How This SEO Specialist Sold Three 6-7 Figure Businesses to Google and Semrush 

Wouldn’t it be nice to use SEO to grow businesses to 6-7-figure exits within just a year or two?

That’s what our latest guest on the Niche Pursuits podcast does.

His name is Dmitry Dragilev, and over the years, he’s refined a repeatable process he’s used to sell an app, SaaS, and affiliate site to companies like Google and Semrush.

To accomplish this, Dmitry stresses the significance of employing a well-thought-out exit plan and a consistent approach to business growth – particularly through SEO strategies – keyword research, and backlinking techniques.

Dmitry candidly discusses his SEO mistakes over the years, such as targeting incorrect keywords and underestimating the ongoing efforts required to rank high in Google.

He shares some good general advice, like starting with low-volume keywords and gradually progressing to more competitive ones. And emphasizes the importance of niche authority and recommends steering clear of broad topics for enhanced SEO outcomes.

A particularly interesting insight is how he looks for weaknesses in the SERPs – thin pages and those lacking any helpful content for the desired search term.

Drawing from his experience of selling businesses to major companies, he underscores the importance of fostering connections and relationships in achieving business success. And some of the value propositions online businesses should target for better sales terms.

Dmitry also provides valuable insights on pitfalls to avoid when building a business.

Overall, this is a discussion on good practices for SEO and even business more generally. And it’s certainly interesting to hear from someone who has experience like his!

Watch The Interview

Topics Dmitry Dragilev Covers

  • Growing businesses with the intention to sell fast
  • Selling to Google and Semrush
  • The same process and approach he’s used
  • Keyword research tips
  • Finding thin content in search
  • Assessing the potential of zero search terms
  • Reciprocity
  • Acquiring sites
  • A fun story with Gary Vee
  • Tips for attracting higher multiples on your sales
  • And more!

Links & Resources


Jared: All right. Welcome back to the niche pursuits podcast. My name is Jared Bauman. And today we are joined by Dimitri Dragalev. Welcome Dimitri. Thanks for 

Dmitri: coming on board. Thanks for having me. Thanks for having me. Great to be 

Jared: here. Yeah, it’s good to be here. We, um, we worked through a couple of technical issues on the, on the front side, so I think We’re good to go now.

And, um, and, uh, I, I, today’s conversation is really fun. I’m going to, I’m going to let everyone, I’m going to let the cat out of the bag. We’re talking a lot about acquisition and a lot about your history in doing that. You’ve got not one, not two, but three or maybe even more that I don’t even know about that you’re going to be kind of dancing around the day.

But before we get into, you know, the details of the podcast, can you give us some background on yourself and, uh, catch us up to the conversation we’re going to have today, and, 

Dmitri: Yeah, I’m an online entrepreneur just like most of you guys listening to this met Spencer at rhodium Basically buy and sell sites and scale them with and sometimes I build them from the scratch But the idea is just like all of you guys love dabbling with online businesses And I’ve been lucky enough to you know, build three businesses and get them acquired and develop a methodology for it.

And um Yeah, I just keep doing it over and over now. 

Jared: I think I was going to say, once you have a good process, why, why change it? But I think that’s actually a lot of what maybe we’ll talk about today. Um, can you give like, maybe just give an overview or a history of the. Um, businesses you’ve started, sold, acquired, sold, et cetera.

Um, you don’t need to go into any details, but we always, it’s good to give people like a frame of reference for each of these things, and then we’ll get into the approaches you take and you took and how you, how you actually, um, how you actually did it. 

Dmitri: Yeah, they’re all a little bit different. The first one was in 2014.

This was um, I was one of the three people who started when we started the business who worked on it Um, the business was sold to google. I chose not to join google So I always turn myself as an outside consultant at the business. I’m not a founding member but um I was one of the three people main folks that were Building the business.

Um, and yeah, we use PR and SEO. It was a polling app that allowed you to find and make these cool little polls. And it’ll be a visual poll for people to include in their articles. Um, pulling anything from what kind of coffee you like to popular celebrities to what would you buy in terms of assets. And we grew really fast to 40 million page views were bought by Google.

Um, that was my first one. Um, then I found the Just Reach Out, which is a platform for you to pitch journalists. It’s a software platform, and do it all on your own without PR firms. Um, and, um, ran that for six years, got that acquired. Right as COVID hit. And then after that, um, founded a blog because I was hanging out with so many, uh, Spencer’s friends, uh, rhodium crew who were buying, selling affiliate sites.

Um, I bought a domain and scaled that in about three years, two years, and sold that to SCM rush. It was a, it’s called smallbiz. tools, it was a affiliate site for small business tools. And that was my third one. And now I’m working on a company that is not yet acquired, but I’m already toying with some, some ways of getting that acquired.

Um, but it’s only been a year or so. But yeah, those are like quick little overviews. 

Jared: Well, I mean, obviously track record of grow, uh, building, growing, selling, building, growing, selling. Did you start all of those from scratch? Did at any point, have you acquired one of those projects and then built it and grew it?

Or were they all from the ground up that you be, that you began? Um, 

Dmitri: small biz tools was an existing website. It did not get much traffic. Um, the design was really bad, of course, but it wasn’t an affiliate site when I bought it. Um, that was the only one out of the three, the others are from scratch. Yeah.

Jared: Well, I mean, obviously you have an approach that, um, works. I guess I’d be curious from the outset before we dive into some of these details, like, Is this something where you’re following a very well defined process, obviously adapting it specifically to the business use case, or is it a little bit more, I happen to have sold three companies, but I’ve done it three different ways.

Dmitri: Um, I think to grow it, I followed the same approach for all three businesses, even though they were so different. One was an app, which had a web presence, another one was a software platform, which is mainly used on the web, and the other one was an affiliate blog site. All three I grew through SEO, through organic search, and through my methodology of keyword research and backlinks.

Um, just, and I built a whole team of people who kind of are contractors and people who work with me. To build links and to do keyword research and to grow. I also, when I started the businesses had ideas of who I might sell to when the time comes, so I was very diligent and I knew kind of what the exit plan is with each business idea.

So. Um, I didn’t know exactly how it will play out. I didn’t know what the conditions would be, of course, but I was planning for it. It was like a five year stint, three year stint, you know, like I, there’s, you know, some people just want to grow a business for a really long time and be there for 10 and 15 and 20 years and make it.

I’m, I get more of a kick and pleasure and excitement when I’m just getting it going, getting it to one level, like say 10, 000 or whatever, 5, 000 customers and then just, you know, let’s sell it, you know, get it to a million bucks in a year and then just sell it, get it to 500, 000 a year. Sell it, that kind of thing, you know, versus like, let’s go for this for the sky.

Jared: Let me ask you, because you know, a lot of people listening and you even represent yourself, like a lot of people, when they think of selling something, they’re going to think of selling their website and maybe it’s a content website. Maybe it’s an affiliate website, maybe it’s a site in that vein, right?

You’re, you seem to have more of what I would call tools. Um, and, and correct me if I’m wrong there, but you know, you have a polling software. You have a reaching out like a journalist type of agency. And then you had a small biz dot tools, which I can only assume is tools or a tool type of site. I mean, is there much different from growing those compared to more of a standard content site?

And the reason I feel like I can ask you that is because you are around those types of people. 

Dmitri: Yes. So the last one was actually a blog. Small Biz. tools was completely an affiliate blog site. We didn’t have any actual tools in there. All we did is we just review business tools. So that one was, um, just a blog site.

The first two, yeah, they were apps. And so the process to grow them was a little bit different, but I’d say SEO traffic was the same. It was just. Content links, and that type of activity, you know, keyword research. 

Jared: Well, let’s get into it. Let’s talk about how you grew these. Cause that makes it even more interesting.

Like you’ve grown software, you’ve grown blog, you’ve, you keep growing these things and you keep selling these things. And those topics are extremely interesting to people, especially as you go into a new year here. Um, I mean, from a high level, can you share some of the different strategies that you’re using?

In your, um, in your SEO approach. 

Dmitri: Yes. Um, I actually brought a little cheat sheet to show just so you’re not people who are viewing this are not just looking at my head, but, um, an actual. Uh, quick little, um, worksheet. And so, in the worksheet, when I think of ranking on Google, right, the first thing I think about when I think keyword research is, you know, have I written about this topic a lot before?

And what is my MozDA, or what is my SEMrush authority ranking? Moz is a little bit dated now, um, but I, I start to think, okay, if I want to rank for, let’s say Asana versus Notion, or let’s just pick a random keyword that we want to rank for, right? Is my site primed around project management tools? Have I written about it?

If I have not, usually. It’s not I shouldn’t be writing about it right off the bat. I should be writing about something very very long tail so Um, I might go and look at asana alternatives for 2024 or something like that It gets like maybe 10 searches a month. Um, and so I um, I really dialed in And build up that topical depth in that topic and then I will start writing for longer bigger You Volume keywords.

Um, so that’s the first part where it’s like, my website has topical depth authority on this topic. Yes. No. I have written six articles on this topic in the last three months. Have I written six articles on this topic on project management? Yes. No. I regularly post about this topic in my newsletter and my MozDA is, um, around the same and I’m I’m using MozDA.

A lot of us are probably going to be using Ahrefs now or SEMrush, right? For authority score. But I, if I want to rank for this keyword, my SEMrush score probably should be around the same as what the other ones are or Ahrefs, right? And then afterwards, I’d like to really dive deeper into weaknesses in the search.

So like finding problems, searches that actually have problems, like, is there thin content on the search? Like old, thin content, meaning 800 words, a thousand words, maybe less than a thousand words, 500 words. Is there old content, less than six months ago? Like. Stuff that’s been, uh, published six months ago, or maybe there’s forums ranking on the, on the search, right?

Like Reddit, Twitter, Facebook, right? All these different weaknesses in the search, and sometimes it’s the page loads really slow, right? Google PageSpeed Insights mobile score is really low. Um, so these are all problems that we see on SERPs. And when I think about ranking on Google, this is what I sort of think about.

Like, what is, what are these weaknesses and problems? That I can capitalize on. And if I spot a SERP where, Hey, I’ve been writing on this topic for a while, And hey, I, I, uh, you know, I find these problem areas, That’s where I attack and I say, Alright, I get my writers writing on that topic, I get my link builders building links to that topic, The trick is just, you know, you got to spot these things and you need to have a team of people, you know, dedicated to this approach.

Uh, but it’s not, I mean, I, we’ve, I’ve taught many people how to do this. Um, I have a, a coaching platform where I just. I coach people how to do this kind of keyword research and, um, most people who’ve never done this, you can even learn some of this stuff. Um, but I’ve used this process to grow the small biz tools blog to about, you know, 20, 000, 30, 000 uniques from nothing.

Per month, um, in those two years, um, you know, we’ve grown just reach out to close to 5, 000 customers through PR and other initiatives. But every day we get, you know, 10 to 20 signups at just reach out just from this activity, just from ranking for how to write press release, how to do that kind of stuff.

And same with Polar. Polar, we picked keywords that were very buzzy in terms of news. And created polls around them to try and rank. So it has helped me over time, you know, since 2014 through 2024. 

Jared: Where are you finding these types of keywords? I mean, you know, you, you mentioned, uh, I wrote it down a sauna versus notion.

You talked about the project management bucket in your example. Um, are you looking for keywords under the bucket of project management or are you kind of drilling deeper and going, no, I’m going to focus on a sauna specifically, and then look for keywords around maybe a sub of project management. 

Dmitri: It’s a good question.

So the first thing I think about, and I tell it to all our students at PR that converts the platform where I coach people is what is. going to make a transaction for you? What kind of search is going to help you earn more money? Whether you’re running a content site, which maybe most listeners are running content websites.

Maybe people are running software websites or tools, but what is it that’s going to help you get more revenue out of your content website? Which searches would those be? And that’s where I start my, I guess, ideation or thinking. Um, you know, like if you run a travel website, which might be a lot of listeners, you know, some of them are familiar or running them, you know, it, it’s what type of searches within travel earn you the most money?

Is it like wedding venues? Is it sandals resorts? Is it the type of like specific destination like Puerto Rico vacations? And from there, I will start looking into subtopics of that, like saying, Hey, have you covered this topic? If you haven’t done too much, let’s dig deeper into that. Like Puerto Rico vacations for families of four in 2024.

Now, the volume of that search is going to be much less 140 or a hundred, and that’s where you wanna start with this process. You don’t want to start with a search volume of. For example, 100, 000, 3, 000, 5, 000, these are high competitive searches when you get into thousands. So, anybody who’s trying this methodology, I was like, needs to pick a keyword that’s got 100, 200, or 300 searches that you can go after.

And it’s not that it’s only going to get 300 searches a month, there’s so many versions of that word that you’ll probably get a higher volume. It’s just to start off, you want to start with something around there. So yeah, I think about like who’s going to convert. 

Jared: We’re, um, maybe flipping the script there a bit.

What are the biggest mistakes that you see people making when it comes to keyword research or maybe that you’ve made along the way, um, uh, in terms of whether it’s a certain tactic or whether it’s something that looked really good on paper, but didn’t play out in terms of, uh, it’s ranking. Or, I mean, even maybe something that, uh, a keyword research tactic that led to a lot of traffic, but never really ended up converting 

Dmitri: for you.

Yeah, I’ve done my fair bit. Um, a lot of times I actually have picked the wrong keyword where I got the volume, but I didn’t get the conversion. So a great example is my blog, my personal site. criminallyprolific. com that’s my SEO consulting work and so in 2013 and 14 15 I was trying to build traffic to the site I was about to launch or start thinking about my PR software and I decided that writing about cold emails Is going to be the best in terms of opportunity because not a lot of people were writing about cold emails But they were sending a lot of them.

It was still sort of growth hacking days. People were talking a lot about growth hacking 2014 There was a Growth Hacking Academy, Sean was running it. So I wrote a lot of these articles, like a ton. And I ranked number one for the word cold email. I ranked all sorts of topics around templates, and when to send it, and open rates.

And it was great. It was great traffic. The problem was that most people that were sending cold emails, they were doing that for sales purposes, to sell something to someone else. It was not for PR activity. Like, PR activity, yes, people do send cold emails for PR activity. But the majority of people, when they look up cold email, they’re looking it up to sell something to someone else, not to send a PR email.

If they’re sending a PR email, they’re going to look up, The best pitch template for whatever not knowing that I invested lots of effort and time because me I thought this makes sense. This makes a hundred percent sense like we had a meeting with our team But being the founder people just gravitate to what you think, you know, people don’t challenge you as much And I wish somebody said something strong, like contradicted me stronger back then, you know, people did tell me like, hey, cold email could mean a lot of things.

I was like, no, I want to be number one, you know? And so, so anyway, um, that was just one. A lot of times also. You just underestimate when you do rank for it or start ranking that you’re all set It’s like the game is just beginning because like there’s somebody’s gonna outdo you in six months if it’s a competitive term You know like so you got to keep your game on you got to keep updating the content and you got to keep Linking building.

It’s like it’s just starting there. It’s not that you’ve reached number one. You’re done. It’s like, okay now we start like cuz it And you have to keep updating the stuff. I, I’ve lost so many positions, um, just by like being like, all right, number one, I’m going to go next keyword. I’m going to go with the next keyword.

Um, and then the third mistake I’ve always made is eyes on the prize. Like everybody wants to go after the toughest keyword, biggest volume. Nobody wants to be doing like 10 mile, 10 a month, 15 month volume keywords. And. Busting their butt trying to get ranking for that. Everybody wants to be trying to rank for 10, 000 a month search keyword.

The problem is that it takes a really long time and you get upset and, and you hire or fire people and you get down on yourself and it, it becomes this whole thing, this like emotional, weird, psychological thing. And I always now say, it’s like, listen, pick two really easy ones. I don’t care if it’s like zero months.

If it’s like relevant to you, pick them and then pick like a hard one as well. And a lot of times, like people look at it and it says zero months and we’re like, well, what would it be in five months or six months? Maybe people are just not searching for it now, but maybe people will in the future. It’s like building a business, you know?

So a lot of times. I think of search volumes is, you know, something that you’re betting against for the future. You know, 

Jared: you talked about how important competition is, whether it’s DA, DR, SEMrush metrics, majestic metrics, whatever you’re using to value. How strong your other domains that you’re competing against are.

Well, like, I mean, how do people get around that? Like to some degree, uh, everyone’s going to run into a problem where they find a keyword that feels topically relevant to their site, but then they look in the competition is that domains with a much higher ranking are, um, are ranking higher in them, right?

What do you recommend doing that situation, especially for people, you know, with a brand new blog, like to your point, you know, you started, um, small biz. tools, uh, in 2020, I think you said it didn’t have much strength up against his competitors. How do you go about that? How did you handle that? 

Dmitri: Yeah. Good question.

I mean, very typical. That’s why on the spreadsheet, uh, on the worksheet here, I, I said, is my domain ranking close to the first page of Google results. So that’s like one of my qualifiers when I start working on this stuff is like, how close am I, right? If I’m 40 and everything there is 80 plus, I’m going to forget about it for a while.

Like I’m just going to forget about this keyword and go find something else where I’m 50, I’m seeing 50s on there. I’m seeing 30s. And I’m 40, right? Because I want to be in good company. It means, like, but the other thing that I look at and you brought up topical depth is who is ranking up there? Do these domains have topical depth in this topic?

So if I’m writing about best mattresses, and one of my students has a site all about Reviewing mattresses, um, and I say best mattress for 2024 and I have market watch and Barron’s Ranking number one number two, and then I have a bunch of other CNBC and whatnot trying to rank really high I know that these sites are not mattress websites, right?

These are just really high domain authority sites that have recently covered this topic. And I know that with time, they might not be on it in terms of updating those posts, right? And I know that my domain, which is 40 and is mattress Discat, like all about mattresses, is going to dominate these articles at some point.

So maybe as a long term goal, I will take them on because I don’t think, and I’m not betting that MarketWatch is going to switch to a mattress website. MarketWatch is a financial website, right? They just happen to want some affiliate revenue and they just happen to cover something and their domain authority is high, but they’re not an expert in it.

And Google knows that. Google looks at, you know, topical depth, um, pretty seriously. And so, if I keep pumping out content around comparing mattresses and things like that, I might rank and outrank these folks. Um, A friend of mine consulted a company called Healthy Hearing, and they kind of did the same thing, where they wanted to rank for hearing aids, and they basically went and covered everything under the domain of hearing aids, like, hearing aids underwater, technical support for hearing aids, batteries for hearing aids, all that stuff.

And then afterwards, they were able, after two years of doing that, and ranking for these subterms, they finally achieved the topical depth authority to outrank the big guys, right? Um, it does take time, um, but I just invest in becoming the niche. Um, authority, right? And that’s really important though, I think is really picking a niche of what you’re going to be doing, not doing everything under the umbrella.

One of the reasons I sold small business tools is because it was a little bit too broad. I was covering marketing, project management and sales tools, right? And I think niche is. Something that is going to be more valued in the future, in the near term. Being very niche, you know. Only doing project management reviews, right?

Project management sites, or tools reviews. Or, picking a very specific thing, you know. Mattresses for kids. Bras for whatever millennials, that kind of stuff and being super niche. And that’s where you can have a competitive advantage. 

Jared: You also mentioned, um, identifying problems in the SERPs. Maybe we can drill a little bit deeper into that.

What constitutes a problem? Um, maybe examples like let’s hear more about that because that’s often, like you mentioned, a way to overcome some of the other challenges, like a stronger competitor or someone who’s. Um, uh, ranking because they have a higher D. A. or something like that. 

Dmitri: Yeah, I love that. Um, I can screen share too.

I, um, tech, tech wise. Let’s see if I could do that. But I, um, I do this all the time with, um, with, um, topic ranker where I try to find problems specifically on the search. So like in the, um, worksheet here, I say, the first one is the page title is missing the term somebody searched for, called the title mismatch.

People listening to this probably heard about this, you know, you Google something. And a lot of times. You just don’t see what is supposed to show up there. Like the title has something kind of like it, like say it’s like AI content generation tools for small businesses. And the first thing that shows up is the best AI writers for 2024.

Yeah, content generation tools, AI writers, maybe, but content generation tools could be different things. Maybe. Sometimes it’s not exact, and that’s a weakness. That’s a problem, right? The article could be less than 800 words. That’s another issue, right? So, um, an article could be published more than six months ago.

It could be old. That’s a weakness as well. The page itself loads more than three seconds, takes it on, on mobile. That’s, that’s a problem because we want to make sure that we load our sites quick according to, you know, Google’s guidelines, right? So a lot of times. I look at the stuff and I try and like in my mind I see these red flags, right?

um, and so like the idea for topic language is like hey, i’m gonna Mark these as red because Uh, there are problems, right? There are problems for the SERP itself. So, so anyway, that’s what it kind of looks like. Um, I don’t know if anybody’s ever shared their screen in this, but I can share like what I’m talking about, so you can, um, yeah, 

Jared: we don’t really do screen share cause we have a large list or base.

It’s audio 

Dmitri: only cool. Well, yeah. Anyway, like when I see those weaknesses, like the. Um, page loads slow, the title mismatches there, you have forums like Reddit and all these different Twitter things showing up. The other thing is like the page, um, reading level should be, um, ninth grade or like most people are reading at eighth grade level in U.

S. We all know this. So like grading the reading level of the page is really important. So if you have like 10 results and seven of them have 9th or above reading level, 9th grade or above, you have something you can work on. You can create something that is Simpler to read or dumbed down version, you know, 

Jared: what do you think is, cause that’s, I mean, that’s a lot of work is to not only have to evaluate keywords on an individual level, evaluate them up against competitors and make sure that it’s fits within something that you can compete with, but then also go to the SERPs and evaluate each of the SERPs for gaps.

Like how many of the keywords that maybe you initially find, are you, Ended up writing about like what kind of elimination ratio do you end up with whether it’s From a competitive standpoint, whether it’s from, uh, Hey, all the, all the results in the SERPs actually look really good. So it’s going to be really hard to compete with this.

I’m just trying to get my mind around how many keywords you need to kind of go out and find going all the way back to that process because of what ends up, um, because of all the work you have to do to make sure and validate it. Well, 

Dmitri: that’s the problem is like most people don’t do this and I keep preaching and teaching people to do this.

Right. And when they do this, it works. But it’s a lot of work, right? So like, if we fire up any long tail tool out there for keywords, it’ll suggest Lots of keywords. It’ll also give us the competition metrics and the volume. It won’t give us the weaknesses and the problems. So we need to delve into them and see so like i’d say out of like 15 20 Ideas, I might even like maybe 10 percent of them like 2 out of 20 or something like that Might make it through just because You The majority, there’s just no real issues or problems and we could be biased and think oh We might be able to rank on it.

Oh, you know like we can create a better version of it You know and we’ll task a writer to say better But it kind of doesn’t need the better version like stuff out there. It’s pretty good a common thing that people do is They’ll take like, they’ll take all 10 articles and they’ll combine it. I don’t, I don’t know if that really helps anybody.

It just becomes this like giant behemoth that is like, um, unreadable or is readable. So, so anyway, that’s where about 10%, I’d say for me, that’s why I built the tool to help me with it. Cause I used to do this manually for like years. And I finally was like, all right, after the third acquisition, I’m like, I’m going to build this tool too.

Help me just. Find the ones that have weaknesses and get rid of all the others. I don’t care. Um, 

Jared: I don’t want to jump out of this conversation, but at the same time, I want to make sure we hear about your sale of your most recent business to SEMrush. I think we could probably pick any of the, The three businesses that you sold, but I mean, certainly everyone listening is going to have heard of SEMrush and I think that’s a really cool story to at least hear about, can you talk about kind of how that acquisition process looked like, um, and, uh, and just how 

Dmitri: it came about.

Yeah. Um, so I was building small business tools. Um, I’m good friends with, um, SEMrush, um, like sea level, like Oleg and Eugene. We, um, when they moved to Boston, it’s not too long, far from me here. We ended up having dinner and just kind of kept in touch. Um, Eugene lives in New Hampshire. I live in New Hampshire.

Um, and um, when I was building the site. They mentioned, um, because I was thinking about starting topic ranker and I was going to kind of think about partnering with them because they have an app center and we were going to build an app where they’re at a center. And that was sort of like the Genesis idea behind it.

Um, and he said, well, you know, um, since you’re thinking about partnering up with it by the app center, we also are buying blogs. And this was like before backlinko got acquired. And I was like, Oh, well, I don’t, I don’t, I don’t only cover SEO. You know, I cover other things cause backlink was all about SEO.

And I was friends with Brian Dean. And then after I, after they bought that clean code, I thought, Oh, maybe I should like talk to them a little bit more seriously about it. And they said, you know, um, the site, it can be MarTech, any kind of like small business topic that is relevant to our audience. And that’s when, um, we started talking more about, you know, working together basically at that point I was already working with them.

On the Topic Ranker side, pretty closely, so I knew the team and because we had launched the app in their app center, we were working with their promotions team to promote the app. And what that means is they’ll put banners and all sorts of promotions inside SEMrush for paid users to use your app.

They’ll also update their blog posts and things like that. And I had written for their blog before. Um, so anyway, based on a lot of recommendations that are like, you should really talk with, um, they had bought another property and the guy who was leading, leading that now became the point guy who was leading all digital acquisitions.

And I had known him, I had worked with him and we’ve done multiple projects together. Um, and so we just reconnected with him and he’s like, what are you doing now? And I was like, well, I’m filling this site, which I was told we should chat about. He’s like, yeah, let’s chat about it. And, and so it, yeah, it was pretty quick.

Um, probably the law, the biggest kind of formality that took the longest time is me going back to all my writers for the two years and making sure that all the articles that they have written, the IP is assigned to the new buyer, um, cause I didn’t have any formal paperwork, but it was a pretty straightforward, quick process.

Um, and I love working with the team now, um, building it forward. So that was like my only hesitation is like, what’s going to happen with it. Um, but they’re very much invested in building the property. Um, forward and creating new content and building, you know, traffic to it. Um, so yeah, I think overall it was just like a great experience, much better than my other ones.

Jared: Yeah. Well, you have quite the history of sites that are, uh, or properties. I mean, you’ve sold to Google, you’ve sold to SEMrush. Like those are some pretty good names overall. Um, I mean, so much of it seems to come back to who you knew. Was that a purposeful strategy? Like you just, as you’re telling that story, it was kind of like, well, I knew this person and then I got introduced to this person and then I followed up with that person and I continued talking to that person.

I mean. How, I don’t know how much of that is something that is a focus for you and, um, and, and is it something that pretty much helped move this along?

Dmitri: Yeah, I think like, um, knowing people and building connections is something that I’m, I’m pretty good at, and I try to do this regardless of whether I will get anything from people. I just help them or, or do stuff with them because I think they’re doing awesome. Like the guy at SEMRush, when we were working together, I had no idea that he’s going to work with him, that his, his project was going to get acquired, that he’s going to join full time, that he’s going to head up digital acquisitions.

There’s been none of that. I just liked him and I, we, we did this PR bootcamp thing together with him and he kind of moved fast, just like me. I like his working style. And I was like, Hey, you know, let’s, let’s just do a few projects together, just do stuff. We had similar interests. Um, he also had a bunch of projects going on and I did as well.

Um, and just helped each other out. Um, and later it helped out. Um, I’d say it was always like. Just knowing the person would just reach out. I didn’t know the buyer very well, but I got to know him through the acquisition process I would have done it differently. I think, um, I learned a lot from that process.

Um, and with Google, I, I kind of like walked away from it, which was kind of, people thought that I was doing completely the wrong thing. So I, you know, we, we’ve grown this company together and then the founders were like, Hey, you should join full time, get stock and, you know, like we’re going to be acquired.

And I was like, Oh, I don’t know, like acquired by a big company. I have to like work for somebody. I don’t know. And they’re like, it’s going to be a great payout. This is Google. Like, you’re going to go, I’m like, no. And then my wife was like, we’re talking, we’re like, well, we’re about to have kids. Like. Like, I got no money, like, just walk away from this thing, and they’re like, what are you going to do?

He’s like, I’m like, well, I’m going to, I’m going to start this thing called Just Reach Out. It’s going to be like this software thing. We have to dip into our savings, which we don’t really have, but we’ll, we’ll figure it out. And, you know, like, it was just like a crazy, insane move where it’s like, But it worked out well.

Um, I think the founders ended up like, like helping me out. Like I remember them covering some of the options or something. Like I got some money, uh, from the founders and that was really nice. Um, and to this day, we’re still great friends and he’s helped me so much in my business career, like building these other businesses and getting them sold by myself that had it not worked out that way, maybe it wouldn’t have worked out the same, you know, had it, but I basically helped them so much to get to a point to get acquired that they were like, all right.

We’ll help you, you know, and they’ve helped me over the years. Um, it’s like reciprocity, helping people and just. Having a good time. I think, um, that has helped me a lot of times. Not expecting stuff from people. Most people, when they do something for others, they just kind of expect, what am I going to get for my time?

What am I going to get for my money? Like, is it money? Is it this or that? Or am I going to get a connection? Am I going to get something now for it? I kind of just been doing stuff for people. Cause I like working with the people. I didn’t expect stuff from them. And it worked out for me. I am kind of like, I guess, intense and pushy sometimes, but other than that, sorry,

Jared: do you want to finish 

Dmitri: that thought? Um, no, I think, uh, intense and pushy a little bit, but that’s about it in terms of like getting stuff done, you know? So if there’s interest on the other side, I’ll, I’ll push and to get it closed. I’m not like one of those, like, Oh, there is a funny story with Gary Vaynerchuk, which I can talk about later or whatever you want 

Jared: about acquisitions.

Of course. Let’s hear it. 

Dmitri: Um, so there’s a video on my site. Um, and part of that video is me meeting Gary at his office. Gary Vaynerchuk wanted to buy Just Reach Out for a split second, like a split second. And you know how ADD and crazy he is. It 

Jared: sounds like everything about him is about a split second. 

Dmitri: It is.

So he called me and my co founder up to his office. My co founder flew in or drove in whatever. He wasn’t even in New York. My co founder was in Boston. I lived in New York. We went to the office. They filmed us because we were like part of the Gary Vee show or something us coming into the office and hanging out with him.

Um. And he put his like team on just reach out. He’s like, use this thing. We’re going to acquire it. It’s going to be awesome. And I was like, well, okay. Um, and I was like some kind of coach or advisor. I had so many of these coaches, but one of these advisors told me like, Hey, You should like play hard to get a little bit like you shouldn’t be like Pushy and communicative like you are cuz I’m like, hey you want to do this?

Let’s do this now Like I’ll text I’ll email I’m like ready to do stuff right away He’s like you should like give it space, you know, make him come back to you And I was like, Oh, this is going to be really hard. He’s like, trust me, it’s going to work out. He really wants it. Lo and behold, he like forgot about it.

Like totally forgot about it. I followed up like a month later, like something like three weeks later. And I have this email from him and still, he’s like. Sorry, DD, you know, I’m just gonna say that I wanted to do it then, but now I’m on to this new project, VaynerSports or something and, you know, wish we would have connected back then, but keep up the good work.

I was like, oh, man, what am I doing? But, um, anyway, I got to meet him. He’s like a cool, cool dude. And just like very. Um, humble and, and not like he is publicly. Very like, quiet and chill and just very like, like he’ll listen to you and you’ll be quiet for a really long time. And talk really softly and like, I don’t know.

Just very different from the public persona that he is. Like one to one, you know, 

Jared: well, I guess you probably won’t make that mistake again At least at least not if somebody like him comes around I guess but yeah, that’s a tough. Yeah, I think it’s

Dmitri: Just go for it like if you want it why why even like Why, why wait and do these games? I don’t know. I think you should just like be honest and be like, let’s do it. You know, just want to make sure it’s a good fit, you know, 

Jared: with the businesses that you’ve sold. I mean, you have, you’re a coach, you have students, you know, you’re involved with a lot of people and you see a lot of businesses and websites.

Like what are some of the biggest mistakes people make when they are building their business or their website that ended up hurting them in terms of sales? Whether it makes it so it’s not as easy for someone to buy it, not as attractive for someone to buy it, or maybe it decreases the amount of money they can make on it significantly.

Like what are some of the big mistakes you see? Yeah, 

Dmitri: so like the first thing that I learned when, when trying to sell a business. You need to have like 12 months or 24 months worth of revenue runway, right? like Anybody who’s going to be buying anything? They’re going to want to see a history of revenue like how much money you’ve made and profit for the business And I used to kind of willy nilly it and be like well, you know like Stripe reported this so i’m just going to put strike numbers across the last 12 months You That doesn’t really help like you need like really good proper accounting like you have stripe.

What are your expenses? How much do you spend and what’s your operating income so that you know, there’s a history and traction, right? If you’re going to purchase something So that was number one that I just, in terms of tracking, right. But in terms of like sales and impact on sales overall, obviously growth, people want to see growth.

But for me, I think it’s the lifetime value and the churn rate that have been the biggest drivers, um, in terms of multiple of what I could ask. I was in like the app space, software space with affiliate sites for soft, Basic affiliate blogs that people are listening, they’re owning, trying to grow, it’s really negotiating really good deals with those affiliate partners.

That’s going to be your sort of value prop for the buyer because that buyer doesn’t need to do all that legwork. So over the years, what I would do is negotiate really competitive terms. And see how they work in terms of revenue for your blog. Um, I would put most of my effort into that. And of course have your 12 months and 24 months of runway with your revenue numbers for your affiliate site for the blog.

But those terms, you know, like get really crazy terms with these partners that are paying you for, you know, 20 bucks CPC. Or paying you 100 bucks every time somebody signs up on their site. And, um, maybe you’re outranking the actual partner on some topics like, you know, Notion versus ClickUp and, or Notion versus Monday, right?

I outrank Notion for that term, right? Notion obviously wants to rank for that term because it has their brand name in there. Who’s this guy, Dimitri, outranking us? Now Notion is going to come back to me and say, Dimitri, um, can we work together? And this is where you want to be. This is how you want to do business and strike up these conversations and get these partners for your affiliate sites.

That’s what’s going to make your site more valuable and more primed to be sold to someone else. The more of these conversations you’re having, if, you know, you’re chatting with Notion, negotiating a contract, and you say, come back to the buyer, buyer of your site, you’re like, hey, But yeah, pick these keywords like notion alternatives for 2024, you know, you want to just hit them up Anyway, you can notion versus click up versus Asana start thinking these like branded terms Where you can outrank them because you’re quicker.

You’re better. You’re faster at it, right because Once they pick that term, it’s kind of, it’s harder, right? Um, to get in front of them. And you can sign up for their affiliate site and portal and get the basic payouts that they do. 10%, whatever, like 50%, whatever it is. But you, you want to outbid them at some point on, um, on Google organic or even on Google ads.

To, to make sure that they understand and see you as a potential partner, that’s going to be, you know, premium partner and that’ll help you value your business a little more. If you’re in the blog space, right? With software, it’s like a different approach. It’s more about like lifetime value of your user, your churn rate.

Those, those metrics help you value your Your business more. I 

Jared: feel like I could ask you several more questions along that line, but we’re coming to an end here. Um, Hey, where can people learn more about what you’re doing right now? I mean, you, you did mention, um, that you, you know, obviously after selling small business dot tools, you are working on something new topic ranker.

com, but we’re gonna be able to learn more about, about that and about, um, and about what you’re doing. 

Dmitri: Uh, yeah. So my, uh, my site is, is topic ranker. com. That’s my latest project. TopicRanker. com. Um, and then my personal site is CriminallyProlific. com. Um, that’s where people can check out my story. Um, it still has all those old, uh, cold email articles, uh, that they can see and be like, Oh, those were the mistakes that Dimitri made.

Uh, so you can kind of laugh as, as you look through the blog, cause I still haven’t updated. A lot of them are still kind of somewhat ranking. I just. Don’t know what to do with them. Um, but it’s, um, it’s got my, um, portfolio of customer customers. It’s got links to all the other projects, like, um, my, my academy and my coaching business, that’s my other sites.

So yeah, those two sites. Topic and criminally 

Jared: Dmitri, thanks for coming on the podcast. Uh, I, I, I’m, it’s what a fascinating story you have. You clearly have a track record, and I hope everybody listened up because you’ve done this over and over and over and over again. I’m sure the next time we talk, you’ll.

Found the same solution for topic ranker. com, but, um, we’ll wait till, uh, we’ll wait to see, but I have, I have confidence that that’s the direction it’s going given your 

Dmitri: history. So thank you. Yeah. We’re already ranking for long tail pro alternatives. Actually. I was just talking to Spencer and I was like, Hey man, we’re on the first page for it.

That’s awesome. But we’re doing our own thing, the same thing, keyword research and all that. Yeah. Thanks for having me. It’s always a pleasure. 

Jared: All right. Well, thank you, Dimitri. We’ll talk again soon. 

Dmitri: All right. Talk soon.

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