One Lucky Dog

One Lucky Dog

By LossdogBusinessEntrepreneurshipInvesting
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One Lucky Dog episodes

  • Stop Blowing Up Accounts: Portfolio Margin + Realistic Returns | One Lucky Dog - 11.27
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan take calls on this special Thanksgiving episode covering realistic return expectations, portfolio margin strategy, and the costly mistakes that blow up accounts. A caller shares how he turned $80K into $250K in under a year and asks when to scale a winning strategy into a fund. Another caller with a history of account blowups in 2000, 2008, and 2022 asks whether targeting 20% annual returns is realistic. Tom breaks down his Oracle earnings trade that went wrong and explains IV rank versus IV percentile for newer traders.

    #optionstrading #stockmarket #portfoliomanagement #tradingstrategy #investing #riskmanagement

    TIMESTAMPS

    0:00 Intro
    1:15 Show format and schedule change to 6 PM
    1:50 Turning $80K into $250K in 8 months
    4:05 When to scale a strategy into a fund
    5:05 Account size matters for scaling
    6:40 Portfolio margin as a tool not a requirement
    8:15 Tom and Scott trading styles compared
    11:55 History of blowing up accounts in bear markets
    14:55 Realistic 18-20% annual return expectations
    16:50 IV rank versus IV percentile explained
    19:45 Oracle earnings trade breakdown
    23:00 Yen trade and range-bound strategy

    These topics hit at the core of what retail traders struggle with most heading into 2026: knowing when to size up, understanding realistic return targets, and avoiding the account blowups that wipe out years of gains. With volatility compressing and many traders sitting on gains from the post-2022 rally, questions about portfolio margin and scaling strategies are more relevant than ever. The discussion of IV rank versus IV percentile clarifies a common point of confusion for anyone transitioning between platforms or learning options for the first time.

    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.

    26 min
  • Stock Buybacks, Pumps and Dumps | One LuckyDog 11.26 - Evening Show
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down the hidden dynamics of stock buybacks and call out AI company CEOs who pump their stock while quietly selling millions in shares. The hosts explore when buybacks signal financial strength versus short-term manipulation, why good companies cost money to acquire, and how executive compensation incentives can misalign with investor interests. Sol guides viewers through career pivot strategies and reveals how Lossdog's new software maps transferable skills across seven industries. The episode also tackles mailbag questions on borrowing against Bitcoin versus home equity, job-hopping red flags, and raising capital as a first-time founder.

    #stockmarket #optionstrading #stockbuybacks #aistocks #nvidia #careerpivot

    TIMESTAMPS

    0:00 Intro
    1:28 Show opens with synthetic Friday banter
    9:25 Mailbag segment begins
    14:55 Borrowing against Bitcoin vs house
    16:47 Stock volatility and job opportunities
    19:23 Job hopping red flags and the 10-year rule
    22:40 Raising capital as a first-time founder
    26:44 Taking risk at work in a Fortune 500 company
    30:17 Unleashed segment on stock buybacks
    37:27 Pros and cons of corporate buybacks
    48:07 Bad Dog rant on CEOs pumping their stock
    54:24 Words of wisdom on career change and transferable skills
    1:02:43 Market talk and tale of the tape
    1:09:56 Thanksgiving side dish favorites and sign off

    The debate over stock buybacks intensifies as companies sit on record cash reserves while workers question wage growth and long-term investment priorities. With AI valuations facing scrutiny after Nvidia and AMD earnings calls sent stocks tumbling despite bullish CEO commentary, investors are learning to watch what executives do rather than what they say. Meanwhile, the job market remains uncertain heading into 2026 as tariff concerns and economic volatility shape hiring decisions across industries.

    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 13 min
  • Stock Buybacks | One Lucky Dog - 11.26
    We are launching soon!
    Join the Lossdog waitilist at https://lossdog.com/

    Subscribe to this channel and watch Lossdog's One Lucky Dog show live every Monday through Wednesday at 11a est.

    Follow Lossdog:
    X (Twitter): https://x.com/wearelossdog
    Instagram: https://www.instagram.com/wearelossdog/
    Linkedin: https://www.linkedin.com/company/lossdog/

    Most professionals have no idea if they’re being paid fairly—and the system is designed that way. Outdated salary ranges, vague job boards, and guesswork leave 68% of workers feeling undervalued .

    Lossdog changes that. In just minutes, you can:
    ✅ Upload your resume
    ✅ Chat with our AI coach
    ✅ Get your real, data-backed number—your whole professional worth.

    No vague ranges. No crowdsourced chaos. Just clarity, confidence, and a roadmap for your next move.

    Stop guessing. Start Lossdog.

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

    1 hr 13 min
  • College or Not? | One Lucky Dog - 11.25 evening show
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle the heated debate over whether college is still worth it, revealing that 25% of unemployed workers in a key demographic hold college degrees while lifetime earnings still favor graduates by $1.2 million. The hosts break down alternatives like trade schools and boot camps, share personal stories about applying to just one college, and explain how the upcoming Lossdog software will let users compare salary projections across different career paths. The episode also features a rant on 50-year mortgages and why financial paternalism hurts working families, plus market analysis covering Google's post-earnings volatility and weakness in AMD and Nvidia.

    #stockmarket #collegeeducation #careeradvice #salarynegotiation #financialliteracy #jobmarket

    TIMESTAMPS

    0:00 Intro
    6:07 Mailbag: Lossdog software for consultants
    8:45 Will the show cover trading and markets
    11:00 Where the name Lossdog came from
    13:51 Using Lossdog to explore career paths
    18:48 College or not debate begins
    24:01 Does college matter on a resume
    27:36 Real or not: Grandma gets air tagged
    30:40 AI submits fake citations in court
    32:42 South Korea halts markets for college exams
    34:28 Cost versus return of college education
    39:17 Alternatives: trade school and boot camps
    43:53 Bad Dog rant: 50-year mortgages
    48:33 Words of Wisdom: growth mindset
    53:39 Seeing effort as necessary for success
    59:04 Learning from feedback and criticism
    1:04:36 Being inspired by others success
    1:06:56 Lossdog hurdles feature preview
    1:10:48 Market talk: Google, Nvidia, AMD moves

    The college versus career debate has never been more relevant as unemployment among degree holders rises while student debt reaches record levels. With the job market shifting rapidly due to AI and automation, understanding the true return on investment of higher education is critical for anyone making career decisions in 2026. The hosts draw from decades of experience building thinkorswim and tastytrade to offer practical perspective on networking, skill development, and the intangible benefits of education that go far beyond textbooks.

    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 20 min
  • Should You Go to College? The $1.2M Lifetime Earnings Gap - 11.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle one of the most debated questions in career planning: is college still worth it? The hosts break down the hard numbers, revealing that college graduates earn $1.2 million more over their lifetime than high school grads, with unemployment rates nearly half that of non-graduates. They push back hard against the anti-college narrative, arguing that the networking, soft skills, and personal growth from four years of higher education pay dividends far beyond what any spreadsheet can capture. The episode also features a fiery rant on 50-year mortgages and why financial paternalism is holding back working families, plus real-time market analysis as the S&P swings 80 handles and Google gives back its morning gains.

    #stockmarket #collegeeducation #careeradvice #salary #financialliteracy #investing

    TIMESTAMPS

    0:00 Intro
    9:45 Mailbag: Will Lossdog work for consultants
    12:00 Show moving to 6 PM Central time
    14:30 Mailbag: Where did the name Lossdog come from
    17:00 Mailbag: 20-year-old student choosing a major
    22:48 Mailbag: Do you still actively trade
    27:35 Real or Not: Grandma gets air tagged
    29:00 Real or Not: $1,000 coffee in Dubai
    30:20 Real or Not: Trump tariffs on Trump products
    31:05 Real or Not: AI submits fake court citations
    31:55 Real or Not: South Korea halts markets for college exams
    33:45 College or Not: The cost versus return breakdown
    41:15 Making the right education choice
    49:15 College pros and lifetime earnings data
    54:40 Bad Dog: 50-year mortgages rant
    57:45 Words of Wisdom: Growth mindset
    1:11:20 Market Talk: Google, Nvidia, and wild volatility

    The college debate has never been more relevant as young professionals weigh rising tuition costs against uncertain job markets. With unemployment for college grads at 2.5% versus 4.2% for high school grads, and lifetime earnings gaps exceeding seven figures, the data tells a clear story even as social media influencers push alternative paths. This episode cuts through the noise with real numbers and decades of hiring experience from two entrepreneurs who have built multiple successful companies.

    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 20 min
  • Why Your PhD Might Be Killing Your Job Search - 11.24.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle the PhD job hunt dilemma, debating whether removing advanced degrees from resumes helps or hurts candidates. The hosts break down what makes a strong leader, emphasizing trust over vision and the importance of reading the room. Tom delivers a pointed rant on mega billionaires who prioritize material wealth over meaningful legacy, arguing that history honors what you gave up, not what you piled up. The episode also covers MBA timing strategy, stocks versus crypto at current levels, and the top five qualities that separate outliers from everyone else.

    #stockmarket #optionstrading #leadership #career #salary #jobsearch

    TIMESTAMPS

    0:00 Intro
    1:42 Show open and weekend recap
    5:20 Bulls game and Bears betting update
    7:51 Thanksgiving cooking plans
    13:00 Schedule change announcement for next week
    14:57 Mailbag: Should I remove my PhD from my resume?
    21:56 MBA timing: right after college or work first?
    24:06 Semester abroad versus internship debate
    26:34 Stocks or crypto: which is cheaper right now?
    27:52 Using AI to tailor your resume
    31:10 Unleashed: What makes a strong leader
    37:04 Reading the room as a leadership superpower
    41:24 How to build leadership skills
    44:06 Prediction markets on tech CEO departures
    47:26 Bad Dog: Mega billionaires as legacy losers
    51:57 Words of wisdom: Top five qualities of an outlier
    54:36 Outlier quality: communicate without ego
    57:14 Be personable, genuine, and humble
    1:01:34 Outlier quality: make decisions quickly
    1:05:05 Lossdog technology preview
    1:06:40 Market Talk: S&P, NASDAQ, and crypto moves
    1:13:15 Closing remarks and upcoming schedule

    This episode arrives as job seekers navigate a challenging market where AI screening tools and keyword optimization have become essential resume strategies. The leadership discussion is timely as companies increasingly value emotional intelligence and adaptability over traditional command-and-control management styles. With tech layoffs continuing and career pivots becoming more common, understanding what differentiates outliers from average performers has never been more relevant for professionals at every level.

    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 15 min
  • Why Likability Is the Most Underrated Career Skill- 11.19.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan dive deep into the world of private company investing, revealing why companies now stay private for 10 to 14 years instead of four to six and what that means for everyday investors. The hosts break down IPO prediction markets for companies like OpenAI, Anthropic, and Discord, while sharing hard-won lessons from their own experiences getting rejected by private equity firms. The conversation covers likability as an underrated professional trait, using AI to improve your resume without getting caught, and why creating challenges is the foundation of company culture. Tom delivers a pointed rant on Treasury Secretary Scott Bessent, and the show wraps with market analysis on the recent 35% Bitcoin pullback and what it signals for digital assets.

    #stockmarket #optionstrading #privateequity #bitcoin #careertips #investing

    TIMESTAMPS

    0:00 Intro
    15:12 Show begins
    23:31 Mailbag on likability as a career skill
    27:12 Social media apps the hosts actually use
    30:15 Mobile app and podcast launch announcement
    30:44 Learning to make quicker decisions without trading
    35:00 Food reviews and fried chicken showdown
    36:44 LinkedIn app design critique
    36:58 Using AI to improve your resume
    40:47 Mailbag on brutal honesty
    41:10 Investing in non-public companies
    49:20 Why private equity firms miss great deals
    53:04 AI company valuations and competitive pressures
    55:40 IPO prediction markets for OpenAI, Discord, Anthropic
    58:55 Rant on Treasury Secretary Scott Bessent
    1:03:40 Challenges segment on building culture
    1:12:00 Lossdog grade feature preview
    1:14:35 Market talk on Bitcoin and digital assets
    1:24:35 Stock market outlook and Nvidia earnings

    The private company investing landscape is shifting dramatically as regulatory changes, ETFs, and platforms like Click IPO open doors that were previously locked behind accredited investor requirements. With $13 trillion in private markets and companies like OpenAI potentially going public within the next year, understanding this space has never been more relevant. The hosts connect these investment opportunities to broader themes of knowing your professional worth and building confidence through challenges.

    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 31 min
  • The $440K AI Consulting Scandal Every Professional Must Know - 11.18.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol tackle the Deloitte AI scandal that exposed $440,000 in questionable consulting fees, sparking a broader conversation about how AI is disrupting professional services while costs remain sky-high. The hosts break down why legal fees have ballooned to $2,750 per hour despite AI doing much of the work, and share their bone to pick with job seekers who bury their best qualities under pages of irrelevant credentials. The episode also covers when to take the leap into entrepreneurship, why articulation is a make-or-break skill, and a market rundown ahead of Nvidia earnings.

    #stockmarket #optionstrading #artificialintelligence #career #salary #jobsearch

    TIMESTAMPS

    0:00 Intro
    15:30 Show open and studio tour
    18:50 Venezuelan food discovery
    26:05 Mailbag: When to start your own business
    28:50 Is 40 too late to start over
    31:00 Building a meaningful business with purpose
    34:20 What Lossdog is building
    36:15 Real or not game segment
    41:30 AI changing professional services
    45:00 The $440K Deloitte AI scandal
    47:10 AI hallucinations in legal cases
    49:30 AI market growth from $40B to $1.3T
    53:20 AI killing entry-level jobs debate
    55:30 Caller Tim Knight on AI and chart analysis
    1:01:30 Resume oversharing rant
    1:07:50 Words of wisdom on articulation
    1:11:50 Stay narrow and set reasonable expectations
    1:22:00 Market talk and Nvidia earnings preview

    The Deloitte scandal highlights a critical inflection point in professional services where AI adoption is accelerating but cost savings are not being passed to clients. With 66% of workers admitting they rely on AI output without verification and 120 documented legal AI hallucination cases since 2023, the tension between efficiency gains and accountability is intensifying. For job seekers, the six-second resume scan reality means every irrelevant credential dilutes your chances, making focused positioning more valuable than ever in a competitive 2026 job market.

    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 31 min
  • Why Lower Interest Rates Actually Widen the Wealth Gap- 11.12.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan break down why lower interest rates actually benefit the wealthy more than everyone else, challenging the common narrative that rate cuts help all Americans equally. The hosts also tackle whether sports betting and prop bets are compromising professional sports integrity, share their words of wisdom on why success is earned through longevity and staying in your lane, and preview the Lossdog skills diagram feature. Additional topics include job hopping red flags, the value of loving your work even if underpaid, and why bootstrapping beats buying when starting a business.

    #stockmarket #optionstrading #wealthbuilding #career #interestrates #sportsbetting

    TIMESTAMPS

    0:00 Intro
    15:25 Show opens with Mexico City food stories
    23:03 Tom Sosnoff's CNBC appearance and morning trading routine
    26:05 One Lucky Dog show overview and schedule
    28:09 Mailbag: Mexico City money manager question
    29:17 Mailbag: Sold restaurant, bootstrap or buy next?
    31:40 Mailbag: Is knowing your worth important if you love your job?
    34:10 Mailbag: Does job hopping hurt your career?
    37:36 Viewer feedback and show adjustments
    41:00 Will lower interest rates widen the wealth gap?
    51:15 Sports betting and prop bets compromising sports integrity
    1:01:30 Words of wisdom: Success is earned
    1:06:23 Scott Sheridan on stay in your lane and avoid going too broad
    1:11:40 Success requires longevity
    1:15:41 Never shy away from risk and own your decisions
    1:19:33 Lossdog software preview: Skills diagram
    1:21:42 Market update and current trading positions

    The wealth gap conversation matters now more than ever as the Fed continues adjusting interest rates in 2025. With markets at all-time highs and debates swirling about who benefits from monetary policy, understanding the real impact of rate changes on different income levels is essential knowledge for anyone building wealth. Meanwhile, the sports betting industry faces increased scrutiny following recent scandals involving NBA and MLB players, raising questions about the integrity of professional sports in the era of legal gambling.

    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 31 min
  • The $3.6M You're Leaving on the Table Over Your Career - (Debut Ep.) 11.10.25
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan debut their brand new show One Lucky Dog, broadcasting live from their custom-built Chicago studio. The thinkorswim and tastytrade founders dive deep into self-differentiation strategies, the importance of leverage and risk-taking in building wealth, and why making quick decisions separates successful people from everyone else. They unveil a first look at the Lossdog software platform designed to calculate your true market value and reveal how much you might be leaving on the table over a lifetime. The episode also features a pointed rant on presidential pardons and crypto conflicts, plus caller questions about betting on yourself when you have no safety net.

    #stockmarket #career #salary #wealthbuilding #risktaking #selfworth

    TIMESTAMPS

    0:00 Intro
    15:10 Show kicks off from the new Chicago studio
    16:37 Tom Sosnoff reveals he’s officially barrette-less
    23:50 Show format and how to call in
    29:30 News You Can't Use and Real or Onion game
    34:20 Cameroon elects 92-year-old leader
    37:40 Denmark zoo asks for pets as animal food
    40:10 Robot umpires and sports officiating debate
    44:30 Unleashed segment on fiscal responsibility
    50:00 Why learning risk-taking beats fiscal conservatism
    57:50 First caller ever Tano from Atlanta
    59:30 Bad Dog rant on presidential pardons and crypto
    1:07:20 Words of Wisdom on self-differentiation
    1:12:00 Making quick decisions in business and life
    1:22:50 Sneak peek at Lossdog salary technology
    1:29:20 Caller TJ asks about taking risks without a safety net
    1:33:30 Market talk and Tesla pay package controversy
    1:47:47 Final caller Paul on CEO vs teacher salaries

    These topics matter now more than ever as the wealth gap continues to widen and workers struggle to understand their true market value. With AI transforming industries, job markets shifting rapidly, and executive compensation reaching unprecedented levels like the trillion-dollar Tesla pay package, professionals need tools and knowledge to negotiate from strength. The debut of Lossdog's salary calculation technology aims to democratize the kind of market intelligence that has traditionally been available only to employers and recruiters.

    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
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    1 hr 53 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