Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan tackle salary negotiation, career pivots, and why knowing your number changes everything. A recent Purdue finance grad calls in asking about building a book of business, and the hosts explain why experience matters more than credentials at 22. The show covers which cryptocurrency has the most upside, whether MSTR is finally a reasonable play now that it trades below its Bitcoin holdings, and why firing bad hires early saves more than money. A caller from Chicago asks how Lossdog will actually create worker fairness, and Tom breaks down the difference between asking for more and proving you deserve it. The hosts also dig into Nvidia's trajectory, Oracle's 6% drop on data center news, and why Larry Ellison losing half his net worth in weeks is a cautionary tale for everyone.
#stockmarket #optionstrading #salarynegotiation #career #bitcoin #knowyourworth
TIMESTAMPS
0:00 Intro
5:08 Which crypto has the most upside
9:05 Is MSTR finally a reasonable buy
13:25 How to handle firing a bad hire
16:14 Investment banking vs tech startup career paths
17:52 Which asset class to specialize in for trading firms
20:12 Market update and triple witching preview
22:22 Purdue finance grad asks about building a book of business
28:34 Nvidia outlook and when to sell calls against your position
35:08 How Lossdog creates worker fairness through data
39:47 Raising capital for a startup with no contacts
48:06 Crypto investing for beginners without margin
57:21 Larry Ellison loses half his net worth
1:01:10 Market wrap and Thursday outlook
These topics matter now because the job market heading into 2026 remains uncertain, and workers are increasingly asking whether they are underpaid. Salary negotiation skills have become essential as companies tighten budgets and layoffs continue across tech and finance. The conversation around knowing your worth is no longer optional for career advancement. Meanwhile, crypto regulation is evolving, triple witching creates short-term trading opportunities, and high-profile losses like Oracle remind investors that even billionaires make costly mistakes.
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) 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 find yours—and grow it.
👉 Join the waitlist at https://lossdog.com/
Tom Sosnoff and Scott Sheridan tackle salary negotiation, career pivots, and why knowing your number changes everything. A recent Purdue finance grad calls in asking about building a book of business, and the hosts explain why experience matters more than credentials at 22. The show covers which cryptocurrency has the most upside, whether MSTR is finally a reasonable play now that it trades below its Bitcoin holdings, and why firing bad hires early saves more than money. A caller from Chicago asks how Lossdog will actually create worker fairness, and Tom breaks down the difference between asking for more and proving you deserve it. The hosts also dig into Nvidia's trajectory, Oracle's 6% drop on data center news, and why Larry Ellison losing half his net worth in weeks is a cautionary tale for everyone.
#stockmarket #optionstrading #salarynegotiation #career #bitcoin #knowyourworth
TIMESTAMPS
0:00 Intro
5:08 Which crypto has the most upside
9:05 Is MSTR finally a reasonable buy
13:25 How to handle firing a bad hire
16:14 Investment banking vs tech startup career paths
17:52 Which asset class to specialize in for trading firms
20:12 Market update and triple witching preview
22:22 Purdue finance grad asks about building a book of business
28:34 Nvidia outlook and when to sell calls against your position
35:08 How Lossdog creates worker fairness through data
39:47 Raising capital for a startup with no contacts
48:06 Crypto investing for beginners without margin
57:21 Larry Ellison loses half his net worth
1:01:10 Market wrap and Thursday outlook
These topics matter now because the job market heading into 2026 remains uncertain, and workers are increasingly asking whether they are underpaid. Salary negotiation skills have become essential as companies tighten budgets and layoffs continue across tech and finance. The conversation around knowing your worth is no longer optional for career advancement. Meanwhile, crypto regulation is evolving, triple witching creates short-term trading opportunities, and high-profile losses like Oracle remind investors that even billionaires make costly mistakes.
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) 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 find yours—and grow it.
👉 Join the waitlist at https://lossdog.com/
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