One Lucky Dog

One Lucky Dog

By LossdogBusinessEntrepreneurshipInvesting
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One Lucky Dog episodes

  • Da Bears and Da Drooling Retirement | 01.12 | 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 most people have no idea what they're actually worth—and how Lossdog's upcoming software finally gives you a real number. A college student asks how to figure out his starting salary with an applied math degree, a trader wants to know if 7-10% monthly returns are realistic (spoiler: they're not), and the hosts get into prop trading firms, position management when trades go sideways, and why they'd never invest in companies they morally disagree with. Plus: the marshmallow test is overrated, and the Bears finally beat the Packers.

    #salary #careeradvice #optionstrading #knowyourworth #stockmarket #tradingstrategy

    TIMESTAMPS

    0:00 Intro
    2:17 Bears vs Packers and Chicago sports talk
    8:06 Bitcoin, gold, silver, and market rundown
    10:36 Student asks how to know starting salary with no work history
    15:03 Lossdog software launch update and UNC pilot program
    16:10 Online prop trading firms: worth it or fee traps?
    19:13 Managing a position that's gotten out of hand
    22:40 Would you invest in a company/person with whom you morally disagree?
    25:15 Should you follow the trend and get long silver?
    26:45 VIX is low—should you reduce your trade allocation?
    28:29 How much should startups spend on marketing?
    32:42 Can you really make 7-10% monthly returns on $30K?
    36:37 Managing a bull call spread on silver
    46:23 Ideal portfolio mix for someone retiring in five years
    50:43 What Lossdog software will actually do for you
    53:56 Is delayed gratification overrated? The marshmallow test debate
    1:01:39 Market wrap and 2026 prediction contest

    The job market in 2026 is shifting fast, and most workers still have no framework for understanding their true market value. Whether you're a recent grad trying to land your first role or a mid-career professional wondering if you're underpaid, the same problem keeps coming up: nobody teaches you how to calculate what you're worth. That's the gap Lossdog is built to fill. This episode also gets real about trading expectations—why shooting for 100% annual returns usually leads to blown accounts, and what a sustainable target actually looks like.

    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 6 min
  • Business Pivots, Raising Capital and the PDT Rule | 01.08 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan kick off the show with a special announcement: Slash recorded an original theme song for Lossdog. From there, the conversation covers zero DTE options strategy when VIX is low, why every successful business pivots, the real sacrifices of building a startup, and how to raise capital when self-promotion isn't your strength. Callers ask about using competing job offers to negotiate salary, the PDT rule timeline, and networking strategies for veterans transitioning to civilian careers.

    #stockmarket #optionstrading #entrepreneurship #salarynegotiation #startup #careeradvice

    TIMESTAMPS

    0:00 Intro
    1:54 Slash wrote an original song for Lossdog
    3:58 NASDAQ looking weak, market overview
    8:40 Zero DTE options: when to trade based on VIX 1D
    11:55 Why every business has to pivot
    15:10 Don't overthink it, pivot
    16:54 The personal and family sacrifices of building a startup
    21:38 How much cash to keep as a safety net for a new business
    23:41 Raising capital when self-promotion isn't your strength
    31:41 Caller: Using a competing offer to negotiate salary
    37:52 Caller: tastytrade “Rising Star” shares networking strategies for veterans (Honor Foundation).
    41:58 VIX under 15: how much capital to allocate to short premium
    45:11 The value of in-person meetings vs Zoom
    47:56 Caller: Hourly options, PDT rule update, and tokenized clearing
    55:51 Market check and January expiration outlook
    58:45 2026 Predictions and college football picks: Ole Miss vs Miami

    The job market in 2026 remains competitive, and knowing your professional worth has never been more important. Whether you're negotiating a raise, considering a career change, or transitioning from military service to civilian work, having real data on your market value changes everything. This episode also breaks down why low volatility environments require different trading strategies and why every entrepreneur should expect to pivot multiple times before finding product-market fit.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 4 min
  • Tom Sosnoff Reveals His Near-Term Target for Silver | 01.07 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff admits he was up until 3 AM trading silver after it hit a double top at $82.50, while Scott Sheridan breaks down why entrepreneurship is basically an undefined risk trade. The hosts get into price extremes, efficient market theory versus macro events, and why public liquidity pools for insurance premium could be the next big disruption. Plus a caller lands an investment banking job using advice from the show, and a debate started about whether college athletes should get paid.

    #stockmarket #optionstrading #silver #careeradvice #collegefootball #investmentbanking

    TIMESTAMPS

    0:00 Intro
    2:13 Silver hits double top at $82.50
    4:03 Market rundown: Bitcoin, oil, gold, bonds
    7:31 Entrepreneurship as an undefined risk trade
    10:08 Gold and silver price predictions for 2026
    11:53 How to identify price extremes in trading
    14:14 Asymmetric risk: selling premium vs buying options
    16:46 Public liquidity pools for insurance premium
    21:46 Managing underwater short put positions
    24:54 Were Scott and tastytrade employees allowed to trade?
    31:45 Caller from Greenland asks about Jim Harbaugh firing
    34:30 Debate over paying college athletes
    38:07 Edwin lands investment banking job with show advice
    42:22 AMD looking cheap relative to other tech stocks
    44:03 Efficient market theory vs macro events
    48:40 Business plans vs working software models
    51:40 Will /ES and /NQ Index Future contracts ever split?
    54:43 Why Lossdog couldn't offer equity to viewers

    The efficient market hypothesis remains the most reliable framework for traders, even when global macro events dominate headlines. Tom explains why price is king and macro discussions exist mainly to fill airtime on financial media. With silver showing a textbook double top and AI stocks potentially overheated, contrarian traders are looking for pot odds setups where risk-reward asymmetry favors the patient seller. Meanwhile, the prediction contest launches Friday and a major Lossdog software announcement is coming soon.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 2 min
  • "My Biz Partner Had an Affair... Do I Axe Him?" | 01.06 | One Lucky Dog LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle the fears every entrepreneur faces: protecting ideas from competitors and big company buyouts. A caller shares a tough decision about ending a business partnership after discovering his partner had an affair with a customer, sparking discussion about trust and professional relationships. The hosts also break down Bitcoin and Ethereum ETF options, explain why the VIX rising with the market can be a red flag, debate outsourcing versus hiring developers for startups, and discuss the future of the U.S. space economy. Plus, a deep dive into option premium challenges when volatility is low and what makes a four-decade business partnership actually work.

    #stockmarket #optionstrading #entrepreneurship #startup #bitcoin #partnership

    TIMESTAMPS

    0:00 Intro
    4:00 Markets overview and trading signals
    5:30 Startup fear: Will someone steal my idea?
    7:30 Why nobody invests in ideas, only people
    10:00 thinkorswim early days and outside interest
    12:30 Best ETFs for Bitcoin and Ethereum options
    14:50 Caller Mark: Ending partnership after affair
    21:18 VIX up with market: Is it a red flag?
    23:30 Outsourcing developers vs building internal team
    28:35 Caller Mike: Stock jumps from $20 to $70
    33:22 tastytrade in Canada: What happened?
    35:05 Iron condor time diversification explained
    38:45 Caller Cesare: U.S. space economy outlook
    45:50 Caller Mark: Secret to a 40-year partnership
    56:19 Poll results: Ditch partner after affair?
    57:20 Caller Wayne: Why is option premium so low?

    The job market in early 2026 remains volatile, with tech layoffs continuing alongside selective hiring in AI and specialized roles. For entrepreneurs, knowing when to protect your work and when to share it openly can make or break a startup. Meanwhile, historically low volatility is making premium selling strategies less attractive, pushing traders to rethink their approaches. Whether you're negotiating salary, evaluating a business partner, or deciding how to structure your options trades, understanding market dynamics and trust fundamentals has never been more critical.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 4 min
  • "Can I Trade My Way to Building Wealth?" | 01.05 | O.L.D. LIVE!
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol kick off 2026 with a packed episode covering whether trading can actually build wealth, the research-backed case for widening option strikes instead of adding contracts, and why post-earnings announcement drift is statistically random after 48 hours. Callers ask about employee stock purchase plans at 15% discount, S&P settlement mechanics for zero DTE traders, and scalping strategies. The hosts also share the story of how they first met in Las Vegas, reflect on transforming the retail options industry, and discuss market implications of the Venezuela situation.

    #stockmarket #optionstrading #wealthbuilding #tradingstrategy #scalping #earningsseason #venezuela #maduro

    TIMESTAMPS

    0:00 Intro
    1:15 Show open and 2026 kickoff
    6:15 Employee stock purchase plans at 15% discount
    9:25 S&P settlement timing for zero DTE options
    13:40 Can the market drop 15% without a catalyst
    15:50 Investing without proof of concept
    19:10 Venezuela oil situation and market reaction
    21:40 Brett asks how Tom and Scott met
    27:00 Debit spreads: widen strikes vs add contracts
    32:00 Tony from La Jolla on building wealth through trading
    43:20 Post-earnings announcement drift research
    47:10 Earnings season preview and low volatility concerns
    53:20 Venezuela president Nicolás Maduro's arrest and global risk
    57:35 John from San Diego on scalping strategy
    1:00:40 Desert Storm trading day memories

    These topics hit at the core of what retail investors are searching for in early 2026: whether active trading is a viable path to wealth, how to optimize options strategies in a low-volatility environment, and what geopolitical uncertainty means for markets. With earnings season starting next week and the VIX hovering below 15, the discussion on premium selling and expected move risk is especially timely for traders weighing their January positioning.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 4 min
  • Bitcoin, Baseball Cards and Fossils | O.L.D. LIVE! | 12.31
    Join the Lossdog wait list at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan kick off New Year's Eve by exploring unconventional investment opportunities—from Bitcoin and baseball cards to the surprising underground market for fossils (yes, NFL quarterback Joe Burrow is a collector). The episode tackles critical questions about how Lossdog's AI-powered valuation tool can empower workers even when employers have fixed salary budgets, why the restaurant industry makes career advancement so difficult, and whether the AI stock bubble is finally ready to burst in 2026. Callers share real stories about navigating pay gaps between cities, the challenges of proving your worth after years of underpayment, and why most Americans struggle to save money due to cultural spending habits rather than lack of income.

    #stockmarket #investing #career #salarynegotiation #Bitcoin #optionstrading

    TIMESTAMPS
    0:00 Intro
    4:14 Should you invest with a CTA? Tom says no
    8:51 Bitcoin, baseball cards, and fossils as investments
    12:13 Joe Burrow's fossil collection and alternative assets
    15:19 How Lossdog helps when employers won't budge on salary
    17:51 Will the AI bubble burst in 2026?
    23:17 How futures contracts settle and why it's confusing
    26:58 Chef struggles to get raises after 5 years
    31:13 Best options trading strategy for 2026
    36:34 Why Americans don't save money
    41:19 What Tom would add to financial literacy education
    46:23 How much capital you need for a startup
    50:29 tastytrade trivia and theme song history
    55:01 What is the GEX gamma exposure index?
    58:54 2026 S&P 500 predictions from Tom and Scott

    As 2025 closes with the S&P 500 up 17% for the year, investors and professionals alike are reassessing their strategies for building wealth in an uncertain market. With AI stock valuations at historic highs and many experts predicting a correction, understanding options trading strategies like selling upside calls and short strangles has become essential for protecting portfolios. Meanwhile, workers across industries—from executive chefs to attorneys—continue to face the challenge of geographic pay disparities and employers unwilling to recognize true professional worth, making salary negotiation skills and data-driven career tools more critical than ever for anyone preparing for a job change or performance review in 2026.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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) 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
  • How Should I Manage Zero DTE Risk__ _ O.L.D. LIVE! _ 12.30
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle zero DTE options risk management, explaining why reducing position size beats using stop losses based on 15 years of research. The hosts debate whether AI could replace high-paid executives like CMOs and CFOs, with a live poll showing 59% agreement. A caller earning $600K in tech asks about transitioning to running his own investment fund, prompting advice on hedge fund formation costs, capital raising challenges, and the realities of managing other people's money. Additional topics include angel investing in family startups, the gold-silver pairs trade during extreme volatility, and the most actively traded futures pairs for beginners.

    #stockmarket #optionstrading #zerodteoptions #careertransition #hedgefund #aijobs

    TIMESTAMPS

    0:00 Intro
    2:05 Market overview and gold silver action
    5:15 Zero DTE iron condor risk management
    9:05 Stop loss vs reducing position size
    14:00 Investing in a family members startup
    19:10 Managing a losing silver options trade
    24:20 Checklist for starting your own business
    29:10 $600K tech worker considering hedge fund career
    37:20 Can AI replace executive positions
    46:00 Most actively traded pairs trades explained
    50:50 Caller asks about Vanguard ETFs and strategy
    55:30 Trading platforms and premium selling approach
    58:10 Hedging strategies and improving cost basis
    1:02:50 Market update and New Year predictions teaser

    The job market heading into 2026 continues to see tension between AI automation fears and executive compensation debates. This episode highlights how the traditional assumption that AI will replace entry-level workers may be backwards, with arguments that overpaid executive roles could be more efficiently augmented by AI tools. For traders, the current gold and silver volatility with IVR over 120 presents both opportunity and danger, reinforcing timeless lessons about position sizing and risk management that apply whether you are trading zero DTE options or considering a major career pivot into wealth management.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 8 min
  • Silver Pairs Trades, Skew and the 1/3 Rule | O.L.D. LIVE! | 12.29
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down their live gold-silver pairs trade as both metals reverse sharply—gold down $200, silver crashing from $82 to $72. They explain the 1/3 rule for selling credit spreads, why option skew doesn't predict market direction, and how pairs trades statistically reduce risk by 85%. Callers ask about social security timing, home ownership strategies, breaking into financial engineering, and whether being a D1 athlete matters in hiring. Tom and Scott debate the lasting impact of the 2021 meme stock era on financial literacy and retail trading growth.

    #stockmarket #optionstrading #wealthbuilding #career #salary #employment

    TIMESTAMPS

    0:00 Intro
    2:25 Silver crashes from $82 to $72 gold down $200
    6:08 Letters from the Dog Pound social security delay strategy
    10:38 When to take social security break even age
    14:20 Credit spread 1/3 rule and option skew explained
    17:30 Managing short strangles P50 vs probability of profit
    21:05 Market check first major down day in weeks
    24:50 Tax year trade settlement deadlines
    27:30 Sports betting and new age financial literacy debate
    30:45 Was meme stock mania good for young investors
    33:40 First time home buyer age and affordability
    37:05 Home ownership investment vs security
    39:45 Life insurance and financial planning for families
    43:00 Does being a D1 athlete increase your hiring value
    46:30 Dog Pound poll results on meme stocks
    47:10 Social security and self employment strategies
    51:20 Gold silver pairs trade and risk reduction
    54:30 Kevin from Mississippi on options trading with small accounts
    59:30 When to leave your job and go into entrepreneurship
    1:03:00 Electrical engineer considering financial engineering degree
    1:07:20 Market wrap gold silver VIX and closing prices

    As precious metals experience historic intraday swings and year-end volatility spikes, traders are seeking safer strategies while young professionals weigh career pivots into high-demand fields like financial engineering. The debate over meme stock mania's legacy highlights ongoing tension between democratized access and predatory market structure. With 2026 approaching, questions around social security optimization, home affordability for millennials, and the value of alternative credentials in hiring reflect broader economic uncertainty facing today's workforce and investors.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 9 min
  • "Where did you get those shoes?" | O.L.D. LIVE! | 12.24
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol discuss why narrowing your resume to one skill set dramatically increases your chances of landing interviews, with a viewer sharing their success story after applying this advice. The hosts break down how AI now screens resumes for large companies, why over 20% of LinkedIn job postings are fake, and how networking remains the key to accessing hidden opportunities in private equity and hedge funds. Callers ask about security clearances and job valuations, walking into companies unannounced, and the hosts share 37 years of lessons on business partnerships including what makes them work and how disagreements get resolved. Market talk covers Bitcoin volatility dropping by half and what that means for 2026 price expectations.

    #jobsearch #resumetips #networking #career #bitcoin #stockmarket

    TIMESTAMPS

    0:00 Intro and holiday banter
    5:28 Birthday timing and holiday logistics
    8:08 Markets update and slow trading day
    11:19 Position sizing and risk management explained
    15:22 Resume tip that landed an interview
    18:40 AI screening resumes and fake job postings
    23:50 What Tom and Scott agree and disagree on most
    28:43 Caller asks about security clearance valuations
    31:26 Caller asks about 2026 live events
    33:08 Sports talk and Aaron Rodgers
    37:18 Business partnership advice and key lessons
    43:58 Caller from Panama on pilot salary models
    46:06 Scott shows off his P448 sneakers
    47:40 Caller asks about showing up unannounced for jobs
    53:44 Breaking into private equity and hedge funds
    57:07 Market talk on gold, silver, and Bitcoin outlook

    These topics matter now because the 2026 job market continues to challenge applicants with AI-driven resume screening and a high volume of fake postings on major platforms. Professionals seeking roles in finance, private equity, or hedge funds face an increasingly hidden job market where networking outweighs traditional applications. Understanding position sizing for traders and investors remains critical as markets hover near all-time highs while Bitcoin volatility contracts, shifting expected moves for the year ahead. For anyone asking for a raise, negotiating salary, or trying to know their worth, these insights offer practical guidance backed by decades of entrepreneurial experience.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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

    1 hr 3 min
  • Dylan Ratigan Calls Tom & Scott | O.L.D. LIVE | 12.23
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol kick off the holiday week with a packed call-in show covering trading, careers, and startup life. Old friend Dylan Ratigan, former CNBC and MSNBC host who also appeared on tastytrade, calls in from Lake Placid to catch up and shares a wild story about his first brokerage account, turning $10K into $80K on Flowserve calls before losing most of it chasing bigger positions. The hosts break down minimum account sizes for new traders, why $2,000 is the sweet spot for options, and how to protect unrealized gains heading into the new year using covered calls and cashless collars. Callers ask about margin versus leverage, whether we can trust government economic numbers, and how experienced professionals should weigh startup culture against corporate compensation. A UC Berkeley senior gets real advice on startup fundraising challenges at 21, and Bill Ackman's SpaceX SPARC proposal gets a skeptical review.

    #stockmarket #optionstrading #startups #career #trading #investing

    TIMESTAMPS

    0:00 Intro
    2:01 Minimum account size for new traders
    7:21 How much Tom and Scott started with
    9:52 Protecting unrealized gains into 2025
    12:47 Dylan Ratigan calls in from Lake Placid
    15:00 Dylan's first brokerage account disaster
    18:49 Bloomberg terminal pricing stories
    22:07 Can we trust government economic numbers
    27:07 Caller asks about margin vs leverage
    36:26 Lossdog valuation methodology explained
    44:52 Bill Ackman's SpaceX SPARC proposal
    49:30 Finding startup culture as an experienced professional
    51:44 UC Berkeley senior on startup fundraising at 21
    58:07 Market update and holiday schedule

    These topics hit at the core of what professionals and traders are navigating right now. With the S&P closing near record highs and VIX dropping below 14, year-end tax planning and portfolio protection strategies are top of mind. Meanwhile, the 2025 job market continues to present a stark choice between startup culture and corporate compensation, a tension that experienced professionals increasingly feel after years in traditional roles. For young founders, the fundraising landscape remains challenging, with age and network still serving as gatekeepers to capital despite strong technical skills.

    ABOUT ONE LUCKY DOG / LOSSDOG

    One Lucky Dog 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 find yours—and grow it.

    👉 Join the waitlist at https://lossdog.com/

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    1 hr 2 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