Description
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Tom Sosnoff breaks down his favorite trade—a 20 delta short put managed at 50%—while buying Bitcoin, ETH, Oracle, and Robinhood into a volatile selloff. With the VIX spiking above 20 and silver crashing from $92 to $73 overnight, the team gets into whether this counts as a crypto crash (spoiler: it doesn't), why MicroStrategy is now trading below its Bitcoin value, and the real danger of leveraged ETFs. Scott and Tom also share how they've handled disagreements over 35 years of partnership, plus callers ask about currency risk for Australian traders, scaling positions without blowing up, and managing underwater stocks with covered calls.
#saylor #strategy #mstr #bitcoin #lossdog #bitcoin #optionstrading #vix #cryptomarket #silvertrading
TIMESTAMPS
0:00 Intro
0:13 Tom's favorite trade: 20 delta short put managed at 50%
3:10 When to sell puts in high volatility markets
5:30 How Tom and Scott divided responsibilities building thinkorswim
6:38 The cost of democratizing trading: outliers and casualties
9:10 Is this a "do the opposite" moment?
10:48 Tom buying Bitcoin at $69K, ETH, Oracle, and Robinhood
12:06 MicroStrategy trading below Bitcoin value
13:58 Leveraged ETFs: why you shouldn't hold more than 48 hours
15:36 Currency risk for Australian traders
18:44 Tom and Scott's biggest business disagreements
22:11 Is this a crypto crash? Why orderly selling isn't panic
27:48 Active vs passive investing: the 6.7% reality check
32:24 How AI will change program trading algorithms
35:01 How Tom recovered from his GME loss
36:31 Caller: scaling into positions in a weak market
43:09 Small accounts under $5K: just get started
44:16 Caller asks if Lossdog will go public
45:58 What is Lossdog? High-level overview
47:38 Scaling trades: why you can't cherry-pick which ones to size up
50:42 Short premium in crypto: is downside tail risk priced correctly?
56:45 Caller: evaluating gold and silver ETFs without fundamentals
59:10 Market talk: S&P down 100, VIX exploding, bonds rallying
1:01:11 Tom's $200 Pokemon card accidental purchase at Costco
The VIX jumping above 20 while Bitcoin drops below $70K marks the first real test for a generation of investors who've only known crypto going up. With MicroStrategy down 75% from highs and now trading at a discount to its Bitcoin holdings, the question isn't whether to buy the dip—it's understanding why orderly selling differs from true capitulation. Meanwhile, the gold-silver ratio whipsawing from 58 to above 60 overnight shows just how much stress is building across asset classes, even as bonds finally catch a flight-to-quality bid.
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 1...
Tom Sosnoff breaks down his favorite trade—a 20 delta short put managed at 50%—while buying Bitcoin, ETH, Oracle, and Robinhood into a volatile selloff. With the VIX spiking above 20 and silver crashing from $92 to $73 overnight, the team gets into whether this counts as a crypto crash (spoiler: it doesn't), why MicroStrategy is now trading below its Bitcoin value, and the real danger of leveraged ETFs. Scott and Tom also share how they've handled disagreements over 35 years of partnership, plus callers ask about currency risk for Australian traders, scaling positions without blowing up, and managing underwater stocks with covered calls.
#saylor #strategy #mstr #bitcoin #lossdog #bitcoin #optionstrading #vix #cryptomarket #silvertrading
TIMESTAMPS
0:00 Intro
0:13 Tom's favorite trade: 20 delta short put managed at 50%
3:10 When to sell puts in high volatility markets
5:30 How Tom and Scott divided responsibilities building thinkorswim
6:38 The cost of democratizing trading: outliers and casualties
9:10 Is this a "do the opposite" moment?
10:48 Tom buying Bitcoin at $69K, ETH, Oracle, and Robinhood
12:06 MicroStrategy trading below Bitcoin value
13:58 Leveraged ETFs: why you shouldn't hold more than 48 hours
15:36 Currency risk for Australian traders
18:44 Tom and Scott's biggest business disagreements
22:11 Is this a crypto crash? Why orderly selling isn't panic
27:48 Active vs passive investing: the 6.7% reality check
32:24 How AI will change program trading algorithms
35:01 How Tom recovered from his GME loss
36:31 Caller: scaling into positions in a weak market
43:09 Small accounts under $5K: just get started
44:16 Caller asks if Lossdog will go public
45:58 What is Lossdog? High-level overview
47:38 Scaling trades: why you can't cherry-pick which ones to size up
50:42 Short premium in crypto: is downside tail risk priced correctly?
56:45 Caller: evaluating gold and silver ETFs without fundamentals
59:10 Market talk: S&P down 100, VIX exploding, bonds rallying
1:01:11 Tom's $200 Pokemon card accidental purchase at Costco
The VIX jumping above 20 while Bitcoin drops below $70K marks the first real test for a generation of investors who've only known crypto going up. With MicroStrategy down 75% from highs and now trading at a discount to its Bitcoin holdings, the question isn't whether to buy the dip—it's understanding why orderly selling differs from true capitulation. Meanwhile, the gold-silver ratio whipsawing from 58 to above 60 overnight shows just how much stress is building across asset classes, even as bonds finally catch a flight-to-quality bid.
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 1...
