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The Deep End
The Deep End
46 episodes
3 days ago
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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Investing
Business
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All content for The Deep End is the property of The Deep End and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Investing
Business
Episodes (20/46)
The Deep End
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/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 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.

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3 days ago
1 hour 9 minutes 11 seconds

The Deep End
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/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 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.

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1 week ago
1 hour 21 minutes 25 seconds

The Deep End
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/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 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.

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2 weeks ago
1 hour 24 minutes 1 second

The Deep End
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/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 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.

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3 weeks ago
1 hour 22 minutes 27 seconds

The Deep End
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/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, 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.

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1 month ago
1 hour 13 minutes 10 seconds

The Deep End
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/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 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.

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1 month ago
1 hour 9 minutes 45 seconds

The Deep End
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/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.


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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1 month ago
1 hour 24 minutes

The Deep End
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/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 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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1 month ago
1 hour 8 minutes 30 seconds

The Deep End
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/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 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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2 months ago
1 hour 6 minutes 22 seconds

The Deep End
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/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.


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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2 months ago
59 minutes 44 seconds

The Deep End
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/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 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.

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2 months ago
1 hour 2 minutes 5 seconds

The Deep End
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/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 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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2 months ago
1 hour 10 minutes 12 seconds

The Deep End
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/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,” 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.

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2 months ago
1 hour 7 minutes 31 seconds

The Deep End
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/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 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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3 months ago
1 hour 4 minutes 27 seconds

The Deep End
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/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.youtube.com/@rynewilliams


In 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.

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3 months ago
1 hour 9 minutes 1 second

The Deep End
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/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 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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3 months ago
1 hour 11 minutes 4 seconds

The Deep End
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/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.


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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3 months ago
1 hour 17 minutes 52 seconds

The Deep End
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/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 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.

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4 months ago
1 hour 5 minutes 15 seconds

The Deep End
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/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 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.

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4 months ago
1 hour 12 minutes 17 seconds

The Deep End
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/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 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.

Show more...
4 months ago
1 hour 8 minutes 21 seconds

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.