Back to the Basics: How to Manage Your Portfolio Without Overthinking It

14 May 2026 · 50 min · 17 chapters

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In short

Portfolio management “back to basics” for long-term investors—diversification, position sizing/allocation, entry rules, dollar-cost averaging, and disciplined trimming/selling. It also warns against “tinkering,” over-concentration, and over-leveraging, emphasizing guardrails and patience.

Guests

Stephen Morris (host; long-term investor perspective) and Andrew Sather (“Portfolio Management King”; teaches portfolio mechanics and lessons learned from painful mistakes). No other guests appear in the transcript.

Key claims

Diversify because the future is unpredictable (example: AI disruption; Enron as a fraud risk). A beginner benchmark is 15–20 stocks; too few increases volatility, too many can dilute benefits. Don’t “cut flowers to water weeds” (Peter Lynch): avoid selling winners to fund losers. Use dollar-cost averaging monthly; don’t market-time bear markets. Sell only when fundamentals change; avoid panic and trailing stops if buying distressed names.

Notable examples

Costco vs Google gains; Enron; Netflix becoming oversized; Lamb Research debt mistake; Disney dividend cut; Alphabet debt/data-center reference; Apple patience example.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Portfolio Management

2:56 to 6:00

The hosts discuss the importance and challenges of portfolio management.

“We cut through the noise to focus on what works, compounding, discipline, and the conviction to buy wonderful businesses and stick with them.”

Core Principles of Diversification

6:00 to 7:20

The importance of diversifying investments to mitigate risks is discussed.

“The will take a few more years, I guess.”

Investment Strategies for Different Life Stages

7:20 to 12:32

How investment approaches vary based on life stages and financial goals.

“things so that, uh, I don't make those costly mistakes in the future.”

The Basics of Portfolio Allocation

12:32 to 14:10

Understanding percentage allocation in a diversified portfolio.

“So get somebody on your side who knows what they're doing and please don't try to DIY that is what I would say.”

Understanding Position Sizing in Your Portfolio

14:10 to 18:08

Learn about the importance of position size and recommended portfolio diversification for stock picking.

“Yeah, really, position size is another way to call it.”

The Danger of Over-Manicuring Your Portfolio

18:08 to 19:31

Discover why rebalancing your portfolio can be counterproductive and how to let winners run.

“If you have a stock that's going down, it probably means that business is not doing good or is not going to do good in the future.”

Entry Rules for Stock Investments

19:31 to 21:08

Understand the importance of entry rules and how they can maximize your investment value.

“The next place we need to go, or at least for me, Andrew, that I think we need to go is entry rules.”

The Power of Dollar Cost Averaging

22:00 to 26:03

Learn how dollar cost averaging can build wealth over time and why it's effective.

“Right now, there are just two stocks in the United States with over$5 billion in profit that have grown revenue at 35 % a year over the last five years.”

Navigating Market Cycles with Confidence

26:03 to 28:01

Understand why staying invested during downturns is crucial for long-term success.

“I've always found for me, my sweet spots, like five to 6 % for that.”

Understanding Market Trends and Recessions

28:01 to 29:00

Learn why timing the market and reacting to recessions can be detrimental to your investment strategy.

“And it's basically because the big days, the big days also happened in the bear markets.”
Show all 17 chapters

When to Buy or Sell Stocks

29:01 to 30:54

Discover the challenges and strategies surrounding the decision to buy or sell stocks in your portfolio.

“We don't know when the recession is until it already happened.”

Practical Tips for Portfolio Management

30:55 to 35:58

Explore practical advice on managing your portfolio and knowing when to make changes based on company performance.

“I still struggle with this because you can never get it right.”

Setting Criteria for Selling Stocks

37:07 to 42:01

Learn about criteria to consider when deciding to sell stocks, including debt levels and dividend changes.

“You struggled with Alphabet on that one, didn't you?”

Approach to Stock Purchases

42:01 to 43:36

Learn about strategies for entering stock positions and the importance of comfort in investment.

“And I'm not trying to throw that kind of capital around.”

Patience in Investing

43:37 to 46:23

Discover the value of patience in investing and the risks of rushing decisions.

“That's why I was trying to say the emotions to mess with my decision making.”

Identifying Investment Risks

46:24 to 47:25

Understand common pitfalls that can damage investment portfolios and how to avoid them.

“and their crappy AI, that's all that changes.”

Guardrails for Portfolio Management

47:26 to 50:44

Learn about setting up safeguards to prevent portfolio overexposure and unnecessary trading.

“Over-concentrating in a sector, I think, is probably the next big one.”
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Transcript

Automatic transcript. May contain errors.

0:00All right, so we're wrapping up our Back to the Basics series. We've covered all kinds of great stuff in the previous five episodes. So today we're tying a nice big bow around it and wrapping it all up into the conclusion of portfolio management, which I am so excited to talk about. It's portfolio management is one of my favorite topics. So this is going to be fun. And I say that tongue in cheek because it's absolutely not. So buckle up, get ready, because here we go. This show is sponsored by Liquid IV. Now that the weather is finally heating up, one of my favorite ways to step away from spreadsheets and the SEC filings is getting outside for an early morning run.

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2:55Stephen:You're tuned in to the Investing for Beginners podcast. Investing for Beginners podcast. The show for the long-term investor. We cut through the noise to focus on what works, compounding, discipline, and the conviction to buy wonderful businesses and stick with them. Your path to financial freedom. Start now. Welcome back to the Investing for Beginners podcast, everybody. My name is Stephen Morris, and across from me is the Portfolio Management King, Andrew Sather. This is totally his idea, not mine. I don't want to do this at all, but I have to because Andrew said so. So, Andrew, portfolio management, what is it?

3:43How do we do it? No, I'm kidding. Again, it's tongue in cheek. To me, this is the least fun part of our job. And I don't even have a good reason, Andrew. I don't know why talking about this and focusing on this drains me so much. It just does. I don't enjoy it. I don't know. I don't know, Dr. Andrew. Well, why do you think that is?

4:09Stephen:I feel like the doctor who's on MLB network and he's geeking out over like the little swing mechanics, right? It's like, do this with your shoulder, do that with your thighs and make sure your stance looks like this. Everybody else just wants to see the home runs. We don't care about how the bacon's made. But unfortunately, I have learned some painful lessons around portfolio management. and you start to realize just how important it is. And it's one of those things where the train's moving in such slow motion. You don't learn these lessons for years. And then all of a sudden, it's like you look back and you're like, oh, wow.

4:48Like, for example, I was looking, not on purpose,

4:52Stephen:but I was just looking today. Costco has been a great stock pick for us. And let's put this in context. the real money portfolio is like at 35 grand. So it's not this huge number. Costco, what a great stock pick. It's made the portfolio$250 versus like Google is up, I think two grand or 2 ,500 or something like that. So it's like, obviously a 10 X difference in price and gain based on it being 10 times bigger, but it really shows that like I could have made the best pick in the world and it doesn't matter if you have other picks that are doing better or worse so it's something worth considering and talking about right and i guess like to your point i just haven't been in this game long enough i guess to realize because i know it's important you've definitely pressed into me that portfolio management is one of those things you don't ignore.

5:59I guess I just haven't learned the respect for it. The will take a few more years, I guess. Hopefully I don't have to learn it super painfully. But we'll see what happens. I'll let you know. I think the urinalogy initially really hit the nail on the head. I about said the hammer on the head that would suck.

6:29Stephen:You're about to do that too after this. But I loved your analogy because that is such a good point because, you know, as you were talking, I was thinking more of, I know, I know mechanics are important in all sports. But one of the sports where I think mechanics really shines through is golf. um if you've ever tried to play golf you understand exactly what i'm talking about because what they do on tv is not even close to easy with with that being said like it's so important that i have a coach in these mechanics because literally my entire future rides on my portfolio so i mean i guess i it's a long-winded way of saying that i'm really thankful that i have you to like force these, these lessons on me and make me understand and talk about these things so that, uh, I don't make those costly mistakes in the future.

7:28So thank you, Andrew.

7:30Stephen:You're welcome. I guess I'll continue to be here. So when it comes to portfolio management, uh, from a beginner's standpoint, what is the first thing, you know, if you, so you're teaching your daughter. about portfolio management, what is the first thing you make sure she understands? I think the very first thing is you got to not put all your eggs in one basket. You're carrying that basket of eggs and you drop that basket. Well, maybe that's a bad way to think about it. I don't know. If I'm talking to my daughter, I don't think she like resonate with Enron. But when I talk to other adults, I feel like that resonates pretty good.

8:10Stephen:Enron was one of these companies that was just the best. on all the media and everything. And then it turned out they were a fraud. So obviously, if you had your entire life savings in Enron, you didn't do too well. And so that's why before you talk about all the nitty gritty of like, well, do you want to put 10 % here or 2 % there? Just the most important thing that covers almost everything is spread it out, diversify, make sure everything's not all in one place. Because you just don't know. We don't know the future. Who knew that, let's say, if you went back in time five years ago and told yourself, hey, AI is going to be a thing, be like, what?

8:53Stephen:Right? Like, AI has completely dominated everything. None of us saw that coming. It just kind of happened. And that's just where we are. Same thing happens when industries get disrupted and companies go under. It's those things that just keep surprising us. And we keep being surprised that we're surprised, but that's just part of business as part of investing. So that's why the best thing you can do and the most important thing you do is diversify and make sure not everything's all in one place. Definitely. And I love how you say that. I've never thought of it that way, but that makes so much sense being surprised that you're surprised.

9:36Man, that applies to so much of my life. but anyway uh i think that's such a good point when you say diversify does that mean a bunch of different stocks does that mean some money in the stock market some money in real estate some money in a uh gross uh high yield savings account uh some bonds like what what does it mean when

10:02Stephen:you say diversify it's really different for everybody and even more so than everybody like where you are in your stage of life where you are in your wealth building journey if you are very very early i think a lot of times just having 100 stocks makes a lot of sense but if you start getting into home buying age and wanting to be financially secure you look at high yield savings accounts and having emergency funds. Some people like real estate, some people like gold just for the security and just to have a little bit in there. I've got a very tiny percent in Bitcoin right now. Everybody can kind of take the different aspects of finance and apply it to themselves because we're always talking about stock picking.

10:50Stephen:I like to think of it from a stock picking lens and being some of the earlier in my wealth building journey, I like to just always have this mentality of being 100 % in stocks because my time horizon is longer. And I'd argue most people who are looking into the stock market should try to have that longer mindset. Because one of the things that Brian Feraldi has talked about a lot that I'll repeat again, every different time period of the stock market, we've had the stock market since like the 1800s in the United States. If you look at every five year, 10 year, 15 and 20 year time period at 20 years, if you had been in the stock market, there was no 20 year time period where the stock market lost money.

11:38Stephen:So at the very worst, you are breaking even or making a little bit. So that's even if you bought at the peak of, let's say 2000 or take whatever the peak was before that. The market continues to do well. And so if you have, hopefully if you're in the stock market, you have a long time horizon and hopefully you have a good chunk in the stock market. Now, when you start getting closer to retirement, you start needing to pull funds. That's where you need to start getting creative about, do I throw bonds into the mix? Do I have other kind of investments that play a different role in my portfolio. And in that case, I really recommend going to a financial advisor because they can help you not only understand your risk tolerance, understand where all your assets are, but also understand just from tax perspective, social security, all of those things play a big role, insurance.

12:32Stephen:So get somebody on your side who knows what they're doing and please don't try to DIY that is what I would say. Yeah, it's funny you bring that up because I've noticed this tax season, there's a fiduciary. I can't remember his name or I give him a shout out. He's famous in the local Indianapolis area. I've never met him, but from what I hear, his business is one of the most trusted by local residents. And he's had a commercial running on almost every media platform, the local media platform that there is about that exact fact. Most people think in retirement their tax burden gets smaller. But actually, if you've done things right, and even in a lot of cases, when maybe you're just living off of a small 401k and Social Security, in a lot of cases, your tax burden is going to actually become much more complicated.

13:32Not necessarily more expensive, but more complicated. and that gets a lot of retirees in trouble early on in their retirement because they don't realize that so that is i think a huge point uh maybe you are close to that and that's something you need to start taking stock in as well so let's get into like the the core of what you do when when we use the word portfolio management, I guess the very first core principle in that is allocation. So when we talk about, you know, 10%, 2%, what are we actually talking about?

14:16Stephen:Yeah, really, position size is another way to call it. It's the same thing, or tomato, tomato. though. It's what percent are you putting of your portfolio in a specific stock? I would start by saying the generally recommended principle that everybody kind of talks about, which is based on an academic study that looked at volatility, blah, blah, blah. Everybody kind of says if you're picking stocks for yourself, shoot for a portfolio 15 to 20, because they found based on the different studies that if you start getting like to 25, 30, 35, whatever the number is, the benefits you get from diversifying have a diminishing returns.

15:02Stephen:And so once you get much higher than 20, there's almost like an overly diversification that could be at play. When you start getting under 15, you look at like 10 positions, that can actually be a volatile place to live. If you're confident in your stock picking and you don't mind the volatility, that might work for you. But I think 15 to 20 is always a good benchmark. And I think for beginners, that's a good frame of reference. And that's where I started. I bought one stock a month until I hit 15 to 20 before I even thought about selling something. so if you did it once a month you'd be full portfolio by like a year and a half or two years which is a good amount of time to kind of get your feet wet and start learning something and and actually by the end of that you might actually feel like you know a decent amount and probably making better and better stock picks right so what what what does a full portfolio mean uh like uh if that's a good question i don't know like full i guess fully diversified which saying that out loud seems kind of silly because um it can get completely out of whack like let's say let's say you bought a stock and it was netflix like you bought netflix early early and and Netflix became a huge part of your portfolio.

16:36Stephen:That's like all of a sudden you're like not diversified, but looking in hindsight, it would have been best if you just didn't touch it and just let Netflix continue to become one of the best companies that are in the world. So it's, it's one of those weird things I've noticed. Like I like to experiment with like having different brokerages, having different portfolios. And I've mentioned before how I like, I've like played in crypto and stuff. And I find myself sometimes like I'm manicuring a garden with some of these like play portfolios I have where it's like, well, I don't like how this isn't balanced.

17:14Stephen:So I'm going to balance it. And I think that's actually a dangerous way to think about portfolio, especially if it's like your retirement, your life savings. I think like the human mind kind of wants things organized and neat and tidy. But if what you're doing is rebalancing and taking away from your winners to make your losers bigger and then everything kind of balances out and you're just constantly like making your portfolio feel full and organized and happy, what you're really doing is you're cutting the flowers to water the weeds. That's a quote by Peter Lynch. You don't want to be selling your best companies, your best stocks to be buying your worst stocks because yes, we're trying to outsmart the market.

18:01Stephen:And yes, we're looking for our special insights, but the market's going to be right more than it's wrong. So if you have a stock that's going up, it probably means the business is doing good. If you have a stock that's going down, it probably means that business is not doing good or is not going to do good in the future. So we have to be careful about over manicuring our portfolios and just kind of letting them run as they will.

18:31Stephen:Because then that will allow the winners to run. And that's... We don't have to get super into it, but there are moonshots in the stock market, which is why the stock market goes up as high as it does. because those moonshots raise the average up so high. So if you ever get one of those in your portfolio, you want to keep it because that will drive most of your returns. Right. That's such a good, I guess, mindset check. As you're looking at your investments, understanding truly what is driving your portfolio because I love that quote, you're cutting the flowers to water the weeds. So huge. And that will destroy you, destroy your portfolio, completely blow it up.

19:27And we'll get more into that later. The next place we need to go, or at least for me, Andrew, that I think we need to go is entry rules. And those vary drastically, especially as I talk to the value spotlight community, talk to you, Evan. Everybody has different entry rules, like how they, and when we say entry rules, that means how you're getting into the stock. And for what we do, it's very important that the math lines up to when we enter the stock to ensure we're getting the best, trying to get the best value for our dollar. So what are your entry rules when it comes to that stuff, Andrew.

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20:53Stephen:Build a portfolio that fits your needs and go after your money goals with Plink. Head to the link in the show description to download the Plink app today. Investing involves risk, including risk of loss. Diversification does not guarantee profit or protect against loss. ETFs are subject to market fluctuation and additional expenses. Opinions expressed on this podcast are not necessarily those of Digital Brokerage Services LLC member FINRA SIPC. If you'd like a way to have more luxury without paying luxury prices, here's an idea. I just recently took a chance on a weatherproof utility tote from Quince and it delivered on all of its promises.

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22:40Stephen:Starting with the basics, starting with the easy, but starting with the most important. I'm constantly putting money in. It's called dollar cost averaging. You got to be putting money into the market no matter what the situation and do it consistently. I like to do it once a month. That consistent habit will build a wealth snowball that will slowly get bigger over time, but that needs to be front and center. Like we can't be trying to market time coming in and out. That's, it's just not going to work. Dollar cost averaging works. That's why 401ks people blink. And all of a sudden they have six figures in a 401k and didn't even realize it.

23:19Stephen:The reason why it works is because of dollar cost averaging. So let's start with that. And then as far as knowing how much to put into a stock, I have a stock that I'm really interested in. How do I know how much of my portfolio they put into it? I think over time you start to get a sense of what kind of investor you are and what you're comfortable with. And I know that sounds kind of just vague and not really helpful, but use the example of if you're ultra growth, like almost investing in every IPO or you're almost like investing in startups or something, you have to understand that when you play by those rules, your probabilities of success are pretty low.

24:12Stephen:When you go into these places that are super high growth, super high competition, there's only going to be usually a few players that come out on top. So statistically, if there's only a few players that come up on top, there's a lot of losers. So if you're buying super high growth, you need to buy a lot of positions. So maybe even the 15 to 20 framework doesn't work. You should have maybe 50 to 100 instead of 15 to 20. You really want to have a lot of stocks because you just need like the Netflix or the NVIDIA or the Tesla to really carry your portfolio. That's if you're playing that game. Uh, on the flip side, if you're trying to be like Warren Buffett, who, um, you know, doesn't want to do anything for five years and then all of a sudden take out his elephant gun and go hunting.

25:06Stephen:Maybe, um, I think you do need to pair that patience with the higher position size, like Warren Buffett. He really waited until he had the fattest of fat pitches. Like he was so certain about Coca-Cola. He knew so much about it. He had probably been watching it for years and years and years. And, and because he has so much conviction about it, he made it a quarter of his portfolio. That's a pretty big allocation. You don't have time. Uh, I think he spread it out over like six months. So he did like a big chunk of the big chunk, but yeah, essentially it was essentially at one time. That's, um, that takes a lot of chutzpah to quote myself.

25:48Stephen:You don't get, you don't have many chances when you're putting a quarter of your portfolio. So you better make sure those, those chances do well. And so I think that's why it matters who you are, what you're trying to accomplish. I've always found for me, my sweet spots, like five to 6 % for that. So I consider like my high conviction position. And then if it's something that's, maybe like a higher chance of failure. I'll scale it down. It'll be like a percent and a half or something. So those are just like the percentages I've fallen on. But basically, I found that like, just because I had more conviction about a stock didn't make me any more right than usual.

26:39Stephen:And usually actually meant I was more wrong because it was more value and it was more distressed and those are usually more wrong. So I've had to like pare down my, my exposure to different stocks because I like to play the numbers game. I like to buy a lot of beaten up stocks and find the ones that really rebound. And so that's, what's worked for me being in that five to 6%, but everybody might be a little bit different. That's why it really does depend on what kind of stocks you're trying to buy and how those stocks tend to perform as a group, not just as one or two. When it comes to dollar cost averaging, Andrew, you had mentioned like, The studies show that just being in the market beats trying to time it every single time.

27:25And I just want to make it clear. Correct me if I'm wrong. That's like every single downturn bear market. Like, ultimately, if you keep dollar cost averaging, even through those tough times, you are still going to come out on top. So Andrew continues the dollar cost average. which Stephen sees what's happening, pulls all his money out of the market and waits for it to turn bullish again. And then gets back in the market. Andrew's going to crush Stephen in the longterm. Correct?

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28:01Stephen:Yeah. And it's basically because the big days, the big days also happened in the bear markets. So even if Stephen misses the bear markets, there's enough big days in the bear markets where the dollar cost average person would come out on top because like they're they're your strategy would wait until things turn until there's like a consistent sustainable uptrend but by the time that happens a lot of the gains are gone right so that's why you just have to stick through all of it yeah i just wanted to make sure that that point got driven home because i feel uh you know talking to family and friends um that's kind of the rule they think they need to play by is up the market's getting bad so we need to hop out of it and that is not the case that is actually going to hurt you in the long run and i just wanted to make sure we drove that point home uh so the next oh go ahead sorry real quick evan made a good point when we were doing AAR the other day and he said that when people say there's a recession they're saying it six months after it happens like that's the literal definition of it you have to wait six months so even when the economists call something a recession they're doing it late so it's always too late to act on where we know so it's like oh yeah I would have I would totally sold because I knew a recession was coming.

29:41Stephen:We don't know when the recession is until it already happened. I think that's the exact quote he used. And it's because of the way that we define recession and just the way it is. It's just not obvious when you're going through it. It's just not. Well, yeah, because you need the data to back up the claim. And you can't have sufficient data in a month. you know people people call um covid a recession and i i disagree because the market like yeah it took its hits but in some sectors but the market grew a lot during covid that that wasn't a recession at all it may have felt like one then you know it's you got to have the data to actually back it up.

30:28And to your point, it takes a significant amount of time to get that data. And by the time we have that data, we've already been suffering through the recession as it is. So we might as well just strap up our boots and stay. You've already ran half the marathon. You might as well finish. So, I mean, that's such a good point. Thank you for bringing that up. And the next question that is probably the hardest for me is knowing when I need to add or trim in my portfolio.

31:06Stephen:Yeah, I still struggle with this. I still struggle with this because you can never get it right. Like you get it right one time and then the next time you totally screw it up. and I've done it so much where it's like you stick with a stock, you stick with it, you stick with it. It goes nowhere. All right, I'm finally out. And then two months later, it rockets up 20%, 25%, whatever it is. I guess the only thing I've been able to find peace with is like,

31:43Stephen:which confirms like what we've been saying a lot on this show over many years, but it's like, if something fundamentally with the business has changed, then sell. And as much as I try to like go away from that and sometimes kind of be a little too cute and figure out, Oh, maybe I can, you know, jump in and out or whatever. I realized that it's a losing game. And at least you, you won't be able to ever avoid this fact that you will sell something and it will continue to go up. Like you just be in the market long enough, it's going to happen. Um, but at least if you can hang your hat on, like I made a decision based on the fact that I thought I didn't like the direction the business is going, then you've kind of already won at that point.

32:31Stephen:Like, like that's all we can do is just be invested in the businesses that we feel the best about based on our research, based on our knowledge. and based on whatever wisdom we can glean. And then just don't be in the businesses that you don't feel that way about anymore. It's not a guarantee to success, but that's the best thing you can do. Yeah, definitely. I struggle with it too. And you know me, like the panic button is real in my office. Do you ever struggle with that? like not wanting to be wrong i guess or whatever that mentality is to where you just don't want to sell it even though it's costing you money yeah like adobe

33:26Stephen:oh man i'm i'm i'm telling myself that like i'm giving them a chance to to see what the new ceo was going to do, right? Maybe a lot of that's just not wanting to cut my losses. But yeah, I think

33:45Stephen:for a long time, I've had this rule of like, just selling negative earnings. That's probably something I should consider going back to because it's so simple. It's so easy.

33:59Stephen:I'm sure you've seen the buzz online, but let me give you a little bit more information. Live shopping on Whatnot is absolutely popping off at this moment. I've seen the shows firsthand. I've seen Whatnot climb to the top of the app store. And I've looked at the money that people can earn as selling on this platform. And we're talking small, you know, mob and pop businesses, medium-sized businesses, and even multi-million dollar businesses. All of them are seeing massive real growth on this platform. If you're somebody who is selling or has sold in the past and you've sold online or in a storefront, maybe you're used to a full-time job or maybe it was just a side hustle for you, you already know the challenge.

34:32Stephen:You're just hoping that somebody is going to stumble across your listing and you're waiting for that to be the right person to just stumble upon whatever it is you're selling. Whatnot flips that. On Whatnot, you can go live and sell directly to your buyers in real time. They see what you've got. They get to ask the seller the real questions and then they buy. And they keep coming back because you've now built that genuine relationship with them. Whatnot is the largest dedicated online live shopping platform. and they sell anything from beauty to collectibles to art to clothing to electronics, even something like cookies.

35:03Stephen:And sellers are building real thriving businesses off of selling these things on Whatnot's platform. Whatnot buyers actually spend more than an hour a day on the app, and they're not just browsing. They're doing things like buying and coming back because they're able to live talk to the sellers and ask them the questions that they want to know, get answers, and then purchase that product instead of waiting off never getting the answers for things that they need. People selling on WhatNot are able to sell 10 times more than on any other major marketplace. And this is because they're not just listing a product blindly and hoping that the person is going to trust them and believe in them.

35:34Stephen:They're building real genuine connections with the buyers and they're able to build a lasting relationship that makes that buyer want to come back again and again. And for a limited time, WhatNot will match your first$150 sold in the first month. Visit WhatNot.com slash sell to start selling. That's W-H-A-T-N-O-T dot com slash sell. Whatnot.com slash sell. As business owners, I think we all understand that we're spending too much time managing the small stuff with our business's finances. Because there's multiple bank accounts, multiple apps, a place to do your bookkeeping, a place to do invoices, transfers to keep track of debt payments.

36:12Stephen:It goes on and on and on. But imagine you could have all of your biggest hassles with accounting and finances in one place. And that's what Found offers. It's a business checking account with built-in bookkeeping and tax software designed for small business owners like you and I. Found empowers us to keep things organized and unlock time to strengthen our company's competitive advantages, which as we all know on this show is the best way to build a thriving business. One of the things that is really critical in this day and age with the power of the internet to work with so many different types of people in so many different places is the ability to make contractor payments easy and trackable without all the ridiculous fees.

36:47Stephen:Found has that too. Take back control of your business today. Open a Found account for free at found.com. That's F-O-U-N-D dot com. Found is a financial technology company, not a bank. Banking services are provided by Lead Bank, member FDIC. Join the hundreds of thousands who've already streamlined their finances with Found. Is that like they report negative earnings over a certain amount of time? Like over a year. Okay. one that I have kept and I've never regretted it every time I've done it but if a company cuts their dividend sell it I did that with Disney and that was a great decision

37:34Stephen:and then if a company gets too much debt like they ramp up a ton of debt especially if that debt's not used for anything worthwhile Wow. I made the mistake of... You struggled with Alphabet on that one, didn't you? When they started to do... No. The data centers. No. You might be thinking about that at somebody else. Oh, okay. But there was a company called Lamb Research, which does semiconductor equipment. And I sold them back in like 2019 because their debt tech went from like 0.2 to like 1. And I was like, wow, that's too, that's too much. You know, you guys are getting so aggressive and that was stupid because still a debt equity of one is still pretty conservative.

38:25Stephen:And they ended up using the money very well. And that stock quadrupled and I didn't get any of that. So that was great. It's, it's, there's, there's something about like watching your best stock picks that perform so great after you've sold. So yeah, that's fun. but no I think looking at companies that have taken on a lot of debt turned money on set money on fire those are types of things even if the stock does go up I'm still okay and happy that I made that decision because that's as much as you can control I think it's common sense you don't want to be in companies that do that routinely So I like the idea of like selling on way too much debt and debt levels that are unsustainable.

39:22Do you ever have a price point that a stock needs to reach for you to sell?

39:32Whether it's down or up like a stop loss.

39:36Stephen:I've experimented with those like trailing stops. I did that early, early on in the newsletter. And the problem with that was like I was buying beaten up stocks, stocks that are out of favor that oftentimes would continue to fall even after I bought them. But those are the type of stocks that also rebound really, really nicely. So what I was doing was just like selling at the worst time right before I would capitulate and come back up. So I found for me, the type of investing I do, the trailing stop doesn't make a lot of sense. But I could imagine for somebody who, I don't know, maybe they're in like really growthy stuff or they're buying with the trend.

40:20Stephen:I could see a trailing stop being helpful there. I'm just so fixated on valuation that I tend to buy stuff that's more distressed. So a trailing stop really doesn't make a lot of sense for me. And then I don't like the idea of like selling out of something that's up a lot unless I choose and unless I make that choice, especially because of what happened with lamb research where that's like burn. We all have our lamb, bro. Don't worry about it. Yeah. But it's I think it's a great lesson because then every time I'm like tempted to take profits, just think about lamb research and be really careful about cutting the flower.

40:59When do you cut your flowers?

41:04when i get there i'll let you know gotcha fair point so no i think that those are some some great core uh beliefs to to have around managing your portfolio uh i did i did one to throughout my the way i enter a stock is i have to be have enough conviction um that and this is kind of a weird uh rule i guess i don't know i've never even i don't even think i've ever talked to andrew about it i have to be willing to either spend a x amount of money because the stock might be on the cheaper end you know 60 70 bucks um or i have to be willing to buy a whole share. So like with Costco, it's fairly expensive.

41:58And that rule doesn't always apply because, you know, Markel, it's like two grand a share. And I'm not trying to throw that kind of capital around. Not that rich yet, unfortunately, that I can just go buy, you know, 15, 20 shares of Markel. But, um, so I mean that it obviously has to be a flexible rule, but if I can't make myself comfortable enough with spending a chunk of money, um, then I won't buy it because, uh, my thesis, the way I view it is my thesis isn't strong enough. And so, yeah, that's kind of how I approach that entry level. And so I will buy a portion or a share, sorry, and sit on it.

42:53And then from there, I'll decide, OK, I like it. I'm comfortable with it and I can continue to move. Or it's like, yeah, I'm maybe I got this wrong, starting to second guess myself a little bit. So we'll just hang on to that share and we'll see what happens from there. That's my approach. I wanted to drop it in earlier, but I didn't get a chance. Yeah, I can kind of.

43:21Stephen:You just let me go. Sometimes you just wind me up and let me go and I'm just not stopped. But what got you in the idea of sitting and waiting before choosing to deploy a new capital? So I think there's a lot of wisdom in that. That actually comes from day trading. um just some lessons i learned uh day trading and

43:48i think you know it's like we talked about uh when we were talking about not not biting on the narrative and things you know uh one of my rules is i never buy a stock after i finish researching it i gotta wait a few days to let it simmer it's kind of the same thing i don't want the psychology or the mentality to mess with me, mess with the emotions. That's why I was trying to say the emotions to mess with my decision making. So I let it sit there for at least a month in my portfolio because I don't tinker with it a lot. So after that time, if I'm still excited and I still think it's great, then I, you know, okay, I've made a good, I feel comfortable thinking I made a good decision.

44:43But yeah, I don't know if I answered your question. I don't remember what it was now.

44:48Stephen:Yeah. A month sounds like a long time within the grand scheme of things. It's in an investment career, it's not going to make or break you to have to wait one more month. Right. Definitely. Well, and, you know, that's one of the things I learned very early with some prescribed reading from you guys. I think it was Warren Buffett. Or maybe it was Peter Lynch. I don't remember. But that's one of the things that they were really heavy on is don't feel time constraint. because this isn't a make money today type thing. Be patient. And when you look at how Warren Buffett went through his career, like all you see is patience.

45:44Probably the most patient man in the world, in the history of the world, is Warren Buffett. And I think that's a lie I bought into early on. Not like a lie that someone told me, I guess a lie that I was telling myself that like, I bought this stock. It's got to make money right now, right now. It's got to make money. Let's go. And that's not the case at all. And there are some stocks, you know, that you might buy. The, you know, Apple is probably a good example. Is Apple revolutionizing anything right now? No. Like the camera on their stupid phone, that's literally, and their crappy AI, that's all that changes.

46:27Is there apps that no one uses that you can't delete the stock? But do I think that's going to be Apple forever? No, absolutely not. I'm just waiting on the next shoot of all and they come out with whatever groundbreaking technology that they invent next. And they're going, I have full faith that Apple will do that because that's just Apple. That's what they do. Could I be wrong? Absolutely. but i think that you know that the apples are one of those stocks like owning it right now yes it's not getting you a lot but eventually when they hit that next huge discovery like that's then you're going to see that really really pay off and you just got to be patient and wait yeah i like that so um i want to transition a little bit to to some negative and because i i hate i'm i'm like the eternal optimist kind of guy like i love negative people i i just i i have to limit my market exposure to negative people because i get frustrated super fast um so i really hate to bring this stuff up but it does need to be talked about and that is the key ways that we see people blowing up their portfolio just like crazy and for me the number one way and we've talked about it multiple times we've even uh stolen a a catchphrase from a popular tv show called the league and that's uh tinkering um tinkering with your portfolio is absolutely going to and 90 percent of the i don't know what the number would be but a very high percentage of the cases is going to hurt you more than it's going to help you.

48:25Over-concentrating in a sector, I think, is probably the next big one. You're so comfortable in investing in, you know, biotech because you're a pharmacist or whatever, and you understand that really well. So you just focus all your portfolio into that sector. um super dangerous and a really easy way to to hurt yourself and then over leveraging i i would say is the last uh dangerous way i wouldn't say it's common but but it's definitely a dangerous thing to do uh that andrew's already talked about um that you need to make sure you're watching out for but did i miss anything in those andrew no those are huge um appreciate you bringing it up

49:19Stephen:because yeah it's not all cupcakes and rainbows all the time yeah well i mean you know you you know it's like a collaring book right you have to know where the lines are for you to call it and definitely setting up safe guardrails for yourself to make sure you're not over concentrating creating your portfolio in a specific sector. Definitely like I, and Andrew can, I don't know if he remembers like having to teach me this or not, but not opening my brokerage every single day. That was a big lesson because I love, you know, we've talked about, I love to sell, I love to buy, I love to tinker. It's just a dopamine hit for me to just play.

50:07and so and and one of the guardrails i've built for myself is i allow myself x amount of money every month that i get to just put in my brokerage account that i have set aside just to play with that and sometimes i make money sometimes i lose it all um i guess it's more of a gambling like just swing trading playground that i that i keep for myself just to keep myself entertained um But again, that's a guardrail I built to keep myself from tinkering with my actual portfolio that I need to stay strong. So, yeah, it may not be fun and optimistic to talk about these guardrails, but they are definitely some of the most important things you can do for yourself.

50:54Stephen:Absolutely. But yeah, wrap this up in a nice big pretty Christmas present for us, Andrew. Too much pressure. Too much pressure. I would say just make sure you're spread out enough where you can sleep at night and not have to worry about your portfolio. Not have to freak out if you see news headlines that say the Fed did this or that. So have some sort of diversification and make sure your dollar costs averaging. Put money away, make it a habit, make it automated. And don't sweat the small stuff. Don't tinker. and stick with it for the long term. Yeah, definitely. And you and Evan actually talked about that a while back about, yeah, I love it, Andrew.

51:43And the only thing I would add to that is just make sure you have your guardrails in place so that you don't blow yourself up overnight. Love it. Let us know what you guys do to manage your portfolios and any guardrails you have, what your entry strategies are, how you portion size. Let us know your thoughts in the comments. We would love to hear from you. So it's going to wrap it up for today. We will see you next time. In the meantime, though, never, ever, ever forget, invest with a margin of safety, emphasis on the safety. Peace.

52:22Stephen:You've been listening to the Investing for Beginners podcast. All show notes can be found on our website at einvestingforbeginners.com. To master the basics of stocks in seven days, sign up for our free email series at einvestingforbeginners.com slash newsletter. Until next time, have a wonderful day. The information contained is for general information and educational purposes only. It is not intended as a substitute for legal, commercial, and or financial advice from a licensed professional. The hosts may own positions in the securities discussed. Review our full disclaimer at einvestingforbeginners.com.

53:24Stephen:from the latest Apple event to why nobody can afford a house right now. And some people are saying it's the best part of their morning. Because we know something you don't. Business news doesn't have to be boring. So check out Morning Brew Daily wherever you get your podcasts. And on YouTube.

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From the publisher

We’re wrapping up the Back to the Basics series by tackling the part of investing that’s not flashy—but can make or break your long-term results: portfolio management. Stephen and Andrew break down what it actually means to manage a portfolio, starting with the simplest (and most important) principle: diversification—because the future will surprise you, and you don’t want one stock or one sector to decide your financial fate.

From there, the conversation gets practical: how many stocks is “enough,” what position sizing looks like for different investing styles, why over-rebalancing can hurt returns (“cutting the flowers to water the weeds”), and why dollar-cost averaging beats trying to time the market. They also cover real guardrails—like reducing tinkering, avoiding over-concentration, and knowing what would make you trim or sell a position.

What You Will Learn

Why diversification is the first rule of portfolio management

How position sizing works—and why 15–20 stocks is a common “sweet spot” for stock pickers

Why over-rebalancing can sabotage your winners 

How dollar-cost averaging helps you avoid the trap of market timing

Common ways investors blow up portfolios—and the guardrails that prevent it

Timestamps

00:00 Wrapping up Back to the Basics & why portfolio management matters (even if it’s “not fun”)

01:49 The #1 beginner rule

08:16 What “diversify” can mean

12:44 Position sizing & why many stock pickers aim for ~15–20 holdings

15:17 Rebalancing danger: “cutting the flowers to water the weeds” 

19:23 Dollar-cost averaging, consistency, and avoiding market timing

26:05 Why timing fails: big up days happen during bear markets too

29:51 Adding vs. trimming: focus on fundamentals changing, not emotions

34:55 Sell rules: negative earnings, dividend cuts, and unsustainable debt

45:58 Guardrails + how portfolios get blown up: tinkering, over-concentration, over-leverage

Resources Mentioned

The Value Spotlight Newsletter: ⁠https://einvestingforbeginners.com/value-spotlight-newsletter⁠/

Have questions or want your story featured? Email the show at ⁠newsletter@einvestingforbeginners.com⁠ or comment below. Your feedback shapes the podcast!

Remember, invest with a margin of safety—emphasis on the safety. Have a great week, and we’ll talk to you next time.

Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.

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