One Lucky Dog

One Lucky Dog

By LossdogBusinessEntrepreneurshipInvesting
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One Lucky Dog episodes

  • Balancing Work While Trading Small and Often | O.L.D. LIVE! | 12.22
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol tackle whether stacking multiple college degrees still matters to employers, with Tom emphasizing math skills in finance and the value of choosing candidates with multiple degrees over equivalent competitors. The show dives into the growing trend of interim job offers where employers test-drive candidates for six months before committing, a practice the hosts find somewhat disingenuous despite its increasing prevalence. Callers from India, Maryland, Montreal, and beyond ask about balancing active trading with a 9-to-5 job, the minimum capital raise that makes sense for startups, and whether law school is worth the debt given AI disruption. The hosts also break down why early-stage startup investments should be all equity rather than debt, and share real-time trading insights on silver, gold, and bonds.

    #stockmarket #optionstrading #careertips #salarynegotiation #lawschool #startupfunding

    TIMESTAMPS

    0:00 Intro
    2:09 Show open and Bears football recap
    8:22 Do multiple college degrees matter to employers?
    11:17 Markets update and trading positions
    13:08 Thoughts on wealth and continuous risk-taking
    19:04 Global labor competition and H-1B visa impact
    24:47 Gold silver ratio and shorting precious metals
    31:14 Options strategies with limited capital
    35:23 Trading actively while working a 9-to-5 job
    39:53 Minimum capital raise for Series A funding
    42:43 Interim job offers as the new hiring trend
    46:03 Why startup investments should be all equity
    49:27 Is law school worth it with AI disruption?
    54:00 Markets check and holiday trading schedule
    58:52 Merch store announcement and show wrap

    The job market is shifting power back to employers, creating new hiring practices like interim roles that leave candidates in limbo for months. Meanwhile, aspiring lawyers face real questions about whether three years of law school debt makes sense when AI can handle legal research. For traders and investors, the hosts provide practical guidance on managing active portfolios alongside full-time work, emphasizing that small position sizes and defined risk strategies make it possible for anyone to participate. These topics reflect broader 2025 trends around employment uncertainty, AI disruption in professional fields, and the democratization of trading tools.

    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 1 min
  • Your Maximum Salary Age May Surprise You | O.L.D. LIVE! | 12.18
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle why your earning potential peaks in your mid-30s and what that means for career planning at every age. They break down the 5-7% buying power rule for adding wings to strangles, debate whether lawsuit winnings should fund your business or trading account, and field calls from viewers in Hawaii, Long Island, Salt Lake City, and Canada. Topics include breaking into finance with an SIE license, computer science versus commercial real estate careers, why iron condors work better as one-off trades than core strategy, and how to prove concept on a side business within six months.

    #stockmarket #optionstrading #salarynegotiation #careeradvice #knowyourworth #financialliteracy

    TIMESTAMPS

    0:00 Intro
    2:07 Show open and market overview
    6:56 When to add wings to strangles explained
    9:53 Lawsuit winnings: business or trading account?
    13:36 Computer science vs commercial real estate careers
    16:24 Caller from Hawaii on calendar spread strategy
    20:09 Breaking into finance with an SIE license
    25:21 Best lasagna in Chicago debate
    29:48 Why your salary peaks in your mid-30s
    33:40 Speculating on daily moves in futures options
    38:52 Micron earnings and triple witching setup
    43:23 Career advice for a recent grad in Salt Lake City
    48:38 Caller on compounding returns reality check
    53:43 Animation supervisor building side businesses in Canada
    59:41 Iron condor frustrations and when to mix up strategy

    The job market heading into 2026 continues to challenge workers at every career stage, making it critical to understand when your professional value peaks and how to maximize it. Research shows earning potential typically hits its highest point in the mid-30s before flattening, which has major implications for salary negotiation timing and career risk-taking in your 20s. For those building wealth through trading, capital efficiency and liquidity selection remain essential, especially when navigating leveraged products and futures options. Meanwhile, the rise of AI-powered career tools promises to finally give workers real data on their market value instead of vague salary ranges.

    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 7 min
  • "I am a Recent Purdue Finance Grad..." | O.L.D LIVE! | 12.17
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan tackle salary negotiation, career pivots, and why knowing your number changes everything. A recent Purdue finance grad calls in asking about building a book of business, and the hosts explain why experience matters more than credentials at 22. The show covers which cryptocurrency has the most upside, whether MSTR is finally a reasonable play now that it trades below its Bitcoin holdings, and why firing bad hires early saves more than money. A caller from Chicago asks how Lossdog will actually create worker fairness, and Tom breaks down the difference between asking for more and proving you deserve it. The hosts also dig into Nvidia's trajectory, Oracle's 6% drop on data center news, and why Larry Ellison losing half his net worth in weeks is a cautionary tale for everyone.

    #stockmarket #optionstrading #salarynegotiation #career #bitcoin #knowyourworth

    TIMESTAMPS

    0:00 Intro
    5:08 Which crypto has the most upside
    9:05 Is MSTR finally a reasonable buy
    13:25 How to handle firing a bad hire
    16:14 Investment banking vs tech startup career paths
    17:52 Which asset class to specialize in for trading firms
    20:12 Market update and triple witching preview
    22:22 Purdue finance grad asks about building a book of business
    28:34 Nvidia outlook and when to sell calls against your position
    35:08 How Lossdog creates worker fairness through data
    39:47 Raising capital for a startup with no contacts
    48:06 Crypto investing for beginners without margin
    57:21 Larry Ellison loses half his net worth
    1:01:10 Market wrap and Thursday outlook

    These topics matter now because the job market heading into 2026 remains uncertain, and workers are increasingly asking whether they are underpaid. Salary negotiation skills have become essential as companies tighten budgets and layoffs continue across tech and finance. The conversation around knowing your worth is no longer optional for career advancement. Meanwhile, crypto regulation is evolving, triple witching creates short-term trading opportunities, and high-profile losses like Oracle remind investors that even billionaires make costly mistakes.

    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
  • Dylan Ratigan & DJT (!?!) Debut the Call-In Show! | 12.15
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol kick off the inaugural call-in format of One Lucky Dog with a packed hour of career and market insights. Topics include whether aspiring money managers need a finance degree or if track record trumps credentials, the realities of retail prop trading firms and why the fee structures rarely favor traders, and how gig economy work like Instacart can actually boost your resume by showing hustle. Callers ask about cannabis sector job data following Trumps reclassification news, Fannie Mae and Freddie Mac IPO speculation, and how Lossdog software will weight boutique company experience versus big corporate names. The hosts close with a market breakdown covering post-Fed volatility, sector rotation out of tech into financials, Bitcoin pressure zones, and why triple witching week could set up the biggest risk window through January.

    #stockmarket #optionstrading #bitcoin #careeradvice #salary #investing

    TIMESTAMPS

    0:00 Intro
    2:42 Mailbag: Do You Need a Finance Degree to Manage Money
    7:07 Cannabis Sector Jobs and Reclassification News
    9:20 Retail Prop Firms: Why the Fees Rarely Work
    11:56 Discuss Diner Culture
    14:26 Dylan Ratigan on Entrepreneurship and Fashion
    18:08 Prank Call from Palm Beach
    21:06 College Student Asks About Gig Economy Work
    23:33 Fannie Mae IPO Speculation
    27:04 Dylan Ratigan Returns on Customer-First Business
    31:07 Discuss Career Pivots Without a Degree
    34:04 How Lossdog Weights Boutique vs Corporate Experience
    39:26 Spencer on the Two Gas Pedals of Wealth Building
    43:07 Discuss Raising a Saver Who Invests
    49:30 Market Update: Post-Fed Whipsaw and Sector Rotation
    54:00 Bitcoin Pressure Zones and the 20K Drop Risk
    57:12 Wrap-Up and Call-In Info

    This episode matters now because the job market heading into 2026 is forcing professionals to rethink credentials versus demonstrated results. With AI disrupting traditional career paths and sectors like cannabis potentially opening new employment opportunities, understanding how to position yourself for salary growth is critical. Meanwhile, markets face their first real test of volatility in months as triple witching approaches and sector rotation signals possible weakness in high-flying tech names. Whether you are negotiating a raise, considering entrepreneurship, or managing your own portfolio, the intersection of career strategy and financial literacy has never been more relevant.

    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 t...

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

    1 hr
  • Tom Sosnoff Wants to Talk With You LIVE! Here's Why
    We are launching soon!
    Join the Lossdog waitilist at https://lossdog.com/

    Subscribe to this channel and watch Lossdog's One Lucky Dog LIVE! Call-In show every Monday through Thursday at 10a est. Call 989--LOSSDOG to speak with Tom & Sccott, live.

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

    Know your numbers. Grow your numbers.

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

    4 min
  • Trading and Investing With AI - Pt. 3 | One Lucky Dog 12.10
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol wrap up their three-part series on AI and trading with a deep dive into tokenized validation, instant settlement, and why Chinese AI models like DeepSeek are shaking up Silicon Valley. The hosts break down why Meta may abandon its Llama open-source model, explore the future of digital ecosystems and stable coins, and share hard-won lessons about pivoting in business including their own failed gold mine investment in Mali. The episode also covers Fed rate decision market reaction, the gold-silver ratio hitting historic levels, and why customer feedback matters but should not dictate your strategy.

    #stockmarket #optionstrading #aitrading #crypto #investing #entrepreneurship

    TIMESTAMPS

    0:00 Intro
    12:05 Show preview and poll results on chipping and social media
    14:08 Mailbag: What is Lossdog and is it an AI trading tool
    17:09 When to start building a core portfolio
    20:25 Worst business failures including the Mali gold mine
    26:40 Digital ecosystem risks and single point of failure
    30:22 AI and trading part three: faster settlement cycles
    33:55 Event-driven tokenization and token-based derivatives
    35:00 Tokenized validation eliminates bad actors
    36:40 Tokenized rewards and the future of loyalty programs
    38:30 Regulated digital exchanges and synthetic exposure
    42:00 Chinese AI models: is DeepSeek safe to use
    46:30 Open source vs closed source AI models explained
    50:18 The art of pivoting in business
    57:20 Market talk: Fed rate decision and S&P rally
    1:07:08 Live call-in show announcement starting December 15

    The AI landscape is shifting rapidly as Chinese models demonstrate cost efficiency that American tech giants struggle to match. For traders and investors, understanding tokenized validation and instant settlement is becoming essential as these technologies promise to eliminate counterparty risk and democratize market access. Meanwhile, the debate over open-source versus proprietary AI models has real implications for anyone building technology businesses or managing portfolios in 2025 and beyond.

    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
  • Trading and Investing With AI -- Pt.2 | One Lucky Dog 12.9
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff, Scott Sheridan, and Sol continue their AI and trading series, exploring how artificial intelligence is transforming liquidity sensing, fraud detection, and execution speed for retail traders. The episode dives into ghost job postings and why 18-22% of LinkedIn listings are fake, the traits that define successful entrepreneurs, and what quant firms really look for when hiring. A viewer mailbag covers when AI features will hit mainstream trading platforms, while the hosts debate Australia's new social media ban for users under 16. The negotiation skills segment reveals how most people leave $2.6 million on the table over their careers and how Lossdog's upcoming software aims to fix that.

    #stockmarket #optionstrading #aitrading #negotiation #career #jobsearch

    TIMESTAMPS

    0:00 Intro
    10:33 AI and trading series part two begins
    15:15 Ghost job postings and fake LinkedIn listings
    18:13 Entrepreneur traits and what it takes to succeed
    21:01 What quant firms look for when hiring
    23:39 Founder origin stories coming to the show
    25:26 When AI features will hit trading platforms
    28:16 Real or not segment
    31:00 Liquidity sensing and AI trading tools
    33:39 Fraud and anomaly detection with AI
    36:10 Speed to opportunity and execution technology
    41:17 Digitization and tokenization of assets
    46:52 247 trading and smart contract automation
    51:23 Two-month-old AI startup raises $475M at $4.5B valuation
    53:55 Australia social media ban debate
    57:49 Is AI the new oil
    1:00:06 AI-generated content vs AI-generated reviews
    1:01:06 Honing your negotiation skills
    1:09:46 Market talk and Fed rate decision preview

    The conversation around AI in trading highlights practical applications like real-time liquidity monitoring, outlier detection for fraud prevention, and faster execution pipelines that compress research into milliseconds. With the Fed meeting underway and a 97% probability of a quarter-point rate cut, the hosts share their market positioning heading into the announcement. The negotiation segment connects directly to Lossdog's mission of helping people understand their true market value and stop leaving money on the table.

    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 18 min
  • Trading and Investing With AI | One Lucky Dog 12.8
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan kick off a three-part series on how artificial intelligence is transforming trading and investing for everyday people. They break down over 25 practical ways AI can help with probability-weighted bets, real-time stress testing, volatility forecasting, cross-asset correlation mapping, and dynamic regime detection. The episode also tackles the harder questions around AI ethics, state versus federal regulation, and whether it is too late to invest in AI stocks. Sol joins to discuss stablecoins, the benefits of becoming tech and AI literate, and how Lossdog is building tools to help you determine your professional worth.

    #aitrading #optionstrading #stockmarket #investing #artificialintelligence #wealthbuilding

    TIMESTAMPS

    0:00 Intro
    1:00 Welcome back and Bears game talk
    5:35 Announcing live call-in show starting next week
    7:25 Regulatory oversight and starting Lossdog
    10:40 Navigating a poorly run business
    13:10 Selling your company: auction vs like-minded acquirer
    16:30 Options assignment and time premium protection
    18:20 Why use a stablecoin
    20:45 Work-life balance poll results
    24:40 AI and trading three-part series intro
    27:50 Probability-weighted bets with AI
    29:50 Dynamic regime detection explained
    33:00 Alternative data alpha and tail risk scanning
    36:00 Micro-structure aware execution
    39:00 24/7 global monitoring and cross-asset correlation
    42:00 Real-time stress testing and self-learning models
    44:30 Bias-free decision making and volatility forecasting
    47:30 AI ethics and federal vs state regulation
    52:00 Is it too late to invest in AI stocks
    56:00 Benefits of becoming AI and tech literate
    1:01:40 Market recap: bonds, crypto, and Fed outlook

    This episode arrives as debates heat up around AI regulation, with questions about whether states should create their own policies or wait for federal guidance. For traders and investors, AI tools are now accessible at little to no cost, offering real-time stress testing, smarter hedging, and faster decision-making that was once reserved for institutional players. Meanwhile, the job market increasingly rewards those who understand how to use these tools, making AI literacy a baseline requirement rather than a bonus skill.

    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
  • Work-Life Balance vs. "9-9-6" | One Lucky Dog 12.03
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan go head-to-head on work-life balance versus the intense 996 work culture of 9 a.m. to 9 p.m., six days a week. The debate gets heated as Tom argues that the most valuable employees are those who work the most hours, while Scott pushes back on the idea that everyone should sacrifice personal time for productivity. The hosts also break down what investors really look for in a pitch (hint: it is mostly about you), share hard-won lessons on branding from building thinkorswim and tastytrade, and discuss the prediction markets showing an 86% chance Kevin Hassett becomes the next Fed chair. Plus, callers ask about burnout, pivoting from bad decisions, and whether to pay dividends to investors.

    #stockmarket #optionstrading #worklifebalance #career #fedreserve #branding

    TIMESTAMPS

    0:00 Intro
    1:06 Bears vs Packers betting odds and wide markets
    9:30 Mailbag: When to pivot and blow things up
    13:36 Investor pitch: Do they care about you or the idea?
    18:17 Judging startup competitions at Booth and Cooper Union
    21:55 Burnout: How to avoid it and stay productive
    24:28 Should you pay dividends to investors?
    29:46 Love letters: Checking Tom's freezer for decade-old food
    31:20 Making fun of each other and workplace dynamics
    37:45 Work-life balance vs 996 culture debate
    45:37 4-day work week trial results from the UK
    51:30 Sergey Brin says 60-hour weeks are the sweet spot
    53:00 Fed chair prediction markets: Kevin Hassett at 86%
    58:08 Words of wisdom: Branding lessons from thinkorswim and tastytrade
    1:10:18 Market talk: NASDAQ, bonds, and crypto update

    The debate over work-life balance continues to intensify as Western companies experiment with four-day work weeks while some Asian tech firms push 996 schedules. With layoffs still reshaping the job market in 2024 and AI changing how we think about productivity, understanding your professional worth has never been more important. The Fed chair discussion also comes at a critical time as interest rates remain elevated and bond markets signal uncertainty about future monetary policy.

    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 19 min
  • Investing in Startups & Raising Capital | One Lucky Dog 12.01
    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.

    Tom Sosnoff and Scott Sheridan kick off December with a deep dive into startup investing and raising capital, drawing from their decades of experience building thinkorswim and tastytrade. The episode tackles whether borrowing against home equity for a startup makes sense, key dos and donts for job interviews, and why you should always maximize your 401k match. Tom delivers a pointed rant against tech billionaires advising young people to skip college while hiring exclusively from elite universities. The show closes with market analysis covering bonds, digital assets, and why silver looks overcooked at current levels.

    #startups #investing #entrepreneurship #career #salarynegotiation #stockmarket

    TIMESTAMPS

    0:00 Intro
    1:19 Happy Monday and Bears football recap
    6:34 Peking turkey Thanksgiving review
    13:58 New show time announcement 7 PM ET
    15:40 Mailbag: Should you take a home equity loan for a startup
    19:00 Job interview dos and donts
    24:17 Why you must maximize 401k matching
    25:32 Raising capital vs building your product first
    30:42 Venture capital vs private equity explained
    35:12 Investing in a startup: Key rules
    41:28 When investing in a startup is a bad idea
    48:29 Assessing startup risk: Team market product and financial
    56:16 Anti-college advice rant: Why tech bros are wrong
    59:45 Words of wisdom: Raising capital methods
    1:07:05 Lossdog software preview and features
    1:13:30 Market talk: Bonds digital assets and stock picks

    College remains one of the few institutions offering social mobility for people without wealthy parents, yet billionaire tech founders who attended Stanford and Harvard keep telling young people to skip it. With student debt at record levels and AI threatening entry-level jobs, the debate over higher education ROI has never been more heated. Meanwhile, startup founders face brutal fundraising environments where 97-99% of ventures fail, making the decision to bootstrap versus seek venture capital more consequential than ever. This episode provides practical frameworks for both investing in startups and raising capital, drawing from real experience building multiple successful companies through market crashes.

    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 21 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