do you actually start, and who should you be listening to? Plus, Tom breaks down why he won't trade certain stocks (the penalty box is real), walks through his bearish case on Microsoft at current levels, and the crew recaps one of the wildest NASDAQ runs in recent memory — 4,000 points in 16 days. A caller weighs in on media mergers and liquidity, and Tom shares the story of teaching his daughter to trade futures — and what happened when she picked the exact bottom to go short.
#lossdog #careerchange #stockmarket #newinvestor #optionstrading #nasdaq
TIMESTAMPS
0:00 Intro and opening banter
4:08 Show preview and question of the day
7:36 Tom's Bloomberg TV appearance story
13:06 Stocks you refuse to trade — the penalty box
15:41 Career change debate: quit just for the sake of it?
21:17 AI and new growth sectors as career opportunity
29:06 NASDAQ up 4,000 points in 16 days
31:27 The NYSE floor is now a TV studio
35:17 Career change poll: 68% say yes
36:31 Lossdog software preview and AI tools update
38:01 New investor Q: where do I start?
41:52 New investor advice: start small, stay liquid
48:33 Microsoft stock: bearish case and when to sell
51:57 Teaching a daughter to trade — and the futures disaster
58:22 CARR short squeeze recap and show close
The job market in 2026 is forcing a lot of people to rethink not just where they work, but what kind of work they want to do at all. Career pivots used to carry stigma; now with AI reshaping entire industries — from software to finance to media — sitting still in the wrong role carries its own risk. The debate on this show cuts to something most career advice skips: the difference between changing because you have to and changing because you're choosing to, and why that distinction matters more than most people realize. On the markets side, the speed of the recent NASDAQ recovery — 4,000 points in under three weeks — is a reminder that trying to time sentiment-driven moves is nearly impossible, and that the discipline of knowing what you won't trade matters just as much as knowing what you will.
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 num...
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff, Scott Sheridan, and Sol get into one of the sharpest career debates on the show yet: is there ever a real reason to change your career path just for the sake of change? Sixty-eight percent of the audience says yes — Tom and Scott disagree on why. They also answer a new investor's two-part question: where do you actually start, and who should you be listening to? Plus, Tom breaks down why he won't trade certain stocks (the penalty box is real), walks through his bearish case on Microsoft at current levels, and the crew recaps one of the wildest NASDAQ runs in recent memory — 4,000 points in 16 days. A caller weighs in on media mergers and liquidity, and Tom shares the story of teaching his daughter to trade futures — and what happened when she picked the exact bottom to go short.
#lossdog #careerchange #stockmarket #newinvestor #optionstrading #nasdaq
TIMESTAMPS
0:00 Intro and opening banter
4:08 Show preview and question of the day
7:36 Tom's Bloomberg TV appearance story
13:06 Stocks you refuse to trade — the penalty box
15:41 Career change debate: quit just for the sake of it?
21:17 AI and new growth sectors as career opportunity
29:06 NASDAQ up 4,000 points in 16 days
31:27 The NYSE floor is now a TV studio
35:17 Career change poll: 68% say yes
36:31 Lossdog software preview and AI tools update
38:01 New investor Q: where do I start?
41:52 New investor advice: start small, stay liquid
48:33 Microsoft stock: bearish case and when to sell
51:57 Teaching a daughter to trade — and the futures disaster
58:22 CARR short squeeze recap and show close
The job market in 2026 is forcing a lot of people to rethink not just where they work, but what kind of work they want to do at all. Career pivots used to carry stigma; now with AI reshaping entire industries — from software to finance to media — sitting still in the wrong role carries its own risk. The debate on this show cuts to something most career advice skips: the difference between changing because you have to and changing because you're choosing to, and why that distinction matters more than most people realize. On the markets side, the speed of the recent NASDAQ recovery — 4,000 points in under three weeks — is a reminder that trying to time sentiment-driven moves is nearly impossible, and that the discipline of knowing what you won't trade matters just as much as knowing what you will.
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 num...
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