Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
It's Tax Day, the PDT rule is officially dead in 45 days, and Tom Sosnoff and Scott Sheridan have a lot to say about all of it. Tom shares what he told a room full of startup CEOs the night before about why professional networks are worth multiples — not percentages — of your net worth, and why most people have no idea what hidden opportunity they're leaving on the table. Then Scott breaks down outlier risk in plain terms: why trade size is the only real answer, why stress testing has limits, and what GameStop, Zoom, and Long-Term Capital Management all have in common. Sol keeps it real throughout.
#lossdog #optionstrading #careerdevelopment #networking #stockmarket #financialfreedom
TIMESTAMPS
0:00 Intro and hockey in Ovechkin's hallway
6:49 SEC signs off on PDT rule change
11:39 Tax Day check-in and show topics preview
12:50 Is any financial news source actually worth watching?
16:58 Building a professional network: cultivating relationships over a lifetime
20:47 Be a giver first: the goodwill model
23:22 Where to build connections and why remote work hurts
25:43 Be able to articulate your value clearly and quickly
30:34 Hidden opportunity only networks can unlock
32:59 Market update: S&Ps, NASDAQ near highs, short setups
38:43 Lossdog platform update: 2,000 new users and agentic AI
40:42 Outlier risk: why trade size is the only real answer
43:22 Fooled by randomness and model failure explained
47:46 Asymmetric loss
48:33 The insurance company analogy
49:17 Can you actually stress test for outlier risk?
52:35 Are outlier moves mean reverting?
56:24 Market Talk
Professional networks and outlier risk don't usually share a conversation, but they're connected by the same idea: most of what matters is happening off the public feed. The hidden job market, the private deal flow, the black swan move that stress tests can't predict — these are all features of a system where information travels through relationships, not headlines. With the PDT rule getting scrapped after 25 years, retail traders are getting a genuine shot at more active participation just as volatility starts to settle back down from the April spike. And with AI stress testing tools becoming accessible to everyday investors, the gap between institutional and retail risk management is narrowing faster than most financial media is willing to admit.
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://loss...
It's Tax Day, the PDT rule is officially dead in 45 days, and Tom Sosnoff and Scott Sheridan have a lot to say about all of it. Tom shares what he told a room full of startup CEOs the night before about why professional networks are worth multiples — not percentages — of your net worth, and why most people have no idea what hidden opportunity they're leaving on the table. Then Scott breaks down outlier risk in plain terms: why trade size is the only real answer, why stress testing has limits, and what GameStop, Zoom, and Long-Term Capital Management all have in common. Sol keeps it real throughout.
#lossdog #optionstrading #careerdevelopment #networking #stockmarket #financialfreedom
TIMESTAMPS
0:00 Intro and hockey in Ovechkin's hallway
6:49 SEC signs off on PDT rule change
11:39 Tax Day check-in and show topics preview
12:50 Is any financial news source actually worth watching?
16:58 Building a professional network: cultivating relationships over a lifetime
20:47 Be a giver first: the goodwill model
23:22 Where to build connections and why remote work hurts
25:43 Be able to articulate your value clearly and quickly
30:34 Hidden opportunity only networks can unlock
32:59 Market update: S&Ps, NASDAQ near highs, short setups
38:43 Lossdog platform update: 2,000 new users and agentic AI
40:42 Outlier risk: why trade size is the only real answer
43:22 Fooled by randomness and model failure explained
47:46 Asymmetric loss
48:33 The insurance company analogy
49:17 Can you actually stress test for outlier risk?
52:35 Are outlier moves mean reverting?
56:24 Market Talk
Professional networks and outlier risk don't usually share a conversation, but they're connected by the same idea: most of what matters is happening off the public feed. The hidden job market, the private deal flow, the black swan move that stress tests can't predict — these are all features of a system where information travels through relationships, not headlines. With the PDT rule getting scrapped after 25 years, retail traders are getting a genuine shot at more active participation just as volatility starts to settle back down from the April spike. And with AI stress testing tools becoming accessible to everyday investors, the gap between institutional and retail risk management is narrowing faster than most financial media is willing to admit.
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://loss...
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