One Lucky Dog

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

Tom Sosnoff and Scott Sheridan break down positive drift—what it actually means and why you should be applying it to every part of your life, not just your portfolio. They share five concrete ways to boost your career fast, from treating your role like a business to why "it's not my job" is the phrase that ends careers. Tom also walks through the mechanics of rolling and adjusting positions, including the IVR rules most traders ignore, with live trade ideas on Netflix puts, SMH call spreads, the South Korea ETF, and SOXS covered calls. Callers weigh in on whether most active traders are net short right now and whether regulatory changes at the SEC and CFTC could shake market confidence.

#lossdog #optionstrading #careertips #stockmarket #financialfreedom #salary

TIMESTAMPS

0:00 Intro and banter

9:37 Market overview: SPX, NASDAQ, crypto, big movers

13:31 Show agenda: positive drift, career boosts, rolling positions

15:53 Positive drift explained: what it is and should you act on it

18:19 Lossdog Trades of the Week intro

19:02 Netflix puts trade idea (July 75/80 puts)

20:36 SMH semiconductor ETF call spread

22:03 South Korea ETF (EWY) put spread setup

24:09 SOXS covered call trade idea

29:00 Single most important career boost beyond learning

34:06 Treat your role like a business you own

38:59 Caller Madison: are most traders net long or short?

43:44 Caller Daniel: SEC/CFTC regulatory changes and market confidence

47:43 Rules for rolling and adjusting options positions

51:12 Dog Pound: covered call getting crushed — what to do

53:33 The best and worst ways to say no to your employer

56:37 Final market Talk

Career growth and market confidence aren't as separate as they seem—both come down to the same idea: positive drift. The principle that things should steadily get better over time underpins why investors take risk in equities, why active traders roll losing positions instead of panicking out, and why the best employees treat every task like it belongs to them personally. With options volatility remaining elevated and the PDT rule officially lifted as of today, new dynamics are opening up for retail traders who've been boxed in. Meanwhile, the broader debate about whether deregulation at the SEC and CFTC strengthens or weakens long-term confidence in U.S. markets is one that won't be settled until the next real correction hits.

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 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, Scott Sheridan, and Sol get into it on a packed Tuesday: whether the AI narrative is the single biggest risk to the stock market right now, and why the SpaceX IPO might be the actual trigger nobody's talking about. Scott walks through his trades of the week — Micron, Netflix, and Japanese Yen. Tom makes the case that Michael Saylor is a single point of failure for Bitcoin and lays out exactly what a blow-up could look like. A caller phones in with a sharp theory: when Saylor gets fully discredited, that's your Bitcoin buy signal. Then Tom breaks down how to get out of a trading slump — reduce size, narrow your universe, stop chasing — plus a real talk on whether an MBA is actually worth the time and money in 2026.

#lossdog #optionstrading #stockmarket #bitcoin #investing #career

TIMESTAMPS

0:00 Intro and morning banter

5:38 Market open: Nasdaq, Bitcoin, gold rundown

6:23 Michael Saylor sold Bitcoin — why it matters

10:57 Today's show agenda

12:39 Is AI overexposure the biggest market risk?

15:33 SpaceX IPO and the Nasdaq 100 trade everyone's making

20:06 Scott's Trades of the Week: Micron, Netflix, Yen

24:36 Quick market look

28:23 Caller Paul: options assignment risk after market close

32:09 Is an MBA worth the time and money?

40:29 Caller Aaron: Saylor discredited = Bitcoin bottom signal

43:58 Market look

45:09 How to break out of a trading slump

50:55 Perpetual futures outside crypto: CFTC opening the door

54:14 Market Talk

The S&P 500's 20% rally in roughly two months has traders asking a real question: how much of this is AI momentum, and how much is just the market riding a wall of worry with nowhere else to park money? The SpaceX IPO is shaping up as a potential inflection point — a massive event that index funds are being forced to front-run, which could turn buy-the-rumor into a sharp sell-the-news. Meanwhile, Michael Saylor's concentrated Bitcoin position remains the clearest single point of failure in crypto — a dynamic that echoes historical blow-ups like Long-Term Capital Management and Bear Stearns, where capitulation marked the bottom. And for professionals navigating all of this, the MBA debate is more relevant than ever: with AI reshaping hiring, credentials that signal business fluency and networking depth carry real weight in a tighter job market.

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 break down why AI CEOs are suddenly changing their tune — and whether you should buy the new narrative. They get into the biggest career hurdles people face (imposter syndrome, burnout myths, golden handcuffs, the "daughterhood penalty"), walk through the AI Trades of the Week in Uber, AMD, Coinbase, and Robinhood, and tackle one of trading's most brutal realities: what do you do when you do everything right and the market still punches you in the face? A caller from Jersey asks the exact question on every options trader's mind, and Tom shares exactly how he's using AI — including Claude — in his own trading right now.

#lossdog #optionstrading #aiinvesting #careergrowth #stockmarket #tradingstrategy

TIMESTAMPS

0:00 Intro and sports talk

4:32 Market check: S&P, Nasdaq, Bitcoin, VIX

8:26 AI in trading: question of the day

9:00 AI CEOs walking back the doom narrative

10:45 Good billionaire vs. bad billionaire

12:35 Show agenda: career hurdles and market discipline

13:30 Market look

22:28 AI Trades of the Week: Uber, AMD, HOOD, Coinbase

27:21 Caller Loki: handling outlier moves against you

31:01 Biggest career hurdles explained

32:20 Imposter syndrome, indecision trap, fear of failure

36:26 Longevity as the real key to success

40:34 Market recap

41:20 Trading discipline when markets go irrational

45:34 How one big loss wipes out 21 small wins

50:51 How Tom and Scott actually use AI in their trading

56:22 Market Talk and is there ever a time to trade the VIX?

57:30 9 insider tips for active investors — dropping now

AI is no longer a futuristic concept in finance — it's actively being embedded into trading platforms right now, and the conversation around its impact on jobs and markets is shifting fast. Meanwhile, the 2026 job market continues to challenge professionals at every level, from early-career workers battling imposter syndrome to senior employees caught in golden handcuff traps and stifling corporate bureaucracy. On the trading side, persistently elevated implied volatility across multiple expiration cycles has created brutal conditions for premium sellers — exactly the scenario Tom and Scott break down in real time here. Understanding how irrational market behavior operates, why standard deviation moves matter for position sizing, and how to manage discipline when the market refuses to cooperate are increasingly essential skills whether you're a full-time trader or a part-time options seller.

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

E...

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 get into one of the most misunderstood questions in trading: who's actually moving markets overnight, and why those moves sometimes dwarf what happens during regular hours. They break down CFDs, global futures flow, and why there's no wizard behind the curtain. Then the show shifts to two big career questions — whether your industry or your specific job matters more for long-term pay and stability, and whether you should ever manage money for friends or family after some trading success. Tom shares a real story from 2008 that cost him, and gets specific about the legal, emotional, and relationship risks most people never see coming. Sol and the chat keep the energy honest throughout.

#lossdog #optionstrading #stockmarket #careerdevelopment #financialfreedom #investing

TIMESTAMPS

0:00 Intro and puppy sleep deprivation

3:36 Morning market recap — Nasdaq, Micron, gold, Bitcoin

6:50 Today's show agenda and topics preview

8:50 Who's behind the big overnight market moves?

10:00 What is a CFD and why it's illegal in the US

12:02 No wizard behind the curtain — global market forces explained

15:39 Quick market recap

18:20 Scott's trades of the week — Nokia, Intel, Netflix setups

23:45 Market look

25:16 Dog Pound: what to do when competition shows up

27:00 thinkorswim and the Small Exchange story

29:20 DP Poll: INTL and SIL trades

29:32 Market look - Nasdaq will scare the children

30:39 Industry vs. job — which one actually matters more for your career?

37:44 More market

38:53 Should you manage other people's money after trading success?

47:32 Real risks of managing others' money — legal, emotional, financial

54:11 Market Talk: AI rally sustainability

The question of who moves markets after hours sounds like a conspiracy theory — but the answer is genuinely just global retail and institutional flow, CFD brokers in London, and tens of millions of traders from India to Eastern Europe all watching the same screen. Meanwhile, the job market debate between choosing a hot industry versus a role you actually master is one of the most consequential decisions early-career professionals face in 2026, especially with AI reshuffling which industries pay a premium and which ones are quietly shrinking headcount. And the "should I manage money for people I know" question is a classic trap: the psychological weight of someone else's losses, the legal exposure, and the relationship damage potential are things most successful traders learn the hard way — not from a book. This episode covers all three with the kind of bluntness you don't usually get from people who've actually lived it.

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 10-11...

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

Tom Sosnoff, Scott Sheridan, and Sol are back post-Memorial Day weekend to a market that feels like it's living in a different dimension from everyone else. The Nasdaq crossed 30,000, call skew appeared in S&P options for the first time in years—a rare warning sign that the market is pricing in explosive upside velocity—and yet the class of 2026 is graduating into the toughest entry-level job market in four years. Tom walks through his four trades of the week including a bearish semiconductor play, a SPY call spread, a crude oil iron condor, and a Marvell earnings setup. Then Scott gets into a practical, no-nonsense breakdown of exactly how they find new trades. Callers weigh in on earnings trading heuristics, the SpaceX IPO, and what happens to space stocks after the big listing.

#lossdog #optionstrading #stockmarket #careerandfinance #spacex #aijobs

TIMESTAMPS

0:00 Intro and post-Memorial Day check-in

3:07 Market open recap: Nasdaq crosses 30,000

4:33 Show's topics

7:28 Markets update: gold, oil, bonds, and Bitcoin

14:49 DP: Relationship between Brent Oil and WTI

15:40 Call skew in the S&P 500 explained

16:30 Is call skew a red flag right now?

21:20 Quick look at the market

23:03 Trades of the week: SOXS, SPY, crude oil, MRVL

30:37 Market recap

30:47 Class of 2026 booing AI commencement speakers

32:04 New grad unemployment at a 4-year high

33:40 Goldman CEO: AI will create as many jobs as it takes

42:10 DP Poll: 42% are equally excited and concerned for AI

42:24 Market look

42:50 Caller: earnings trading heuristics with Mitch

44:51 Caller: SpaceX IPO and trading strategies with Ty

48:30 DP: Will space stocks ride the wave with SpaceX

49:40 How to actually find new trades

51:30 Using price and IVR to spot opportunities

55:20 Engage with any ideas you find and own your trade

59:50 Market Talk

The Nasdaq hitting 30,000 while new grad unemployment sits at a four-year high tells you almost everything about the economic moment we're in right now—the market and the labor market are running on completely different tracks. Entry-level job seekers are dealing with the tightest hiring environment since before the pandemic, a growing sense that AI is a scapegoat for layoffs companies were planning anyway, and degrees that feel less certain than they did four years ago. At the same time, options markets are flashing something genuinely unusual: call skew in S&P index options, which happens maybe 5% of the time and historically signals that the market perceives the next big velocity move is to the upside, not the downside. Whether you're navigating that market with options strategies or navigating a job market that doesn't reward linear career thinking the way it used to, the underlying question is the same—do you actually know what you're worth, and are you positioning yourself correctly?

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.

<...

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

Tom Sosnoff and Scott Sheridan fly solo today — no Sol, just straight talk. They kick things off breaking down the NVDA earnings non-event and why volatility won't come in, then share four live Dog@AI trade ideas: Uber puts, TLT puts, an IWM iron condor, and a Netflix strangle. The career killers segment gets real fast — five behaviors that quietly cap your earnings and end careers, from blaming others to indecision loops. They close out with a practical guide to getting started in futures markets without blowing up your account.

#lossdog #careertips #optionstrading #stockmarket #futurestrading #salarynegotiation

TIMESTAMPS

0:00 Intro

0:44 NVDA earnings recap and market open

6:45 Live market overview: bonds, S&P, NASDAQ

10:30 Question of the day: will vol rise or fall post-earnings?

11:30 Show's topics

12:46 Volatility discussion

17:20 Favorite quantum exposure

20:28 Dog-it AI trade ideas: Uber, TLT, IWM, Netflix

25:25 Trades recap

26:09 Caller Brooklyn: how IPO shorting actually works

29:54 DP: Dog-it AI coming features

31:32 Career killers — 5 things that end careers

36:50 Career killers recap

37:40 Mid-show market check

39:48 Caller: why after-hours selloffs matter more at 4 - 4 : 30 PM

43:15 Why Scott calls his wife "the six"

47:22 Futures market primer: micro contracts and sizing

53:52 Futures trading 101 recap

54:49 Dog Pound poll: do people share recipes? - 83% say yes

56:20 Market Talk and holiday schedule

Volatility stuck in the high teens and low 20s even as most of the big earnings are behind us — that's not a coincidence. Elevated VIX with markets near record highs reflects a market that hasn't fully made up its mind about the path forward, and that tension is exactly what makes premium-selling setups like iron condors and short strangles worth watching right now. On the career side, the five killers here aren't random — they map almost perfectly onto what behavioral economists call attribution bias, commitment problems, and coordination failures, three of the most well-documented reasons high-potential employees plateau or wash out. And the futures discussion matters more than ever: retail participation in futures and futures options has grown sharply in recent years, and micro contracts have removed the biggest barrier to entry — contract size — making it genuinely accessible to self-directed traders for the first time.

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

Tom, Scott, and Sol kick off Wednesday with NVIDIA earnings on everyone's mind — and Tom already has a strangle on. Before the close, they walk through the Lossdog Nation trades of the week (Snowflake, Marvell, Robinhood, and silver), break down why undefined risk trades like strangles often beat iron condors on probability and credit, and explain what VIX backwardation actually signals in a conflict-driven market. On the career side, the show gets into a real one: what do you do when you genuinely don't know what you want to do with your life? Sol walks through a practical self-audit framework — shifting from big-picture career anxiety to short-term project thinking — and Tom and Scott share why changing paths multiple times isn't failure, it's just how careers actually work. Callers weigh in on Solana, the best time of day to trade, and more.

#lossdog #optionstrading #careerdevelopment #nvidia #stockmarket #vix

TIMESTAMPS

0:00 Intro and Memorial Day weekend banter

3:54 Market check — S&P, Nasdaq, NVIDIA pre-earnings

7:10 NVIDIA earnings strangle trade breakdown

11:18 CRRS options spread

12:30 Show's topics

13:21 Caller: Mitch question about solana

15:50 Question of the day: is there a best time to trade?

19:02 Lossdog Nation trades of the week

19:20 Trade idea: Snowflake earnings strangle

20:49 Trade idea: Marvell iron condor

22:21 Trade idea: Robinhood puts

23:01 Trade idea: silver strangle

24:17 Caller: Best time of day to trade

26:01 DP: what's your trade for NVDA earnings

27:32 Career segment — I don't know what I want to do

28:02 Career self-audit: list your strengths and constraints

29:38 Shift from career thinking to project mentality

31:40 You can pivot and don't have to figure it out all at once

36:10 Market Look

38:11 Undefined risk vs. defined risk trades explained

41:26 NVIDIA strangle as a real-time example

46:18 Sol's question: VIX cash vs. VIX futures explained

48:36 VIX backwardation and what it signals right now

50:04 Market Talk: bonds, chips, and what to watch into close

Career confusion isn't a personal failing — it's practically a structural feature of the modern job market. With AI reshuffling entire industries, white-collar layoffs running hot through 2025 and into 2026, and the traditional "pick a lane and stay in it" model quietly falling apart, more people than ever are asking the same question Sol frames on today's show: what do I actually want to do? Research consistently shows that most Americans change careers — not just jobs — multiple times across their working lives, and the workers who treat skills development as an ongoing project rather than a fixed destination tend to adapt faster and earn more over time. On the trading side, the strangle-versus-iron-condor question is one that trips up options traders at every level: defined risk feels safer, but the math on probability of profit and credit collected often tells a different story — especially in high-volatility environments like the one the market is sitting in right now, with the VIX elevated and in backwardation heading into a major earnings catalyst.

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'...

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

Tom Sosnoff, Scott Sheridan, and Sol open with chip stocks doing something wild — AMD swinging hard before the open — then get into bonds teetering at dangerous levels and what a VIX that won't move actually signals. The question of the day lands right at the intersection of career and money: does actively trading help or hurt you outside of finance? The answer is yes, it helps — and Tom and Scott break down exactly why. Scott walks through four trades of the week including Nike puts, a Baba put spread, and an AMD strangle adjusted for a $25 drop. Then the real conversation: fear of success, imposter syndrome, losing friends on the way up, and how to build a modern portfolio for a world with elevated interest rates — including the 30/30/40 framework, treasury ETFs, stablecoins, and why staying non-correlated quietly cuts your risk by 30%.

#lossdog #optionstrading #careerdevelopment #salary #investing #stockmarket

TIMESTAMPS

0:00 Intro and AMD's wild open swing

4:33 The 2010 flash crash — where Scott was

8:09 Bonds at dangerous levels, VIX not moving

13:20 Homeschooling debate from the dog pound

15:10 Show agenda and question of the day

18:11 Does active trading help your career?

23:49 Scott's trades of the week: Nike, Baba, AMD, QQQ

27:23 Fear of success and breaking the success trap

29:14 Imposter syndrome at every career level

32:11 Losing friends because of your success

37:30 Building a modern portfolio today

45:44 Cash segment: treasuries, ETFs, and stablecoins

49:53 The 30/30/40 portfolio framework explained

In 2026, fear of success gets less airtime than fear of failure — but it quietly stops more careers and holds back more real earning power than most people admit. Meanwhile, the question of whether trading belongs outside of finance isn't just about money; it's about whether financial literacy is a career skill or a distraction, and Tom and Scott argue it's one of the most transferable edge advantages a non-finance professional can build. On the portfolio side, interest rates staying elevated changes everything about allocation logic — the old 60/40 model doesn't hold up the same way when cash is actually earning something, stablecoins are gaining regulatory clarity, and stocks are just off all-time highs. The 30/30/40 framework they walk through here is a genuinely different way to think about where capital should live right now.

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://lossd...

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 get into the real case for AI in your trading portfolio — and it's not the scary version. They walk through why AI has zero downside for retail traders, how it levels the playing field against firms like Citadel, and what the new Lossdog prediction engine (Nostradagus) actually does. Plus, a raw career conversation on self-employed versus working for a company, with real stories from the thinkorswim founding era. They also cover four specific trades of the week — Boeing, gold, ZN puts, and FXI — and close with a sharp take on why the new Fed chair may already be set up to fail, with yields at multi-year highs and a 35% market-implied chance of a rate hike in 2026.

#lossdog #optionstrading #stockmarket #aitrading #careerdevelopment #federalreserve

TIMESTAMPS

0:00 Intro and weekend recap

06:58 Market open — S&P, Nasdaq, key stocks

08:25 Bond yields at multi-year highs explained

09:13 Show's topics and Fed Chair discussion

14:10 Trades of the week: ZN, gold, Boeing, FXI

19:45 Trade recap and viewer poll results

21:49 Career talk: company job vs. self-employment

27:19 Why self-employment beats a paycheck (for some)

29:57 The thinkorswim origin story

31:15 Market look

33:19 DP question: profitable option strategy above current range

34:23 Will AI help or hurt your trading results?

38:02 AI and outlier risk management

40:24 AI monitoring positions 24-7 — game changer?

42:05 Lossdog's Nostradagus prediction engine explained

45:10 AI will optimize trade adjustments

47:18 Viewer Q: contractor to full-time — worth it?

50:24 Market Talk: choppy inside day

53:03 Fed rate hike odds and what it means for stocks

53:35 New Fed chair Kevin Warsh — set up to fail?

The job market and financial markets are both in a moment of genuine uncertainty — and this episode sits right at that crossroads. With bond yields climbing to multi-year highs and prediction markets now pricing in a 35% chance of a rate hike in 2026 (a dramatic reversal from the three cuts expected just months ago), the pressure on the Fed and on individual investors is real. Meanwhile, the debate between contract work and full-time employment is intensifying as companies gain more leverage in a cooling labor market, making the tradeoffs around benefits, flexibility, and income harder than ever to navigate. AI is accelerating all of it — not by replacing traders or workers, but by eliminating the inefficiencies that have always tilted the game toward institutions with more capital and more data. Understanding which side of these shifts you're on, and how to position yourself, is exactly the kind of clarity this show is built around.

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.

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

Tom Sosnoff, Scott Sheridan, and Sol break down five real reasons careers stall — from risk avoidance and blind loyalty to toxic environments to flying solo when you should be collaborating — and why fear of success might be a bigger career killer than fear of failure. On the trading side, Tom walks through the Dogged AI trades of the week, including index pairs, IBM puts, an Uber put spread, and a Japanese yen play, then gets into the math on managing winners versus losers: the 50% rule, the 2x loss optimal close, and why stop-loss points matter far less than most traders think. The show also features a live demo of Lossdog's new Nostradamus AI prediction tool, which pulls from prediction markets, betting sites, and crypto exchanges to generate trade ideas — free on the platform.

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

TIMESTAMPS

0:00 Intro and show welcome

1:14 Cubs, sports recap, and banter

6:20 Market open: S&P and Nasdaq check

7:10 Bond trade recap and Cisco's 26-year comeback

8:36 Dog-it AI and Lossdog platform preview

10:14 Show's topics

11:42 Question of the Day: who is "they" in markets?

18:16 Dogged AI trades of the week

22:53 Market recap

25:10 Why did my career stall?

26:05 Career stall reason 1: risk avoidance and fear of success

28:17 Career stall reason 2: toxic or comfortable environments

28:58 Career stall reasons 3-5: passivity, isolation, ambiguity

32:37 Market update: Nvidia hits record, VIX stays elevated

35:30 Nostradogus AI prediction tool live demo

39:29 Bitcoin new high by 2027? AI prediction result

42:02 Managing winners vs. losers: the 50% rule explained

43:40 The truth about closing losing trades

45:30 Do you ever take profits sooner

46:46 Optimal spot to cut your losses: 2x your risk

48:00 Adjusted trades: 50% or 21 DTE from original trade

49:48 Dog pound Q&A: strangles, MES short position advice

52:40 Cerebras IPO discussion

54:01 Market Talk: VIX at 18 with no sellers — what it means

Tom, Scott, and Sol record this episode against a backdrop where career stagnation is one of the most Googled professional topics of 2026 — and for good reason. With AI displacing traditional roles and companies quietly flattening management layers, the window for upward mobility is narrowing for workers who stay passive and wait for opportunity to knock. At the same time, options traders are navigating one of the strangest volatility regimes in recent memory: markets grinding to record highs while the VIX stubbornly refuses to come in, signaling that underneath the surface calm, institutional money is still buying protection. The emergence of AI-powered prediction tools like Lossdog's Nostradamus — aggregating prediction markets, betting exchanges, and crypto data in real time — points to a broader shift in how retail traders access research that was once reserved for hedge funds. Whether you're trying to figure out why your career flatlined or how to close a losing trade without guessing, the fundamentals here are the same: discipline, consistency, and knowing your number.

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 i...