The Deep End
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.
Author
The Deep End
Category
Podcast website
Latest episode
Jun 29, 2026
Where to listen?
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Episodes
The Hardest Money Truth You Never Learned In School | Ep. 45 15.11.2025 1:21:25
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 hardest money truth most people never learn in school — and why it holds so many investors...
How Ordinary Investors Can Build Generational Wealth | Ep. 44 08.11.2025 1:24:01
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 takes for ordinary investors to build generational wealth. We also talk about how...
What Smart Investors Are REALLY Doing During Earnings Season | Ep. 43 01.11.2025 1:22:27
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...
This Is How You Live Like a BILLIONAIRE | Ep. 42 24.10.2025 1:13:10
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 li...
How Many Stocks Should You Really Own? | Ep. 41 17.10.2025 1:09:45
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 o...
Why Most Investors Think Too Small | Ep. 40 10.10.2025 1:24:00
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...
All Our Dividend Income From September | Ep. 39 02.10.2025 1:08:30
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,...
Need More Money To Invest In Stocks? Do This! | Ep. 38 25.09.2025 1:06:22
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 in...
Investing Is Changed Forever | Ep. 37 18.09.2025 59:44
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 investo...
Investing Your Way to a Rich Life | Ep. 36 11.09.2025 1:02:05
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...
All Our Dividend Income From August | Ep. 35 04.09.2025 1:10:12
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, an...
How To Find The PERFECT Stocks To Buy | Ep. 34 28.08.2025 1:07:31
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...
Cheap Stocks Are More Expensive Than You Think | Ep. 33 21.08.2025 1:04:27
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 ma...
This Is How To Find the PERFECT Balance In Your Portfolio (with Brandon Beavis) | Ep. 32 14.08.2025 1:09:01
The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod FOLLOW BRANDON ON YOUTUBE ► https://www.youtube.com/@beaviswealth FOLLOW BRANDON ON BLOSSOM ► https://www.blossomsocial.com/users/Brandon-Beavis__IYn4oiH1ikbFTx2Y ARI'S CHANNEL ► https://www.youtube.com/@arigutman RYNE'S CHANNEL ► https://www.youtu...
All Our Dividend Income From July | Ep. 31 07.08.2025 1:11:04
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...
Time To Sell These Dividend Stocks? | Ep. 30 31.07.2025 1:17:52
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 d...
5 Things NOT To Do As A New Investor | Ep. 29 24.07.2025 1:05:15
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-c...
This Is Why We Buy Dividend Stocks | Ep. 28 17.07.2025 1:12:17
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 s...
Know This Before Dividend Investing | Ep. 27 10.07.2025 1:08:21
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 dif...
All Our Dividend Income From June | Ep. 26 03.07.2025 1:01:38
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 alo...
New Investors ALWAYS Make This MISTAKE | Ep. 25 26.06.2025 1:07:44
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...
The Real Reason Stocks Fall | Ep. 24 19.06.2025 1:18:06
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—an...
The Right Way To Think About Investing Goals | Ep. 23 12.06.2025 1:21:23
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 c...
Should Investors Only Care About Total Return? | Ep. 22 05.06.2025 1:15:07
The Deep End is brought to you by Blossom. Download for free and see our full portfolios here: https://getblossom.onelink.me/SOfu/thedeependpod FOLLOW CRAIG ON X ► https://x.com/SCHDETF 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 k...
This Is How You Know It's Time To Sell Your Stocks | Ep. 21 29.05.2025 1:12:57
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...
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