One Lucky Dog

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

Tom Sosnoff, Scott Sheridan, and Sol break down one of the real questions people are wrestling with right now: big corporation or startup — which one is actually right for you? They get into why the "safety" of large companies is often an illusion, what happens to entrepreneurial thinkers trapped inside corporate chains of command, and why a failed startup on your resume isn't the career killer most people fear. Live callers bring sharp questions on managing a call spread during a short squeeze on a volatile ticker, trading futures options in illiquid markets, and how to think about alternative investments when you're stepping way outside your comfort zone. Plus, Tom gives his blunt read on the Nasdaq's current rally and what rising complacency signals about where markets go next.

#lossdog #careerdevelopment #stockmarket #optionstrading #startupvscoorporate #investing

TIMESTAMPS

0:00 Intro and Tom's return from New York

3:16 New York pizza debate gets heated

12:30 New Fed chair hearing — the question nobody could answer

15:08 Nasdaq ripping: market update and Tom's trade thesis

15:45 Social media as a trading tool — contrarian vs. follower

21:13 Go big or stay small: the startup vs. corporate debate begins

24:42 Is startup culture too intimidating for entry-level workers?

26:06 Should you ask a startup about funding and runway?

28:24 Transitioning from a big company to a small one — why it usually fails

30:30 Does a startup failure hurt your resume or Lossdog numbers?

33:23 Quick market look

37:37 Investing outside your comfort zone: crypto, futures, and alternatives

41:15 Caller: managing a call spread during a CAR short squeeze

44:53 Caller David in Texas: surviving an entrepreneurial mindset in big companies

47:58 Caller Simon in New York: futures options liquidity and trading the active month

50:49 Online resources for learning to trade futures

51:41 Illiquid and non-traditional investments

53:25 Loan or stake in the venture

55:22 Rules for allocating capital into alternative investments

56:59 Rules of engagement when investing outside your comfort zone

1:00:20 Market talk

The startup versus corporate debate has never been more loaded. With mass layoffs still rattling workers at companies that once looked bulletproof, the idea that a big employer means job security is getting harder to defend — yet the uncertainty of startup life keeps plenty of talented people on the sidelines. At the same time, the question of how to build and protect wealth outside traditional investments is gaining urgency, as retail access to alternatives like private equity, venture funds, and tokenized assets slowly expands. Futures markets are seeing more retail participation, and the gap between what traders know and what they need to know about liquidity and position management is real. These aren't abstract topics — they're the decisions shaping careers and portfolios 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 wonderin...

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

📧 [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, Scott Sheridan, and Sol kick off the week with a tight hour covering the market's wild ride — what "riding the wall of worry" actually means, whether the 17-year buy-the-dip era is finally ending, and why Tom is fading this rally while it's still near all-time highs. On the career side, Tom breaks down three underrated moves for maximizing your professional value beyond your paycheck: investing in the company you work for, networking inside your own organization, and learning skills that have nothing to do with your job title. A caller asks how to value a private business when strategic buyers come knocking, and the crew gets into lump sum vs. dollar-cost averaging, delta-to-net-liquidity rules of thumb, and what Netflix's CEO departure on earnings day tells us about options flow.

#lossdog #stockmarket #optionstrading #careerdevelopment #salary #financialfreedom

TIMESTAMPS

0:00 Intro and Sol's birthday

5:07 Show preview: wall of worry, career, trend trading

9:53 What "riding the wall of worry" really means

14:36 Is the buy-the-dip era finally over?

15:35 Beyond your paycheck: career maximization

16:03 Why you should invest in your own company

17:50 Networking inside your organization

20:27 Learn skills outside your comfort zone

22:40 Speak up, show up, grab opportunities

24:33 Think it, say it — there's no risk in having ideas

29:08 Live market update: S&P, NASDAQ, gold, oil

31:51 Caller Simon: how to value your private business

39:50 Trend following vs. fading the move explained

47:07 Lump sum vs. dollar-cost averaging — what studies say

51:37 Delta-to-net-liquidity rule of thumb

55:46 Market wrap: VIX, bonds, Netflix, Microsoft

56:53 Netflix CEO departure and what the options flow showed

Markets right now sit at a crossroads that makes most of the conventional wisdom feel shaky. The post-2008 "just buy the dip" playbook has worked for nearly two decades, but 2026 is looking like a year where that muscle memory could cost people real money — not because markets are collapsing, but because the snap-back rallies are getting more violent and the risk of extended chop is rising. Meanwhile, the career conversation is just as timely: with layoffs still grinding through white-collar sectors and AI reshaping what employers actually value, the workers who come out ahead are the ones who've made themselves harder to replace — not just through their core role, but through equity ownership, cross-functional visibility, and a skill set that keeps expanding. Tom and Scott built two of the most influential trading platforms in history partly because they kept asking questions outside their lane, and this episode is a direct transfer of that mindset.

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 act...

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

Tom Sosnoff, Scott Sheridan, and Sol close out the week with two meaty topics: the real rules of compensation negotiations (what to say, what never to say, and when drawing a line in the sand gets you shown the door), and how to actually trade earnings when volatility has been cut nearly in half. Tom breaks down why low volatility changes your earnings edge—your probability of profit stays the same, but how much you can make gets crushed—and shares his current positioning going short S&Ps and Nasdaq futures after calling the week's straight-up rally. The dog pound fires off sharp questions on call spread probability, strangle strategy under compressed IVR, and how to handle positions when earnings are on the horizon. Plus: Lossdog announces 2,000 new software users added in one day, an agentic AI feature dropping next week, and a surprise birthday shoutout to Sol.

#lossdog #salarynegotion #earningsseason #optionstrading #stockmarket #careerdevelopment

TIMESTAMPS

0:00 Intro and Lossdog software update

1:04 Agentic AI feature and roadmap preview

2:13 Market recap: Tom calls the week right, now going short

2:39 Short positions: S&Ps, Nasdaq futures, call spreads

5:24 Show agenda: compensation talks and earnings season

11:21 Will you trade differently during earnings season?

13:17 Earnings results are nearly 50-50 going back 25 years

14:42 The good, the bad, and the ugly of compensation talks

17:23 Devs, entitlement, and the negotiation mindset

18:01 Rule 1: Negotiate from strength — know your value

20:52 Rule 2: Never draw a line in the sand

23:14 Rule 3: Don't bring up other people's salaries or other offers

27:55 How to get more leverage as an employee

28:51 Over-deliver and expand your role

30:09 Don't be dissappointed if you don't get it all at first

31:30 What happens when raises keep getting delayed

32:19 Mid-show market look

33:57 Navigating earnings in a low volatility environment

35:06 High vol vs. low vol: how earnings premium works differently

36:38 Are earnings trades more risky or less risky when vol drops

37:53 Low vol rule: extend your duration to pick up synthetic vol

39:01 Should I hold the position through earnings?

42:00 Dog pound Q: Strangles into earnings when IVR is compressed

42:50 Earning at horizon, back away from opening new trades?

46:42 Will earnings impact the broad market?

49:28 Dog pound Q: How to calculate probability of profit on a call spread

52:27 Dog pound Q: VIX contraction — which strategies to use this cycle

56:04 Dog pound Q: Does a debit call spread have negative probability of profit

57:26 Market Talk

With volatility down nearly 50% from its recent spike and earnings season kicking off, traders right now are caught between two forces: the urge to stay active and the reality that low premiums compress how much you can actually make. That tension—same probability, smaller payoff—is one of the least-talked-about dynamics in retail options trading, and it shows up hardest during earnings. On the career side, most people think salary negotiations are about confidence or timing, but the real edge is simpler: knowing your actual market value before you walk into the room. That's the gap Lossdog is built to close. Between AI-driven market swings, a job market still sorting itself out post-tariff volatility, and the growing pressure on employees to advocate for themselves without a clear benchmark, both topics on today's show land exactly where people are right now.

ABOUT ONE LUCKY DOG LIVE! / LOSSDOG

One Lucky Dog LIVE! is your daily wake-up call...

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

📧 [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://loss...

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.

It's tax deadline week and April expiration — and Tom Sosnoff, Scott Sheridan, and Sol break down what that actually means for traders right now. The S&P is within 1% of all-time highs, VIX is back to 18, and the market has climbed a wall of worry like it's nothing. On the career side, Tom and Scott get into the real red flags around job hopping, whether a lateral move can actually be a power move, how long you should give a new job before bailing, and what to do when you get an offer you love in a city you don't. A caller from Orlando asks how to get short inside an IRA account — and gets a straight answer.

#lossdog #jobchange #impliedvolatility #optionstrading #careertips #stockmarket

TIMESTAMPS

0:00 Intro and show topics

1:00 Tax time — penalties, procrastinating, and quarterly estimates

4:08 rolling out to 2k more users

5:26 Does tax season affect the stock market?

7:30 April expiration historically bullish — the data

8:09 PDT rule SEC decision update

8:45 Live market update — S&P near all-time highs

11:13 Buy the rumor, sell the news

11:40 Job changes: how many is too many?

14:32 Can a lateral move be a positive career step?

16:15 Got an offer out of state you're turning down — will you regret it?

19:19 Should you always be looking for new career opportunities?

20:51 How long should you give a new job before leaving?

24:25 Work-life balance debate — Tom vs. everyone

27:38 Market check — Nvidia, Meta, crypto all surging

28:58 Layoffs and job changes — does it look bad on your resume?

29:48 Monster rally - market always wins

30:43 Trading in high implied volatility — is there such a thing as too much?

34:53 Does high vol always mean larger expected moves and higher option prices?

37:57 Trading Bloom Energy - up 20%

39:27 What's the downside of high IV?

41:48 Opportunity and volatility have a positive correlation

44:20 Does high implied vol always mean a lower cost basis?

47:05 Does level 2 data help predict volatility direction?

48:57 Market Talk

52:41 Caller: How to get short inside an IRA account

The job market in 2026 is still absorbing waves of layoffs from tech, finance, and media — which means millions of people are navigating involuntary career pivots, not just voluntary ones. At the same time, a generation of workers raised on LinkedIn hustle culture has normalized job-hopping in ways that hiring managers like Tom and Scott see as a genuine red flag. On the markets side, implied volatility — often misread as a threat — is one of the most misunderstood concepts in retail trading. The VIX spent years being called the "fear index," which conditioned investors to hide when it spiked, exactly the opposite of what the data supports. Understanding that volatility and opportunity are positively correlated isn't just a trading edge — it's a mindset shift that separates reactive investors from prepared ones.

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...

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

Tom Sosnoff, Scott Sheridan, and Sol kick off the week with a packed show covering the career attributes that actually move the needle—problem solving, decision making, public speaking, and leadership—plus a real conversation about why product indifference makes you a stronger trader. They get into "news you can't use," break down why opportunity in efficient markets is completely random, and share what that means for how you build and manage a portfolio right now. Markets are in a wild spot—S&P sitting three percent from all-time highs in the middle of geopolitical insanity—and the guys share exactly where they stand and what they're watching heading into April expiration week.

#lossdog #careerdevelopment #optionstrading #productindifference #stockmarket #salaryadvice

TIMESTAMPS

0:00 Intro & Chicago weather check

1:29 Cancel crash: markets open down, now up

2:38 Masters recap and Rory McIlroy debate

4:34 Cubs, Bulls standings talk

6:00 Market update: S&P, Nasdaq, crude oil

7:25 Fix-a-flat, EVs, and spare tires

10:24 Show preview: careers, trading, Lossdog waitlist

11:10 News you can't use

15:49 J-Powell and who can actually move markets

17:04 Trump, the Pope, and political noise

18:47 Career attributes: problem solving is #1

21:31 Is decision making a measurable career skill?

24:51 School vs. real-world experience

26:45 Public speaking: how necessary is it really?

29:14 Developing leadership skills

32:25 Market recap at 9 : 32 AM

34:49 Product indifference: trade everything explained

38:21 Reasons not to trade a certain product: size, leverage, liquidity

40:58 Primary reason to trade everything: opportunity is random

45:16 Do all asset classes use the same derivative models?

47:22 Correlation risk vs. diversification risk

52:17 Market Talk: April expiration, taxes, Sol's birthday

56:11 Buy the rumor, sell the news market thesis

59:53 S&P targets, what to short and what to hold

The job market in 2026 is forcing a reckoning with what skills actually translate to income—and it's not just your degree. As AI reshapes entry-level roles and companies restructure at pace, attributes like problem solving, decisive action, and the ability to lead under pressure are becoming the real differentiators between people who advance and people who plateau. On the trading side, product indifference isn't just a philosophy—it's a risk management strategy. With volatility elevated, geopolitical headlines moving markets intraday, and April expiration historically one of the year's strongest cycles, knowing how to stay flexible across asset classes—stocks, futures, options, crypto—is how you stay in the game when opportunity shows up randomly, which it always does.

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...

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

Tom, Scott, and Sol open today's show with oil back over $100, a ceasefire falling apart, and a stock market that somehow doesn't care. From there, the conversation gets personal: startup vs. corporate vs. self-employed — which path actually fits you, and is corporate "stability" a real thing or just a story people tell themselves? Tom says it's a flat-out myth. Scott isn't so sure. Then the show shifts to the keys to opening a new trade — liquidity, implied volatility, price extreme, position sizing, and knowing your pre-trade probabilities before you ever click the button. The episode also touches off a sharp debate on insider trading and whether markets would actually be better off if every restriction was lifted.

#lossdog #careerdevelopment #optionstrading #stockmarket #jobmarket #financialfreedom

TIMESTAMPS

0:00 Intro

6:35 Show format and Lossdog update

7:29 Oil over $100 and market reaction

11:19 Today's agenda overview

13:30 "Couldn't Be More Wrong" segment

16:49 Startup vs. corporate vs. self-employed: Best available?

20:44 Star-up or Self employed is easier when you're older

23:36 Personality and education fit for corporate?

24:57 Do I follow in my parent's steps career wise or do my own thing

26:58 Is corporate stability a myth?

29:35 Quick look at the market

33:20 Keys to opening a new position: Control what you can

37:10 Don't confuse opportunity with fixed expectations

39:05 Interactive Brokers CEO on insider trading

40:12 Insider trading debate — where's the line?

46:21 Trading keys recap- IV, liquidity, price extreme

48:20 Position sizing and controlling conviction

52:28 Pre-trade probabilities explained

54:24 Lossdog platform update and AI agents

56:57 Market Talk: S&P, NASDAQ, gold, Bitcoin

Layoffs at major companies, rising oil prices, and an unstable geopolitical picture are forcing a lot of people to ask hard questions about job security and financial independence right now. The old idea that a corporate career equals stability took real hits after 2008 — and it keeps taking them every time a Disney or an Amazon announces another round of cuts. Meanwhile, retail traders navigating wild swings in oil, bonds, and equity vol need a sharper framework than just "follow the news." The conversation on this show connects both of those threads: how you build a career worth having, and how you trade in markets that don't care what you think is going to happen.

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 num...

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, Scott Sheridan, and Sol kick off a whippy market morning with S&Ps, gold, oil, and Apple all moving hard — then get into what actually matters: are companies looking up your public profile to figure out how little they can pay you? Tom and Scott break down how the Lossdog software calculates your real market value using government salary data, education, location, and work experience — and why knowing your number is the first step to negotiating a better one. A caller named John shares a real update: he used a competing job offer to negotiate a 7% raise and stayed put. Then Tom and Scott go deep on scalping — what it actually is in 2026, why futures beat options for short-term trades, and how to set profit and loss targets based on the day's range.

#lossdog #salarynegotiation #knowyourworth #scalping #stockmarket #optionstrading

TIMESTAMPS

0:00 Intro and market open recap

0:44 Last day of civilization?

1:13 Today's show preview: whippiest days, salary, scalping

6:16 Market review

11:10 The whippiest trading days ever

18:25 Knowing what you're worth: Are companies using your profile to lowball you?

21:57 Caller Larry: how does Lossdog value skilled labor?

27:22 Does knowing your worth matter without leverage?

31:09 Could knowing your value be a distraction?

33:34 Should salary transparency be good or bad?

36:08 What is scalping and how is it defined in 2026?

40:29 Why futures and stocks beat options for scalping

43:27 Is a true scalp only an intraday trade?

44:10 Caller John: he negotiated a 7% raise and stayed

46:06 Caller Josh: grateful for the lessons and keepin' it Chicago

50:00 Best market conditions: range-bound or one directional for scalping

52:03 How to set profit and loss targets for scalps

56:34 Market Talk

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.

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Tom Sosnoff, Scott Sheridan, and Sol kick off a new show format on One Lucky Dog Live!—and today's mix hits hard: are companies deliberately using the weak job market to slot overqualified candidates into internships instead of real jobs? Tom and Scott share exactly how they ran internships at tastytrade, what made them valuable (hint: about 25% turned into full-time offers), and why the most important thing you get from an internship isn't the job title. Then it's into buy the dip—when it works, what vehicle to use, why it's outperformed selling the rally for 20 years, and whether 2026 might finally be the year that streak breaks. Plus a live market update with Apple leading, VIX at 25, and Tom's top premium-selling plays in gold and crude oil right now.

#lossdog #careerdevelopment #internships #buyhedip #stockmarket #optionstrading

TIMESTAMPS

0:00 Intro

0:07 New show format explained

0:42 Best Day Ever — weekend stories

5:15 Scott's Noma LA pop-up experience

9:43 Morning market update — S&P, Nasdaq, Bitcoin

14:38 Best Day Ever — pilot rescue, Final Four, White Sox

20:25 Internships segment begins

20:51 Are companies exploiting overqualified candidates?

26:33 How to network and land an internship

35:43 How much follow-up is too much?

36:15 Do employers actually value internships?

38:19 The real reason to do an internship

41:20 Buy the dip — strategies and vehicles

45:15 Do you only buy the dip during sell offs?

48:11 What is your preferred vehicle for BTD?

49:50 Why does BTD seem to work better than sell the rally

53:03 Is buy the dip just an oversold hunch?

57:52 Market Talk: VIX, gold, crude oil plays

The job market in 2026 looks nothing like it did five years ago. Hiring has slowed enough that companies now have serious leverage—and some are using it to fill roles with internships instead of entry-level positions, paying less and offering no benefits in the process. For anyone navigating this as a job seeker, understanding how to read that dynamic (and whether to play along or push back) is genuinely useful information. On the markets side, the buy the dip playbook has worked almost without interruption since 2008—but the math behind why it works is something most retail investors never actually see: the market has been up nearly 58-60% of trading days over the last two decades, a meaningful shift from the historical 53-47 split that used to make stocks a much harder sell as an asset class. Whether that edge holds through a volatile, tariff-rattled 2026 is the real question worth watching.

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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