One Lucky Dog

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Tom and Scott break down why retail investors can't actually "play" the SpaceX IPO the way they think — no shorts, no options, just hope. From there they get into where Bitcoin and ETH would need to land before they'd start buying again, what it really feels like to hit financial success for the first time, and the step-by-step mechanics of rolling options in a high-volatility market. They also react to Oracle laying off 10,000 people by email with one day's notice, field a sharp question about prediction market insider trading on Polymarket, and take calls from Jerry (trading micros vs minis on a $7,500 account), Alexander (Bitcoin intrinsic value and portfolio margin), and Wayne (Lossdog platform privacy). Sol shares an update on the Lossdog beta and what's shipping next week.

#lossdog #optionstrading #spacexipo #bitcoin #stockmarket #jobmarket

TIMESTAMPS

0:00 Intro

0:18 SpaceX IPO — how retail investors can actually play it

4:25 Crypto outlook — Bitcoin and ETH price levels worth watching

6:39 Handling financial success for the first time

12:09 Caller Wayne — Lossdog platform privacy and data security

15:09 Lossdog beta update — what's launching next week

16:22 Caller Alexander — Bitcoin intrinsic value and portfolio margin

26:00 Zero DTE — which underlyings actually work

26:42 How to roll options — the 3-step breakdown

28:28 IVR explained — the right way to track implied volatility

30:20 Oil futures spread and Trump tariff market reaction

34:25 Managing positions in a sharp market reversal

36:29 Caller Arthur — structuring a long position in a beaten-down stock

46:15 AI trading tools — what's coming in under a year

46:43 Prediction markets and Polymarket insider trading problem

52:04 Lossdog going global — international access question

53:00 Caller Jerry — micros vs minis on a small account

58:12 Oracle lays off 10,000 by email — despicable or business as usual?

58:53 Market wrap — "violently unchanged"

With markets whipping around on tariff headlines and volatility sitting well above historical norms, knowing how to actually manage positions — not just open them — is the difference between staying in the game and blowing up. The SpaceX IPO conversation is a useful reminder that most "hot IPO" strategies available to retail traders are more limited than they appear, and that waiting for options liquidity is often the smarter play. Oracle's mass layoff-by-email is part of a broader 2026 tech labor story where even trillion-dollar companies are cutting headcount fast and cold, and the question of whether that's "on brand" or genuinely wrong matters for how workers understand their own job security. Prediction markets like Polymarket are growing fast, but the insider trading question raised here gets at a real structural problem — when trades move before major geopolitical events, the credibility of the whole asset class is on the line.

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 c...

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

Big day on One Lucky Dog Live! — the Lossdog platform officially launched, with the first 250 waitlist members getting their free crypto today. Tom Sosnoff and Scott Sheridan break down why the crude oil calendar spread is a trap most traders fall for, explain exactly where margin calls kick in (hint: it's the 5-delta option on your chain), and share the right ballpark for portfolio delta on a $100K account. The show also gets into stablecoin disruption of brokerage cash sweeps, why copy trading remains blocked in the U.S., the real risk AI poses to your career (it's not the technology), and what VIX above 30 actually signals for short positions. Callers share real questions on everything from micro futures instruments to whether mentorships actually work in business.

#lossdog #optionstrading #crypto #stockmarket #financialfreedom #career

TIMESTAMPS

0:00 Intro and show preview

1:57 Lossdog platform launch — first 250 users get free crypto

3:21 Bitcoin and crypto outlook — Scott vs. Tom

3:45 Crude oil calendar spread — why it's not a mean reversion trade

8:25 Cash sweeps, stablecoins, and the future of brokerage revenue

13:03 Caller Justin — tariffs, Liberation Day comparisons, and VIX above 30

17:55 How to stay fresh in your trading — managing stale positions

20:15 Margin calls explained — the 2 standard deviation rule

22:02 Portfolio delta — the right target for your account size

23:58 Caller Julio from Florida — copy trading, eToro, and U.S. regulations

33:39 Caller Solomon from Seattle — small account micro futures strategy

38:24 Caller Mark from Scranton — the confession: buying the wrong property

45:28 Logarithmic charts — why traders use them (and why Tom doesn't)

47:39 What's a good monthly return on trading?

51:00 The biggest AI risk: complacency, not the technology

55:15 Market talk — S&P rally, Nike at 52-week low, gold up big

Today's episode lands on the first day of the Lossdog platform rollout, right as markets are whipsawing through one of the most volatility-heavy stretches in years, with the VIX still running above 25 and traders trying to read whether the two-day rally is a real bottom or a pump-fake ahead of more tariff noise. The cash sweeps conversation is particularly timely — brokerage firms like Robinhood and eToro are already getting crushed in part because stablecoin and blockchain alternatives are starting to eat into the idle-cash revenue model that funds a huge chunk of their business. Meanwhile, the copy trading discussion reflects a real regulatory crossroads: the new SEC posture under the current administration has traders and fintech builders watching closely to see whether that model finally gets cleared in the U.S. And Tom's take on AI complacency — that the real danger isn't the tech itself but people outsourcing their thinking to it — cuts right to the heart of the Lossdog thesis: you can't know your number if you've stopped developing the skills that create 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 m...

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

Tom Sosnoff and Scott Sheridan break down what's actually on their personal watch lists after 25+ years of trading, why they both lead with futures before a single stock, and what happened when Tom visited the floor of the New York Stock Exchange and found out the specialists there can't even see CME futures prices. Caller Eduardo shares why he took a 50% pay cut to join a mutual fund — and why he doesn't regret it — plus gets a real answer on his 85-cents-on-the-dollar 401k match. The crew also gets into how long it actually takes a new trader to become profitable today versus the old floor-trading days, the real weight an MBA carries when you're interviewing, and whether quantum computing could ever crack Bitcoin security.

#lossdog #optionstrading #stockmarket #trading #careermoney #bitcoinnews

TIMESTAMPS

0:00 Intro

0:18 Tom & Scott's personal watch lists revealed

3:14 Inside the NYSE floor: no futures on the screens

8:59 Your mama's career advice — is she right?

11:25 Caller Eduardo: took a 50% pay cut, never happier

14:13 Eduardo's 401k — 85 cents on the dollar match

16:04 How long does it take a new trader to become profitable?

17:48 Is an MBA worth it? The real hiring truth

21:20 Gamma risk — do retail traders need to worry?

22:51 Do you ask job applicants if they trade?

27:04 When traders sell VIX futures

31:24 Scalping futures or options? Why futures work better

36:30 Iran's parliament's market advice — and the news vs. tape debate

39:58 Scaling premium collection: widen wings first

41:23 Positioning for another April low

48:28 Why platforms don't offer more than 4 leg spreads

50:39 Quantum computing and Bitcoin security

55:22 Market Talk: S&Ps, gold, VIX, big movers

The job market and investing landscape are both in a moment of genuine recalibration right now — and today's show sits squarely at that intersection. With elevated VIX levels, a market that's pulled back roughly 9% off highs, and a labor environment where workers are increasingly questioning whether a bigger paycheck is the whole story, the conversation between career fulfillment and financial strategy has never felt more relevant. Quantum computing stocks have cratered 60–70% off their highs even as the technology inches closer to real-world impact, creating the kind of uncertainty that rewards people who understand both the fundamentals and the market psychology. Whether you're figuring out how to size a trade, whether to chase an MBA, or how to think about your own professional worth, the throughline here is the same: understand your number, know your edge, and play for the next 30 years.

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...

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

Tom Sosnoff, Scott Sheridan, and Sol get into a live oil trade thesis—reversion to the mean or still room to run?—then break down why a VIX at 30 already prices in the chaos so you don't need a story to justify fear. Callers bring the goods: Dave from Colorado gets the real answer on short squeezes, Ricky from Phoenix asks about beaten-down brokerage stocks like Robinhood and Webull, and Larry from Myrtle Beach asks if dark pool data is actually worth following. The crew also gets into the job market power shift, angel investing for young founders, the Meta and Google addiction lawsuits, NYC's $30/hr gig worker pay proposal, and wraps with a live market read on what looks like a short-term bottom.

#lossdog #optionstrading #stockmarket #career #vix #financialfreedom

TIMESTAMPS

0:00 Intro

0:25 Oil reversion trade thesis

4:50 Trading through Trump tweets and market conviction

5:30 What VIX at 30 actually means for your position size

9:52 Is there a real metric for overbought and oversold?

11:30 Caller Dave: how short squeezes actually work

15:06 Currency strangles: 6E, 6J, or 6B?

17:39 Job market leverage: when does it shift back to workers?

20:02 Caller Ricky: brokerage stocks — Robinhood, Webull, IBKR, eToro

25:28 Angel investing and what young founders get wrong

32:10 Caller Larry: are dark pools worth tracking for retail traders?

37:34 FX risk when trading US markets from the UK

41:22 ES futures settlement and triple witching explained

44:28 Meta and Google addiction lawsuits: big tobacco moment or noise?

53:09 Trading Bloom energy BE

55:21 NYC $30/hr gig worker pay rule — what it means for Uber and Instacart

59:06 Lossdog import listed stocks

59:39 Market Talk: bottoming tape, bonds, gold, and VIX

With VIX holding at 30, the conversation around whether "unprecedented times" actually means anything for traders is more relevant than ever — statistically, elevated volatility is already the warning sign, not what comes after it. The job market power shift debate fits into a broader pattern where economic cycles have compressed from decade-long swings to 9–18 month windows, leaving workers and employers scrambling to read the room in real time. The Meta and Google addiction lawsuits with 6,000 cases reportedly in the pipeline mirror early tobacco litigation in scale and precedent, raising real questions about platform liability and what that means for ad-driven tech valuations. And the $30/hr gig worker minimum in NYC is a live test case for the ongoing tension between marketplace wage-setting and legislated labor floors — a debate that directly touches the financial empowerment questions this show exists to answer.

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.

📺 Wa...

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

Tom Sosnoff and Scott Sheridan go solo today — Sol's out with food poisoning — and they don't waste a second. They get into the alleged front-running of Trump's Iran news using S&P futures and crude oil, what $558 million in suspicious notional means on the CME, and whether anyone is actually going to face consequences. Then it's SpaceX at $1.25 trillion and OpenAI close behind — do these numbers scare you, and should they? Tom walks through the Jade Lizard strategy as a capital-efficient hedge for naked put sellers, breaks down 0 DTE options for newer traders, and shares some of the most honest business and trading failures he's been through. Callers bring real questions on market resilience, pairs trading ES vs. oil, broker mid-price integrity, and quantum computing stocks.

#lossdog #optionstrading #stockmarket #insidertrading #jadelize #zerodayoptions

TIMESTAMPS

0:00 Intro — Sol out, today's topics

1:12 Naked puts on ES — Jade Lizard hedge explained

3:55 Trump front-running trade — ES and crude oil

10:14 CME surveillance and accountability

11:07 SpaceX and OpenAI trillion-dollar IPOs

17:22 Buying the dip — position sizing and conviction

20:00 How to disconnect news from the tape

25:10 Caller: Mohammed — market resilience under pressure

29:05 Caller: Ron — ES/oil pairs trade and CME oversight

34:21 Caller: Kapil — broker mid-price integrity in SPX options

38:31 Tom and Scott portfolio secret sauce coming or no?

41:47 Business and trading failures, pivots, and hard lessons

46:02 Social media and job seeking — Tom's contrarian take

50:14 0 DTE options explained

54:03 Quantum computing stocks — rabbit hole or real opportunity

58:37 Live market wrap — VIX, Nasdaq, Meta, Nvidia

With a reported $558 million in notional tied to S&P futures and crude oil moving just minutes before Trump's Iran announcement, the question isn't whether this was suspicious — the CME knows every account behind every order. The real question is whether the CFTC and CME have the spine to follow through when the trail leads somewhere uncomfortable. Meanwhile, trillion-dollar IPO valuations for SpaceX and OpenAI are creating a familiar FOMO dynamic, and Tom draws an uncomfortable parallel to the dot-com era — not because the technology isn't real, but because being priced for perfection leaves no room for anything to go wrong. For retail traders navigating all of this, the practical playbook hasn't changed: keep size disciplined, watch the tape over the headlines, and use elevated volatility as an opportunity rather than a reason to sit out.

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 @...

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

Tom Sosnoff and Scott Sheridan break down what the brokerage of the future actually looks like—simpler interfaces, AI-powered tools, and alternative assets that don't exist on any platform yet. A high school caller gets real advice on staying engaged in markets before college. Beth in Iowa gets the quick-and-dirty tax math on $100K in quarterly futures profits and asks S-Corp vs. LLC. The show also gets into why benchmarking against competitors is a fast track to failure, what operational mistake kills more startups than bad ideas, how the labor market tilts power toward employers right now—and what changes when workers actually know their worth.

#lossdog #optionstrading #stockmarket #futurestrading #salary #career

TIMESTAMPS

0:00 Intro

0:07 Future of brokerages: AI, simple interfaces, alt assets

5:51 Buying power explained: options vs. stocks in Reg T accounts

7:19 Caller Aarav: trading advice for a high school student

10:52 Caller Beth: futures tax math and S-Corp vs. LLC

15:30 Weekend hack: how to check where futures open on Sunday

17:30 Caller Justin: Futures options's closing times

22:15 Last 30 minutes of trading: is it really more volatile?

24:01 When to take assignment instead of closing a futures option

26:31 When creating a business focus on creating your own category

28:40 Fed and bonds - Tom sells /ZN puts

32:15 Lossdog and knowing your worth in a soft labor market

35:25 What operational weakness kills startups more than bad ideas

38:14 'List' of to-do's before entering your first trade

40:52 What Lossdog software actually does (and doesn't do)

43:39 Investing in what you know

45:36 Aerospace, defense stocks, and would you go to space?

51:15 Gold prices

53:28 Adjusting strangle positions

55:22 Market Talk: S&Ps, Bitcoin, VIX, bonds, Micron

With over 100 job applications rolling in for a single posting, employers hold the cards in 2026's labor market—and most workers are negotiating blind. That's the backdrop for everything Tom and Scott are building with Lossdog: a way to shift information back to the individual. Meanwhile, futures markets are more accessible than ever thanks to micro contracts in gold and silver, but settlement quirks and wide options markets still trip up newer traders daily. On the macro side, bonds are soft, gold vol is elevated, and the Fed's room to maneuver keeps shrinking—making premium-selling strategies both attractive and nerve-wracking at the same 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. Lossd...

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

Markets were chaos overnight — gold down $300, silver getting crushed, S&Ps swinging 200 points on a single Trump comment — and Tom Sosnoff and Scott Sheridan showed up with real answers. Scott walks through exactly what brokers do when your account is at risk: auto-liquidation, margin calls, payment plans, and why last April's VIX spike was so much more dangerous than today's move. Tom gets into LEAP strategies for Apple and Microsoft, the 25% premium retention rule for income traders, prop firm red flags, the SPAN margin coding glitch that's costing ES options traders buying power, and what the pattern day trade rule change in late April means for retail. Callers bring live questions on bond strangles, Roth IRA conversions near RMD age, oil calendar spreads, and how to frame multi-university experience on a resume. Plus a fond, honest look back at Karen the Super Trader — her timing, her philanthropy, and what the SEC cost her.

#lossdog #optionstrading #stockmarket #futurestrading #daytrading #financialfreedom

TIMESTAMPS

0:00 Intro

0:17 What brokers do when your account blows up

5:00 Last April vs today: why the VIX spike was worse

7:59 Bond strangle vs skewed strangle after big moves

12:57 Chaotic market playbook: is there one?

15:30 Are prop firms legit? Red flags explained

17:40 Fight to the bitter end vs cutting losses early

21:02 Live caller: LEAP strategy for Apple and Microsoft

24:05 Premium selling as income: the 25% retention rule

26:23 Trading time frames by instrument type

29:20 Bitcoin and the dinner table contrarian indicator

31:18 New merch: swag.lossdog.com

31:52 Oil calendar spreads and contango plays

33:20 Caller Paul: SPAN margin coding issue in ES vertical spreads

38:08 Pattern day trade rule change coming in April

39:04 Roth IRA conversion near RMD age: what to know

42:19 Natural gas price spread: US vs Europe explained

46:24 Karen the Super Trader: a real reflection

52:31 Transient vs study abroad student on a resume

54:03 Tom's study abroad anecdotes

58:40 Market Talk: Bitcoin, gold, oil, ES, VIX

Markets are in a sustained volatility regime right now — geopolitical tension in the Middle East, a Fed caught between inflation risk and economic slowdown, and a yield curve widening to multi-year extremes are all feeding the kind of overnight swings that test traders who've never lived through a real margin event. Understanding what actually happens inside a brokerage when positions go sideways — not just the theory, but the liquidation triggers, the capital call process, and the SPAN margin mechanics — is table stakes for anyone trading futures or short premium in 2026. The pattern day trade rule change expected in late April is a structural shift that could meaningfully redirect retail options flow away from futures products and back into SPX and SPY, which is worth watching closely. And the question of how much premium a trader can realistically keep — about 25% of what's collected, based on years of tastytrade research — is one of those numbers that changes how you think about sizing an income strategy entirely.

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...

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

Gold just shed nearly $600 in two days — and Tom and Scott couldn't disagree more about what it means. Tom calls it a meme, Scott sees a macro story playing out, and neither is backing down. Beyond the gold and silver chaos, the show gets into Tom's oil premium strategy (short wide strangles, April expiration), why the CFA might still be worth it even with AI eating into finance jobs, and the real mechanics of how traders made money screaming in the pits. Callers bring questions on rental property equity, quarterly earnings going semi-annual, implied vs. realized volatility, and spread scanner frustrations — plus NCAA tournament sleeper picks to close it out.

#lossdog #optionstrading #goldsilver #crudeoil #financecareers #triplewitching

TIMESTAMPS

0:00 Intro

0:15 Oil trade breakdown — selling premium in crude

1:53 Gold and silver crash — meme or macro?

8:40 At-the-money options: spot vs. futures price

9:36 Why brokers don't show illiquid silver options

12:07 Caller Steven — how pit traders actually made money

19:56 CFA vs. AI — is it worth pursuing in 2026?

24:22 Ideal portfolio theta as percent of net liq

25:25 LNG trade idea and natural gas performance

27:57 Caller Mark — pulling equity from rental properties

32:21 Institutional ownership and market crashes

34:54 Futures the most liquid product

38:00 Implied vs. realized volatility and fat tail events

41:14 Caller Mike — the tastytrade sale story

45:47 Spread scanners and liquidity traps

48:02 Pairs trade CL/GC?

49:19 Quarterly earnings going semi-annual — good or bad?

52:53 ATR to calculate time to target - Use options deltas instead

54:51 Market Talk: gold, silver, SPY, Bitcoin, triple witching

Gold has been one of the most emotionally traded assets of 2026, running to near all-time highs before shedding hundreds of dollars in a matter of days — exactly the kind of volatility that makes premium sellers salivate and directional traders nervous. At the same time, AI's disruption of white-collar finance jobs is no longer theoretical; it's reshaping career calculus for anyone considering credentials like the CFA. The proposal to move public company earnings from quarterly to semi-annual reporting is gaining real traction under the current administration, and if it passes, it would meaningfully reduce trading volume events that retail platforms and individual traders depend on. Triple witching expiration events — like the one hitting Friday — add another layer of short-term complexity that experienced traders navigate carefully, especially heading into the close on Thursday. These aren't abstract market debates; they're the decisions and tradeoffs that determine real P&L.

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.

Micron is at all-time highs with earnings after the close—so Tom and Scott get into how they're positioned, why the wheel strategy isn't the move here, and what the real risk-reward looks like when a stock has already rallied $200 from year-end. Then a couple asks what to do with $487K in home sale proceeds, and Tom explains exactly how he'd break it down using an AI-powered agentic portfolio tool—and why that's a hundred times better than any legacy advisor. The conversation opens up into which finance jobs AI is about to hollow out, why pre-clearing trades at big banks is a relic that needs to die, and what tokenized stocks actually mean for day traders. Callers weigh in on selling puts by delta, trader networking, and whether farmland can ever be tokenized.

#lossdog #optionstrading #stockmarket #aiinvesting #financecareers #daytrading

TIMESTAMPS

0:00 Intro

0:08 Should you short Micron before earnings?

5:08 Tom's Micron history — from $2 to $500

7:23 Wash sales explained (sort of)

8:02 How to invest a $487K home sale windfall

10:13 AI builds your portfolio — what that actually looks like

14:34 Caller: Which puts pay the most? Delta strategy explained

17:04 OKLO nuclear stock — worth trading after the drop?

18:35 Caller: How to network as a serious retail trader

22:47 Tokenized stocks explained — what changes for day traders

26:59 Caller: Backtesting platforms and the AI portfolio future

32:38 Beta-weighted vs. individual delta — how to manage positions

34:42 High skew does not mean free money

36:26 Caller: Parenting a teenager who just started dating

39:44 Caller: Chicago real estate losses + tokenizing farmland

44:25 Does AI narrow or widen the wealth gap?

48:10 Finance jobs AI is coming for — RIAs, analysts, advisors

51:11 Tom and Scott discuss generous payouts

53:58 PDT rule - Trading futures options /ES and /MES

55:57 Real estate poll results — did you actually make money?

56:20 Potential finance jobs that will be impacted by AI

59:44 Market talk: Fed day, Micron earnings, Bitcoin, bonds

Tom Sosnoff and Scott Sheridan built two of the most important retail trading platforms ever—thinkorswim and tastytrade—and they've watched the financial industry resist change at every turn. Right now, agentic AI is doing to portfolio construction what the internet did to information access: making it available to everyone, not just people with expensive advisors or institutional connections. At the same time, the PDT rule is finally on its way out, tokenization is inching toward the derivative space, and finance jobs that once required armies of analysts are quietly disappearing. This episode sits at the intersection of all of it—practical trade mechanics, the real future of investing technology, and what it means for anyone trying to build wealth without a six-figure head start.

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 t...

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Tom Sosnoff and Scott Sheridan get into the real strategy behind surviving a market crash—spoiler: it's not about timing it, it's about size. They also break down the crypto wash sale loophole the IRS hasn't closed, whether trade journaling actually matters, and Tom's highest conviction trade right now heading into Micron earnings. The OEX pit gets some love too, with wild stories from the floor. Plus: should workers have a seat on corporate boards, how to measure organic startup growth, and a live market rundown with VIX levels, crude oil, gold, silver, and Bitcoin catching a serious bid.

#lossdog #optionstrading #stockmarket #investing #financialfreedom #tradingstrategy

TIMESTAMPS

0:00 Intro

0:10 How to survive the next market crash

2:23 Is 2026 the end of buy the dip?

3:35 IONQ and SOUN: quantum computing stocks

6:35 OpenAI at $850B—is the AI hype real?

7:20 What metric founders ignore that actually signals survival

10:03 Crypto wash sale rule explained

11:30 Should you journal your trades?

14:16 SPX vs XSP iron condor—what's the real difference?

16:37 What does trading small actually mean?

19:12 The problem with trading small: can you make real money?

20:30 Selling options vs. buying options—the insurance analogy

25:41 Better trader: Tom with or without beret

26:13 Should workers have board representation?

28:22 Best trades and craziest moments from the OEX pit

30:59 Books and resources for learning the market maker's playbook

32:22 Advice for your 35-year-old self

33:44 Midterm election year drawdowns and how to position

37:36 One account or three? The $150K split question

40:59 Tom's highest conviction trade to fade

43:55 How to measure organic startup growth

46:02 Explanation of 'bought the put book at a cabinet'

47:37 High Oil and Inflation - interest rates

50:03 Finding your trading edge and entry point

52:57 Adjusting trading style after leaving the floor

56:10 Market Talk: Micron, Bitcoin, gold, silver, VIX, bonds

With the S&P sitting on historically elevated valuations and the average midterm election year drawdown coming in near 19%, 2026 is shaping up to be a year where position sizing and portfolio construction matter more than stock-picking. The crypto wash sale loophole—still active because the IRS classifies crypto as property, not a security—gives active traders a real tax tool that doesn't exist anywhere else in the market. Meanwhile, Micron earnings, triple witching, and a volatile week in crude oil and gold are all reminders that volatility doesn't announce itself—it just shows up. The conversation around whether startup founders are optimizing for the wrong metrics (EBITDA over growth) mirrors a broader tension in the market: are investors pricing in fundamentals or just narrative? These are the questions that separate people who build durable wealth from those who get caught leaning the wrong way.

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 wonde...