Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan kick off the show with a special announcement: Slash recorded an original theme song for Lossdog. From there, the conversation covers zero DTE options strategy when VIX is low, why every successful business pivots, the real sacrifices of building a startup, and how to raise capital when self-promotion isn't your strength. Callers ask about using competing job offers to negotiate salary, the PDT rule timeline, and networking strategies for veterans transitioning to civilian careers.
#stockmarket #optionstrading #entrepreneurship #salarynegotiation #startup #careeradvice
TIMESTAMPS
0:00 Intro
1:54 Slash wrote an original song for Lossdog
3:58 NASDAQ looking weak, market overview
8:40 Zero DTE options: when to trade based on VIX 1D
11:55 Why every business has to pivot
15:10 Don't overthink it, pivot
16:54 The personal and family sacrifices of building a startup
21:38 How much cash to keep as a safety net for a new business
23:41 Raising capital when self-promotion isn't your strength
31:41 Caller: Using a competing offer to negotiate salary
37:52 Caller: tastytrade “Rising Star” shares networking strategies for veterans (Honor Foundation).
41:58 VIX under 15: how much capital to allocate to short premium
45:11 The value of in-person meetings vs Zoom
47:56 Caller: Hourly options, PDT rule update, and tokenized clearing
55:51 Market check and January expiration outlook
58:45 2026 Predictions and college football picks: Ole Miss vs Miami
The job market in 2026 remains competitive, and knowing your professional worth has never been more important. Whether you're negotiating a raise, considering a career change, or transitioning from military service to civilian work, having real data on your market value changes everything. This episode also breaks down why low volatility environments require different trading strategies and why every entrepreneur should expect to pivot multiple times before finding product-market fit.
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 kick off the show with a special announcement: Slash recorded an original theme song for Lossdog. From there, the conversation covers zero DTE options strategy when VIX is low, why every successful business pivots, the real sacrifices of building a startup, and how to raise capital when self-promotion isn't your strength. Callers ask about using competing job offers to negotiate salary, the PDT rule timeline, and networking strategies for veterans transitioning to civilian careers.
#stockmarket #optionstrading #entrepreneurship #salarynegotiation #startup #careeradvice
TIMESTAMPS
0:00 Intro
1:54 Slash wrote an original song for Lossdog
3:58 NASDAQ looking weak, market overview
8:40 Zero DTE options: when to trade based on VIX 1D
11:55 Why every business has to pivot
15:10 Don't overthink it, pivot
16:54 The personal and family sacrifices of building a startup
21:38 How much cash to keep as a safety net for a new business
23:41 Raising capital when self-promotion isn't your strength
31:41 Caller: Using a competing offer to negotiate salary
37:52 Caller: tastytrade “Rising Star” shares networking strategies for veterans (Honor Foundation).
41:58 VIX under 15: how much capital to allocate to short premium
45:11 The value of in-person meetings vs Zoom
47:56 Caller: Hourly options, PDT rule update, and tokenized clearing
55:51 Market check and January expiration outlook
58:45 2026 Predictions and college football picks: Ole Miss vs Miami
The job market in 2026 remains competitive, and knowing your professional worth has never been more important. Whether you're negotiating a raise, considering a career change, or transitioning from military service to civilian work, having real data on your market value changes everything. This episode also breaks down why low volatility environments require different trading strategies and why every entrepreneur should expect to pivot multiple times before finding product-market fit.
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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