The Deep End

40 Episodes
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By: 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.

What Smart Investors Are REALLY Doing During Earnings Season | Ep. 43
Yesterday at 7:52 PM

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 ye...


This Is How You Live Like a BILLIONAIRE | Ep. 42
10/24/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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...


How Many Stocks Should You Really Own? | Ep. 41
10/17/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 port...


Why Most Investors Think Too Small | Ep. 40
10/10/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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.


All Our Dividend Income From September | Ep. 39
10/02/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 presente...


Need More Money To Invest In Stocks? Do This! | Ep. 38
09/25/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 me...


Investing Is Changed Forever | Ep. 37
09/18/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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.



Investing Your Way to a Rich Life | Ep. 36
09/11/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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...


All Our Dividend Income From August | Ep. 35
09/04/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 presente...


How To Find The PERFECT Stocks To Buy | Ep. 34
08/28/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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...


Cheap Stocks Are More Expensive Than You Think | Ep. 33
08/21/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 id...


This Is How To Find the PERFECT Balance In Your Portfolio (with Brandon Beavis) | Ep. 32
08/14/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


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ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In this episode of The Deep End, we are joined by Brandon Beavis, co-found...


All Our Dividend Income From July | Ep. 31
08/07/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 presente...


Time To Sell These Dividend Stocks? | Ep. 30
07/31/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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.


5 Things NOT To Do As A New Investor | Ep. 29
07/24/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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...


This Is Why We Buy Dividend Stocks | Ep. 28
07/17/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 m...


Know This Before Dividend Investing | Ep. 27
07/10/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


Before 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 id...


All Our Dividend Income From June | Ep. 26
07/03/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 fel...


New Investors ALWAYS Make This MISTAKE | Ep. 25
06/26/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 invest...


The Real Reason Stocks Fall | Ep. 24
06/19/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


Why 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.


...


The Right Way To Think About Investing Goals | Ep. 23
06/12/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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...


Should Investors Only Care About Total Return? | Ep. 22
06/05/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


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ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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 timele...


This Is How You Know It's Time To Sell Your Stocks | Ep. 21
05/29/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


In 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?



The REAL Cost of Financial Freedom | Ep. 20
05/22/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


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.


The...


Our WORST Performing Stocks | Ep. 19
05/15/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


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.


The...


Why Many Investors STRUGGLE To Build Long-Term Wealth | Ep. 18
05/08/2025

The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


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.


The...


Wall Street Is At A TIPPING POINT | Ep. 17
05/01/2025

This episode of The Deep End is presented by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod


ARI'S CHANNEL ► https://www.youtube.com/@arigutman


RYNE'S CHANNEL ► https://www.youtube.com/@rynewilliams


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.


Th...


The Lonely Chapter of Investing | Ep. 16
04/24/2025

FOLLOW US HERE 👇Ari'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 ar...


This Is The REAL REASON You Have A Job | Ep. 15
04/17/2025

FOLLOW US HERE 👇Ari'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 ar...


Stocks Are SKYROCKETING Again (For Now) | Ep. 14
04/10/2025

FOLLOW US HERE 👇Ari'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 ar...


Our Portfolios Are DROPPING FAST | Ep. 13
04/03/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


It's Time For Investors To DIG IN | Ep. 12
03/18/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


How To Stay Strong When The Market Is TANKING | Ep. 11
03/18/2025

FOLLOW US HERE 👇Ari'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 ar...


Why You Need The Marathon Mindset To Build Wealth | Ep. 10
03/18/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


This Is When You'll Notice The Snowball Effect | Ep. 9
03/18/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


Does "The American Dream" Still Exist? | Ep. 8
03/18/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


Why Technology Stocks Could Soar In 2025 | Ep. 7
03/17/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


Why We Will NEVER "Retire" | Ep. 6
03/17/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


How To Help Others Start Investing | Ep. 5
03/17/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...


The First Stocks We Are Buying In 2025 | Ep. 4
03/17/2025

FOLLOW US HERE 👇

Ari's Channel ► https://www.youtube.com/@arigutman

Ryne's Channel ► https://www.youtube.com/@rynewilliams


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.


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...