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7 AI Tools That Build a One-Person Business in a Weekend — No Staff. No Code. No Stress.


Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

  • Discover seven AI tools that help you build practical business systems without hiring a team or learning to code.
  • See how customer research, app building and routine email tasks can connect into a workflow you can adapt.
  • Learn why you don’t need all seven tools — and how choosing one useful job makes getting started more manageable.

You’ve had the business idea for months. What keeps pushing it into “someday” is everything you think you need before you can start: a developer, an assistant, a working website and time to figure it all out.

Then another weekend disappears into research.

In the video above, I walk through seven AI tools that can help you build the practical pieces of a one-person business — from a working app and customer research to email workflows and connected automation.

But here’s the part that can save you the most time: you don’t need all seven, and you don’t need to build everything this weekend. You need one useful thing that works.

In my book, The Wolf Is at The Door, I recount a conversation about the shrinking shelf life of information. Something you’ve just learned can quickly become outdated. For an aspiring business owner, waiting until you understand every new tool creates a moving finish line. Pick a problem you understand, then learn what you need to build a solution you can test.

More people are finding that starting point.

A FreshBooks report, updated September 15, 2026, surveyed 500 solopreneurs and micro-business owners. 60% said AI helped them launch something they couldn’t have built alone.

That’s the possibility worth exploring this weekend. A simple app you’ve been putting off. A system for researching potential customers. A way to handle routine questions without every response starting from a blank page.

To make the connections concrete, the video follows a customer-recovery example: identifying inactive customers, researching their needs, tracking the follow-up and understanding their responses. It shows how separate tools can contribute to one business process, with exceptions brought back to you.

You’re still responsible for deciding what to offer and checking that the work is useful. These tools give you more ways to turn that decision into something tangible.

The seven tools, the customer-recovery workflow, and the ChatGPT technique I use are covered in the video above. You’ll see how research, browser automation, email, visual mapping, and app building fit together.

Choose one useful thing to build this weekend. Give yourself something to test on Monday, instead of another idea to revisit someday. Then ask what you could build if that job stopped consuming the time you needed to build it.

The free AI Success Kit, available to download for a limited time, comes with a free chapter from my new book, The Wolf is at The Door – How to Survive and Thrive in an AI-Driven World.

Key Takeaways

  • Discover seven AI tools that help you build practical business systems without hiring a team or learning to code.
  • See how customer research, app building and routine email tasks can connect into a workflow you can adapt.
  • Learn why you don’t need all seven tools — and how choosing one useful job makes getting started more manageable.

You’ve had the business idea for months. What keeps pushing it into “someday” is everything you think you need before you can start: a developer, an assistant, a working website and time to figure it all out.

Then another weekend disappears into research.

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8+ Ways to Find Your First or Next Rental Property in 2027


Finding real estate deals is a challenge for many rookies. Trying to tell the difference between a great deal and a property that is merely disguised as one is something usually only experienced investors see through.  But in this episode, we’re sharing some of the best strategies we use to find real estate deals—including a few options you’ve probably never heard of!

Welcome back to the Real Estate Rookie podcast! Today, we’re breaking down eight different ways to find your first (or next) rental property! First, you’ll need to build your buy box so that you know exactly which types of properties to look for and where to find them. But then, we’ll show you how to work through the MLS the smart way, find real estate deals via word-of-mouth, and use seller concessions, wholesalers, and pocket listings to buy undervalued properties. We’ll even share an often-overlooked opportunity that could help you buy an entire real estate portfolio in one transaction!

For each strategy, we’ll get into the real advantages and drawbacks, so you know exactly which of these channels fits where you are right now. Finally, we’ll show you exactly what to track so your hard work actually translates into your next deal!

Ashley:
You want to buy a rental property, but where do you actually find one? Do you open Zillow and scroll until something looks cheap? Do you send letters, cold call owners, build relationships with agents, or wait for someone in your network to mention a property?

Tony:
It can feel like successful investors have access to a secret website full of discounted homes, and the truth is they don’t. Most deals come from ordinary channels used with a better buy box, faster analysis, consistent follow-up, and enough offers to let the numbers, not the listing label, decide what is actually a deal.

Ashley:
Today we’re breaking down the ways we’ve used to find investment properties from Zillow and word of mouth to pocket listings, wholesalers, direct to owner outreach, and retiring landlords. For every channel, we’ll cover the advantages, the dropacks, and the strategy it fits best. So looking ahead to 2027, shifting inventory and seller motivation could create new pockets of negotiating leverage, which is why rookies should start building these deal finding systems now. Welcome to the Real Estate Rookie Podcast. I’m Ashley Kerr.

Tony:
And I’m Tony J. Robinson. With that, let’s get into our first step for finding the right rental properties now and what’s working today. So the first step is to start with your buy box. Okay, start with a very, very clear buy box. And a buy box by definition is just the boxes that a property needs to check in order for it to achieve your specific goal. So that it can vary from strategy to strategy and your buy box for a flip is going to look different than your buy box for a wholesale deal, is going to look different than your buy box for a long-term rental is going to look different than a midterm rental different than a short-term rental. So every strategy, even in the same market can have a very different buy box. But there’s a few ways that I would approach this.
At a high level, before you even think about buy box, the first thing you have to focus on is what is my investment goal? Am I doing this for consistent monthly cash flow? Am I doing this because I want a nice vacation house on the lake? Am I doing this because I want a big chunk of cash? What is your specific investment goal? What is your purchasing power? How much cash do you have on hand? How much loan can you get approved for? And then what’s your strategy? So if you have those three things, your goal, your purchasing power, your strategy, that’s the foundation for building out your buy box because maybe I’ll give you guys an example. Let’s say that you want to buy, say you live in Southern California, any high cost of living area and your goal is I want a cash flow, 30% cash on cash return buying something here in California.
With a lot of strategies, buy and hold strategies, that’s going to be tough. So you got to make sure that you have that laid out first before you actually put together your buy box. But once you have those things in place, and this is a mistake that I see a lot of rookie investors make, is that they start by going into Zillow or Redfin and seeing what’s for sale and they just kind of scroll and so they find something that looks nice and then they back into, okay, do I think this is actually a good deal or not? But the whole purpose of the buy box is that before you even hunt for anything that’s for sale, you’re doing very deep and thorough research on the market to understand what is already proven to do well in this market. So if I want to flip a house before I go hunting for properties to purchase, I’m going to look at all the homes that have sold in the last 30, 60, 90 days that are around the price point that I think I’ll be able to afford.
And I’m going to understand all those characteristics. If I want to buy a short term rental, I’m going to look at all of the top performers in this market to understand what are the specific boxes they’re checking that I need to make sure I’m including in mine as well. So we start the process of your buy box by doing a very deep and thorough research on the current market conditions and understanding, hey, what are people already paying for in this market? You do those two things. At least that’s how I start my process for buy box building.

Ashley:
We also have a buy box checklist that you guys can download. Go to biggerpockets.com/resources. And if you go under, it’s like finding deals or something like that, that section, there’s an actual buy box worksheet. And I created it and it goes through all of the things that you should think about when building your buy box. Some of these won’t apply to you. For example, there are certain things that may be in my area of the market that may not be in whatever market you’re in, or you may need to add some things to the sheet because it’s in your market and maybe not in my market, but at least it’s a starting point for you where you can go and see, okay, these are some of the things I need to look at. And then some of them I give more detail as to why this is something that should be on your buy box.
So you can go ahead and download that. It’s free to download. I’ll try to also get it linked into the show notes for you guys into the description on YouTube also so you can download that.

Tony:
So once your buy box is complete and you understand what you actually need to go find in that market, the final piece of this buy box step is actually working on getting the offers submitted. And oftentimes, especially when I’m working with students, I’ll tell them, once you have your buy box, we just need to go search for deals that fit the buy box and worry a little less about what the actual purchase price is right now because purchase price is always negotiable, but can we find the deal that meets the buy box? And then once we find the property, there’s different ways that we can negotiate to try and get the overall value of the deal to align with what we need. One of the most kind of simple solutions is we just try and reduce the price. If they’re asking 350, but it works for us at 300, well then let’s just offer 300.
So just asking for price reductions. Another great strategy that works especially well in today’s market is getting seller credits or seller concessions. Can you get the seller to give you a credit at closing to help buy down your rate? We’re actually in the process. We should be closing hopefully in a few days here on a new primary and we did both of those things. We got a 30K reduction on the purchase price and we also got another 30K in seller credits to help buy down our rate. So those are two things where the property fit our buy box. We knew exactly what it was that we were looking for for our primary. We found the property was priced higher than what we wanted it and we got both of those concessions built into the deal. So the buy box is the starting point, find deals that match and then use your negotiation tactics to make the numbers actually work.

Ashley:
One of the things I really like to do is try and find different ways to fund the deal. You can offer cash, you can get conventional financing, you can get seller financing. There’s all these ways to get creative and you can get a deal or a discount by the type of financing you are getting on the property. So if you’re able to get a better interest rate than somebody else because the seller is going to finance it for you at 5% instead of the bank that’s going to charge you 7.75% for a loan, you’re maybe able to have this as a better deal because you’re not going to be paying as much interest as someone else would. So getting creative with the finance can help you to get that discount while keeping the price the same. Or sometimes I even offer more if they’re willing to do seller financing.
Then the next is just looking at where the missed opportunity is in the property. Where can you add a value in just the operation? So I’m not saying going in and doing a full gut rehab to increase the market rent to make more money. I’m talking about things that you can do operationally, like quoting out the insurance on the property, maybe even disputing the property taxes to get them lowered. What are things that you can do right now that don’t mean that you’re going to have to put a ton of money into the property and it’s just operational pieces that you can buy it at this price point because you know you’ll be able to increase the cash flow because you’ll be able to put better operations into this property, even increasing market rent. And then the last thing is the seller’s motivation. You can use that to get a discount as in do they want to fast close on this?
Can you increase the timeline and put that into your offer? And maybe they’ll be more likely to accept a lower price knowing that you’ll be able to close fast. So think about that. What is their motivation? What do they want out of this? And try to include that. A lot of times when I’m buying properties, they’re full of stuff and I’m buying them from the estate or I’m buying them from someone who’s moving or I’m buying them from someone in their family. So I always put in my offer, you can leave whatever you want and I will take care of it. And that is usually a motivation for them to accept my offer because they don’t want to have to deal with cleaning out all of their family members’ stuff, getting dumpsters, going through everything. This way they can just leave whatever and I’ll have somebody take it out.
So there’s other ways to get discounts instead of just getting a cheap property, a better deal.

Tony:
Step number two or strategy number two is one of the easiest. And it’s just starting with the MLS, Zillow, Redfin, the places that you’re probably doom scrolling already. But this is best for Rickies that are looking for just kind of a quick and efficient way to get a large volume of opportunities to look at. Now obviously there’s pros and cons to finding deals on the MLS, on Redfin, Zillow, whatever it may be. I think the benefit, again, is that you can literally see inventory in any city across the country with a few clicks. There’s no gatekeeping, there’s no hoops you have to jump through. It’s just information that is readily available. Tons of public history, tons of, you can see the property taxes, you can see the transaction details. When did it last sell? How much did it last sell for? So there’s the photos, you can look at comparable properties.
There’s just an abundance of information that is completely free.

Ashley:
So the disadvantages are obviously it’s to the open market. So you’re going to have more competition on the property. Also, people may not exactly list their property for what it’s actually worth because they’re looking at what other people are listing, what other houses have sold for. So this has been a deterrent for rookie investors. Sometimes when you see the list price, you say, oh, well that doesn’t make sense. That property’s not worth it, blah, blah, blah. But remember, you have to have the mindset that the list price isn’t the purchase price. Also, there’s the Zillow’s estimate, which I find incredibly inaccurate or inconsistent. Maybe on some of my properties it’s accurate and then other ones just way off. At one point in time I bought a property for $52,000. It said on there that I purchased the property for $520,000 and the Zestimate on it was like $600,000.
This was a little duplex I bought for $52,000. So don’t rely on all the information, even the property taxes. So that’s also a disadvantage is you’re not getting fully accurate information from browsing these websites. The next thing is the rent estimates too. I would do your own research. A lot of the rent estimator calculators that are integrated into these different websites, a lot of them are only pulling data from their own website. So like Zillow, they’re getting their information from people who listed their property on Zillow. There’s a lot of mom and pop landlords that don’t even use some of these platforms to list their property. There’s people who still list property in the newspaper. I actually, I use TurboTenant and one of the places that they push out all of my listings, there’s like, I don’t know, 17 places my listing goes. And one of those is Craigslist.
And believe it or not, I get a huge amount of leads from Craigslist too. So there’s still listings out there on Craigslist even.
So just know that not all of the information is extremely accurate on some of these websites that you should do your own research to call around to property management companies, see what they’re charging for rent for different places. You can just say you’re looking for a two bedroom apartment or something that’s comparable to what you’re looking to buy and see what they have available for rent. And then kind of the last thing is obviously these are being put on these websites to sell. So they are going to show the best features of the property and these properties are going to look sometimes better than they actually are. Once in a while, you get the properties that have the worst photos, have the worst description, and you end up finding that it’s listed as a three bedroom, but it’s actually a five bedroom, but nobody knows that because it’s listed wrong.
So you do have those gemstones in a while, but sometimes they’re listed to be able to sell. So it’s just highlighting the great parts. My brother is looking to purchase house hunting and my mom went with him the other day and sent me the listing. Beautiful house, beautiful, beautiful yard. It had everything that my brother was looking for. They went to tour the property and in the basement there was this one slider door. They opened the slider door and it is literally just a room full of black mold. Obviously there was no picture of this on the MLS. So just that is another con is that it just doesn’t give all of the information. And then there also can be inaccuracies.

Tony:
Let’s talk a little bit, Ash, about how to actually use the MLS like an investor, because I think that’s maybe the most important point here. I’ll tell you guys how I’ve used it in the past. I was actually just opening up Zillow on my phone right now because I still have a lot of these saved searches, but you can save searches on Zillow. So for example, let’s say that you want to flip a house and for whatever target city you have on your list, you can save a search where it says, Hey, for any listing that goes for sale that’s between this square footage and this square footage or this price point and this price point or this bedroom count and this bedroom count that has certain keywords like TLC, as is, damage, repairs needed, whatever it may be. You just kind of stack all these keywords that someone might list in a home that could be a good potential for flipping.
You’ wake up every morning, you’ll get a fresh report from Zillow saying, “Hey, here are all the new homes that match your search.” And that’s kind of like your targeted list to go look after. You can look at homes that have been listed for a long period of time. So if your average days on market is X and you set your search to be like, “Hey, I only want to see properties that are listed 2X,” you can do it that way. And then even kind of the trickier piece, if you start tracking those listings and you see which ones start to fall off that didn’t sell, well then there’s an expired listing that you can maybe just go reach out to the seller directly even. But that’s the way that I’ve used the MLS is very targeted searches, either looking at properties been listed for a very, very long time or trying to be the first one to a property that just got listed, both bookends of that time spectrum immediately when it lists or after it’s been listed for a long time, I found the most success.
But those are the ways that I’m using the MLS. And anything that you’re doing, Ash, MLS wise, it’s also been useful for you?

Ashley:
I love going in reverse and seeing what’s been listed the longest, so sorting them by newest. And then it’s always exciting to see the new things, but I also like to see what’s sitting. I also like to go and look at what’s pending and I like to go back to the history of the property where it says the day that it was listed and then the day that it went pending. And I like to see how long that period was. So did it go pending within three days? I mean, that means it sold really fast and probably above asking in my area. Did it sit on the market for 60 days? Then it probably sold for under asking. So I really like to go and use that aspect of it as far as for research and stuff for my own things. But yeah, as far as searching, I go down rabbit holes still.
I have my selected searches save, and then I also take the map and just zoom all over to the different areas that I’m interested in and just hope that I didn’t get an alert for something and there’s something new and exciting. But I’m not actively looking to buy a deal right now anyways, so it’s all just for fun. But yeah, I would say my biggest thing is going back to sorting by newest, sorting by newest, and then looking at what is still sitting and how long it’s been sitting and then looking at the pending to be able to figure out how long things are sitting on the market.

Tony:
All right. Let’s talk about the next strategy, which is word of mouth. And I have actually, maybe by referrals, but by just the word of mouth we’re going to talk about right now, I’ve never gotten a deal by word of mouth where I was just in conversation and someone’s like, oh, actually I know someone that’s selling a house like that. Now Ashley, on the other hand, she’s like the resident expert of just like –

Ashley:
Oh, Tony, hold on. My neighbor’s outside rightnow. He said his friend’s got a property for sale. He wants to.

Tony:
I would not be surprised if that was actually happening right now and someone’s knocking on Ashley’s window.

Ashley:
He actually really was going on to get his mail though.

Tony:
Someone wants to sell a house. But yeah, Ashley is like. Ashley, what’s the secret, the book, The Secret? The Secret talks about, what’s the word when you just think about something and. Oh, manifesting.

Ashley:
Oh, manifest. Yeah. I would say that I do the opposite because they literally come to me when I’m not looking for deals and it’s like, “Oh God, now I got to figure it out. I got to pull money out from underneath my mattress.” So

Tony:
Word of mouth, guys, is just that you’re sharing with everyone in your network who you are, what you do, and what it is you’re looking for. I’m a real estate investor. I buy fix and flip homes in the local area. I’m looking for properties that are three bedrooms, two baths, rent style homes, 1500 square feet max that are needed some love. And you just share that with everyone that you know, people who play sports with your kids, your hairdresser, your barber, the clerk at the grocery store, the person at the post office, all those different places. Everyone knows what Tony and Ashley do and what kind of deals they’re looking for. And then eventually someone’s like, “Oh wait, I think I might know someone who can actually work with you or give you that kind of deal.” So it’s best if you’re in a small.
I wouldn’t even say a small town, but if you’re in a town where you’ve got a lot of network and you’re good at talking to folks and you enjoy that part of it. And I think the advantages of this approach, and we’ve seen it happen with a lot of guests as well, is that you get deals that would just been really, really tough to get otherwise. Sometimes impossible. I’ll give you an example. We just recently interviewed a guest and he knocked on his neighbor’s door trying to buy their house and they’re like, “We don’t want to sell, but hey, we know the neighbor down the street actually. He’s actually about to move and he might be willing to sell.” And that investor ended up buying that neighbor’s house. That’s the perfect example of word of mouth where it’s just people knowing you and knowing what you want to do and sending you deals that otherwise you probably would’ve never heard of before.
And the benefit of this approach is that you’re not fighting with a million other investors the same way that you are on the MLS. Oftentimes, you might be the only person talking to that seller because they haven’t gone to market yet. They haven’t done all these different things. Maybe they haven’t gotten postcards from other wholesalers about their deal. You are the only option. So if you can find a solution that’s a win-win for both of you, then they get the property off their hands and you get a really, really good deal.

Ashley:
I think another thing you said about if you’re in a smaller town, you know more people or whatever, that’s an advantage, but also the fact that there’s usually less investors too. I think that was kind of my advantage for a while is that there wasn’t a lot of people that were investing when I started or talking about it at least where I was sharing it on social media. I would talk about it with my friends where at the time I was in my young twenties and nobody I knew my age was investing in real estate. And if they did, they didn’t talk about it or anything. But the other investors that I knew were older men that still had full-time jobs doing something else, but had some real estate on the side. So I think that was something too, is that it was such a small community and there are just not a ton of investors in the community too.
I

Tony:
Think the only drawback to this strategy is that it’s just not very consistent.

Ashley:
Yeah. You can’t rely on this as your only deal flow.

Tony:
Yeah, because you could get something today and maybe it’s months before you hear something else. So it’s not like the MLS, you can just turn it on and it’s there. It’s not like direct mail where you send out X number of mailers, you’re going to get this many back. It’s not like cold calling people where you make enough phone calls and people pick up. So I’d say unless you disagree, I just feel like that’s really the only big disadvantage that’s unique to this strategy.

Ashley:
Yeah. You can’t track any metrics on it. You have no way of knowing who your actual leads are, who are the motivated sellers, who potentially would sell to follow up with them. If you’re doing an email campaign or something, you can see who opened your email at least, even a text message or who answered your call, maybe answered a couple questions and you know that they’re a warm lead now. But I think one of the things that you could do is go in local Facebook groups of the market you want to invest in and put it out there is to be like, “Hey, I’m looking for this type of house. Does anyone have anything for sale?” I’m in a group like that in my area and just people post all the time and I don’t think they’re investors. They could be, but literally all they’re saying is like, “Hey, I’m looking for five acres to build a house on.
Does anyone have anything they’re thinking of selling? I’m looking for a three bed, two bath house. If I had two bedrooms, maybe couldn’t make that work. Did anybody have anything?” And there will always be tons of comments. They’ll tag real estate agents, first of all. If they know of someone, they’ll tag that person and be like, “Hey, weren’t you thinking of selling this?” And then people saying, “Hey, DM me. I have something that I’m thinking of listing in the spring or whatever.” So that’s always an option to do is every once in a while just post in there. I would just keep it as short and generic as possible to see what can be brought to you. I wouldn’t be like, “Hey, I’m an investor. I’ve been investing for three years now. I’m looking to get my third deal. I want to buy a duplex.” I would just keep it as.
All

Tony:
Right. Number four, which is somewhat related to word of mouth, but it’s pocket listings and agent relationships. So a pocket listing is slightly different than just a word of mouth transaction. A pocket listing is actually coming from an agent, but it just means that they haven’t actually published it live for the entire world to see. So sometimes an agent might keep a pocket listing because they’re like, “Hey, I know if I list this one, it’s just not going to go well. So I’ve got you here.” Sometimes they have a pocket listing because they just haven’t actually listed it yet. And maybe they just signed the contract with the seller today and you’re there and they’re like, “Actually, I think I might be able to sell this without us even going to market and doing the whole rigmarole of listing it.” So there’s oftentimes a benefit for the agents as well, but a pocket listing means that it’s an agent’s actual listing, but before they mass market on the MLS, they’re going to a select number of people they trust first say, “Hey, do you actually want first dibs on this deal?” It’s great for someone who obviously has relationships with those agents already and that it takes time to build, and it’s great for someone that’s got the ability to move quickly, the ability to confidently close, because a lot of times when an agent is giving you a pocket listing, part of the reason they’re doing that is because they want certainty of close.
It’s like, “Hey, this is a deal that traditional financing isn’t going to work with. So I got to make sure I take this to someone that actually has the funds to get it closed. Hey, I’ve done 10 deals to Ash. She always gets it to the finish line. Let me go take it to her to make sure that this transaction gets done and I take care of my seller.” So it’s for someone who has that certainty of their ability to actually close in the transaction. And even if you’re a rookie investor, it doesn’t mean that you can’t have that certainty, but either A, you’ve got the funds, maybe you’re pulling on a HELOC, maybe you’re partnering with someone else, you have the cash ready, but being able to quickly close, I feel like will be one of those barriers that you have to tackle. But the advantages here is much like the word of mouth, is that you’re getting access to a deal without fighting a bunch of other potential investors.
And because these are agents who solicit homeowners for a living, it tends to be a more consistent pipeline of deals coming your way. And there are real estate investors out there who the majority of their deal flow comes from agent relationships. In fact, I have a buddy, his name’s Brian Davila, he’s based out of Vegas, and his entire wholesaling operation is really based not on going after homeowners, but on going after agents and trying to get access to their pocket listings.That’s his entire strategy for wholesaling. So you can really build a meaningful deal pipeline out of the strategy by itself.

Ashley:
I’ve actually got a lot of pocket listings too as part of my portfolio and a lot. Well, the majority I would say were estates where they went to an agent, they wanted to sell it, the houses are full of stuff, they need repairs. And so the agent says, “Well, I know Ashley, would you like her to take a look at it?” And then I come in, look at the property and things like that. So it’s usually people who are looking for. They don’t want to have to go through showings and getting the property show ready, and they would rather just get it done and over with. They’re grieving because they’ve lost someone. So those have been the majority have been estates. I think there was maybe a couple other ones that weren’t estates. I don’t remember exactly what the reasoning was why those were kind of like pocket listings done, but most of the time it’s because they’re not turnkey properties.
They’re not beautiful properties that are going to command way above market listings. So if they’re priced right or whatever, I will buy a pocket listing. There are some rules around pocket listings for agents though. When a property is officially marketed to the public, you have to list it on the MLS within one day or something like that. I really don’t know these rules, but there is something like that too. So if you are a newer agent and you haven’t heard about pocket listings and you maybe want to build a buyer’s list of investors and make sure that you’re aware of what the rules are for pocket listings so that you’re following them. I’m sure your broker can guide you.

Tony:
I think the only thing that I’d add to the strategy is that if you do want to get good at getting more pocket listings sent your way, just spend time talking to more agents. My buddy Brian, who I mentioned, he literally has a team of people who just cold call agents all day and say like, “Hey, here’s who we are, here’s what our buy box is, here’s what we’re looking for. Here’s how many deals we close on a monthly basis. We’d love to get on your list of pocket listings.” So that’s one approach. But obviously if you’re not doing that level of volume, it’s clarity on the buy box, which was step number one. And then just doing your own outreach to those agents, say, “Hey, if you find something, just know I’d be a willing participant to take a look at that deal and build those relationships.” Strategy number five is working with wholesalers.
Wholesalers for folks that aren’t aware, you can think of them as professional deal finders, ideally professional deal finders, but that’s the role they’re supposed to serve. So wholesalers basically through different marketing channels, generate leads of people who are looking to sell their homes below market value. Sometimes those marketing channels are ads on television and radio. Sometimes that’s ads on Facebook and Instagram and Google. Sometimes it’s direct mail, sometimes It’s door knocking, it’s cold calling. They all specialize in different strategies, but the end result is they get a homeowner who’s willing to sell their property at a discount. And sometimes, most of the time it’s because the property’s in distress, needs a lot of repairs. Sometimes the seller’s in distress. They’ve got a divorce, they need to sell quickly. Someone passed away, they don’t want to deal with it. They’re packing up and moving across the country for a new job and they have to close quickly.
So either the property or the seller are in distress. And the way that wholesalers make money is that they talk to the seller, they place the property under contract at one price, and then they resell that property to you at a higher price. So maybe they’re under contract at $200,000, they resell that contract to you for $250,000. They get to keep that difference of 50K. That’s how a wholesaler makes their money. So that’s what wholesalers do. The advantages of working with the wholesaler is that they’re doing all the hard work to go source the deals. You just have to make the relationships. They’ve already done all the hard work to make the deals. So it’s not nearly as consistent as what you’re going to see on the MLS. I don’t think anything matches the MLS in terms of volume, but it’s more consistent if you have a big enough roster of wholesalers where you can get deals sent to you every day.
This was several years ago where I went into a bunch of different Facebook groups in the areas that I’m looking to invest. And I’m pulling my phone here because I’m probably still every single day, but I put my buy box in a bunch of Facebook groups saying, Hey, here’s why I am. Here’s what my buy box is. Wholesalers send me your deal. And every single day, I just pulled this up, literally every single day, there’s five to seven emails in my inbox of properties that I could go buy. So there’s enough wholesalers out there to put on your market to keep you steadily kind of looking at deals and

Ashley:
Analyzing things. Some of the negatives are that you have to usually close quickly. A lot of times you have to pay cash for the property. You can’t really rely on the numbers that the wholesaler is giving you. A lot of wholesalers will tell you what the rehab cost will be and what the ARV will be the after repair value on the property. A lot of times these are not accurate because once again, they are trying to offload the property, sell the property and make a nice assignment fee on it. So you have to do your own due diligence and you have to do your own estimate on the property. Also, you should be aware of different rules, laws and regulations around wholesaling in your state specifically. Tony, there are some states that have completely outlawed wholesaling, correct?

Tony:
I’m not a wholesaler myself, but I believe so. And I believe there’s even maybe more states that have. You have to have a license now to wholesale, whereas before you didn’t have to be a licensed agent, but there are states that are moving towards like, you’ve got to have your license the same way that a realtor would. So definitely check the local laws and regulations for your state. I

Ashley:
Just looked it up and it says it’s not completely illegal, but heavily restricted or regulated in some states. So

Tony:
It’s getting tricky, right? So it’s trickier out there for wholesalers these days, but they’re adapting, they’re figuring it out and they’re still out there in full force. So again, check your state, see how restrictive it is, but wholesalers could be a great way to find the right deals.

Ashley:
Okay. Now onto number six, direct to owner and off market outreach. So I haven’t done a lot of this, but this is where you are going directly to the seller. You are going to find your own leads. You are going to find your own sellers. And this can be done by sending text messages. This can be done by writing letters, doing a mail campaign. This can be by calling people and asking if they want to sell their house. So this could be door knocking even. So this is where you’re cutting out the wholesalers, you’re cutting out agents, cutting out any middleman, and you are going direct to the potential seller. So you have to do the work. You have to do the mail campaign. You have to set up usually a service where you can blast out text messages, but you have to follow, again, rules, laws and regulations against spamming people.
The same with phone calls. You can do skip tracing to get the phone numbers of people that kind of fit your buy box, get the numbers for the property owners and do robocalling and you can outsource to a call center or you can make the calls yourself. Re simply even has AI agents that will do the calls for you too. But some of the benefits of doing these is you’re cutting out the middlemans, you’re not paying a commission, you’re not paying an assignment fee. So there’s more room to make a better price because you don’t have to account for those things to be taken off the top. One huge advantage I think with this is that you are getting direct to the seller to be able to negotiate. Sometimes it is nice to have a middleman, but also you’re playing telephone. You’re playing telephone from me to my agent, to their agent, to them.
In New York State, then there’s attorneys involved even, and then it’s even another additional layer of somebody that you’re playing telephone with and it’s going from person to person to person to person and things can get easily miscommunicated. One example I always think about is seller financing and explaining to someone the tax advantages of that. I don’t get to say when I’m working through agents really, if the seller’s agent doesn’t understand seller financing or doesn’t understand seller credits or doesn’t understand something I’m trying to negotiate into the deal, most likely they are not going to explain it correctly to their buyer. They’re not going to be an advocate for the buyer to accept this. So that is one advantage is you get to be face to face with the person and then also too, that you kind of cut out the middleman and then you’re also cutting out those expenses like the commission or assignment fee.

Tony:
In terms of the drawbacks, there are a few big things that come to mind for me. Number one is that this isn’t like an instant kind of spigot that turns on for you. So we talked about MLS. I can literally open up my phone at any point and any time of the day and go find a bunch of deals to go look at. When you’re doing your own direct outreach, there’s usually a long kind of warmup period before you can actually get to a point where deals start closing for you. And some of the folks that we talked to that go off market direct to seller, it’s six months. James Zehner talks about how he knocked doors for like a year before he got his first off market deal. So it just takes time to build that flywheel. So if you need a deal like today, typically this isn’t going to be the best approach.
Second is that, to Ashley’s point, you have to make sure that you’re following all the rules and regulations as it relates to outreach. If you’re texting people, there are guidelines around, I think it’s called TCPA where you have to make sure that you’re following those guidelines. I’m sure different states have different rules around mail and what does that look like? And if you’re calling people, so you’ve got to make sure you’re on top of what those look like for your local city, state and otherwise. And then I think that maybe the bigger downside that is maybe a little hidden is that depending on how good you are at this, it could actually end up costing you more. A lot of people want to go direct to seller because they feel it’s going to give them the best deal. And oftentimes that can be true, but let’s say that you’re really, really bad at direct mail.
Let’s say that you’re really, really bad at selling people on the phone or those face-to-face conversations and you’ve got a really, really low conversion rate of, “Hey, we send out X number of mailers and we get back this response.” If your response rate is really, really low because you’re not good at it, you end up spending more money on mailers and time and all those different things than if you would’ve just paid the wholesaler an assignment fee. So you’ve got to make sure that if you are going to go down this path of going direct to seller, that you’ve got the skillset and the proper training to execute on it to actually make it a cost effective model for you.

Ashley:
Now let’s look at number seven, retiring landlords. And I bought a portfolio from a retiring landlord before. And one of the big advantages of this is that if they have a smaller portfolio, it is way easier for them to retire by selling one person their whole portfolio or at least a large chunk of it than having to individually sell each single property to different people and having to do a ton of different transactions, a ton of different showings. So that’s just one advantage for them even, but also for you to be able to buy a portfolio and buy multiple properties in one transaction compared to having to go out and do all these separate transactions to try to build up your portfolio. This is more common for long-term rentals than I would say short-term rentals, but hey, who knows when Tony’s getting time to retire, he might offload all of those Joshua Tree properties that someone can snatch up a whole bunch of them.
But I would say more common small multifamily properties and long-term rentals, especially with boomers retiring that there may be lots of opportunity out there. And I will say that it probably is not very common for boomers to have huge short-term rental portfolios that they’ve owned for a long period of time, maybe lake houses or maybe different vacation properties like that, but it wasn’t as popular, I would say, as it is now. And long-term rentals, they could have held for 30 years where you’re looking at advantages of they have no debt on the property for holding it for so long. They are going to pay a ton in taxes if they just sell the property and pay capital gains on that. And then also they have the opportunity to most likely do some kind of creative financing like seller financing where they don’t absolutely need a lump sum of cash upfront maybe.
And they can be the bank do the seller financing that also offsets their tax burden and lowers their tax bills. So there’s benefits to both sides of that. But that’s one thing I love about the retiring landlord is usually there’s a lot more room for opportunity in how you finance the deal and getting creative with it. The portfolio that I bought, I bought some at once. Some were cash, some were I used a line of credit and then the rest were seller financing. And then two years later I bought the rest of the portfolio. So it wasn’t even like I had to do it all at once too. So that’s just some examples of how you are able to get these portfolios from retiring landlords.

Tony:
Yeah. Just the only disadvantage, and I’ve personally never purchased from a large portfolio from a retiring landlord, but I did get pretty deep into conversation when we were investing in Shreveport, this wonderful woman named Mary. And we had a long conversation about her portfolio, but the reasons I didn’t move forward with it was because really I guess there were a few reasons. Number one, deferred maintenance. Number two, really, really poor kind of bookkeeping and record keeping to confirm some of the actual revenues and expenses. And then they were just still asking a little bit too much given what that was. So obviously the rents were low, so I had the opportunity to bring them up to market level, but because there was so much deferred maintenance, it was going to be a really big capital expense to get all these properties to the point where I could actually increase the rents.
And when I balanced those two things out against what they were asking for, it just didn’t work for me. So I think that’s the only disadvantage is you really wanted to complete your due diligence to ensure that the asking price allows you to still execute the business plan and get the rents where they need to be, which is true of any underwriting or any property that you’re looking at. But that was a disadvantage I saw. And from you, Ash, given that you’ve done this a few times, anything that we’re not considering?

Ashley:
I would say maybe the only. No, I don’t think so.

Tony:
All right. And the final one here, number eight, Ash and I are just going to rattle off a few bonus channels that maybe you hadn’t considered that you can go take a look at. So one is HUD owned in Fannie Mae Home Path properties. So if HUD or Fannie Mae have to take back properties or they get control of properties for whatever reason, you can actually go bid on those properties. Now, don’t quote me here because I’ve never purchased through those programs, but I want to say that they have a timeline where it has to be someone who’s buying for their personal property first. And then after that timeline, then investors can go in afterwards. Ash, do you recall that? Does that sound familiar to you?

Ashley:
Yeah. They usually open up first to, if it’s going to be your primary residence to a certain amount of window. If they don’t get any offers or accepted offers that they don’t accept any of them, then after that window closes, they open up to investors. And still, if it’s going to be your primary home, you still can bid on it and look at it, but they do give that time for just primary residents to be able to submit offers, to not have to compete with investors. Okay. So the next thing is local banks and actually going and talking to the loan officers at that banks and seeing if they are actually foreclosing on any properties or if they know of anyone that maybe wants to sell their property, but building those relationships with people who deal with real estate investors or deal with homeowners, so loan officers, but also property managers, so property management companies in the area, they’re usually one of the first to know that an owner is going to sell their property if they manage that property.
And sometimes they will kind of keep the house in sale because then they’ll know that they are keeping the property. But if you can get on their list to be notified when they have a property that they’re selling for an owner too, that’s an advantage. Going to investor meetups, going in the BiggerPockets forums and just saying, “Hey, I’m looking to buy a property in this area,” searching where other people are investing if maybe you need to find a new market. And then local online groups, so Facebook groups, connecting with people on Instagram that are investing in your market. And then there’s also auctions and tax sales. So the Marshalls, the US Marshalls, they seize land and then they have auctions to sell it. I actually went to one before and it was really interesting. And the guy that I went with actually ended up buying the piece of land.
He was the only person bidding, so they got it exactly what it was, but it was like a prime piece of property. But they only notify the people who have the adjoining land. They send them a letter and just saying, “Hey, just this parcel of land that is adjacent to your property is going to be sold at auction. Here’s the date. Here’s where you need to be if you are interested or whatever.” And then I think you sign up in advance as a bidder. But there’s a ton of different government entities that do different auctions. There was one by my lake house recently. It was just a small parcel of land and it was listed because it back taxes. The person hadn’t paid the taxes on it and it was being put up for auction. It was just an online auction up there and they do it once a year and you just sign in, you register to bid and then you can bid on any of the properties.
So there are different. I would just go into Claude ChatGPT and ask in my area, what are some of the properties that are for sale? I bet you could actually find a lot of these tax auction websites just from using AI in your area.

Tony:
Last thing that we’ll wrap up here guys is that we gave you a bunch of different strategies, but none of this actually helps if you don’t execute on what we’ve talked about. And I’m a big fan of tracking things and data provides clarity and you can make the right move based on the right data. So if I’m a rookie sitting in this seat and I haven’t yet closed on my first deal, the things that I would be tracking are one, just did you complete your buy box, yes or no? But once you have your buy box complete, how many deals have you analyzed in a rolling 30 day period? And the goal is to never let that number get below at least one per day. And if you can do that, analyzing a deal every day for 30 days straight that meets your buy box, there’s a really, really good chance you’re going to find at least one or two properties that are worth really, really pulling the trigger on.
And I know that because I’ve seen it happen time and time and time again. So that would be my challenge to you guys is dedicate and focus yourself to one deal analyze that meets your specific buy box every day for the next 30 days.

Ashley:
And we want you guys to track this. So you’re going to track your new leads. You’re going to track the amount of properties that you are analyzing if that ends up being once a week. You’re going to track your offers submitted and you’re going to actually track follow-ups. So how often are you following up on a property? When did you follow up? Did you follow up? And then any contracts and closing. So you can use a project management board to track this. You can use a Google worksheet, whatever you want, pen and paper to track this. Thank you guys so much for joining us today, and I hope that you will look into some of these ways that you can find deals in 2027 or start this year. Take Tony’s advice and start analyzing, analyzing, analyzing, and it’s just going to make you more comfortable and better and help you get over that analysis paralysis.
I’m Ashley Hughes Tony and this has been an episode of Real Estate Rookie. Make sure I subscribe to our YouTube channel and if you haven’t already, check out biggerpockets.com. We’ll see you guys next time.

 

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Forget Buying All Seven: The “Magnificent Seven” Stock Most Likely to Double by 2028


I think the megacap technology businesses — otherwise known as the “Magnificent Seven” — are fantastic businesses. These include Nvidia, Tesla, Alphabet, Apple, Microsoft, and Meta Platforms. But it is the seventh member of the Magnificent Seven, I think, that has the best chance to double by the end of 2028: Amazon (AMZN +1.00%).

The technology player is a beneficiary of artificial intelligence (AI) and also enjoys massive economies of scale in its e-commerce delivery business. Here’s why I think the stock can double by the end of 2028 if the AI spending boom continues.

Today’s Change

(1.00%) $2.52

Current Price

$253.71

Amazon’s cloud growth

The AI boom has been a huge boon for Amazon’s cloud computing division, Amazon Web Services (AWS). Revenue grew 37% year over year last quarter and hit $148.4 billion over the last 12 months. If AWS’ backlog growth is any indication, along with its massive capital spending plans, this revenue growth should accelerate in the quarters ahead.

AWS likely has a path to doubling by 2028, driven by massive spending plans from AI start-ups. It also has fantastic profit margins, at at 37% over the last 12 months. If AWS revenue can grow to $300 billion, segment profits will reach $100 billion even if margins slip back closer to 30%. That is more than the profit Amazon as a whole generated in the last 12 months.

An Amazon delivery van.

Image source: Amazon.

Underrated e-commerce margins

We can’t forget Amazon’s other division, which houses its e-commerce platform, consumer electronics, and other services such as Amazon Prime subscriptions and advertising.

Combined, the North America and International segments now account for $627 billion in retail revenue. In the next few years, there should be continued growth from e-commerce taking share in markets around the world, along with margin expansion due to economies of scale. Plus, Amazon has seen strong growth in its high-margin advertising division, which was up 26% last quarter.

Lastly, it has expensive projects in development, such as the Amazon Leo satellite internet service. This is planning to begin operations later this year, and could be a nice growth engine that also helps profit margins at a greater scale. Amazon has also been investing heavily in areas such as faster delivery times, warehouse robotics, and self-driving vehicles. Once these technologies are implemented across its e-commerce supply chain, the business should see greater operating leverage and higher margins.

Overall, one should expect retail sales to continue growing in the double digits (both segments grew by 15% or more last quarter), with solid margin expansion. That could get the combined revenues to $829 billion after two years of 15% growth. Assuming profit margins can expand to 10%, that is $83 billion from the two segments two years from now.

AMZN EBIT (TTM) Chart

AMZN EBIT (TTM) data by YCharts

Why Amazon shares can double

Right now, Amazon has had EBIT (earnings before interest and taxes) of $98 billion over the last 12 months. Combining my two estimates from the above section, I think this figure can close to double by 2028.

With a market cap of $2.7 trillion, Amazon trades at around 27x its trailing EBIT. Assuming this earnings multiple remains in 2028, then Amazon stock can close to double by the end of that year.

But close does not mean actually doubling. Where will the extra gains come from? Amazon has been a major investor in Anthropic and may own around 15% of its stock heading into Anthropic’s upcoming initial public offering (IPO) in October or November. At an expected valuation of $2 trillion, Amazon’s stake may be worth hundreds of billions of dollars. Add that to the forward returns, and I think Amazon is a fantastic bet for investors right now, and perhaps the best Magnificent Seven stock you can buy today.

Fed supervisors knew SVB was vulnerable — and failed to act


The conclusions were unsparing: “Our supervisory staff knew, or should have known, about these vulnerabilities as early as March 2022,” Bowman said, summarizing the report.

SVB’s deposit base was 94% uninsured and concentrated heavily among venture capital-backed technology companies, according to the review, as reported by Bowman.

When the bank announced a $1.8 billion loss on securities sales and sought additional capital, depositors fled, triggering a run that regulators could not contain.

Federal officials, including the Federal Deposit Insurance Corporation (FDIC) and the Federal Reserve, moved to shutter the institution and extend deposit protection beyond the standard $250,000 limit.

A culture of caution that proved costly

The review identified a “long-standing culture of risk aversion” as a central driver of supervisory inaction.

Targeted U.S. Bank Offer: Spend $250, Get a $25 Statement Credit


Targeted U.S. Bank Offer: Spend $250, Get $25 Back

U.S. Bank is sending out a targeted spending offer to select credit cardholders. Eligible customers can earn a $25 statement credit after making at least $250 in net purchases within 60 days of enrollment.

Cardholders must enroll by October 2, 2026. One important detail is that U.S. Bank says to allow up to seven days for enrollment to process before purchases become eligible toward the $250 spending requirement.

Important Terms

  • Enroll by October 2, 2026
  • Spend at least $250 in net purchases within 60 days of enrollment
  • Allow up to seven days after enrollment for processing before beginning qualifying spend
  • Earn a $25 statement credit
  • Credit should appear on the statement following the one in which it is earned
  • Net purchases exclude credits and returns
  • Account must remain open and in good standing
  • Offer can only be enrolled in once
  • Offer applies only to the specific U.S. Bank card receiving the promotion

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Investing For Dividends: How It Works, What It Pays, And Where To Start


Key Points

  • A dividend is a cash payment a company sends to shareholders, quarterly for most U.S. stocks.
  • Reinvested dividends account for 85% of the S&P 500’s cumulative return since 1960, according to Hartford Funds.
  • In 2026, qualified dividends are taxed at 0% up to $49,450 of taxable income (single) or $98,900 (married filing jointly).

The short answer: investing for dividends means owning companies (or funds that own companies) that pay you cash out of their profits, and either spending that cash or reinvesting it to buy more shares. It’s one of the oldest ways to build wealth in the stock market, and it’s also one of the most misunderstood, because the headline yield tells you almost nothing about whether the investment is any good.

Dividends matter for two reasons. First, they’re real money: a company can fake earnings for a while, but it can’t fake a cash payment to your brokerage account. Second, they compound. Reinvested dividends buy more shares, which pay more dividends, and over decades that loop does most of the work.

Here’s how dividends work, how much they actually pay, how they’re taxed in 2026, and where to open the account.

Table of Contents

What’s a Dividend and Why Does It Matter?
How Dividends Get Paid: Dates, Frequency, And Yield
How Much Do You Need To Invest For Dividends?
Dividend Reinvestment (DRIP): How It Works
Finding Dividend Paying Stocks
The Problems With Investing For Dividends
Tax Implications
Best Places To Invest In Dividends
Who Dividend Investing Is For (And Who It Isn’t)
Dividend Investing FAQ
Final Thoughts

What’s a Dividend and Why Does It Matter?

A dividend is a share of a company’s profit paid to its shareholders. The board of directors decides whether to pay one, how much, and on what schedule; most U.S. companies that pay dividends pay quarterly. If a company pays $1 per share per year and you own 500 shares, you receive $500 a year, whether the stock price went up or down. Companies that have paid and raised their dividends for decades, the Dividend Aristocrats, are the group most dividend investors start with.

The reason dividends matter more than most beginners assume is compounding. Hartford Funds calculates that 85% of the S&P 500’s cumulative total return since 1960 came from reinvested dividends and the growth they compounded, and that dividend income averaged 33% of the index’s annual return from 1940 through 2025. That second number moves around by decade: in the 1970s and 2000s, when prices went nowhere, dividends were most of the return; in the 2010s they were a small slice. If you’re building a long-term portfolio, you want that cushion.

Dividends are also a signal. A company that has raised its payout for 25 straight years has survived at least three recessions without cutting it, which is why dividend growth investing is its own strategy rather than a subset of income investing.

How Dividends Get Paid: Dates, Frequency, And Yield

Four dates decide whether you get paid. The declaration date is when the board announces the dividend. The ex-dividend date is the cutoff: buy the stock before this date and you get the dividend; buy on or after it and the seller keeps it. The record date is when the company checks its shareholder list (one business day after the ex-date), and the payment date is when the cash lands in your brokerage account, typically two to four weeks after the ex-date.

Most U.S. stocks and ETFs pay quarterly. Some REITs and a handful of stocks and funds pay monthly; many foreign companies pay twice a year or once. Your broker’s dividend calendar shows the schedule for every holding, and portfolio trackers will project your income across the year.

Dividend yield is the annual dividend per share divided by the share price. A $100 stock paying $3 a year yields 3%. Yield moves inversely with price, so a stock whose yield jumps from 3% to 8% got there because the price collapsed, not because the board got generous. The S&P 500 as a whole yields about 1.06% as of September 11, 2026, the lowest reading in the index’s history against a long-run average of 4.2%, which tells you how much of today’s market return is price gain rather than income. That’s why a plain index fund is a growth holding, not an income holding, even though it pays dividends.

How Much Do You Need To Invest For Dividends?

Any amount. Every major broker sells fractional shares now, so $50 buys a slice of a $500 stock and the dividend arrives pro rata. The question people actually mean is how much it takes to produce meaningful income, and that’s yield math.

Divide the annual income you want by the yield. For $12,000 a year ($1,000 a month):

Portfolio yield Portfolio needed for $1,000/month
1.06% (S&P 500 today) $1,132,000
2% $600,000
3% (typical dividend ETF) $400,000
4% (high-yield, higher risk) $300,000

Two things follow from that table. The first is that living off dividends alone is a late-career goal, not a starting point; a 25-year-old with $5,000 should be reinvesting, not collecting. The second is that reaching for a 6% or 8% yield to shrink the number you need is how people end up owning the companies about to cut. If you want the full argument, our piece on building a compounding dividend portfolio walks through a realistic 30-year path.

Dividend Reinvestment (DRIP): How It Works

A dividend reinvestment plan, or DRIP, tells your broker to use each dividend to buy more shares of the same stock or fund automatically. At Fidelity, Schwab, Vanguard, and the other major brokers it’s a per-holding setting (at Fidelity: Positions, then “Manage Dividends”), there’s no commission, and fractional shares mean the whole dividend gets invested, not just the part that buys a whole share. Here’s why reinvesting is the engine of the strategy: $1,000 in the S&P 500 in 1982 grew to about $97,900 by 2022 with dividends reinvested, versus about $36,900 without.

Two things beginners miss. Reinvested dividends are still taxable income in a taxable brokerage account in the year they’re paid, because the IRS treats the reinvestment as a cash payment followed by a purchase; you’ll owe tax on money you never saw. And each reinvestment creates a new tax lot with its own cost basis, which is why a portfolio tracker that logs dividends earns its keep when you eventually sell. Inside an IRA or Roth IRA, neither problem exists.

Finding Dividend Paying Stocks

There are three ways to find dividend stocks, and most investors end up using two of them.

Start with a list. The Dividend Aristocrats are the 69 S&P 500 companies that have raised their dividend for 25 or more consecutive years; Dividend Kings have done it for 50. That’s a pre-screened set of companies whose boards treat the dividend as a promise, and it’s where the reader who left our oldest comment on this page (“I start with the dividend champions and achievers”) begins too. Many of the investing blogs we follow publish their own screens of this group.

Run a screener. Every major broker has a stock screener. The filters that matter for dividends are yield (2% to 5% is the sane range), payout ratio (dividends as a share of earnings; under 60% for most industries, higher for utilities and REITs), consecutive years of increases, and dividend growth rate. A dividend growth investor weights the last two; an income investor weights the first.

Buy a fund. For most people this is the right answer, because a single ETF gives you 100 or more dividend payers and the diversification that protects you from any one cut. The three funds beginners compare most in 2026:

ETF What it holds Expense ratio Yield
Schwab U.S. Dividend Equity (SCHD) ~100 U.S. stocks screened for yield and dividend quality 0.06% ~3%
Vanguard Dividend Appreciation (VIG) U.S. companies with 10+ years of dividend growth 0.04% ~1.5%
iShares Select Dividend (DVY) 99 high-yield U.S. stocks (Dow Jones U.S. Select Dividend Index) 0.38% 3.56% (30-day SEC)

VIG is the growth-tilted choice, SCHD the balance, DVY the yield-first pick with a fee nearly ten times VIG’s. All three drop into the asset allocation of a young investor as the U.S. equity sleeve, or part of it.

The Problems With Investing For Dividends

Chasing the highest yield is the mistake that defines this strategy. A 9% yield on a stock is the market telling you it expects the dividend to be cut, and when it is, you lose the income and the price at the same time. Companies also sometimes pay out unusually large dividends ahead of bad news to give insiders a payday before the decline; if a yield looks too good relative to the company’s earnings, dividends don’t matter as much as the balance sheet does.

A dividend also isn’t free money. When a company pays $1 a share, its stock drops by about $1 on the ex-dividend date, because the cash left the company. Over time, a company that reinvests its profits well can grow faster than one that pays them out, which is why most of the biggest stocks of the last 15 years paid little or nothing. Dividends are one part of total return, not a substitute for it.

Ask why the company is paying. The good reason is that it earns more than it can reinvest at a decent return. The bad reason is that management has run out of ideas, or is paying to keep the stock price up. A rising payout ratio with flat earnings is the tell, and it’s the reason to read the quarterly report rather than the yield.

Tax Implications

How dividends are taxed depends on which account holds them and whether the dividend is “qualified.”

In a retirement account or HSA, there’s no tax on the dividend when it’s paid. Inside a traditional IRA or 401(k), dividends compound untaxed and you pay ordinary income tax when you withdraw. Inside a Roth IRA or an HSA used for medical expenses, they’re never taxed at all. The 2026 IRA contribution limit is $7,500, which is enough to hold a meaningful dividend position.

In a taxable brokerage account, you owe tax every year, even if you reinvest. Your broker sends a Form 1099-DIV for any payer that sent you $10 or more, and it splits your dividends into two boxes.

Ordinary (non-qualified) dividends are taxed at your regular federal income tax bracket, 10% to 37%. REIT distributions, money market fund dividends, and most bond fund income fall here.

Qualified dividends get the lower long-term capital gains rates. To qualify, the dividend has to come from a U.S. corporation or a qualified foreign one, and you have to have held the stock for more than 60 days during the 121-day window that starts 60 days before the ex-dividend date (more than 90 days in a 181-day window for preferred stock). That’s about two months, not six. Your 1099-DIV does the classification for you.

For tax year 2026, per IRS Revenue Procedure 2025-32, the qualified dividend rate depends on your taxable income:

Individual Income Tax Bracket

Qualified Dividend Tax Rate

$0 – $49,450

0%

$49,451 – $545,500

15%

$545,501+

20%

If you are married filing jointly, check this out:

Joint Income Tax Bracket

Qualified Dividend Tax Rate

$0 – $98,900

0%

$98,901 – $613,700

15%

$613,701+

20%

Those are taxable-income thresholds, after the standard deduction ($16,100 single, $32,200 joint in 2026). A married couple with $60,000 of wages and $30,000 of qualified dividends has $57,800 of taxable income and pays 0% on every dollar of the dividends. Qualified dividends stack on top of ordinary income, so if wages alone push you past $98,900, the dividends are taxed at 15%.

One more layer above $200,000. The 3.8% net investment income tax (NIIT) applies to dividends, interest, and capital gains once modified adjusted gross income passes $200,000 (single or head of household), $250,000 (married filing jointly), or $125,000 (married filing separately). Those thresholds are set in law and don’t adjust for inflation, so a couple at $260,000 pays 15% plus 3.8% on qualified dividends. High earners holding big dividend positions in taxable accounts sometimes offset the bill with tax-loss harvesting elsewhere in the portfolio.

The practical rule: put your highest-yield holdings (REITs, high-yield ETFs, bond funds) in the IRA and your qualified-dividend stocks and low-yield growth funds in the taxable account, if you have both.

Best Places To Invest In Dividends

The account matters more than the broker, so pick the account first. All of the brokers below are on our list of the Best Online Stock Brokers, and every one of them offers commission-free trades, fractional shares, and free automatic dividend reinvestment.

If you’re investing through low-cost index funds and ETFs, Vanguard and Fidelity are the two we point most readers to. Vanguard runs VIG and the cheapest dividend index funds on the market; Fidelity is our top-ranked broker overall, holds any ETF including SCHD and DVY, and lets you set reinvestment per holding in two clicks. Either works as an IRA provider, which is where a dividend portfolio belongs if you have room.

If you want to own a basket of individual dividend stocks, M1 Finance is the broker built for it. You set up a “pie” of stocks with target weights, M1 buys fractional shares of each, and reinvested dividends go toward whichever holdings are under their target, so the portfolio rebalances itself. It’s the closest thing to a self-managed dividend fund, and it’s also on our best investing apps list.

Get started with M1 Finance here >>>

If you’d rather not pick anything, a robo-advisor will hold dividend-paying index funds inside a diversified portfolio and reinvest for you, at 0.25% or so a year.

Who Dividend Investing Is For (And Who It Isn’t)

Dividend investing fits an investor with a long horizon who wants a portfolio that pays something in every market, a retiree or near-retiree who needs income without selling shares, and anyone holding stocks in a Roth IRA where the tax drag disappears. It also fits people who need the psychological help: a quarterly deposit makes it easier to hold through a 30% drawdown than a screen full of red does.

It’s a poor fit for a 22-year-old with $3,000 who expects the dividends to pay rent (at 3%, that’s $90 a year), for a high earner holding high-yield funds in a taxable account (15% plus 3.8% on income you’re reinvesting anyway), and for anyone who picks stocks by sorting on yield. If your goal is passive income in the next five years, the math above says dividends are the slow road; if your goal is a bigger portfolio in 30 years, they’re most of the road.

Dividend Investing FAQ

How often do you get dividend payments?

Quarterly for most U.S. stocks and ETFs. Some REITs and income funds pay monthly; many foreign stocks pay semiannually or annually. You must own the shares before the ex-dividend date to receive that quarter’s payment.

How much money do you need to start investing in dividends?

With fractional shares, $5. To generate $1,000 a month, about $400,000 at a 3% yield.

Can you live off dividends?

At today’s yields it takes a seven-figure portfolio to replace a median income, and the S&P 500’s 1.06% yield means an index-only portfolio pays about $10,600 a year per $1 million. Most retirees who “live off dividends” own a mix of dividend ETFs, bonds, and individual stocks yielding 3% to 4% combined, and supplement with withdrawals.

Are reinvested dividends taxed?

Yes, in a taxable account, in the year paid, at the same rate as if you’d taken the cash. In an IRA, Roth IRA, 401(k), or HSA, no.

What’s the difference between qualified and ordinary dividends?

Qualified dividends come from U.S. (or qualified foreign) corporations on shares you’ve held more than 60 days around the ex-date, and are taxed at 0%, 15%, or 20% in 2026. Ordinary dividends, including REIT and money market fund payouts, are taxed at your regular bracket.

Is a high dividend yield good?

Above about 5%, treat it as a warning. Yield rises when the price falls, and the market prices in expected cuts. Compare payout ratio and dividend growth history before yield; the Dividend Aristocrats list is a safer starting screen than a yield sort.

Final Thoughts

Investing for dividends works because of compounding, not because of the yield. Own companies or funds that can keep raising the payout, reinvest every dividend you don’t need to spend, hold the highest-yield pieces in a tax-advantaged account, and check the 2026 tax thresholds before you assume the income is free. Then give it 20 years.

Do you prefer to invest in dividend paying stocks?

Editor: Clint Proctor

Reviewed by: Chris Muller

The post Investing For Dividends: How It Works, What It Pays, And Where To Start appeared first on The College Investor.

I fled communism. Are Gen Z drawn to it?



I recently came across a statistic that sent chills down my spine, having been born in a communist country. According to a recent Cato Institute Survey, four in ten (38%) 18-to-29-year-olds (and almost a third of 30-to-44-year-olds) are favorable towards communism. Communism’s appeal among Gen Z is twice as high as among 45-54 year olds, and three times as high as among those aged 55-64.

Momentarily I was transported back to the economic ruin, stripped supermarket shelves of grey, repressive 1980s communist Bulgaria, and the power outages and hyperinflation that followed in the 1990s in the post-communist Soviet bloc countries.

To me, communism means being forever stuck in mediocrity, silence, and a fawning existence marked by hollow propaganda heralding non-existent equality and demanding self-sacrifice “in the name of all”. It means a ruptured relationship with the engines of a happy life, like truth, trust, empowerment and success. It means being continuously lied to by those in power, being prohibited from expressing yourself freely and repressing any big dreams of standing out from the crowd that you might otherwise have had.

What is it then that so many young American adults like about communism, I wondered, fairly certain that it was not any of the facets I associate communist regimes with.

To get some answers I interviewed Fenley Scurlock (18), co-author of Down to Business and now a freshman at Brown University majoring in philosophy, and Atlanta-based Harper Bruner (17), a senior at Stanford Online High School focusing on history.

Despite communism’s collapse in 20th century Soviet bloc countries, the last decade has witnessed a surprising surge in interest in communism and socialism among the US public and journalists globally. Analysis by my consultancy AKAS reveals that Google searches for communism have reached an all-time high in the US, up 82% since 2006. Ahrefs analysis of 684 million English-language news pages published globally between 2016 and 2026 revealed that news mentions of socialism are now on a par with mentions of capitalism, while mentions of communism, although at a lower level, are at recent high.

In our conversation, Bruner observed that young adults are picking up on the heightened communism- and socialism-related rhetoric being “thrown around” by politicians and news commentators. Indeed, President Trump drastically escalated his warnings about communism this summer, mentioning the term 81 times in the two weeks surrounding 4th July. Calling his opponents “communists” seems to be one of Trump’s midterm election campaign tactics.

Bruner explained that young people are confused and turn to Google search and AI for clarification on the cacophony of terms – communism, socialism, utilitarianism, authoritarianism – that hold no historical resonance for them, being three generations removed from the past they signify.

Contrary to the political rhetoric’s intended effect, according to my interviewees most young people are not frightened by the threat of communism or socialism. They associate these terms with a different, often more promising, economic reality rather than with a political regime, let alone an authoritarian one (another term poorly understood among the young). As Bruner remarked, “We grew up without memories of the Soviet era. We view these terms more abstractly and associate words like communism with resources rather than with authoritarianism.”

Scurlock argued that the Republican red-baiting rhetoric has backfired, triggering instead a favorable attitude towards the ill-understood concepts of communism and socialism among young people. “Republicans are used to labelling measures like universal healthcare and universal basic income […] as ‘socialism’ or ‘communism’, which they use as scare words. But when you see something that looks good for people being labelled socialism, or communism, you think, ‘Well, those things seem good, maybe that means that socialism is good’.”

At the heart of communism and socialism’s disproportionate appeal among young people lies their increasingly curtailed economic prospects, which both Scurlock and Bruner talked about at length. With 53% of US 18-to-29s favorable towards socialism but only 45% favorable towards capitalism, Gen Z evidently feel let down by capitalism. And they are indeed wrestling with unprecedented economic precarity, as the rising age of first-time home buyers indicates (29 in 1981 vs. 40 in 2025).

“I think the problem is the lived economic frustrations associated with high costs of living, soaring house prices, student debt, low student wage. So, when you live under these difficult market conditions, the ideas and promises of universal equity or wealth redistribution naturally catch your attention,” rationalized Bruner. Having volunteered to support Hispanic immigrants she was keen to speak about the extreme economic inequality she had witnessed. “Some people don’t have access to a proper education, to a house or to technology… others don’t even have access to basic things like pens, pencils, diapers, period products and paper.”

Scurlock drew a detailed picture of failing capitalism, which so many from his generation fervently averse to. “In the last 40 years …we’ve seen large corporations become a sort of authoritarian entity in themselves. We see billionaires buying media companies and influencing their trajectory, the wealthy actively donating money to fund certain political candidates that they then can make demands of. We see monopolies, multinational corporations that are too big to fail. In other words, we see something that in one sense is not actually capitalism, something like a crony capitalism.” He further laid out the extraordinary economic unfairness his generation perceives: “You see companies outsourcing labor to China, to underpaid and often underage workers. You see a high level of corruption in government due to corporate interference. Young people look at our current system specifically in America and see that this system isn’t working.”

My conversations and research left me much less shocked at that statistic that had sent chills down my spine a few weeks prior. I see that many young people are searching for alternative systems to the one so many see as broken. Politicians must listen to them and provide an alternative that does not relegate Gen Z to the sidelines of prosperity and personal fulfilment but puts them at the centre instead. In Scurlock’s words, “We want more regulation, more individual ground-level say in the economy and less of one CEO at the top throwing $100 million to secure the election of a candidate who cuts their taxes.”

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

This story was originally featured on Fortune.com