The Deep End

PODCAST · business

The Deep End

The Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth and passive income.

  1. 67

    The Truth About Feeling Financially “Behind” | Ep. 66

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into what actually changes as your portfolio grows, and why it doesn’t always feel the way you expect. We also talk about the pressure of feeling financially “behind,” how risk changes as you get older, and the mindset required to keep leveling up.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  2. 66

    What’s REALLY Driving the Stock Market Right Now | Ep. 65

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into what’s been going on in the stock market lately. And more importantly, what might actually be driving it.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  3. 65

    What Most Investors Get Wrong About Diversification | Ep. 64

    ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into what most investors get wrong about diversification. While it’s often seen as a way to reduce risk, too much diversification can actually dilute your best ideas and limit your upside. Throughout the conversation, we talk about how to strike the right balance between diversification and conviction, and how to build a portfolio that truly aligns with your goals.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  4. 64

    The Truth About “Buying the Dip” Right Now | Ep. 63

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into the recent market volatility and share how we’re actually navigating it. We also get into the mindset behind investing, from handling big portfolio swings to why chasing “getting rich” often leads people in the wrong direction.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  5. 63

    Will AI Make Investing Obsolete? | Ep. 62

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into how AI could reshape investing and whether a future where machines run Wall Street might change the way we think about wealth, work, and retirement.We also talk about why most investors struggle, the dangers of chasing quick wins, and why patience and process still matter more than ever.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  6. 62

    The Stock Market Is Crazy Right Now (Why We're Not Worried) | Ep. 61

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into the recent volatility in the stock market and why neither of us are losing sleep over it. We also talk about how long-term investors should think about market swings, the type of fear that often holds investors back, and why staying curious is one of the most important traits you can develop as an investor.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  7. 61

    Is Investing ONLY About Returns? | Ep. 60

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into why most people will lose in the AI era — and it’s not because of the technology itself. From marathon mindset to investing ethics, we break down why discipline and mental strength will matter more than ever.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  8. 60

    How To Become Financially Dangerous | Ep. 59

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsAll of life is compounding, whether you realize it or not. In this episode of The Deep End, we explore the difference between innovators, imitators, and idiots, and why the direction you’re compounding determines everything else in life.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  9. 59

    This Is What Real Financial Freedom Looks Like | Ep. 58

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7SPOTIFY ► https://open.spotify.com/show/5XcHIAxHKaLKlTKCfkeYsV?si=uPY72iLLR_yIJO8uiji2aQAPPLE PODCASTS ► https://podcasts.apple.com/us/podcast/the-deep-end/id1802736592ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we sit down with our friend Ralph — a retiree who completely rebuilt the way he thinks about money, risk, and what financial freedom actually means. If you’ve ever wondered how to build a portfolio you can live with — not just live off — this conversation is for you.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  10. 58

    This Is the Hardest Skill in Investing | Ep. 57

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into why doing nothing is often the hardest (and most valuable) skill in investing, why chasing fast money almost always slows you down, and why timeless principles still matter as products, platforms, and incentives continue to evolve.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  11. 57

    How Small Daily Decisions Compound Into Massive Results | Ep. 56

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we explore why small daily decisions matter more than big, emotional ones, how discipline compounds faster than money, and why committing before motivation shows up is often the real edge.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  12. 56

    How To Start Thinking For Yourself As An Investor | Ep. 55

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7RUSS'S CHANNEL ► https://www.youtube.com/@DapperDividendsARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we’re joined by Russ Knopf for a wide-ranging conversation about something most investors struggle with but rarely admit: learning how to actually think for yourself.We dig into what it really means to be a long-term investor, why being “right” doesn’t always matter, and how focusing on process instead of outcomes can completely change the way you approach investing.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  13. 55

    Successful Investing All Comes Down To This | Ep. 54

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we sit down with our friend Danny Cepero to talk about what successful investing is really all about — and it’s probably not what most people think.Danny shares his story of growing up in Cuba, immigrating to North America, filing for bankruptcy, losing money trying to day trade, and eventually rebuilding everything from scratch.Today, he’s built a six-figure investment portfolio, is on track for early retirement, and—more importantly—has total peace of mind around money.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  14. 54

    How Much Yield Is TOO MUCH Yield? (w/ Spencer Invests) | Ep. 53

    BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7SPENCER'S CHANNEL ► https://www.youtube.com/@SpencerInvestsARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we sit down with Spencer Dunbar (aka Spencer Invests) to talk about the rise of high-yield and weekly dividend ETFs, the growing obsession with income investing, and why so many investors are chasing yield without fully understanding the risks.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  15. 53

    The HARD TRUTH About Income Investing | EP. 52

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodPAUL'S CHANNEL ► https://www.youtube.com/@BetterCallPaul55BE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we’re joined by Paul Santori for an honest conversation about the realities of income investing. We dig into portfolio volatility, the dangers of chasing ultra-high yields, and how Paul’s income strategy has evolved after real drawdowns and real lessons.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  16. 52

    Our Investing Goals For 2026 | Ep. 51

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodBE A GUEST ON THE DEEP END ► https://forms.gle/SqFvoL8xgUnwPuez7ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we close out 2025 by looking back at the investing goals we set for the year and how things actually played out. From there, we lay out our investing goals for 2026 and what we have our sights set on as we head into the new year.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  17. 51

    Mini-Retirements Are the New FIRE — Here’s Why | Ep. 50

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we’re breaking down Retire Often by Jillian Johnsrud and the idea that mini-retirements might make more sense than waiting decades for “traditional retirement.” It’s a different take on FIRE, but the author makes a convincing case that stepping away from work can actually help your career and your finances.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  18. 50

    Is It Time To Buy AI Stocks? (w/ BD Investing) | Ep. 49

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodFOLLOW BD ► https://www.instagram.com/bdinvestingg/ARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we’re joined by Bilaal Dhalech (BD Investing) to talk through one of the biggest questions investors are asking right now: is it time to buy AI stocks? We dive into whether the hype is cooling off, how expectations have shifted, and why recent volatility doesn’t automatically mean the party is over.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  19. 49

    Get Wealthy With These Simple Habits | Ep. 48

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, Ari and I break down the simple daily habits that quietly compound over time and make you a better investor.In this episode of The Deep End, we break down the simple daily habits that quietly compound over time and make you a better investor.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  20. 48

    Most Investors Own Too Many Stocks — Here’s Why | Ep. 47

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we get into a topic a lot of people don’t think about until it’s too late: owning too many stocks. Most investors spread themselves thin without realizing it, and it ends up hurting their performance, their conviction, and even their peace of mind.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  21. 47

    When to Go ALL IN During a Stock Market Crash | Ep. 46

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we talk about when you should go “all in” during a stock market crash, how to keep your emotions from sabotaging your decisions, and why volatility usually ends up creating the best buying opportunities.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  22. 46

    The Hardest Money Truth You Never Learned In School | Ep. 45

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down the hardest money truth most people never learn in school — and why it holds so many investors back. We talk about the mindset that actually builds wealth, why resilience matters more than stock-picking, and how to think about money in a world that’s getting more distracted and more comfortable than ever.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  23. 45

    How Ordinary Investors Can Build Generational Wealth | Ep. 44

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into what it really takes for ordinary investors to build generational wealth. We also talk about how crypto fits (or doesn’t fit) into a lasting wealth strategy, share some personal updates from our own portfolios, and explore why we see investing as an infinite game rather than a race.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  24. 44

    What Smart Investors Are REALLY Doing During Earnings Season | Ep. 43

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we talk about what smart investors are really doing during earnings season — and why focusing on fundamentals matters more than reacting to short-term price moves. We also share a few portfolio updates, our investing goals for the rest of the year, and the mindset that helps us stay patient when everyone else is panicking.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  25. 43

    This Is How You Live Like a BILLIONAIRE | Ep. 42

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down what it really means to “live like a billionaire” — not by spending more, but by designing a life built around freedom, purpose, and experiences. We also talk about money as a tool, overcoming the fear of spending, geo-arbitrage, mini-retirements, and why most people never feel like they have “enough” no matter how big their portfolio gets.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  26. 42

    How Many Stocks Should You Really Own? | Ep. 41

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into one of the biggest questions every investor wrestles with: How many stocks should you actually own. We break down why over-diversification can quietly drag down returns, the difference between comfort and conviction, and how trimming your portfolio can sometimes be the smartest move you make as an investor.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  27. 41

    Why Most Investors Think Too Small | Ep. 40

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we talk about why most investors think too small (and how to break out of that mindset), why being a part of the investing community matters more than ever, and how to play the long game like a billionaire.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  28. 40

    All Our Dividend Income From September | Ep. 39

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down all of our dividend income from September, share the latest moves we’ve made in our portfolios, and talk through what we’ve got planned for October.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  29. 39

    Need More Money To Invest In Stocks? Do This! | Ep. 38

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down why budgeting usually doesn’t work and how simple lifestyle tweaks can free up extra cash to invest without feeling like a sacrifice.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  30. 38

    Investing Is Changed Forever | Ep. 37

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into why investing will never be the same again. From the rise of finance creators and retail investors to the growing pressure on Wall Street, we explore the financial revolution that’s unfolding right now.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  31. 37

    Investing Your Way to a Rich Life | Ep. 36

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we dive into what it really means to live a rich life — and how investing paves the way to get there. We also answer a listener’s great question about financial splurges and whether Pfizer’s (PFE) higher yield makes it a better investment than SCHD.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  32. 36

    All Our Dividend Income From August | Ep. 35

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down all of our dividend income from August, share the latest moves we’ve made in our portfolios, and talk through what we’ve got planned for September.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  33. 35

    How To Find The PERFECT Stocks To Buy | Ep. 34

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down the full process of finding the perfect stocks to buy—from stumbling across great companies in everyday life, to analyzing their financials, and knowing when to pull the trigger. We also talk about avoiding “new investor syndrome,” overcoming cost-basis bias, and why boring businesses often make the best long-term winners.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  34. 34

    Cheap Stocks Are More Expensive Than You Think | Ep. 33

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down why “cheap” stocks are often more expensive than they look, the herd mentality that traps so many investors, and the mindset shift toward quality and compounding that actually leads to financial freedom.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  35. 33

    This Is How To Find the PERFECT Balance In Your Portfolio (with Brandon Beavis) | Ep. 32

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodFOLLOW BRANDON ON YOUTUBE ► https://www.youtube.com/@beaviswealthFOLLOW BRANDON ON BLOSSOM ► https://www.blossomsocial.com/users/Brandon-Beavis__IYn4oiH1ikbFTx2YARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we are joined by Brandon Beavis, co-founder and CMO at Blossom Social. We dive into Brandon’s investing origin story, how to teach the principles of investing and compounding from a young age, and how to strike a healthy balance between investing for the future and enjoying life in the present.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  36. 32

    All Our Dividend Income From July | Ep. 31

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down all of our dividend income from July, share the latest moves we’ve made in our portfolios, and talk through what we’ve got planned for August.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  37. 31

    Time To Sell These Dividend Stocks? | Ep. 30

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we go live to tackle a tough question: is it time to sell Starbucks (SBUX)? This transitions into a broader discussion about dividend safety, payout ratios, balance sheet strength, and how to think through a potential dividend cut.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  38. 30

    5 Things NOT To Do As A New Investor | Ep. 29

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down 5 things NOT to do as a new investor. Whether you’re just getting started or trying to course-correct after a shaky start, this conversation is packed with insights from the lessons we’ve learned the hard way. We cover everything from chasing high-yield dividend income too early, rushing the investing journey, and falling into the over-diversification trap.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  39. 29

    This Is Why We Buy Dividend Stocks | Ep. 28

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we talk about what financial freedom really looks like—and how we’d spend a perfect day living off dividend stocks and passive income. We also share portfolio updates, Ari’s major tax win, and why reaching financial freedom is about more than just sipping coconuts on the beach.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  40. 28

    Know This Before Dividend Investing | Ep. 27

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsBefore you dive into dividend investing, there’s something you need to understand. In this episode of The Deep End, we break down the real difference between dividend investing and income investing—and why chasing high yields can often lead to disappointment.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  41. 27

    All Our Dividend Income From June | Ep. 26

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we break down all of our dividend income from the month of June and reflect on the portfolio milestones we’ve hit along the way—like Ryne’s dividend portfolio officially crossing the $100,000 mark. We talk about what that moment felt like and why the most meaningful part was seeing support from the community.Also, Ari shares how he pulled in $250 in dividend income despite focusing more on high-growth names like UnitedHealth (UNH) and VGT, while Ryne reveals the companies behind his $315 haul—including his first-ever $100+ payment from SCHD.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  42. 26

    New Investors ALWAYS Make This MISTAKE | Ep. 25

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, we talk about one of the biggest and most common mistakes new investors make: not thinking through where they’re investing. We break down the pros and cons of taxable accounts, Roth IRAs, and 401(k)s for dividend growth investors, plus share the mindset shifts that helped us get serious about long-term wealth building.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  43. 25

    The Real Reason Stocks Fall | Ep. 24

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsWhy do great companies like Visa (V) and Zoetis (ZTS) suddenly drop? In this episode of The Deep End, we unpack the real reason stocks fall—and why it often has nothing to do with the earnings, dividends, or anything else related to the business.Note: At around the 1 hour 18 minute mark, we ran into some technical issues that caused the video and audio to get out of sync. Rather than leave in a messy ending, we decided to cut the episode right before the problems started. That’s why the video ends a bit abruptly—we just wanted to let you know what happened. Thanks for understanding, and we’ll be back next week with another full episode!The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  44. 24

    The Right Way To Think About Investing Goals | Ep. 23

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, Ari and Ryne talk about setting meaningful investing goals, staying committed to those investing goals, and celebrating all the "small victories" along the way. They also share big updates to their portfolios and explore how mindset, community, and accountability play a big role in building long-term wealth.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  45. 23

    Should Investors Only Care About Total Return? | Ep. 22

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodFOLLOW CRAIG ON X ► https://x.com/SCHDETFARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, Ari and Ryne welcome their very first guest: Craig Sutton, better known as SCHD Stan.Together, the three dive into a timeless question at the heart of every investing strategy: Should investors only care about total return? Or is there a deeper way to think about long-term success in the stock market—especially for those who prioritize dividend income and the principles of dividend investing?The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  46. 22

    This Is How You Know It's Time To Sell Your Stocks | Ep. 21

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsIn this episode of The Deep End, Ari and Ryne wrestle with a tough question: Should Ryne finally sell his stake in Altria Group (MO)? It's a high-yield Dividend King that has been a core holding—but is it still worth holding on to?We also talk about whether it’s ever possible to reach a state of “investing Nirvana”—that elusive moment when your portfolio feels complete.And lastly, we dive into a listener question: What’s the best ETF for a child’s long-term portfolio—SCHD, or something like VOO or VGT? We break down the differences and share what we’d do in that situation.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  47. 21

    The REAL Cost of Financial Freedom | Ep. 20

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsThe Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  48. 20

    Our WORST Performing Stocks | Ep. 19

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsThe Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  49. 19

    Why Many Investors STRUGGLE To Build Long-Term Wealth | Ep. 18

    The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsThe Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

  50. 18

    Wall Street Is At A TIPPING POINT | Ep. 17

    This episode of The Deep End is presented by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpodARI'S CHANNEL ► https://www.youtube.com/@arigutmanRYNE'S CHANNEL ► https://www.youtube.com/@rynewilliamsThe Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth.The ideas and opinions presented in this video are meant for informational and entertainment purposes only, are not intended to serve as a recommendation to buy or sell any security in any account, and are not an offer or sale of a security. They are also not research reports and are not intended to serve as the basis for any investment decision.

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ABOUT THIS SHOW

The Deep End is your weekly dive into the world of investing, hosted by Ari Gutman and Ryne Williams. Tune into our candid conversations every week as we share our unfiltered thoughts and lessons learned on our way to building wealth and passive income.

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