One Lucky Dog

One Lucky Dog

By LossdogBusinessEntrepreneurshipInvesting
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One Lucky Dog episodes

  • Tom's 0DTE ATM Straddle/Strangle & Silver's Next Move 02.02 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down the aftermath of Friday's silver crash, explain why commodities can trade like meme stocks, and share hard lessons about risk discipline. A caller asks how to manage a natural gas strangle from hell, and the hosts explain why trading futures against underwater options digs deeper holes. Plus: why Tom thinks MicroStrategy is a scam, the federal deficit debate, real estate illiquidity premiums, and whether the government should take equity stakes in private companies.

    #lossdog #optionstrading #silver #naturalgas #stockmarket #tradingstrategy

    TIMESTAMPS

    0:00 Intro
    0:39 Eight-legged spreads vs scaling four-legged trades
    3:05 Silver crash aftermath and what Tom learned
    4:49 Barry asks about the silver trade and lessons learned
    6:07 How silver reset Tom's trading discipline
    6:47 Real estate illiquidity premium question
    9:13 Why Tom never made money in Chicago real estate
    11:47 Vincent from Alabama asks about natural gas gap down
    14:38 How Globex matches buyers and sellers overnight
    16:25 Adjusting GLD puts with 57 days to expiration
    19:19 Paul from LA asks about federal debt and deficits
    25:32 Scott from Florida on natural gas strangle management
    29:12 Why you never trade futures against underwater options
    31:47 Charm and Vanna flows explained (second derivative Greeks)
    33:18 Government taking equity stakes in private companies
    40:02 Should Chicago own part of the Bears
    42:12 Aaron from Arkansas asks about MicroStrategy
    48:03 Tom's weekend Bitcoin, ETH, and Solana buys
    50:45 Buying power vs net liq explained
    52:39 Will silver close over 100 before July
    55:32 Software stocks and AI tools fear question
    59:22 Market talk and today's moves

    The tariff situation rattled global markets over the weekend, sending Bitcoin down 40% from its highs and natural gas through wild 20% swings in both directions. For traders caught on the wrong side of these moves, the hosts walk through practical adjustment strategies: why rolling down and out rarely works, why selling calls against underwater puts reduces theoretical risk, and why adding futures to fix options positions usually makes things worse. The MicroStrategy discussion highlights a broader concern about convertible debt structures that offer neither stated interest rates nor conversion ratios, a setup Tom calls unprecedented regardless of regulatory approval.

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

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

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

    1 hr 5 min
  • Running the Wheel & SELLING Silver | 01.29 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down why physical silver dealers are refusing to buy right now, how to apply the wheel strategy to futures options, and the wild economics of influencer deals worth nearly a billion dollars. The crew takes calls on everything from picking the most consistent commodity to trade, to whether the government should force people to save for retirement. Plus, a 30-year-old caller gets a reality check on what a real market sell-off looks like, and someone asks if options on options exist.

    #lossdog #silverprices #optionstrading #wheelstrategy #predictionmarkets #financialeducation

    TIMESTAMPS

    0:00 Intro
    0:57 The wheel strategy explained for futures options
    5:43 Physical silver problem: why coin shops won't buy
    12:24 Tom's early days arbing silver dimes
    16:30 Call: best commodity for consistent premium
    20:14 Should the government force you to save?
    22:37 Why Tom thinks investing for retirement is overrated
    25:40 Starting over: what it means to serial entrepreneurs
    27:51 Prediction markets: the future and the fee problem
    36:06 Call: options on options, do they exist?
    37:44 Call: influencers, Miss Universe, and a $975M TikTok deal
    43:44 Call: is this the dip to buy?
    49:30 Should schools bring back wood shop and vocational training?
    54:29 Call: early assignment risk on short calls before dividends
    58:40 Market wrap: S&P down 95, NASDAQ down 570, silver crashes $10

    The physical precious metals market is flashing warning signs for retail holders. With silver swinging $10 or more in a single day and gold moving $200, small coin shops face impossible hedging challenges, leaving sellers without a bid. Meanwhile, prediction markets are gaining mainstream traction with valuations like Polymarket's $9 billion ICE deal, but transaction costs still run 200x higher than trading Apple stock. As the debate over forced retirement savings heats up and vocational education makes a comeback in policy discussions, the gap between financial literacy and real-world money skills keeps widening.

    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
    🐕 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.

    1 hr 5 min
  • Tom Reveals His Currency Trading Secret | 01.28 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff breaks down how to trade the Japanese yen using naked puts, why short silver has been a bloodbath for traders everywhere, and what the historic 5-sigma move in silver actually means. Scott Sheridan explains the exact steps to lock your credit at all three bureaus and why 2FA on your email is non-negotiable. The crew also gets into the inverse correlation between the dollar and U.S. equities, whether NVIDIA funding startups to buy their chips is sustainable, and why blockchain technology is still here to stay despite falling out of the headlines. Plus callers share real trading disasters and ask about exchange outages, iron condor management, and the macro case for market resistance.

    #lossdog #silvertrading #optionstrading #cybersecurity #creditfreeze #nvidia

    TIMESTAMPS

    0:00 Intro
    0:02 Trading the Japanese yen with naked puts
    4:06 Japan travel is on sale with the weak yen
    7:18 What's happening with the Widowmaker in natural gas
    10:50 Lossdog platform launch and $1 million crypto giveaway
    11:29 Caller Rob wishes Scott happy anniversary
    14:32 Caller Tony asks about exchange outages and trading risk
    20:38 Dollar vs equities inverse correlation explained
    24:42 Slash made the Lossdog intro music
    26:44 How to lock your credit and set up 2FA
    30:32 Beta vs IV rank for selling options
    31:50 Rolling the unchallenged side of an iron condor
    35:50 Caller Ryan on silver's 5-sigma move
    40:36 Legal fees are out of control and how AI helps
    44:46 Where did the promise of blockchain technology go
    47:06 NVIDIA funding startups to buy their own chips
    53:00 Caller presents macro resistance thesis
    55:58 Market update and Starbucks earnings trade

    The silver market just experienced a historic 5-standard-deviation move that took out traders across the board. Tom reveals he got short at 52 and watched it climb to 113 in under three months. Meanwhile, identity theft remains rampant with most people's data already exposed from past breaches. With legal fees now reaching $2,700 per hour for crypto attorneys and AI increasingly handling foundational legal research, the landscape for both trading and business expenses is shifting fast. The prediction contest deadline is January 31st with a $5,000 prize 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 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
    🐕 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.

    1 hr 2 min
  • Bullish Stablecoin Bets and "Dumb Money" Bots | 01.26 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down why Circle's correlation to Bitcoin makes zero sense, when to ignore the 50% profit-taking rule, and what's actually happening with gold and silver as prices go parabolic. Plus: how to sell covered calls on positions with 20 years of unrealized gains without triggering a tax nightmare, why quants and bots aren't your enemy, and which beaten-down sectors might finally bounce in 2026. Callers weigh in on silver circuit breakers, the gold-silver ratio hitting 20-year lows, and whether political tension will finally crack the market.

    #lossdog #optionstrading #goldprice #silverinvesting #stockmarket #coveredcalls

    TIMESTAMPS

    0:00 Intro
    1:35 Is Circle correlated to Bitcoin? (Spoiler: it shouldn't be)
    5:27 Stablecoin plays beyond Circle
    6:29 Futures vs ETFs vs physical for metals
    10:41 When to take profits before 50%
    13:30 Caller: Silver circuit breakers and the gold-silver ratio
    15:48 Lossdog app launch update and waitlist tiers
    17:22 S&P overnight swing: down 60, up 40
    18:44 Last week for $5,000 Lossdog Prediction Contest
    19:53 Caller: Why hasn't XLV dropped on drug pricing news?
    23:34 Physical gold as a hedge against exchange intervention
    27:47 Lossdog Network expansion plans
    30:34 At-the-money vertical spreads and put-call parity
    32:37 Top sectors for 2026: dogs over darlings
    36:41 Covered calls on long-term holdings without tax pain
    39:09 Can retail compete with quants and bots?
    46:19 How to examine regime shift quantitatively
    48:52 FIRE movement follow-up
    50:04 What breaks the market: earnings, politics, or credit?
    55:48 Caller: Bearish case for 2026 and interest rate impact
    1:00:04 Market wrap: gold $5,087, silver $112, Bitcoin $88K

    Gold crossed $5,000 less than three weeks into 2026 after trading around $4,400 when the Lossdog Prediction Contest launched—a move that seemed statistically inevitable over the full year, not in January. The gold-silver ratio dropped to roughly 47, its lowest in two decades, as silver surged past $112. Meanwhile, U.S. equities shrugged off overnight futures weakness and geopolitical noise to rally back near all-time highs, leaving traders debating whether political tension, AI valuations, or something nobody sees coming will finally trigger a correction.

    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
    🐕 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.

    1 hr 5 min
  • Best Biz Advice Ever, Peanut Butter and the Widowmaker | 01.22 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan share the best business advice they ever received—and why resilience and risk-taking matter more than playing it safe. The show gets into the so called 'peanut butter raises' (55% of Fortune 500 companies use them), why most employees think they crushed it even when they didn't, and how to actually make your case for better pay. A caller running three businesses including a 10-million-card Pokemon distribution company gets real talk on scaling without burning out. Plus, natural gas moved 75% in three days and silver hit all-time highs—Tom and Scott break down what's happening and why they wouldn't touch gold right now.

    #lossdog #careerdevelopment #salarynegotiation #optionstrading #naturalgas #goldprice

    TIMESTAMPS

    0:00 Intro
    1:11 Best business advice Tom and Scott ever received
    1:39 Why resilience beats any single piece of advice
    4:33 Take risk every chance you get
    7:14 Caller Alan on scaling three businesses at once
    11:48 How to manage multiple companies without micromanaging
    16:13 Peanut butter raises and why 55% of companies use them
    20:05 Every employee thinks they killed it
    21:47 Caller Scott on natural gas strangles gone wrong
    28:45 Why natural gas is called the widow maker
    30:53 Lossdog prediction contest and $1M crypto giveaway
    31:55 Caller Steve on handles vs percentages debate
    41:14 Caller Arthur on hedging a long call spread portfolio
    48:31 Active vs passive investing and why buy-and-hold isn't enough
    50:26 Is gold too expensive to buy now?
    53:41 Fintech vs big banks: where the real opportunity is
    57:31 Market rundown and earnings preview

    The 2026 job market is forcing workers to rethink how they negotiate compensation. With over half of major corporations defaulting to uniform percentage raises, individual performance often goes unrewarded unless employees advocate for themselves. Meanwhile, commodity markets are reminding traders that volatility cuts both ways—natural gas and precious metals have delivered gut-wrenching moves that separate disciplined position sizing from portfolio blowups.

    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
    🐕 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.

    1 hr 3 min
  • Best Strategies for Shorting the Market | 01.21 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down the best strategies for shorting the market when you're leaning bearish, from naked calls in SPY to micro futures in the ES and NQ. They get into why long put verticals don't give you the "oomph" you're looking for on big down moves, how to manage accounts once they exceed $10 million (spoiler: it's nearly impossible), and why yesterday's 2% selloff isn't the buying opportunity everyone on TV thinks it is. Plus a caller asks if her money is safe at tastytrade after Tom and Scott left, and a mother-daughter duo calls in back to back.

    #lossdog #optionstrading #stockmarket #shortingthemarket #tradingstrategies #spyfutures

    TIMESTAMPS

    0:00 Intro
    0:18 Best strategies to short the market
    3:37 Why long put verticals lack oomph
    3:41 Short skewed strangles warning
    6:00 Netflix earnings trade breakdown
    6:59 VIX cash vs futures spread
    7:46 Private investment philosophy
    10:23 Account size limits for active trading
    14:33 Nvidia market cap vs Germany's stock market
    15:50 The 100-step binomial strategy explained
    17:55 The 390 order rule for professional traders
    26:26 Bitcoin and NASDAQ correlation as pairs trade
    28:35 Startup funding and presenting metrics to investors
    32:48 Caller Beth asks about account safety in brokerage firms
    38:20 Adapting options strategies in low volatility
    44:45 Career pivot advice for a 51-year-old teacher
    49:20 Bitcoin allocation and portfolio percentage
    53:29 Caller Shay asks how to start from scratch
    57:02 Market talk and why Tom is short

    The 2026 market rally has pushed the S&P 500 to within 2% of all-time highs, compressing implied volatility and shrinking the edge for premium sellers. For traders looking to position short, the challenge isn't just picking direction—it's maintaining delta exposure when gamma works against you on big moves. Meanwhile, the Bitcoin volatility collapse to mid-40s IV levels now puts it in the same risk bucket as Nvidia and Tesla, fundamentally changing its role as a portfolio diversifier.

    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
    🐕 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.

    1 hr 4 min
  • Defending Naked Puts and Why "Prediction Markets Suck" | 01.20 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol break down what "trade small, trade often" actually means in practice—from contract sizing to tax strategy to defending naked puts. Tom shares his real position sizing (five to ten lots in options, one to two in futures) while explaining why the average industry trade is just 3.5 contracts. They tackle bond market moves as rates climb despite Fed expectations, reveal their favorite option strategies (short naked puts win for consistency, but strangles are their go-to), and explain why making money matters more than optimizing taxes. Plus: silver and gold trades, CEO turnover predictions, and why Tom's burnt-end chili never made it to Scott's porch.

    #lossdog #optionstrading #stockmarket #trading #salary #career

    TIMESTAMPS

    0:00 Intro
    3:42 Trade small and trade often—how many contracts?
    5:27 Bond market moves—what drives them?
    10:13 Tax strategy for traders—worry about profits first
    14:50 Gold and silver trades—momentum vs mean reversion
    18:09 Silver scalping since Sunday night
    20:03 Prediction markets vs traditional bookmakers
    26:04 Will AI influence the betting market?
    29:51 Caller ask about Tom and Scott's trading routines and sport chat
    37:25 CEO changes coming in 2026—Tim Cook prediction
    38:56 How to shift focus without spreading too thin
    42:08 Forecasting challenge reminder—deadline January 31st
    43:30 Most consistent option strategy: short naked puts
    48:48 How to set up a co-operative and Tom's college co-operative stories
    59:33 Market wrap-up

    The 2026 economy is showing cracks in the traditional Fed narrative. Bond markets are pricing in higher long-term rates even as the new administration pushes for cuts, creating a divergence that hasn't been this stark in years. Meanwhile, retail traders face the same challenge they always have: position sizing. The industry average of 3.5 option contracts suggests most people are already trading small, but the real question is whether that size matches their risk tolerance and capital base. Tax considerations add another layer—with potential policy changes looming and capital gains treatment always in flux, the balance between optimization and execution becomes critical. These aren't abstract concerns; they're the daily decisions that separate consistent traders from those who blow up trying to get too clever.

    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
    🐕 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.

    1 hr 2 min
  • Silver Never Sleeps & Iron Condors vs. Strangles | 01.15 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff breaks down his overnight silver trading strategy while Scott Sheridan explains why strangles are easier to manage than iron condors for options traders. The crew tackles a father managing his daughter's account with 21-28% annual returns, debates whether engineers should ask employers for part-time status to pursue side projects, and gets brutally honest about why most bosses would say no. Plus, a deep cut on transfer pricing careers, the flawed home loan system that punishes 1099 workers, and why the Bears-Packers rivalry is the best thing happening in sports right now.

    #lossdog #optionstrading #careeradvice #salarynegotiation #stockmarket #financialfreedom

    TIMESTAMPS

    0:00 Intro
    3:50 Football weekend food plans and bratwurst debate
    8:02 Tom's overnight silver trading breakdown
    10:01 When Harry Met Sally and old movies R.I.P. Bob Reiner
    12:57 Managing daughter's options account with strangles vs iron condors
    15:43 Stay focused: advice from a board meeting
    17:52 Saks Global bankruptcy and the future of retail
    20:05 Gen Z bringing back mall culture and cigarettes
    21:31 Are extended options trading hours coming soon
    23:27 What makes a 38-year business partnership work
    25:54 Engineer wants part-time status for a side project
    29:34 MBA right after undergrad or get work experience first?
    32:41 Michael Jordan vs Tom Brady: toughest competitor
    36:29 Transfer pricing careers explained
    42:15 When would you actually buy options instead of sell?
    45:08 How to validate a business idea when starting from scratch
    50:32 Poll results and Bears-Packers rivalry is the best thing in sports
    54:50 Breaking the W-2 culture and the flawed home loan system
    58:45 Market Talk

    The home lending system in America is built around W-2 employment as a proxy for stability, even though a salaried employee could lose their job the day after closing on a house. This creates real friction for entrepreneurs, freelancers, and 1099 workers who often have more financial discipline but less paperwork to prove it. The conversation also touches on why banks fail—spoiler: it's rarely bad home loans and almost always mismanaged risk elsewhere in their portfolios.

    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
    🐕 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.

    1 hr 3 min
  • "Should I Change My Trading Game as I Get Older?" | 01.14 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol break down a volatile market morning with the S&P down 67 points and VIX spiking 10%. The crew gets into the heated work-from-home debate, where Tom claims remote workers don't actually work while Scott argues for balance. They explain how asset tokenization will open up hedge funds and private equity to everyday investors, walk through copper versus silver as a hedge, and share their near-term crypto outlook. Callers ask about teaching friends to sell premium instead of buying options, and Paul from Chicago drops a quick formula for converting hourly wages to annual salary.

    #optionstrading #cryptocurrency #workfromhome #tokenization #volatility #investing

    TIMESTAMPS

    0:00 Intro
    3:28 Market open: S&P down 60, VIX up 10%
    5:19 Tom's silver and gold position pain
    7:45 Using copper to hedge short silver trades
    10:44 What made you choose your office location
    11:30 Tom's take on working from home
    13:56 Do trading platforms still matter
    16:24 Quarterly vs semi-annual earnings reporting
    18:52 Near-term crypto outlook and buying dips
    21:08 Retirement investing: should your strategy change
    27:46 Asset tokenization and alternative investments
    30:43 Caller: convincing a friend to sell premium
    36:22 Poll pushback on adapting trading with age
    37:11 Career transition and Lossdog technology
    39:25 Midterms and market volatility
    41:39 24/7 tokenized markets: who benefits
    44:40 Caller: hourly wage to salary formula
    45:45 Staying small and buying power across positions
    49:08 Who would play Tom and Scott on a movie
    50:33 Who makes a better trader: mathematician or psychologist
    52:24 guests on the show in the future
    54:32 Fed control and repricing risk
    59:45 Market wrap and prediction contest reminder

    Asset tokenization is quietly becoming one of the biggest shifts in how everyday investors access wealth-building opportunities. For decades, alternative investments like private equity, venture capital, and hedge funds were gated behind accredited investor requirements and massive minimum buy-ins. Tokenization breaks assets into tradeable fractional pieces, letting anyone with a brokerage account participate in markets that were previously reserved for institutions and the ultra-wealthy. Major clearing firms are already building infrastructure to launch tokenized products this year, which could reshape portfolio diversification strategies for retail traders who've been stuck with traditional stocks and bonds.

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

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

    1 hr 3 min
  • Prediction Markets, Stablecoins and Lossdog Swag | 01.13 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol break down what happens when you beat the S&P by 3% but still feel behind, why the Lossdog stablecoin will pay higher rewards than Coinbase, and whether switching jobs works like trading stocks. They walk through real caller questions about undervaluing yourself as a contractor, finding the right startup to join, and why emerging market options are nearly impossible to trade from the US. Plus: the gold-silver ratio hits Scott's break-even, Trump's Fed comments shake up bond markets, and why college grads should take any job that comes their way.

    #lossdog #career #salary #trading #stablecoin #stockmarket

    TIMESTAMPS
    0:00 Intro
    3:26 Lossdog announcement and new swag
    4:02 $5,000 prediction contest details
    6:26 Software launch timeline update
    8:26 Letters from the Dog Pound: 20% return regret
    9:40 Lossdog software goals and features
    14:51 Career development focus for ages 22-50
    15:26 Comparing career paths and roles
    15:47 Stablecoin advantages over competitors
    18:23 Brett from Wyoming: undervaluing yourself as contractor
    22:46 Knowledge is power in career decisions
    23:31 Trading jobs or roles prediction market idea
    26:40 Market update and silver-gold ratio
    28:21 Fed independence and market implications
    30:50 bond market: buy the rumor, sell the news
    32:25 Tom's yen trade
    33:00 Aaron from UNC: switching jobs vs staying put
    37:52 Letters: capital allocation in low volatility
    40:00 Foreign assets and dollar risk discussion
    43:57 Discord groups and trading gurus value
    46:43 Arthur from Brooklyn: emerging market options platforms
    55:07 Startup interview questions about runway
    56:44 How much runway should a startup have
    59:51 Market Talk wrap up

    The job market remains tight for recent grads even as companies post record profits, creating a mismatch where young talent struggles to break in while experienced workers see wage growth stagnate. Meanwhile, the Federal Reserve's independence faces unprecedented public pressure, raising questions about monetary policy credibility that could ripple through bond markets and currency valuations. Stablecoins are emerging as a faster alternative to traditional payment rails, offering yields that compete with money market funds while the crypto infrastructure matures. For professionals navigating this landscape, understanding personal market value becomes critical when traditional salary data fails to account for rapid shifts in supply and demand across roles.

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

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

    1 hr 5 min

About One Lucky Dog

From the publisher's feed

Most professionals are underpaid and don’t even know it. We’re here to help you get paid the most for your time and earn the most on your money. Join at lossdog.com! Fintech firebrands Tom Sosnoff, Scott Sheridan and Tony Battista take your phone calls LIVE every Monday thru Thursday at 10am est. on One Lucky Dog LIVE! Call-in from 10-11am est., M-TH at 989--LOSSDOG. Subscribe to this YouTube channel and @SosnoffonMoney. Lossdog is your personal career and investment portfolio valuation engine. In minutes, our AI turns your resume into a clear, data-backed number: your whole professional worth. No vague ranges. Just the confidence to grow your salary, and your investment portfolio. Subscribe for videos on: --Salary negotiation strategies --Career growth insights --Optimizing your investment portfolio --How to stop leaving money on the table 👉 Know your numbers, grow your numbers at lossdog.com. Follow us on social media @wearelossdog