Landing Your Emails - Jesse Oullette - Revenue Today - Episode # 007

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Sales, marketing, and RevOps. It's sink or swim out there, and yesterday's strategies and tactics won't help you today. This is Revenue Today, and I'm your host, Jared Robin. Join me as we interview revenue leaders in our community to learn what steps we could take right now to help you scale yourself and your company. Revenue Today is sponsored by Rev Genius, and we're on a mission to bring inspiration and creativity to all revenue professionals in the world. Today's guest is someone that's been around me since early formation of Rev Genius, somebody who I've learned quite a bit from. This is a former enterprise sales leader turned SaaS founder. Email outreach expert. He's helped over 430 companies fix their email delivery strategy. He's an advisor to unicorns committed to helping salespeople land in the primary inbox. Welcome. This is the founder of Lead Magic, Jesse Ouellette.

Hey, Jared. Great to be here today, man. Really excited to speak with you.

I can't be more excited to dive in. So let's get right to it, Jesse.

Definitely.

Debunk a myth about generating revenue today.

Yeah, so, uh, here, here are 2, uh, that I have. Uh, the first one is there's a lot of people who say things are dead, uh, one being, you know, email delivery, right? Or sorry, email. And then really what's dead about it is, is the fact that everybody is so caught up on the message, right? Everybody is sitting there on LinkedIn trying to pull the next tip out, trying to pull out the next strategy. And what they're not realizing is over time, they've lost a lot of their deliverability, right? If they start with a campaign that is 30% open rate, it's not getting through to the inbox, the person's not reading it. That's pretty much guaranteed over time, that's going to continue to drop. And what's happening is people think that that doesn't work anymore. And they think cold email is a waste of time. So It's actually one of— it's our probably our number one generating, other than like LinkedIn, maybe it's our number one generating channel right now. That's one of them. The other one I would say is there's a lot of people who are super focused on personalization and they're super focused on, hey, I saw we worked at whatever, or you worked here. I saw the recommendation. I saw this news about your company. Nobody cares about that anymore. At all. It's completely gone. Nobody really cares. And there's a lot of technologies out there trying to kind of personalize things. But what really matters now is relevance, meaning you actually have to find information that would lead you to believe they might be having a problem, and you have to have that timed perfectly. Now, I know that's not a simple task, but there's definitely some strategies you can use to adjust to do that.

So yeah, help me, help me understand. So And let's group those together, right? Like sending emails that are relevant, that land in your inbox work.

Yeah. So I could give you a great example. So, you know, whenever I'm talking, you know, and I'm talking to people on like LinkedIn or any of the different social media platforms, you'll see people where I'll be talking about email delivery strategy and then people think, you're gamifying it and you're spamming and whatever. And I say, wait a second, you haven't read any of my emails. How could you possibly be saying that? How do you know what's in there? Well, let me give you an example of relevance, right, that I could use for my business that I do use, right? So let's say I'm building a campaign and one of the fields I pull in there is their website traffic for the, you know, for last year or some sort of technographic where I know that they installed some other product And then uninstalled it. Now I'm relevant to a problem because remember, when people want to— when people are having problems, they usually hire and fire people, and then they usually buy and sell tech. You know, they buy and get rid of technology, right? Like, not— they don't sell it because they don't own it. But what that means is that allows you to put information like that in your email, in your mail merges, and you can pull it in. There's a lot of ways to do it. Some savvy, more savvy sales reps are using APIs, right? Above the API, which is a of a message I've been talking about in the audience or to people on different social media. But it's really this being actually really relevant on your message. And I just get into this battle where everybody thinks right away it's spam. No, the people actually thank me for the email because I'm helping them. I get a higher response. I'm in the inbox. I'm sending highly— like these emails help people out and then I acquire customers that way. So, you know, it's just very, really weird. I mean, it's, it's like they're used to what they've done in the past, which was probably not go very deep and really kind of, you know, they've got to develop the skills. It's deep knowledge now. Nobody wants the surface-level crap that's out there. Like, it's, it's just all fluff. It's so bad out there right now. Like,

so let me, let me break it down a bit. Um, from what I'm hearing, you're saying don't personalize, make it relevant at scale. I'm saying that's awesome. On board. Like, you know, I made a post yesterday that said like, hey Jared, great podcast. I said, I don't care. Thank you for listening. Right? But like, you are getting specific and personal, just not to the person. You're getting personal to the problem because you're looking at tons of data. So you could say to me, hey Jared, I never listened to your podcast. Heard it's whatever. whatever, or nothing, right? But I saw your site visitors dropped 10% month over month. Is that what your investors like to see?

Yeah, I'll give you a couple examples. I mean, a lot of the tools have it, right? The SEO data, right? Let's say you were to pull SEO data and you were able to look at how many visitors the customer or the person that you're prospecting has. Let's say you're selling— I'm just using Lead Magic as an example. Okay, now I know how many people I could possibly save for that customer that prospect, how many people I could get now back into their funnel, how many people I could be relevant to. Let's say I saw they were on my website and I was anonymous. They didn't fill out a form and I didn't have them in really a campaign. I could take that information and prospect a few of the people there. I'd be relevant because I know what pages they were on. I'd know what parts of my content they were interacting with. And this is how I've been able to kind of— this is how I outproduced my peers when I was a sales rep. Like, I was always a top sales rep. I was closing 7-figure, you know, big ARR deals with, uh, between— I started kind of even mid-market type accounts, but then I was in the Fortune 50. And I mean, I was an enterprise top sales professional and, you know, eventually ran my own team. So, you know, it's one of those things where, you know, they don't ask you— they never ask you what's in your email. They just tell you it's spam because you're sending cold email. And it's really, really, uh, frustrating. But You know, you don't always— you can't always agree with the gurus. You know how it is.

Yeah. And to be clear so that everyone understands this, Jesse's not sending the same email to everybody. He's sending a highly specific email. He's just not saying something personal about them. Like, hey, Jesse, I heard you're—

I could charge them money for the email if I wanted to put some information in there that I thought could help them. I mean, yeah, that's what's funny is like people are like, you know, I mean, like I could paywall the email if I really if we got really crazy here, I could send them data that they could value and they could come back and say, hey, wow, this is valuable. Can I get more of this? And I mean, I wouldn't even have to charge them. They'd come back to me. So, I don't understand really. This is where it's like an unfair targeting. And I'm not going to cry about it because it's perfectly fine for me because it's like, it's a printing press if you really call it that, right? It's a great way to do it, but I just get a little annoyed by it because it's It's like there's a judge— judgment factor that goes on that it's like people I call are relevant. They know— I know who they are and I know why I'm calling them.

What, you know, why do you think personalization is such like a hot item? Like, let's, let's talk about that.

Yeah. So here's what happened to the buyer. So what the— what's happening with personalization, it's funny because I've used every one of these tools, like I've absolutely every one of these APIs, and I know where most of these people get their, their scripts from and everything. But, you know, what the personalization tools are doing, they're like Hey, Jared, I saw Amber left a nice reference for you on your LinkedIn account, and I thought that was really cool. So you're as a buyer, you're like, oh, thanks. But you're like, you're really not into— there's no real mood to like, what does that do for me? That doesn't really— like, people don't want you to be personal. Like, if I don't know you, I really don't want— like, unpopular opinion, I don't want you to be personal. I don't want any— I don't want you to be personal at all. If you're going to tell me about a problem, just come in at it and say, hey, I can help you here. This is why I noticed. Now look, that's where the discussion starts. Then it's like, now you're going to generate a response. I might respond with, hey, that's not a priority right now because of this. Then you're going to have to try to reprioritize it for me if you can tell me it's a bigger problem. And hey, if you have an offer that doesn't have risk, then I'm probably going to do it. I mean, I bought a product a couple weeks ago. Somebody figured it out, they targeted me, and I bought the product. I'm now a SaaS one of their SaaS customers. So anyways, this is really where I think the world is going wrong right now.

And you're actually being more personal than you let on because, you know, as I said before, you're going to data that's teaching about their business. Hi, Jared. Did you know right away that you're failing here as per X, Y, and Z data sources?

Yeah. And it's really clear where I go to, like, you know, a couple of areas I go, like, these are some pro tips for people that are listening. So one of the areas I can go is you can definitely look at— so what I'll do is I'll save a lot of alerts on Sales Navigator, right, where you save the alerts that are kind of showing the growth of the company and like, hey, you're starting to hire more salespeople. I saw you went up 5% last month. Would it make sense to talk about how we could establish a higher quality lead generation system in your company, demand gen, whatever? I saw this information. Other people we've helped have had the same problem. I know my buyer. I'm relevant. Why would I want— so I just, I think there's a lot of bad rap on, you know, people talk about email and it's funny. You really can't give like, this is another area is like, I also see the argument that, well, that really gives the SDRs who are working hard or whatever, a bad rap about like, they're just know, when they get a really bad one. Like, I saw some— one of the sales leaders got a really bad— one of the CROs got a really bad— like, it was just like, like volume-based copy, right? Like, we've all seen it, we all get it. And there was a whole group of kind of like leaders that were, were in there. But listen, we gave them the technology and we told them to use it like that. And if you look at sequencing, what you shouldn't do is you should never give your SDR team sequencing on a single domain where they have a cap of over, you know, 50 emails a day. If you're doing that, that's your problem. You just did that. You— they're not controlling the technology, you are. If they have to send from your domain name, it's your fault that they're doing that. And you got to kind of look the other way a little bit, and you really got to get people into your company. And these aren't like IT delivery people, right? These are people who have a growth background. They're probably paid a lot more. Like, you know, you can't expect to kind of hire like the IT person to fix your delivery problem, because remember, for IT it's a 0 or a 1, right? It's either working or it's not, for the most part, right? And that's probably the best they should be doing, right? It's— but when you want to talk about performance and conversion and some of these other kind of topics, I think this is really where the world gets it wrong. And I'm glad you're starting this Outbound 2.0. And, you know, even some of the people that I know that you're working with, uh, they're some of my top, uh, you know, like, people I share information with right now. So I'm really excited about that. That's awesome.

Yeah, thanks for that, Jesse. No, I'm curious because, like, we also do this LinkedIn cold calling. If we took personalization out and fed that same data into the cold calling machines, can you picture Drop, getting, getting somebody pick up and dropping a stat like that. I think there's a 90% chance that the person doesn't believe them. It's so good. Like,

we're, we're so fast to write. There's, there's another fashion. These people have a lot of respect for them. And I, anybody who does sales as a profession is, or is even selling to salespeople, really. I mean, anybody really on sales, I have such a level of respect. But one of the things I see is we're so fast to— if you think about all the different ways that people can target people, right? You can go SMS, email, LinkedIn, phone. The one issue that I have with phone is— and look, I'm not saying you shouldn't do this if you're a salesperson, because you do have to look at your value. And if you're not a systems person, you're not an email delivery expert, you're not doing any of that stuff, it might be time you start looking really hard at the phone and figure out if that's what you want your career to be and go to growth otherwise. But on the phone, what we're so fast to do, we are so fast to get on the phone and just interrupt our customer's day, provide them a fake phone number, right? Because like, let's, let's call it out, right? You don't know who's calling you. And when you call them, you're calling them from a fake phone number, right? Which is just the way they do it. It is what it is. All I can say is, if I pick up that phone, you better have— and I'm never going to be rude to you because I love salespeople, but you better have something to actually tell me that you can help me because now you've interrupted me. I'm with my child or I'm running, doing some paperwork for my business. You got to bring it. And when I say bring it, I mean, you better be relevant. Don't get on the phone. Don't be like— I see all this tap dance around 27 seconds. All these, it's all just noise. If there's no relevance, it doesn't matter. The whole thing is dead. There's no way to get back out of it. And that's one of the things that I really just, I look at it, there's so much noise there. And then they make it almost like it's a sport. It's like a sport to get on with your customers and do that. Now, look, I think you got to pick up the phone. You got to call people who are on your website. Relevance. You got to call people who are opening your emails. Relevance. But when you're done calling all those people, you probably got to get more people in another way that you're not taking time away. And that's where people are getting it all wrong, because people do not want to lose time now with the way that the world has shifted from more digital. The time continuum gets interrupted when you trick somebody onto the phone. And you can really do some interesting damage. I don't really react that bad, but you obviously are seeing it out there, different security people, and some of those people are hotheads. But anyways, that's my perspective on it, and happy to debate it, but just keep that in mind. I know picking up the phone works, but I don't know if it always works in terms of you're getting your customer on the phone, you're interrupting them. They'll probably just hit— Sometimes I just take the meeting and just Don't even, you know, like, I'm just like, send it over, but I gotta go, you know, like, you'll get that sometimes too. And the show rates must be awful. Right? I can only imagine what that show rate is on those calls. Right? Oh, yeah, that's another problem that you have.

Yeah, I think that people are optimizing because there's 2 different people and sometimes 2 different orgs on the outreach. And they're, they're optimizing for just getting a meeting versus optimizing with a meeting that's going to set up for a close. So this creates a massive conundrum. So you could tell me, you're like, Jared, you want to talk personalization that'll work? Jared, I went to Penn State at the same time as you. I know your sister. I know your uncle. I was at your cousin's bat mitzvah. You know what, I'm gonna probably take a meeting with that person. But I'm not gonna buy from that person.

I wouldn't. That's the, that's the weird part now is like, You know, and you're right, I probably would. But like, where it's so funny is like, if one of my own family members did that and they were trying to talk to me about something, I probably would tell them no still, I'm so busy, right? Like, so that's where it gets really interesting is like, some people think that that's still working, right? And look, we have our campaigns down to like, I mean, I could spit, you know, I could tell you the metrics of every one of these campaigns exactly, like LinkedIn, everything, like exactly what the numbers would be. And happy to be tested there, but I know what a good campaign looks like. I can tell you what a bad campaign looks like. It looks like a person on a call, getting on calls, getting 10, 15 meetings in an hour because they had the exact mobile numbers, they got them, and then all those people rushed them off the phone, and then none of those people showed up for the meeting. And nobody— you never see the show rates on those discussions. So you have to look at the whole picture. And some people might be doing it effectively. I want to see the data. That's all I want to see. And I want to see not only the inputs of how many calls you made and all that, I want to see how much that team cost. And that's the transition of, that's what's going on. People are starting to have to run real businesses. And we've talked about this, how hard it is, but you have to show an exit strategy. I mean, you have to show a business that's profitable. Profitable, right? Eventually, right? You have to get there.

Yeah. So Jesse, like, okay, understood the personalization, that was yesteryears. It's smoke and mirrors a bit. Um, sales engagement platform, it's not that you have it, it's how you use it and, and all of that. Are there any tools you would add to the stack to create, to, to build in the personalization of the data part? Because this is something that Not every, you know, now people, you're, you're starting to inform people about the emails and going into the inbox, but how do you do relevancy at scale in a way that connects?

Yeah, so I'm doing it with, so, um, couple, couple ways actually. Uh, one way I'm doing it is there's kind of 3 ways. Uh, first way would be Google Sheets because that's a nice landing zone for data. Uh, I actually working with somebody outta the, um, Rev Genius that I, I think I told you about the jobs. I found somebody in there. You could build an Apps Script. I have my own APIs so I can use those. There's other ones out there. There's all kinds of ways to do it. That's one of them, Google Sheets. And I think Google Sheets will be the new UI for data. That's kind of the, you know, like people like to use what they like, right? Those are the most powerful programs. The other one would be Airtable. There's a couple of ways to do it in Airtable with Data Fetcher and some of the other extensions that are in it. You can build some of these and Airtable's also adding. Plus there's any number of companies that have built up front end to every Airtable. There's, there's Pori, there's Softr, there's JetAdmin. There's a bunch of companies that have built essentially front ends to Airtable. Noloco, that's another one. Anyways, those are the ones there. And then on top of that, there's also, I think you're working with them, Play.run, which is a nice way to do it. I mean, I think everything's gonna blend into a spreadsheet. with APIs. And that's essentially going to be your kind of data landing zone. And you're going to have to get that information right, you're gonna have to get it relevant. And the person on the other end, if you get it relevant, they're going to know, you know, their problems. And it's not going to matter how many things you read on their LinkedIn profile. It's not going to matter what cute little subject line you used. It needs to be relevant and it needs to be in their inbox. Those are the 2 things that are non-negotiable. If you get both of those done and you're there, you'll, you'll convert at the higher percentage. You'll be in the top like 1%, right? That's what we focus on.

I friggin love that. Yeah. And don't confuse Jesse for just being an inbox guru or not— bad word choice— but, but, but relevancy as well. Now let's take it Let's move forward. KPIs, what are the ones that are important to you today?

So, breaking it down by channel, so I think if I really have to look at a team that's prospecting, that's creating lead generation, what I'm going to look at is, I'm going to look at the— I mean, my business, I'm going to look at the cost of the team, because that's something that I have to think about. how do I hire people? And don't have anybody on the team and just think about it as, what does that team cost? What's the dynamics there? What's the market doing with that team? Is there going to be other jobs that they're going to get? What can you pay and how long can you pay it? And can you create a growth opportunity for that person? But the biggest metrics I look at right now is you start out with the impression of that buyer. They see it and they put their attention on it. Then it's the responses. So like the attention part is like, if you're on LinkedIn, you know, you're looking at a 30% response rate if you're connected to the person. And this is where a lot of the other people go wrong is there's so many people that are saying like on LinkedIn, they're saying don't pitch and sell. And I don't know what they— it's tough because everybody has their own definition of that. But if you're not out there connecting to people, you should be maxing out your connections every week of 100, to abide by the terms and services unless you, you know, figured out a way around it. Uh, but the point is, is 100 connections a week— if you're talking 100 connections a week, that's 30 new, uh, you know, people that are going to accept your connection. You're probably respond— or sorry, maybe 20 people that have accepted, and then you're going to get another 6 or 7 responses. That's going to be a lot of good information because remember, that person you're not catching on a cold call. They're gonna have a couple of minutes to look at what you're doing, look at your landing page, which is your brand and how you— your company and how you present yourself. And that's the kind of metrics you should be looking at, is how many times are you getting in front of your customers? And remember, you're not in front of your customers if you're in the spam folder. That's another thing, right? So you gotta get in the inbox, the primary inbox. And then once the eyeballs are on it, the next metric is conversations, right? That's going to come through responses. So we look for positive and negative responses. The negatives are never that negative. They're like not interested or like, you know, whatever. And that's kind of how you got to look at it, you know, and you should be getting at least a 15% positive response. That's kind of how we look at the responses. And then really after that, you're pretty much one of the most efficient lead gen you know, strategies out there, right? What I just described. So you're not fighting with people, you're not asking for hard CTAs of a calendar invite, you're just asking if they'd be opposed to learning more.

I love that. So sounds like everything's going well. What's keeping you up at night?

Just, it's always the— I know I've, just because I failed a lot, right? Like, I know I've developed some pretty Uh, you know, a lot of the skills I have are— I've definitely failed 10,000 hours. Like, I know, I know where I am at, at certain parts of the go-to-market strategy. But where I get nervous is if I sometimes can scale offers against my expertise versus against what I'm trying to build. And that's any founder's kind of nightmare of like, you know, you can go in and get a consulting deal. You know, you can go in and get whatever. And you know you have something on the website and you know you have that, and then you gotta watch churn and all that. But the problem is, is not taking on something that is taking a lot of your personal time. You need to be able to fulfill, right? Because you have sales and you have fulfillment, right? Because customer success, and you've got to be able to do both. And you got to put a line in the sand and you got to have somebody you trust running the success part of it. And then you got to be the person that's selling if you're on the other side. And revenue is what matters, right? Obviously, there's companies, Amazon, revenue, Microsoft, revenue, right? Grow your company, you're gonna have to sell shit, right? So that's kind of what's out there right now. That's what keeps me up is just around, am I selling the expertise or am I selling a product that can be renewed, that can grow, that can get the customer impact, that I don't have to be 100% the number one reason.

I love that. So other people that are facing the same challenge— I'm facing this challenge. Last day I was offered a Patreon spot and like whatever else. What advice would you give?

You know, I always, as much as You know, you look around and you look at like the different people that are getting pretty good followings. I look at a lot of Justin Walsh's stuff. He really produces some high-quality stuff. And if you look at his approach to saying no, because what happens is you start to grow and then it starts to compound, and then one thing turns into a next. Can you pick— can I pick your brain? Can I do this? It's the number of nos is the question. And I'm definitely guilty here. I know There's certain areas where I've given a little too much in certain areas, and it's put me, or even like, you know, there's times where you can put your customers in a bad— the ones that you put yourself in a bad spot. It's hard to really figure out, you know, you're either working too much or you're stressing out, right? That's burning out, right? You don't want to do that. You'll always get the job done if you're there, but you just don't want to burn out, and you got to play the game long. You know, and you gotta kind of ignore the gurus because, you know, there's— you could wake up to 3 people telling you you're spamming people. And I'm like, well, what's your delivery rate? And which— how many of your emails are in the inbox? And how many of your customers are responding? Because those are the metrics that I look at when I think about spam. And if you think of different metrics, probably don't need to have this conversation. So You know, just ignoring the noise. There's a lot of people that come at you, you know, start to rise up, but it is what it is.

What excites you the most about the future, Jesse? Like, like, there's a ton of everything now, and you're helping really evolve the future, right? You yourself, us, like, together, like, all of this, we're creating it. But what excites you about it? Like, what—

I think it's the fact that it's— there's— I was playing a When I was working at software companies, I was always trying to get to the end. I was always playing a game of finite scores. And I think what's exciting now is there's no ending to it. Even yesterday, I lost on one of the— whatever the games there, the GTM ones. And the judge was— I told the story, I was just the last place. I told the story of building my company and everything, and I lost. It's not the first time I haven't disagreed with a solution selling sales leader, but whatever his name was, the Xerox guy there, the solution selling, I forget his name. But anyways, but, you know, I look at it like the future hasn't been built yet and there's a lot of opportunities for people to build their own SaaS products. The tools are getting easier to use. I mean, you could physically go out today probably learn enough about no-code on YouTube. You could probably do most of it, probably get a firm maybe to help you with the last couple pieces of it. And then if you had some sort of brand or you knew sales and marketing, you could scale that thing up pretty quickly. And it's exciting to see that it's not just kind of the engineering group. And I think it's equally as exciting to see some of them have to come more to the sales side, and some of them are becoming amazing too. So I think what people— what's exciting is it hasn't been created yet. You can play it long. You don't have to play it short. And I think if you look around, there's some companies that have been playing it really short, right? They took massive amounts of cash, against probably even some of their founders were like, should we be taking this much money? Do we need this much money? Well, they definitely didn't need that much money, right? Like, that's pretty clear. They needed to roll up their sleeves and get back to the inbox, start getting the email delivery working, start getting things that actually matter in SaaS companies. And it's like the fact that I could even build a SaaS company and compete against a company that has $100 million in revenue, or sorry, $100 million in VC money, they don't have $100 million in revenue, but I look at that and I'm like, man, that is a change. And I hope there's more. I know you've done it and it's great. You're creating jobs, all this. I just think it's great because there's an opportunity for everybody to do it. I don't think there's any limits. Nothing has— even look at Andrew from MicroAcquire. Just look at these stories. They're amazing. And you just hope to be part of one of them. And you hope you don't lose on a storytelling contest against the guy who made the Xerox solution selling. But I'm not bitter or anything.

No, I love this. I think today we're seeing sellers sell a service, sell a repeatable service, right? There's platforms like a Patreon, for example, that you could get that MRR in. Tomorrow we're gonna see that person build a business Because they're tired of hopping on Zoom every Tuesday at 8 PM, writing a playbook every month, and having one-to-ones, which by the way is spectacular to do, but it also seems like everybody's doing it.

Yeah, it's really hard to do it, right? I don't want to trivialize it. I mean, there's some people who say, oh, all you need are these 3 tips. And I look at that, I'm like, oh my God, if you only knew. I'll tell you a couple tips if you're going to go do something, right? What I wouldn't do is what I did where I just jumped out, where I got— when I had a little bit of an issue there and I wasn't able to keep going with big SaaS, I ended up leaving. And what I wouldn't do is if you can avoid that, avoid that. Try a couple of things on your own, digital products, something. Put something out there like an info product or something. Just so you can get a feel for it, right? Because it's pretty cold when you go out. Now, the other thing I would do is watch out for that thing that I talked about first, where you come in, you're like, wow, this is easy, retainers for life, right? And you can get those, right? If you're good, if you had a good career, you have some relationships. But where you can really get into problems over the long run is if you don't start to build productized service to scale your time, because you're gonna lose some of those retainer. Like when you start showing them how to do things, when you start giving them your expertise, even if they can't do it, they're gonna think they can possibly do it on their own and they're gonna possibly have your prices lower right away. So you really need to be, and I don't care how good you are, that's what's actually even more alarming. The better you are, the sometimes the worse you can do in this situation. Because if you don't build the right product, we've all tried to build products that you can sell, you know, that people are going to buy, that they're going to buy it, it's not going to take up all your time. It's tough because you could go out, take 3 $10,000 retainers, you're back to your OTE, and then you're One month goes in, you're down one of them, that company closed, and you're down the other one. Now you're chasing, you didn't have a product going out. Like, if you haven't— so all I can say is, if you're going to leave, build an exit strategy, build a plan, which is what, you know, join communities that have kind of people doing it. Don't just jump out in the cold unless, you know, if you have to, you have to, right? And there's no turning back there. You can turn back. That's the other thing. There's always an opportunity to turn back on anything. That's like that's that's a lie they used to tell you, right? That's something they lied to you about. You could go back as many times as you want. You could get fired ten times and they'll still take you back. So don't worry about it. You know, you can always get back to where you need to.

I'm interviewing with FedEx right now for those listening. I'm going all the way back.

I love it. Just I love it.

Yeah, I decided I want to work. I've negotiated the long hair. That's the only thing. Suits, suits are a non-starter for them. But

anyway, get on that show, man. I love it.

How funny would that be if I went all the way back to FedEx and just ran full communities on the side?

I bet you'd still be the number one rep over there.

I don't know if I would care enough. That's the one thing.

Yeah, yeah.

If I wanted to, I would, but you need to care to be the number one. But

anyway, yeah, that's another thing, you know, just Remember, like, you don't have to win. I think that was another thing that I did is I thought I had to win every competition. I realized really quickly it's good to lose a lot of competitions too, right? You know, I know there's 2 schools of thought there, but go out there and lose. If you're fighting a group of people who you don't really need to win anymore against, you're probably gonna just need to move, uh, you're gonna probably need to move around that, that block. and get around it as quickly as you can, but you might have to just walk around it nicely and get on the other side of the fence. Because if you try to go remove the fence without knowing how it was built— a good mentor of mine, there's a principle called Chesterton's Fence Principle, and he told me about this. Like, if you don't know how the fence was built, don't tear it. Don't try to tear it down because it could take you a long time. This is a little bit of a second-order thinking here, but it could, it could really waste a lot of your time. Like, sometimes you let the fence stay up and you just walk around it on the other side of the gate. And you're fine. You'll get on the other side and you can go run in that beautiful field that you saw on the other side. And that's like, hopefully that gave you a good visual there.

Perfect visual. So the, the first half of this interview, we learned from you and, and you, you dropped some knowledge bombs, and thank you for that. The second half, let's learn about you. All right, so Jesse, who are you?

Yeah, so, uh, you know, I could kind of start. I live in Boston, uh, here with my wife. I have just recently become a father, girl dad, of course. Yep. Uh, it's fun, it's a lot of fun, it's a lot of work. Uh, my wife does a great job. She's a, she's a school counselor, and, uh, she's still a school counselor and everything. And then, um, there's, uh, you know, SaaS really. I mean, SaaS is really just a billing model, you know, when you really boil it down, when you start to talk about it that way, it almost seems like it's this other thing, but do they have SaaS experience? It's like, what is that? But what I'm trying to do now is instead of selling a deal where it's a 7-figure deal and the renewal's going to come up and I'm not going to have any equity, I'm going to make enough to W-2 a great living, but it's just, I want to have something that you own part of a business, which is, I mean, fortunately I own the whole business right now. which is nice, right? Like you own the whole thing if you want. It makes sense sometimes to give some of that up, right? I think that's a good thing in certain situations, right? You should, you need people to help you. Capital is leverage, code is leverage, distribution, these types of things are leverage, media, those are leverage. And you need to look for those. You need to look for those pathways where things are working while you sleep. there's nothing better than being at home and someone signs up for your SaaS, right? You get the Stripe payment, the notification comes in and you're, wow, that was a lot easier than going and meeting them in New York City. It was a little bit of a journey. Of course, I didn't really know how to code or I really didn't know how to, I was very, I was technical enough to figure it out, but, you know, that's kind of the The who really, uh, here.

I, yeah, I, I heard awesome dad, girl dad first, wife is amazing, and then you just like, what you do is your life, right? Like you, you spoke about, um, SaaS right after when I asked who, who you were. Can you connect like how, how you got so ingrained into that, you know, You're, you're a senior at University of Maine, you know, you're living that college life, uh, deciding that Boston is for you after. How do you go from that point to startup founder?

Yeah, so, uh, my, my, my father and, uh, grandfather were also entrepreneurs, successful businesses, both of them. Uh, my grandfather's no longer with us, but his business, did well. Also, my dad owns a profitable business, does well. And I think what was kind of news to me is I lived in that world of family business and saw that. And then when I grew up and saw how some of these places could be run, and then I saw how they could really be run with a bunch of extra money hanging around, it got a little worse for me. It was harder because I had just You know, my background was running sustainable businesses that people trust each other and like run. You know, it's just like a different world, right? It's not that they can't trust each other in those types of businesses either, but sometimes it's— it was so hard sometimes where I was kind of there as a salesperson, 50% commission, and then there was a marketing person there, and I felt like my territory would be impacted by not being able to run the right marketing or sales campaign or marketing campaign. And to think about that person, if you think about it from a financial perspective, it was really hard to get to a point where I'm making 50% more of my variable, the risk, at-risk component is way higher. And that's just the way that these organizations are designed, good or bad. And certain scenarios, it probably makes sense. Certain scenarios, it probably doesn't. But yeah, I mean, I spend time with family and friends on the weekend. I, I've really, you know, there's not much else you can do when you have a child, uh, who's 7 months old and a, uh, business that you've started within a year. Uh, you know, that's kind of the two things right now. So.

Nice. And, you know, a couple takeaways there. One, first off, 50% commission, that sounds worse than it is when you're making 100% more than the typical other salesperson. Like you're guaranteed the top level. Like at FedEx, I was making $119K. That sounds like a very common base salary of an enterprise sales rep, $120K, right? Yeah. Like, so yeah, to be clear, so like, you know, that's interesting there. But the second thing is, um, your desire to run a good business is defined by profit especially, right? Right? That's big.

Glorious profits.

And, and everything you do with, uh, bootstrapping yourself, um, rooting on other bootstrappers like, like us or other people not taking VC money to the point of you being intrigued with private equity. Remember the conversation we had? Because,

yeah,

like, like helping other companies Yeah.

I think that's a big area for me. I mean, I get the model. I get the model. I get— so it's just like I said, that fence, you don't want to try to tear it down. You see why it's built. And I could certainly see a reason why I would take a different raise on. If I had something that I was doing that was way past the risk tolerance that I have, but this was a pretty easy calculated move. I went out, I knew what product I went and I trust, if I collect the data, if I'm collecting it, I have a pretty good confidence level in what I'm looking at. And I'll tell you, it's funny because I see a lot of people who were like, X, whatever, X this, they went to all these successful— they had 2 companies they went to, both of them were like 8 years successful. Now, I look at that, I'm like, okay, they probably dealt with some stuff, but there's some really bad walking dead unicorn didn't even get near the unit. We don't hear those stories. We don't hear the ones where you get on a call and they fire the whole sales team except for you. We don't hear the ones where I would get called like, hey, is your deal coming in? Because I have to go fire 5 people if it isn't. Or, we're not going to pay people commission because we're out of cash. You don't hear those stories and you hear the good ones, but The funny thing is, is there's probably some people who've developed some very, uh, some skills in those organizations that are pretty elite. It might be— they might look jumpy. Like, you could look at my resume, there was 11— sorry, 10 jobs in 11 years, right? Every job, every one of them, I went in and I was able to produce something that was more than, you know, probably most of the reps there. And then I was able to get up and running fast, right? And that's what I look at as, you know, it's a little crazy because there's probably some really talented people that might have been overlooked there. So when I look at a resume, I look at it completely different. First of all, I don't care how— I just want to ask them, like, sometimes if I say like, hey, why'd you leave there? Place sucked. They couldn't figure this out. Like, hey, that's fine. Like, you know, once they start to extract like how I would feel in that situation, I was in a lot of those situations. And I think there's a lot of like look at this resume, let's get this one in there. They were at 5 successful— those people, sometimes it's dependent on the person, but I think there's some great people that get overlooked because of that, right? You're at like 3 companies and that could be the best person on the team because they got pushed out because they were creating such a— they wanted the plate. They had resolve, which is what happens in Six Sigma manufacturing, you know, any of the— anything out there. they had some resolve in their life and they asked for things to be done right. And they trusted everybody and everybody had to bring data with them. And if they didn't, I mean, that's kind of like you start there. If we're going to talk about something that's going on, we're going to look at all the information and make a decision on that. If you don't want to use that information, use the loudest guy, mostly guys in the room, right? That's what's going to happen. You're going to have a lot of these failed Broken, worn-down software companies.

Jesse, you'd love my old, uh, my old roommate, frankly. He— his dad gave him a deal. He'd pay for law school, all he had to do was graduate. So he went to one year, rang up $40 grand, and dropped out. So he was on the hook for $40 grand. Moved in, his dad hooked him up with a job at Lexmark back in the day, um, in a new division. Guy's getting paid $80K out of college. He somehow finagled that 15 years ago, which is quite a bit. at the time, right? Like, it was ridiculous. Ends up being the top seller on the East Coast, crushing it. They fire everybody but the top seller on the East Coast and the top seller on the West Coast. He stays on, uh, pays off his $40K, and then, uh, and then went to companies like— I, I don't want to, I don't want to name the companies, but he figured out ways to—

Buy the docs and—

He— no, no, no, not even that. He just found out ways to hack the system. He's like, Jared, I know every every 44 days, like it's right before the accounts are going to come. So I lay my stake here and I find people closer to the pipeline and then I just close them. I'm like, I'm the number one here just because I've gamified the system that they created.

Yeah, I think we're all trying to get our time back. I think that's the thing. If I can figure out a way to build a system that will save me, you know, a couple hours a week, I'll probably spend a week or two on it, right? So I understand. And that's big.

What do you do outside of work, Jesse?

Yeah, a lot of it's, like I said, spending a lot of time with my wife and daughter. We go a lot to Cape Cod or like, you know, New England's beautiful in the summer. Winter is a little bit tricky, but, you know, stuff like that. Family, friends, that's the type of stuff. Like, that's been— I live here in Boston. There's a lot to do. Like, I live in the city, so it's— there's a lot to do here. Pretty much what, you know, my life is pretty much that right now.

Jesse, um, you know, I, I respect you immensely, one, for, for putting yourself through this, uh, road less traveled, but doing it at a high level of potential stress and welcoming your first kid in, being a great husband, uh, and, and finding time for random hooligans on the internet that are building stuff. Right? Like that.

Those are the ones. Yeah, those are the ones.

I can't say it any different.

Yeah, no, you're right. You

know what I'm talking about. Reds and hooligans. Because these are people doing great things their own way and thinking outside the box.

That's what I love. There's a little bit of— I always say sometimes you got to get off the rocket ship and get on the pirate ship. That's what I tell people sometimes. You get on there, you figure it out, you'll get You sit there, you have a glass of water, you be a homie, and you're really where you need to be.

Jesse, I love it. Tell people how to connect with you. How can people find you?

Yeah, sure. So if you just want to go to my profile on LinkedIn, DM me, that's fine. I usually respond if there's relevance there. Of course, we talked about that earlier. And then also you can go into the— go to leadmagic.io. That website helps people find out who's on their website, make it easier to call them and prospect them more relevant, of course, like we talked about. Uh, there's been really that, uh, there's been a lot of— there's a lot of people on dark social that I talk to. I'm in a lot of the different communities. Uh, you can find me in the Rev Genius, of course. Love kind of going in there. And then, um, yeah, so that, that's it. I'm also doing some audio events with you upcoming here. Yeah, or whatever. I'm really excited about that. Yeah, looking forward to this, and I really appreciate the time today,

Jared. Jesse, thank you so much. And, and for anybody listening, like, Jesse's going to be doing a lot of programming in Rev Genius. Come learn something. Fire up the questions. The more complicated, the more the more critical, mission critical. The more Jesse will go in. Yeah, yeah. The deeper we'll go. But you know, thank you, Jesse.

Appreciate it, man.

And thank you for listening. If you learned something today or laughed, tell somebody about this podcast. Thanks again, man.

Appreciate you.

And this has been another exciting episode of Revenue Today. See you next time. Whoa, another great episode of Revenue Today. For show notes, links, and mentions, visit revenue today dot live. For all my friends in the Rev Genius community, thank you. It's been awesome to spend this time with you. Please DM me any feedback and ideas in our Slack channel or on LinkedIn. If you're not in RevGenius, join us at revgenius.com. It's free and it only takes like 2 seconds and you'll be joining a group of 27,000 revenue professionals strong. We've got it all. Looking forward to seeing you there. Catch you on the flip side.