Brad Wayland Shares Insights From 80+ Exits & 20+ Years in Online Business

Brad Wayland from Quiet Light joins the podcast to share his expertise and insights into whether it’s best for you to grow a single brand or a portfolio of sites.

With over 2 decades of experience in all aspects of the online business world, he offers a TON of value to all site owners.

The conversation kicks off describing various ways to own web or digital assets:

  • A solopreneur with one website
  • A solopreneur with a portfolio of sites
  • Having a team for one website
  • Having a team for a portfolio of websites

He highlights some of the key perks and pitfalls of each approach, emphasizing that owning a portfolio may not be for everyone.

The solopreneur lifestyle allows for complete focus and dedication to one project, which can lead to potential success. However, being a solopreneur also requires managing limited time and responsibilities, which can be challenging.

Brad says that successful solopreneurs often have a long-term commitment to their work and prioritize it over other activities – emphasizing the term ‘grind’ several times.

As a result, this model can lead to significant financial success and high levels of achievement. The key though is to resist the ever-present temptation to chase shiny objects.

Brad describes how diversification of projects and thus focus can be a pitfall for entrepreneurs, and buying and acquiring multiple businesses without proper management can lead to failure. And Brad shares his personal experience buying businesses in niches he wasn’t passionate about and the negative impact it had.

He emphasizes the importance of dedicating time and energy to rethinking strategies and staying passionate about the topic.

Operating at a high level and achieving long-term success requires a special mindset and creativity. Simply following a checklist of industry trends and best practices is likely not enough to stand out to the best in your niche.

In short, Brad recommends doubling down on focus and intentionality in business. He encourages you to prioritize and not spread yourself too thin.

If you’re an exceptional entrepreneur (such as Syed Balkhi – the example he uses) who can attract excellent people and manage several projects at once – then great! But it’s best to reflect honestly on your abilities – and most people will find they’re best served focusing on a single project and grinding to the finish line (in the form of a big exit to financial freedom).

Watch The Interview

Topics Brad Wayland Covers

  • How he got into online business
  • Learning SEO
  • Building a portfolio
  • Buying 26 businesses
  • Exiting his portfolio
  • Getting into QuietLight
  • What Brad thinks of portfolios
  • Importance of focus
  • Addiction to buying
  • Diving into unfamiliar niches
  • Building 1 brand vs a portfolio
  • Dangers of diversification
  • What a portfolio owner needs to succeed
  • Who to mitigate risk
  • What every online business has in common
  • And a ton more important insights you should hear…

Links & Resources


Jared: ​All right. Welcome back to the Ditch Pursuits podcast. My name is Jared Bauman. And today we are joined by Brad Whalen with Quiet Light. Brad, welcome on board. 

Brad: Hey, thanks for having me today, Jared. It’s good 

Jared: to have you here. I feel like we’re getting to know some different people over the years, of course, but some different people from Quiet Light.

We’ve had a number of your colleagues on in the past. Um, Uh, but to talk about different things today, we’re talking, uh, about, uh, kind of a topic that does come up quite a bit here on the podcast as it relates to owning a portfolio of websites and your experience in that, um, why don’t you give us some background, let the niche pursuits audience get to know you a little bit more before we dive in.

Brad: Sure. Thanks. Yeah. Uh, I graduated college, uh, around 2002, uh, had a finance degree, uh, thought about going into financial planning, uh, ended up getting a. A corporate accounting job and, and got some, some finance chops there, balancing GL accounts and doing sales and use tax for Camping World. Um, literally thought of that cube as like a jail cell within like about two weeks.

Like I’d, I’d run my own painting business through college. I’d owned several businesses in high school, whether it was selling gum out of my locker, bracelets or whatever. I just was, uh, always trying to figure out a way to make a buck and. Uh, getting into that corporate America world where my dad had thrived.

I thought this is gonna be I’m gonna be you know I’m gonna be a businessman and I figured out very quickly like I’m gonna get fired from this job Like I’m not even gonna make it like these people are gonna see right through me Um, and so I started kind of, uh, seeing what was going on and, uh, other types of opportunities.

And so, uh, I got a job offer from Edward Jones, thought about going down that path. I was interested in, in financial planning, retirement planning. And a couple of friends of mine had a custom t shirt business that was selling t shirts to groups. And they said, Hey, we’re, we’ve got like 10 employees and we need like some business development.

Would you want to come on here instead? And kind of see what’s going on and they were doing kind of a, sort of a local college rep model where you, you know, had people on campus trying to sell the shirts for you. And then you’re wanting to ship, you know, orders of 50 to 100 shirts. And so I came in and they had been tinkering around with this idea of launching a website for selling group orders of custom t shirts.

And so in 2004, started looking at that. Uh, we really had no idea what we were doing. A local firm had built a, a really. rudimentary website for us for doing it and I couldn’t figure out how the traffic actually got there and I became super enamored with the data behind that and so Started asking the firm like what’s going on here?

Like well, we’re just putting 25 a day into this Google AdWords platform I’m like, okay. Well, and how do you know if that’s the right number like we don’t And I’m like, okay, well, how do you measure? And they were like, what do you mean? And I was like, there’s got to be some way of measuring. Like, do we know anything about these people?

And they’re like, no. So at the time, actually Google had not completed their acquisition of urchin yet. And so, uh, we went out and paid for index tools, 200 a month to have analytics, you know, on our website. And then shortly after Google analytics actually kind of rolled out and we. But I got really enamored with ranking for free is what I used to call it.

So, you know, I was like, Hey, I want to know how to rank for free. So I started going to the, the popular circuit at the time, which was like search engine strategies, New York and stuff like that. And, you know, you didn’t have a laptop battery that could even keep up for even 10 minutes, uh, you know, back in those days.

So you would write notes with your hands. Uh, vigorously. And so I, I went deep down the SEO rabbit hole for many years and I, I would love to tell you that I figured it out in like three months, but it wasn’t very glamorous. I spent from 2004 to 2006 really just failing over and over again, working for some friends, making no money.

Um, but in 2006 I finally had had enough failure to be like, I know what we need to do. So we rebuilt the tech from the ground up. We built a design studio that at the time was built in Flash that was, uh, a very forward thinking product at the time. We built the site to rank. We put it out there in 2007 and I woke up the next morning to the homepage of Gizmodo saying Blue Cotton has built Photoshop like environment for creating custom t shirts.

The website crashed. We got hundreds of links the set the first day from all the wannabe gizmodos and then about a month later adobe linked to us from adobe. com Showcasing what we had done with flash at the time and that really put us on the map and we rode that from basically a million in sales and six employees to a hundred and thirty employees and operating out of a hundred ten thousand square foot production facility Um, you know, a decade later, and so, and, and during that time, I was really interested in search, and I was really interested in e commerce, but in the custom t shirt space you have to really be interested in running a factory, and that was a big challenge for us.

So, all that time, all I really wanted to do was stuff on the web, but we were always bogged down with trying to get orders out the door. And so, you know, we had this, you know, basically eight figure business with 130 employees that sometimes felt like a 130 headache. And every shirt had to touch 22 hands before it went out the door.

And it was like, there’s gotta be an easier way to make money than this. Now that was a good, that was a profitable business. It was a good business, it’s a good business still today. Um, but, I started thinking more in terms of, You know, what am I going to do with this skill that I have? I understand search.

What can I do with that? Do I have to have the orders touch 22 hands? And actually, I kind of skirted over this, but because all the revenue for the company started going through my department. I was able to do an equity swap some other e commerce things that I owned and so I got some ownership in the company And it ended up being very meaningful for my family But it still didn’t change the fact that my partners were more interested in running that Factory b2b doing fulfillment for people business and I was mostly interested And just anything internet commerce, whatever that was.

And so, uh, one day I was actually talking with a friend who had a free vector site on the web that, you know, today is probably close to a hundred million dollar company in terms of valuation. And he said, I’m looking at this design blog for 50, 000, but I think I’m not going to buy it. And I was like, Oh, really?

So how does it work? He’s like, Oh, it’s just, you know, just ranks for articles and WordPress. There’s, like, AdSense and stuff like that on top of it, and I was like, Right, so, no 22 hands to touch the shirt. It runs itself. And I was like, so I basically would just be doing SEO full time if I owned this con said content site.

And he was like, Well, I guess that’s one way of looking at it. And I was like, So you’re not gonna buy it? And he’s like, No, you should buy it. And I was like, Okay. So, I bought it. I paid 50 grand for it. I made my money back in 10 months. And that started me on the portfolio train. I was really interested in buying.

And so I was on the buying side 26 times. And my transactions got much larger. Uh, they never got that large content. Even back when I was buying, you know, in 2012, 2013, 2014. There wasn’t a lot of really large content sites. So, my largest ones were, were 500. I had two 500s, I had one 650. You know, so they were not huge in terms of the way that a lot of people would look at internet transactions.

But at the time and content, those were pretty big. Yeah. And, um, and I exited from that portfolio in 2015. Uh, to private equity, actually a firm that was doing programmatic ads, uh, sort of a competitor to like Ad Thrive and Mediavine called Freestar. Um, and so, uh, sold to them, and they actually shut it down within no time and said, Hey, we need to focus on running programmatic ads.

That’s what we’re good at. And, uh, I started advising at QuietLight a year and a half later. And I’ve been, I’ve been at QuietLight now for… Six years, I’m a managing director of quiet light. I’ve closed 60 deals as an advisor here and actually really love the work that we do at quiet light day in and day out, uh, in terms of advising clients and help people exit their business.


Jared: have, uh, you have truly been on all the different sides as, I mean, to some degree, SEO is developed. I mean, we, we talk a lot in the podcast, especially like the news section about the development and the, the way, uh, uh, SEO has gone, but I mean, you’ve been building brands and businesses online for, for quite a while now, I guess.

As we get into today’s conversation, I feel like you’re quite the well rounded person when it comes to today’s topic and this idea of owning web or digital assets and, um, and the approach that, that someone should take, like, could you just kind of set the stage for us as we get into this conversation and again, using that background you have to help people understand where we’re going in today’s conversation.

Yeah, so 

Brad: I as a general rule would put myself in a little bit of a naysayer on Portfolio building I actually get calls Many times a year from people who say they’re running and operating a portfolio that they want to run and operate a portfolio, uh, seems to be something that a lot of people, uh, see some, it’s an aspiration that people have, I want to own a portfolio.

And I will tell you that as I look at portfolio ownership, um, I think there’s some pitfalls with the idea. And so I think that. It’s it’s not that i’m saying don’t do it But I am a little bit more on the side of you might want to think about some things before you go down That road or as you consider going down that road and see if any of these things are true for you So that’s that’s kind of how I would set the stage I’m, probably going to sound a little bit like i’m negative on the idea of a portfolio.

I do think That the right person, uh, can do it well, uh, or the right organization can do it well. But what I’ve found in working with entrepreneurs and kind of studying entrepreneurs is that it’s hard to find those people. And I will just go ahead and admit that I’m one of those people that I don’t think can do it well.

It’s not my cup of tea. And I’ve had to just kind of accept that and say like, hey, that’s just not what you’re best at. 

Jared: Let me, um, let me help us all out here to get our mind around it. And I’m going to almost create like a quadrant and I can’t create a quadrant because we’re doing a podcast. I’m going to verbally talk through a quadrant and I’m going to talk about, uh, I actually have a quadrant written down on my sheet here, but, um, but that’s, that’s beside the point.

Like let’s look at it from these, these four buckets really, if we could, and talk about the perks and the pitfalls from a high level, from your experience of each of them. There’s the, uh, solo preneur, the solo person who owns and operates one, for the sake of our conversation, one website. And they run that.

Then there’s the solo person who owns and operates. A portfolio of sites, two or more. Then there’s the person who gets a team together to help them with their one single website. Presumably to make it larger and achieve some scale. And then there’s the person who puts together a team to help them grow and manage.

A portfolio of websites. So we’ve almost got these four angles, right? You can kind of do it all by yourself and build one website by yourself or you can get others to come in and help you with that. Or then you can go the portfolio route whether you want to do it by yourself. And a lot of people listening will have maybe three or four sites that they’re building kind of side by side.

And then there’s that portfolio where you bring in a team. And we’ve kind of interviewed a few of those people where they have large teams. Like, maybe just… To give people some framework help people understand like perks pitfalls of each of them and maybe if there’s any buckets I missed that you’ve seen.

Brad: Yeah, I know I like the way that you’ve kind of broken that down So, you know, let’s start with the solopreneur You know, it’s it sounds pretty obvious But you know in life, there’s there’s never enough hours in the day so I would just kind of make the observation that like if you own one site and it’s going well and That’s what you do You don’t have a divided interest when it comes to your work everything that you think about the I call it the anvil on the chest, you know, if you’re a If you’re like me at all, you know, like I wake up every morning with an anvil on my chest and that is like all the things that I need to do.

Um, and so, you know, I started having that anvil pretty heavily in my twenties and you know, here I am. I’m, I’m actually kind of an old man of the web now. I’m 44 years old. And so a lot of times when I meet people, they’re younger than me now and I still have it. And I’m actually even, I’m at the point now where I’m actually thinking about the end of my career.

And thinking about, well, how do I kind of want a sunset? And so I would say that like, that anvil in the chest, as I’ve kind of seen it, is something that is kind of based on time. You don’t have tons of time in every day. Every day you kind of find yourself running into a shortage of time if you have a life like me.

Now, I’ve signed up for some things in my life that might make my life more hectic than other people. I’ve got five kids, you know, I’ve got, we homeschool, which that probably sounds like, Oh, well then you got all this flexibility. But I mean, I have humans running around this property all the time, needing things, doing things.

And so I look at it a little bit differently is like, those are responsibilities that I haven’t given to someone else to take care of. I’m, I’m part of the education, although my wife handles 99 percent of it, that 1 percent does require something. So when you think about the solopreneur and the focus, I just think that like on the surface.

The idea of being able to focus on one thing and grind on one thing is a powerful thing. And what I’ve found on the web is that those that are able to focus on one thing and get up every day and grind and live that life, end up having an inordinate amount of success. And the thing is, like you said, I’ve kind of been on a lot of sides of the transaction.

So I’ve been a seller, I’ve been a buyer, I’ve brokered 60 deals. Um, so, and I’ve had a lot of operating experience and there’s a really interesting thread between my most successful clients that I’ve had at Quiet Light. 100 percent of them were focused solely on one thing, running one thing. They were, they had the same kind of schedule.

These are guys that when you’re, when you’re operating at the level where you’re going to go sell something for 25 million, you are grinding on that thing for 15 years. In my experience, that’s what I saw, saw from. From working with clients that have those kinds of exits. They do it for 15 years. They get up every day with that sense of purpose.

They don’t spend all their time vacationing. They don’t spend all their time. You know, posting all their, what they’re doing. That’s so fun to Instagram. They’re working a lot. They don’t have as many of those posts because they’ve got a big business that they have to have. And they’re kind of a solo preneur.

They don’t, a lot of them don’t even have, especially the internet space. You see that they don’t have well developed out teams. There’s a lot put on that sort of CEO candidate. And so I’ve seen those people just. Over time, that, that grind of just going after it, not giving up, and like, I’m trying to test new things every day, every week, every month, every year, they end up having an inordinate amount of success, and that kind of leads to big numbers in terms of what their seller discretionary earnings are, what their revenues are, and ultimately what their exit looks like when they go to sell their business, or, we’re not, we’re not trying to pressure anybody to sell their business.

Like, if you want to, if you enjoy the business, you should keep the business. You know, if you like working in it and you feel like your growth prospects are good, keep it, run it, use it as a, as a cash cow for yourself or your family. So I would say like on that first quadrant, that’s the most straightforward of all the four quadrants that you painted.

That one first quadrant is hard to beat because it’s so simple. Now, I will tell you, it’s easy to say that, but a lot of people listen to your podcast are entrepreneurs. And entrepreneurs love to chase butterflies. Shiny object syndrome. 

Jared: Shiny objects, that’s right. We have a whole section on the weekly podcast, Spencer and I do, dedicated to it because it’s just, it’s, it’s hard to ignore.

So it’s, you gotta at least address the elephant in the 

Brad: room, right? It is, and I will tell you, so when I bought the design blog for only 50 grand, put 50 grand in, but made my money back in 10 months, the finance guy in me was like sounding all the alarms. He’s like, look what you’ve done. You’re able, you can create for yourself 100 percent returns in 10 months.

What’s the S& P 500 done? That’s what I was saying to myself. You know, I think I probably woke up on those days and thought, I wonder if I’m the smartest man that’s ever lived. Look how I did all these things. What I didn’t know at the time was, right. But what I didn’t know is that I was benefiting from the way that Google was operating.

I was actually, before Panda and Penguin rolled out, which if you’re listening to this and you don’t know what Panda and Penguin are, that’s because you’re not a dinosaur like me, but, you know, those were early algorithm changes that affected links and affected Google’s processing, like, literally like a trillion times more content today than they were having to deal with back then, but they were having trouble dealing with it back then, so they built these algorithms.

That fought against it and so I rode the wave up for a long time While they were trying to figure it out and a lot of times those updates they were doing were dialing my traffic up So I was thinking man, I must be so good. I must be so good at this SEO thing I must be so good at building the content And so but when you talk about shiny objects when I said I was a buyer 26 times That’s supposed to be a resume builder, but I will tell you that was my biggest pitfall I was addicted to buying.

I like to buy, and I would think about the one or two things that I knew I could change immediately and make a difference in the business. But I wasn’t thinking about the grind of like, but what about after that? What about after you do that, and now the content’s sitting out there, and you don’t have the strategic plan to make it the most up to date, the best content library Google’s ever seen for this topic, and I didn’t make those plans?

And so I was actually playing with fire and, you know, as you know, like if you sit on that stuff for long enough, Google’s going to start monkeying around with it. I don’t know if you want me to, if you’re like, Brad, you just spent 10 minutes on quadrant one. Like, are we going to run out of time before you even get to quadrant three?

I don’t have to spend as long as the others, but I want to say like. Quadrant one is a very straightforward thing. So I’m happy to break into some of those others, but I wanted to just kind of point that out and let you speak. 

Jared: What’s the biggest downfall to someone breaking out from one project from one site into bigger projects?

Because we’ve heard it, we’ve all heard it. Everyone here has heard like, don’t, you know, stay focused, like stay focused on one project and don’t spread yourself too thin. The lure though, of having, and I think there’s a lure also to diversifying, especially in this day and age. A lot of people listening are relying on Google traffic for the pri, the primary, uh, uh, uh, traffic medium.

And, you know, there’s a lot less rhyme or reason to what’s going on. And so having multiple websites or projects can kind of help, uh, mitigate risk in many, like, so these are kinda the things people are gonna be thinking. What, what, what’s the biggest risk out of all though of, of going after more than one project in your experience?

Brad: Yeah, I think I think the biggest risk is that especially with content because let me let me just say that it’s not just me I’m not the only person that was addicted to buying you guys talk at all about Amazon aggregators on the pod Have you spent much time on them? 

Jared: Yeah, just as a 

Brad: super brief, you know overview of that We had these buyers come to the table that had raised a bunch of money to buy Amazon businesses because the idea was hey These are all run the same So, we’ve got great economies of scale.

We could hire a small team to run lots of revenue. That was the whole premise. And so they came on the scene and said, We’re the best. All of them said the same thing to us. We’re the best. We’ve raised 100 million. We’ve raised 200 million. We’re the best buyers. Nobody has the team that we have. I heard it from dozens of them.

They go close deals. Where are we at today with that? Well, there probably are some that will make it. Here’s where we really are. All the biggest ones are pretty much gone. And some of them have filed for bankruptcy. Benitago filed for bankruptcy. Thrasio is looking to reorganize, which sounds like they’re filing for bankruptcy.

And so when you look at that situation, it’s like, okay, wait a second. These people told us they were the best. They bought 100 businesses. And what we learned is they were addicted to buying just like Brad. They didn’t want to operate the difficult pieces of it. And we had sellers that came to us and said, Hey, they, they let my product stock out.

I’m not gonna meet my earnout. They let, they didn’t buy the inventory, they didn’t follow or do the most basic things. So that’s the biggest pitfall is that you fall asleep on things. When you start to add things, there is a cost and it takes a special person to be able to manage. How can you operate at a high level, like when I think of a portfolio operator that’s operating at a high level, I think of like Elon Musk.

You know, like when you look at Elon, you’re like, okay, how’s he doing with Tesla? Well, if you look at the stock price today be like, well, I guess he’s not doing very good But that’s not the reality. The reality is he’s completely rethought the way cars work, you know, there’s no dealerships We don’t have land all over the country holding multi million dollars worth of vehicles as storage on the most expensive real estate in the world Instead you order it from your phone.

You charge it from your home. It’s faster. It accelerates. I mean, I’m not trying to do an advertisement for Tesla here. I’m saying Tesla is a very impressive company. And if you drive a Tesla, I have a feeling you probably won’t want to go back to a combustion engine. Because it’s a better product. Okay, but it’s not just that.

Elon’s taking satellites to space with Starlink. He’s transporting our astronauts for the government when they need to go to space. And it’s like, oh, so he’s operating at a high level over there. He was co founder of OpenAI. He was You see a guy that’s like, Oh, this is a guy that now I will give one thing that I’ll say, like, this is an advantage Elon has that Brad doesn’t have.

I can’t attract the talent that he can attract, but I still think it’s impressive that he can build a portfolio. But I think that we need to be thinking about these portfolio operators more in the vein of like, You got to be a special person then we do instead we think it’s just like oh It’s just a list of things you just do these things and everything’s fine I’ll just take care of my content But I would say this and I don’t know that everybody’s necessarily a content operator, but I I did a lot in content So that’s why I talk about a lot the standards for what is I’m doing all the things I need to do Is generally a list of things I heard on niche pursuits or other trends That i’m hearing in the industry that everybody that’s doing is doing I don’t think that’s the way to win long term.

I think that’s a way to get you into the above average category But if you want to be the best you have to be thinking about well, what can I do beyond that? What can I do that’s creative that no one’s doing with my content or with my product? That’s like, I’m actually trying to do something that I just, it’s not just something I saw from my mastermind or from my podcast, it’s things that I’m so into my industry that I kind of found it.

So one of the big pitfalls, you know, that I would say is like, we think that if we follow this list of things that we’re up to date and then when an update comes out like helpful content two or the core algorithm changes, I mean, we’ve had a lot of disruptions in search in the last few weeks, in the last few months.

And we have people that would be considered very good content operators telling us they’re getting dialed down pretty heavily. And so I think that it’s one of those things where I’m like, and I’ve had people tell me on the phone, I’m doing all the things I’m supposed to do and I’m thinking, well, I mean, you’re doing all the things that you think all the best people are doing.

But is that all the things that you need to be doing? Or is it because you have these four other things going on that you’re not able to dedicate the time and energy? To rethinking what you’re doing and do it. Well, I feel like that’s the biggest pitfall one pitfall for me I don’t know if anyone else relates to is I would buy things that I wasn’t passionate about Yep, so I would 

Jared: like the financial Gain or potential of it over the interest or passion of it.

Brad: Yeah, and that’s a tough one because I Think that like I the friend I mentioned that’s in the graphic vector space In his situation, he was a graphic designer by trade. He’s passionate about design. He’s passionate about the tools designers need, and that has fueled him for 15 years to build an unbelievable business.

And I think that when I looked at myself owning a portfolio of web design blogs, I was like, well, I don’t really care about web design. I care about search and I care about making money. That was like the things I would think in my mind. I was like, I like search. I’m really interested in search. I’m interested in making a buck, but I didn’t care about web design.

Well, does that affect what my content looks like in web design? It absolutely does. I can’t tell you whether this jQuery tutorial is good or bad. Because I don’t use jQuery, you know, I can’t tell you what whatever the whatever the example is I can’t tell you a lot of these things because I’m not an expert on the topic And so I think that it’s at least worth considering When you’re gonna get into a topic like do I think it’s important for me to become or be an expert on this topic?

I think that’s another pitfall. So you made 

Jared: you made mention of something earlier on ten minutes ago, maybe I want to, I want to circle back on it. I was recently a guest on a podcast and at the end of the podcast, they were like, Oh, you’re the host of the niche pursuits podcast. What’s that like? I was, we were kind of talking about it and they said, what’s the biggest insight that you’ve learned from your time hosting for several years?

And I thought, boy, I hadn’t, I haven’t gotten that question before. And I wish I would have had more time to think about this. But the first thing that came to mind that I shared and I, I, it’s funny because months later, I’m like, yeah, that is the most. It’s valuable insight I’ve taken and I get to interview people every week that are successful.

And by and large, almost every single one of them to a T I’ve been doing this almost three years is focused on one project. And you basically said the same thing just now about all the people whose businesses you’ve helped sell on quiet light, man, go into that because that’s, that was a bit shocking when they, they heard me say that on their podcast as a guest and I’m sure a lot of people listening right now to you saying that.

Feel a little agitated and maybe like give us some more insight into that. 

Brad: Yeah, it’s, uh, it’s definitely a trend. Um, and it won’t reduce the number of people who call me and say, Hey, I’ve got this portfolio and I need to get rid of these assets in it, or, Hey, I’m interested in buying a portfolio. Like it’s a very prominent topic, building a portfolio, buying a portfolio, owning a portfolio.

Um, they think it looks glamorous. And you know to your point about diversification just as a side tangent you want to diversify Go diversify in real estate or go diversify You know in the s& p 500 or whatever your flavor is of stock market, you know options But like, if you’re in the web, you’re riding a pretty risky train.

Don’t let yourself fall into the pitfall of thinking that because I got one that’s about peanut butter and jelly and I got another that’s about gardening, I’m diversified. You’re not. You are solely riding Google or however you’re getting your traffic. You’re riding a wave of a gigantic third party platform.

Um, but no, I do think, I think that what you said, it’s really interesting to me that you said that because um, You know, now I think you’re really smart, Jared, because I, I feel like I don’t find very many people that agree with me on this topic. I’m more 

Jared: impressed that I just thought of something on the fly, to be honest with you.

Brad: But, but no, it’s, I do think it’s just, it’s just part of the trap. I mean, it’s, you know, it’s like, um, people kind of do the opposite of what they should do in most instances. You know, um, I’m interested in cryptocurrency. When do people want to talk about buying cryptocurrency? Do they want to talk about buying cryptocurrency when Bitcoin’s down to 15, 000 and Sam Bankman Freed is, is going on trial, um, and we’re finding out that Celsius is bankrupt, and we’re finding out, is that when people want to buy Bitcoin?

Are they like, oh man, Bitcoin’s low, I want to buy, is that when they want to do it? You want to know when my friends that don’t care one bit about cryptocurrency want to buy cryptocurrency? When it’s up. When Bitcoin’s at 69, 000 a coin, that’s when they’re like, I think I’m ready to move in and buy some Bitcoin.

People tend to do the opposite in terms of their investing of their time and their capital of what they should do. And so if building a portfolio is something that’s really interesting and enamoring, then maybe the idea of doing something simple and grinding, I say grinding for a reason. I think grinding has a negative connotation.

Sometimes people are like, I’m grinding, and they send a positive emoji, or, or a little, you know, uh, gif to you, or whatever it is, and, and, and they kind of do it in that way. But when I think of grinding, I think that’s a term that entrepreneurs don’t want to hear. When I say get up and grind every day, I think they think, No, no, no, Brad, no, I’m not looking to grind, man.

I’m looking to have a portfolio. We want to have a wide variety of assets, and we want to have cash flows, We’re going to be diversified and all these things and I think, yeah, but is that, is that, is that a real thing for you? Is that something that you’re going to be able to achieve and how are you going to achieve it and how are you going to do it differently than just kind of following the status quo?

Because I would argue that you probably can’t even keep up with the status quo once you get very many assets. Even the large organizations, you know, I’ve, I’ve got listings right now at quiet light that are holding companies that are performing very well. So more like a holdco, not a, not an holdco. And they’re bringing me assets and saying, Hey, we don’t pay attention to these.

Let’s get rid of them. We, that’s part of our materials on this one particular listing. It’s… Hey, uh, we got these two brands. We bought them. They’re just too small. They’re too small for us to fiddle with. We never spent any time on them, and it’s not meaningful to us. The other thing I would say too, and, and I still kind of fall into this trap.

A couple of years ago, a friend of mine and I bought a domain name portfolio. Huge mistake. So, you know, it wasn’t like the biggest purchase ever. It’s like a 600, 000 purchase, and we split it, and it is like first name, last name. Domains, mostly. Prominent ones. Like, more common than your name, 

Jared: first name, last name.

You don’t have my name, so they can’t be that prominent. 

Brad: But, but we don’t have like Jared, we don’t have like Jared Smith, you know, in there. You know, I’m not trying to say that either. Um, and you know what was interesting about it? Is it’s like, two guys that had operated, two guys that had spent a lot of time on the web, and they’re like, oh, here’s this investment, and you know, hey.

It’s, it makes about 50 grand a year, you pay 600, you know, thousand for it. So you’re getting like this annuity of, you know, basically eight, 9 percent a year and you still are going to own this underlying asset because you’re only selling off a handful of domain names every year. Like this is for the rest of your life.

And we literally got like two months into it and we were like, why in the world did we buy this thing? Like we can’t do anything to increase the number of sales. For, you know, bradwhalen. com type domain names, like, we can’t really do, all we can do is just basically sit here and sell when people come to us, and so It just gives us another thing that we have to fiddle with and we have to just, you know, and so I think that becomes the problem.

Like I, um, I still get roped in. I still do the shiny objects. I’m trying not to, I’m trying super hard in the last two years. I’m trying so hard. Like I wake up every morning. I’m like, Brad, you know what you are? You are a sell side advisor. That’s what you’re gonna do today, Brad. It’s morning . Yeah. You’re gonna go in there and you’re gonna help some people sell their business.

That’s what you’re gonna do, and you’re not gonna go look for something to buy. You know? It’s, it’s therapy for me. And, and because I have found that like it’s, it’s not just the chasing butterflies, it’s also the size. The size of the deal starts to impact your, your thinking too. So when you get to a point where you, you’re in your career where you feel like you have some flexibility with what you can buy, like you can buy like a little bit larger size than you used to be able to all that kind of thing.

It’s very easy to do the chase and butterflies on the small scale. Like I used to own this domain military bases. com I bought it from Flippa back in 2012 on, you know, in like literally in 10 minutes, I saw it on there. I saw militarybase. com on there. It’s for 125, 000. I hit the, uh, messaged the guy. He had a buy it now of 150, 000.

I offered him 125, 000. He said, why don’t you go up to 150. I was like, no, no, I don’t want to pay 150. I’ll pay you 125 tomorrow if you can show me AdSense access, Google Analytics access. I’ll wire you the money directly. Transfer the hosting to me. We’ll do a one day deal. He says, deal. I buy it. I sell it for 250, 000 about two years later.

The guys that I bought it from operated it for many years and I was like, I think I missed that site and I emailed them. You guys have any interest in selling this? No, we don’t. It actually, the traffic dropped after he sold it to us and it’s taken us a lot of years to get our money back. Oh, I’m sorry to hear that.

So then I come back and say, well, let me know if you ever want to sell. And then they came to me and said, you want to buy it? So bought it with a buddy of mine, which was like, Hey, you want to split this thing with me? Never did one thing on it. A guy randomly came through and contacted us. It actually had gone up on traffic because Google had been friendly to it.

So the earnings were up. And so we made money on it, but we couldn’t get ourselves out of bed to do anything to it. And so like, when you talk about, you know, what do you do as an individual and how do you manage this? I think that the, that the other thing too is when you want to build a portfolio, you’re like whatever.

If you, if you’ve got a million dollars to spend or if you’ve got a hundred thousand dollars to spend, if you want the portfolio, you don’t want to go spend all of it on the one thing. So you go buy like with a portion, you buy something and you’re like, I’m going to divide. I think it would be way better to say I’m spending a million or I’m spending a hundred and you go all in and spend that amount and then you get up every day and you work and grind on that asset.

And see what you can make of it. 

Jared: Let’s talk to the person, I mean you probably haven’t talked to everyone out of being a portfolio 

Brad: owner. No, I try, I actually try not to talk to anyone out of it unless they ask me. 

Jared: Well, we kind of asked you. At least to come on in. And we’ll say Play Devil’s Advocate, right?

Because a lot of people, we’ve had people on that are building portfolios that have measured approaches to that. And some that have a financing approach to that. But, you know, we like to kind of bring all sides of the conversation. And, and so following that vein, like for someone whose ears are perked up, perhaps they have one too many projects or maybe more, but one too many.

Um, I think that we’ve, we’ve talked about a couple of times, like there’s this desire to have a shiny object or as entrepreneurs and as creators, we do get excited by possibilities elsewhere. And that oftentimes is the reason why when we get out of bed in the morning, we’re not as focused like you described.

Do you have any tips, whether from your own experience, because it sounds like you’re really going through it right now, or just from what you’ve seen be successful for people, like tips to scratch that itch without starting new projects, tips to feed that side of all of us without derailing our focus and our efforts to grow a single project?

Brad: I think for me, what has helped me is that I’ve realized that the results are not better by going out and getting more. I have this perception in my mind that the results will be better. When I’ve reflected on my portfolio, which was all web design sites, I’ve thought many times about how that first site cost 50 grand and then I went on to spend more and more money in it.

That became more and more risk for me as I went on, but I’ve many times reflected and thought instead of buying all those brands. If I had just taken that one 50, 000 investment and just poured all the energy and stuff that I put into all those other 25 and just kept going after it and I think about all the things I did, I launched marketplaces that had memberships, I launched, uh, different types of affiliate partnerships, I launched training programs for how to learn different types of web design and development, um, Um, did all these different things in that portfolio and I think if I instead had just launched all those things on this one domain that I had bought, I think I would have had the same revenues or greater.

I would have built a bigger brand. I would have had the same revenues or greater at a fraction of the cost, at a fraction of the stress. And my exit would have probably been much more glamorous when I went to sell it. So when I look at it, I think that like part of that conscious, Brad gets up every morning and says to himself, today you’re going to go advise clients because that’s what you’re doing.

That is a positive message in life because I think I’ve come to the realization, like I wish I was like the guy that just could like see the angles without experiencing it. But in my operating career, that’s not been me. I’ve been pretty good at finding things that can make money. I’ve been pretty good at not getting myself burned.

Uh, in terms of like, buying something so stupid that you just lose all your money overnight kind of thing. Um, but I, but I have not been good at not having to learn the mistakes. Like, most of my advice comes from experience. When a, when a seller comes to me and says, Hey, we’ve got this platform. It’s been ranking for 15 years.

It’s legacy, but we’re building it all over in a new tech. And I’m like, do you rely on search? Do you rely on this? Do you rely on that? Yes. This is a very risky move. You don’t know what you don’t know. Can it be done? Sure. It can be done. It takes a special person to migrate and do a find and replace for all your tech stack that has brought you all your business.

Like, don’t go into this thinking it’s better because it’s new. Because that old tech stack might have some value. Now, there might be people that listen to this. I mean, look, if, uh, if Syed Balki listens to this, he’ll be like, Brad’s clueless. I’ve got awesome motive. Look at what I’ve built. I’ve built an empire and I’d be like, you know what?

I said for your average person or for your regular listener, this is not gonna work. I, there are special people. It takes a special person. Syed’s a special person. He’s a guy that’s proven that he can do it over and over again from everything I’ve seen, you know, he’s, he’s built so many things. He’s acquired, he’s partnered, he’s done all sorts of things and he’s had, got this track record that kind of proves it.

And so. You know, I really feel like the evidence is kind of in the sort of the 99 percent rule here of just like, look, if you just want to just zoom out, just think about it. You know? I mean, if you woke up tomorrow and your only goal was, I’m going to be the fittest person I can be. And so I’m going to spend eight hours a day working on my fitness.

And then you said to yourself, I’m going to wake up and I’m going to work on fitness, but I’m also going to work on reading books and I want to try to read a book a day. And then you wake up and you say, I want to do the fitness and I want to do the book a day and I want to learn how to code. Like, it’s very easy for us to see, well, Brad, very quickly, you’re not going to be able to do all these.

You need time to be as fit as you can be. If you want to learn how to be a programmer, you’re going to have to do a lot of trial and error. You’re 44 years old, it’s going to take a lot, you don’t know anything about programming. If you want to read a book a day, you’re going to need several hours for that.

But when it comes to business, it’s like, I don’t know, if you’re a good leader, you can just put the team in place and you’ll be good to go. Well, maybe. Maybe. But what happens when that Google Helpful Content 2 comes out, and you see 40 percent drops across a 30 year portfolio? What do we do then? Do you have the team in place to sound the alarms and go try to figure out how you’re going to navigate it?

And fix all those problems. I think that’s where it becomes a challenge. It’s like when everything’s going perfect When I was riding high when I was buying And they had not rolled out a lot of their iterations on panda and penguin. All I was seeing was Everything I do goes up and makes me more money So I must be the most brilliant creator and I got to be humbled in the most glamorous way when they started Kind of tinkering with the traffic and I realized like whoa now I’ve got 26 problems and I’ve got to figure out how to navigate it and I was very fortunate for the way that that kind of turned out for me because My revenue stayed steady even against my traffic going down for a long period of time which allowed me To navigate it and figure out this may not be the best business for me And eventually to, to actually sell and divest out as we 

Jared: kind of start to wrap up.

Let me, let me ask you this. What, what sort of analysis can someone do to determine if they are, you know, kind of that unique Elon Musk of, of, uh, of, of the analogy you gave, like, because like you said, there’s, there’s probably a collection of people, a handful of people listening, just do the sheer numbers of, of the people that listen that might have the, the, the nows to run a portfolio, you know, like, But you don’t want to get so far in before you realize whether you do or don’t.

And maybe that is the only way, but are there any other things you’ve seen from the handful of people that you’ve found that could be successful? Maybe some questions that people could ask or some things they could look at about themselves to see if they might be that type? I 

Brad: think if it’s reliant on one person, it’s going to be pretty difficult to convince me that you can do this successfully and just continue to add properties.

There literally is only so many hours in the day to work on things. You can’t work hard enough to manage something when it gets big enough, when it gets large enough. Um, I think if you find that you are particularly good at attracting talented people to work with you, people like to work with you, people are drawn to you.

You feel like you have people that are smarter than you on the team. Um, that, that’s a big factor for seeing that kind of growth. Um, I think that your best entrepreneurs are generally, in terms of scaling, are generally ones that say, I hire people that are better than me at different things to come in and do things.

So, if you find yourself in a spot, I mean, even if you can find one person. That you think they’re loyal to you. That you can afford to compensate. That you think does it better than you can. And can understand your vision and your goals. And they don’t have any desire to betray you. Or to move on from you.

And things like that. Like even one person that can do those things. Probably gives you the ability. to take on more than one thing. But I do think that a lot of entrepreneurs don’t love the nitty gritty of that kind of work. A lot of us don’t love to sit down and have the meetings. When I was in more of my, what I would call my corporate career, my custom t shirt business was not really corporate career, but it was the most corporate I ever really got to outside of the short stint at camping world.

When I was in that career, I was known for not liking to meet because it was exhausting to me. I, I would walk into a meeting with a bad attitude in my head of like, why are we here? What is the point of this? We’ve got 10 people here. I’m running numbers on how much we’re paying for the meeting. You know, I would sit there and think like, well, we just spent 20 minutes talking about the last holiday party and there’s 10 people in here.

So that was an expensive conversation. Like, I, I have an analytical mind, like that’s where I would go to. And so I think that you’ve got to be a person that is going to be honest with yourself about do you, if you want a portfolio, do you want the things that are really necessary to operate at the highest level?

Because I don’t think operating at the highest level is just doing what the best guests that come on Niche Pursuits are doing. Even though I’m very impressed with the people you bring on and the things that they’re doing. I don’t think that that is the standard for, you know, what is good. What is good has got to go beyond just what other people are doing.

Like, we don’t have to reinvent the wheel, but we do need to go in and be able to think outside the box. About ways to maybe improve the business that not everyone’s talking about and be able to test those ideas 

Jared: It’s just interesting the timing a lot of people that I’ve talked to about Helpful content update have said hey, I just think now it’s gonna take more time for me to make my website The best it can possibly be right like I just need to be doing more things whether that’s also Uh, building social media channel, uh, accounts and building social media followings, whether it’s, um, building, uh, products to sell so that, uh, the website has more of a brand aspect to it, whether, and in many ways, these are all things we should have been doing anyways, right?

Uh, going back to your point of imagine if you just kept that first 50, 000 purchase and just done all the things to it now. So, perhaps in many ways, and again, The helpful content update was decimating. So I’m not trying to say this as a silver lining, but perhaps in many ways, a lot of what you’re talking about is a lot of what we are learning the hard way for some of us, at least through that helpful content update.

Brad: I think it definitely is. And like, look, I’ve talked to a lot of people and I’m not trying to get into like our theories on what’s going on in SEO, but I’ve had so many people try to look at, let’s just talk about AI. Okay. People try to look at AI in such it’s like its own bucket over here. Like, if you talk to people in the food content space, a lot of them will be like, Well, AI is not affecting us.

And is that because AI doesn’t create pictures of the recipes, and it can’t do a flavor profile of what’s gonna taste good to it, you know? Like, I don’t know exactly what the reason is there, but I think to myself, Well, actually, let’s just say Google was being fed a billion pages a day before this AI, you know, these, these, these libraries of content started being used to create content.

And after they launch it, they’re being fed four billion a day. Well, we’re all in competition. No one’s immune. I’ve said to people about helpful content, I’ve said, Hey, I think this could be related to the amount of content coming from AI. And people have said to me, Oh, you must not understand helpful content.

I’m like, well, no, but I understand economics. In economics, you know, there’s an economy there in Google. If Google’s used to seeing a billion pages a day, and we start feeding it four billion pages a day, then there is not enough room for all four billion of those pages to rank where people would expect them to rank.

And there’s gonna be collateral damage, because a lot of times, here’s how I feel, here’s how I like to describe the updates, Google does this. They turn the dial and then they look and they’re like, let’s see what happened here. And sometimes if you own sites, you probably, if you’ve been affected by updates, I bet you’ve seen an update before where you went down and then some time passed and there was a moment where it just went back up and you never changed anything.

And it’s clear that they had a volume dial on your traffic. They weren’t thinking about you. They were thinking about something completely different. And they turn that dial and then they looked at the data and then they came back and said, Hmm, don’t know if that results is good. And they turned it back some of the way.

And you started to see different change, even though you made no changes. And so, you know, I do think that, you know, the timing, this has been one of the most dramatic years for Google Updates that I remember in a while. And so it is painful to kind of go through that and, and I don’t think it’s always as simple as saying, Hey, if maybe if you just had one website, you wouldn’t have, you wouldn’t have suffered that fate.

Um, because I think we all have to remember that if you live in a world where you’re reliant on a third party for your livelihood, then you have to know that you’re reliant on that third party. Which means that they might make decisions that are in their best interest and their best interest may not be your best interest.

And that is where we are on the internet. If you operate on Amazon, you’re operating in a world where Amazon operates in their best interest. If you’re in content, you’re operating in a world where Google operates in their best interest. If you’re on Facebook running ads, You’re in a world where meta operates in their best interest.

It is very difficult on the web to find yourself in a spot where you’re not tied to gigantic parties that have different goals than you do. And so, that’s where the volatility is. That’s why we all live very far down the risk curve. We’re out there, you know. I don’t know if we’re at like the, you know, degenerate gambler, you know, level, but we’re somewhere down the curve.

Well, I think 

Jared: a lot of people might. Uh, say that it’s felt a lot like gambling over the past couple months given all the ups and downs from, uh, from, from the various Google updates. I think that might be an apropos statement. You know, 

Brad: one other thing I would say, Jerry. Go ahead. No, go ahead. One other thing I would say is it’s just interesting because I’ve had sellers even that don’t have that, you know, they grind and they go to the 25 million sale.

I’ve had people that I’ve worked with where I just see an intentionality. To what they do that would be impossible for them to do that across multiple entities in my opinion I’ve got a seller right now. That’s 68 years old And he’s looking to retire and I’ve just been so impressed with him because he got the COVID bump.

So we call the COVID bump. This goes up, comes down. It’s a bump. Um, we’re dealing with a lot of COVID bump businesses right now, but his went like this. It bumped and then it went and I was like, Hey, what’s going on there? And he’s like, well, I noticed that there was this COVID increase going on. And I thought this COVID thing is not going to be around for very long.

We got to start making investments right now so that we can keep this going. We don’t want to go down once we go up. And so listening to what he had done, he invested in, in Klaviyo and doing a very good implementation with Klaviyo and, and getting that set up and spent a lot of money getting it. And now he’s got these emails that get fantastic results every week.

He launched his own private label brand when he was selling other people’s brands. He launched his own private label brand where he’s focusing on all the things that his customers have said are the most valuable to them over the years. He has, uh, gone in and made multiple improvements to, like, speed and all these different things.

He had, like, seven or eight things that he did, investments that he made, and every single one of them has benefited the business. And I’m just like, look at that intentionality. Like, you can see why I get into the spot where I’m like, for most of us, it’s probably better to just work on one thing and work really hard.

Because that’s, you know, kind of the way it is. You know, I read a book many, many years ago, uh, by Benjamin Graham called The Intelligent Investor. And, you know, he says in there, way before indexing, I know everybody now like owning Fidelity or owning Vanguard, like everybody thinks like, Oh yeah, that’s, and people own index funds, index funds rule of the day, 20 years ago, there was a big debate about whether passive management or active management was the best way to go with investing.

Benjamin Graham, close to a hundred years ago said, if you are an average investor, it probably will be best for you to just hold the entire market. You’ll get the best returns if you just try to hold the whole market. And don’t try to get into the business of trading. And I think, I think one thing to ask ourselves, am I average?

Am I above average? Where am I at on this scale? If you’re getting into the internet world and you think, you know, if I’m really honest with myself, I may be a little bit above average if I’m above average, I probably need to be careful about how risky I get with how many investments I take on and how many things I focus on at once.

Jared: Well, it’s a good way to bring us to a close here. I mean, and again, just for everyone listening, like. Yeah, it’s, uh, it’s a debate not to be taken lightly, right? It’s pretty easy to just kind of quickly lean into a, uh, uh, a squirrel, uh, uh, uh, what Squirrel moments, right? Like a squirrel, you know, uh, a side hustle that, that you then kind of turn into four.

And, and not that that’s bad, but I think this, you know, the, the greater purpose of this whole conversation is, is to try to find a way to maximize your efforts and what you’re doing. From a time and an ROI standpoint. So, um, uh, Brad, where can people follow along with what you’re doing and catch up? I mean, you’re with quiet light, so I mean, you know, I’m sure they can, they can catch up with you there.

But where’s, where’s the best place to, uh, to direct people? 

Brad: Yeah. Brad at quiet light. com. I’m Brad Whalen on Twitter. I’m on LinkedIn. So, uh, happy to talk, you know, at quiet light, we do, uh, give free advice. So, you know, if you ever want a valuation for your business, if you ever have a friend that’s looking to sell, we do pay referral fees.

So. Uh, certainly, uh, you’re welcome to reach out Brad at quietlight. com and ask me any questions or anything. I’d be happy to give you my advice and it’s free so, you know, you can take it for 

Jared: what it’s worth. I just used that. I just said that the other day in the podcast. It’s fair enough, you know, these things, uh, uh, thanks for joining us, Brad.

I’ve, I’ve really enjoyed the conversation. I’ve struggled with a lot of the things we’ve talked about. I feel like a lot of people listening will have, um, are in the middle of this somewhere and certainly can lean into a lot of the feelings that, uh, that we talked through. So I appreciate you coming on and sharing your, your decades long experience with all of this.

Brad: Thanks a lot for the invitation. I really appreciate it.

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