Sosnoff on Money

Tom Sosnoff
  • 5.0 (1)
  • Investing

Come see what we are building at lossdog.com I've spent 40 years building platforms, spotting mispriced assets, and creating value where others missed it. I co-founded thinkorswim and tastytrade—two of the world's largest derivatives trading platforms, both acquired for billions. Now I'm focused on the most mispriced asset in the market: you. On this channel, I share what I've learned from decades in finance, trading, and entrepreneurship—the wins, the losses, and what actually matters. I'll talk trading strategies, market dynamics, career optimization, and how to stop leaving millions on the table. --Tom Sosnoff Do you want to talk with me directly? Watch our call-in show, One Lucky Dog LIVE! every Monday through Thursday at 9:30-11am eastern. Call 989--LOSSDOG to ask me about money, markets, employment and entrepreneurship. At @lossdog (YouTube) Hosted on Ausha. See ausha.co/privacy-policy for more information.

  1. Oct 23

    The Scaling Mistake Every Trader Makes

    Join Lossdog at https://lossdog.com and please subscribe to this channel. Casinos have the edge and still cap your bet. Here's why, and what it means for every trade you size. Should you ever size up a trade because you're sure you're right? Tom Sosnoff has traded for 45 years and made over a million trades, and he answers a viewer's question by comparing the four big position sizing systems: fixed fractional, the Kelly criterion, volatility-adjusted sizing, and the Martingale doubling strategy. He shares his exact numbers: buying power as a percentage of net liq for defined and undefined risk trades, daily theta targets, and how total exposure changes with IV rank. He also explains why seven straight losses can wipe out a Martingale trader, and why "genius fails when you trade too big." #optionstrading #trading #positionsizing #riskmanagement #kellycriterion #tomsosnoff #lossdog TIMESTAMPS 0:00 Should you size up on conviction? 0:39 What trading conviction really is 1:04 Fixed fractional position sizing 2:06 Kelly criterion pros and cons 3:04 Volatility-adjusted position sizing 4:02 Martingale: why doubling down fails 5:02 A hybrid sizing discipline 5:40 Exact buying power % by trade type 6:10 Proving concept before sizing up 6:17 How big is too big? 2x vs 10x 7:14 Why trading edges are so tiny 7:28 Why casinos cap your bet size Position sizing decides more trading accounts than stock picking does, and it matters more now that retail traders have easy access to options, leveraged products, and short-dated contracts that can magnify a single oversized bet. The Kelly criterion has spread from professional gambling and quant funds into retail trading and sports betting, but it only works if you know your true edge, and in efficient markets almost nobody does. Strategies that "win often," like averaging down or doubling after a loss, can look great for months before one bad streak ends the account. The math behind trading small, trading often, and scaling risk to implied volatility is the same reason casinos win over time: lots of small bets add up, and survival is the real edge. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    The Scaling Mistake Every Trader Makes

  2. Oct 16

    If You Don’t Understand These 3 Trades, You Don’t Understand Options

    There’s a version of this video where you work the trade while it’s being explained. The Interactive Video Sandbox runs the lesson and the strategy side by side, so you’re building the position as the logic unfolds. Find it under the Learn tab in Tom Sosnoff's newest platform--Lossdog. Lossdog is free. No credit card. No paywall. Just better training. Join here: https://tinyurl.com/IVSLD Then open the Sandbox and run the play yourself. ***************************************************************** 45 years. Over a million trades. Nearly 2/3 of the returns came from three option strategies. Tom Sosnoff breaks down the exact setups he still runs today: naked short puts, credit spreads and covered calls, with the delta, days to expiration and premium targets behind each one. Then he opens up his own portfolio allocation, why a 25 delta put wins about 75% of the time, and why covered calls are cost basis reduction, not income. Options involve risk and are not suitable for all investors. #tomsosnoff #sosnoffonmoney #optionstrading #optionsstrategy #coveredcalls #creditspreads #tastytrade TIMESTAMPS 0:00 Strategy 1: naked short puts 1:14 The 25 delta, 45 DTE put setup 2:10 When to sell a put: cheap stock, high IV 2:29 Strategy 2: credit spreads 3:18 Credit spread strikes and buying power 4:22 Strategy 3: covered calls 5:40 Managing covered calls at 50% profit 6:36 Naked puts in a real portfolio 7:40 Call credit spreads on SPX, QQQ, SPY 8:45 Covered calls at all-time highs 9:48 How to split a portfolio by strategy Selling option premium has gone mainstream, from zero DTE SPX trades to covered call ETFs, and most retail traders pick a strategy without ever learning the mechanics underneath it. Delta, implied volatility rank, buying power and profit-taking rules are what separate a grind-it-out premium selling plan from an account that blows up on one bad week. Hearing how a market maker turned founder sizes these trades and splits them across a real portfolio gives you a benchmark to measure your own approach against. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    If You Don’t Understand These 3 Trades, You Don’t Understand Options

  3. Sep 30

    I Quit Passive Investing, It Made Me Rich

    Join Lossdog at https://lossdog.com and please subscribe to this channel. Real estate, mutual funds and wealth managers are the default wealth advice, and Tom Sosnoff says not a single dollar of his wealth came from any of them. The thinkorswim and tastytrade co-founder breaks down why real estate and packaged investment products rob you of growth: they're illiquid, they offer no real strategy, and they teach you nothing about how markets work. He also calls out the hidden fees and locked-up capital in managed, private market and tokenized funds. Then he walks through his exact portfolio allocation today, 30-40% cash, 30-40% options, 10% stocks and 20% futures, and how implied volatility shifts the whole mix. #lossdog #tomsosnoff #realestate #investing #optionstrading #futurestrading #mutualfunds "Set it and forget it" has become the default playbook for a generation of investors, fueled by the rise of passive index funds, target-date products and a housing market that many treat as a guaranteed savings account. But high transaction costs, carrying costs and the months it can take to sell a home make real estate one of the least flexible places to park capital, especially when markets shift fast. At the same time, Wall Street is pushing private market and tokenized funds to retail investors, often with higher fees and longer lockups. Self-directed traders who understand options, futures, implied volatility and probability have tools to adjust risk on their own terms, which is why the debate between passive investing and active trading matters more than ever in 2026. 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, 8 : 30-10am CT. Hosts Tom Sosnoff, Scott Sheridan and Tony Battista bring decades of trading, entrepreneurial and fintech experience to optimizing our professional and portfolio 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 8 : 30-10am CT 📞 Call in: 989-LOSSDOG 📧 oneluckydog@lossdog.com 🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog Everyone has a number. Lossdog helps you know your number, and grow your number. 👉 Join Lossdog at https://lossdog.com/ Hosted on Ausha. See ausha.co/privacy-policy for more information.

    I Quit Passive Investing, It Made Me Rich

  4. Sep 10

    6 Reasons Even Skeptics Should Learn to Trade

    Join Lossdog at https://lossdog.com and please subscribe to this channel. Tom Sosnoff has traded almost every day for 45 years, and he has no interest in matching a benchmark. He lays out six reasons nearly everyone should learn to trade: the financial literacy you only get when being wrong costs you something, the wiring that makes people sell winners early and ride losers down, why options are the oldest risk-management tool in finance and not casino chips, and the Schwab and JP Morgan data showing retail investors didn't blow themselves up after 2021. He also gets into the earnings-week options trade that quietly drains retail accounts, why hindsight bias stops smart people from ever getting better at decisions, and the one lesson that costs almost nothing when you're young and broke and everything when you learn it rich. #lossdog #tomsosnoff #oneluckydoglive #optionstrading #stockmarket #financialliteracy #selfdirectedinvesting TIMESTAMPS 0:25 Active investing builds literacy 1:09 How your brain destroys wealth 1:29 Why people sell winners too early 2:41 Fast decisions beat smart ones 3:08 Options as insurance, not gambling 3:51 The earnings trade retail keeps losing 5:19 They said retail would blow up 6:23 Retail inflows beat the 2021 peak 7:08 Zero commissions changed everything 8:11 Value even if you trail the index 9:01 Hindsight bias and bad calls that win 10:24 Trading and the owner's mindset 12:15 The one lesson, revealed 12:53 From $100K at 23 to $500M at 36 Retail investing changed shape after October 2019, when commissions on stocks and ETFs went to zero across every major brokerage and fractional shares put the market in reach of anyone with twenty bucks. The 2021 meme stock wave was supposed to be the ceiling, and instead participation kept climbing, with net retail inflows into equities running above that peak five years later. Personal finance is now a graduation requirement in a growing number of high schools, which tells you how much of the wealth gap traces back to financial literacy rather than income alone. The argument here was never that self-directed traders beat the S&P, because most won't. It's that the judgment you build sizing real positions under real uncertainty shows up everywhere else, from negotiating your salary to running a business to what you end up teaching your kids about risk. 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, 8 : 30-10am CT. Hosts Tom Sosnoff, Scott Sheridan and Tony Battista bring decades of trading, entrepreneurial and fintech experience to optimizing our professional and portfolio 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 8 : 30-10am CT 📞 Call in: 989-LOSSDOG 📧 oneluckydog@lossdog.com 🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog Everyone has a number. Lossdog helps you know your number, and grow your number. 👉 Join Lossdog at https://lossdog.com/ Hosted on Ausha. See ausha.co/privacy-policy for more information.

    6 Reasons Even Skeptics Should Learn to Trade

  5. Aug 6

    If You Master Volatility, You Master Money

    Join Lossdog FOR FREE at https://lossdog.com and please subscribe to this channel. Tom Sosnoff spent almost 20 years making markets on the CBOE floor before building two billion-dollar companies — and he credits it all to one thing most investors want nothing to do with: volatility. Here he breaks down four reasons volatility isn't something to dodge but the actual engine behind every smart financial decision, from spotting mispriced assets during market panic to why sustained bull markets can hide dangerous portfolio blind spots. He also gets into how tools like IV rank give retail traders a precision edge that didn't exist 20 years ago. There's also a personal confession — alternative investments he thought were 50/50 bets were actually priced 90/10 against him the whole time. #lossdog #tomsosnoff #oneluckydoglive #sosnoffonmoney #optionstrading #stockmarket #volatilityalert TIMESTAMPS 0:00 What volatility actually is 0:53 4 reasons volatility builds wealth 1:07 Reason 1: Opportunity is rarely obvious 1:55 Real-life mispricing examples 2:42 Reason 2: Detecting systemic risk 3:14 Bull markets hide bad portfolio habits 3:55 The 90/10 mistake (personal story) 4:17 Reason 3: Volatility is predictive 5:02 Trading before the VIX (CBOE pit story) 5:44 Reason 4: Volatility creates efficiency 6:33 Binary events and earnings trades 7:16 Start with IV rank — beginner guide Retail investors now have access to options tools that professional floor traders didn't have 20 years ago — but most of them still treat volatility as a problem instead of an input. The VIX has dominated financial news through multiple market dislocations, yet what implied volatility actually measures rarely gets explained clearly or practically. As options trading volume continues hitting record levels, the gap between traders who understand volatility as a math equation and those who treat it as noise keeps widening. One of the clearest explanations of that gap — and what to do about it. ABOUT ONE LUCKY DOG LIVE! / LOSSDOG One Lucky Dog LIVE! is your daily wake-up call for career and financial clarity—streaming live Monday through Thursday, 8 : 30-10am CT. Hosts Tom Sosnoff, Scott Sheridan and Tony Battista bring decades of trading, entrepreneurial and fintech experience to optimizing our professional and portfolio 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 8 : 30-10am CT 📞 Call in: 989-LOSSDOG 📧 oneluckydog@lossdog.com 🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog Everyone has a number. Lossdog helps you know your number, and grow your number. 👉 Join Lossdog at https://lossdog.com/ Hosted on Ausha. See ausha.co/privacy-policy for more information.

    If You Master Volatility, You Master Money

  6. Jul 17

    11 “Boring” Trading Strategies the top 1% of Retail Traders Use

    Tom Sosnoff is giving away FREE access to his newest fintech platform — plus a FREE CRYPTO REWARD — to the first 50,000 users. Claim your spot before it's gone: lossdog.com If this hits, like, drop a comment, and subscribe — it takes 2 seconds and means everything. Over a million trades. 45 years. And when Tom Sosnoff looked back at all of it, one thing was obvious — the strategies that made the most money were the ones nobody brags about. This video breaks down all 11 of them, with exact strike targets, DTE ranges, probability of profit numbers, and how he manages each trade. He also reveals the two strategies that account for more than 70% of his profits — and the specific mistakes that cause most traders to blow them. #optionstrading #tomsosnoff #sosnoffonmoney #lossdog #shortstrangle #jadelize #optionsstrategies TIMESTAMPS 0:00 1 million trades, 1 pattern 0:28 Strategy 1: Short Puts 1:17 Strategy 2: Jade Lizard 2:24 Strategy 3: Covered Calls 4:01 Strategy 4: Short Put Spreads 5:20 Strategy 5: Put Ratio Spreads 6:39 Strategy 6: Short Call Spreads 8:06 Strategy 7: Broken Wing Butterfly 9:33 Strategy 8: Unbalanced Iron Condor 11:04 Strategy 9: Iron Condor 12:07 The 70% reveal 12:13 Strategy 10: Short Strangles 13:55 Strategy 11: Price Reversion & Pairs Trading Most traders spend years chasing complex setups before figuring out what professionals have known forever — implied volatility structurally overstates realized volatility, which means premium sellers have a built-in edge. The strategies here aren't new or exotic. They're the ones that hold up across decades, different market regimes, and asset classes from equities to futures options. The real edge isn't the strategy itself. It's the discipline to trade it correctly, size it right, and keep positions non-correlated — which is exactly what this video gets into. More trader tools at lossdog.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

    11 “Boring” Trading Strategies the top 1% of Retail Traders Use

  7. Jun 20

    If You Are Ambitious But Stuck ... Watch This

    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel. Tom Sosnoff has built four companies with nine and ten-digit exits — and in this video he breaks down the 10 career practices he'd hand to anyone starting out or recalibrating right now. From why chasing the highest salary early on is the wrong move, to the overlooked power of likability over credentials, to why wealth is almost always a byproduct of longevity and not a sprint. Real advice, no fluff, from someone who started on Wall Street as a poli-sci major and ended up changing how millions of people trade. #lossdog #tomsosnoff #oneluckydoglive #careertips #salarynegotiation #jobsearch #financialfreedom TIMESTAMPS 0:00 Intro — Tom Sosnoff on AI and your career 0:36 #1 Own your situation 1:11 #2 Be open to adjacent opportunities 2:09 #3 Don't be seduced by more money 2:43 #4 Prioritize networking 3:20 #5 Articulate your pitch 4:00 #6 Crawl before you walk 4:50 #7 Be flexible — always say yes 5:43 #8 Be smart, but be likable 6:47 #9 Wealth is a byproduct of longevity 7:46 #10 Differentiate yourself 9:06 Tom's top 3 picks from the list The job market is shifting faster than most people's career plans can keep up with — AI is compressing timelines, flattening hierarchies, and making credentials matter less than adaptability. Tom Sosnoff has lived through multiple versions of this disruption and used each one to build something bigger. The practices he shares here aren't theoretical — they're the same ones he's applied across thinkorswim, tastytrade, and now Lossdog, and the same ones he's given his own kids. In a market where everyone is trying to stand out, the candidates who know how to tell their story, build real relationships, and stay flexible are the ones who actually get hired — and actually get ahead. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    If You Are Ambitious But Stuck ... Watch This

  8. Jun 5

    I Trained My Mind To Be Unconventional — It Made Me Rich

    Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel. Tom Sosnoff breaks down the seven mindset principles behind every major deal, company, and trade he's ever made—and none of them are what most people expect. He gets into why always saying yes beats waiting for the perfect deal, how to love the trades you hate, why math should always be your tiebreaker, and how goodwill became the foundation of thinkorswim and tastytrade. If you've ever hesitated on a decision or burned a bridge you didn't need to, this one hits different. #lossdog #tomsosnoff #careermindset #entrepreneurship #optionstrading #tastytrade #thinkorswim 0:00 Intro — The mindset behind every big win 0:27 Rule 1: Be the first to say yes 1:20 Rule 2: Get comfortable being uncomfortable 1:45 Rule 3: The math always wins 2:43 Rule 4: Never blow up a relationship 3:25 Rule 5: Be open and real 3:57 Rule 6: Embrace trust and goodwill 4:39 Rule 7: Be a contrarian 5:09 The two rules that mattered most The principles Tom shares here run counter to how most professionals are taught to make decisions—slow down, be thorough, protect yourself. But in fast-moving markets and competitive business environments, hesitation is often the costliest move. The idea that a bad deal beats no deal, or that you should "love the trades you hate," is rooted in probability theory and decades of market-making experience. In a job market and economy where opportunity windows close fast and relationships compound over years, these seven rules aren't just trading philosophy—they're a framework for how careers and companies actually get built. Hosted on Ausha. See ausha.co/privacy-policy for more information.

    I Trained My Mind To Be Unconventional — It Made Me Rich
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About

Come see what we are building at lossdog.com I've spent 40 years building platforms, spotting mispriced assets, and creating value where others missed it. I co-founded thinkorswim and tastytrade—two of the world's largest derivatives trading platforms, both acquired for billions. Now I'm focused on the most mispriced asset in the market: you. On this channel, I share what I've learned from decades in finance, trading, and entrepreneurship—the wins, the losses, and what actually matters. I'll talk trading strategies, market dynamics, career optimization, and how to stop leaving millions on the table. --Tom Sosnoff Do you want to talk with me directly? Watch our call-in show, One Lucky Dog LIVE! every Monday through Thursday at 9:30-11am eastern. Call 989--LOSSDOG to ask me about money, markets, employment and entrepreneurship. At @lossdog (YouTube) Hosted on Ausha. See ausha.co/privacy-policy for more information.

Information

  • Creator
    Tom Sosnoff
  • Years Active
    2026
  • Episodes
    16
  • Rating
    Clean
  • Copyright
    © Tom Sosnoff
  • Show Website
    Sosnoff on Money

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