261 - Best of 2025! How 1 Premium Domain Name Unlocked $100+ Million in Revenue with Jesse Tinsley

16 Dec 2025 · 36 min · 17 chapters

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In short

Episode topic: Jesse Tinsley’s “best of 2025” recap on building a bootstrapped HR-tech rollup via premium domain acquisitions, playing offense during downturns, and using creative deal structures (seller notes/earnouts) to buy assets with minimal risk.

Guest background

Jesse Tinsley, founder/operator behind recruiter.com and employer.com; grew up in Silicon Valley with entrepreneur parents (father construction, mother recruiting agency). Previously worked at tech companies (Coinbase, 23andMe, Protocol Labs) while running a consultancy recruiting business (JobMobs), then scaled into multiple HR/payroll/workforce products.

Key claims

8 acquisitions in 2 years; $500M pending acquisitions; 100% bootstrap to $100M+ revenue run-rate; premium domains create “brand authority” and unlock enterprise ARR; recruiter.com acquisition was a “deep end” first M&A; downturn = opportunity to buy.

Notable examples

bought employer.com for $9.2M; acquired recruiter.com via public-company deal (March 2023 carve-out; larger close Aug 2023); brands include recruiter.com, employer.com, beforeyouapply.com, Bounding Jobs (vendor management), and EOR/global workforce offerings.

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

Chapters

Tap a time to open that second in VO

The Impact of COVID on Entrepreneurial Opportunities

0:00 to 0:39

Explore how the COVID pandemic influenced market opportunities and personal business decisions.

“I wouldn't recommend it to anyone to buy a publicly traded company or entities or anything.”

Overview of Business Holdings and Services

0:39 to 1:18

Learn about the diverse companies owned and the services they provide.

“You run five companies right now, personally.”

Expansion into Vendor Management Solutions

1:18 to 2:14

Discover the acquisition of a vendor management solution and its impact on business.

“So just to take a step back, we started in service business entirely.”

Jesse's Entrepreneurial Journey

2:14 to 4:06

Hear about Jesse's background, entrepreneurial spirit, and early ventures.

“There's something where they finally make the jump.”

Scaling through Experience and Partnerships

4:06 to 6:32

Understand how experience with tech companies influenced Jesse's business growth.

“Great thing I think about like working with those tech companies.”

Navigating Acquisitions in a Downturn

6:32 to 9:39

Learn about strategies for acquiring businesses during economic downturns.

“And friends, people I call friends now over the years are all our customers from the same software.”

The Value of Premium Domains for Business Growth

9:39 to 13:40

Explore how acquiring premium domains can enhance brand perception and business success.

“Pending acquisitions, they're in LOI, they're going towards definitive agreements.”

Acquiring Recruiter.com: Insights and Strategies

13:40 to 14:01

Delve into the process of acquiring recruiter.com and the challenges faced.

“And so now when you look at our current revenue, it's mostly ARR.”

The Value of Premium Domain Names

14:01 to 15:10

Learn why premium domain names can significantly enhance brand image and attract enterprise customers.

“But if you went and told your mom or dad, hey, I own Employer.com, I bet they would say, I know of them, even though they didn't exist a month ago.”

Acquiring Recruiter.com: The Story Behind the Deal

15:10 to 19:11

Discover how Jesse Tinsley navigated the acquisition of Recruiter.com and the strategic factors involved.

“So ask me if you don't, don't know, it's not a common knowledge.”
Show all 17 chapters

Revenue Growth and Business Valuation

19:11 to 21:05

Understand the evolution of Jesse's business valuation and revenue growth post-acquisition.

“but all deals that we do within a certain degree of plus or minus on some different terms.”

The Importance of Domain Names in Business Strategy

21:05 to 22:52

Explore how premium domain names can leverage brand credibility and their impact on business success.

“Dude, I don't think people will fully appreciate how hard that is to do.”

Measuring the Impact of Premium Domains

22:52 to 25:01

Learn how premium domains can influence brand legitimacy and customer perception.

“Founders.com, I pay a lot of money for it.”

Creative Deal Structuring for Acquisitions

25:01 to 28:00

Find out how creative deal structures can facilitate the acquisition of valuable assets without large upfront cash payments.

“Yeah, they're using consulting.com, but I think it works for a litany of reasons.”

Creative Financing Strategies for SMBs

28:00 to 31:20

Learn about innovative financing methods for acquiring small businesses.

“So you basically can do a paper LDO, right?”

Unlocking Value in Winding Down Companies

31:20 to 34:40

Discover how to capture value from companies that are shutting down.

“That's why I'm against SBA loans, right?”

Future Opportunities in Infrastructure

34:40 to 35:50

Explore the potential wealth-building opportunities in U.S. infrastructure.

“Yeah, Jesse, my first last name, Jesse Tinsley.”
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Transcript

Automatic transcript. May contain errors.

0:00I wouldn't recommend it to anyone to buy a publicly traded company or entities or anything. I learned a ton, by the way, to talk about jumping into the deep end to your first acquisition. I missed the market opportunity from COVID, for example. I thought there was lots of opportunity to make a lot of money as an entrepreneur that I didn't capitalize on. This downturn was different for me. So when everyone's playing defense and licking their wounds, we went out and played offense. And we've done eight acquisitions in two years and 500 million in pending acquisitions. We also spent 9.2 million to buy f***.com.

0:26And that is a pretty big domain for us. We're pushing like quarter billion valuation, give or take, with revenues exceeding well north of 100 million, 100 % bootstrap, yeah.

0:39You run five companies right now, personally. What's wrong with you? Yeah, something like that. We have a litany of different companies, offhand, recruiter.com, beforeyouapply.com, employer.com. And there's a bunch of products underneath those that basically service a bunch of different things from your payroll, background checks, on-demand recruiting. But it's basically like a full suite of solutions for like enterprise and SMB customers. Anything they need to do for their global workforce solutions, including actually vendor management systems as well, which is also a pretty big vertical for us as well.

1:09But it's less sexy and probably less known than most other products we do. So the five that are under that umbrella, it's outsourced HR solutions, essentially, recruiting. Yeah. So just to take a step back, we started in service business entirely. And then we saw over the last few years, like customer demand for a lot of things that we were already doing, which was like vendor management. We have a lot of relationships with other services companies that did other things. So we ended up buying a vendor management solution called Bounding Jobs. They had raised like a lot of money, Raylock and Excel.

1:41So they're now part of our company, which is really exciting. It's a new announcement. So that'll basically become our employer.com. the VMS. We also spent$9.2 million to buy employer.com. And that is a pretty big domain for us. So you have recruiter.com. You've now just purchased employer.com. You have a vendor management solution that you have as well. That's three. What are the other businesses that you have under the umbrella? Good question. So we have before you apply.com, which gives you like insights to companies before you apply to them, just how it sounds. And that's a little bit better than like looking at last door or other like sites where you're basically looking like the people that are just really upset on the extreme ends of both spectrums either really love working there or whatnot before you apply basically allows you to look at like the actual like managers and how they run those different teams before you actually engage with them in a recruiting process so saves a lot of time and energy so that's one of the one of the solutions we have vendor management system as i alluded to with downing jobs we have eor which is employed like global paying global workers anywhere in the world as well as global contractors and there's a few other products in these there that's the quick short version i'm gonna ask you questions later about recruiter.com and employer.com because those are just freaking amazing domain names to have but first i want to start you were in recruiting for let me look here at my notes coinbase 23andme protocol labs so you you had experience in this space and one of the things that many entrepreneurs face is like they want to become an entrepreneur for a long time.

3:12And then there's a trigger moment. There's something where they finally make the jump. You were working at these tech companies, you probably paid well, maybe had some stock, maybe had some equity. When did you leave and why? To take it back a bit before that, I've always been pretty entrepreneurial. Both my parents are entrepreneurs. Usually with SMB, like small businesses, my dad runs a construction company and my mother ran a small recruiting agency. So I grew up in Silicon Valley and I was surrounded by folks that were really successful entrepreneurs like you know steve wozniak for example i went to school with his kid his son they're like but there's lots of folks like that growing normal being around those folks and so i started my first business when i was first company when i was 18 social like geolocation app in college and then ended up dropping out starting job moms so when i was working at these companies i was actually i had already started my company as a consultancy job moms became recruiter.com and all these things you see today just took it to a different level Great thing I think about like working with those tech companies.

4:09I saw ancient unicorns developed by 23andMe, Coinbase, Stellar Development Foundation, Protocol Labs, all of them. They're really small and same with like scale AI, I don't think it's on there, but it was early there, the largest, you know, fastest, one of the fastest growing AI companies in the world right now. So you get to see how those companies operate, like talent density and everything else in the network. And so now we've brought a lot of those folks that are just amazing operators and even founders into our businesses and scaled those up even further. And we're 100 % bootstrapped. So that's a pretty big outcome for us.

4:38How did you go from, hey, I'm a recruiter at these companies. You've got your side hustle. I'm going to call it a side hustle. It was your business, right? But you're recruiting these companies. You're running, what was the name of it? Job Mobs? Yeah, Job Mobs, M-O-B-Z. Why did you get into tech and keep the business on the side? Well, business was mainly consultancy. So we had lots of consultants out already, myself included, obviously. We basically did like SWOT team type deployments where we'd help companies scale. So we'd go into a Coinbase and help them scale from like 200 to 1 ,000. We did the same thing, you know, Consensus and Box.com and a bunch of others.

5:14And I'd lead those teams. It actually worked out really well, one, like from a learning perspective, but also, I also got equity and other payments from these companies. It's basically a way to boost around. You don't have a technical background at the time. raising money would be very difficult to go build certain things. So it was just a hack to get to some next level. And I think at the time too, I started other software companies that hadn't panned out as well. So it was always been pretty entrepreneurial. I've had plenty of failures. It looks like it's one big success. That's not always the case, as you know, Nick.

5:48It's never that linear. There's always something, no matter who you are. So you founded the original company in 2012 and then you were just working with these other companies to sort of do your SWOT approach where you come in you help them scale to a certain size and then you kind of move on to the next one you're just gathering experience at what is that correct totally yeah I mean but also I wasn't I wasn't I worked at big strapped I've been working as a firefighter on the weekends I worked like two or three days on four days off and I'd be strapped my company that way steady paychecks I was working like a madman for a couple years, like seven days a week, pretty insane hours.

6:26But it worked out, obviously, in hindsight, and a lot of the cash flow and everything else in customer relationships. And friends, people I call friends now over the years are all our customers from the same software. So we built those solutions, bought and built these solutions around customer needs that didn't exist in the market. And so we've been able to grab a really large market share there with some amazing customers like, you know, world-class brands that folks would definitely know quite well, like, you know, HubSpot, Chipotle, customers like that, large customers are. So that's pretty exciting.

6:56Like I couldn't have done that when I was 22 or three to four. 10 years into my career, 35, you know, much easier. So at what point did you start to expand into this mini holdco, if you will, right? So you've got the job mobs. at what point are you like all right first acquisition yeah uh totally so so it's funny you mentioned it like i didn't even know what hold code was like no idea like completely oblivious like didn't care about it didn't even think and then like we're buying cupcakes and i saw people like oh are you doing like they're asking me questions about hold codes and i was like oh it's exactly exactly what it is i guess uh i didn't even know like what uh didn't even know who Andrew Wilkinson was.

7:37Like I knew he was like a designer. I looked at that until like six months ago and I was like, oh wow, anybody at Haltco spaces, right? So it wasn't design. It was kind of just by accident. But to answer your question, we started doing acquisitions. Like I started exploring like paper LBO situations at the end of 2022. So I knew there was a market inflection point like change in early 2022. And in fact, I called it out. It's pretty unpopular on Twitter and with my own internal team. I thought it was crazy. All right. Now's the part of the show where I feel the most uncomfortable, but my therapist says I need to face my fears.

8:09So here we are. I've started a newsletter and I want you to subscribe. And what you're going to get every single week are the aggregated conversations from that week that I have on this podcast with an overview of what their business actually looks like. I'm also going to throw in a review of one or two businesses that are listed for sale. I'll give you my opinion on whether or not the EBITDA multiple is good, or there's customer concentration, or there's red flags or green flags. And then lastly, I'm going to give you one piece of actionable advice every single week on how to buy your first business.

8:36So click the link below, subscribe to my newsletter, and let's get back into the show. But we sat on a bunch of cash, didn't raise pay. Like we basically knew there was some storm coming based on like, we have a ton of data right around jobs and also hiring. So when it goes down and job postings go down, I can, I can see a linear trend of what's going to happen before anyone else. So that combined, like combined with previous like downturn experience i basically pulled the plug on spend and we sat on cash so basically by the end of 2022 i knew i was going to do something with i thought the market opportunity from like covet for example i had missed i thought there was lots of opportunity to make a lot of money as an entrepreneur um that i didn't capitalize on that you could have uh during that time frame um and i didn't want to make sure that this downturn was different for me that i would go capitalize So when everyone's playing defense and licking their wounds, we went out and played offense and done eight acquisitions in two years.

9:31Jeez, man. We've got 500 million in pending acquisitions right now. 500 million in pending acquisitions? Pending acquisitions, they're in LOI, they're going towards definitive agreements. That is what's happening, yeah. Are you still a firefighter too? I'm definitely not a firefighter. At home, I'm the CEO and firefighter at work virtually and at home, rounding up kids, but not anymore, unfortunately. It's a lot of fun. You've got job mobs, 2020. Give me an idea before you started sitting on cash. What was the size of the company? How many employees did you have? Can you give me top-line revenue?

10:08Within my best without pulling up the actual data. I think it's like 2022 we're doing, we probably would have finished the year around 7 million, 8 million. Something in that range, I guess. You're good size. I mean, for a services business, that's freaking actually hard when you're in that like. Like 40 people, 50 people, something like 50 people is my guess. So you make the decision. All right, I'm going to start sitting on some cash, which was very smart. job mobs ends up becoming recruiter.com was recruiter.com the first acquisition that you made yeah it's pretty crazy too the story there they're a public company so this isn't like some trivial acquisition for your first one that you'd have to be insane i wouldn't recommend it to anyone to do hence to uh to buy a publicly traded company or entities or anything i learned a ton by the way like to talk about jumping into the deep end to your first acquisition so we did the first acquisition that was mainly just carving out their their services business that was the first one that's at least public.

11:11We did some other smaller acquisitions. They're like just acqui-hiring kind of things. But we did that in March of 23. And then we closed a bigger deal with them in August of 2023, which basically take a lot of the grand assets around recruiter.com private. And that took us a year and a half to close, I think. I just closed this last August. What happened? Why were they in trouble? What changed for them? I don't know their internal circumstances. I don't want to speak to those particularly. But I do know that like a lot of businesses, I'm talking generally here, like across the entire HR tech space have been caught off guard with like the macro trend going from like an insane uptrend rate of like hiring in 2021, 2022, like the best it's ever been to the worst it's ever been.

11:54Like I had a CEO mentioned like this week, they mentioned that like this is worth 07, 08, 09, you know, they're around then. And like, this is a worse downturn for tech hiring, at least than it was then. And so that gives you an idea of the landscape, how quickly things shifted. And so I think a lot of companies, even, you know, we've acquired good companies. We have a few others, obviously pending, as I mentioned, but we've made a bunch of other offers. I've talked to hundreds of companies in the last two years and every one of them, except for us, is basically declining in revenue. Like the revenue is going down, customers are churning and just kind of leading, you know, death by a thousand cuts.

12:29And so it's not that founders are doing anything wrong or if the companies are doing anything wrong. It's just simply a macroeconomic trend. Recruiter.com, were they doing what you're doing? Were they a competitor to you or were they doing something totally different and you just repurposed the brand into what you do now? At the time, yeah, they're definitely doing something similar. That's why we acquired some of their services businesses that we're doing, recruiting as a service. And they're really good, you know, trapped, really beautiful brand, millions of followers on social media, the largest LinkedIn in the world.

13:04It's a beautiful, beautiful company. And so one of the first groups I joined on LinkedIn. So really good, like legacy brand and everything else. And that kind of unlocked everything. So if I'm a small business owner, let's say like talking to your audience, like folks that are building companies, I think the biggest thing that that unlocked for us and allowed us to go do all of these other acquisitions because the brand and image of that made us look a lot bigger. Right. We're only doing 7 million. And we're doing a lot more revenue now. But the point being is that at the time we were relatively small.

13:32Yeah, we had cash. We're sitting on cash. We had good margins. But it allowed it and locked all these other things that we've done to date. It made a huge impact. And so now when you look at our current revenue, it's mostly ARR. And we're able to go punch way above our weight. And I think that's just a big thing. So if I was to spend money as an entrepreneur, I would go buy an employer.com or recruiter.com as early as possible and get that brand and that image. Employer.com, for example, before we bought it, didn't exist. But if you went and told your mom or dad, hey, I own Employer.com, I bet they would say, I know of them, even though they didn't exist a month ago.

14:10And that's the point. You spend the money because you get the image, right? Big brand. And that's worth, you know, that's an enterprise customer. You might spend a half a million, a million, two million bucks on it. Obviously, it's hard to get that cash. But let's say you have it. that that return the roi on that is huge you might get an enterprise customer because you half a million dollars a year and for me that's worth every every single dollar 2022 you're sitting on cash you're seven million dollar company and you end up acquiring recruiter.com how did they're publicly traded how did you even get in the room with them how did you even know that they were for sale like how did you even finance it or afford to purchase them like there are just so many questions that come up for me because you know i'm a small business owner i I would never be able to go to like, I don't know, fashion.com and be like, Hey, could I purchase you?

14:54How did that whole story happen? Yeah. So there's many facets, like parts to it. My best like reconstruction of it is we won like an award for like top RPO companies, HRO today at the end of 2022, which is like big in our, our niche vertical. What's RPO? I don't know what that means. Sorry. Yes. Yeah. I'm using jargon. So ask me if you don't, don't know, it's not a common knowledge. Recruitment process outsourcing. like that SWAT team building out of companies, long-term or short-term. And so that kind of got us on the map. I'd already met with those folks previously, and they had had some other like paths forward they were looking at, and I kind of talked about maybe, you know, but I met them and we'd had conversations to try to get something done, like a partnership or something similar previously to March, 2023.

15:41And they had some other things they were exploring. And so we just got to the right place at the right time, right? The whole market came down and all basically, I think our internal framework for the last two years is we pretty much are the market. So every founder you talk to when you're doing M &A will say they have another offer. Right now, that is maybe true, but not in the sense that you think. It's all really like there is no one else making fair offers. As an outsider, I'm like, all right, you're a$7 million company. They're publicly traded. Now, there are lots of publicly traded companies whose market cap is not$7 million, right?

16:15They're micro caps and they're, you know, they're very small, but it just has the air of, oh, they're, they're much bigger. Recruiter recruiting.com is much bigger than, than Jesse's company. Right. Why not go to indeed or glass door or monster or any, any other job servicing company and sell to like a larger brand like that? Like, how did you even get to the space where they weren't even entertaining other offers? All of a sudden you're talking to them. Were they a lot bigger than you or were they just not as big as everyone thought and they went public to have a liquidity event for the people who founded it?

16:50I have no idea about the reasons for going public. But I can tell you why we've been in a lot of acquisition deals empirically compared to Indeed or Glassdoor, which are lots of friends at both companies. Good companies, just to clarify. And I think this is true of all large strategics. They move really slow. I think sort of like when you have a big financial turn and a lot of companies were over 21, 22, and this is not specific to recruiter.com, just general statements. They were basically like earning a dollar to earn 50 cents across companies, right? Because growth at all costs was what the market was rewarding across both the private and public sector for these companies of all types.

17:33And so I think that when that turned in, let's say, early 2023, early 2022, a lot of folks were caught off guard. And so what's happened is now you have a secular decline. So like the Indeeds and Glassdoors in the world aren't buying companies. They're going to move really slow, especially when they have decreasing cash flows on their cash sheet, right? And increasing burn, decreasing revenue. I talk about Glassdoor and Indeed, right? like our revenue goes flat right so it's basically it creates a thing a situation where like those companies aren't acquiring if they are it's going to take six months and so what we've done a really good job it's like we'll pay like we tell founders why we close a lot of deals we'll close in 30 days we're going to make you know certain things like stringent on terms so that we don't get screwed since we're moving so quickly but like that's the the difference is like one if we we've never done a deal where we've told somebody hey we're going to do x y and z or give me this price and backed out so it's a reputational thing and then two there's no like that's the big thing with like pe right you're going to get retraded on it's almost 90 guaranteed the end of whatever process they put you through and after you spent a quarter million dollars on lawyers finance folks they're going to say hey by the way nick this is your real offer take it or leave it that's after you've told all your friends family so that's just it's not a good experience you've thought about from sales process so what i do is i try to educate founders and say hey this is what it is this is what we're play.

18:59This is why they're doing it. And this is what they're going to give you. And most of the time I'm right. And even the founders that do go with the private equity offer usually come back to us and say, you know what, if you're still interested, we'll buy. And that's kind of the secret sauce of how we do deals and why we win deals, not specific to just recruiter.com, but all deals that we do within a certain degree of plus or minus on some different terms. Can you, can you give me an idea how big was the recruiter.com deal? How big? I mean, well, I think the bigger piece, like they have 10 % of our cap table for shares.

19:29So it's a pretty, like basically for being bootstrapped, it's pretty significant. They still up the trade, I think on the secondary market. So I don't want to share anything, but I think that that is a pretty valuable outcome for them, honestly. So like if you compare it to our valuation today, I think it's a well into the eight figures deal in my opinion. That's a sophisticated transaction, man. like definitely we didn't cash we i think the big thing too like we paid 1.8 million dollars like clothes and we paid some other some stuff along the way as well so it's like it wasn't it's multifaceted very sophisticated and in complex i'd say because of the other the time it takes right just to get like nothing to do with us because we're private but like taking buying anything that large or taking that much of an asset from a pub co you have all the regulators and everything else that need to approve all of that.

20:19And so it just takes a very long time. Wouldn't be my first choice if I was doing acquisition again, in terms of like the speed at which I move. Being moved in, it's much slower, but a good outcome, I think, for everyone, all things considered at the end of the day on all sides. Okay. So where you were$7 million sitting in 2022, can you give me an idea of size and scale of your companies now? Quarter billion valuation, give or take, with revenues exceeding pretty large number. I don't want to say the exact revenue number yet because it's depending on when this is even released, honestly. But I think I'm happy to share some of the retweets or whatever of this.

20:57I can put the updated one, but it's going to be a lot. We'll be pushing well north of$100 million revenue this year. And that's only 99 % SaaS. And that's all bootstrap? 100 % bootstrap, yeah. Dude, I don't think people will fully appreciate how hard that is to do. so that's pretty yeah great to say especially going from services pivoting like 100 % in two sas is like nearly impossibility I don't think I can replicate it myself I tell I joke with my team all the time on the day if I just if I just quit tomorrow not that I am but like and just try to replicate what we've done couldn't do it would take me a long it would take me a while even with money right even with like resourcing and networking it would be very uphill battle to get everything put do you do you feel like that strategy that you had which was or the thesis that you've had, which is like, all right, premium domain names, recruiter.com, employer.com.

21:46So I'll give you an example. Chris, my business partner and I own cofounders.com. It's not, it's not recruiter.com, right? But it's cofounders.com. And we, at the time I paid for it $65 ,000. And I was like, I don't know, should I, should I pull the trigger? And looking back, I'll pay you set. I'll pay you at least a hundred right now. So if you, right now, I can be a hundred grand for it. 120, you can do 130. You can double your money. I'll even give you some equity in my name. Oh, okay. All right. You can do this right now live on the podcast, Nick. It's just totally good script. So it's great.

22:19This podcast is just turning into Shark Tank. Just Sharks. Today, I am seeking a... But you would think, yes, that strategy, premium domain names, has absolutely paid off for you? Yeah, definitely. I would. Yeah, definitely. Definitely do it again. I think with any business, I would buy or start or do. In fact, there's some cool folks I've met that do brokering of it. And so I'm always looking at domains, depending on what we're doing. We're looking at some others right now for different verticals we're going after. So definitely be announced in the next probably six to 12 months for another premium.

22:52Founders.com, I pay a lot of money for it. A lot. Maybe a million. Yeah, founders.com. Yeah. Not saying co-founders is like, it's good. It's very good. I'm stoked that we got co-founders for$65 ,000. I think it's a great bet. If I can get founders.com for 65 grand, freaking sign me up. Recruiter.com is at least an eight figure domain name. Then you've got employer.com freaking$9.2 million that you bought for it. Do you have a domain sickness like my business partner, Chris Kerner does? Because legitimately we pay, we spend, we spend like five grand a year just on registering the domains that he has that we don't even use.

23:33I have, I have probably a hundred domains, um, but definitely not like five grand worth a year. I think it's like, what was that? A hundred times 12 bucks or something like 1200 bucks. So something like that. He's got me beat by a couple hundred domains. It sounds like, but yeah, a lot of it's a mix, a mix of things. Like I own recruiting and HR.com as well, like just things that would make sense. Right. So like, you know, you know, things that tie into our industry. So in all the other like ancillary ones, like, you know, you know,.NETs,.cos, all those main domains were focused on. Okay. Do you recoil as badly as I do or Chris does at a.NET versus a.com?

24:16Yeah, it's just not the same. It's not the same, right? I wouldn't pay a ton of money for that. And you know, like basically like also think about your ideal customer profile too, like what you're doing. like how like I would I would suggest like it is somewhat subjective most of my customers are you know 40 to 60 years old and you know chenly.com is going to like domain name is going to be really relevant to those folks and so like but if I was selling to like and it'd be very different right I'd probably go with social media like in more presence there as opposed to like um traditional like web web sales for like enterprise so I think like it really depends on your your ideal customer profile.

24:53So I wouldn't say cart block. Overarching statement of that. I think it gives you brand authority, too, even if you're selling a course or something. Who's the guy that's selling? What was it? Courses.com? I forget his name. Anyways, it doesn't matter. Don't even give him a block. But yeah, was it Consulting.com? The Consulting.com guy. Yeah, that's ringing a vague bell. Yeah, they're using consulting.com, but I think it works for a litany of reasons. Have you been able to measure like the return on these premium domains? Like obviously there's a brand component to it of, Hey, I own recruiter.com, right?

25:31Oh wow. Jesse must be legit. Right. But for you, I don't know, is there a way you can measure, Oh, this is how many searches employer.com was getting per month. And now I'm able to convert all of that traffic because it was what didn't exist before. And it exists now? Like, do you look at it like that? Or is it more of a, no, it establishes me, it gives me credibility. And now off of that credibility, I'm able to build. The answer is definitely, we've done a bunch of stuff. I think the simple way to put it, and this has probably like never been done. We have an infinite IRR. And so the reason is we've bought all of these deals in the structure of which we put none of our own capital at risk for many of these deals, in my opinion, where IRR is literally infinite.

26:13So that's how good deals we've done like our, in my opinion. So that makes it pretty much a no lose situation from our perspective, but would make Berkshire jealous in their original day. So this is my last question that we can riff on. Many people will look at these premium domain names and might have the strategy of like, Oh yeah, I need recruiter.com. Whatever the price is, I'll pay it and I'll go raise a fund and I'll pay for it. But in hearing you describe the way that you've purchased these, there's creative deal structuring? How do you think about that? Obviously, you want the domain, but also you're still being creative with it.

Read the full transcript

26:49What recommendations do you give to people who are trying not just replicate your exact strategy, but replicate the strategy of go big, buy the big assets, but don't necessarily come out of pocket a ton of cash? In our... What applies for us might not apply to others, but I think the general overarching thing is we get pretty creative with deal structuring. So let's just say that I'm buying your business nick and let's say it does a million a bit right it's just simple simple service business let's say and you know let's say we settle on like forex right forex for whatever the business is let's say well you can do like let's say you have operating like cap like working capital needs right a million dollars let's say that's flowing through the business so now i can go i can raise debt attached to the business in a lot of cases assuming at some scale right obviously been pretty vocal about not liking s sba loans for the personal and like liability of it very very vocal and against it online because i think that it is not great but unless i'm pissed i just found that out 30 minutes into our conversations because i would freaking love to debate you on that one but keep going yeah yeah so so i can just remember right my car plan statement for that is infinite iron that's all i would say so um

28:07So you basically can do a paper LDO, right? So you basically do a founder like note on that, right? So like it's simple structures, hey, we're gonna roll a million equity, a million seller note, and we're going to give you like an in or now of$2 million. Like that'd be a simple structure, like a very basic one. Yeah. Obviously you're like, okay, well, there's no cash flow in theory, but you should be having working capital that's flowing through the business, making like a lot of cash. So I think deals like that in this SMB space exist everywhere. Boomers wanting to retire. To give you some statistics here, it's like really interesting data.

28:41I nerd out about this stuff. I read 10ks. I look at data reports for this stuff all the time. The big thing is that what it's like 90 % of businesses fail in the first 10 years. Of those businesses, only like only 20 % of them end up selling. So like even if you survive 10 years as a business, only a small subset of them actually sell. That means that like, out of the companies that make it 10 years, the very small select few, only one in five are actually selling, which means the other four out of the spot, they're just shutting down. And so I wanted to go, like I've told a lot of my friends and family, I'm like, look, I would just go buy a bunch of like local businesses, roll up two or three of them, do all seller financing.

29:20There's a bunch of older generation like boomers that want to wind down their business and they're just going to shut it down. All those customers are gone. like you can basically go get seller financing and earn out and maybe some rolled equity and you can just buy these businesses literally for zero down that's it like that you could do that all over the all over the country like everywhere i can do that like in my blindfolded like it's there for everyone that's listening to this if you structure it correctly and you keep your deal costs down for lawyers and accountants so so two comments on that first one is any business that i bought That was over$100 ,000 transaction price.

29:56I have never paid all cash down or financed everything. There has always been a seller note, something forgivable, something rolled, some creative portion of equity in the deal structure. So any deal over$100 ,000 has always, for me, had a component of a seller note or something creative involved. smaller deals than that just to get it done quickly and like not have the headache i've paid cash but most of the time oh not most of the time every time over a hundred thousand dollars there's something creative but the second piece is chris and i just we recorded a podcast this morning and we were talking about this have you ever heard of pros closet they were the chris likened it to like car max except for road bikes like you know the guys who were in the spandex and riding the bikes on the road.

30:47Yeah, those type of bikes. So it's like a resale market. And they went out of business. They raised a bunch of money and they went out of business. And he reached out to the CEO and was like, hey, I saw you guys shut down. I'd like to buy your email list. And he was like, oh, we just agreed to terms and we just sold that to somebody else. But it's something like people don't even think about. Hey, what's happening to that customer list? What's happening to the IP? What's happening to whatever other assets you have? They're not thinking creatively. They're thinking, oh, I got to pay all cash or I just got to come in top dollar.

31:15And I love that structure that you just laid out. That's a great way to start if you don't have money. That's why I'm against SBA loans, right? So if you want to debate this, I would start there. And then if you move up and you have a track record and you feel confident making bets, it should be ace, menstrual upside, and you should feel very confident about taking money against your own personal liability to then grow that business or businesses that you're buying. So it's a much safer way to start, I think. And I think with your point, because we've done this, there's a lot of companies that are just winding down and there's tons of IP and assets there that you could go buy for very friendly deals right now, especially that companies that just shut down.

31:59To your point, we've done this a few times that are like a deals we don't even announce, but we'll just buy up a code base, customer list, whatever it is, and you can get stuff. And also like there's, there's actually auction houses for this too. So like the other piece that people don't, most people aren't aware of is that like BCs and private equity firms will have a lot of auctions of companies that are winding down and you could buy up ARR. Like there's a company that's doing like 150K ARR. We could have bought it for 200K, like 200K, 200K. So it's just, it's literally a 100 % cash on cash return.

32:28I'd probably run it with no, no bull. I didn't have the bandwidth to do it because we're doing larger deals. So it's not worth like the one like trade off is that it takes just as long to do a small deal. large deal literally the same says it doesn't change anything so it's sometimes actually harder on the smaller deals for a variety of reasons mainly educating the founders on the terms but those deals are literally everywhere right now and so like across every single vertical yeah so when you're you just described tech deals and i know you said this earlier but those types of deals are all over the country like they don't have to be tech deals they could be the local electrician that just shut down they could be the local pizza company they could like whoever it is that just shut down, they've got a customer list.

33:09They've got a history of people who have come in and out of their business over a period of time. You can go and approach them and say, what are you doing with that list? I'd love to have it. There is value there to be captured if you're being proactive on it. So like, I wouldn't listen to this and think like, oh, that's unattainable. Jesse's talking to PE and venture capitalists. No, another nugget. Like one of the things that one of the roles I'm going to be working on the next year or two is all like construction rollups for commercial construction and build outs like electrical grid stuff, mainly to do government contracting work.

33:39But basically there's a bunch of like, there's a lack of general labor like happening in the construction industry, right? There's a huge like surplus demand, right? Building our old infrastructure. So it's not just that this applies to this applies to every single industry in America, right? To your point, your local pool companies to pool cleaning companies to bug spraying companies, whoever, all of it is relevant. So, well, I, I, I love, I love that approach that even though you have money, you're not being lazy with it. And you're not like, oh, cool, good deal. Okay, here's cash. Oh, cool.

34:12Yeah, we'll pay it. You know what? Oh, you want 1 million? We'll pay you 1.2 and we'll close quickly. Like you're still being stringent with how you purchase these things and creative and having them roll some seller equity like that. I just admire that so much because it is so easy once you have a win or once you have some cash to kind of, okay, we can be a little flexible here and get out and get over your skis. So kudos to you for that. Here's the last question. Well, before I ask the last question, where's the best place for people to come find you, Jesse? Yeah, Jesse, my first last name, Jesse Tinsley.

34:43It's on Twitter or LinkedIn. I'm just there the most and generally pretty active. So I'd love to connect with you. So here's my last question. Let's say outside of recruiting, if you were starting over and maybe you're not even in Silicon Valley, what space are you the most excited about? or where would you go to start your wealth building life 10 years ago? Today, it's actually what I'm partially working on with some of these roll-ups. It's all things rebuilding like U.S. infrastructure in electrical systems. That's something that's going to be completely redone in the next 10, 20 years, not only for like AGI and AI, but because of new power systems.

35:25So I think anything that touches that is going to be a massive opportunity, whether it be the tech, the construction, the supplies, the materials, anything such as that supply chain is going to be a multi-trillion dollar opportunity over the next 20 years. So I think that is a absolute gold mine if I was just to even be like the concrete supply company. Like that would be a big opportunity. That's where I would start, honestly.

From the publisher

MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribe


Join me, Nik (https://x.com/CoFoundersNik), as I interview Jesse (https://x.com/JesseTinsley). This week, I sit down with Jesse, a true operator who turned his small consultancy, Job Mobs, into a massive, 100% bootstrapped holding company.

We dive deep into his aggressive strategy of acquiring eight companies in two years, playing offense when the market was down in late 2022.

Jesse reveals how he scaled from a $7 million services business, to a projected $100+ million SaaS operation. He shares the unconventional tactics used to acquire a publicly traded company (recruiter.com) and why buying premium domain names like employer.com is the secret hack to gaining instant brand credibility.

Critically, we break down how he uses creative deal structuring (including paper LBOs) to achieve what he calls infinite IRR.


Questions This Episode Answers:

1. How can you use a market downturn to aggressively acquire competitor businesses?

2. How does a premium domain name provide instant brand authority and ROI?

3. How is it possible to achieve infinite IRR when buying a business?

4. What creative financing methods (like a seller note) allow you to buy businesses with zero cash down?

5. Where are the best non-tech opportunities for business roll-ups across the country?

Enjoy the conversation!

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Love it or hate it, I'd love your feedback.

Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.

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This week we covered:

00:00 Highlights_Navigating Acquisitions in a Downturn

02:54 Building a Diverse Business Portfolio

06:11 From Employee to Entrepreneur: The Journey

09:00 Strategic Acquisitions: Lessons Learned

12:09 The Impact of Branding and Domain Names

14:59 Creative Deal Structuring for Success

17:47 Opportunities in a Shifting Market

20:55 Future Trends in Infrastructure and Technology

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