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Episode

Never Outsource Your Sales: Nate Wright on Exit Valuation

With Nate Wright/April 22, 2026/55:14 listen/Hosted by Jordan Lally

Nate Wright runs The B2B Bandits, a B2B sales and marketing operation he describes as sitting closer to the sales team than the marketing team. He has spent over 20 years in the space, worked behind the scenes with close to 50 agencies, ghostwritten books, and collaborated with names like Mailshake and Oren Klaff. The conversation covers what he has learned watching agencies grow, fail, and get bought and sold.

A large part of the discussion focuses on the shift in how buyers behave. Nate has observed that reputation and depth of experience factor into purchasing decisions less than they used to, which creates an opening for cheaper or faster competitors to win deals they probably cannot deliver on. He traces a pattern across close to a thousand clients: most found him after they had already been burned by someone else.

The argument Nate makes about outsourcing is the sharpest thing in the episode. He treats lead generation as one of the three core pillars of any business, and says handing it to an outside agency is the kind of thing a buyer spots immediately during due diligence. It weakens the exit case, sometimes decisively. The final few minutes turn personal, and his answer to what he would tell his earlier self is not a business tactic.


What You Will Take Away


About the Guest

Founder, The B2B Bandits
Nate Wright

Nate Wright runs The B2B Bandits, a B2B sales and marketing operation focused on outbound channels including cold email, newsletters, and LinkedIn. He has spent over 20 years in B2B sales and marketing, worked as a consultant and white-label partner for close to 50 agencies, and has been involved in agency mergers and acquisitions. He has also ghostwritten books and collaborated with organizations including Mailshake.


Full Transcript

Full transcript of the conversation, published verbatim. Speaker labels come from the recording itself, not from an automated guess.

Jordan:0:00
Welcome back to the [High Ticket AI Systems] podcast. Everyone please welcome the winner. Now, the Mr. Nate, right, Nate, how you doing today, my friend.

Nate Wright:0:08
I'm doing.

Jordan:0:10
Well, it's a pleasure to have you on. I know when you and I first spoke, you have worked with some pretty big names in the high ticket industry or even marketing in general. So can you please tell me and even the people listening and what you do at a very high level?

Nate Wright:0:26
I support B2B sales teams. So via combo of digital and non-digital marketing and sales. I would say that on the spectrum closer to the sales team than I to the marketing team.

Jordan:0:46
Why do you feel like that is?

Why would you categorize yourself there opposed to traditional marketing?

Nate Wright:0:55
Well, in the B2B space, marketing without sales is kind of dumb. Yeah. It's like, you need to be spending X amount on your marketing span. Like really? Who ever told you that? Like some of the most successful people and companies I've ever worked with didn't have great marketing, but what they did use was all there to weaponize the sales team.

Jordan:0:59
Thank

Nate Wright:1:17
It was always more ammunition. It was less about marketing for the sake of marketing. Now, over the years, I have come to value brand awareness a lot higher, but again, just to support sales. So being more targeted and deliberate about where the awareness needs to peak.

Jordan:1:42
If I were to mention the name Jeremy Haynes, would that name mean anything to you?

Nate Wright:1:48
It's vaguely familiar, but gun to the head, I can't tell you what it is. Yeah.

Jordan:1:52
That's okay. He has taken over, internet marketing. wouldn't say taken over, but grown very rapidly and the internet marketing space. What he drives, for marketing is exactly your philosophy as well. He cannot separate. He w he literally feels guilty separating sales and marketing. It's like, which one's more important? Sales or marketing? It's like, can't do, I can't. It's like, they're both fucking right there.

Nate Wright:1:58
Mm-hmm.

Nate Wright:2:03
Yeah.

Jordan:2:21
You cannot have without the other, you know? And he says really good marketing, and I completely agree with this, really good marketing can make up for a shitty sales team.

Nate Wright:2:21
right?

Nate Wright:2:34
Hmm.

Jordan:2:36
It's obviously great to have both, but if you're like sales team can't communicate effectively, can't maintain posture in the clothes, whatever the case is, but your marketing does all of the selling for you on the front end makes a sales team job.

Nate Wright:2:52
So I would totally disagree that actually. Yeah, no. So yes, good marketing could heal some wounds. It can. It can. Self-sealing, know, like the stuff you put in your tires, it's like foam.

Jordan:3:05
Ha ha.

Nate Wright:3:13
Then you pop your tire again, especially I used to put it in bike tires when I was growing up and it would just heal but like over time it creates other problems. I think that good marketing that actually builds an established brand and business that people recognize that has name recognition like In the software space like the Apollo's over the world. Everyone knows what Apollo is, right?

When you get to that point, I think the work the marketing did to get at that space on the shelf absolutely could overcome crappy sales. But I don't think that advice applies to people that are trying to work their way up to that top shelf. I mean, I've lost, I mean, I've lost my position as like a middle or top shelf brand because I, I. let my marketing slide over the years. So I still have a great sample of clients and doing great work, but I've found I've had to actually sell harder to overcome losing that spot. It's not a ranking thing, but I think it's more of a,

Jordan:4:24
Well that's

Nate Wright:4:30
I think in especially in arenas that are commoditized, like, well, I mentioned Apollo. So data, cold email, and a high ticket space, would look at CRMs. It's highly commoditized. It's not, that's kind of the cool thing about high ticket is that you could actually get away with. doing like value-based pricing a lot easier than you can with something that's become commoditized. And I would say that cold email systems building has become commoditized, but the writing of cold emails has not. But I think it's around the corner. I think we're close.

Jordan:5:12
Yes, yes. Well, two things. One is, well, that was kind of my point when you said when your marketing kind of took a, I don't know, what's my back burner? You had to sell hard. And I was like, yeah, like that's why marketing can outbeat sales sometimes, right?

Nate Wright:5:28
Yeah, the reason I think that it's dangerous advice. This is something I've been kind of, since we last talked, I've been kind of obsessing about this idea of dangerous advice.

Timing is so important. And oftentimes you'll see companies blow, especially after a round of funding, they'll blow a lot of money to get that awareness and to get the word out, to become thought leaders if it's something more executive or get their brand press. So they're putting like real dollars behind this. But when they're on the way up there,

Jordan:5:45
and welcome.

Nate Wright:6:12
The sales team, would say, is even more needed. That ability to sell is even more necessary. Also, what I find happening is that the salespeople in the trenches, if there's not a really, really good feedback loop to let the marketing team course correct, it could become very, very dangerous. That's why I love the role of a chief growth officer. I am...

Jordan:6:29
Mmm

Nate Wright:6:40
I'm so happy that that's like become an established thing now. Because that's basically what I've been doing with my own company and most of my clients for years. I just didn't have a name before.

Jordan:6:52
On that topic of feedback loop, yes, yes, yes, 1 million percent yes. If your sales team can properly submit end of day reports about what's happening on the sales calls, what objections are you getting? How are they coming through frame? Are they cold as ice or do they watch a couple of videos, read a couple emails and come through better frame? If you can have your sales team articulate this every single night, like you said, and correlate that to the freaking marketing team, now you can...

Nate Wright:7:05
Yeah.

Jordan:7:22
Create better marketing. So these prospects are coming through so much better frame. You can answer the objection of they come up It's just yes, we'll completely agree

Nate Wright:7:31
One of the things I've also learned recently, just with hard, hard anecdotal evidence of real data within my own business and looking at my clients' businesses and my recent clients' businesses, it used to be that, like say in the software space, that you could get in the top five on G2. and do all right. As an agency, you could get in the top three on clutch and do all right. Upwork, you know, if you had the top rated plus badge, you'd be good to go. But one of the things I'm noticing in buying habits right now is reputation and depth of experience matters less. I couldn't tell you why, to be honest. I would love to have a good answer to that question.

Why the shift? Because it seems irrational, but worries other than when tell us sometimes the opposite of a good idea is another good idea. if depth of experience and having hella reviews doesn't factor into the equation as much anymore, what does? What took its place? Price? Vibe? I don't know.

Jordan:8:56
Yeah, that is a pretty good question. guess for me specifically, I've owned an agency for six months now. What I sold initially is not what I sell today. What I've been selling for the last 18 months, we can say that's newer. Do I have hell of like reviews on Clutch or G2? No. Do I have case studies? Yes. But...

Nate Wright:9:11
Yeah.

Jordan:9:24
Getting back to your point of experience and reviews, et cetera. mean, 18 years realistically is still considered a new business. I think what helps me and I only can speak from my experience is the method, the mechanism of what we are doing. Maybe I'm lacking information from what you said to kind of correlate the two, but what I think really helps me in my marketing and my sales processes is our

Nate Wright:9:38
Yeah.

Jordan:9:54
the differentiator, right? Going back to the mechanism of how we do things. Are there other people that sell similar things? Sure. The level that we do it, honestly, no. I have yet to find another company that is exactly what we do as well as the speed of execution, the quality of work, et cetera. So does that kind of come into play with what you're describing right here, Nate?

Nate Wright:10:07
Mm-hmm.

Nate Wright:10:17
Yeah, I mean, you mentioned speed. And that is something that when I've had the opportunity to find out why I didn't win a deal, or why I didn't get a meeting when it was like in the bag, like ready to go, like why something fell apart. The two things that I've seen come up as price, and I mentioned commoditization. And so in my world, you know, the B2B world, cold email, newsletters, LinkedIn outreach, LinkedIn ads. Those are the primaries, right? There's a few of their odds and ends. You can bolt onto that, but those are the primary channels that we're working in. some of them have become commoditized and some of them have not. So when you're actually putting together pricing that you need A and B.

Jordan:10:54
official.

Nate Wright:11:11
Sometimes that doesn't come through that well when you've got it almost seems like they don't even belong in the same pitch even though that prospect needs both and they needs them to work together as a system not as not as a duct tape together mishmash Right? The other thing is speed. You mentioned speed as being one of the things. We're really, really fast, but I have lost deals in the cold email infrastructure space selling cold email infrastructure. It was like, yeah, another, another vendor said they could get this launched in a week. And I'm like, well, warming, you can't speed up warming of a domain.

Jordan:11:27
Absolutely.

Jordan:11:43
But like through

Nate Wright:11:47
Sorry, you just can't. That's it's old, old ass technology and there's very real limitations on it. But someone lying won the deal and I bet you they'll be able to keep it too. Because even if they fall short a little bit, if they're able to buy time for a few weeks, they'll end up getting that fee, that retainer, that deposit, not me.

So I think that there are some, and that's always been the case. That's always been the case that, you know, someone could over promise, but that's where I think the review, the background, the reputation, what your reputation is in the space, you still like factor into the equation differently. And now people will hire a stranger with very little public reputation that says they could do something faster. or cheaper or both. Even though in reality they probably can't. So oftentimes most of our clients, and this is a real number, we went back through. close to a thousand clients over the years who were going back through it and like, whatever happened to these people. And some of it was because I did a shitty job. I over-promised. Some of it was me not understanding the target market and the prospects. Some of it was just a bad product and a bad vertical. Some of it was bad luck. But looking back at everything, most of those companies found us after they'd been burned. Not before.

Jordan:13:22
Mm-hmm.

Nate Wright:13:23
And that's where marketing to your earlier point where I think that smart marketing gives you a chance to get there first. And it's not just speed to lead. It's just like, well, obviously we're going to call blank brand first, just to at least develop a baseline. That makes sense, right? If you're getting an oil change, yeah, we'll check Jiffy Lube first. And they've done the hard work to have that instant recognition. If you think about Coleemah, you think about Well, at the top three, Like Apollo used to be male shaken, yes, where now it's Apollo smartly instantly, right? But they spent the time building that name recognition and then anyone competing has very few levers to pull to even make a difference. It doesn't even matter anymore.

Jordan:14:14
Right, right, yeah, and something in Smart Leader.

Nate Wright:14:15
That's why I think it's dangerous advice because most people, there's a logical fallacy or a bias about this. forget what it's called. They overestimate their own ability. They overestimate their own luck. They overestimate their own status. I'm guilty of this all the time.

Especially after losing a deal. It's like, those blankety blankety blanks, like they have no idea what they're missing out on. And I feel like a jilted lover or something. Or I got like stood up on a date in college and like had a meltdown afterwards, which I have. But it's the same exact psychology, right?

So anyways, I went about four different directions on that question there, but.

Jordan:15:02
You're totally good. And it allows me to pick and choose where I want to take things. And where I want to take things is green or newer buyers versus experienced buyers. I think because you and I are pretty educated in this space, hats off to you. You're probably more educated than I. But that does not change the fact that I still think you and I can both agree with what I'm going to say right now.

Nate Wright:15:17
Mm-hmm.

Jordan:15:27
When a newer, greener buyer is on your sales consultation and you kind of explain how things work and kind of explain why you do it that way, and they don't really care about why you do it that way, they kind of just want the bottom line. So they're going to go to the cheapest person. They're going to go with the guy that says, we can get your cold emails up in a week and it's going to cost, I don't know, a third of the typical market rates. And to a brand new buyer that's brand new in this space,

Nate Wright:15:39
Yeah. Yeah.

Jordan:15:57
Hell yeah, that sounds awesome. Nate, Jordan, your prices are whack. I'm not gonna go with

Nate Wright:16:02
Whack. Yeah.

Jordan:16:03
And then when you go with a guy who's been around for a few years, he's tried a couple of agencies and he asks you, so do you guys have any DNS settings set up for your cold email? Or how long do you guys take to work with your cold email processes? How many words are you guys saying in your cold emails? They just ask much better questions. You can tell this person's been around the block, right? I like those guys, I do.

Nate Wright:16:26
Mm-hmm.

Jordan:16:29
Because for one, they're just more educated. So it makes my job a little bit easier. I can just articulate myself a lot better. But, secondly,

Nate Wright:16:37
Mm-hmm.

Jordan:16:39
I don't know if I have a second thing, but you can win those deals better because the guy who's newer, who's greater, right? You tell them what the price is and he's like, that's outrageous because this guy down the street can do it for a fraction of the cost, but you and I both know it's bullshit. You know, it's bullshit.

Nate Wright:16:42
Thank

Nate Wright:16:56
So, I mean, just due to depth of experience, right, I've been doing this a long time.

Nate Wright:17:08
I do believe that there are ways to... serve both prospects on a sales call, not necessarily with a single piece of marketing or a single email. But when you're actually on live, you're in that video call, this is your chance to sell yourself, or sell your service, or selling whatever you're selling. I do think that there is a way that they can both meet. So example would be.

Jordan:17:32
Yeah.

Nate Wright:17:41
And this is Chris Voss thing. I probably stole it from him. is actually informing them about the reasons they shouldn't hire you. So a very real, very recent things like, Hey, if you're looking for crazy fast at this price, we're not those people. Okay. Ultimately we want to build, we get you, we want to give you a car that's actually going to like make it on a road trip. Okay.

So it's, we're probably not for you. I'm happy to let you know what you should buy to do this yourself if you want. Now, regardless of where the prospect is in that, the boldness is like, hell, I'll tell you what to go buy. I don't care. I'm not going to hide my gatekeep. I hate that word gatekeep. I'm not going to gatekeep the tech stack. I'll let you know. And people ask me all the time, it's like, Nate, like if I'm insulting someone, it's like, Nate, but.

Like, what if they just go build it themselves? And I'm like, well, so what? So what? Like, at the end of the day, the amount of business and referrals that I've gotten from people who I helped and made $0 off of, that is one of my best referral sources, are people that is like, hey, here's what you need to buy. Like, if you don't want to hire us for this, that's fine.

We're the top like in the cold email space at Upwork. We're number one. We have been for years, but they don't care, right? We're on the top, but we're also not the cheapest. And if you're on a tight budget, I would actually try to DIY it see how far I could take you. Here's one, two, three things you need to avoid. Here's how to avoid losing money. So the shift is, is I'm going from now if it's a sophisticated buyer, they're going to be like, they're used to that. They're used to that level of candor.

So they're not gonna be turned off. For an unsophisticated buyer, it's gonna take them aback at first. It's gonna cause some discomfort in the conversation. And this is something that another one of my mentors, Anthony Onorino, who writes the salesblog.com, he is like the professor of sales. And I have a few of his books and it's.

Nate Wright:19:53
It's dense, right? He doesn't mess around. But one of the things that he encouraged me to do years ago, and I was really starting to get deeper into the B2B space, is to actually embrace uncomfortable conversations earlier. And it's hard. It's hard to sit in the silence. I hate that, like sitting with a sales coach. like, all right, now we're just going to wait.

It's like, oh, I have to fill that there. I have to, I have to. But I do think it's possible to do that. Now, over time, it's, you know, with experience and as you start talking to different industries, I think the adaptability has less to do with how you're pitching it and more about your vocabulary. But if you're talking about AI here, I could import different list of jargon words for software. like SAS than I would for a commercial services business. They're just different lingo, different metaphors would be used. I like using automotive metaphors because they're almost universal, but I have been burned by it before. Where people just don't get like, they've never actually lifted the hood of their car ever. So saying under the hood means absolutely nothing to them.

And some of that may just be generational because I'm old. When I talk about burning out a clutch, most people that I talk to now are too young to have actually learned how to drive a stick shift. Or even know that cars have, other than watching Fast and the Furious.

Jordan:21:28
I will be.

Jordan:21:33
you

Nate Wright:21:36
So I do think there is a way to do it that I would say 80 % of the time for me kind of checks both boxes, but it does come with a willingness to potentially lose the business. And also you have to have a willingness to sit in awkwardness. Yeah.

Jordan:21:56
want to say three things. One is the do it yourself vocabulary or do it yourself. Secondly is fuck. It'll come back to me. So getting back to sitting in silence, you and I are very similar. I struggle with that when I ask a question and they're thinking about their answer. And it's been a few seconds. I fucking jump in sometimes. I'm like, dude, this is like the you're actually doing a great job. Like they're thinking about their fucking answer. Shut up and listen, you know.

Nate Wright:22:15
Yeah.

Nate Wright:22:25
Yep. Yep.

Jordan:22:26
But anyways, you said get to the awkwardness suitor. Can you give me a specific example so I can just understand?

Nate Wright:22:34
Yeah, OK. So I'll use a very recent sales call they had. Talked to a guy in New York, property tech company, doing really cool shit, actually. I think that my flavor of B2B sales strategy would actually be very compatible with them. But he just wanted to buy newsletter platform. He was trying to move from Klaviyo to Beehive. OK, I know how to do that.

Jordan:22:35
Meeting on

Nate Wright:23:04
Well, New York, Manhattan, I automatically think, well, this guy needs to have some money. So I was like, yeah, it's like, be like one to two grand flat fee in the beginning. If I still like you, you still like me when it's all done, we could talk about doing some more work together. I said, it'll take about a week and a half to knock it out. So.

Front-loading the conversation as soon as I knew what he actually wanted to buy not what he needed. So what he needs is a lot I think he's under investing I do and what he's doing right now, which is fine It led to he got that sticker shock right away, which I'll surprise a Manhattan guy shouldn't have sticker shock over like that, but I was just trying to give him a little grain or two, I'll knock the shit out for you, no problem. We'll help you, while we're under the hood, we'll fix a few other things while we're there, like a good mechanic would. He's like, that just doesn't seem reasonable. That was his objection, his actual word for word. And I've rarely ever had that objection phrased that way. Reasonable, like what the fuck, man?

Reasonable? Like really? I just gave you the freaking blueprint. You need to hire me. It's not reasonable for me to share any of this stuff with you. I had a bit of an emotional response internally. Thank God our videos were not. He was like walking so our videos have turned off because I am not good at hiding the emotions on my face. I probably looked like I was ready to kill somebody. that embracing that discomfort, was like, okay.

I'll put if that's all you want, I'll find I said like I could probably get something done for like 500 bucks that could get you further down the road. So basically I was telling them a car three wheels getting further down the road, which hurts my soul to do that. But my willingness to do weird deals and to do small things has led to some of my biggest clients I've picked up.

Nate Wright:25:10
you know, six figure your clients off of project. One of them started at $80 a month. Like so because the relationship was built in stacks, stacks, stacks, stack long-term. Now I don't do that anymore because economics, but I think that it's still there, but that, that embracing that uncomfortable pricing conversation earlier. So instead of waiting to the end, I front loaded the second example would be less about budget. and more about trying to suss out where their weakness is. So one way I do this and I said, hey, it's going to come off kind of cocky, but we have less of a problem with our clients of moving too slow. Our clients have difficulty keeping up with us. So the slowdown ends up being their problem. I said, I don't like talking about this because it's like, we're so bad ass. No, it's just we're fast. So.

If we're gonna do this in this timeframe, like you need to commit a certain amount of time, like your first couple of weeks, you might be spending five, 10 hours on this thing in addition to paying us. So instead of scaring them with the price, I was like, hey, you've got to be involved in the process. It's like you can't like get a trainer in the gym and not like actually exercise. But actually some people do that. They don't really do much of any work at all in the gym. So that's not me.

But that's another thing is I highlighted, like, it's gonna kinda suck at the beginning. You're have to spend this money, and on the first month, you're have to buy a bunch of equipment too. Like, suckage. So, that's an uncomfortable conversation as well, because everyone, this is human nature, is looking for the easy way. I am always looking for the easy way.

It's just human nature. However, and this is something other thing that Anthony on arena taught me is That we have a responsibility in the consulting space. We have a responsibility to ensure that our clients do not under invest So in the case of the guy where it's just a partial thing I did spec him out a tiny little task that we could do for him that

Nate Wright:27:31
was flat fee and knocked out in a week and then it's done. And even though it won't solve his sales problem, it will solve a technical problem. So it's still something complete. But if I try to figure out and like find a way to like... help him solve this issue of like taking his, he's got a massive email subscriber list for B2B, which is like rare. I'm like, dude, why are you not making more money off that? That's the problem. But right now in order to gain the trust, he needs to make sure I know how to change the oil. So, but.

Jordan:28:01
Bye.

Nate Wright:28:10
I've made the mistake before of allowing clients to under invest, giving them the impression that it can be done for cheaper. We could change the pricing model. could DIY some of it. We could get a VA offshore to help with all these ways to figure out how to like get $100,000 of value packed into a $10,000 package. And it's just, that is a mistake.

And that is doing disservice to that person. It's better for you not to have the project at all than to go down that road because you both leave unhappy.

Jordan:28:45
I do agree with that last part there. What you're describing about, I don't want to call them baby offers, micro commitments, a micro offer. And then after 12 months of working together, they're actually six figure clients. So I learned that through this purple book here. It's called $100 million Offers by Alex Hermosy. You might know that name.

Nate Wright:29:05
I've got, that's what's holding up my monitor right now. And I've got two of them. Yeah, I love it.

Jordan:29:12
Yeah, super knowledgeable guy. essentially what you're describing, in my opinion, is like ascension offers, right? Sometimes if you were to market your top $4,000 per month or $10,000 per month offer to everyone, not a lot of people are going to trust you, know you, believe it's going to work. So what do you have? You have a $80 per month offer as an example.

Nate Wright:29:29
Mm-hmm.

Nate Wright:29:39
Yeah.

Jordan:29:42
the word I'm looking for. You show up, you provide value, you do what you're going to say, you provide some level of success or success in general on this $80 offer. Now they trust you more. It's like, okay, they deliver. That's the word. Deliver on the $80 offer. Now you can upsell them to the $500 one and then to the $1,000 one and the $3,000 one, right? So it actually is a little beneficial to have multiple offers on the backend of your selling process that you don't necessarily

Nate Wright:30:09
Yes.

Jordan:30:11
verbalized to every single potential client. Like, I have 102 offers I can sell you. You don't want to do that. You want to have one go-to market offer. You know, if they don't sell them on the core services, you can down sell to a cheaper offer. Just get them in the door and then later upsell them later.

Nate Wright:30:31
Now, I agree with that. However, we've been back to the earlier part of the conversation. We're talking about marketing's role in sales. Now, when you're talking about these high ticket, the big ticket items, we're talking mid-five figures and up. And it may not be all in one lump sum payment, but ultimately,

Jordan:30:31
We have

Nate Wright:30:57
The trust the how established your personal brand is it's so important now when you try to make the leap and I know this because I've tried to make the leap more than once in my career of project based Start and small and make the leap to hey, you know, it's this is a you know $50,000 a year program and try to make that leap. I didn't commit enough So ended up actually diluting the offer, up hosing both sides of the business. And I think that instead of crafting an offer, a high ticket offer and getting it out in front of as many people as possible, I think it makes more sense to do your job.

Jordan:31:24
What do you mean?

Nate Wright:31:46
Do the thought leadership work. You're doing the thought leadership and you're putting in the reps all the hard ugly, thinkless sometimes emotional devastation work necessary to build a personal brand. I'm not doing that. Right. Do I do I need to be doing that? Yeah, I fucking do. I fucking do. And I'm not doing the why because I'm lazy. I feel that I have moments of entitlement. I'm getting too old. The Danny Glover. I'm getting too old for this shit. Okay. So The mistake that I made though is that I did have people, I had the feedback from potential clients that they wanted more of me and were willing to spend a lot more money. So I had the signal. So two mistakes made. Mistake one, the first time I tried to make the jump into like more of the, I don't know if you've read $100 million consulting offers. man, such a good book.

Jordan:32:41
I don't know. By Ale? By her mother, know.

Nate Wright:32:45
No, it's way, way before Hormoz. Hormoz has reviewed the book before. It's like something that shaped his thinking. And I got it like years ago and I ended up working for one of the guys who was one of this guy's acolytes and learned a lot. I did not do good work in that space. And I learned on that project that marketing these is a completely different game. And so I had the feedback. So the first time I tried to make the jump is like, hey, you know what? I'm going to start selling high ticket.

Awesome. I went in and started doing it, but I needed to keep the cashflow of the other business going under the same flipping brand. Massive mistake. What I should have done in retrospect was keep the bandits as its own brand and build the Nate Wright brand separately. Separate website, book, like do the work. Instead, I try to say, I'm just going to use this life raft. of the bandits to do this. That was a massive, massive mistake because to your point, it confused the offer and it got very unclear when there was no clarity. Lack of clarity kills deals. Something they would say every day in the company. So that was mistake number one. Mistake number two when I tried it again. I'm like, you know what? I've learned some bit. I'm actually not faking till you make it. I've made it. Now it's time to start selling this.

Jordan:33:55
percent.

Jordan:33:59
You

Nate Wright:34:09
overestimated how big of a deal I was. And even though I had status, I had established myself in the right circles. This is when I was working with Zige and Patela at Mailshake. I was working with Orrin Clath, where I had the rope pitch anything, in that time. So I was like, I was feeling like a baller.

Like for the first time in my career, getting invited to go speak to places and being actually going from the little Fisher price table to the big kids table. Now I moved too early with that because I didn't do the, was relying on my association with business famous people instead of becoming famous myself and doing that and doing the hard work. needed to write a book.

Jordan:34:30
You should have known.

Nate Wright:35:00
where I needed to do something press, you know, front page of Forbes worthy before I could actually do that. And I jumped and done. I overestimated it and hold man, I lost big. Like I've been in business law enough to have like, like, you know, flirted with public failure. So those are the those are the two that is the jump that's made. I think everyone I love this is what I love.

Vaynerchuk and Hormozzi. I love the fact they're being broken records about it right now is everyone underestimates the volume of work you actually need to do. just, they just, and I still like we're looking at getting back into, that's one of the reasons I said yes to podcasts. was like, you know, fine, I got to start doing some thought leadership shit again. I actually, enjoy it, but I didn't do enough of it. I quit early. I had been on like 20 podcasts and I quit. And it wasn't enough. I needed to be on a hundred podcasts. needed to be on 20 podcasts and write a hundred articles. Back then it was guest posting was the thing. Like, I just didn't do the work. I quit early. And it was a mistake. Now, looking back on it all, I'm grateful for those lessons because it helps me help my clients better now.

But also, I don't know even to this day if I want a personal brand.

So, and that's leaving money on the table, yes, but I don't necessarily.

Nate Wright:36:44
I just believe everyone's a talking head right now. And I really miss like earlier in my career working with like mentors that, all right, let's, what about a Google doll? That's right. That's fucking right. Let's, let's, let's work on some copy. You hear her, what was he talking about? I just, if I was going to do it again, I would do it in highly practical ways where it'd be me less talking, the more doing more screen share. more whiteboards, more Noah Kagan used to do live, he might still do it, he used to do live breakdowns and landing pages. I learned so much watching that. And if I'm gonna do this again, I would need to do it and like tackle like the personal brand high ticket space. That's the only way I'm willing to do it. But what I don't know, is if that would work in 2026. I'm a little bit scared if I'm wrong. If I'm wrong, that would be very expensive mistake.

Jordan:37:49
When you're saying tackling the personal brand in the high ticket space, are you referring to going after companies that rely on the personal brand to sell their high ticket offers or you Nate Wright building your own personal brand in the high ticket

Nate Wright:38:03
Ooh, that is a very good question.

I've consulted for both kinds of companies a lot over the years. So I've seen them fail and seen them succeed. For me personally, I would want my personal brand kind of divorced from the day job. The reason being is the...

My, the Bandits is already B2B, it's in the flipping name, okay? We really committed to that. I've regretted it a few times over the years, but like we, you know, we picked out some e-commerce clients that we launched wholesale stuff for, so we've been able to kind of flirt with the e-commerce space, which we were really heavily involved in back in the day under a different brand name. But I only wanted it be a personal brand, mainly because I don't know. where digital marketing and agencies are going to be in the next five years. think the era of the agency's ending. I think I might have a couple of years left in it before the... I'm not talking about ad agencies, they're a different animal. But the traditional digital marketing agency, think is a...

It's the blockbuster of 2026.

Jordan:39:22
When you say digital marketing, what do mean exactly? Because that can mean a lot of things to a lot of different people.

Nate Wright:39:27
people that sell digital marketing platforms or services to other businesses.

Jordan:39:35
Like, okay, I'm gonna manage your content. I'll create the post for you, I'll manage your content.

Nate Wright:39:41
That or honestly, anyone or any organization that would be listed on Clutch, Manifest or Brief, like an agency that is wanting to do marketing, sales and marketing projects for other companies. So I think about the agency model that retainers or the agency model of like, hey, here's a monthly package.

I don't think that model is going to last much longer. I it used to be, I've worked white label style and as a consultant for close to 50 agencies. So I've had a chance to like be behind the scenes and see how they work at all different levels, including mergers and acquisitions, how they're bought and sold. So I've had a chance to be a fly in the wall in a lot of things. And at the end of the day, unless you have...

Like really good intellectual property good IP That's the only thing that will actually make the business itself viable That's it. It's And people can say the book of business people need they're just not loyal and that laugh is just business culture I'm not gonna my myself shift the entire business culture around how businesses interact with agencies and fix the problem. That's not me I'm not going to be that ambassador now. do think that Agents, there's pieces of how agencies work that I think will survive. think another example, agencies will be devalued if they rely too much on freelancers. However, running a business that relies heavily on freelancers over the years, I've gotten very, very good at it. That skill has saved my ass more times than I can count.

Nate Wright:41:36
And I've been able to save my clients with it too. It's like, hey, you need to let go of some people on payroll. Let's figure out how to do more with less. Let's figure it out. So I think that even though that devalues an agency, that skill set is going to become more important in the next five years. So it may not look like an agency anymore, but under back office running that way, remote management, I think is going to be.

I think a skill set would go really well, but I don't think how people buy it is gonna be the same. And I've been feeling it. And you look at the amount of agencies that have gone out of business in the past couple of years, like a lot. There used to be 120,000 agencies in the US.

That's just digital marketing. It doesn't include ad agencies. Now there's what? 30,000?

Jordan:42:32
Yeah, there's a big difference. How did you? I don't want to be disrespectful to anyone that owns a digital marketing agency, but. No, no, I don't think I don't think you do, though. I think if you are setting up cold email infrastructure, craft fucking cold emails and they're converted, that is a high value agency.

Nate Wright:42:34
So.

Nate Wright:42:44
I own a digital market agency, so this is...

Nate Wright:42:54
Mm-hmm. Yeah.

Jordan:43:01
You're driving revenue to businesses, probably arguably the most important fucking factor in any organization, right? Anyone who says, Hey Nate, I would love to create content for you. will create your LinkedIn post. I'll manage them. I'll post them on Tuesdays, Wednesdays and Thursdays for you. You and I fucking know that does not drive any fucking revenue to an organization. It's like,

Nate Wright:43:19
and

Jordan:43:27
Not pointless, but like it's not as valuable as actually driving revenue with outbound, with ad agencies, shit like that. That's what I, that's what I-

Nate Wright:43:35
I agree with you to two major bits of fine print one in the lead gen space the level of loyalty to lead gen agencies even the badasses like badasses like The guys that like being stuck. Those guys are ballers. Okay There's still not a lot of loyalty like you could be You have one it's like Hollywood like I I started my business in the art space of music film Yeah, that's where I started in the marketing of that right so I work with filmmakers and screenwriters and they say in Hollywood you're only as good as your last your last film your last project and You have one bad month and you're gone

Jordan:44:24
That is so fucking true, fucking experience.

Nate Wright:44:27
Yeah. So that is not, and what happens though is that you spend so much time having to acquire customers. So you've got two choices, right? In a lead agency, you have a choice to just be so good that you don't miss, which is just not practical, right? Like when cold email like farts on everybody, like when Gmail, Microsoft and Yato within two weeks of each other, all change their policies. That messes with people's worlds. And you're not going to be able to deliver as good of results because everyone's trying to adjust. So no one's winning then, but you happen to be the one driving the bus when it gets in an accident. So you're going to be held responsible. And that right there, that's the second thing, is I think that businesses that rely. on lead generation from a I'm talking done for you services. I'm not talking about supported or systems building but actual paper lead performance based world. That outsourcing of generating new business should never ever ever be outsourced. You need to own the sales operation and you have to own that part of your business. And I think that it is that that when it gets separated out.

It weakens your business because it's like, okay, hey, it's time for you to exit. I've spent 10 years building, hell, I'll take something non-digital. I spent 10 years growing these three pest control businesses in this region, okay? It's time for me to sell it. So you go to package everything up, bring it to a business broker and say, hey, I wanna sell this business, and they start shopping it around.

Nate Wright:46:18
So a good business person will look at it and say, OK, how are you getting new customers? Oh, I have this agency I use.

Jordan:46:28
You're telling me you outsmarted That was exactly it.

Nate Wright:46:28
So maybe I should go buy that agency instead. All right. So that's, I think that it creates, I think it's almost cancerous. It's almost like, not cancerous, like that outsourcing your sales means that you're outsourcing one of the three pillars of business. you have the, like whatever you're selling, right, product or service, so that.

That's why I love all the things that have been happening with product-led marketing. I love that space. Like people that are in the space that are more products, I think that that area is some of the best thinkers in business are being attracted to that area. And it's really cool to watch what they can do. There's that piece.

And because of how they build their products, it makes them more sellable, helps market, and solves three problems. But it takes a very special kind of person, or in this case, team to do it. So then you've got solo operations guys that are writing books and consulting. And I've ghostwritten books. I've wrote a little small book that's on Amazon. I've done some of the work, right?

I do some consulting, but we look at it ultimately. If I outsource the lead generation, I am a marketer and a sales expert outsourcing my marketing and sales. And I expect a stranger to be able to sell me better than me. That is.

I mean, you say it like that, it's nonsense. Have I done this before? Have I asked for outside help? Hell yeah, I have. It has never worked long term. And so I think that the systems though is building systems and supporting them, building the car for them and teaching them how to drive and maintain the car.

Nate Wright:48:28
is way more viable. And I think people that could do that, their willingness to teach, their willingness to actually let people behind the curtain, that backstage pass, even if someone still says, I would just rather have you do it, that's fine. I think it's the willingness to actually share that knowledge.

And that goes to all the Hermosy stuff, all of the Interchuk stuff, share, share, share, like don't hold anything back. And I love that model, but I myself have underestimated how much volume of that work I had to do to actually even make it that.

Jordan:49:03
I love what you're saying. I have created two offers for two different types of customers because just as much you and I are obviously great thinkers. Why the fuck would I outsource the number one important thing in my business, which is sales or marketing? Why would I give away the keys to my fricking castle? No, teach me. I want to know how that fricking ship rides, right? But not everybody's like us. They say, no, I'll pay you X amount of dollars per month.

Nate Wright:49:27
Yeah.

Jordan:49:32
do it for me. I'll show up to the sales calls. I'll text the leads, whatever the case is. You just generate them for me. So I have two offers. One is done for you, for the guys that say Jordan, do it for me. And a system installation, like we're selling the infrastructure, we'll teach you, we'll consult you for 30, 60 days after, right? We want to make sure you get results. It's our name on the line, but you're going to learn it yourself. We have both offers for that exact reason. Now,

Nate Wright:49:46
Yep. Yep.

Nate Wright:49:53
Exactly.

Jordan:50:01
Where was I going with that? I wasn't going anywhere with that. I just think that that is where the space kind of, no, this is I was going.

Nate Wright:50:06
Yeah, now there's always going to be a space for people to just are lazy. And I get it. mean, there's companies that, but that's the thing is that it's, there's something Grant Cardone says a lot in his books. I see some of his books behind you too, right? He says that.

Jordan:50:10
Exactly.

Jordan:50:21
like Grant, I do. I like Grant, bro.

Nate Wright:50:25
Yeah, says if you and I think he attributed his uncle or something it wasn't his quote it was that if you can you must. And now people apply that logic to their business and that is dangerous. That is dangerous because just because I can sell this thing. just because I can deliver the service or product or whatever doesn't mean that I should. And I think that the level of naivety surrounding specific, and I'm going to point out startups, is crazy. It's absolutely crazy to me. The level of, like, well, One, if we build, they will come. Like, just there's so many fallacies. We're going to build this thing and people will buy. Now, very real example here. I used Tormosi's books to build an offer to sell a B2B Bandits package targeting construction companies. OK? We have a big, great list of logos of all the people that we've worked with in and around the construction spaces. I want to do more of these projects. I love that industry.

Built the offer, pressure tested on some emails, got enough signs of life. OK, we're going to run with this version. Put it out there. Failed miserably. OK? Same thing a year later. We soft launched a little sub-brand last week called the Backroom Brands, or the Backroom, targeting not even B2B, targeting brewpups.

The beer industry right now is going through called, it's called the beer apocalypse. Because like all the crap breweries are dying. Why? Because there's just too many of them. There's like agencies, okay? There's too many of them out there. There's none, there's none. It's not possible to differentiate anything more there. So we're like, let's launch the synths, do it. We did it. We already got like freaking two clients lined up. So like we're off of a soft launch. Now is the business model gonna be strong enough to like support the balance I need to feed for?

Nate Wright:52:42
If I know like I hope so the model is good on paper, but I've been just over time I've had to surround myself with people not that are gonna agree with me have to surround myself with critics and the guy I have partnered with on that is Highly critical the way I do certain things which is good that Discomfort is a James Clear thing right the Goldilocks principle. I'm not sure who he stole it from

Jordan:53:02
Mm-hmm. Mm-hmm.

Nate Wright:53:09
I don't think that might be his thing. That might be his bad for. The oil exprinciples, they want the right level of difficulty. I think that in business relationships, you need to be around people that could be thoughtfully critical. And sometimes you need people around you that are willing to be an asshole to check you. My wife is one of my business partners, so it's built in. Built in.

Jordan:53:23
Yes.

Jordan:53:27
You need those beaut- You legit need that and by the way heads up obviously we're cut this out we got to So we should probably wrap up Okay Last thing we'll say and then we have to go but you need people just like you said that you need people who are gonna check you who are gonna actually fact check you and like say your shit's actually not as good as you think because you don't want those friends that are your big sure you need friends that are hype men of course we love those guys

Nate Wright:53:36
Yeah. Yeah.

Nate Wright:53:59
Yeah. Yeah.

Jordan:54:00
but actually helping you grow. That's the key to it.

Nate Wright:54:03
Yep. And it's hard, like so much. I would say that I'll leave you with this. I'm totally off the book here, OK? Just like parting words of wisdom. You would ask me like, hey, I like the classic, like, what could you have told your previous self five to 10 years ago, right? I would have gotten into therapy sooner. Hands down, above anything else I've ever done, what helped my business the most was fixing my shit.

I was a codependent fucking asshole or insecure asshole for the most part for a long time. I got into therapy and started like, like I need to fix me in the process of doing that. I started understanding other people more and I got a much, much higher level. The number one, the best money I've ever spent was on therapy. Now I had to go through a lot of shitty therapists first, but my therapist would give me homework.

He was hard on me.

I think that will, is like the highest leverage you have. Cause the majority of mistakes made in businesses have nothing to do with the market.

Jordan:55:19
personal problem in the way you personally think. Awesome. Nate, you're the fucking man. I had tons of fun. This might be my favorite episode. A lot of similarities you and I have.

Nate Wright:55:31
Yeah, maybe a little too similar. We haven't had our first like romantic breakup yet. to schedule that. My therapist would say we would need to schedule that argument.

Jordan:55:37
Hahaha!

Jordan:55:42
For sure, for sure. Audience, you guys rock. It's a pleasure. We love you guys. Thanks for tuning in. We'll talk to you guys soon.

Nate Wright:55:50
Cheers.


Questions This Episode Answers

Why does outsourcing lead generation hurt your exit valuation?
Nate's argument is that lead generation is one of the three pillars of any business. When a buyer looks at how you acquire customers and the answer is an outside agency, a sophisticated buyer may decide to acquire that agency instead. It signals that the business does not own its own growth engine.
Is the traditional digital marketing agency model dying?
Nate believes it is. He points to the drop in the number of agencies operating in the US and says the retainer-based model is under serious pressure. He thinks the skill sets agencies carry will survive, but not the way people currently buy them.
How do you sell to both experienced and inexperienced buyers on the same call?
Nate front-loads the uncomfortable parts: budget, time commitment, and the reasons the prospect might not be a fit. He credits this approach to Chris Voss and to mentor Anthony Iannarino. Experienced buyers respond well to the candor; newer buyers are caught off guard, which opens a more honest conversation.
Do ascension offers actually work in B2B?
Nate says yes, with caveats. One of his largest clients started at $80 a month. He no longer structures deals that way because of economics, but he credits small-entry relationships for some of his best long-term clients. The key is delivering completely on each smaller commitment before moving up.
What is the biggest mistake founders make when trying to sell high ticket offers?
Nate made it twice himself: jumping to high ticket pricing before doing the personal brand and thought leadership work to support it. He says he quit too early, did around 20 podcasts and stopped, and underestimated how much volume of consistent output is required before the brand can carry the price.

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