Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff's ears are ringing!
Scott Sheridan, Sol, and guest co-host Jeff Joseph (Chief Strategist at Lossdog, formerly of tastytrade's Luckbox) took the opportunity to do something they can't normally do: debate Tom's most controversial positions to his face—and then without it. Three hot takes on the table: insider trading should be legal, work-life balance is a fantasy, and geopolitical events are completely untradeable. Scott, Sol, and Jeff share where they actually agree, where they push back hard, and then Tom calls in live from New York to defend himself.
#lossdog #insidertrading #worklifebalance #stockmarket #optionstrading #career
TIMESTAMPS
0:00 Today's format: debating Tom's 3 hot takes
3:17 Should insider trading be legal?
9:20 Warren Buffett, Reg FD, and information edge
10:24 Pelosi's 838% returns and the Microsoft trade
16:00 Tom makes an 'appearance'
20:26 Work-life balance debate: fantasy or real need?
27:46 Startups, all-in culture, and equity as incentive
29:14 Caller Mike: PDT rule change and Robinhood's rally
32:30 Quick look at the market
34:45 Are geopolitical events tradeable?
38:37 Apple, TSMC, Taiwan
40:54 Lockheed as data points
43:15 Tom calls in live and weighs in on all three
45:50 Caller Simon: startup equity pools and option strategy
52:50 thinkorswim's option pool mistake—what they learned
54:50 Tom's real hot take: nobody knows anything
56:34 Market Talk: and the Charlie Trotter dinner story
The insider trading debate has new stakes in 2026, with congressional disclosure rules still allowing a 45-day filing window and retail investors increasingly aware of how information asymmetry shapes outcomes. Work-life balance sits at a cultural crossroads—hustle culture has receded, but early-stage startups still demand full commitment to survive, and the question of how to compensate for that sacrifice is real and unresolved. The geopolitical tradeable debate connects directly to how AI, chipmakers, and Taiwan exposure are pricing into the market right now, with concentration risk in a handful of mega-cap names a genuine structural concern. These aren't abstract ideas—they're the exact frameworks anyone thinking seriously about career, compensation, and markets needs to work through.
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's ears are ringing!
Scott Sheridan, Sol, and guest co-host Jeff Joseph (Chief Strategist at Lossdog, formerly of tastytrade's Luckbox) took the opportunity to do something they can't normally do: debate Tom's most controversial positions to his face—and then without it. Three hot takes on the table: insider trading should be legal, work-life balance is a fantasy, and geopolitical events are completely untradeable. Scott, Sol, and Jeff share where they actually agree, where they push back hard, and then Tom calls in live from New York to defend himself.
#lossdog #insidertrading #worklifebalance #stockmarket #optionstrading #career
TIMESTAMPS
0:00 Today's format: debating Tom's 3 hot takes
3:17 Should insider trading be legal?
9:20 Warren Buffett, Reg FD, and information edge
10:24 Pelosi's 838% returns and the Microsoft trade
16:00 Tom makes an 'appearance'
20:26 Work-life balance debate: fantasy or real need?
27:46 Startups, all-in culture, and equity as incentive
29:14 Caller Mike: PDT rule change and Robinhood's rally
32:30 Quick look at the market
34:45 Are geopolitical events tradeable?
38:37 Apple, TSMC, Taiwan
40:54 Lockheed as data points
43:15 Tom calls in live and weighs in on all three
45:50 Caller Simon: startup equity pools and option strategy
52:50 thinkorswim's option pool mistake—what they learned
54:50 Tom's real hot take: nobody knows anything
56:34 Market Talk: and the Charlie Trotter dinner story
The insider trading debate has new stakes in 2026, with congressional disclosure rules still allowing a 45-day filing window and retail investors increasingly aware of how information asymmetry shapes outcomes. Work-life balance sits at a cultural crossroads—hustle culture has receded, but early-stage startups still demand full commitment to survive, and the question of how to compensate for that sacrifice is real and unresolved. The geopolitical tradeable debate connects directly to how AI, chipmakers, and Taiwan exposure are pricing into the market right now, with concentration risk in a handful of mega-cap names a genuine structural concern. These aren't abstract ideas—they're the exact frameworks anyone thinking seriously about career, compensation, and markets needs to work through.
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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