From Cold Email to $400K MRR — Building a Scalable Pipeline w/ Jeff Winters | RevIntel [Archive]

We always say we get together on a Friday and we say hit the button. So today, guys, we've got another episode of the Connect podcast. And today I am privileged to have Mr. Jeff Winters. He is the CRO of the Grow Show.

Is that correct?

No, it's of a company. The Grow Show is the podcast. CRO of a company called Abstract Marketing.

Exactly. And I have been told many times before, it's always how I start my podcast, Shane, you need to shut up and just hand it over to the person. So Jeff, who are you? What do you do? And why do you do it?

Hmm, deep. Who am I? You want like a business answer? You want a personal one?

This is— we don't care about businesses. This is me and you now. We're in the living room. We're shooting the shit. I want you.

Okay. All right. Um, I'm a, I'm a guy who grew up like mostly below average at stuff, you know, like didn't, uh, didn't make any sports teams, didn't, uh, have any like great achievements early on in life. Um, and, uh, like found his way professionally into sales and, and figured out how to get sales meetings. You know, the story Story is I was, I got hired to be the chief revenue officer. Yeah, I guess chief revenue officer at this startup. And this guy who hired me is like, yo, and I figured like he had found me out of obscurity, right? Like he, he had found all the potential my mother thought I had. I was like 27. This guy hired me. Of course he did. Why would he not hire me to be the chief revenue officer of this venture-backed startup? Like, why wouldn't he? Of course, what a great option I am. Meanwhile, I've got no experience at all in tech sales. I get there. First day, and he goes, um, yeah, really excited to have you, thanks for coming, but, um, you can only sell this product to like chief human resources officers of Fortune 1000 companies. It's not really done, we never really sold to anybody. So I'm like, okay, well, I guess he didn't find me out of obscurity because I have so much potential, he just couldn't figure out anybody other idiot to take this job. So I like took this job and I sucked for months, and then finally I'm getting my resume ready and I start sending funny emails in the middle of the night to really high-level folks at big companies. And the one that sticks out, I went to Morgan Stanley in New York, like big edifice, you know, 9,000th floor conference room. I walk in, there's way too many people there to look at this software that kind of exists. And they're like, Jeff, thanks for coming, excited to see you. Like, how in the world did you get this meeting? Tell us how you got this meeting, because like people like us don't meet with people like you. Meaning, you know, we didn't really have software, and I quit and started a company, and my professional identity was company called Sapper Consulting for 10 years and got it to 150 people and sold it to Abstract Marketing Group. So that's my professional identity. I'm also a husband to a wife that's too good for me and 3 kids that treat me sometimes okay, most of the time, you know, just like kids under 9 do. And I just got a dog like 9 weeks ago that is causing trouble. So there you go. Is that— that is what—

that is exactly what I love. I love to hear that you exactly give you a bit of context about who you are, your background. And obviously this will lead into where you got your spark from and challenges and successes along the way of that journey. So what do you do now? What's your day to day like right now in the company? Now tell me a little bit about the company, what you represent and what's your day to day look like as a CRO?

Yeah, so we've got this full-service marketing firm. Um, we're doing appointment setting, we're doing, uh, like blocking and tackling marketing, awesome marketing websites and SEO, PPC. We've got a Salesforce consultancy, we've got a staffing firm, we got this growth firm is really what we are. And what I do is I'm the chief revenue officer, fancy title, but Irrespective of that, I get to do what I love doing, which is I directly manage sales. I directly manage salespeople, which I don't think I'll ever stop doing. I love that. And my day-to-day breaks this way. I'm probably on calls 25% of the time, give or take. I love hearing, feeling customers. I think chief revenue officers that don't get on calls either suck at it or think they suck at it or think they're above it. They're wrong. Maybe they do suck. I can't say whether they do or don't, but like, at least they're wrong. I spend about 25% of my time in internal meetings that we try to make as tolerable as possible. I spend a percentage of my time thinking forward, thinking about what we can be doing better, forward-looking. I spend a chunk of my time meeting with my team, quite a bit of my time meeting with my team, making sure they're fired up. I probably spend a disproportionate amount of my time with my team making sure they're feeling good, way more so than I bet the average chief revenue officer would, and I wouldn't replace that time for anything in the world. So that's my, that's my day to day, my responsibility. I got to sell, you know, 100 or so new clients, $400,000 in new MRR every single month. That's my job, baby.

Wow. Okay. And the big question is, why? Why do you do this?

Um, so I, um, the best way I can describe it is I sort of have like these daydreams from time to time about— yeah, yeah, it's good. You're gonna really like the rest of this if you like that part that much. Like daydreams from time to time of like, um, people who I, I'm directly managing coming back to me in 5 years being like, hey, you know what, like, I am where I am today because, like, you played some small part in my journey. I've had that happen already. It's the fucking best. Can I cuss?

Of course.

Okay, well, I don't know. Um, yeah, that's the fucking best. That's the best. That's the best part of this whole thing. And now I've, like, built— I think I've helped a lot of people along the way become great. I just love working with young green leaders and helping them helping them achieve greatness, like, later in life. Not now, you know, but later in life.

So, wow, bro, that's very good. So, managing a team, for me— yeah, I'm a— I ran an agency for just shy of 4 years. I got very, very tired of, um, again, I'm very honest about this stuff, I got tired of managing people. I got tired of bullshit. I got tired of telling, telling people what they knew they should do, what they had to do. And then my biggest mistake was I had to separate my friendships from being an employer. And that really broke things down very, very quickly. So for you, what do you think the hardest thing is? The hard— we'll do the hardest and then obviously we'll do the best. But what do you think is the hardest thing about managing people and a team in 2024 when there's so much information and shit to do, so many distractions? What do you think is the most difficult thing about managing people and a team today?

So first of all, I love managing people on a team. You know, I have so many people in my life that go, gosh, hey, you got a lot of people there. And B, I want to start a business with no people. I'm like, God, that's such a— it's boring.

I wouldn't want to do that.

Like, working with people is one thing, being responsible for them, for me, yeah, I'd rather do my own thing.

Yeah, no, I get it. To each their own. But like, you know, when you, when you hear about like what, what I give a shit about, what lights me up, it's It's those interactions down the road later in life for those people. And so I can't have those interactions if I don't have the beginning interaction. Um, I think, uh, I think the hardest thing for me probably is getting people to trust that I— like, my—

my—

is to trust me and that I'm actually not doing it for myself. You know, like, my philosophy is with people, it's like, I'm gonna— I am going to be critical. I'm gonna be like, my job is to get more out of you than your mother thought you were capable of. But that requires you to have to Trust me. And I think in general, in this, in like, in this day and age, it's most— I think people are a little mistrusting of corporations, especially sort of upper-level management in corporations. And, you know, for me, I've got, I've got to get people to trust me and buy into what I'm saying. And, um, I think that's probably the most, the most difficult part, I suppose.

And what do you think then is the best thing about it? Um, other than the journey, like the 5 years, the 5-year compliment, let's call it right now. Let's— what, what else? What else serves you?

The 5-year compliment is great. That's a good one, right? Um, I'm gonna totally steal that. You're, you're in the, you're in the right line of work, my friend. It's the best. That's the best part. Um, I think the— my favorite moments are when you've got somebody that's doing really well but not doing great. And for a long time, people have accepted that of them. And I don't. And I come super hard and like, look, you just can't be on this team if you're going to be that way. I love you. I think you're great. I think you're awesome at what you do. Like, I genuinely enjoy you and care about you, but you're not going to be on this team if you're at that level. And people are so shocked in that moment of like, wait a second. You know, because it's about a particular standard that we're going to have on our particular team. And either you do it or you don't. It's not personal. It just is what it is. And people that are high performers but not the highest performers, you know, you know these people. We all know these people. They're people who they've been allowed to be 5 minutes late to a meeting, or they've been allowed to not do this because, oh yeah, you can't. Those people love those moments. And I love those moments because then you can really— that's the real gap. Like, you've got high performers, but they're just not the highest performers. And my job is to get as much out of you as you're capable of. Like, When you start to think of it that way, not to be like hokey, you know, LinkedIn clickbait shit, but like, that's it. Like, that's what, like, you know, that's, that's, that's your job or part of your job. So in those moments where I'm like, shit, like, I can see this person clicked when I, you know, was more, was more challenging than others have been because they're a high performer. Oh, that's good. I know I got that person for a long, long time and like they're going to perform and that's going to be great for them and the company.

Oh yeah, I will tell you that. That, just the fact that you mentioned that in 2000 and what was it? 2018, so 2017, I had joined a media publishing company and it was my first transition from delegate sales to sponsorship sales. And I would always follow the money. And what happened was I was placed, I actually was hired by Gartner and this was in the UK. I was hired to be one of the delegate sales managers, and then they found out I had a criminal record in the US. I had 4 felonies and I was not allowed to go back there. And 13 times out of the year they were traveling to the US, to Connecticut actually, for conferences. So they said, I'm sorry, Shane, can you go back and ask your company for a job, for your job back? I said, no, I ended that shit bad. Like really bad. So learning lesson there.

Don't burn your bridges.

And, uh, he goes, okay, cool, we'll pay you, we'll pay you, we'll pay you for the time that you had the gap. And then, um, like, we're sorry, but we're gonna have to pull the offer. And then I had to take like the second best option, right? And that second best option was, uh, selling the most garbage conference on the planet. It was called the Global Semiconductors and Electronics Conference. We were selling it from Holborn in UK and we're calling US people to fly to Shanghai, China on their own expense and then pay for the conference to sit in dating one-to-one meetings. It was awful. Okay.

Tough sell.

I sold one sponsorship place in the entire 7 months. It was $10,000. It was on my 6th month. After I'd done that, the person who hired me, Richard Crosby, he said, I was walking out, I said I was sick, I feel sick, my stomach. I was bullshitting. And as I'm walking out, he goes, Shane, come over and sit down with me. And he's like, all right, sit down. What the fuck does Richard want? He goes, look, mate, I really like you, you're a good character, you're a lot of fun to be around, but if you don't make me any money, I can't have you here. I'm gonna have to sack you. So you want to go home? Fine, go home. Come back with your head on.. And that, it's 7, 6, 7 years from then. I've never forgot that moment in my life. From that day, I became the top seller in my team. I became, what was it, quarterly president's club. I was flown to Cannes and sailed around Cannes on our CEO's yacht. He's the 6th richest man in the UK, all expenses paid. And then I went on to start my own company. I had that much balls that in the midst of the pandemic, I went and started my own company. And again, these moments are pivotal because without these moments where people really challenge you or test who you are as a, as a man, as a woman, whatever the case may be, you don't ever get to see your potential. And that's where then you get these people who become stragglers. So what do you see as the biggest problems that our generation has? The people you manage, the types of, uh, staff that you manage. What do you see as the problems, the biggest problems from them being who they are now, again, to helping most of the team, the majority of the team reach their full potential when we know that only 20% covers 80% of the team's results? It might be something different in yours, but how do you feel about that? What do you see as the problems in that transition there?

I think the problem is that people bitch about this generation of people instead of embrace it. I think it's just so It's so easy to go, this generation's this and this generation's that. Yeah, you know what, give it up, give it up. There are so many great things about this generation that I love and cherish. So what, it's different, like, get over it. And I've said this for years, like, embrace the generation. Don't bitch about what's going on. Because it's no, it's no, it's not a whole lot different from what was going on before. There's sure, there's macro factors, but you know, every generation bitches about the generation before it. They're lazy, they're this, they're that. It's, it's good. Look, you call my, you call your parents, you call your grandparents, what are they going to say? You're going to go, do you think I work harder than you did? They're going to go, hell no, of course you didn't.

That's very true.

So I, I'm not with that. I think it's, you know, you're, there are some things that you got to do differently if you want to effectively manage this generation of people. But ultimately, it comes down to individual motivation. And I buy into the fact that— and this is Daniel Pink— it's autonomy, mastery, purpose. I don't care where you are. So few things you read in a book actually fucking work. That one does. I think people are motivated by one of those three things in some proportion. Figure out who people are, figure out what gets them going, and do it because you— and motivate them not for yourself, which is so fucking hard. It's so hard to not motivate people for your own self-interest, but try to do it for them. And I— it's hard to do, but you have to. So to me, I'm not worried. You— somebody thumbs up me. You— did you thumbs up?

Oh my God, oh no, it's one of these things.

Oh shit, you got good tech.

Yeah, it does like thumbs up.

I think you just thought it. Oh, that was great. You guys don't see this on the screen. I just got a thumbs up on the screen for some— this thing I was saying. It— to me, it's just like, it's more— it's about individual motivation. That's how I look at it. I don't look at it generationally. It's about individual motivation. How do I figure out what portion of those 3 things an individual is motivated by and try to motivate them best I can to get the most so that, you know, for them, so that I can, you know, have the 5-year compliment.

And how long do you take? How long do you give somebody there before you pull the plug?

Oh, it depends on how flagrant, you know, they are. I can tell you, like, how flagrant the offense is. You know, you don't— the worst thing we do is fire people, but we have to because you got to be loyal to the many, not loyal to the one. But if somebody's late 3 days in a row, first 3 days I've managed them and I've warned them twice, I'm going to fire them. If they're trying as hard as they can and it's a performance issue, you give people longer slack. But at some point it's, can you do the job? And if they can't do the job, then it's not fair to them. I'm not saying anything novel here, by the way, but it's not fair to them. It's not fair to you. It's not fair to the company and not fair to the customer, to all the stakeholders to keep them in a job that they can't. That they can't succeed in.

Makes sense.

So one thing that people are always interested in hearing is how to discover like your why, which is kind of cheesy, but I call it like, I call it your spark. So how did you discover yours? When did you discover yours? Mine was when I made my first cold call after a security job that was like an absolute nightmare. I joined a financial services firm Made my first cold call after practicing for like 2 days. Never made a cold call in my life, but like boiler room, like Wall Street. And when I picked up that phone and started to speak, the entire, the entire floor stopped and was like, who is that Indian kid making that call? And they were like, didn't he just join? Isn't he new? And I loved the attention. I really did.

So for you, what was[No speech] Oh, um, I love your— I like your story. I feel like people have the ability to like sit in a dark room and figure it out. I'm just like, gosh, I'm so envious of you. Like, I can't do that shit. I can't— I can't sit around and think about something that abstract. Like, to me, it's just got— it's got to happen to me. And it happened to you. That's how you realized it. I mean, look, if you can do that, good, good on you.

I just—

I just can't. Um, and so it happened to me. I had somebody that I managed a long time before, and, and to back up, I'm not the type of person— I don't need to be motivated or connect to my purpose, or I don't need that. I, I— people do, that's great. I just have like a standard. I'm like, shit, I'm gonna do this, and if I don't do that, I get a shitty feeling. So it's like, I'm gonna do this thing, I'm gonna wake up at this time, I'm gonna do this, I'm gonna do that, and then I do it, or I feel really, really guilty, having nothing to do with anything else. So I wasn't— I know people need that, I don't. So I never really thought about it. And then one day I had somebody come up to me like, hey, or call me, go, hey, God, we haven't talked in a long time, but you managed me. And by the way, I thought I did a horrible job managing this person. I'm sure I did. But in retrospect, they took one thing and they call me like, hey, you like, I wouldn't be where I am without you. I'm like, holy shit, that feels great. I didn't know that. That's the best. But I don't need to connect to that. Like, me personally, like, I don't need to connect to the why. Like, I can set the standard and feel guilty if I don't do it.

That works for me.

But you don't feel it drives you, like having that internal— but like, you don't— sometimes you can't even identify it. Like, I don't think I've identified Shane Ma, he's why. Like, I can say my daughter, I can say just, um, ego, which is a fact. But yeah, it's hard to identify it and tell, like, you really— like, I've been through very significant times in my life. I've been to rehab, I've been through addictions, I've been on the top of the game, I've been on the lowest of the game. I've been in prison. I've been everywhere. Like, I've been on the best of places. And again, the one thing that does continuously motivate me is knowing that when I come up against adverse times, a lot of people are able to— well, not able, but they say, how does this motherfucker carry on getting up and keep going forward? And that for me was one thing. But then, like you said, when it— when I took out like the selfish approach and always me, me, me, me, me. Becoming a business owner in year 3, one of my staff said, Shane, Sales Driven helped me buy my first house. And again, like, no, that kind of thing for me is like, again, wow. And then my co-founder, he said, like, thanks to you, I'm working for a private equity investor. He's got a fucking jet and I've got the job of my dreams. Thank you. And I get it, but along the way you come up against like some major challenges, significant challenges that usually are quite pivotal in your career or in the development of who you become, who you are. Can you highlight any significant challenges that you went through that could help the audience navigate their own, but a significant challenge that you went through in your life where it was almost a breaking point and you may have gone another way, but something inside you changed, clicked, and you was able to catapult forward?

Hmm.

I want to go back to something you said before, and then I'll answer your question. So it's interesting, I don't do motivation. Like, I don't, I like try to eliminate motivation. That doesn't work for me. Like, I don't need to be motivated. People do. I don't. And I think there are people like me out there where it's like, I'm just gonna Again, and to those people that don't hear this that much, where motivation doesn't click for you, I hope this works, or I hope it crystallizes something in your head. I don't need to be fucking motivated. Like, I, like, hey, you know what? I want to be successful in whatever I'm doing. Let me go look at people who are successful. Let me set standards and let me do those things. Like, period. That's not motivation. That's standard motivation. To me, wanes. I'm motivated today. I'm not tomorrow. I don't want to go in on Monday. I want to wake up at fucking Thursday. Forget that. Like, set standards and live, live to your standard. That is my boring belief on, on that topic. That's not to say, again, other people need to be motivated. Great. Like, do it, whatever you got to do. All right. Significant time in my life where I've had some major adversity and got through it. I mean, look, the, the quintessential answer that every business owner, or most business owners, will give you that lived through the pandemic are gonna say the pandemic. We were broke, man. We were just almost broke. And I remember we were You know, it was April— oh gosh, probably first week of April— and we're having the conversation that every company had, which is like, are we going to lay off people? We're going to furlough people. This is pre-PPP. And, um, and we made that— we were, we were right there. We're like, all right, we're gonna lay people off. And then last hour, 1 in the morning, he was like, you know what, we're just going to take a pay cut across the board. That's what we're gonna do. Everybody's gonna take a pay cut. And we got on that call and I announced the pay cut. People started crying. Talking about how they could feed their kids still, and they're worried we're going to make a different decision. And that moment I was like, holy shit, that was right. That was definitely the right call. I can't believe we even considered the other. And then not 48 hours later, they announced, you know, PPP and what have you. And then things were totally different from there. But, but that, that moment in time and the surrounding survival instincts that kicked in during that time— and obviously, look, the business was the least of the worries of anybody during that moment. But if you, if you talk to business owners like by and large, that was one of the most challenging times of their career. And the ability to lead through that and empathize with people and lead in a way and run a company and, and try to be the best you could be in a way that no one— in a world nobody had ever dealt with before. I mean, you know, you feel like you could sort of manage through anything if you could, if you could get through that as a business. And again, that's the least important thing that happened during that time, but that, that to me was the the, you know, the most challenging thing I've ever gone through in a business setting.

Now, one of the major things of this podcast is right now it's AI enthusiasm, but mainly directed at sales enablement, sales development, top of the funnel, middle of the funnel, and anything below the funnel. Now, I'm seeing a lot of problems in the industry mainly around data. And how bad data is and how long it takes to really clean data so it's usable. Then you've got other problems of— yeah, you may have another, another view on this, but just sales development reps working from home and not delivering on their promise, not being consistent. So then we have another solution that we're thinking about there. There's a ton of problems that I see. Right. And this is the reason I'm aware of them is podcasts like this. I'm able to speak to CEOs, CROs, and them tell me what their problems are. So what do you see right now as one of the major problems in business development, sales development, sales enablement in our industry?

Yeah. So I got a unique perch for this. You know, we're doing sales development, sales enablement for 2,000 clients and ourselves. So the first thing you said, data. Data quality, number one worst offender by far. Um, so much so that we've, we've given up on anything other than calling. Like, we're going to call and confirm. That's what we're going to do. We're not going to find a source. We're not going to do this new tool. We're not going to try this new gadget. No, we're going to call. We're going to call and confirm. That, that, that to me is the future answer, is first-party confirmed data. And we have huge companies on whose behalf we call and just give them a list. Hey, we just want to know for sure, ICP check, bang. I mean, so, and why more companies don't do that, I don't know. But to me, that's, you know, that's gold right now. Um, yes, there's a lot of talk around, of course, AI, it's going to get better. These tools are going to get better. It is absolutely inevitable. I think you're going to continue to have interesting legal consequences and decisions and rules and regs on AI calling. There's already been— I'm not a lawyer, but there's already been a pretty monumental landmark piece of legislation around AI calling. I think that's going to continue to happen ultimately, in my opinion. If it hasn't been legislated out today, which is unclear to me as a non-lawyer, It might be completely illegal right now. Again, not a lawyer. It will be. So if you're betting any money on AI calling, I think you're up shit's creek here real quick because something's going to happen, of course. But not embracing the technology is idiotic. I mean, it's going to be— it's going to rule the tools. The next big issue is that SDRs are have become extremely reliant on email, and email is as hard today as it's ever been, and it'll be harder tomorrow than it is today.

The—

I mean, when I started the business 10 years ago, you could fire off a shitload of emails through outreach and you get a huge response. Now it's like the mechanics and the infrastructure and the domains and the senders and the messages and the this and the IP rotation. It's like, that's, that's impossibly hard today, and it's going to get— continue to get harder. Um, so those are just some observations. And yeah, like, SDRs working from home— forget the accountability standpoint, that's like you screwing up your process and not having good standards for people. But I think the more nuanced reason why it's tough to have work-from-home SDR, especially in our business, is if you get rejected, to turn around to somebody that also just got rejected and give them a fist bump or whatever, like, that's meaningful in somebody's day and keeps them going, versus I get rejected and I'm gonna go you know, watch TV for an hour and dial it back up.

I think that's important too. Are you guys all remote now? Are you hybrid?

Or do you—

are you guys still working in the office?

What's your guys' setup right now? Everybody's here.

Everybody's in the office.

I mean, we— a couple days a week. Yeah, yeah, in the office, uh, depending on department and, um, a couple of other factors. Certain people get— can get a couple days remote, but I'm here every single day.

Wow, that's impressive. I do miss the office. I do miss the office. And I think there is a big thing, like in the past 4 years, I think the— when you're running a business and you're on Zoom calls and you're having those calls, yeah, there's a different— there's a certain element that's enjoyable, but there's something very different about that buzz of getting up, getting dressed, going on the train, getting to work, being in your building, seeing everybody, and like that buzz on the floor. I definitely do miss that. And I don't know if companies have really gotten that back. Like, I don't think it will ever be the same pre-pandemic, but anything equal. So are you guys using AI like with, with your business then? Are you guys using AI? And if so, what kind of AI are you guys using in your business?

Whatever you can share. Yeah, we're using, you know, probably like a lot of people are using AI in a lot of different places. Um, and it's all the way into the, the very like in the weeds of like one of our vendors and the IP rotation to figure out what emails to send off which IPs, which is really in the weeds. And then up to figuring out how can we create a more curated seamless client experience up front where our clients have to give us as little information as possible. You know, you think about client onboarding. You know, in 5 years, we're not going to have a client onboarding where you, hey, let's get on the first call, tell us everything about you. It's like, no, you got on the first call, we know everything about you. Like, here's, here's what we know. So how do you make that client experience more pleasant? How do you write the best possible emails? How do you write the best call scripts? How can you identify, you know, from macro data perspective what we should do? But like, I use AI like this, you know, like identify the weaknesses in this compensation plan. What would you do differently for— like, shit like that is to me— and I'm giving you rudimentary stuff, and somebody's gonna listen to this in 10 years and be like, what a moron he was. But for me, in my day-to-day as a revenue leader, like, tactically, those are the kinds of questions.

What are the—

what are— what are most correlated amongst these variables in sales? You know, I did an exercise the other day, Shane. I think you'll like this. So I think one of the most varied processes in and around sales that makes or breaks sales reps is, is your follow-up process. Okay. And it's always kind of nebulous. It's like hard to identify what the, what the hell are you doing for a follow-up process? So I did this exercise where I gave every single sales rep 4 different scenarios. And the difference in the scenarios was just the date. It was like January 15th, January 20th, January 31st, February 5th. It was like you pitch a prospect. On the day before one of those 4 dates, right? So February 4th, like, let's say you pitched them February 3rd and that prospect said they're really excited, they wanted to go, send them an agreement, all they have to do is talk to their boss, no follow-up needed, and then they ghost you. I'm going to give you a 45-day calendar. You show me what you're going to do over 45 days if they ghost you and they never respond to any of your communication. And I took that and then I rubbed it up against close rates Used AI. So tell me what the trends are here. What are the best sellers doing from a follow-up perspective? And like, to non-salespeople, this is the most boring thing you've ever heard. But to revenue leaders where you have great reps and you have shitty and like poorly performing reps, you're like, oh, maybe there is some variability there. And like, what it told me was tremendous. So, so that's my AI, a tiny fraction of the things we're using AI for.

That's very cool, man. That's very cool. So, and I think it's in, like, it's very insightful when and revenue leaders, executives, CEOs are able to share that because these little nuggets of information, then they're not going to get this from a book. They're not going to get this from a blog. They're not going to get this from anywhere but Jeff Winners. So interesting question would be, where do you think our AI will be? Let's, let's say 1, 10 years is very far. I think there's endless possibilities for 10 years, but let's just say 1 year out from now then. We're at quite an impressive pace. So April 4th, 2025, what do you think AI will look like in sales, factoring in something you just said just now?

Um, I think that you're gonna have almost all of the tools that you use serving up options for next best action. Maybe I'm underestimating, but like, I think that your Salesforce, your Gongs are, are all gonna be just saying like, okay, here's this prospect. I think, we think you should do this based on this data using this channel, press this button to do it. And I think, I think AI is gonna get you 90% of the way there and, and, and sales reps are gonna be clicking buttons. I think that no meeting that you have with a prospect is gonna, is not gonna come with an entire prep packet that's made for you. I think you're gonna know which people pick up the phone, which people answer. Like, not, not what they have now. Like, what we have now is okay, but really know everything about those people, how to talk to those people. I think you're going to be served. I think we're going to be at a point in a year where you're going to be served up everything you need to make decisions. But I, I don't think that AI is— and there's people a lot smarter than me on this— but I don't think AI is going to be selling shit in a year. I think, I mean, you have a lot of provided the legalities there. I think you'll have a lot of the inbound reps who no longer, you know, can— who know, like, you're not going to need people to take inbound calls, I think.

Um, but provided the legalities there, I think that is exactly where it will be. So again, where— again, I'm an advocate of AI calling, and the reason for that is I've seen firsthand how the best can perform. They can still have those inconsistencies. They still have their ego. They still have their own ways. Then you have a large majority of people that cannot call to the ability as your elite superstar performers. There is a very specific set of credentials, of knowledge, of business acumen you need to be a proper cold caller, like a 22-year-old, 23-year-old, 24-year-old who hasn't run a business. Is not going to be able to have the same cold call with a Fortune 100 CEO as somebody who's maybe 30 or 40 and has run a business and does know the operation of that said person. You can educate the person as much as you want, but unless they've been in it before, they won't know. So my opinion on AI calling in 1 year will be inbound lead flow will all be responded to by AI calling. 100%. Outbound calling has too many regulations, so there'll probably be some things that they'll be navigating through that. But in terms of just efficiency and advancement, the ability for an AI agent— the company I'm working for right now, they had— it has the ability to call Jeff Winters and pitch you the solution and 10 other solutions that it's been programmed to, to, to speak about and book a meeting barring hundreds of objections, book a qualified meeting with you in your diary. And if you can save— again, if you can save the 75% margin on, let's just say, $4,000 a month versus $500 or $1,000 a month, as a business owner, are you still gonna favor— in 5 or 10 years, are you gonna favor the human rep or the AI agent as a rep.

I totally get this from an inbound standpoint. I think the outbound calling, there's too much margin for nefarious actors, and I think you'll get nefarious actors and people are going to do bad shit, and then it's going to be— again, it could be outlawed now. I read this, I read this ruling. I don't know, maybe outlawed right now, unclear to me., but I think that'll continue to happen. And all it took once, I mean, from my understanding, it was like AI calling in a political context and there was, and if somebody did something nefarious and they outlawed the whole thing like that, that will happen in business. If it's not illegal now, it will happen in business in no time. Mm-hmm. And then it will be illegal. So do I think AI can do it? Sure. I've heard those calls. You've heard those calls on LinkedIn.

Oh yeah.

Yeah.

Yeah. Or you have a company. Yeah. It's good.

But it's not gonna, but 5 years and then look like, don't, how do you think it'll be in 5 years? Do you think there'll still be, the same type of dynamic of like a very strictly heavily human-labored workforce making cold calls, an extremely inefficient process versus an AI agent that is regulated to perform those calls on the right types of qualified permission-based inbound leads that have accepted AI agent calls. Again, in 5 years, The efficiency play is gonna be major. What do you think is gonna be favorable again to a business owner that maybe not you that is going along this journey?

I think that, I think that often we, and I'm including probably you and I in the same group, like we, we underestimate the impact of early adopters. So do I think in a couple years maybe because it's like we all equate these tech companies with all companies, and it's just not. It's just that we're the loudest. I'm in this group too. Like, we're loud, kind of leading edge on technology, but like, there's a gazillion businesses that aren't that. And I think you're going to have a whole swath of businesses that are like, no, I'm not, I'm not into that. So do I think the technology is going to be there? Sure, the technology is probably already there. It— but do I think the adoption and the regulatory environment is going to be there? No, I think I think you're just gonna, I think you're gonna see it a lot more inside the business, inside the business then, because, because it's gonna get dicey. It's gonna get dicey with selling. You're gonna have nefarious sellers on AI. You're gonna have regulatory issues. So I, I think, I think we're gonna, we're gonna get to a critical mass of AI utilization inside sales and sales development before bad shit happens and it gets regulated to a certain extent. And then we'll have a pretty hard line. And then I think you're gonna see it increase productivity inside organizations operationally, customer success, etc.

I think you nailed it with that one. So another thing I'm an advocate of is getting through hard times. And sometimes there— even today, one of my buddies, I didn't speak to him for like 2 months. He just went super quiet on me, just had a kid, uh, his second kid. And I'm like, yo, what the fuck happened to you, bro? Like 2 months I don't speak to you? I thought you hung it up. And he was like, bro, I was depressed. Well, somebody, a family member died. Having the second kid is being very stressful. And when I speak to him about the mechanisms, the tools that some people like us, business owners who have been, or even just individuals that have been through certain hardships in life, you have a certain kit of tools that help you get through these times. Like, they get you, they help you become more resilient. So for those business owners, founders, executives that are watching you as a source for inspiration and standard sometimes doesn't fit for the regular man or the average person, what kind of habits do you encourage people to inherit to become and remain resilient?

That's a good question. I think people that know me would say that, um, I, I don't care about that many things, like in terms of like making them a big deal. Like not that many things matter to me.

Yeah, but not you. It's not, you know, it's somebody listening. What are the concerns?

No, no, no, I, I get it. I'm gonna land this plane for you. But like, I, I think For me, it's— it's— there is a— if it's not going to matter in a year, like, don't— like, like, don't— don't be concerned with it. I think in general that has helped me and might— and might help others. But like, I— this is gonna sound so hokey, I'm like avoiding saying it. I don't want it to sound fucking hokey, but it's true. Like, I watched— I, I watched this Jocko video all the time. It's called Good. I watched this video and it is like ingrained in my life. And the video on a YouTube video is totally changed my life. And maybe I'm just an impressionable moron, but like in this video, it's like anything bad happens, you say good. Sounds so silly and simple. I agree. Everything bad that happens to me, I literally am like, good, better opportunity for this. Good, better opportunity for— and like, I am constant. Like even at home, I'm just like, bring it. Good. Hey, somebody, you know, kid fell down the steps, broke his leg. You know what? Good. More opportunity for me to show how empathetic I am to my own fucking child. Like, something bad, you know, uh, flight got canceled. Good. More time. Like, I am constant with that. I am, I'm religious about doing that. It has changed my life. I don't know if that's a great answer. I don't know if it's as deep as other guests, but that is my shit. I love it. That's what I do all— did it today.

Immediately.

I did it today.

So would you say that that Jocko video was a motivational video? I think it's— I know Jocko very, very— not know him personally, but his content. I know his content. I know a lot about his content. A lot of his stuff is very motivational. The fact that it's ingrained something in you that is like your creed today— again, this is why all of this content, this video is available because I don't think people retain or digest this type of knowledge in, in the same way as any other channel. Written form, text form, social media form, video, people speaking like this. And after this, after this is said and done and Kathy, uh, chops it up and produces some short-form content, this is where people realize the impact of Jeff. I think that's hugely important, and I, I truly believe the same thing. Anytime something bad— like, I went through a very bad separation last year, a very bad separation. I have a— I have a daughter that's involved in it, and again, I could have been— I could have been one of these dads that just really give it up, go into a hole, go into the bottle. Like, I don't drink alcohol at all, But again, this was one of those times where I had to look at it and say, wow, this just happened, but I really have to find the good in this. What is the opportunity? I always look at it and I say a different phrase, but what is the opportunity in this? Where does the opportunity lie? And that's for me to meet another woman that's good for me, have the life without the stress, right? And there's a number of factors that play into it. So I fully agree with you. A lot of people—

one more thing on that.

Can I give you one more?

Go ahead. Wasn't very motivational. So my counterpart on the other side of the business, I kind of sucked most, like last year, my numbers weren't as good as they should have been. And he's like, look, here's the good news. Somebody could figure it out. Not you, but somebody could figure it out. I'm like, you know what? Somebody could figure this shit out.

Somebody could.

I like him. Somebody could.

That's right.

It went no sugar. That was just right. Boom. Right? And then he's like, hey, good news is somebody could figure it out. You're not, but somebody is. I always think that. I'm always like, somebody could figure this out. Why wouldn't I be the person to figure it out? I can figure it out.

You can.

You typically can. Yeah, it's like, yeah, but the Jocko thing's probably better, I think. Or it's trite, one of the two.

I'm running with the Jocko thing.

So do you think that's good? You think people are gonna think he's a, he's a fucking idiot?

Not he, him. He, no, look, people, people like us with We're very straight, we're very direct, we're very assertive. Yeah. And some people, you've got to realize it and you've got to be okay with it. I think this is one thing I want listeners to realize very quickly, is sometimes you are not always liked by everybody no matter what you do. Sometimes there is a figure or a position you have to play where you're not going to be the good guy, and it's okay to do that. Like, it's okay to be different, it's okay to be very fast thinking, be very ambitious, to have massive dreams, to want to achieve those things, and then It's also okay to be on the complete other side of it. But once you realize that it is whatever you are doing, as long as you're within the lines of like strong, good values, everything will be okay. And a lot of people, a lot more people have to embrace that. And I encourage people to do a lot of forward planning. Anybody I work with, I always have them look and visit your future and then let's work our way backwards. So for you, if you could envisage a future, granted everything goes perfectly for you, this is some wishy-washy stuff, but helps people see a vision. Some people can't see beyond tomorrow, but your vision for 10 years from now, April 4th, it's 8:20, uh, for me. I don't know what time it is for you.

What time is it for you?

Um, 2:20. All right, so 2:20 for you, April 4th, 2034. What are you doing at this very moment in time? Are you still at the Grow Show? Are you still at Abstract? You have 20 kids, you have the same amount.

I have 3 kids now. I might have 3 kids then, I guarantee.

Oh, God willing.

Um, you know, where I'm, where I'm at today, I never— I wouldn't even come close, you know. Like, I— this is a— I got lucky, man. I really did. Some, like, one, I would say 50% of it, I just got fucking lucky. I got lucky people around me. I got lucky stumbled in this business thing. I got— and I've had like a very fortunate upbringing. Um, I got really, really lucky. So, you know, what I want in 10 years, I, I can, I can already start to see with the kids. People got kids know this, like young kids especially, like, like, who are they gonna be? You know, like, I, I don't— there's some— because they're so, it's so formative, these kids. It's a ball of clay. 5, 4 or 5 years old, I don't know, he's gonna be the kid that yelled at me last night at 11 o'clock at night, or he's gonna be the kid gave me a hug at 8 o'clock this morning. So like, I hope that in 10 years, like, I have good kids that have good values and like say please and thank you and like treat everybody great. And if they're going to treat anybody like shit, like, fine if it's me, but like ideally outside of me. So like, that's, that's number one. And then, you know, work-wise, I, I love what I'm doing, um, and, uh, but to me it's all about the freedom to, to be where I want and do what ultimately when I get older. And, um, hopefully I have a lot more people that are giving me those, uh, 5-year compliments because that's at the end of the day, that's what makes me smile.

Do you think, do you think you guys will have exited the business, they'll have new founders, or do you— will you guys stick it out for, for that 10 or even 20 years? Is this that type of journey, or do you think it'll go another way?

I don't know, man. That's a really good question. I don't know. I know, I know we'll keep doing it until we stop having fun doing it and stop, uh, impacting people and people that work here. So I don't know. It's a really—

it's a good question. So if people want to know more about that question, where do they come and find you?

Yeah, come find me on LinkedIn, man. Jeff Winters, LinkedIn, posting content. That's the best place.

All right. And any last words for the audience?

Go check out that Jocko.

No.

And I hope it's good. You do these fucking things, you say stuff, you're like, shit, I hope. If all else fails, go build a pipeline. Seriously, that's the best advice I can give. Like, for people, for business, like, that's my area of the shit I know some stuff about. Like, if your business is— there's something going wrong, like, first thing, go build a sales pipeline. Everything— like, then start the other shit, providing you don't have, like, any major fires. But like most of the time, go build a sales pipeline.

That is the best line in the past 365 days, and I just started shooting this 365 days ago. So I love that.

I absolutely— shit, that's historic.

That was it, bro. That's in there. Because again, that's what I— look, in hindsight, it— again, there's an opportunity because I'm experiencing many, many great things now as a result of it. But The biggest argument and the breakdown of my relationship with my co-founder was that argument there. Build a fucking pipeline, do your job, and we will still have a business. So build a pipeline, guys. Look, thank you. If you guys liked what you saw today, connect with Jeff Winters. I'll have a bunch of links to Abstract Marketing, his profile, and any other things that you're going to share or want to share. We'll have the Jocko link in there, but like, share, and subscribe this if you liked it. And I will speak to you guys again. You sure you don't want to say anything else before we wrap up?

No, man, I said the best thing anybody said on this podcast since you started it. Why would I say anything and screw that up?

And that's perfect way to end it. I'll push stop now and it should