One Lucky Dog

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff makes it back after a brutal night stranded in airports to break down everything you've been asking about Lossdog — what it actually does, how the April 1st launch works, and why the first 50,000 subscribers get a free year plus $1 million in crypto split between Bitcoin, Ethereum, Stellar, and Solana. Tom also gets into why crypto won't replace equities in a market crash, how volatility actually predicts expected move, and whether you should quit your job to trade options full-time. Callers bring real questions on SPX zero-day wings, trading from Asia, Canadian tax-sheltered account restrictions, and more.

#lossdog #optionstrading #stockmarket #salary #crypto #financialfreedom

TIMESTAMPS

0:00 Intro and show open

0:20 What is Lossdog? Full platform breakdown

5:05 Career scoring: how your Lossdog number works

6:00 Portfolio optimization side of Lossdog

7:17 Joined the waitlist — now what?

8:23 First 50,000 subscribers: free year + crypto rewards

10:51 Why Lossdog is free and giving away $1M in crypto

12:10 Non-US residents and the Canadian crypto restriction

16:05 Tom arrives after overnight airport travel chaos

17:12 Stablecoins as daily transaction tools

18:45 Could a market crash make crypto the last safe haven?

20:12 Triple witching week and today's market move

22:20 Caller Rick: SPX zero-day wings strategy

26:42 Trading from Asia — what markets actually work

28:49 Best and worst trade in the OEX pit

33:33 Canadian TFSA and RRSP options trading restrictions

36:15 Viewer thank-you: wheel strategy and put spreads

36:40 Delta/vega neutral portfolio and jump risk hedging

39:30 MU short update and triple witching positioning

40:33 Volatility explained: how it predicts expected move

42:41 Do you trade Forex? Currency futures vs. spot

44:47 GEX (gamma exposure) — is it useful for retail traders?

47:16 Trading as a business: floor trader life vs. today

51:02 College debt debate: best school vs. cheapest option

54:38 Is it more important to be right or admit you're wrong?

56:49 Should you quit your job to trade options full-time?

58:40 Market rundown: S&P, Nasdaq, gold, crude, volatility

The conversation around professional underpayment has gained serious traction in 2026, with workers increasingly aware that stagnant wages and opaque salary data cost them hundreds of thousands of dollars over a career. Lossdog enters that gap with an AI-powered platform trained on millions of resumes and hundreds of millions of data points — built to give people a real number, not a range. At the same time, markets are navigating a stretch defined by tariff volatility, rate uncertainty, and a crypto landscape being reshaped by stablecoin legislation and institutional inflows. The questions Tom fields today — from zero-day options mechanics to whether to leave a stable job for full-time trading — reflect exactly where retail traders and career professionals are right now: capable, informed, and trying to figure out how to stop leaving money on the table.

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...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff and Scott Sheridan get into the real math behind a $250K account chasing $5,000 a week — and why that goal needs a serious reset. They walk through how to size a volatility trading account, what IVR actually means when the VIX is above 25, and why the bond market right now is one of the most interesting trades on the board. Callers push the conversation into sports betting integrity, whether the 1% can actually move the stock market, and Tom's take on why the U.S. is likely to underperform global markets in 2026. And yes, someone asks if professional sports are fixed — and the answer is more nuanced than you'd think.

#lossdog #optionstrading #bondmarket #stockmarket #vix #sportsbetting

TIMESTAMPS

0:00 Intro

0:16 "Take Profit at 50%" explained for premium sellers

1:46 What is a long-term hold and how trades become one

4:46 Can you make $5,000 a week with $250K? Realistic expectations

7:48 VIX above 25 and what that means for IVR

10:03 Caller: Early assignment, SGOV, and margin interest explained

14:46 Caller Ryan: Bond market, the Trump put, and ZB futures

21:14 Risk arbitrage — why retail traders should stay away from merger plays

23:26 Caller Mohammed: What account size do you need to trade volatility?

26:41 Tail hedges using SPX puts — cost and mechanics

30:08 Are professional sports fixed? The gambling integrity problem

35:52 ROI on medical education — is 13 years of school worth it?

40:06 Trade small, trade often — can you diversify on one underlying?

41:29 Can options selling scale to millions like buying stocks did?

44:39 Simple options strategies with few legs

47:09 1% does not control the market

51:06 Will the U.S. stock market underperform the world in 2026?

52:34 Monthly dividend ETFs for retirees

53:39 Building a fintech

59:33 Market Talk: Oil at $96, VIX near 30, triple witching ahead

The bond market doesn't lie — and right now it's flashing warnings the Fed can't talk its way out of. With the 30-year yield spread at multi-year wides, oil surging back toward $100, and the VIX hovering at 50% above its historical mean, traders are navigating one of the more genuinely volatile macro environments in years. Meanwhile, the explosion of legalized sports betting has created a credibility problem for professional leagues that mirrors a broader trust deficit playing out across American institutions — from politics to financial markets. These aren't isolated conversations. They're part of the same question: who do you trust, and how do you protect yourself when the systems around you are under pressure? That's exactly the kind of clarity Tom, Scott, and Sol are building toward — both on the show and through the Lossdog platform.

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 care...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff breaks down the one risk management principle that's crushed even Nobel Prize-winning traders—and it's not what most people expect. Scott Sheridan gets into active vs. passive portfolio separation, exactly how much buying power to use based on VIX levels, and the right way to size positions whether your account is small, medium, or large. A caller from Scranton walks through a live oil trade he put on with his son, a former accountant writes in about feeling replaced by AI and whether trading can fill the gap, and the crew fields a tough career question: what do you actually do when a senior co-worker shifts blame onto you and steals your credit? Plus, gold and crude oil behaving like meme stocks, Oracle earnings, and a live look at today's markets.

#lossdog #optionstrading #riskmanagement #careerdevelopment #stockmarket #financialfreedom

TIMESTAMPS

0:00 Intro

0:11 What being a contrarian actually means to Tom

3:36 Should you separate your trading and investment accounts?

7:42 The one risk management rule that kills even great traders

10:54 Globex trading after hours

12:47 Position sizing formula by account size

15:18 Ditch trading and grow the business?

19:21 Mark from Scranton: live oil trade with his son

23:20 Managing losing trades: 45 DTE and the 21 DTE rule

25:11 Gold above $5,000—what actually changed

27:35 Commodities acting like meme stocks in 2026

30:58 Career question: when a co-worker steals your credit

33:54 When to take a loss: rule

35:54 BP usage based off VIX

38:20 Earnings knee-jerk reactions—who's really causing them?

42:59 Jake from Chapel Hill: worst advice you ever followed

47:18 Former accountant: can trading replace a career?

50:24 Will the gig economy replace full-time employees?

52:51 Over 50 and just started trading—can you still retire early?

55:30 Market Talk: oil, Bitcoin, Oracle, bonds

One of the hardest things about markets right now is that volatility doesn't just create opportunity—it creates overconfidence. When implied volatility spikes and commodities start moving like GameStop circa 2021, the temptation to go bigger is exactly when most traders get into trouble. The same dynamic plays out in careers: when the ground shifts under you—layoffs, AI displacement, industry consolidation—the instinct to make a dramatic pivot can be just as dangerous as sizing up on a bad trade. What today's show keeps coming back to, from position sizing to whether a contractor economy can replace W-2 work, is the same underlying idea: process and consistency beat conviction almost every time. In a year where gold, silver, and crude oil are drawing in retail traders the way meme stocks did in 2021, knowing your number—whether that's your max loss threshold or your actual market value as a professional—is the edge most people don't bother to find.

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 conversa...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff and Scott Sheridan don't hold back on the CEO-to-employee salary gap—sharing data from the Lossdog platform showing most CEOs are overpaid by around 50%, while most workers are underpaid by millions. They also get into favorite stocks to trade right now, how to scalp futures with real profit targets, the right way to size iron condor credit, whether 24/7 options markets will actually change anything, and what's really going on with MicroStrategy borrowing hundreds of millions at 11.5% to buy Bitcoin. Callers bring contrarian SPX trades and real questions about AI killing jobs, and the show wraps with a live market rundown on a wild volatility day.

#lossdog #optionstrading #salaynegotiation #stockmarket #bitcoin #careers

TIMESTAMPS

0:03 Intro & show open

0:11 Favorite stocks to trade right now

3:33 Tom's guide to scalping every asset

5:14 Iron condor credit targets explained

9:02 Dog Pound: ES gap fill—what would it take?

12:51 CEO vs. employee salary gap—Lossdog data

17:45 Should you negotiate salary with AI replacing jobs?

19:44 Is the Federal Reserve still necessary?

22:23 Skewing iron condor legs—when and how

24:34 Contrarians everywhere, except markets

26:24 Scalping futures: stops, targets, and time frames

28:17 Weekend risk and selling weekly credit spreads

31:24 Weeklies credit spreads

34:03 Caller: contrarian SPX trades and the 2009 low

39:50 24/7 options markets and zero DTE trading

41:39 Bitcoin—the most important question before you buy

44:00 Caller: 18-year-old asks which jobs AI will destroy

46:54 MicroStrategy's $383M Bitcoin debt - scam?

51:16 Recession or depression in 2026? Macro breakdown

53:17 Long straddles working in gold and silver right now

54:47 How market makers fill orders when spreads go wide

59:01 Market Talk: S&Ps, oil, gold, VIX, Oracle

The CEO-to-worker pay gap isn't a new story, but it's getting harder to ignore—Starbucks has reportedly run a ratio near 6,000-to-1, and Citigroup sits around 450-to-1, against a backdrop where most people have no idea how underpaid they actually are relative to their real market value. On the trading side, today's session was a live case study in volatility: crude oil swung $30 in a day, the S&P 500 ripped nearly 250 handles from Sunday's lows, and the VIX dropped more than 10%—exactly the kind of environment where scalping discipline, iron condor management, and weekend risk awareness go from theory to real money. Meanwhile, the debate around MicroStrategy's leveraged Bitcoin playbook puts a spotlight on a familiar financial dynamic: when fund managers are playing with other people's money, the incentive to chase yield at almost any risk level is very, very real.

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...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Oil just had its biggest single-day move in futures history — up 35% in a week — and Tom Sosnoff was short when it happened. Tom, Scott Sheridan, and Sol break down how to trade crude using /CL and /MCL contracts, why oil ETFs are a trap, and what wide strangles look like when IVR hits 130. They also get into box spreads, whether AI can actually predict market moves, the iron condor vs. synthetic strangle distinction, when to take profits on strangles, and how long-time employees near retirement can fight for better pay. Callers from Connecticut, Japan, Fort Worth, Switzerland, and Chapel Hill bring real trading questions and career stories to the table.

#lossdog #oiltrading #optionstrading #sellingpremium #careerdevelopment #financialmarkets

TIMESTAMPS

0:00 Intro

0:11 Oil's record move and how to trade it

4:39 /CL vs /MCL contracts and oil options

7:44 Oil's inverse correlation with the S&P

8:26 Why you should trade small in volatile oil

9:53 What is a box spread and who uses it

13:00 Can AI algorithms predict the market?

18:49 Caller: Early career mistakes that led to success

21:05 Finfluencer panel and the Gen Z work ethic debate

23:07 Caller: Starting options trading with a $70K account

26:54 Caller from Japan: Yen puts and iron condor vs. synthetic strangle

32:17 War fears, oil geopolitics, and market impact

36:13 Why Tom and Scott are short premium on gold and silver

38:16 Can you hedge with VVIX? Why buying volatility here is risky

40:31 Advice for a trader who lost money and made it back

45:16 Does trading help a marriage?

46:00 Long-time employees vs. new hires: negotiating your worth

49:06 When to take profits on strangles

51:02 Caller: Managing a short straddle on micro crude

54:01 Caller from Switzerland: Options selling community invite

58:01 Market Talk: rundown and VIX analysis

Oil futures just posted a 35% weekly gain, the largest since crude started trading in 1983, with prices swinging from $91 to nearly $120 before settling around $100. That kind of move ripples through everything — gas prices at the pump jumped 40 cents in a week, the S&P traded inversely tick-for-tick with crude overnight, and the VIX sat at 28 while VVIX hit 136, roughly 40% above normal levels. For retail traders, this environment is a masterclass in why position sizing matters and why selling premium at extreme implied volatility ranks has historically outperformed buying protection at inflated prices. Meanwhile, the broader conversation around AI-driven trading algorithms, retirement-age salary compression, and Gen Z's relationship with work ethic reflects a labor market still sorting out what skills and loyalty are actually worth in 2026.

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 care...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff makes the case that crude oil is the single most overrated market narrative right now — up 30% off its lows with options premiums getting pumped to an IV rank of 112. Scott Sheridan counters with the "buy the dip" mentality and overhyped AI as the bigger risks. The show also gets into the exact theta-to-net-liq ratio you should target (0.1% to 0.3%), why VIX calendars can blow up your account, what the future of financial advising really looks like in an AI world, and whether zero-day adjustments actually improve your P&L. Callers ask about the best thing to start doing at 19, trading only futures options strangles, and how futures options settle at expiration.

#lossdog #crudeoil #optionstrading #financialadvisor #zeroDTE #careerdevelopment

TIMESTAMPS

0:00 Intro

0:04 What's the most overrated market narrative right now?

2:39 Tom's case for shorting crude oil

3:23 Crude oil options premiums exploding today

5:29 Dean asks: biggest business failure you learned from

9:44 Trading only futures options strangles — is it viable?

12:02 Theta-to-net-liq ratio: the exact numbers to target

13:44 Yunior from Florida and the dream of 24/7 tokenized trading

17:07 Saylor asks: what to start doing at 19

20:30 How to pitch Lossdog to friends and family

22:34 Why you should never trade VIX calendars or diagonals

24:53 The future of financial advising and how AI changes it

28:22 Gold zero DTE contracts vs. forward month liquidity

29:54 NC State student asks how to learn trading

33:50 Do you adjust your zero-day positions?

36:02 LEAPS spreads vs. 40-day expirations

38:28 What would the Fed need to do to crash the market?

42:08 Futures options settlement

44:13 Iran conflict, oil prices, and market jitters

47:03 Do markets rally after Canadian stat holidays?

50:51 Mike from Pennsylvania and the Dylan Ratigan shoe story

56:56 Market Talk: oil, S&Ps, VIX, bonds, and Chinese stocks

59:20 IV rank explained — it's real-time, not delayed

1:00:57 Why scalping futures never gets easier

The financial advisory industry is heading for a major shakeup as AI gives every advisor access to the same information that used to be locked behind firm walls. That shift mirrors what online trading did to brokerages two decades ago — more access, better tools, compressed pricing. Meanwhile, crude oil's 30% rally off recent lows has options markets flashing warning signs with implied volatility rankings above 110, and the Iran conflict adds another layer of uncertainty to an already jittery market sitting just 200 S&P points from all-time highs. For younger investors and career changers, the conversation keeps coming back to the same theme: take risk early, stay engaged, and learn by doing rather than waiting for the perfect moment.

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...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Markets opened ugly on March 3rd — stocks, crypto, bonds, gold, and silver all getting hit at once — and Tom and Scott didn't sugarcoat it. They walked through exactly how they're managing positions in real time: rolling down calls, nibbling on high-beta names, selling bond puts at levels they'd been watching, and why staying small right now isn't just advice — it's the only move that makes sense. Beyond the sell-off, they got into hedging crypto with Coinbase call spreads, their favorite pairs trades (gold-silver, ES-NQ, bonds vs. notes), the real difference between SPX and SPY for options traders, how to read delta on a put spread correctly, and why the AI trading era is about to make all of this a lot simpler. Callers included a first-timer from Florida asking about building a new exchange, a student from Chapel Hill getting the honest truth about marketing, and a dad from Scranton trying to get his 19-year-old son hooked on trading.

#lossdog #optionstrading #stockmarket #marketcrash #daytrading #financialfreedom

TIMESTAMPS

0:00 Intro

0:11 Morning sell-off — how to respond when everything is red

4:40 Every asset class down at once — what that means

5:07 Barry — rolling calls and managing delta under pressure

8:36 Caller Ryan — finding entries and where Tom is nibbling

13:58 Hedging crypto with Coinbase call spreads

17:00 Best pairs trades to know: gold-silver, ES-NQ, bonds vs. notes

21:05 Caller Yunior — the Small Exchange story and what Tom is building next

25:06 Caller Sawyer — wildest marketing wins and disasters (the CNBC $500K story)

30:56 SPX vs. SPY — the real reason most traders stick with SPY

34:45 Standard deviation, implied vol, and how delta fits together

36:33 How to read delta on a put spread the right way

38:22 Finding high-probability premium selling opportunities fast

42:07 Caller Mark - how to get the young generations interested in trading

47:35 Caller Paul — rolling iron condors without doubling your buying power

50:37 Which asset class bounces first after a major sell-off

53:24 Shorting the market in December 1999 — how bad was it really?

57:34 Live market snapshot and what to watch going into the afternoon

Today's session is a reminder that markets don't care about your game plan — they care about whether you're sized right and thinking clearly when things go sideways. Volatility spikes like the one on March 3rd, with VIX cash up nearly 20% intraday and futures volume hitting full-day averages before 10am Central, are increasingly becoming a feature of a market still navigating geopolitical chaos, tariff uncertainty, and a macro backdrop that hasn't fully resolved. For options traders, these are the moments where understanding expected move, pairs relationships, and the mechanics of rolling positions separates disciplined traders from people just reacting. The comparison to December 1999 — when the NASDAQ eventually lost 80% of its value over two years — is a useful calibration: today's volatility, while real, is still operating in a structurally different environment. Knowing the difference matters.

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 g...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Markets opened in chaos Monday morning—S&Ps down 100 overnight, gold flying, silver whipsawing, oil gapping up $7 before fading. Tom Sosnoff and Scott Sheridan break down how to actually trade geopolitical shock without getting wrecked by the news cycle, including the one rule that separates good traders from reactive ones: trade the tape, not the fear. Then it's a full session of caller questions covering zero DTE mechanics, when to recenter a blown strangle, how to screen for high-probability premium selling opportunities on tastytrade, and exactly how much buying power to keep dry when the VIX climbs into the 20s. A Cornell student building an AI trading discipline tool calls in for advice, an 18-year-old asks what to do with $10K, and a silver trader gets a live trade fix in real time.

#lossdog #optionstrading #zerodtetrading #stockmarket #volatility #financialfreedom

TIMESTAMPS

0:00 Intro & show preview

0:09 Trading the Iran conflict — letter from Gary

2:40 Trade the tape, not the news

7:14 When to recenter a trade — buying the guts, selling the wings

9:05 Netherlands taxing unrealized gains — complete disaster?

12:58 Buy, Borrow, Die strategy explained

14:40 Crypto liquidity pools and the Lossdog stablecoin

17:10 Caller Satya: building AI tools to reduce emotional trading drawdowns

22:41 Caller Steve: zero DTE wing strategy — same day vs. back month wings

30:34 Caller Tyler: what to do with $10K at 18 years old

35:25 Caller Daniel: fixing a blown silver strangle + ideal account size for options

40:22 How to find the best options to sell — IVR screener walkthrough

42:45 Next options strategy for beginners — covered calls to put spreads

45:06 Choosing the right expiration series for 1–5 day trades

46:45 Redeployment after a winning iron condor — when to reload

48:52 SPX put selling — how much buying power to keep dry

53:51 Market talk — gold, silver, Bitcoin, bonds, VIX, Netflix, Oracle

Geopolitical shocks hit markets fast, but they rarely hit in a straight line—and Monday March 2, 2026 was a perfect case study. The overnight S&P futures dropped 100 handles on Iran conflict headlines, only to recover most of the move before the open, leaving traders who chased the news on the wrong side. That pattern isn't new: markets have repeatedly shown that the first violent reaction to geopolitical events overshoots, and the real opportunity is in recognizing the overshoot rather than predicting the headline. Meanwhile, with VIX still elevated in the low 20s heading into the week, premium sellers face the classic tension between deploying more capital when vol is rich and keeping enough powder dry to survive a real move. Research going back to 2008 shows that maintaining 40% excess buying power through drawdowns has historically prevented margin-forced liquidations—a number that's easy to ignore when a put-selling strategy has been working for years, and critical when it finally doesn't.

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...

Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

Tom Sosnoff and Scott Sheridan break down exactly why Lossdog is giving away $1 million in cryptocurrency, which four coins are included, and how the giveaway actually works. They also get into the best way to earn interest on idle cash across brokerage accounts, why rolling SPX puts at 21 DTE beats holding to expiration, and Tom shares his favorite zero DTE options strategy using expected move strangles. Plus, a caller from Miami asks what stablecoins actually do that a money market doesn't, and the team talks NVIDIA's post-earnings selloff and what it means for tech.

#lossdog #cryptocurrency #optionstrading #stablecoin #nvidia #zeroDTE

TIMESTAMPS

0:00 Intro

0:17 Why Lossdog is giving away $1M in crypto

1:40 Which four coins and why (BTC, ETH, SOL, XLM)

3:00 Crypto held in Zero Hash omnibus wallet

3:54 Best way to earn interest on free cash (treasury ETFs)

6:33 Coins, change jars, and the death of physical currency

9:10 Rolling SPX puts at 21 DTE vs. holding to expiration

10:59 Financing a $500K business with Chinese vs. U.S. capital

14:41 Lossdog stablecoin and cross-border payments explained

16:10 How to trade crypto options in the U.S. right now

18:43 Caller Steve: stablecoin vs. money market vs. Bitcoin

26:19 Why an 88-year-old should sign up for Lossdog

28:36 How to pair and roll multiple strangles by price

31:30 Lossdog swag store reminder: www.swag.lossdog.com

37:22 New micro futures launching in 2026

40:47 No hat Tom

42:57 How Tom and Scott fought for universal spread margining - Trading with limited capital

48:45 Caller Cesare: oil trading strategy and favorite muscle cars

53:54 Best zero DTE strategy: selling the expected move strangle

58:32 Market Talk: NVIDIA earnings selloff and market rundown

The $1 million crypto giveaway comes at a time when stablecoins are moving from niche use case to mainstream financial tool, with legislation advancing in Congress and major platforms racing to integrate digital currency products. For traders, the distinction between stablecoins and volatile crypto like Bitcoin has never mattered more — one acts like a digital savings account earning around 4%, the other carries real principal risk. Meanwhile, NVIDIA's post-earnings fade despite beating numbers reinforces a pattern across mega-cap tech: even strong results aren't enough when valuations already price in perfection. Zero DTE options continue to see explosive volume growth, and understanding expected move mechanics is becoming essential for anyone trading short-dated premium.

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

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Tom Sosnoff and Scott Sheridan get real about why Bitcoin is "dead money"—not because it's worthless, but because nobody ever sells it. Tom shares how losing his password accidentally turned into a win, and Scott pushes back on the idea that holders never crack under pressure. The conversation shifts to a jaw-dropping story about a $250 million acquisition that fell apart when a competing buyout derailed everything—and the target company later hit $1.5 billion. Cynthia from Virginia calls in about executive presence and what makes leaders instantly credible (spoiler: it's not your resume). Plus, the team breaks down SBLOC strategies, covered call management, iron condor mechanics, convexity models, and what really controls futures prices overnight. NVIDIA earnings loom large over the whole session.

#lossdog #bitcoin #optionstrading #nvidia #executivepresence #careerdevelopment

TIMESTAMPS

0:00 Intro

0:11 Do Bitcoin hoarders keep the price from dropping?

1:13 Why Bitcoin is "dead money" that never comes out

4:14 Tom's Bitcoin password story and holding psychology

7:05 Lossdog launch list: free crypto for first 50,000 signups

7:43 Cynthia from Virginia: what makes executives instantly credible

10:04 Likability as the single biggest leadership factor

11:18 Confidence and how leaders act when things go wrong

13:39 Scott's story about a departing employee he'll never forget

18:31 The $250M deal that got away during the pandemic

21:29 The thinkorswim sale: three options, none of them perfect

22:50 SBLOC strategy: borrowing against securities for leverage

25:50 What's next after zero DTE options?

28:28 Physical commodity hedging with futures and futures options

30:45 Covered calls gone right: what to do when the stock soars

32:37 Iron condor management: stay mechanical at 21 DTE

36:02 Best trading indicators: price extremes and fading friends

37:06 NVIDIA earnings preview and put-call skew breakdown

39:40 Caller Mark: put-call parity and credit spreads explained

43:15 Win percentage too low? She's probably managing too late

46:37 Convexity models and vol dispersion: why retail can't pull it off

52:36 Who really controls futures prices overnight?

58:10 Market talk: spooz, gold, VIX, and NVIDIA positioning

The crypto selloff and Bitcoin's drop from all-time highs is testing a generation of holders who swore they'd never sell. Meanwhile, the options market keeps evolving—zero DTE products already dominate volume, and event-based exchanges are pushing toward hourly and 15-minute binaries. With NVIDIA earnings driving single-stock implied volatility to 56% versus 24% in the QQQs, the gap between individual names and index vol creates textbook dispersion setups that remain nearly impossible for retail to execute profitably. Executive presence and leadership credibility are getting fresh attention as companies restructure and new founders like Cynthia carve out consulting niches in corporate training—a space where soft skills are finally being treated as teachable, measurable advantages.

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 ea...