146: Behind The Scenes of Searching For My Next Job With Ashleigh Early

Hello, everyone, and welcome to another episode of Make It Happen Mondays with John Barrows, brought to you by our sponsors, Sales Loft, Gong, and Vanilla Soft. Great companies to work for. We appreciate their sponsorship. On this episode, we welcome Ashley Early to the show for a discussion around becoming an entrepreneur instead of getting a new job. This is a huge leap, and people sometimes don't know when to take that chance. So Ashley's going to talk to John about how she came to this conclusion and what's happened since the leap was taken. Thanks for coming on the show. Ashley, we appreciate you. Everybody enjoy the episode. Make it happen. Good afternoon, everybody. This is John Barrows.

Make It Happen Mondays. Hopefully you had a good weekend. I am sitting here with a very interesting guest who has a very similar background to me, and we are going to be talking some cool shit today about careers and what to do about in today's insane fucking world here. So Ashley, the founder of her own consulting firm for various reasons that we're going to get into. Ashley Early, say hi to everybody and give us a little context here. Hello, hello. So excited to be here. Yeah, I'm excited to have you. And we've been doing this now. Like we've had, you know, usually what we do is we pre-record a bunch of episodes and we just kind of release them on Mondays. But I stopped all that because I wanted everything to be as relevant as possible to where we are today.

And we've been talking about like how businesses are making decisions and all this other stuff. But the reason that we wanted you on this episode specifically was because of that unique kind of journey you've taken on your career and how you've, to a certain degree, reinvented yourself in a very interesting time. Because there's a lot of people right now who are getting laid off. There are a lot of people worried about like their job or what to do and how to do it. And your journey is, I think, is a great example of how to adjust with where we are right now and really understand your core values and your goals and all that other stuff. So let's back up a little bit, Ashley. Let's back up to last year.

Talk us through kind of, you know, we were talking right before this where December is really where this kind of change happened for you. So give us that context first and then let's talk about kind of the components of how you got to where you are right now. Yeah. So just kind of a quick background. I mean, I built, I built my career building and rebuilding SDR and inside sales organizations. So I've been very lucky. I've been able to work with some amazing unicorn companies like, like Okta and FireEye, built and rebuilt other programs at companies like Mattermark, Pernix Data. So really kind of hard tech stuff. And then back in 2018, I decided I needed to get kind of out of that traditional corporate environment for a little bit.

And I moved over to Vendition, which is a great company. They do sales apprenticeships. And I basically ran their coaching program. So my focus every day was to make sure that all of the hires that we placed were successful in their roles. And it was a fantastic experience. I got, let me do, I used to joke, it let me do all my favorite parts of my previous job, but I never had to deal with HR or finance. It was fabulous and things were going really well. Companies still growing, companies still around, nothing but good things to say about them. But I was informed on December 20th of 2019 that my position was being eliminated and it came a little bit out of the blue. I wasn't really expecting it.

Was there any indicators there of that? Hindsight, yes. Okay. But hindsight's always 20, 20, but not anything particularly obvious or big or overt. It did kind of come. Do you mind sharing some of those? Do you mind sharing? In hindsight, because I think that, I want to tap into this right now where reps are kind of, I think, fearful, right? And some of them are feeling really secure because they have good leadership and those type of things. Other on the fence. What were some of, in hindsight, what were some of those things that you saw that were like, that should have been a yellow flag or a red flag? Sure. Do a couple of things. I'll talk internal and external. Internal, I was less happy in the role.

I was getting frustrated. I was feeling cut off and isolated and a little bit like I was on an island kind of pushing, you know, kind of Sisyphus style, pushing a rock up a hill and have a continually rolling back down on me. So, one, I was starting to feel more and more unappreciated. Two, external, meetings were being missed. Calls were being canceled. I was the only, I was one of two remote employees. So, everyone else is at headquarters. I'm remote. Meetings start getting missed. My, you know, things I'm suggesting keep saying yes, but being put off. Things are just perpetually a little bit further down the line. There was some talk towards the end about changing my role slightly, which I was totally in favor of.

But when I pushed back on comp and stuff like that, all of a sudden things kept getting delayed again. So, in hindsight, there was some change going and I completely understand why the decision was made to let me go. The gut, though, like I always think that the internal is more important than the external. I don't know about you, but I remember like we were talking right before where like I got fired from Staples, right? So, my little company, Thrive, we got bought by Staples. And I was like, at first I was really energized because I was like, ooh, this is a new challenge. Like this is, I was kind of bored with what we had built. And I was like, ooh, this is a new challenge. Cool. But, and for six months I was like super optimistic about it.

But then I vividly remember, do you watch, have you ever seen the movie 300? Oh, yeah. Right? So, my husband looks just like Gerard Butler. It's one of my favorite movies. Yeah, it's delightful. I got a man crush on your husband already. No, but, but, but there was like, I vividly remember, because we were Thrive, my little, you know, I don't know, 80 person company to a $12 billion organization. And there was vividly, I vividly remember a time where I sat in my house with, on my couch with my 50-inch TV with surround sound at three o'clock in the morning playing 300, envisioning me as Leonidas and Staples as the Persians. And I was like, I'm going to, and I was like, I'm not joking, stoned off my ass too.

I'm like, I'm going to fucking kill, I'm going to win despite them. Yeah. And as soon as I said that, I should have handed in my resume. I should have handed in my, my resignation. Because that mentality was the wrong mentality and I knew it, but I held on for way too long and then I got fired. Which actually ultimately ended up being the best thing. And it sounds like for you, similar scenario, right? It's definitely a similar scenario. And I'll say this for me, this was the, this was sadly, this was not my first surprise fire. Yeah. 2016, I actually got laid off twice. Yeah. 2016 was not my favorite year, but again, it got me to where I need to be. Actually, those two layoffs got me to Okta, which was a hugely transformative experience, was absolutely fantastic.

But in both cases, I have my own canary in the cold mine, which is my husband. I have an innate ability to see the good in things and see positive. And I stay borderline blindly positive about things until probably a little bit too late. My husband is the one who's called these things. I'll tell you this, the second layoff in 2016, I literally got out for beers the night before the layoff with my husband. And he was like, you know, you're seeing these signs. This is looking really unstable. You should probably start. I was like, all right, fine. I'll call some recruiters tomorrow. Literally the night before I had agreed to call recruiters. And the next day I walk in, I literally just texted my husband.

I was like, well, definitely need to call recruiters. I was just laid off. It's a weird thing. And it's, the other thing I'll say too, just really quick. And this I think is an important thing. Everyone will get laid off at some point. Everyone, everyone, everyone. This is not an unusual thing. It doesn't mean you're a bad person. It doesn't mean sales isn't for you. It just means that opportunity is over. And if that comes as a surprise or it's a traumatic experience that sucks and it's okay to be pissed and to feel hurt and depressed and all those things. But that's all normal and expected and okay. The trick is to let yourself feel it and then let it go. Yep. Because you will absolutely shoot yourself in the foot if you go into your next interviews talking about how the other company did you wrong.

Right. Even if you feel like it, there are companies in my past that they know I am not happy with them about. But you will never hear me say that to anyone else. No. And actually, I learned this from Jack Welch, too. Because he was very, when I worked for him for a couple of months, he, like, I did a lot. I've always been a Jack Welch fan. And everybody gives him shit for being super draconian and slicing the bottom 10% and all that other stuff. But his whole mentality is this. He's like, look, if I let you go, if I fire you, and right now, it's actually better than holding on to you for a period of time and letting you know you're okay. And then when layoffs come and bad economies hit, you get laid off.

And now you have this complex, like, wait a minute, I thought I was good at my job. And now apparently I'm not. Because everybody knows layoffs start at the bottom, right? And they live up. And so what he's saying is when he lets somebody go, he says, you're not terrible in general. You know, you're not bad. You're just bad at this. So go find something you're great at, right? Because that's where I think a lot of us hold on to something that we're okay at because it's safe. And we don't have the, hey, let's go out and do what we really want to do, right? Totally. And I think I, like a lot of people, too, and I know you're kind of in the same boat. My hesitation with that kind of going it alone or doing something risky has always been in my life.

My family relies on me to have health care. Yeah. Straight up. Yep. If I don't have health care, we go bankrupt in two months because of the cost of medicine. Yep. In this country. Yep. Health care. Hold on a story. Yeah. No commentary on US health care. That could be a whole different podcast. But it's something people who work with me, I'm very transparent about. But at the same time, it's also looking at doing these things on my own. It's like, okay, that is a significant cost hurdle for me to do these things. So it's, there are other factors in place, too. And I think a lot of people, it's really easy to hear people say, oh, you need to jump out. You need to take the risk. You got to do what's right for you.

The stars aligned for me and I got real lucky. I'll talk about how kind of the things I did that allowed me to take advantage of that opportunity. But it's also completely okay to know yourself, know your situation, know what you need to do and go do it in a way that makes sense. Yeah. Not everyone can go start their own company. Not everyone has access to the stuff that I've had. And I, I got to where I am now because of the groundwork that I'd laid over the past five to 10 years. So this was not something I could have done even a year ago. This would not have worked. And you even said, like I was looking at some of your prep notes, you know, like networking, right? And how critical, how did you approach networking when you were kind of earlier in your career, if you will?

And, and what was your thought process around it? So you'll love this because you feature prominently in this. So early in my career, I didn't network really at all. You didn't? Okay. I was, when I was an SDR, I was so heads down on, I've got to get good at my job. I've got to figure this out. And I was luckily surrounded by a team of really good people that I didn't really need to go outside the company. So I didn't. And then I was promoted to manager and same thing, found by good people. I didn't really need to go outside the company. Hindsight, wish I had. In the moment, didn't, I didn't know what I didn't know, which was fine. Then I left, that was FireEye. And then I left FireEye. I went to a couple different companies and I realized as I was kind of really going in on my own, I knew what I was doing to a point.

And one day I was working for an Andreessen Horowitz portfolio company. And they said, Hey, we're bringing in this guy, John Barrows to speak. Does anyone from your company want to come? And the CMO sent me and it was, I remember coming to watch you speak. It was like these light bulbs going off in my head. This is all the stuff I've been doing, but didn't know why I was doing it. And it sold me on education and network events forever. So I started going to all the Topo summits. I started going back when they did like these breakfast things. Yeah. Up in that lovely, lovely, lovely, uh, VC row, that hotel, I forget the name of the hotel up there around Sand Hill, but it's stunning place, you know, kind of doing all those sorts of things.

But what ended up happening kind of slowly over a few years was I really took the approach of honestly, mildly stalking the people who I respected you among them. So following on LinkedIn, I share, like, I still share your, um, like I'm fangirling here for if I seriously still share your how, you know, 11 lessons I learned getting drunk and buying a time share in Vegas is still probably my favorite sales blog ever with like everyone I train. Um, but like, you know, kind of following people like you, like Trish Bertuzzi, Lori Richardson, um, just pretty much anyone I could on social media, just little doses here and there, reading blogs, stuff like that. Then when I go to events specifically making sure to go and get my face in front of these people.

So I've met you, I think three times we don't know each other well, but you know who I am. Oh, of course. Which is exciting. Um, and over time, but what that turned into was I ended up having this network of people who knew my face, who knew, I knew what I was talking about. I don't have all the answers, but I vaguely know what I'm doing. Yeah. And then when all this kind of surprise happiness happened, they were my first calls. Hey, I'm in this situation. How do I figure out what's next? And basically what it turned into was the timeline was December 20th. I get the call. Hey, your position's no longer needed. Bush are the best. Um, my in-laws arrived literally the next day for, for, for the holidays.

Um, we didn't tell my in-laws right away because we didn't want to stress them out and it's the holidays. And it was like, okay, we know one thing it's actually is usually pretty good about landing on her feet. Yeah. We'll let it be. And I started having as many of these conversations with these people that I trust and I value and who were so kind to give me time. People like, um, Jamie Diglio, Mariah Tribble, uh, Lori Richardson, Trish Bertuzzi, um, Victor Baglio, James Buckley, all these absolutely amazing, amazing people. And through those conversations, I kind of figured out what I knew I wanted and what I knew I didn't want. And I came up with this like really clear list. One of the things that I knew I wanted, I knew I wanted to continue working from home.

This, I made this transition when I moved to condition, I love working from home. I'm a happier person. My marriage is half healthier. I have a dog. Actually, I'm literally in four hours going to go pick up our second dog. Ooh, look at you. Nice. Nice. Um, you know, it, my life is better and I do better work in this situation. So I knew I wanted to stay working from home. I knew I wanted to continue to be in a frontline directly impacting people position. I didn't want to just do stuff that was super far removed. I knew I didn't want to go back into corporate right now. I didn't want to go take a director or a VP of inside sales, sales development. I still not ready to go back into corporate.

I'm not saying I'll go, I'll never go back, but I knew it wasn't there right now. Um, and I knew I wanted to start building out some new skills. Like, I know, I know how to manage an SDR team. I know, I know how to build a program. I know, I know how to write a playbook and do all this analysis and coach and teach and do all this. I know. I know that I need to start getting some different skills. So thinking. Can I ask real quick on that, on that point? Um, with you identifying your priorities and what you like and what you didn't like, was that part of kind of a bigger picture vision for you as far as where you saw your future or was that really kind of where you reassessed your past and said like, right?

Cause I, cause I talk about the reason I ask is because sometimes people say, you know what? In five, 10 years, I want to, this is where I want to be. And now let me back into what I need to do now to get to ultimately where I want to be, where other people kind of level set and say, you know what? Let me take a look at what I've done and, and, and start to kind of reshape myself a little bit here based on what I like. So what was your kind of approach to, to that? So I'll find the link to it and we'll share it with this, but I'm a huge fan of somebody. I don't even know who gave it to me, but somebody gave me Mark Andreessen's guide to high growth career planning back when I was like my first month or two of an SDR.

And the, the, one of the things that really stuck with me from that was this idea that you, if you plan too tightly, how you're going to get between A and B, you will miss out on all the stuff and all the opportunities in the middle. So I actually intentionally do not like going, I want to be here. How am I going to get there? I hate doing that. It stresses me out. It doesn't work for my, how my brain works. So for me, what I tend to focus, what I've built my career and focused on when I think about kind of what's next and stuff like that is I look at skill development. What, how could I shore up weaknesses that I know I've got as well as what's going to open the most doors for me. Okay. So that's what I, how I kind of approach is what is going to give me the most options.

Like I want plans, A, B, C, D, E, F, G, H, I, J, K. Okay. And then that way, whichever door happens to open, I can decide in that moment, whether or not I want to take it without worrying whether or not another door is going to open. Cause it will, it just does. Do you consider yourself an opportunist? Yes. Okay. How much, cause I'm the same way. Um, I've always said one of my, I probably the thing I'm blessed with the most, if I was, if I've been blessed with something, anything it's, I have a very opportunistic lens in the sense that I can assess a situation with very little, very few data points and make a decision. And usually it's the right one, but I don't, I'm not analysis paralysis. I don't do like massive spreadsheets to figure out like, okay, I got to make sure that every T is crossed and every I is dotted.

Are you in the same boat there? I am. But what I do is it's more like I have the gut sense and my gut's typically right. And I've learned to listen to my gut, but I will then back it up with all that analysis. So it's like, okay, I'm pretty sure this is where it's going to go. And then I, I go all scientific. It's like, okay, that's my hypothesis. Let me do all the data and backend stuff and make sure this is where it needs to be. So I'm terrible at building budgets, but figuring out for how to pay for something. I'm very good at. There you go. I like it. Cool. So keep going. Yeah. So I had all these amazing conversations and basically what kind of, it came down to for me is it came down to like three or four things I really wanted out of my next job.

And I had the discussion with a woman who I now consider a friend and mentor. And she said, you know what? You should come work for me. And I was over the moon, super excited. We're talking salaries. We're talking benefits. And then it comes down, Hey, we actually can't hire you right now. We still want to hire you, but just, it doesn't make business sense. And I completely understand why they made that call. No objection to it, but it became, okay, now what do I wait around for the job that I want that I truly believe is the right next thing for me to do? Or do I, you know, go and start again, go back to the drawing board. And I think within 24 or 48 hours of getting that news that this dream job is it's on hold.

I signed two contracts to kind of, in my mind, I originally signed thinking I would bridge the gap. I would use, do these for, you know, 30, 60, 90 days, keep some cash, make sure I can still pay my mortgage, go from there. And all of a sudden it was like, well, wait a minute, those two contracts together are half of what I need to make every month. Could I get one more? And so I started putting out, like, I just pinged a few people. I was like, Hey, who's, you know, who do you think would be a good person that I could help for a month or two? And within two weeks, I had signed contracts and secured clients for inside sales consulting, training, onboarding, stuff like that. That was 75% more money than I was making in December.

And that covered the costs of the healthcare that I knew I needed to stay on. So my $1,500 a month COBRA payments covered. My self-employment taxes are covered. My, you know, any gear that I need to do, need to, need to buy, you know, I upgraded my internet and stuff like that. Made sure, okay, legitimately got this. I bought the LLC. If you're at all doing your own employment, by the way, just get an LLC. It costs like 200 bucks up front, but you make it back on the back end. It also protects you and all that stuff. Just getting that set up. And then all of a sudden, by March, I made more money in March than any month in my sales career, period. I hear you. Which is a terrifying thing because somehow I got all these contracts signed in February, won the first week of March, and then everything kind of went a little squiffy.

A little, yeah. Yeah, to put it mildly. And I got, I got very, very lucky, but you talk about being opportunistic. I've always said, and I deal with this a lot with hiring managers, where we talk about how talent is evenly distributed, but opportunity isn't. And I'm a huge, huge, huge believer that opportunity is half luck and half skill. You have to be lucky to be presented with the opportunity, but then you have to have the skill to take advantage of it. I got very lucky that I had an opportunity to kind of create this, create this new business in a safe environment. I know I've got employment at some point down the road. So if this doesn't work, it's there, but at the same time, if it does, hey, right.

And so far it's more in the latter category, which has been a pleasant surprise for the imposter syndrome that's in my brain of, oh, I'm, I'm actually really good at this. And I really enjoy this. And one of the things I found I really enjoy about it is one of the hardest things for me going through layoffs and stuff like that is always you devote yourself so entirely to your employer. And then when you're laid off, it's like a part of you dies and you have to grieve it. When you're working with four or five companies, you've got four or five contracts going. And one of them says, hey, we're not going to renew. All of a sudden it actually legitimately is not personal and it's delightful. It's like, oh, that one contract went away.

It's okay. I'll figure out how to get another one. And it's not as big of a deal because it's still 20, 25% of your paycheck. It hurts, but it's not everything. Talk about the different because entrepreneurship, right? It's not for everybody. No. And I had a very similar, like I was, I always say I'm not a, I'm not a, like an ultimate risk taker in the sense that like Chris, like, you know, my, my CRO, Chris Merrill, like he, he is like an ultimate, like he's the guy who lives on his parents' base, you know, in his parents' basement, eating ramen noodles, starts a company because he has an idea, right? Like that's how we started our first company. I'm not that guy. Like I, I've always been like, I need to have some pieces in place here for me to take.

So I always say I'm a calculated risk taker, right? I'm the second guy in the sense that you start the company with that idea. You take that mask of risk, you bring me in and I'll light this thing on fire. Right. And I've always been same thing with like base salaries and stuff like that. I was adamant for the majority of my career. I had to have a base salary. I had to have a base salary because I'm like, what if one month I don't sell anything and and I can't pay my bills. Right. So that was always in the back of my head as a, as a younger sales professional. But then when I had the forcing function of, of, of, uh, Staples fire or Basho firing all of us on the spot. And all of a sudden I became a hundred percent commission rep.

I was freaking out. Cause I'm like, wait a minute here. And I'm look, I'm a pretty self-motivated person. Like I don't need very much to get me out of bed in the morning. Right. But man, if you want some motivation, go a hundred percent commission. Right. And so all of a sudden I, but I, all of a sudden I realized, I'm like, wait a minute. This is fantastic because now I, there is a direct correlation to how hard I work to how much money I can make. So talk about your, the risk factor and the stress factor of working for a corporation like you did for so many years versus now what you're doing right now and, and, and the difference. Yeah. Um, it is a different type of stress. It is a different type of stress.

I would, I personally believe there are very few situations where it is ethical for a sales person to be a hundred percent commission. Um, I've had 10, plenty of people approach me with that. And I just think that the, the risk that the individual is shouldering on behalf of the company is too high. I think it's unequal and beyond that, the amount of time it takes to build up that sales process basically becomes unpaid, which I don't like. Now that said, I think that's something that a lot of people talk about. I understand my companies do it. I totally understand in certain situations. I agree. It does make sense, but I think the vast majority it's. It's companies trying to look for a quick way to get sales, not the right way to get sales, which is, I think not the right thing to do, but for me, it, it came in the form of a couple of things.

Actually, I was talking with some other people who do similar things in there and consulting and stuff like that. And I noticed I approach my contracts slightly differently than a lot of other people do. I think, which is I insist on minimum commitments and part of all my contracts is you get access to me pretty much whenever you want within reason. So I have Slack open all the time. I give everyone my cell number, the whole thing. If you need me, you've got me. I don't bill, but I really avoid billing by hours. I bill by the project. So it's whatever it takes, I will get it done. And I know it's going to take at least this many months to make it happen. If you want to renew at that point, if you want to turn into a role and you have to give me 60 days notice.

So I just roll that need for a, for a salary basically into my contracts. And that I know with a strong degree of certainty, what I am making for the next 90 days. And that just keeps rolling. And that's how I've gotten over that kind of nerves of how do I get that salary? How do I make sure I'm going to be able to pay my Cobra and pay my mortgage and pay this and pay that. At the same time, it's, it's not, it is a different stress. So it's the, you know, and I've, I've heard this before. Everyone says consulting is feast and famine and it really is. I've definitely been in a feast mode, which is great. And I've definitely got, and now I've got one or two clients who have come to me and said, Hey, we're not going to renew.

It's like, okay, great. I am still slammed. All you've currently got me working, but now I know I've got a 60 day clock to backfill this thing. And what's nice is there's a piece of, okay, I've got this. I've done it before. I can do it again. And I did it before without, and this sounds like a humble bracket. It's not in my head. It's actually like a, almost a little bit of a panic thing. It's, I did it before without really trying. Imagine what I can do. If I actually try, if I actually do these things that I'm telling people to do, and I deploy these skills that I know I've got, but I haven't really used much that I've been spending all my time coaching people, you know, okay, cool. I get to put my money where my mouth is and go make this happen.

Um, I actually tried to find my make it happen shirt to wear it, but it was stuck in the wash because I used it for gardening last week. I'm sorry. That's all right. Um, but it's, it's that kind of confidence. Okay. I've done this without really pushing too hard. So if I push hard, I know I can make this happen. And, you know, I mentioned being married and I'm very open about kind of, I I'm very lucky that I've got a partner who understands how sales works and is my biggest cheerleader, my biggest supporter, but is also the first person. Cause he is a very different personality type than me. Yeah. I need the salary. He needs the salary. So it's been kind of fun, not fun. It's been, it's been stressful for us to have those conversations on, okay, so this client just canceled and to see the panic rise in his eyes, they go, no, no, no, it's okay.

I promise I've got 60 days. Are you sure? Yes, I'm sure I can get something else in 60 days. How are you going to get it? Where are you going to get it from? My VP of sales just became my husband who is now doing pipeline checks with me every day or two around what meetings have you had? What's coming into the pipe? And he's using these words because he's been around me far too long. He's like, what, what outbounding have you done? I've requested a couple of meetings. Okay. Well, who are they going to introduce you to? Did those, did those referrals come through from so-and-so yet? Nice. They're coming. They'll get here. Yeah. Love it. So it's, it's been kind of funny how that's worked out. Totally.

Do you think that there's stuff that holds? Cause I think there is a lot of people who are, for lack of a better word, stuck. You know what I mean? And I, and I, and I think right now there's a lot of reps who are sitting home kind of in their job worried that they'll, you know, thankful that they still have one. Right. But kind of taking some time to reassess their situation. Right. How would you suggest those reps right now that are in, you know, in a job, right? It's not when they're super ridiculously passionate about, you know what I mean? It's a paycheck. It's fun. It's not lighting you on fire, but you can do it for at least another year without wanting to die. Exactly. And you're, and you're, you're grateful that you have a job right now in this economy, but there's a but there and everybody has this, but what do you suggest that people, cause I really like the, how you kind of level set and, and reassessed what you want versus what you don't want.

Cause a similar thing happened to me when I got fired from Staples. Like I was, I was in a panic when I got fired from Staples. I had never been fired before in my life. Right. And I'm just sitting and I started the fucking company. So I'm sitting there like, and I was the guy, I was like the cheerleader too. Like I was the guy every, every Monday I would stand up and give the rah, rah speech and everybody can, we can do this, you know, in the culture and all that stuff. And all of a sudden, even though I knew it was wrong, um, like I knew the situation was wrong. I kept fighting and they had to, they had to fire me for me to, and I was like, what the and it took, and I was devastated, but, but then my wife is the one who actually helped me figure this out.

And she goes, well, let's take a look back. I go, cause I'm like, shit, what do I do? Am I an IT sales guy now? Is that what I am? I'm like, for seven years, I've been selling IT services. I'm like, fuck, I don't give a shit about computers. Right. So she's, so I'm like, what do I do now? Right. And she's like, well, let's take a look back at your career. And she's like, why were you the number one rep at almost every job you've had? Right. So let's look at DeWalt, right? Why were you the best rep at DeWalt? I'm like, well, I don't know. Cause fucking DeWalt power tools are pretty bad-ass. And so like, it was, I don't know, it was pretty easy for me to talk about DeWalt power tools and, and right.

And then she's like, all right, well, Xerox, why were you one of the top reps in Xerox? So I was like, well, I don't know if I could, like, I didn't give a shit about copiers, but I genuinely believed that copiers that, that, that Xerox copiers were the best. Right. I genuinely believe that. Right. And then Thrive, my company, like, I didn't care about technology. I cared about the people that I represented and I knew those people were going to do a great job. Right. So after kind of going through that, I was like, wait a minute. She said, look, it doesn't, then it doesn't matter what you sell. It matters that you believe in what you sell. And what that did was that opened my eyes to a whole new world because I was like, now, because I, I firmly believe you've probably heard me say this before, like that sales is the transfer of enthusiasm, right?

Like if you, if you believe in what you sell, right. And if you don't believe in what you sell, I'm begging you, if you're listening to this, go find something else to do. If you don't genuinely believe that what your solution does provides a good service or solution to the right client, not everybody. If you don't believe that, go find something else to do right now. Okay. But, but that changed my view and I started looking around. So how do you, for those reps who are sitting there, listening to this, sitting in their house going, yep, I'm making my calls. I'm doing my thing. I'm kind of in neutral right now. Do you have any suggestions on what they should do? Yeah. One of the biggest things, and I full credit to my dad for this.

So my dad was a sales rep started with AT&T back in the eighties, actually, if I'm even in the seventies, I don't know exactly the dates there. Um, you know, did, literally was like pounding. Like he had a territory that was all of Northern California. When I say Northern California, I mean like Redding, Northern California, not like San Francisco. He had, uh, a, a large town in the middle of an agricultural area and he's selling phone services. Um, my mom hated it there. I know that. Um, and eventually ended up doing if he eventually spent, I spent most of the past two decades, basically worked for companies, various companies that have owned the management consulting contracts for Microsoft.

So my dad was a salesman and was my whole life. And I was raised by that. And as a result, I did not want to go into sales. I was like, I don't want to travel. I don't want to do this. I saw the job and the job insecurity and the paycheck insecurity. And I was like, no, I don't want to do that. Until, of course, I graduated college at the height of the great recession, couldn't find a job, lived in the Bay area and was calling my parents crying, saying I was broke. And my dad said, okay, it's time. You need to, you need to go do this thing. And of course he was a hundred percent right. But one of the things when I was debating why not to get into sales is he had me write down, you had me make a list of all my favorite specific things to do in a day, my least favorite things to do in a day.

Okay. As it relates to work or in general, in general, or in general, but how I would apply it to the situation you're talking about where it's somebody who's trying to figure out, I feel a little stuck. What do I do next? Start by making out a list, like list everything that you do in the day and then push it into one bucket or the other. Okay. So in specific tasks, like the more specific you can get, the better, you know, you don't need to go into like warm follow-up calls versus appointment confirmation calls versus cold calls, but understanding kind of what sorts of other types of activities. And then take a look at those kind of favorite, least favorite. What I would do with that list is go to your mentor, find a mentor.

If you don't have one, I mean, feel free to hit me up. I know tons of people who are always willing to do stuff like this. Most people who are at least five to 10 years in are always more than happy to help out or introduce you to someone. And if they don't have time, um, there's tons of options there, but go to somebody who's been around for a bit, show them your list. They'll be able to tell you kind of, Hey, looking at this, here are some options that you might want to have. And I did this in January as part of my refining process. I was like, okay, so what do I do here are the things I know I want. Here are things I know I don't want. What are some roles that open up that came up? And there were ideas thrown around about, Hey, maybe you should be going into customer success.

Maybe you should be going into building your own training company. Too much my response was, I am not competing with John Barrows. Maybe it should be, you should do your own. Um, you should go and get a job as like a sales evangelist at a sales product company. Maybe you should go do content. Maybe you should go do this, go do that, you know, and it came up with all these ideas. And then I was doing a little bit of research into all these potential different tracks and what really excited me, but it came down to was I, I need, I need to control my own destiny right now. And that was the answer that I knew in that moment. But at that moment, it was like, I've looked at six or seven other things and I've talked to people who were in those roles and said, Hey, what do you think about maybe doing and getting their honest feedback around, Hey, you'd be great at that, but you'd probably hate this, this aspect.

The other side of that is it's also having a conversation. It's way, way, way better to do that work while you're employed. Totally. Not just because paycheck, but because it's a much stronger place to be interviewing from. Oh, a hundred. If you decide you're going to make a shift, if you're going to leave a company, it's much better to go and interview and be like, Hey, I'm only talking to you, Mr. Interviewer, because I'm interested in your company, your product, and this, this specific role. I may be talking to one or two other people, but I'm interviewing because I want to make a change, not because I'm in desperate need for a job. And especially in this climate, that's an incredibly rare and powerful statement.

Absolutely. Now, if you're on the other side, if you've been sadly laid off and stuff like that, you want to still kind of create that aura of, I know what I want in this next position. And here's why. When you're interviewing, you can still do the same thing, but it's, it's just, you have to be a little bit more blunt, but yep. You know, getting laid off forced me to do some, some deep thinking and some networking and some reevaluation of where I want to go. And hindsight. Yeah. It still hurts. I'm still a little bit broken up. I'm still, it's still a little raw. Maybe don't mention that company around me for a minute or two, but, you know, James Buckley, James Buckley actually had the great analogy for me.

He and I were talking about the struggles of possibly starting your own coaching or consulting company. We have to, I think he and I talked about that back in like September, October. And I was like, eh, maybe someday, someday down the road. And I talked to him in December after I'd been laid off and he's like, oh, you got shoved out of the nest. Didn't you? And it really is. It's like a little baby bird got shoved out of the nest. Like, oh, look, I can fly. Yeah. You know? So in hindsight, it's like, okay, I'm glad I got shoved out. The moment I was really pissed. I'm still not thrilled, but it got me to where I am and that's okay. And that's a much, that's the sort of story an interviewer wants to hear.

They hear you roll with the punches, you're resilient, you figure out what you need to do when you go after it. That's all the traits of a good salesperson. That's all the traits of a good, what you're really doing is discovery with yourself. What's the value? What matters to me? How am I going to make this? What's my decision criteria? And that's actually the value piece, I think is, so you talked about what you like and what you don't like. I also think it's imperative that you sit down and you kind of try to understand what you truly value. Like, what are your core values, right? And it's a, I've been trying to figure out a structure of how to help people understand what their core values are.

I don't know where I got mine. Like somebody, I wish I would have remembered either I read something or somebody told me to do it. But like way back when I put together my 12 personal guidelines to success and it was like work hard and smart. You know, everybody says work smart. I said, no, you got to work your ass off. You know, always ask for feedback. What goes around comes around. Like those type of things. And I came up with those. And that lens helped me then evaluate opportunities, right? Because then what I would do is the first thing that I looked for when I started looking for companies was do they align with my core values, right? And then from there, okay, do they have a product or service or solution that I could, I could see myself believing in that made a difference.

And then from there, if you do that for everybody listening right now, if you align your core values, then you go find companies that fit those values and our products or services that you feel like you can believe in selling. I promise you that will come through in your interview when people are interviewing, when people are talking to you, right? Oh gosh. Yeah. And then it just makes such an easier conversation. It's so much easier. And I'll say this coming from what I would consider kind of hard tech. Like I sold the Nectaration Firewall. I can talk speeds and feeds with the best of them. People would come in all the time and they would have no clue what the technology does or how it really works.

That's fine. Do not let that intimidate you. Teaching tech is easy. That's easy. But understanding the theory behind it is typically not. So don't be intimidated by companies that are taking really complex problems and breaking them down and trying to solve them in ways that you don't quite understand. I don't understand how algorithmic security works. I don't. I don't want to. I am not a coder. I do not care. But I do know what that, I can say that I can say, you know, and now I'm blanking on all the speeds and feeds I would normally drop. But you understand the problem that that addresses. Exactly. I understand the problem. I got my job at FireEye because in the interview, I talked about, they're talking about how, you know, security works and stuff like that.

And I brought up that there was a reason they just released a new Die Hard movie. And in it, there was a firestorm, which is basically someone hacked in and shut down the infrastructure grid to the U.S. I was like, oh, so you guys are protecting us against the Die Hard scenario. Oh, I totally get that. And I never get, because the person in the room is like, I haven't seen that movie, but yeah, that sounds right. Yep. I got into hard tech because I watched Die Hard. I mean. I got into, so I got into copier sales. I knew shit about copiers, right? So this is literally, I walk in with my little piece of shit three piece suit at 23 years old, right? To this copier interview, right? And I thought I was just going to meet with one executive.

No shit. I walk into this boardroom. There's six executives sitting there, like VPs, right? Sitting there. And I'm like, oh, fuck. Okay. Right. And the guy goes, he did the sell me your pen shit. He literally slides a copier spec sheet across the table. Right. And he goes, here's the deal, John. I want you to take this outside, sit in the lobby. You got five minutes. I want you to come back in and sell us this copier. And I'm like, what the fuck? And I'm looking at it. I'm like, are you shitting me right now? I mean, and I don't know if you've ever seen a copier spec sheet, but it's like 0.2 font. Like, it's just a billion words on its one page that are just speed. Talk about speeds and feeds, right?

Yeah. And I don't, my memory sucks and I'm not good at, I didn't know anything about copiers. All I knew about copiers, a green fucking button and paper came out, right? That's it. And so I leave, I take the spec sheet and I threw it in the trash. So I sit in the lobby, I threw it in the trash. I waited for five minutes and I come back in and the guy's like, what do you got for us? I'm like, I have no idea. He's like, excuse me? I go, well, I got a few questions for you. And he goes, all right, what are they? I go, do you guys use copiers? He goes, yes. I go, on a scale of one to 10, how happy are you with your current copier situation? He goes, ah, we're about a seven. I go, cool. What would make it a 10?

He goes, well, if it did duplexing and if it's scanned to email and, uh, you know, if we could reduce our costs a little bit, you know, that would be good. I go, cool. I got a, uh, um, a shop around the corner that has some copiers in there that do duplexing, scan to emails and probably could reduce your fees here. So you want to come and check them out? Because I got a few of them, uh, in the, on the copy floor that you can just at least check out, see if they'd be a better fit than what you got. And he said, he literally all six of them looked at me and they were like, could, could you hold on a second? Could you give us a minute? And I'm like, sure. So I leave and I come back in and the guy goes, so when do you want to get started here?

Like, I'm like, whoa, whoa, whoa, whoa, whoa. I have no fucking, I don't even know if I want this job. You guys just put me in an impossible situation, but it's to your point, you can teach skill. You can teach what, what I don't think you can teach. And this is what I hope what everybody's listening to this is, is it, and you, you hear me say it all the time. I don't, I drive and drive passion and curiosity. Those are things that you need to find yourself. Right. And, and, and that's where right now, I think going back to interviewing, if you're interviewing, if I'm interviewing you right now and I'm asking and you got laid off, okay, no fault of your own. It is what it is. I'm going to ask you how you're filling your days.

And if you're like, well, you know, I'm just kind of like looking for jobs, right? Now and kind of right. Like that type of stuff. Like I'm, I'm your, that conversation's almost over. But if you're like, I'm listening, Oh, there's so much free content out there right now. It's insane. Like, you know, Jay Barrows has given his shit away for $99 fucking for, for a course that most people would have to pay a thousand dollars for. Like I'm taking, I took that. I signed up for you to me. I went to these webinars. I went, you know what I mean? Like that type of stuff, like you're developing yourself and you're focusing on yourself. That's the kid that I want to hire. Yeah. And even if it's as simple as like, you know, I took some time, I focused on self-care.

I did some assessments and stuff like that. And now I'm in the process of, I've been applying to very specific companies. I'm not working to get into a few, but here's why I'm really excited about this job and why I'm been, and here's what I've done to prepare for this meeting. Exactly. Well, the, actually, that's my favorite. That's one of my favorite interview questions is how'd you prepare for this meeting? Because I am a stickler for you have, you better have LinkedIn stalked me just a little, like, if not a lot. Um, you, you, you have to do it. It's, it's, it's sales. I'm sorry. Like in my mind, this is like, I, I further, it's really, really hard to assess sales skills, but I can assess your sales skills based on how you prep for the interview.

If you check out my persona, if you look at my background and you've got a targeted pitch for me, for why you are a good fit for my company, if you can sell yourself, then you can sell a lot of, you can sell pretty much anything else. If you don't follow basic sales principles to sell yourself, how do I know you're going to do it with the company? That's exactly what I always say that your interview, that is your easiest and best sale. If you cannot sell your fucking self, then how in the world could I expect you to sell my shit? Cause if you don't believe in yourself, then you're not going to believe from what I got here. A hundred percent. And I'll say as somebody who definitely has some imposter syndrome, definitely has moments, a lot of moments where I'm like, I don't know if I could do this.

I, this is too much. And I'm very uncomfortable bragging. I am not someone who's like, oh, check out this awesome stuff I did. Like if you follow me on LinkedIn, you'll see, I'm not someone who's up there blowing it up. I'm like, Hey, here's what I sucked at today and figuring out how to learn and share. Because if I'm going to make a mistake, I'd much rather y'all can learn from that and don't make it. I recently discovered a great quote from Eleanor Roosevelt said, life is too short to make all the mistakes. So make sure you learn from the mistakes of others. Huge believer in that. So when I'm in interviews, I'm very uncomfortable, like going, oh, here's all the awesome things I did. You know, I don't have all of my performance numbers written down in my memory.

I have them written down in front of me. But what I do have is I learned this really good tip. Actually, this is from when I was in college, um, getting my super nerdy dual degree in political science and opera. I decided for some extra cash to compete on the Miss America circuit. No shit. Oh yeah. Two years, two year first runner up in Santa Clara. Way to get a total of, I think I got a total of about 15 grand to cover my books, which was fantastic. Hell yeah. Not bad for five minutes in a swimsuit. Right. Um, but I was always first runner up because I never actually legitimately got my ass in shape. So I'd always, I'd kill talent. I'd kill interview. I'd kill on stage question. I would be mid bottom of everything else.

I was always first runner up and I was like, okay, that's enough. But one of the great tips they gave to people for interview was every time you walk into the interview or a practice or whatever, know three things you want to make sure the person, the people on the other end know about you by the end of it. Gotcha. So, and that works for sales too. What do you want to make sure they know about your product by the time they finish the cold call, they finish the discovery, the devil, whatever. What are three things you want to make sure they understand? Oh my God. Do the same thing with interviews, but tailored to who they're talking to. So if you're talking to me and you're interviewing for an AE position, you're going to want like the things I will care about are exactly kind of what you said, that you've got the drive that, cause that's something I'm not going to be the one who's going to be beating you over the head with stuff.

I need to trust that you're going to do it and you're going to be driven, that you've got the curiosity. I'm going to look for something that you're passionate about. But then aside from that, I, something I drive really deep into is you have to know yourself and know what kind of makes you click and what doesn't. Where your motivation comes from. So it's not going super deep and telling me your life story about how your mom died when you were a kid. Although if you want to share that, that that's great. I tend to suggest against getting that personal work. It's just a protection thing, but I need to know that you've got that motivation. And that showed up for me when I'm interviewing. It's like, look, I'm responsible for my, my family unit.

I've got two dogs and a husband who rely on me. You better believe I'm going to bring home enough to keep them comfortable and just try and stop me. And that's all I say. I don't need to do anything more than that because usually you can look in my eyes and see when I say that, I mean it. So it's understanding those little things. If you know, I care about motivation. I care about those things. Great. Then that's what you make sure that you work into your conversation with me. Then you go in your interview with John and you're going to bring in two or three different things. So, I mean, I'm, I'm a huge fan of writing things down. I come into interviews with like a page of prep devoted for each person.

The three things I want to make sure they know about me, any sort of connections that we've got. Oh, we both know. So-and-so we both went to these, any sort of any schools, skin connection, stuff like that, as well as three or four specific questions for that individual. And that's something, I'm not a huge stickler for asking questions, but try to have something. Oh, I am. Well, I should be clear. You have to, the only reason I say I'm not a stickler is because I've done enough of these panel interviews where they've asked all their questions and I'm the last one. But in general, try to have something specific to each individual, even if it's just like, hey, you were at this company, what's your, what's the experience that sticks out in your head?

Yeah. The two ones that are almost automatic cross off the list for me are when I ask you, how'd you prepare for this? And you, you can't give me a good example. And then what questions do you have for me? And if you have no questions or the typical vacation bullshit questions, whatever, like the conversation's over. It really is like, it'll be a short interview. So let's, let's finish up with one more thing. The other side of sales. Talk to me about this. Because one of the things that, that you and I definitely align on. Uh, is the bro culture or the frustrations with the bro culture of sales. And I know this, I know your podcast is, is about, you know, the other side of the bro culture. So talk to me a little bit about why you, why you created it and what it's all about.

Yeah. So Casey and I, um, Casey Jones and I started a other side of sales back in August of 28, 2019. So we actually just hit our one year recording anniversary, but we're going to hit our releasing anniversary later. And it basically came out of a frustration of her and I almost at the same time, but ominous to the other being invited to be in a book that we then discovered was 90, I think 95% male and like 3% non-white. And so Casey backed out of it immediately was like, no, thanks. I said, yes, did the interview and then realized, I don't like this and had to back out. And at the same time, looking at all the podcasts and everything on there, we're like, hmm, there's a lot of white guys on this list, a lot of white guys.

And there's a few women, um, a huge shout out to Bob Giamanko and Lori Richardson and those who are really trying to put out a lot of more supportive female content, girls club, uh, uncrushed, all that stuff. It's all getting better, but it's not really there yet. And that led to Casey and I having a conversation kind of, and what came down to our format, which is it's half, so every other week is an interview with someone who is an incredible sales professional, but who's probably flying a little bit under the radar. We bring in some big people occasionally too, as we just had James Buckley on, who's fantastic. I keep bringing him up. We'll get you on there at some point. Um, and the other, but a lot of just amazing people who you probably don't see a lot of because women and minorities we know are less vocal on LinkedIn.

They're a little bit more wary to stand out because you know, the, the long blade of grass gets cut, so you don't want to stick your head out a little bit too much. And having been in those situations ourselves, Casey and I are like, okay, so we got to highlight people, give them a safe place to share their stories so we can create representation and try and change this dialogue. At the same time, the other half of the episodes are Casey and I talking about basically what life in sales is really like. So it's, it's actionable. We try to keep it, you know, things to do, but at the same time, it's topics like, should you wear high heels to work and how to create a sales routine. And we just did one the other week ago about, I mean, literally because I had a rough day and I was like, Casey, I don't really want to record today.

I just, I'm a little upset. She's like, great. Let's talk about how to get through a midday breakdown. There you go. That's a good idea. There you go. So it's a lot of, it's, it's kind of, like I said, half these amazing sales professionals who probably don't know about or should, and half these kind of trying to be real world conversations. And we're actually starting now to get nominations from our audience, which is super exciting. But the other thing that we're doing, which I'm super excited about, especially for your audience, is we've actually recently launched the state of sales survey. And this is a survey that we're doing sponsored by Vanilla Soft, Sales Loft, and Bravado. Huge, huge, huge thank you to them.

But it's the first survey specifically focused on the experience of being in sales. So it's half demographic questions. So we can get a better sense of what this community really looks like. And it's half experience questions, looking or diving into what a day in the life is like. And specifically around if there are any experiences of harassment or discrimination, if there are, what does that look like? Because one of the hardest things we know about the bro culture is it can be very insidious. And it's very, very easy to say, oh, well, I'm not sexist. I'm not racist. So that can't be the culture that's on my team. It's easy. I've done that. I'm a woman. I can't do this. And then it took me a minute.

I've had a couple of experiences as a manager. I was like, oh, I'm only incentivizing my team in a way that incentivizes maybe two of the four people on my team. Because I really made it a point to hire diversely. It took one of the women on my team. I did a cash spiff. She's like, I don't care about a hundred bucks. But if you send me home to my kids early, duh, duh, okay, great, easy. But really trying to talk about what those sort of experiences are like. And we're trying to get as many people as possible to take it. So you can go to othersideofsales.com, top right corner, there's a link to the State of Sales Survey. Please, please, please take it. The more people who take it, the better the results will be.

We're getting these results professionally analyzed. We're going to be sharing it far and wide to help sales products, sales technologies, and just the community as a whole better understand kind of what life is like for us, as well as how we can better support each other as we keep growing this profession. Because one of the things that Casey and I are both super, super passionate about is this is, and I know you said this too, John, sales is the best job in the world when it's done right and the worst job in the world when it's done wrong. And especially in this climate where everything is tense, where everything feels like it's going against us as a community, this is exactly when we need to route, we need to stand up, we need to be counted.

We need to say, this is what my experience has been so that those of us who are fortunately in a position to hopefully start steering the ship in a different direction or making course adjustments, we can actually advocate on your behalf and do it. So othersideofsales.com, click the State of Sales Survey, take it, share it. The more people we can get to take it, the better. It would be absolutely huge. And this is for everybody at any stage in your career, whether you are six months in or 60 years in. I'll tell you, you know, and you know, you know, the We Need to Talk webinar that I did with Casey and all that stuff. When we did that, I always said, I thought I was a pretty empathetic man in general.

And like history, like my wife, I'm sorry, my mom, I think she raised me pretty well. And then, you know, through my whole life, whatever. And then all of a sudden I had my daughter and I was like, whoa, wait a minute here. Right. And I started seeing how they were marketed to differently. And we were, you know what I mean? And all this other stuff. And I'm like, wait a minute. So I figured I'd be, all right, now I'm more empathetic. Right. And then we did that webinar and we did a survey and you might actually, I don't know if you've seen it. Have you seen the Excel sheet? Yeah. I don't think I've seen the Excel sheet, but I've seen some of the right up there. No, if you go to we need to talk.com, you'll see the spreadsheet.

I'm sorry. If you go to Jay Barrow's, we need to talk. I actually up-deloded the spreadsheet to it because what we did was we didn't want to do a webinar on us telling you this is what to do. We said, hey, audience, what are the challenges? So it was a, it was an anonymous survey. Excuse me. It was an anonymous survey that said, give us an example of something that you're like a question that you have that you're afraid to ask, right? Because you're in an environment, whatever. So it's anonymous. So don't worry. Like what question do you want to ask? Then give us a scenario that you've faced in your career that has been awkward or something like that, an example. And then give us an example of like a positive thing that has happened, right?

And when I tell you right now, I mean, look, obvious sexism, obvious sexism is obvious sex, obvious racism is obvious racism, right? And there's nothing you can do about it. Like people are asking like, hey, what do I do when I have like a blatantly sexist boss? I'm like, just fucking quit the job. Like there's no way you're going to change a blatantly sexist or a blatantly racist person. You're just not going to do it. Okay. And I'll say this. I want to throw one thing out there. The most sexist experienced in my life, other than like the creeps hitting on me occasionally, which, which happens rarely, but it has happened a couple of times. I'm very lucky. I've got a wedding ring, which I think blocks a lot of it.

But the most sexist thing has ever happened to me was a woman on woman. Was it absolutely, it was a female leader limiting my potential and pretend. And I don't even think she was aware she was doing it. Yeah. Well, I, it took getting out of, I was like, oh my goodness, that's terrifying. Cause it didn't even occur to me. Casey had a really interesting point on that. She's like, there's a generational component that I realized that with women. Right. And in the sense that the kind of generation above my, like, so I'm 44, right. The generation kind of slightly above mine. Right. I guess you could still consider them gen Xers, but probably whatever. Right. The older Xers, younger boomers. And, and there was, there was really, if there was a room for a woman at the table, it was one seat.

It was one, it was, it was mad men. And okay. It was so, so therefore it was all about like, I got to go get that seat. I'm sorry, everybody else. Right. So, so I don't know how old you are, but if you're close to Casey, what she told me, she's like, I've never really had a woman mentor. I've never had a senior woman mentoring me and helping me because when their, their generation, it was all, it was all, I got to go get that myself. Sorry, everybody else. This generation, right. The kind of gen Xers and stuff like that realize, okay, we need to help this. So, I mean, I think there's a lot of millennials right now that are in a really good position to have more experienced mentors, helping them navigate this mess.

Right. And it's just interesting how the different generations react to each other. Cause I, I experienced that. I mean, I had Lori, Trish and Casey on a, on a, on, on the thing. And I'm like, and I'm sitting there like, why is a bald white dude part of this? Because I'm like, I'm the man, you know what I mean? Like if you fucking, if you really paint the man, it's me. Right. Maybe. Well, yeah, but I've, I mean, I've always been, I've always been promoted based on all the stuff that you get shit on for, you know what I mean? Like I'm aggressive and that's great. I, you know, I dropped the F bomb all over the place. Well, that's, you know, that's just John B and John in Boston. You know what I mean?

Like, right now, but you're a bitch. You're too aggressive. You're, and, and those that I always tell any dude who thinks that it's not a problem anymore, go read that spreadsheet. Go look at the, the questions because it, it wasn't the overt sexism that struck me. It was all the little shit. And, and, and from somebody who's in it, that's the stuff that wears on you. You can write off. Like, I mean, I, like I said, I've had people literally make, I've never experienced anything too terrible. I'm very, very, very lucky in that sense. The most, the worst I've got was a guy drunkenly at a conference starting to talk to me about how basically how he and his wife sleep around together and starting to slightly imply that I should join in on this.

At which point I very promptly was just like, Hey, I see my boss signaling for me, walked over to my boss and said, I'm uncomfortable. I need you to go run interference for me. And he did it in a heartbeat, which solidified good man. I'm going to keep working for this guy for a while. It meant everything to me. That was easy to get by. The hard stuff to get by were the little things that are so incidental, you can dismiss them. And that's, what's hard. And that's where, like, I talked about this, this woman on woman experience. It was so many little things. It was, why am I the one who's being asked to take notes? Why am I, literally that simple. I was the note taker at every meeting. It's six months and it didn't reoccur to me.

Wait a minute. Everyone else's room is a guy. Why am I the one taking notes to, you know, me having to do more reporting, more, you know, I getting all this inspection, I'm getting all this additional work we get. I'm not getting, you know, whatever. Promotions or any of that, you know, recognition. And if I pushed back on it, it was, oh, well, you're paid more. So you should do more, which is like, okay. But again, it's this, those, all those little things. And it literally took until I left and kind of going through the trauma of a not brilliant departure going, oh. And it literally, again, it was my dad. I was talking through, talking about this through my dad. He's like, how many men did she hire since she started?

Five or six. How many women? None. Click. Yeah. Yeah. Great. Okay. You know, and it, I, I got it. Cause again, I think it was a bit of that generational thing where I was looking for a mentor and I'm running at her going, teach me, teach me, teach me. She sees, she sees someone coming at her with a knife. Right. Right. And I understand. And it's sad that that's the way it worked out. But the other thing I'll say too, is it is a lot easier to get mentorship. I've been lucky. I'm a little bit younger than Casey. I'm 33. Okay. I'm enjoying my Jesus year. Apparently that's a thing. Um, I could be eager to be to go into doing that, but it's been easier for me. I I've had women who I've seen as role models.

I wasn't comfortable going up to them being like, Hey, please be my mentor. Tell me things. But they were there. And it was never this sense of, I had to fight one of them to get a position, or there were three women who were up for one role and it's which one of us is going to get it. Um, in fact, in every situation where there's been multiple head counts that I've been involved in going for, it's always been women. I don't, that's the other thing. I don't think people understand people. I think a lot of people underestimate how competitive women can be. Oh my God. God. Um, we will cut you in a ditch. Yeah. My wife will cut me and leave me in a ditch. There's no question about it. If you trigger the mom, a bear response, no shame.

No, no. And we won't even tell you what's coming. Nope. No, you're sneaky. You're sneaky competitive. Guys are overtly competitive. Women are sneaky competitive, which is why I love dealing like, and I've always been very comfortable on guys. Even in high school, my friends were guys because it's like, okay, no BS. None of this. If you have a problem, let's punch each other in the face and get beyond it. We're good. Great. Right. Girls will hold on to stuff for years. Yeah. Um, and to this day, like there are three people, three, that's it. That if anyone asked me questions about them, I will not say anything. That's it. It takes a lot to get to that state. But once you're at that state, you are dead to me.

I'm right there with you. So it's kind of funny when I hear people like, oh, women aren't that competitive. And I'm like, maybe if they did sports, like that's the other thing I tell people that drives me nuts about this kind of bro culture. I love working with bros. I love working with bros. They're so easy to handle. They're, they're just, they're, they're, it's so transparent. Like I always say like dudes are like, it's like the comp, the, the, the, um, comparison of like max versus PCs, right? Like women are like PCs, men are like Mac. Like we just turn on and we kind of work where like max, like PCs, like are pretty complicated or it's like dogs and cats, right? Like dogs, men are dumb and loyal and pretty fucking obvious with our intentions, right?

We're just like, uh-huh. Okay. You know, that way. And it's, and it's, so to your point, bros are actually pretty fucking easy to figure out because all you got to do is play to their egos and giddy up. You get pretty much whatever you want. I mean, you got to deal with the grossness of it. Now, thankfully I've gotten to my point in my career where I can, like, I don't give a fuck about, you know what I mean? I'm not looking for anything from bros and, and I, and I, and I'm now in a position where I can tell them to fuck off. I mean, I always kind of have been, but I always like, there was leaders that I was like, that guy's a douche, but I just don't feel comfortable standing up to that guy for what he's saying right now.

And it just felt uncomfortable. Now I'm like, fuck it. I don't give a shit. You know, and I, I hit that point, um, actually about three years ago because I met one of my VC idols. So one of those, you know, never meet, never meet your heroes. Um, this is a guy who, except for you, except for you, but, um, no, this guy, I'd read about him in a book. It's kind of brilliant. This is great. I had an epic legendary sales leader in Silicon Valley. And he was in, he was, um, on a panel that I organized and I met him. And within 30 seconds of meeting me, he says, you're one of those snowflakes who voted for Clinton, aren't you? Oh my God. 30 seconds of meeting me. All I've said to this guy is, thank you so much for coming to this event.

I'm really looking forward to hearing you speak. And it's like, see what, excuse me? Um, Hey, how I vote is none of your business. And of course, in the moment, I'm just like, ah, so would you like some, can I get you a beer? And it stayed the whole night. Um, the panel was interesting. Um, afterwards he found himself surrounded by all the younger SDRs and just, you know, kind of hanging on on the, on all the young female SDRs and AEs ended up going out to a bar with him afterwards. And of course, you know, it, it's a, I kind of hit a point there where I was like, okay, a, I really wish I had said none of your business. A, you probably would have respected that and been like, okay, fine. But B, it kind of, I hit that point of like, I, you don't have to change it because you can't, but you can at least call it out.

And if they listen great, and if they don't, then you can move on, but at least, you know, you said something. I, I hit that. And ever since then, it's been a lot easier. So I'll, I'll try and be like, like, there's been a few points. And recently I was talking about the hiring manager, like, okay, I want nothing but people who've graduated college, played sports consistently, or done this, you know, kind of the classic, they're clearly looking for pros, which is, I understand. So I, and it's just, I've gotten very much more comfortable now having that conversation of, okay, so are you aware that if we go for that profile, you're going to end up exclusively with white guys? Oh, that's a good point.

We care about diversity. Great. Okay. So let's talk about how we can maybe expand that profile a little bit. What are the characteristics you're looking for? We want somebody who's competitive. Okay. So let's look at people who've done door-to-door sales. Let's look at people who've done any sort of music or theater. Let's look at people who have compete, who have been in the military. Let's look at people who are brilliant at something. They have to be good at something. They don't care what, but something. Okay. That totally makes sense. Let's do that. Okay. You care about education. Okay. So you want a college degree. All right. Are you aware that also is going to skew more upper class people who have come from an affluent background, which can be good and bad.

Are you aware of that? Oh, that's a good point. Okay. What if we open it up to people who've been working consistently since they were 18? There you go. Okay. That makes sense. Okay. Great. Because that way, then I, and I told him, like I would, in many cases, and I've hired Ivy league, I've hired several Ivy league. They're all brilliant, but I would much rather in many cases, if I'm faced with an Ivy league who has questionable motivation or is still figuring out what they want to do to change the world or somebody who's been busting their ass at men's warehouse for five years and is the number one rep in the state of Michigan. I will take them into warehouse rep every day of the week and twice on Sundays.

I'm actually biased against the elite kids in elite school. I got to be honest. I think pedigree is fucking bullshit, especially if you went to college and then went and immediately got your master's degree in something without going out into the real world and figuring it out. Like I actually have a bias against that. I'd rather have the state school kid and it's probably because of my background, but I'd rather have the state school kid that, that got a 2.5 through college, but worked their way through college and mommy and daddy didn't pay for it. I'll take that all day long. My old boss who I can't, there's one, but you said there's a group of like three people that are on your shit list.

And once they get there, they'll get off. One of my old bosses is on that list, but he did say something that I always appreciated. He said he wanted his sales reps to have a PhD. And I was like, what? And he goes, poor, hungry, and driven. That's what I want because those people will die for you. He goes, the other people, like the entitled people where everything has been given to them, they're entitled. Yeah. They worked hard through school. Don't get me wrong. And they're smart people and all that other stuff. But if they haven't faced diversity, if they haven't faced challenge, real challenge in their life, it's going to be hard to face that when you get a job. So, yeah. And so, and that's the one thing I'll say.

I agree. You got it. Entitlement is the massive turnoff for me in interviews. My favorite interview question to ask is tell me about the last time you screwed up. Yeah. Because the biggest thing I'm looking for, I'm going to tell anyone who ever interviews with me, the biggest thing I'm looking for is what did you learn from it? Yeah. What were the consequences and what did you learn? Yeah. And you better be able to come up with something quick. Yeah. Because if you don't come up with something quick, I know it's BS. Totally. It's like, oh, yeah, I totally screwed up and I double parked yesterday and got a massive ticket. Great. What'd you learn? What'd you learn? Yeah. You know. Don't do that again.

Yeah, exactly. So it doesn't have to be anything groundbreaking. But the biggest thing I like about that is A, what'd you learn? But B, it shows me a sense of agency and control. Like, hey, I've screwed up. I took risks. I make mistakes and I learn from them and I move on. A lot of the people I've hired from Ivy Leagues, one of them got in and actually there's this very specific person I'm thinking of here, went to an Ivy League school, parents of Ivy League, Silicon Valley royalty. Legit Silicon Valley royalty, like multiple IPOs, like breeds horses herself on the weekends and she's in her early 20s. But the hardest work I've ever seen and hides the fact that she's from this family. She applied with her middle name on her resume, not her last name.

The whole thing. Like, she doesn't tell people she's from this because she's like, no, I'm going to get this on my own. Her parents instilled in her that drive to whatever. And like, I finally figured it out in the interview. I'm like, wait, you're so-and-so's daughter. Yeah, but I really try not because I'm going to do this on my own. I was like, I love you. Yep. I love you. Come, come, come. I will not spill your secret. Come with me. But it's that sort of thing. So you got to dive in. And this is where the really good interview process comes in. You've got to make sure you feed that connection if you're from. And kind of the same thing. Like, when I work with programs, like, oh, we only want to talk to people who've gone to a good school.

I'm like, great. What sort of degrees do you care about? Oh, maybe they should have engineering degrees. Okay. Why? Because our product's really hard to understand. Really? So what if I told you that I have two completely irrelevant degrees and I've sold technology that's more complex than this? And by the way, don't you have sales engineers too, right? Like, don't you have fucking smart kids on your team that we can actually leverage? Yeah. You know, and God, this is one of my biggest things. I hate programs that are insisting that SDRs learn, like, really deep in the tech. No. You don't. It just confuses them. The more you learn, the more you know about it, the harder it is to sell it. You need to know enough to be able to ask the right questions and understand the problem and make the connections.

That's it. Yeah, it's your job is just to, I really need to get a better analogy than this, but your job is, especially as like a frontline appointment setter salesperson, your job is to get, is to act like the drug dealer on the corner. Give them a taste, get them addicted and hand them off. Hand them off, yeah. Understand the quick need, right? And if you, the deeper you know this stuff, the hard, the easier it is to get pulled in these really deep technical discussions where you will get schooled because you're calling people that eat, sleep and breathe this stuff. Yeah, like you just, you can't do it. You can't like, again, yeah, it's interesting. And I understand the desire. I understand why the companies think there, but it's talking to these leaders who are not sales leaders, talking to these CEOs, these engineers, CEOs and stuff like that, and explaining to them, you know, I get why you're thinking this, but let's maybe try it my way first.

And if you want to try it your way, that's fine. Maybe we'll hire two people, one kind of on your profile and one person on my profile. And I will train both of them with the utmost skill and hustle that I've got. But I get an extra couple hundred bucks if my person does better because I'm usually right. Awesome. Well, Ashley, we went a little long on this one, but I think it was because the conversation was so good. And so we're going to wrap this up. What do you want people to walk away with? Or how can people get in touch with you? I know you said the other side of sales survey. What else? Yep. Feel free to hit me up on LinkedIn. Feel free. That's probably the best place to get me. My website recently got taken down, so I'm rebuilding that.

But that'll be ashleyearly.com. You can always email me, ashley at othersideofsales.com. Make sure you spell Ashley the weird way, A-S-H-L-E-I-G-H. But LinkedIn, Twitter, Ashley at work. Please, please, please, if you take away anything from this one, just because the last job didn't work out doesn't mean the next one won't. If you're not certain about that, please reach out. I'm more than happy to jump on and give you a pep talk or help you figure out whatever's next. I do that for free all the time. I enjoy this sort of thing. I've been there. I've done that. I've got the t-shirt. And you will get past this. And please take the state of sales survey. Share it with your friends. Share it with your sales group.

The more people can get to take it, really, the better. And it is completely anonymous as well, except for at the very end, if you want to put an email on it so you can get results. Other than that, it's completely anonymous. So please, please, please take that. And don't forget, maybe tune in to other side of sales. New episodes drop every Sunday. You never know who's going to show up. Yeah, exactly. I'll be on there if you guys have me. But obviously, I want to tone down the bald white guys on the show. So I'll wait for the time where it's like the percentage is right so we can get a good conversation going. We'll make it happen. Exactly. Thank you. Awesome, Ashley. Well, look, thank you so much for coming on.

Hopefully, everybody, you got as much value out of this conversation as I do. And Ashley, good luck with this journey you're on here because I'm glad to hear that you're in a pretty good position now. You got 60 days, though, right? Get that fire going. Everybody's looking for help. Yeah, yeah. I was going to say, so what's the last part? What's the profile of, like, real quick, what's the profile of who you help and what you do? Anyone who's looking to build or rebuild an inside sales program, especially small startups. So you're hiring your first SDR. You're hiring your first SDR manager. You're trying to figure out how to make this thing work. My specialty is helping you figure out exactly how to do that.

If that means bringing out an outside firm, I'll help you do that. If that means building out the playbook internally, I'll do that. Hiring, acting as kind of a temporary SDR manager, all of those things. But really kind of early, early stage programs is where I can add the most value, the most bang for the buck. Cool. We'll reach out to her. Again, it's A-S-H-L-E-I-G-H, early. And Ashley, thank you so much for jumping on here. I really appreciate it. Everybody else, thank you for listening. As I always say at the end of all the podcasts here, go out and make somebody smile today. Because even if you had a shitty day, if you made somebody smile, you know you had a great day. All right, everybody?

So hang in there. We'll all get through this together. And yeah, make it happen. Thanks, Ashley. Thanks. We'll see you next time. We'll see you next time.