Coaching That Changed My Career with Ryan Garland

All right, I never thought I'd say this, but I don't take notes on my sales calls anymore. And it's not because I'm getting lazy, it's because I'm using Otter.ai to take them for me. Otter.ai lets me invite an AI note-taker into all my sales calls, which not only transcribes them for me, but summarizes them, pulls out sales-specific insights, and syncs everything to my CRM. Oh, and it has an incredible AI chat feature that allows me to ask it any question I have about any meeting. Even if my note-taker wasn't in the meeting, I can simply upload any recorded conversation to Otter. The amount of time it personally saves me is absolutely ridiculous. And that's not even scratching the surface of what it can do for teams.

So I'm super excited to be partnering with them to give you an exclusive offer to get Otter.ai for sales today for free. Go to otter.ai, that's O-T-T-E-R dot A-I forward slash JBSales to get your free offer and start saving time and selling more effectively today. Hearing you speak about the two things that related to me most was, one, I'm super interested in this whole AI thing right now, but two, just the fact that 90% of salespeople we talk to are super fucking lazy. And those two things, realized I had to sign up for your program, and it's been incredibly helpful for me. Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us.

Now, today's conversation is going to be a little different. I'm taking a slightly different approach here. This one is with Ryan Garland. He's an account executive over at Coefficient. But it's not necessarily about his experience in sales that I wanted to talk to him about. I wanted to talk to him about his experience with my training and my coaching. I'm going to be up front with y'all. This is, I'm launching a new one-on-one coaching program, and it's to help individuals because I've, you know, there's a lot of organizations that check out the box when it comes to training. And I know I'm making a difference for at least some of the reps that are in the room, but right now, I don't trust a lot of companies to invest the right tools, tech, mentorship, and coaching to individual sales reps to help them survive what's coming here, especially with AI.

And so I want to really engage with people who are willing to put in the work and give a shit about their careers, about sales, and just about being a better person. And so as I launch this, part of it is to get some testimonials from people. And Ryan was one who took my training, I did a little coaching for him, and the results were, quite frankly, extremely impressive. And so I did the testimonial, really just going to use it as a testimonial. But after I re-listened to it, I realized there was a lot of learning lessons along the way on this one, which is why I'm going to share it here with you all. And I shared some stories based on his experience and some key takeaways. But I thought this was a unique experience to show the audience here and remind the audience that the way I actually get paid and how I'm allowed to do all this stuff and share all this free content is by doing coaching and training.

And with this new program, I'm going all in on the people that care. And I'll even be upfront with you. Look, it's $7,500 for three months. And you get one-on-one coaching from me, you get all my on-demand content, and you can ask me any question at any time through various channels that we'll pull together, and it includes an accountability coach. So listen to this with Ryan, and I would love to get your thoughts and feedback on this one as well. And obviously, if you or you know somebody who needs coaching out there and is really trying to get them to that next level, and obviously has a few bucks in their pocket, send them my way. I'll give you $500 off if you mention the podcast episode, and we can get started as soon as you want.

My goal is to help you reach your goals. As always, I try to put this content out there so that people can skip a few steps, right? Based on all the mistakes I've made. And this one-on-one coaching will help people skip a lot of steps, whether you're in sales, you want to be an entrepreneur, you want to be a solopreneur, you want to do coaching yourself. I got 30 years of mistakes that I can share with you and some cool frameworks that I know work. So as always, I hope you enjoy this conversation as much as I did. Let's make it happen. Let's talk about, let's go background first. So what's your background? How'd you get kind of where you are right now? Yeah, so I, a little bit about me, I grew up in St.

Louis, Missouri, attended Indiana University for college. So went to the business school there, sales and marketing major, went that route because I knew I sucked at accounting and finance. And I kind of liked, you know, going out and hanging out with friends. So that was, drew me to sales. Honestly, loved, loved it from the start. Loved, like the negotiations class I took in college was the first class I took that really made me realize I like sales. Moved to Chicago, started in the Oracle sales training program there, learning top of the funnel sales. But did a year and seven months there and realized no more Oracle for me. I need to go to a startup and have, you know, make an impact on more of a hands-on level and just kind of, I love the unpredictability of the startup world and just being able to make a bigger difference.

So moved down to Austin, Texas, where I am right now, been here two years. I worked for a company called Coefficient. We're about 70 employees now. I was employee like number like 35 or something, third sales hire here. We are a, basically a venture-backed startup based out of the Bay Area that connects business systems to spreadsheets. So we, you know, every company in the world pays for expensive business tools like your sales courses, like your net suites, like your snowflakes. But every company in the world ends up back in spreadsheets, whether you like it or not. And that's Coefficient's whole pitch is, you know, we want to make data more accessible and more manipulative for your rev ops and finance teams.

And so, yeah, it's been a whirlwind. I love the, again, I love the chaotic, chaos and unpredictability of the startup world and kind of the highs and lows. You know, we may need to get a Lexapro here soon just to deal with some of the lows that come around. But yeah, I love it. And that's where I am now. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB Sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process. It also includes monthly workshops that I'll be running on specific sales skills and different tech skills like ChatGVT and how to leverage AI throughout the entire sales process.

Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to JBarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. Well, I mean, it's a funny, a very similar track as me. So I went to Maryland. I didn't know what I wanted to be when I grew up. I got into marketing because I was like, fuck, sure, fine. You know what I mean? I didn't get any of the sales because back then they had nothing in sales, right? It was pure marketing. But then when I got out, I did the big company thing.

So DeWalt, then Xerox. And that's where I was like, I always tell reps, like if they don't know, if you're trying to get into sales, like go get a logo, right? Go work for an Oracle or whatever, because A, they'll train you, right? B, you have a logo so that when you go to interview, like if your first job was this company, half the interview would be explaining what this company does and how does it work, whatever. But when you're like, oh yeah, I worked at Oracle. It's like, oh, all right, cool. You worked at Oracle, right? Yeah. And it gives you that foundation. But then that, I don't know if you felt it the same as I did, is like, I was like, no matter how hard I work here, it doesn't fucking matter.

Like the stock price isn't going to change. I'm not really making a difference in anybody else's life other than mine when I make my commission check. And when I got into startups, I was like, oh, I'm like, all right, like this is, this is A, where I belong because the chaos, I just liked it. But also you knew that you closed that deal, the whole fucking company lives for another month. And it was like, when I knew that my, my, my impact was directly related to the success of the company is when I was like, all right, startups is where I'm supposed to be, right? You just nailed it on the head. Especially like, you know, you're at an Oracle and you know, in the back of your mind, you got to put in the time, like in any industry, like any entry level job is going to suck pretty much.

But then you're 11 months in, there's four directors that actually know your name, no matter how much you actually network. And you want to work harder than everybody else, but you're not seeing any rewards from it. And so, yeah, you just described it. Yep. The other thing that killed me was when I was kicking ass, I was better than everybody else at Xerox, apparently, just because I was doing my job. And, um, so they were like, okay, I was like, all right, well, apparently I'm good to my manager, right? Um, here's my job. Here's the next job. Here's the job I want. Like that, that one looks really cool. How fast can I get there? It was like, oh, well, you gotta spend two years doing this and two years doing that and two years doing that.

And then you get the opportunity. I'm like, wait a minute. So that kid over there who sucks and you make fun of, he's going to get the same opportunity for a promotion from a timeline standpoint as me. Exactly. He's like, yeah, that's the way it works here. I'm like, all right, that's not the way I work. Like, I'm sorry, the, I am, uh, the harder I work, the better my results, the faster I should go and the more I should get paid. Fuck off. That's what sales is. And if that's not the culture here, I'm out of here. I can't deal with this. Precisely. And not to beat a, uh, a dead horse here, but when I found out how they ran the promotion process at Oracle, uh, is what really was like the last straw.

And it was pretty much like a fantasy football draft. Like, oh, this kid seems like he's fun and can drink a beer on six street. Like, let's, you know, let's not look at his numbers. Let's not look at any of that. So it, it is what it is. I get it. Um, it's part of sales, but you know, that's why startups are meant for everybody. And that's why, you know, there's, there's always a place and fit for, for somebody at Oracle. Well, what you'll find just as a sidebar here. And what I realized is there's very few people that are, that are good at all stages of the business. You know what I mean? Like, like Kyle Porter from sales loft is probably the only one I've ever known in my life that started a company at zero and exited a $2.8 billion valuation and acquisition.

And he was there the entire time to CEO. Almost everybody else. Once you kind of get into your mid thirties or whatever, you kind of fit a, I love series A, right? Or series A is a little too chaotic for me. I like it when there's some structure and process in place. So I'm a series B or a series C guy. Others are IPO people. Others are just corporate all the way through. But it's, it's really liberating to all of a sudden, like know where you fit. It's like, Ooh, I'm so fucking good at this part of it. And this is what I love. So now every couple of years, I'm going to find another business that, that I can do that in. Yeah. Rinse and repeat. Yeah. A hundred percent. It takes a little while to figure out what that is, but you, you know, you'll, you'll find on your journey, there's parts of the business that you're like, this is super fun.

Oh man, this, this is now getting wicked boring. And you know, we are now have a huge HR department and you know, all these processes that gotten put in place and all like fucking any of this, like, ah, right. I got to go find something else to do. Yeah. Yeah. That's a refreshing discovery for sure. All right, cool. So got the background. What do you do? Got that. So talk to us a little bit about like kind of what drove you, like what were you doing beforehand and what drove you to look for this training or like when you heard that podcast, like what was, what were you trying to help improve and kind of some of the results that you saw early? Yeah, I think, um, I didn't, I never learned to close at Oracle cause I was a BDR there.

So I obviously every BDR says they, they did, you know, full closing experience, but I didn't. Um, so I joined obviously being sales hire number three. I never got that like true, like core sales foundation. Um, and so I've been the most I had known of it was one through our former head of rev ops, who's no longer with us and, or sorry, head of revenue. Um, and I don't need to indulge any more in that. And then your podcast and then, um, the other podcast that I was listening to, which was 60 minutes, uh, the president's 30 minutes, 30 minutes. Yeah. I don't know how I exactly found you. I think I found your podcast through just wanting to, to find a good sales podcast. And that's how I initially found you and was listening to you right when I moved down to Austin and like that give a shit mentality is what gets me up in the morning, every single morning.

And I could tell just through hearing you speak like that you've, I mean, even after such a long, successful sales career, like that's still your number one value. Yeah. It's like, it's a double edged sword because it, it haunts me at the same time. It's like when you're not able to find success, but you still give a shit that that's what drives you nuts. And, uh, but just being able to keep, you know, have that consistency in that process. I'm only three years into a sales career. So it's like, that's also the other piece of it that drives me nuts is like, I want to go, go, go. Honestly, I had only, I had listened to like three episodes and just like hearing you speak about the two things that related to me most was one, I'm super interested in this whole AI thing right now.

I just, I'm, I don't know if I'm passionate about it. I just think it's fucking insane. And I like learning about it. But two, just the fact that 90% of salespeople we talked to are super fucking lazy. And, and those two things just caught me, um, pretty invigorated by what you had to say. And then I just kept listening and realized I had to, had to sign up for your program. And, uh, it's been incredibly helpful for me. Love it, man. Well, you're, I mean, quite frankly, your give a shit factor will give you a 10 steps ahead of anybody else because the, the lack of give a shit these days in sales is so fucking brutal. Like it, I see it every single day with reps that I train and you know, they sit there, they don't engage, they don't do anything.

They just expect the leads to come to them or whatever. And then they complain when they, things don't go their way. And I'm like, you guys are already just done, you know, like, and I, and I do think, I mean, with AI in general, I think we're in an 80, 20 scenario here, man. Like I, I think 20% of us as in pick a profession, I don't get lawyers, doctors, whatever. The 20% that are like, that give a shit are willing to put in the work and, and like figure this stuff out are going to be absolutely invaluable moving forward. The other 80%, man, are just going to get smoked, like smoked. Yeah. It's a, it's an interesting world, but I think it's, it's the opportunity for those of us who give a shit and are willing to put in the work is off the charts, like off the charts.

So yeah. Across pretty much every industry, I would say. So yeah. Every, I mean, outside of the trades, maybe, you know, like I tell kids who are going to school these days, I'm like, be a plumber, be an electrician. Yeah. Because, uh, AI will still come for your job, but just not yet. Right. Yeah. Um, exactly. I think you have the right approach, man. Like you're right. You know, I get a lot of questions from people saying like, Jesus, dude, like I've been doing this for three years and I'm fucking exhausted. You know, you can wait for 30 almost like what the fuck keeps you going? And you know, it's, it's just that continuous improvement, try to get better, give a shit. And if I was somebody who like tried to sell something that I didn't believe in or care about, I would have been out of this profession.

I'm like, you know, we, you know, when you hear people say like, oh, that person can sell ice to ex Eskimos and all that, that fuck that. That's a piece of shit sales rep, in my opinion. Like, because that means they just don't care. They're just, they just have a really good ability to convince people of shit. Whereas, and that's kind of the B2C world is the distinction I usually make between like the Grant Cardones and the fucking douchebags like that and the Wall Streets and stuff is they're trying to convince people to do something. And the way I look at it is if you're trying to convince anybody to do anything that you're doing it wrong, right? It'll be about helping people solve problems, achieve goals.

That's it. And you can figure that out, man. You can, you can do this for ever. And as hard work as it is, it's the, the, the satisfaction of, of finding that client that you can make the right difference to and fucking, Ooh, right. And then obviously making some money along the way that that's what keeps you going. So. Yeah, no, I'm, I'm, I'm like 70% through never split the difference right now. And, uh, I'm doing the audio book cause I just cannot get my goddamn brain to read anymore. And, uh, and he's talking about, uh, like, like you said with convincing, it's like the red shoe versus the blue shoe thing. It's like, I don't know. There's such a, um, false pretense about sales. I feel like that people are slinging towards right now and just, it's exactly what, you know, you talk about all the time in your podcast.

So it, well, the hard part is, is that it's, it's really hard to justify. If I would just put it the, you know, the right way in the wrong way, if you will, right. The Grant Cardone way versus my, um, it's way easier to make fast money and stacks of cash on going, being a douchebag, right? Yeah. It just is unfortunate going in and really learning the craft and, and, and growing. And it's, it takes a lot longer. It takes, you know, but to me, it's just much more satisfying at the end of the day because you, you know, the difference that you make as opposed to just, yeah, I got my commission check and fuck that guy. I don't give a shit, right? If I never see him again, I don't care. Like that type of stuff.

I tried that up like early in my career. Like I did a couple of that because I kind of fell into the, oh, okay, I can, yeah, I'm pretty good at talking to people. I can convince anybody of anything. And then like, I did it once and I felt like so gross. I apologized to the person afterwards. I'm like, I'm sorry, you don't need this. You need your money. Like, please, I'm going to cancel this contract. That was, I just took advantage of you and I shouldn't have, and I would look back after that. So yeah, you feel dirty. It's like, you need to go take a shower after. Yeah. It's not because it's super hot in fucking Austin. So yeah. Awesome, man. Well, look, let's, let's rip through these. And then I'm an open book for you too.

So anytime, um, that you have questions, I, I tell people like we can, I'll set up a call anytime if you've got specific stuff, but the Instagram, right? If you have a question anytime, just hit me up on Instagram and do a video and be like, Hey John, you know, I'm dealing with this. I'm struggling with that. Any thoughts on this? And I'll usually get right back to you on those. Okay. Okay. IG is the best way to, to reach you. The fastest way. Email. If you want me to review something like, Hey John, could you take a look at this email? Could you, here's my strategy for this deal? Like that type of thing. Then, you know, send me an email, but if it's just like, dude, I'm struggling with this or like, fuck man.

Like I am getting the shit kicked out of me right now. My team is, you know, my, we're series a, I got no resources. You know, my boss is breathing down my neck about this type of shit. Like any suggestions. Yeah. I'll get back to Instagram's the fastest way. Awesome, man. Appreciate that. Love it, man. So any, any specific, so what was your favorite, what's your favorite part of it? Cause I get the two programs, right? Fill in the funnel, driving to close where, where were you like, Ooh, right? Cause you are a BDR. And so you're SDR. So you kind of understood the top of the funnel. But where was kind of the biggest help of all the concept that you went through? I would say the driving to close for me had the biggest impact.

And that was, I'm at a PLG company. So sourcing leads for me, wasn't the main priority that I was focused on at the time. Now things have changed a little bit recently, but the driving to close thing was insane, insanely helpful, especially now that I've, I'm almost done with never split the difference. I'm seeing so many ties to your program in that book. Um, and I just liked that you, you don't overcrowd each section. Like there's, there's one to five points that you really hit on in each one. And there's just small tidbits that I've picked up that I've implemented in my day to day that have made an impact like that. Um, for example, your, your, um, your closing email that you send where, you know, you, you highlight the key objectives and then ask at the end, you know, does, can you just respond back to me that this all makes sense that had an immediate impact on my, on my sales approach.

Um, you know, the other one of, uh, are you still interested? Like there's just, yeah, yeah. That was an all time, brought that one to my manager. Um, so, you know, and then your negotiation training was freaking awesome too. Like I, I think you just do a really good job of taking what you've learned in your sales career and, and like bundling that up into like very knowledgeable and learnable modules. Well, yeah, I appreciate that. That's kind of where, so I took this training from Jeff and by the way, he's kind of getting out of the business, but if you want to see a fucking artist in this industry, man, like I'm more of a scientist, right? I I I'm good, but I'm not like, holy shit. Right.

Uh, Jeff Hoffman. So I think it's MJ Hoffman.com. He's the guy who came up with all this stuff in the first place that give you a scorecard and everything else, but he, he kind of presents it in a way that's like, whoa, look, I'm, I'm the guy that takes that art and puts it to a science so that everybody else can do it in a, in a way that it'll get you, like I said, pretty far, but then you got to kind of be that, that artist that takes it to that next level. But that science and that structure and that process is something anybody can apply if they decide to go through with it. Yeah, exactly. And that's the best part of it is that you can pretty much apply your entire program overnight, which is great.

Love it. So, I mean, any results that you can point to, like before the training, after training, where you're like, Hey, before I was kind of this percent, you know, conversion ratios or whatever it is. And now because of that, I'm like, you said that the company had the best quarter ever, those types of things. So anything that we can pull from that? Yeah, I think I have gotten to be extremely better at negotiating. And I think a large part of it is, is credit to you as well as the never split the difference book. And just like the small what and how questions that I've picked up. The idea that a good negotiation is a mutual win and not, you know, someone, there's no winner and loser. And just the fact that like a negotiation starts the second you get on a call with somebody, just this small shit that you, that you've been able to articulate that like you never really think about when you, when you start in sales.

Um, and so the scorecard framework also huge, um, the give and get thing. I know most sales reps understand that to, to a degree, but I think the number one thing I implemented literally the next day after I took the negotiation piece was, um, the yes and thing that you do where, you know, somebody asked for something and then you respond with yes. And then, and in order for me to get you that I would need X, Y, Z. Um, so just, I think I closed 58 K last month on a 35 K quota. Um, I wouldn't say that's a coincidence. I, that was my best month in the company. Um, so yeah, very, very happy. I love it, man. And you, I love the fact that you pick it up those nuances because that small nuance is the difference between quid pro quo and reciprocity, right?

Most negotiations is if like, yes, but I'll do this versus yes. And now it's in their best interest to give me what I need so I can give you exactly what you want. And that small shift of, of mentality literally makes all the difference in the world. Right? Yeah, exactly. What would you say someone thinking of working with us who's watching this video right now? Yeah, I would say, I mean, no matter if you're six months in your sales career or six years, or you've been doing this thing for 25 years, or if you have the entrepreneurial itch like I do and mostly my father, um, got to watch him grow up and start a business from scratch. And that's kind of my end goal here is to jump over to that entrepreneurial side.

Eventually, who the hell knows what I'm going to sell at that point. Uh, it certainly won't be a software company. Probably not. But, um, I think this, this program can apply to your freaking marriage if you want it to, like having a girlfriend. I think, um, there's just so many ways to pick up things out of your program that will apply to, to your everyday life. And, um, it's stuff that you can institute right away. That's what I would say. Awesome, man. I appreciate that. That's huge. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough. Now to keep the momentum going, it would mean the world to me if you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network.

Also, I am super excited to be launching my new newsletter where I'll be sharing everything I know and everything I'm learning along the way while I'm out there selling every day just like you. Go to jbarrows.com slash newsletter to sign up today. Let's all level up and make this happen together. you