Description
Join the Lossdog wait list at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan kick off New Year's Eve by exploring unconventional investment opportunities—from Bitcoin and baseball cards to the surprising underground market for fossils (yes, NFL quarterback Joe Burrow is a collector). The episode tackles critical questions about how Lossdog's AI-powered valuation tool can empower workers even when employers have fixed salary budgets, why the restaurant industry makes career advancement so difficult, and whether the AI stock bubble is finally ready to burst in 2026. Callers share real stories about navigating pay gaps between cities, the challenges of proving your worth after years of underpayment, and why most Americans struggle to save money due to cultural spending habits rather than lack of income.
#stockmarket #investing #career #salarynegotiation #Bitcoin #optionstrading
TIMESTAMPS
0:00 Intro
4:14 Should you invest with a CTA? Tom says no
8:51 Bitcoin, baseball cards, and fossils as investments
12:13 Joe Burrow's fossil collection and alternative assets
15:19 How Lossdog helps when employers won't budge on salary
17:51 Will the AI bubble burst in 2026?
23:17 How futures contracts settle and why it's confusing
26:58 Chef struggles to get raises after 5 years
31:13 Best options trading strategy for 2026
36:34 Why Americans don't save money
41:19 What Tom would add to financial literacy education
46:23 How much capital you need for a startup
50:29 tastytrade trivia and theme song history
55:01 What is the GEX gamma exposure index?
58:54 2026 S&P 500 predictions from Tom and Scott
As 2025 closes with the S&P 500 up 17% for the year, investors and professionals alike are reassessing their strategies for building wealth in an uncertain market. With AI stock valuations at historic highs and many experts predicting a correction, understanding options trading strategies like selling upside calls and short strangles has become essential for protecting portfolios. Meanwhile, workers across industries—from executive chefs to attorneys—continue to face the challenge of geographic pay disparities and employers unwilling to recognize true professional worth, making salary negotiation skills and data-driven career tools more critical than ever for anyone preparing for a job change or performance review in 2026.
ABOUT ONE LUCKY DOG / LOSSDOG
One Lucky Dog 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) 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 kick off New Year's Eve by exploring unconventional investment opportunities—from Bitcoin and baseball cards to the surprising underground market for fossils (yes, NFL quarterback Joe Burrow is a collector). The episode tackles critical questions about how Lossdog's AI-powered valuation tool can empower workers even when employers have fixed salary budgets, why the restaurant industry makes career advancement so difficult, and whether the AI stock bubble is finally ready to burst in 2026. Callers share real stories about navigating pay gaps between cities, the challenges of proving your worth after years of underpayment, and why most Americans struggle to save money due to cultural spending habits rather than lack of income.
#stockmarket #investing #career #salarynegotiation #Bitcoin #optionstrading
TIMESTAMPS
0:00 Intro
4:14 Should you invest with a CTA? Tom says no
8:51 Bitcoin, baseball cards, and fossils as investments
12:13 Joe Burrow's fossil collection and alternative assets
15:19 How Lossdog helps when employers won't budge on salary
17:51 Will the AI bubble burst in 2026?
23:17 How futures contracts settle and why it's confusing
26:58 Chef struggles to get raises after 5 years
31:13 Best options trading strategy for 2026
36:34 Why Americans don't save money
41:19 What Tom would add to financial literacy education
46:23 How much capital you need for a startup
50:29 tastytrade trivia and theme song history
55:01 What is the GEX gamma exposure index?
58:54 2026 S&P 500 predictions from Tom and Scott
As 2025 closes with the S&P 500 up 17% for the year, investors and professionals alike are reassessing their strategies for building wealth in an uncertain market. With AI stock valuations at historic highs and many experts predicting a correction, understanding options trading strategies like selling upside calls and short strangles has become essential for protecting portfolios. Meanwhile, workers across industries—from executive chefs to attorneys—continue to face the challenge of geographic pay disparities and employers unwilling to recognize true professional worth, making salary negotiation skills and data-driven career tools more critical than ever for anyone preparing for a job change or performance review in 2026.
ABOUT ONE LUCKY DOG / LOSSDOG
One Lucky Dog 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) 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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