One Lucky Dog

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Tom, Scott, and Sol open the week with a loaded mailbag: why AI is game-changing for portfolio optimization but probably can't beat the market as a trade engine, what stablecoins actually are and why a Lossdog debit card changes everything, and whether the so-called "SaaS apocalypse" is a real threat or just normal cyclicality after two decades of tech gains. Scott breaks down why futures commissions are higher than options—and why they're actually not once you do the math on notional size. The crew also gets into what college degree makes sense right now, how to structure employee bonuses, AI's real regulatory and funding risks, and caps the show with live market talk on a rough Monday for the Nasdaq.

#lossdog #stockmarket #optionstrading #stablecoin #artificialintelligence #career

TIMESTAMPS

0:00 Intro

0:10 Can AI be used as a trade engine?

3:56 Stablecoins: transactional or digital currency gateway?

8:50 Will Lossdog add trading features?

10:36 Are futures commissions negotiable?

14:45 Best college degree right now

19:31 CME fees: same for all brokers?

20:20 Auto-callable structured products explained

25:03 How to structure employee bonuses

28:58 The SaaS apocalypse—real or overblown?

33:41 Butterfly strategy for 0DTE and weekly options

37:20 ES strangles in a $150K account

39:35 Starting a trading business for tax advantages

42:28 AI's biggest vulnerabilities over the next 5 years

49:45 Dogs of Lossdog: new puppy

51:11 New social contract in the AI era

57:12 Congratulations USA Hockey gold medal

1:01:29 Market talk: gold, silver, Nasdaq, NVIDIA earnings

With AI spending cuts, a volatile macro backdrop, and NVIDIA earnings on deck Wednesday, this episode lands at a moment when nearly every topic discussed is actively playing out in real time. The debate around stablecoins as transactional currency is accelerating—legislation is moving and major fintech players are positioning. On the career side, the tension between STEM degrees and passion-driven paths is sharper than ever as AI reshapes which roles are actually in demand. And the "SaaS apocalypse" framing, however dramatic, reflects a genuine market reevaluation of software valuations that has wiped billions in market cap from names that were priced for a frictionless AI tailwind that hasn't fully materialized yet.

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

📧 [email protected]

🐕 Follow @wearelossdog everywhere 👉 http:...

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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

Tom Sosnoff breaks down why financial advisor fees sitting at 60 basis points across $30 trillion in assets are about to get crushed by AI — and why that's a massive win for consumers. Scott Sheridan walks through the math on a potential 20% market meltdown in 2026 (spoiler: the options market puts it at 30%), plus how to actually position for downside risk without panicking. The show also gets into natural gas strangles, the pattern day trading rule update, staggered profit-taking mechanics, and whether AI will widen or shrink the executive pay gap. Callers Vince and Kirsten bring real questions on delta selection and decision-making instincts.

#lossdog #financialadvisor #optionstrading #naturalgas #stockmarket #careergrowth

TIMESTAMPS

0:00 Intro

0:15 Are financial advisors worth 1% in fees?

1:46 AI will crush advisory fees to 20-25 basis points

4:56 Do you even need an advisor? The empathy argument

6:44 What are the chances of a 20% market crash in 2026?

8:02 The delta math behind a 30% meltdown probability

8:40 How to trade downside risk with put spreads and covered calls

10:28 Caller Vince: straddle vs strangle on natural gas

15:49 Optimal delta for natural gas strangles

18:36 Most important skills for entrepreneurs from college

21:26 Preserving trading profits and the 40/40/20 allocation rule

25:03 Pattern day trading rule update and FINRA timeline

28:21 Staggered profit-taking and when to sell premium

30:03 Lossdog's mission to flip the script on AI risk

31:38 Managing risk at 65

33:08 Demographics poll and Tom's fashion roast

36:03 Explanation of potential assignment on /ES and /MES

40:01 Is there such a thing as a Fed put?

41:26 AI's impact on the RIA space and fee compression

42:41 Will AI widen the executive pay gap?

45:31 Selling a LEAP put to fund a LEAP call — does it work?

50:18 AI energy consumption and the electricity overproduction question

52:23 Caller Kirsten: interoception and trader decision-making

57:06 Market talk: Bitcoin, oil, gold, and a flat trading day

1:00:02 Dog Pound poll: Iran's Supreme Leader and food scene tangent

1:02:00 Cocoa market and why retail can't trade it

The conversation around advisory fees hits at a moment when the wealth management industry controls roughly $30 trillion in assets at an average cost of 60 basis points — and AI is threatening to compress that to a fraction of what it is today. At the same time, with VIX hovering just under 20 and options math pricing a 30% probability of touching a 20% drawdown this year, the question of how retail traders should position for risk has never been more practical. The pattern day trading rule, a relic that has restricted accounts under $25,000 for over two decades, is finally entering its final comment period with FINRA, potentially dropping the threshold to just $2,000. Meanwhile, the broader debate around AI and the labor market — from entry-level job displacement to executive pay gaps — is shifting from theoretical to urgent as AI agents start handling tasks once reserved for human professionals.

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...

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

Tom and Scott open by shutting down the viral fear that investment firms can seize your IRA—breaking down exactly what segregated funds and rehypothecation actually mean and why this is pure clickbait. From there, the show gets into the mechanics of futures trading: micro contracts, buying power requirements for MES, how to use options on futures for pairs trades (and why 99% of the time you shouldn't), and the cleanest explanation of marketable limit orders you'll hear—complete with a spirited Tom vs. Scott debate. The back half covers why 58% of the audience has never touched Bitcoin and why that's a problem, how Lossdog plans to track career performance the way you'd track an investment portfolio, and whether the current macro environment actually justifies going more defensive given a VIX sitting right at its long-term average.

#lossdog #optionstrading #futurestrading #bitcoin #stockmarket #investing

TIMESTAMPS

0:00 Intro

0:13 Can investment firms steal your IRA?

0:53 Rehypothecation and segregated funds explained

4:28 Lossdog AI platform: options trading as a training ground

7:29 Tracking career performance like an investment portfolio

10:25 Trading futures with a small account: micro contracts

15:07 MES buying power requirements and volatility

16:53 Options on futures for pairs trades: why futures win

20:32 How investment strategy changes as you build wealth

26:56 2s vs 10s yield curve trade: futures or options?

29:40 Marketable limit order explained (Tom vs. Scott debate)

35:57 Earning interest on idle cash without buying power reduction

37:53 Naked options on futures: optimal delta targets

40:20 Dog Pound poll: 61% of active traders are up in 2026

42:15 MOC orders in the SPX

47:24 Why you should own at least some Bitcoin

54:01 Should you go defensive? VIX, long vol vs. dialing back delta

58:54 Market Talk: S&P rally, gold, Oracle, Bitcoin

The conversation spans two of the most overlooked financial literacy gaps right now: understanding how brokerage accounts actually work versus how fear-based media portrays them, and why so many retail traders still have zero exposure to digital assets. The options mechanics covered here—pairs trades, delta targets, marketable limit orders—reflect real decisions active traders face in a market sitting less than 2% off all-time highs with the VIX near its historical average of 18. Meanwhile, the Lossdog platform's career-tracking feature speaks to a broader shift: people are starting to apply the same performance accountability they use for portfolios to their professional lives, a habit that's been standard in finance but almost nonexistent everywhere else.

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: M...

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

Tom Sosnoff explains why he built thinkorswim without charts and still doesn't use technical analysis — and what he actually uses instead. Scott Sheridan breaks down the pattern day trader rule and why it's almost gone, plus both get into the real mechanics of trading small accounts: when to take profits, undefined vs. defined risk, backtesting vs. stress testing, and how to think about the yield curve. Callers bring it with a silver puts trade post-mortem, a question on BRICS and the US dollar, and a cost-basis-to-zero covered call story that earns a rare A+. The show wraps with a live market rundown covering Bitcoin, gold, silver, NASDAQ, and individual names.

#lossdog #optionstrading #stockmarket #smallaccount #patterndaytrader #yieldcurve

TIMESTAMPS

0:00 Intro

0:12 How to start trading options the right way

3:02 Why Tom doesn't use technical analysis

7:20 Weekend and after-hours trading with a small account

09:57 CME single-stock futures: what's coming and what it means

13:42 Can a 77-year-old retired investor use Lossdog?

16:44 Caller Hugh: Small Exchange story, pattern day trader rule and when it's gone

24:04 Caller Cesare: silver puts win, swing trade exit strategy, 50% profit target

33:36 Caller Mike: BRICS, US dollar weakness, and gold

38:15 Options-only portfolio — is it a real strategy?

39:22 Covered calls to zero cost basis: is there a better way?

48:23 Warren Buffett on temperament vs. intelligence in trading

54:46 Caller Mark: backtesting vs. stress testing your account

57:06 Undefined vs. defined risk for small accounts

58:43 Live market rundown: Bitcoin, gold, NASDAQ, Apple, Oracle, Walmart

The pattern day trader rule has been a real ceiling for small accounts for over two decades — limiting traders under $25,000 to three round trips in a rolling five-day window. With the SEC comment period winding down in early 2026, that rule looks like it's finally on the way out, potentially as soon as March or April. At the same time, the CME's push into single-stock futures on names like Nvidia and Tesla is reopening a debate that last played out in the early 2000s, when NQLX and One Chicago tried and failed to build a retail market for these products. The broader backdrop — dollar weakness, BRICS noise, a NASDAQ that swung 350 points in a session — is the kind of environment where knowing your risk structure and profit targets matters more than ever.

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

📧 [email protected]

🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog

Everyone has a number. Lossdog helps you know your number, and grow your number.

👉 Join...

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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

Tom Sosnoff and Scott Sheridan break down why widening spreads should always come before adding contracts when scaling your options trades. They get into how to handle toxic coworkers in flat organizations, what the silver crash taught traders about managing volatile instruments, and why taking a pay cut for the right opportunity might be the smartest career move you make. Plus: how to read the market after a crash, when tech jobs will recover, and a heated debate about whether corporate culture actually matters.

#lossdog #optionstrading #careerdevelopment #stockmarket #financialfreedom #tradingstrategy

TIMESTAMPS

0:00 Intro

0:10 Why you should always widen spreads before adding contracts

3:05 How to deal with toxic employees in flat organizations

8:19 Managing iron condors based on volatility levels

10:47 Caller Larry asks about defensive positioning after losses

15:03 Caller Vince asks about the Lossdog platform and pricing model

19:12 New CME silver and gold micro contracts explained

20:49 Caller Eduardo on taking a pay cut for career fulfillment - stay the course

26:52 In a 'crash' how do you asses the market and find opportunities

32:02 Open Interest in newly tradeable puts

33:25 How to get your first customers when starting a business

37:02 Who was your most important mentor

43:08 Does corporate culture actually matter for success

48:18 When will the tech job market recover

51:44 Government taking stakes in private companies poll

52:50 Should you buy back the short leg of an iron condor for five cents

54:29 Best spread width strategy for a $2,000 account

56:38 Market talk: Bitcoin, oil, Netflix new lows, Coinbase earnings

The tension between AI and traditional software development is creating a two-tier tech job market where the top third who understand AI integration are thriving while others struggle. Commission compression over the past 25 years has made strategies like five delta wide credit spreads viable for retail traders when they used to be eaten alive by fees. Career pivots that involve short-term pay cuts often create network effects and learning opportunities that compound over time, especially when moving into fields you genuinely find energizing.

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

📧 [email protected]

🐕 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/

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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

Tom Sosnoff and Scott Sheridan break down how to build a core-satellite options portfolio, share wild stories from their early trading floor days including a trader who lost $4 million in a single afternoon, and explain why selling naked puts beats put spreads almost every time. They also get into the 401k vs Roth debate, overnight futures orders, and why disciplined smart people sometimes fail at trading while high school dropouts crush it. Plus, a heated debate continues on whether politicians should be allowed to trade.

#lossdog #optionstrading #nakedputs #401k #tradingpsychology #futurestrading

TIMESTAMPS

0:00 Intro

0:19 Building a core-satellite options portfolio

2:39 Why lowering your cost basis is the real goal

4:44 How much trading capital do you need to start trading

6:22 Tom's first trading stake and losing it in two weeks

7:56 The stranger who lent Tom $100K in 1980s Chicago

12:35 Overnight resting futures orders: open vs close

15:34 How to convert a leveraged ETF into a futures position

20:55 Widening spreads and using more buying power

22:23 Caller Loki asks about 401k contributions and Roth vs traditional

26:33 Should you stop trading after hitting your annual goal

28:49 Put and call skew across stocks, ETFs, and indices

30:50 Caller Charlie asks about naked puts vs spreads

32:50 Trading with 70-80% of your net worth

37:18 Caller Steve reignites the politician trading debate

46:15 VIX and S&P correlation explained

52:17 Why smart, disciplined people fail at trading

59:24 Caller from Utah Crypto allocation: how much is too much

1:01:57 Market talk and earnings plays

The conversation about politician trading restrictions continues to divide audiences, with 72% of viewers favoring more restrictions while Tom argues that allowing politicians to trade keeps them financially literate and connected to market structure. Meanwhile, the hosts share hard-earned wisdom about trading psychology: the difference between hearing a closing order fill at 3 AM versus an opening order is the difference between sleeping soundly and staring at the ceiling. With the S&P flirting with 7000 and volatility compression finally hitting precious metals, the current market environment rewards traders who understand position sizing and know when to stay in the game.

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

📧 [email protected]

🐕 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/

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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

Tom Sosnoff and Scott Sheridan break down how to trade a dollar rebound with a small account, explain why 401k inflows contribute to positive drift (but aren't the whole story), and deliver a brutally honest take on why outside consultants are usually a waste of time and money. They also walk through spread order routing issues, explain why sports betting markets are structured against you even when you win, and answer whether you should rent or buy real estate for your business. Plus: caller questions on trading currency futures, managing broken wing butterflies, and getting started in investing without paying for courses.

#lossdog #stockmarket #optionstrading #career #financialfreedom #trading

TIMESTAMPS

0:00 Intro

0:16 How to trade dollar rebound with $15K account

2:20 Best currency futures for dollar plays

4:10 401k contributions and positive drift theory

8:59 Super Bowl odds and President's Day schedule

11:01 IVR explanation: higher is better, no maximum

15:17 The consultant horror story from London - Why consultants destroy value

20:38 Caller Kirsten: Tom and Scott brand analogy

23:43 Arthur calls: trading Kyndryl after 53% drop

27:30 Tom's Super Bowl spread and burnt ends chili recipe

31:06 Managing broken wing butterflies and rolling strategies

34:04 Tom wins all three Super Bowl bets

36:13 LLC vs C-Corp for raising capital

38:13 Bitcoin is the flight to quality crypto

39:55 Shorting crypto cash market discussion

41:07 Why sports betting markets are horrible

44:55 Real estate: rent vs buy for business

47:56 Spread order routing and cancel-replace strategy

51:30 Beginner investing advice: just start doing it

55:42 Market talk: crypto, stocks, Robinhood rally

The dollar just got crushed to multi-year lows, and retail traders want to know how to play the rebound without risking huge capital. Currency markets are tricky—most ETFs barely move, and futures can feel inaccessible—but there are liquid plays like the euro futures (forward slash 6E) that work even in smaller accounts. At the same time, the "positive drift" debate continues: are 401k contributions really propping up the market, or is it just the natural reward for taking risk in a bull market with low rates? The real answer is more nuanced than either narrative. Meanwhile, the consultant industrial complex keeps selling workshops to companies that don't need them, sports betting continues to extract massive edge from retail bettors (even winners), and the eternal question of whether to rent or buy business real estate still doesn't have a one-size-fits-all answer. The common thread: understanding structure, incentives, and who's on the other side of your trade matters more than most people think.

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 bu...

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

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...

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

Tom Sosnoff breaks down why buying VIX calls to hedge your SPX iron condors is like paying four times your premium for hurricane insurance that expires worthless. Scott Sheridan shares the story of how a private equity firm told them they wouldn't know a CFO if it hit them in the ass, then they found Christy Ross anyway. The team gets into whether AI will level the playing field for entrepreneurs, what happens when U.S. debt doubles to $80 trillion, and why software stocks are bleeding while gold whipsaws $80 in a single session. Callers ask about scalping vehicles, charm heat maps for zero DTE, and the best low-risk income strategies that don't involve short premium.

#lossdog #optionstrading #stockmarket #salarynegotiation #ai #financialfreedom

TIMESTAMPS

0:00 Intro

0:55 Why VIX calls won't save your iron condors

5:18 CTO vs CFO: which C-suite hire matters more

0945 Caller Dave on scalping leveraged ETFs vs futures

13:06 Charm heat map rebuttal for zero DTE trading

14:18 Decision from 40 years ago that now makes you laugh

16:54 Caller Cesare from Philly on favorite cult movies

22:09 Caller Jamie from Hawaii checks in

23:15 Will AI level the playing field for entrepreneurs

28:17 Caller Paul on U.S. debt doubling and S&P projections

31:39 Caller Eduardo on software stock drawdowns

36:54 Low-risk income strategies without short premium

40:21 Voicemail from Charles: what does Sol trade

42:09 Caller Wyatt on Warrior Trading scalping strategies

46:20 Will Lossdog go back on the road

48:12 How to use Lossdog software against salary consultants

52:10 Should you call back after a strong interview with no response

58:45 Market talk: Bitcoin, software selloff, gold reversal

The job market in 2026 continues to test candidates with automated screening, multi-round interviews, and radio silence after seemingly strong conversations. Meanwhile, AI is reshaping how entrepreneurs access information and build technology, potentially cutting team sizes from 200 people down to 20 or 30. With U.S. debt doubling roughly every nine years and now sitting at $40 trillion, the historical correlation between rising debt and rising equity markets raises real questions about what breaks first, or if anything breaks at all.

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

📧 [email protected]

🐕 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/

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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

Tom Sosnoff and Scott Sheridan break down why fundamental analysis doesn't give traders an edge, explain the truth about earnings plays and expected moves, and reveal their current short positions as markets hover near record highs. Plus, callers ask about prop firms, yen puts, and how to actually start trading options without losing money. Tom also explains why he's stuck holding PayPal forever after a blown earnings trade.

#lossdog #stockmarket #optionstrading #career #salary #financialfreedom

TIMESTAMPS

0:00 Intro

0:54 Why fundamental analysis doesn't work

7:52 Being short XYZ—what it actually means

9:12 Shorting stock vs selling calls vs puts

10:40 Tom's PayPal earnings disaster

12:02 New to options? Start here

14:25 Arthur calls: earnings trades have no edge

19:35 Lossdog Stablecoin coming in March

20:18 10-year yields and interest rate reality

24:33 Why Tom's always been short the market

29:38 Job offer anxiety—take it or stay safe?

34:16 Prop firm warning: fees and restrictions

37:26 Trading yen puts on regular expirations

39:04 Cubs jersey controversy

44:54 Caller: Mike from West Chester (PA)

47:40 Madison calls: how Lossdog scores intangibles

52:40 Employer side of Lossdog—will it be used against you?

54:39 Mark Burley's perfect game and the mitt debate

58:22 When traders thought algorithms couldn't replace them

The market hasn't had a real pullback since 2008, interest rates are stuck in a narrow range, and stocks like Micron and silver are making moves that blow past any technical or fundamental prediction. Meanwhile, traders still try to time entries with analysis that has zero edge. Tom and Scott have spent 40 years watching this play out—first in the pits, then building thinkorswim and tastytrade, and now with Lossdog. The constant? Nobody knows what's coming next, but the playing field stays level because of it. That's what makes markets tradable. This episode cuts through the noise on short-term trading, overnight risk, and why trying to outsmart price action usually backfires. If you're new to options, the advice here is simple: start small, trade liquid names, don't touch silver or natty gas, and forget about finding an edge in earnings.

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

📧 [email protected]

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Everyone has a number. Lossdog helps you know your number, and grow your number.

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