Ep 314: Business Acquisition Mistakes Buyers & Sellers Make When Acquiring Online Business with Ross Gerson

Many buyers overlook one of the most valuable yet intangible assets that come with acquiring an online business. 

This episode features Ross Gerson, founder of DealSlide.com and a former broker at Empire Flippers. With extensive experience on both the buy and sell sides of online business acquisitions, Gerson shares key insights into the most frequent mistakes buyers and sellers make—and how to avoid them.

The discussion covers several compelling topics, including Krause’s near-experience as a broker at Empire Flippers, a role Gerson had originally approached him for. Gerson also explains his transition into acquisition advising and consulting, detailing his work with WebStreet and his involvement in acquiring over 15 to 20 content sites.

You will gain valuable insights into critical acquisition mistakes, such as the importance of direct communication with sellers, defining clear acquisition criteria, and navigating the transition period after a purchase. The conversation also highlights Deal Slide, Gerson’s marketplace that aggregates listings from over 20 brokers, streamlining the search process for buyers.

Packed with expert advice, this episode guides anyone looking to buy or sell an online business, helping them maximize their acquisition strategy while setting themselves up for a successful exit.

Let’s get started!

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Episode Highlights

03:00 Why Ross moved into online business acquisitions?

11:00 Ross learnings from being a broker at Empire Flippers

19:00 Get an extra from the deal!

25:00 Surprises in the seller’s side

39:00 Where to find Ross?

Courses & Training

Courses & Training

Key Takeaways

➥ Many buyers enter the market without a clear understanding of what type of business suits them best. Taking the time to assess personal skills, experience, and workload preference is crucial. 

New buyers often fear looking inexperienced, but embracing the learning process leads to better decision-making.

➥ Off-market deals are not always better. Broker-listed businesses provide structured deal flow and often undergo vetting, making them less risky.

➥ Some sellers don’t even realize their business can be sold, while others prioritize terms over the highest price. Understanding seller psychology can create win-win deal structures.

About The Guest

Ross Gerson is the Founder of DealSlide.com, former broker at Empire Flippers for 2.5 years, an acquisition Advisor to WebStreet for roughly 3 years, bought and sold approximately 15-20 content sites for his personal portfolio.

Connect with Ross Gerson

Transcription:

What if when you acquire a business, you forget to take advantage of one thing that you're purchasing that's intangible that nobody realizes how valuable it is? Hi, I'm Jarrett Krause. I'm the host of the Buying Online Businesses podcast and today I'm speaking with Ross Gerson who is the founder of dealslide.com. Now, Ross was a former broker at Empire Flippers for two and a half years.

We also talk about how I almost became a broker at Empire Flippers and how Ross called me to see if I wanted to become a broker at Empire Flippers. What ended up happening there, interesting story in how we bumped heads there. And then also how and why he transitioned to being an acquisition advisor, and he's been a bit of a consultant, worked for Web Street for roughly three years, and still does some consultancy. His portfolio has bought more than 15 to 20 content sites.

He has one that he mentions in the pod that they're also looking for an operator. And in this podcast episode, it's such a refreshing conversation around what Ross learnt from buyers working as a broker from Empire Flippers. We talk about not getting on the phone. We talk about acquisition criteria and how tough it has been for people that are first buying to try and work out what the acquisition criteria is.

I share some things on how you can nail down your acquisition criteria and learn more about yourself to be able to do so. We also talk about like speaking to sellers and how valuable and important that is, not just before you acquire the business, but through the training period, which I alluded to at the start of this podcast episode.

We also talk about what he learned from sellers working as a consultant for Web Street and what sort of deals he helped sell, sorry, for and acquire, actually for Web Street once I've done funding, and what sort of business models as well.

He's learned so much from the sell side and so much from the buy side. It was a great conversation because we sort of run parallel to one another and have done a little bit of different things in our career, but we've helped so many people acquire and sell businesses and it's such a refreshing conversation.

We also talk about the Deal Slide. It's a marketplace where he just scrapes a bunch of deals from 20 plus brokers, and how you can, it saves time in the search phase for looking for businesses. Now, there's so much value in this podcast, you know, about what buyers get wrong, what buyers do right, what sellers get wrong, what sellers do right, and how you can become a better acquirer for your online business, and also how you can set yourself up for a good exit as well.

Enjoy the pod.

Hey Ross, welcome to the pod and thanks for your time.

Hey Jaryd, thanks for having me. How are you?

Yeah, I'm good thing. Thank you. And yourself?

Doing well, Awesome. Yeah.

Like I just want to dig into your journey around what you did before online businesses and Empire Flippers? So, if everybody listening, you've worked at Empire Flippers, and we want to get others a cool little story that we're going to share soon, around that, myself, Empire Flippers, and yourself, and Empire Flippers. But how did you, where were you at?

Why did you decide to move to the online space and get involved with Empire Flippers? Yeah. So I was always a fan of Empire Flippers and I listened to their podcast, read their blog, and was interested in acquiring a small online business kind of way back in the day, 2015, 2016, 2017, when they were selling much smaller websites on Empire Flippers and online businesses.

And that's how I came across Empire Flippers. I applied to work for them the first time that they were hiring salespeople for their team, essentially brokers to join. And I didn't get the role. And then I met Joe and Justin in person at a conference in Bangkok. I was trying to kind of do my own online business.

I was doing some digital marketing, trying to figure out the nomad lifestyle, and met Joe and Justin at the right time, and started to work for them in January of 2018 and did that for about two and a half ye, ars and it was great experience. So, did it because I was a fan of Empire Flippers, really curious about the space, and thought it would be super interesting to learn about which businesses are making money, and meet really interesting buyers and sellers, and learn by working for Empire Flippers.

Yeah, that's cool. So what were you doing before you started your own online thing? Did you have a job or were you out of college? Where were you at and why did you? Yeah, out of college I, actually followed a more traditional path and I was working within real estate and living in Chicago. And then, you know, I was listening to Empire Flippers and other podcasts and kind of trying to learn about online business and was also really interested in traveling.

So I was learning online business and was doing Facebook marketing at the time. So I left my job out in Chicago. I was doing some recruiting as well, kind of helping out with some friends' businesses at the time. And was trying to kind of figure out what I wanted to do with my life.

The Facebook marketing and digital marketing business that I was starting was kind of more of a freelance thing. And I knew it wasn't the right fit. So when I met Joe and Justin again, it seemed like the perfect opportunity to kind of dig in and learn about online business. So yeah, it was a transition going to the online business world.

Yeah. So cool. Congrats.

Before we hit record buttons, you were mentioning that you called me. Was that correct? Do you remember when that was? What's the cause, I actually, I think it was in 2015 or 2016. I applied to work as a broker with Empire Flip as well. And I got denied and I've spoken to Justin and Joe multiple times now since this and they've been on the pod and I've been on the Empire flippers pod multiple times.

And as a bit of a running joke around, uh, what would have been different in Empire Flippers if they had not said no. But yeah, what was it? How did you come across me? Like, I'm curious. Was it the podcast first or was it, yeah, how did that look with Empire Flippers? Yeah, well, I, the same role that you applied for, I think you mentioned around 2016, 2017 was the first job I applied for at Empire Flippers. And that's what I ended up doing the second time around.

Yeah, I remember exactly where I was when I called you. It was right around Easter and it was the Philippines. We just wrapped up two-ish months of training with Empire Flippers. And then we flew out to the Philippines for a company retreat. We were actually with the CEO, Joe, at the time.

And he wanted us to, it was the first time we were meeting him, and he wasn't with us at the training, and he wanted to hear us on the phones. And it was a Monday in the Philippines, but Sunday night in the USA.

And normally we're calling people in the States at the time. Part of the reason that Empire Flippers brought me and other people was to go through their list of people and start to outreach because it was more just reacting to people that would raise their hand that they wanted help or want to talk to someone about buying and selling an online business.

And Empire Flippers had this massive database, and they wanted people to go out and call people that were active on the marketplace and looking at deals, but not talking to anyone. So we were just going through.

HubSpot, seeing people that were active or hitting certain benchmarks or metrics, and calling them, or telling us their criteria, going through different filters and calling them. And it was, it was Monday. It's like I said, in the Philippines and Easter Sunday in the USA.

So I was looking for people that I couldn't, didn't want to bother on Easter on a Sunday. So I remember I, the list was small for Australia and I saw your name and I called you. So at the time, I don't think I knew that or maybe you were just starting this and I'm not sure where you were at at the time with this channel.

Yeah. I don't know what year this was, 2017? This was Q1 2018 when I would have called you. Okay. Or start of Q2. So Easter, sort of 2018. Yeah. Yeah. Yeah. I had started buying online businesses. I got the domain in 2016 and I launched the business in mid 2017 or the start of 2017. So I was already coaching and I would have had probably a full book of clients through Bob.

Yeah. So what did I say? Do you remember? Do you remember the conversation at all? You're just telling me that you were active and working with people, and that you share the story that you applied to work for Empire Footers previously. And I think you had a lot of ideas at the time, and you already wanted to start the business that you started. And maybe you mentioned that to the Empire footers at the time.

And I think you mentioned something along those lines of that's why it didn't end up working out, they missed an opportunity with you. Yeah. Thank you. Yeah. Justin and Joe, I've talked about that, like I said, multiple times since, but I think the biggest reason that I wasn't able to work with them is because they had a policy that if you are a broker, you're not able to acquire businesses, online businesses, even if it's outside of their marketplace. And I was like, well, I can't not like, I'm in this phase where I'm just acquiring and I can't guarantee that I'm not going to do that.

So it was a mutual thing between us both. It was their policy, but I was just being honest. Like, look, I want to build my portfolio. It's the thing I want to do. You were with Empire Flippers for nearly three years. And you were a broker, so you moved into being a broker. What did that look like? What were some of the things that you learned through that period as a broker? I would say it was priceless in terms of the education.

Constantly talking to buyers of all sizes that are interested in acquiring online businesses, and learning about the processes, and talking to sellers of all different types of businesses. I would say the most interesting part for me is where the buyer-seller conference calls are, where you can kind of be a fly on the wall and listen to buyers interview sellers and hear them get to know each other.

And then also have those conversations with the buyers and sellers separately before and after the call. So I feel like that was really where I learned the most on those calls with buyers and sellers.

And I will say, something you mentioned just before previously is that actually Empire Flippers did not have that no side gig policy, which is what they called it at the time, when I started, so back, I think until 2019, we were able to buy online businesses. It just wasn't on Empire Flippers, so we could buy elsewhere, and they changed it.

But now I believe that they can. I'm not 100 % sure of the policies, but when I was there from, I would say, late 2018 to whenever they made the policy, I was actually buying small websites myself on Flippa and really wherever I could that worked with what I was, my criteria, Flippa seems to have the most sites in the kind of smaller content site range. Yeah. So that was part of why I ended up leaving Empire Flippers, because they made that policy where we actually couldn't buy or do any sort of online business as we were a broker.

So I decided to continue at Empire Flippers for a bit and just focused on a few of the sites that I already acquired, but eventually I ended up leaving because I wanted to keep buying businesses similar to yourself. That's very interesting that they, at the start, had that policy that opened it up and then shut it back down again.

I would say it's, I don't know, what do you think? Do you think you being able to buy your businesses on the side, taking that education that you learned from Empire Flippers, acquire your businesses through Flipper and maybe offline, you would have do you feel like you would have learned through your acquisitions, like being able to become a better broker as well for Empire Flippers?

Like I feel like that would have been a pretty amazing education that you got that Empire Flippers didn't need to pay for because you're doing on your own time. Yeah. Yeah. I a hundred percent agree with you. Think buyers, end sellers want to work with people that they know have acquired and have skin in the game, and are online business operators and owners as well. So I think, you know, it goes a long way.

I can see from their side of it, wanting to make sure that everything's kosher and we are, an Empire Flipper broker has a lot of access to information, and they want to make sure everything is good there, and you're focused on the role. I understand kind of what you're saying as well.

Think that there's a lot that you can learn from acquiring on your own, and it makes you a better broker as well. For sure. From being a broker, what would you say are the top two things that either surprised you about buyers, or yeah, top two things that you learned from buyers that you've gone away and use yourself as an acquirer, or top two things that you sort of surprised you about buyers.

I'd like to, and then we'll go and talk about the flip side of sellers too, but yeah, let's stick with buyers for now. What did you learn from them as you were advising and brokering? Yeah. Yeah. The first things that I thought of actually weren't things that I learned from buyers, although there's tons of things that I learned. Feel like that's a large list.

The first thing that came to my mind was more things I was surprised about in terms of a lot of buyers, they're resistant to talk to sellers on a call. They think that they can do a lot of their due diligence just over email, back and forth, or whatever the broker provides. And I think it's invaluable to get on a call and meet the person that you're buying it from, even if you're buying a $5,000, $10,000 website.

I know people may disagree with me, but I was always surprised to see sometimes people buying $100,000 plus website or online business and not having a conversation like this with the seller. Crazy. That kind of shocked me. It is crazy. I've sold businesses before where that happened, where I listed a business after I left Empire Flippers on Empire Flippers and right in that kind of range.

And no conversation with the buyer other than email back and forth. And then they learned something in migration where they asked a question and I'm like, listen, maybe we should have asked that before we did. Yeah. I just think that's one thing. Yeah. Before we move on to the next one. Cause I know you've got so much to share, and thanks Ross.

The reason being for that. And I noticed this is because most people, when they first start, they may feel a little bit intimidated and don't want to feel like they're on a, like they're underneath somebody, like cause they're just starting and they're like, I want to buy a business. Know nothing about online businesses, but I want to buy it. And I don't want the seller to think I'm stupid.

So like that intimidation of not getting on the call, which is ego stuffing us up, right? Getting in our way and like allowing us to be far more open to risks versus just like put that aside, understand that you're learning and you're wanting like, I try and tell people to get on the phone as much as possible, even $5,000, $10,000.

Like for somebody that's saved $5,000, $10,000, who knows, I might have taken them a couple of years to get to that point. So what's one phone call and putting your ego aside, checking that at the door. And I think it's, I'm glad that you brought that up because it's, it's just silly. It's silly not to speak to a seller. Like the biggest, the most valuable part of the transaction is typically the relationship that's.

So thanks for bringing that up, Ross. What was the other thing that you were going to spit out before I cut you off there? Yeah, it's funny. What you said made me think of more things as well. Even like on the small ends, I would say even large buyers that I've worked with, there's a lot of times where it's like, we'll be debating something and having a conversation and we could just figure this out with a quick conversation with the seller.

So it could even be a half a million, you know, million dollar plus deal and I get it. No one wants to waste someone else's time, but there's so much you can learn and discover and figure out if it's a good fit or not by just getting on a call and hearing it directly from the horse's mouth.

And who knows what you're going to learn to apply then for your business or another business that you end up acquiring. Know, and then another thing I thought of when you brought that up is the fact that people are nervous to talk to sellers and there's that whole kind of ego thing you mentioned and the fear of looking like they're a newbie that makes it almost impossible for them to end up pulling the trigger and buying a business or it's going to delay it by a ton of time or make it more risky because the best way to learn is through those calls directly with the seller where you can ask questions and look at the profit and loss statement and then learn what you like and what you don't like. Then you can take that and tailor your criteria for the next calls.

So when I would talk to people, especially those who are new, I would always encourage them to get on calls and look at as many deals as possible because I know that would help them figure out what they like and learn things. And there's always going to be things that pop up, and the people that yeah, that don't get on calls, they either fade out over time or it just takes them a super long time to buy a business if they ever do. Love that. I love that you said that.

Yeah. It's the biggest gatekeeper, it's not building relationships with people in the space. And also like once you buy the business, you've got to build a relationship with them anyway. Well, you should because then you're robbing yourself of part of the business. And the part of the business isn't like that, you're buying isn't just the accounts, right? Like the sales distribution channel, the Amazon account, the website, the main hosting, if you're getting hosting coming along with it, like that's a portion of the assets that you get.

And this is just coming up to me now, is that one portion of the asset that is intangible that you are acquiring is the knowledge and access to the seller and their knowledge through the training. That's not something that's written down in an APA or a contract of sale, it's like, you're buying that. If you don't acquire it because of your ego, like you're missing out on so much value, right? You're missing out on a big portion of like how you could de-risk or grow the business.

A hundred percent agree. I love that.

Yeah, there's so much value to get on the call, whether it's building rapport to win the deal, or then the seller knows you, and it's a different level of the relationship when it comes time to help you or ironing out what the appropriate support and training is going to be. But I 100 % agree personally in deals that I've done, I become friends with the seller.

I iron out very specific training and support because a lot of times they know something that they might not value as much as I do, like keyword research or some SEO stuff. And I'm like, hey, why don't we do a few calls to talk about this, or you could help me hire someone or teach my VA how to do this, et cetera. And to them, it's no big deal.

Like, oh yeah, I look at Ahrefs and do this kind of stuff all day. It's no big deal to have one, two calls with you. It's super easy. Where for you, it feels like a big ask, but you're never going to get that without the relationship and the call there. So yeah, I 100 % agree with you there. That's a great perspective and a great example, Ross. Like it's nothing to them and it might be playing it up in your head. Like it's a big deal, but it's like, yeah, just do this.

That's fine. Happy to share it. I always advise buyers to like as a sweet mirror on the deal, like any support and training, like I'll have a conversation with them. Like what would be super helpful for you? What did you like about the seller, or maybe that he does, that he could help you with? And yes, normally not a big ask.

And in my opinion goes a long way. There's a lot of buyers, I think that don't care too much about that kind of stuff. And maybe I overthink it, but to me, it seems like low risk, high reward to try to soak up as much as you can, like you said, like the DNA from the seller and try to learn something and get something extra in the deal that is perceived as a low give for the seller.

Yeah. So much value in there. What else have you learned from buyers or even sellers now, like that either surprised you or was something that's helped you significantly in your acquisitions?

Yeah. I mean, the more calls you do, the better. I'd say like my advantage when I was doing my deals and when I help buyers and get on calls is like, I've been on so many of the buyer-seller conference calls that I think I'm good at developing rapport and learning things about the business to help assess it being a good deal or not. But the first thing, when you mentioned this, actually that I thought about is that surprisingly, most buyers don't know what a good fit is for them.

They have an idea, but they come in thinking it could be a SaaS business. It could be an e-comm business. But they're not zoned in on what's going to be their unfair advantage and be the best fit, and they need some help, and it's a process as we were kind of talking about. That's something that surprised me.

And then a lot of people think that like, there's this magic private deal flow out there and like nothing on the brokers is good. And that's something that always frustrates me and surprises me. Like I get it. Yes, that's a great way to get deals and have deals that aren't out there. But there's a lot of that's something that constantly comes up that buyers are always looking for off market deal flow and a lot of them are like just overlooking broker deals because they think there must be something wrong with it because it's on a marketplace, which I think is wrong. Agree.

I agree with both of those things in terms of like the private off market deals sub 500 K. Like I've, I was going to build out a private deal flow marketplace, a membership, actually, and anybody's open to doing that, throw it out there as a business idea for people. We looked at doing it and I do give some private deals to my members in the buying online business community. It's not a whole lot. I was gonna charge for it, we just do it for free now.

It's just a bit of a bonus. To find those deals at that price range, under half a mil range, is like most of the deals that you're getting are not great deals. And then just because they're off market doesn't mean they're good and people are likely not gonna wanna buy them and there's a reason, the way I look at Empire Flippers and other brokerage sites is like, they are the deal flow.

Like you guys, that's what a brokerage business is. It is just at a high level, it's just your flow and then bringing businesses to the market. How is somebody with less resources than you guys going to be able to do it better? Like you might be able to do it, do it a fraction of it, but it's tricky and I've looked into it and we've tried to do it really, but it's just a tricky one to do. So spot on.

What was the other one that you were mentioning around? Yeah. I was mentioning buyers not knowing exactly what they want when they get started. They're broad on their criteria without really zoning in on what's going to be the unfair advantage for them. This is why I have a job. This is why the community exists, because it helps people to sort of work out where they're at, what skills they do or don't have, and what sort of workload they want to take on or not take on to nail down an acquisition criteria.

And even then, what happens when they listen to multiple people, instead of listening to themselves or tuning into themselves, is we come up with things that aren't specifically right for us. And that's what I like to teach people. Learn to listen to yourself, build your values. Cause when you study yourself more than studying everybody else, you're going to be able to get better results for yourself versus like trying to do what other people have done. Cause then it's just confusing.

You go to the marketplace, like, what about this? What about that? But like, if you know yourself, then you can't go wrong. Yeah, a hundred percent agree. I think it's really helpful for buyers to sit down and write down their experience and what try to map out what the perfect fit is going to be for them based on lots of things, you know, their resources and like you were mentioning, you know, time they want to spend and experience and all those things.

So another thing I was thinking about as well, you mentioned before, kind of crafting, obviously knowing where all the deals are on market, but also thinking about finding off market deals, like you were mentioning, like you're just getting deals sent to you because people know you're in the space. So I think it makes sense to kind of be out there and try to attract deal flow that might be private, but at the same time, keep your eye on all the marketplaces to maximize.

I mean, if you have the resources to build out some sort of way to go out and be strategic to get in front of off-market deals. Yeah, like it's just building your brand in the space. And it's like, can see why a lot of people don't do it because they might do two acquisitions, but to build out deal flow to get two acquisitions in the space of five to 10 years, it's a lot of work to do that, which is, I don't know, the lower end, maybe they're buying like a lot more, but yeah, you got to throw your, put your neck out there to do so.

In terms of like on the opposite side, the outside buyers, what about sellers? What are some of the things that you like, surprised you about, some of the sellers? It could be anything like accepting more, like less money for a deal, but for better terms or a better buyer, how they operate, why they want to sell. Like, what are some of the things that have just surprised you about sellers in general?

Yeah, we could do a whole podcast about this one, I think.

Yeah, this is the wild west. Sorry? Yeah, I would just... It's just really a lot of... It's a newer market. Buying businesses has been around for a long time. Buying online businesses is a lot more recent. And a lot of times these monetizations are 10, 20-ish years old and they're in the early years of being tradable assets. The rules are kind of like being written as we speak for a lot of these monetizations.

I feel like there's a lot of debate over the best practices sometimes, and people taking things from traditional &A and assuming that's how it works for small online businesses. And then some people have no idea as well. So that's something that kind of shocked me, is a lot of people that come into it and they go to sell their business, and like, they don't even know they can sell it.

They don't know what it's worth. They don't think anyone's going to come in and make an offer that's not all cash. It's like crazy varying opinions and you get, it's a very international market as well. And I think especially the seller market is more international, I'd say, than the buyer market. It seems like there's buyers from all over, of course, but I would say predominantly they're based in the USA.

Whereas sellers, it's a lot of times someone in Bali that likes to surf that has an e-commerce business or a website business or SaaS business, and they go to an Empire Flippers or Acquire or Flippa or Quietlight. I'm not saying that's a typical seller persona, but I was surprised how international it was and how varying the understanding of how it works, where someone could come in. It really would almost depend on the savviness of the seller to know how hard the deal was going to be.

And it also surprised me how much goes into it where you're like the seller's friend, their broker, their therapist. And it's a very I've had that conversation. Somebody asked me just yesterday, I'm going to acquire a significant size business for them as a couple. And the partner asked me if you can make such good money through buying businesses on buying online businesses, and the ROI is so good.

Why did not more people do it? And the answer is it's a similar same thing as sellers not knowing how much or knowing that they can sell their business or how much they can get for their business and what that looks like and whether they can get all cash or it's going to be finance or whatnot is because people just don't know. Like you said, it's very green space, like acquiring assets and acquiring businesses have been around for a long time, thousands of years, hundreds of years, right?

And the internet's been around for what, like 30-ish years or so? It's green. And then for that, in those 30 years, everybody's only talked about starting businesses. Like if you want to make money online, which is a lot of people's goal, because their real goal is, like, can I help you, like, is to get la ifestyle, more time, more freedom, so that the vehicle's online income.

And most people, what do you hear? Well, like if you want to make an online income, what did people say? It's like, you just start your own online business, but that's not like, nobody knows you can buy it, hardly outside of our sphere, like our world. Like most people, don't even know you can buy a business, let alone sell a business.

So I'm glad that you brought that up because, like people come to me and it's like, Oh, what should I do with my business? I'm like, you can grow it. You can sell it. Like Oh, sell it. Like, how much is it going to be worth? Well, it depends on the business model, but it's pretty surprising when somebody says, Oh, I'm making a hundred K a year.

Well, you could sell that thing for anywhere from 200 to 300 K on average. They're like, Whoa, like what would that do for my life? Have you seen how life-changing exits have been for a lot of sellers, and like, tell us some of those stories. Yeah. Um, I was reminded immediately when you just told your quick kind of story that I met a woman that had an FBA business in the UK and she sold it for 400 something K kind of during the whole FBA aggregator boom of things.

But when I talked to her, she's like, I didn't know anyone would buy a business my size. I was like, wow. Just created. It sold, I think, for full list price in like a week or two, because it was just craziness at that time. Yeah. That was a one. Yeah. It's crazy. And she probably got a good multiple. Where she literally.

Yeah. She liked it, too, I think, like I helped her a little bit with negotiating it because I wasn't a broker at the time. I was an advisor and I think I got put in touch with her, a few mutual friends. And, yeah, I think, I think she listed for just under 40 X and the monthly profit. I don't remember a lot of the details, but I remember like, she thought it was like, Oh, I think it's too high. I'm like, I think we're good and it sold right away.

Yeah. That's great. Congrats to her.

Yeah. So you've bought a bunch of businesses as well. You started out buying small content sites. What does your portfolio look like now? Like what's the business models that you got in there and are you still bullish on content sites? Where are you at? Give us a bit of a recap on your acquisition journey and then where your portfolio is at now.

Yeah. So I bought a handful of sites 2019-ish before Empire Flippers reinstated or started the rule, where we weren't able to buy online businesses. And I took a break for a little bit, and I started again, the summer of 202,0 when I left Empire Flippers. I purchased roughly 15 or so content websites. It's all content. I've never done anything outside of a content site and predominantly display advertising.

I've done a few affiliate and some of the sites are mixed with affiliate display advertising, but it's mostly display ads. And for some reason, that's just what I was most drawn to and most interested in and where I'm kind of curious and enjoy looking through PNLs and looking at Ahrefs and thinking about ways I can grow the site. I don't know why. For some reason, it's fun to me.

Whereas the other ones are interesting, but I don't think about them in the same way. I like SaaS, obviously, but e-commerce and physical products have never appealed to me like content and the more digital side of things.

So yeah, mostly display advertising. I sold most of those sites. I still own a few of them. I have one that's way larger than most. It's in the music space. So it's like music charts and facts and things like that. And it's almost like a compilation of Billboard top 40 charts, the top 40 songs each week from 1955 to present day, and ranks for all sorts of keywords in that category. And I bought that in 2020.

I'm a minority owner now and I've brought on two partners and we're trying to hire someone to help us operate it full time. Yeah, it's a pretty interesting story without me rambling too much. But when I first discovered the deal, I could have bought it for just a few grand. I ended up paying way more for it about a year later, but it's worth a lot more than I paid for it. Yeah, it was kind of a wild journey with that one.

Yeah, congratulations. That's cool.

So you got three partners and are looking for an operator. That's cool. Anybody, anybody that could be an operator of the LinkedIn site, reach out to Ross. I'm sure you'll get some hits. Absolutely. Yeah. Yeah. Maybe list some qualifications they need to have. Yeah. We think have a job posting up right now. So we're looking for basically an SEO to run the site and manage it.

But we want to de-risk and build a real brand and do email, and we've, knock on wood, done well through Google updates, but things are changing so quickly. And, I'm sure you've seen lots of unfortunate things with Google updates, and people that have those sites, I've seen it and I've had sites that have gotten hit. So yeah, kind of need to do that immediately. So the ideal person would be someone with a strong CEO background, but ideally, as the experience and know-how to try to build a real brand, build an email list, and do some other things outside of Google organic.

Yeah. Got ya. Cool. Cool. And so you were an advisor for the acquisition advisor for Web Street. How was that different? How was that role different from Empire Flippers? Or was it not really? Yes. No, it was similar, but very different. Same, same, but different as I say in Thailand, right?

At Web Street, I've been doing that for about three years and I focus on just helping them acquire. So it's more buy-side focused, whereas Empire Flippers was helping sellers. And Web Street was started by Empire Flippers. It was formerly called Empire Flipper Capital and they rebranded to Web Street.

I started there after their first fund. They've raised, I believe, 10 funds now. So I started in fund two, helping their team and the operators that they bring on with all things acquisition. So similar to probably what you do with your clients, kind of helping them through organizing their deal flow, figuring out which ones they want to prioritize and move to the next level and disqualify and kind of help them think through buyer seller conference calls, making an offer, kind of all things that go in the acquisition phase.

So kind of, would step in after they've raised the money and then I would work with the operators in the Web Street team to help them acquire businesses more efficiently. So it was different, but similar in the same way, kind of applying what I learned at Empire Flippers and what I've learned buying my deals and advising some buyers as well. Yeah. Yeah. Cool. Yeah. It's cool to get to be a part of both sides.

You've learned from both sides and sounds like in that realm, there's maybe a bit more finance on the buy size. You just got to learn a little bit more about that. What sort of deal sizes were you helping acquire with Web Street? Yeah, it's evolved. So they raised funds around different operators or portfolio managers and their skill set. So it was FDA businesses, content sites, KDP businesses, and now more agency and SaaS businesses are trying to buy agencies.

Hard to find good, good agency deals and SAS deals as well. Mean, there's a lot of them, but to find a good one is not as easy as it would seem, but yeah, they range, I would say from low six figures. Now I think the biggest deal that I've done through Web Street was just below three and a half million.

Okay. Cool. Total total. Yeah. Congrats. Yeah. That's awesome. Yeah. So much, so much learning, so much knowledge on the sell side and the buy side, and now deal slide founder of deal slide. What's a deal slide? Tell me about the deal slide or us, and what your goals are for it.

Yeah. So honestly, man, it was kind of inspired from being in a space for a while and being a little bit frustrated on they're not having to go to all the different broker and marketplaces separately. And it felt like there should be a better way to see the deals in one place. So it was kind of built, out of a frustration where it was like there had to be a better way to.

And there were some other, other people that have done it, but they're not as updated or as robust as what that deal slide, but essentially it consolidates all the online businesses that are for sale into one place. So we'll save a ton of time as opposed to if you're serious and want to look for a deal or just figure out what's going on in the market, you would need to go to Flippa, to Empire Flippers.

We're pulling from 20 sources right now and we have more than 4,000 deals and we update every single day. So if there's new deals, we put them on there. If there are deals that are taken off from the broker or websites or marketplaces, we remove them.

So it saves a ton of time when you're looking for deals and you can search by keyword and price and monetization niche, et cetera, to filter down and find businesses that meet your criteria in seconds, as opposed to what that would take previously. I'm going to go to all the websites and check email lists to keep track of the market. And then working with Web Street, they're trying to find deals.

And it always felt like we were missing a deal, and also keeping track of the deals from spreadsheets. And a lot of buyers do that, I found that I'm working with, and it just felt like there should be some consolidated platform to make it easier. And that's how it was inspired. Yeah, so I think it's TBD exactly where it's going to go. But right now it's a place where you could see all the listings in one platform from all the different brokers and marketplaces.

And you can save your criteria or track specific listings, and we'll notify you if a new deal goes live that hits the criteria, or if there is a price change or something in a listing that you want to track, we will send you a free weekly update right now. And the plan shortly is to charge for a tier of kind of more safe searches, and more track deals, daily updates, and some things that we can offer on historical pricing and things like that. But yeah, it's, yeah, I'm very excited about it and I think it'll be interesting where we go shortly.

Well, everybody check out dealslide.com. I'll put links to that in the show notes, but where else can people find you if they want to reach out, Ross? And thanks so much for your time as well. Coming on.

Thanks for having me. Appreciate your reaching out. I think LinkedIn would probably be the best spot or dealslide.com. You can create a free account and you can book a call with me through there as well. So I would say dealslide.com. Book a call if you'd like to chat or LinkedIn. That Ross Gerson would be the best two places.

Awesome. Thank you so much for your time.

Appreciate it guys. Links will be to all of those in the show notes. Thanks for listening. I'll see you on the next one.

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Jaryd Krause is a serial entrepreneur who helps people buy online businesses so they can spend more time doing what they love with who they love. He’s helped people buy and scale sites all the way up to 8 figures – from eCommerce to content websites. He spends his time surfing and traveling, and his biggest goals are around making a real tangible impact on people’s lives. 

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