Adam Sockel (00:01.615)
You're listening to Bold Calling, a podcast presented by Orem where every episode we're bringing on the biggest and brightest minds in the tech and sales industries for discussion about their biggest challenges and the unique ways they're working to solve them. I'm your host, Adam Sokol, and today I'm joined by Will Aitken, co -founder of Sales Feed and most importantly, and I'm stealing this directly from Ms. LinkedIn because it's the best thing I've seen in a while, chief vice directing president of Managing Things for Will Aitken.
Congratulations on the title, Will. That's amazing.
Will Aitken (00:31.714)
Thank you, it's a recent promotion. Before I was only the vice president, director, assistant manager of managing things at Willakint .com. So it's been a really big upcoming for me in my career.
Adam Sockel (00:41.743)
Yeah, listen, I can only hope that you will do right by the other Will Aikens at willaiken .com and your leadership will only keep everyone soaring, everyone, you know, rising tides in all those situations.
Will Aitken (00:52.897)
That's right. To be fair, I mean, this immediately I'm taking some time here. I just hired an employee full time to work with me and giving them an email address lukeatwillaiken .com felt like one of the most egotistical things I've ever done when I, I still need to think of a better name. But there we are.
Adam Sockel (01:09.679)
I think it's tough now. I mean, there's obvious there's so many organizations out in the world. Actually, just a person I went to high school with. We've been recording for one minute. I'm already on tangents, but here we go. Somebody I went to high school with is launching his own company. And it's the way that he had to name it because it's like a plan certain words that already exist, like just the way they have to spell things now to get a, you know, a title that actually is not out in the world. So I think just using your name is okay even.
Will Aitken (01:18.336)
Ha ha ha!
Will Aitken (01:34.592)
Yep.
Adam Sockel (01:39.247)
though maybe it might feel egotistical, people will be able to find you.
Will Aitken (01:41.407)
And it feels good to give the middle finger to all the other Will Aitkins out there who didn't get that domain name, you know? I sometimes find them on LinkedIn, I send them an email like, ha! You know? Loser! And I got willaitkin .ca as well, so all the Canadian ones, I make sure to really make it sting, you know?
Adam Sockel (01:47.087)
Yeah.
Adam Sockel (01:57.007)
Yeah, yeah, listen, you're doing the right thing and I'm really, really proud of you. For people who this may be the first episode you are listening into our bold calling podcast. The theme of this season is no sleep till closed one. And so the way that we're doing this is we're breaking up each episode into three segments. The first one we're going to talk about Will and his background a bit and all the things that he's doing. Then the second segment will be kind of getting into the things that are keeping him up at night, stressing him out, how he's working to solve those.
And then we'll have, I've been saying some fun in the third part, but I imagine this whole thing will be a lot of fun for us. So the third one will be some rapid fire, lighthearted questions. So first things first, for people who maybe just know of you as an online presence who does very, very humorous things, but also very, very informative sales things, kind of a balance of the two, kind of walk me through your history. How did you get to become the great overseer of Will8kin .com? I imagine that wasn't just an overnight thing.
Will Aitken (02:52.668)
Yeah, no, it wasn't. It definitely came about over a few years of doing work, creating content, getting to a place where I felt ready to oversee Willaiken .com, which is a very important role. Way back, you know, I got started in sales about eight years ago, suffered my way through it like most salespeople do, didn't really have a clue what I was doing, didn't get any great support from a manager.
Then I got a job where I got really good support from my manager and I started overperforming and that allowed me to spend some free time not worrying about sales and instead making stupid videos. And then the rest is kind of history. People apparently like them and still continue to like them, which is nice. Because I'm waiting for the day that it's just gonna all stop and everyone's gonna be like, he's lost his edge, he's not funny anymore, but we're still going somehow.
Adam Sockel (03:39.567)
Yeah, so I imagine the, you know, we're making jokes, but the personality that you have, I imagine that was very, very beneficial for you as you started out in the sales space. Was this kind of the personality slash persona you always had when you were doing that cold outreach, trying to get a hold of people? Did you always have this sort of lighthearted, playful tone or did it take a little bit for you to find that?
Will Aitken (04:05.017)
It definitely took a lot of me to find that. Like you don't, you don't, I don't think there's the safety always when you're doing code outreach, even when you're like, as an AE, I've never been an SDR, but anytime I've been an AE, I've had to do some prospecting for myself. You kind of get, there's a stigma about like, you have to be buttoned up, you have to be professional, you know, and also being more of yourself can sometimes make the rejection hurt more as well, because you're putting more of yourself into it, so it's easier to take it personally.
But when I realized that one, selling and talking to people as yourself is way less exhausting, because you're not pretending to be something you're not, but also way more fulfilling because just being you, things got a lot easier and a lot better and I enjoyed sales a lot more. So to answer your question, no, I was doing the boring cold scripts thinking it had to be a certain type of way. But then when I realized I could lean into the things that make me me, it became a lot more fun and a lot more successful.
Adam Sockel (05:02.415)
Yeah, I, the, this big takeaway over the past several months of I've been working on this report all about AI and sales development. And then, you know, with like, there's all this interesting conversations is back and forth, everything in the sales space, especially in B2B sales, I feel like it moves so lightning fast from what is the big thing. But in reality, it's really not because it, you know, now the kind of big conversation I'm seeing online is like, well, people really are appreciating when you just be yourself.
And like, you know, the humanity is coming back. It's like, that's back in vogue. Being a human being is back in vogue, which is great. But I do find it interesting where if you are able to, like you said, kind of be yourself and maintain that like, hey, here's who I am. Here's what I'm doing. Like even on a cold call, you know, I've seen so many clips where you've been using ORM and you're just like, listen, I know I caught you out of the blue here. That's like, I do feel using that humanity is so important and people still respect that.
Will Aitken (06:00.725)
Yeah, I think it's a lot easier for me to say now because I run my own company and there's less risk of this, right? But there's this realization that I even kind of spoke through it live as I was thinking about it on one of the live cold callings I was doing. I was like, I may as well lean into 100 % will here, drop the button down, the script that I was using and just say what I would say if I had total freedom, which I do. And if they don't like it,
then in a way they wouldn't have liked having a meeting with me anyway. You know what I mean? Like they probably wouldn't have been the type of person who would have worked with me in any kind of capacity anyway. Now that's easy for me to say when I'm running my own company, but the same can go for certain elements of sales. Like if I'm an account executive and I'm trying to generate my own pipeline and I'm having to, can't act myself, then what's the rest of that sales cycle gonna look like thereafter? We're gonna have awkward discovery meetings because they don't find me funny.
Adam Sockel (06:37.229)
Mm -hmm.
Will Aitken (07:01.171)
or it's just gonna be, I'm gonna do something that's gonna rub them the wrong way. So being your style in a way almost disqualifies people who probably wouldn't have jived with you anyway. But it's much easier for me to say running my own company because I have full control over that. When you're in a sales role, you have the pressure of not being able to always say, hey, you get judged by a manager and stuff. Here, there's only my followers can judge me. And I'm sure they've already done that a few times.
Adam Sockel (07:24.75)
Mm -hmm.
Adam Sockel (07:30.19)
But to your point, I've been thinking a lot about this. I was having a conversation yesterday, which yesterday means nothing to people listening to this because by that time it will be several weeks ago. But exactly, there you go, perfect. On May 8th, I was having a conversation with another guest of the show and I was talking about the fact that at Orem, we're really proud of the platform that we have and the tooling that we have available to people. But I also, I believe in honesty and to be honest, our competitors have great tools too.
Will Aitken (07:40.563)
May 8th.
Adam Sockel (08:00.078)
That's sort of why ART, that's one of the reasons why ART tool keeps improving is because there's pressure to keep innovating. But at the end of the day, we have so many people, whether they are customers or sales partners or influencers who come to us and like basically say like, hey, I really like, like, I just enjoy working with you all as people. And I think that is something to your point, whether you're a brand new SDR starting out or you're a seasoned, you know, AE working with enterprise organizations like.
If the margins between what separates you and your competitors from a technology standpoint are really, really narrow, the people that they prefer to work with are the people that they're going to work with. And so I agree with you, like it's be yourself.
Will Aitken (08:42.064)
Yeah. I love that take so, so much. So, so much. Cause yeah, a lot of the time in SaaS especially and I know of a space as well. Obviously there's a huge gap and your thing sucks and the person is great. Probably won't make all the difference even if you're amazing. You're going to get a lot of thought. You've been amazing, great rep. I hate those ones with you. Thank you. You're a really good sales rep. I'm like, if only compliments paid the bills. But if it's like a neck and neck race and you've just made that person happier, you've made them trust you, they enjoy speaking with you more, it can be the...
Adam Sockel (08:57.261)
Mm -hmm.
Will Aitken (09:11.919)
deciding factor. And I've had that several times, especially when I've been selling from a smaller company, I've been up against a big one, because those big ones don't have the flexibility to really lean in, do fun stuff. I always remember this deal way back in December, 2021. Yeah, December 2020, should I say. And I was working this deal with an accounting firm, 30 users for a software platform. And we were up against someone and they came on the call and they said, look, well,
we don't really see any differences between your platform. You sent us a video of you and the other account executives and SDRs on the team. And I'll send it to you if you want to insert it into this. Singing a cover version of, deck the halls with lots of holly, something, something, I can't remember the cut. Deck the halls, deck the halls, yeah, okay, I nailed it, yes. Anyway, we changed the words of that to make it work for our value prop. And we sent it to all of the deals we had in Pipe. And they said, we watched that as a team.
Adam Sockel (09:57.966)
Literally deck the hall, literally deck the hall is the name of this.
Will Aitken (10:10.286)
and we just said, that's good people. And that's the type of people we wanna work with. That video of us wearing stupid Santa hats and badly, horribly singing it was what made us win the deal because everything else was the same. They just said, no, those are good people. And hearing that, I was like, wow, that's a good feeling.
Adam Sockel (10:27.726)
Yeah, first off, as a person who I, an organization I used to work for, my brother was also there, it's called Overdrive, I've talked about it a few times now, it's an ebook and audiobook app, people can borrow books from the library on their app called Libby. He and I, we used, they had an event called DigiPalooza, which was their, every other year, their kind of biannual user conference. And it was called DigiPalooza, and it was shortened to DigiP, and we took Under the Sea from Little Mermaid and changed it to at DigiP.
and made our entire organization from like CEO all the way down to like brand new people. We basically made everyone sing along and then our videographer there cut it into just an absolutely ridiculous video. And we sent it out and people were like, we found budget to come to this because of your absurd song. Like, I mean.
Will Aitken (10:59.66)
Good stuff.
Will Aitken (11:14.603)
We found budget. No, that's so good. And I mean, even like, I remember way back when I was a customer of Oram and I didn't have a decision -making role, but I was using it on a daily basis. There's the little things like that, especially when you bring in like senior leadership, not just the rep. Like again, another thing that won me tons of deals when I was working for a small company and going up against these big dogs is I could get my CEO to record a quick video, just sent to the customer saying, hey, not asking for anything from you, just know that you work with Will.
Adam Sockel (11:32.393)
Mm -hmm.
Will Aitken (11:43.274)
want to let you know that I'm here if you need any help. And like the bigger companies could not send a Slack message to their CEO to say, hey, can you make a quick video to help us deal across the line for the end of the month? And Orem way back when your CEO, Jason, he jumped in and gave us cold calling training as part of our onboarding as a CEO doing that, because he said, there's one thing to give people the tools, but if they're not successful on the phones that we know that they're not going to get as much out of this as we know that it would.
Adam Sockel (11:56.813)
Mm -hmm.
Will Aitken (12:10.857)
And doing things like that, I still remember that today, and that was almost three years ago now. So those little things that you can do, they really make all the difference.
Adam Sockel (12:20.)
Listen, we talked about standing out and at Aurum here just recently, we have these yellow analog phones that everyone seems to love. They say Aurum, yeah, Will's gonna go, yeah. That's okay. That's okay. So for people who are listening who maybe haven't seen them on social media, they're literally picture the cordless, or like corded phones that, I'm aging myself now, but I had when I was growing up, that you would sit there and twirl the cord on your finger.
Will Aitken (12:30.952)
no, it's on the staircase. I'm gonna... Ugh, darn it.
Adam Sockel (12:49.102)
We just got a bunch of them that said Orem and they connect to your computer and people can use them to cold call. And everyone loves them. And we have been giving them away. And our VP of sales, Colin did a video this week at Forrester, the B2B Summit where he had one of those, but he also had an actual banana. And he was just like talking into the banana. He was like, can you hear me? Can you hear me? And like, just like these silly little things that differentiate you from your competitors. And like, it's like, not only.
Do I like that platform? But they have a personality and they like to have fun. It is interesting, the things that move deals along. This isn't a question. This was me just wanting to talk about our banana phone one more time. Yeah.
Will Aitken (13:26.055)
I love the yellow phone. It's great video for video props as well, because it's so clearly a phone and stands out.
Adam Sockel (13:31.145)
Yeah, yeah, 100%. So, you know, transitioning into, like you said, you, you know, now you own your own business and you run your own business. And I was, I'm really excited to kind of get to the second segment of the podcast with you, because I think your take is going to be a lot different than the VPs and directors and even founders that I've talked to so far is, you know, what is the thing that, that keeps you up at night? Like what is stressing you out at night from a work standpoint that you're constantly trying to solve?
Will Aitken (14:00.197)
I have a common pattern of over committing myself, saying yes to a lot of stuff, saying I can get it done sooner than I think I will be able to do it. You know that saying, you always overestimate what you can do in a day? Every day feels like that for me. And that means that I'm kind of always playing catch up. And it's part of the reason why I hide someone. And I'm trying to find ways and systems to get me caught up on that. But.
Adam Sockel (14:07.341)
Mm -hmm.
Adam Sockel (14:14.254)
Mm -hmm. Yeah.
Will Aitken (14:27.108)
It's really hard to sit there at 10 o 'clock at night, even if I'm tired and think I could be doing this right now. And when it when it's just you working for yourself, it really is. It just comes down to you. So put stretching myself too thin, saying yes to too much stuff or even trying to over deliver. And in the process, I almost sometimes over promise and deliver by trying to over deliver. I want to be able to say I'm going to do all this for you because I really want to make this work. And then I fall behind.
Adam Sockel (14:32.588)
Mm -hmm.
Will Aitken (14:56.482)
And that's an ongoing challenge that I've had to deal with in several different elements, whether it's balancing travel, because I always assume that I'm gonna have downtime when I'm at a conference to get something done, but I never do, because there's always something pulling me away. Or even it's just me sat at my desk and I just underestimate how long it might take to edit video or build a list of people to Cold Cool, which I'm about to do right after this. And I've literally spent the last 20 minutes like...
Speed importing contacts into my CRM so I can make sure I actually have people all listed up to dial But that that's a lot of a lot of my life plan catch up And I think it's always been built like that's ADHD to a certain extent, but it's also part of like
Adam Sockel (15:27.436)
Mm -hmm.
Adam Sockel (15:36.237)
Mm -hmm.
Will Aitken (15:40.001)
But part of, I don't know, I do want to do well. I think I just sometimes think too much can mean not doing as well. And so I have to figure out a balance a bit more.
Adam Sockel (15:51.437)
Yeah, I very much know exactly what you mean for me. Like tactical standpoint next week, our go -to -market leadership, we are all meeting together in Philadelphia to talk about H2. And my best laid plans right now is I am planning to edit these podcasts in my downtime, of which I know I will actually have none. So I very much feel you there. And it's a constant struggle for me too. I am in fact, my boss, Ting Ting, our VP of marketing here.
implores me to try and say no more often. It's a struggle for me too. So you mentioned hiring someone. Are there ways that you personally are successfully overcoming this or is it something that you're still very much a work in progress?
Will Aitken (16:26.399)
Hmm.
Will Aitken (16:39.299)
Yeah, I think knowing where my time is actually valuably spent, so the reason I've hired someone is because I realized almost half my time right now was spent editing videos and I love editing videos. I love that creative stuff. It feels satisfying for me to take some from not finished to finished. It's a satisfying process for me. But realistically, at my pay grade, if I was a video editor, I'd be the best paid video editor probably on the planet, right?
Adam Sockel (16:52.524)
Mm -hmm.
Adam Sockel (17:08.684)
Yeah.
Will Aitken (17:09.118)
So it doesn't make sense for me to do that. And that's why I then looked into investing and bringing someone in for support on that. And before I had them, I started turning to freelancers, et cetera. So I think it's a case of figuring out what a low value task is and trying to find ways to delegate that or make it easier with tech or tools. There are so many tools out there that can make you more efficient. For example, to your point, I edit the 30 minutes to presence club podcast every week. There's two episodes a week.
Adam Sockel (17:23.212)
Mm -hmm.
Will Aitken (17:37.212)
I found some really great AI tools that helped me cut up the clips and have active speakers and that saved me three hours on the edit on that because that's one of the things I don't want to let go of because I know it means so much to them to have a really high quality podcast production because they're one of the bigger ones in sales and I don't feel safe yet. Maybe one day when I get my new hire to that point, I don't feel safe yet letting go of that one. So knowing where to let go and then when I don't let go, finding ways to make sure that's efficient.
Adam Sockel (17:52.876)
Mm -hmm.
Adam Sockel (18:07.245)
Mm -hmm.
Will Aitken (18:07.323)
time blocking is something I've always had success with, but it drops off very quickly. Like I can get a week of, and I'm like, my God, I was so productive this week because I time blocked, but then the following week I'm not religious enough of actually continuing that routine, that pattern, that habit of having really good time blocks and actually making sure those time blocks are the right size. As I said, I always underestimate how long something's gonna take. It's really hard to walk away from something if it's not finished for me.
Adam Sockel (18:24.78)
Mm -hmm.
Adam Sockel (18:32.461)
Yeah, for me, it's, I, there's this phrase in sports that the best ability is availability. And in sports, it's basically like, it doesn't matter how talented of an athlete you are. If you're hurt, you're not going to help the team. And I have always used it in my career being like, I've overextended myself because I started, I've been doing content marketing for 15 years. And when you first start out in content marketing, a lot of times what that means is you're doing social media. And if it's a global.
company, you feel like you always had to be available. And I have exponentially grown in my career in part because I'm available all the time. And it's very hard now as a person who, in theory, I'm supposed to be more strategic and less like in the weeds on stuff. But I've been doing things in the weeds literally for 15 years. And so I'm like, it's so hard to pass those things off and trust.
Will Aitken (19:27.448)
Yeah, and to your point, both sales and I think marketing as well in the enamel of this, it's one of those jobs where the job is never really done if you want to excel it. There's always something more you can do. If it's in sales, it's activity outbound. If it's in marketing, it's getting on social media, observing things, looking for inspiration or creating the next big idea that you have or coming up with ideas. It's never really done. So you need to decide the limits of where that is. Otherwise, you would just work all the time. And then as you said,
Adam Sockel (19:40.299)
Mm -hmm.
Will Aitken (19:56.984)
You don't do good work when you're totally burned. And recognizing that is part of the process of realizing, okay, I need to protect my time. I need to say yes to the stuff that's actually going to do the most for us.
Adam Sockel (20:10.156)
So to that point, this is, I told you before we started recording, I was thinking about this conversation last night, which is indicative of the conversation we were just having about, yeah, I was like, you know who I really adore? That Will Aiken of willaken .com. He's a really great guy. But no, I wanted to ask you about kind of like refilling your cup from a creativity standpoint, because you're right again, working in content, a perfect example of this is as we speak on May 9th, we are getting ready to roll out this.
Will Aitken (20:17.815)
Aww.
Adam Sockel (20:40.396)
AI report, which is our huge quarter, the Q2 pillar piece that will drive organic traffic. And hopefully a lot of DemandGen is one of our DemandGen people is hanging out as the producer of this podcast episode now. but I'm thinking through this, we're just getting it into design to then put out into the world. And I'm already starting to think about the survey we're going to run that will turn into our Q3 piece. And it's like, it's always that next thing.
And then in the meantime, I'm also trying to think of like, okay, well, what's the daily shorts we can put out and TikToks and what can I put on LinkedIn this afternoon so that we keep driving traffic? And it, I have never found a way to fix my burnout other than like I work until I get burnt out and then I go to Mexico or Scotland for a week or whatever it is. Like for you, how, especially now with working for yourself and also like representing so many different brands and.
needing to create content for all these different places. How do you refill your cup from a creativity standpoint? Like what helps you do that?
Will Aitken (21:52.5)
done it.
Adam Sockel (21:52.639)
no, I think he's froze.
Adam Sockel (21:57.131)
It's like, wow, he's really focused on this question. That's okay.
Will Aitken (21:58.772)
Okay, I got, I cut out there, my bad. I think I'm back now. You're moving again. I heard the last thing I heard was for you and then you sound like you're about to go into a question about how I keep that full.
Adam Sockel (22:05.387)
Yeah, it's a -
Adam Sockel (22:12.3)
Yeah, okay, all right. So for you, how do you refill that cup from a creativity standpoint, especially working with so many brands and needing to come up with content across different organizations and different ICPs? How do you find time to refill your creativity?
Will Aitken (22:38.386)
Hmm.
Will Aitken (22:43.73)
People, I think talking with people, actually, and this is why, when I first started working for Vidyard's media brand, Salesfeeder, which I'm now co -founder of, co -owner of, technically didn't found it, it's a long story, but there was this team of people who I could always rely on to bounce ideas off or get excited or share energy with. And now I'm working a lot on my own.
It's a case of finding people who I can work with around me. So whether that be peers, you know, I have a lot of online fake beef with Jenelle and Canoof, but we probably talk twice a week and those conversations really fill my cup a lot and make me feel less alone in it. And sometimes you can get this gut feel and this instinct for what's going to work and what's going to be good, but it's hard to trust that always. And because I'm just pursuing an idea that's just going to turn out rubbish.
So sometimes just talking to someone, having someone to bounce ideas off is really helpful for me. The second thing is consuming. I don't get ideas editing videos. I get ideas consuming new content, whether that's something on LinkedIn, something on TikTok, something on YouTube. And it's not always, you know, all the content I make is BTP sales related, but the content that inspires me that I consume rarely is. The stuff that really inspires me is the stuff that I enjoy and seek out.
on my own and just consuming things gives me new ideas, new perspectives. Even if that perspective isn't one that I share, it can give me a reason to think about it. So from reading books to watching YouTube videos in my downtime to scrolling the feed and this is where I tried to do that as intentionally as possible to make sure it's not a total time sink.
that that's where I get a lot of my creativity from. And if I don't do that in a while, that's where I start to feel a little bit burned out in terms of like, I've got no ideas left. So, being intentional about how I consume content and talking to people is the sure answer.
Adam Sockel (24:43.988)
Do you give yourself like a cutoff of any sort? I'm asking because I think I might have told someone else is like, my fiance is also in B2B startup marketing. She's, she does demand Jen for a cybersecurity company. And like, we almost jokingly have to, we're like, it gets to a certain point after dinner where we're like, okay, no more open rate conversations, no more.
Will Aitken (25:02.477)
Mm -hmm.
Adam Sockel (25:13.292)
no more headline discussions, like we have to watch the Great British Baking Show in Zona, whatever it is. Do you give yourself a cutoff? Or especially now, working for yourself and doing your own thing, is it kind of 24 -7, always on? This is more like therapeutic for me than for the podcast I'm finding at this moment.
Will Aitken (25:36.172)
I'd love to tell you that I stop thinking about it sometimes, but I'm always kind of thinking about it somewhere in my mind. I've got to the point where my wife doesn't work in demand, Jen, but she's so sick and tired of hearing about me and my content that we don't talk about. And to be honest, when she talks about accounting, it boils the crap out of me as well. So we find other things to talk about and that's a good release. I also have two kids and frankly, four -year -olds don't really care about the best cold -cool opener. So yeah, I know, right? Little slacker. He's not going to Presidents Club. No way. But you know,
Adam Sockel (25:59.403)
What?
Will Aitken (26:06.123)
playing with him and just doing stuff like that, knowing when I should be thinking about it, when I shouldn't, and drawing those lines is also so much I can do. That said, there are times on the weekend where I'm like, my gosh, this is a great idea, or I'm thinking about something or checking the emails. And it's ongoing, I don't think you can just suddenly say one day I'm gonna set boundaries and those boundaries magically appear.
Adam Sockel (26:24.042)
Mm -hmm.
Will Aitken (26:32.17)
It's like you learn over time, okay, I need these boundaries. How am I going to work on them one bit at a time? Whether it be at five o 'clock, I'm done. And that's really hard, especially as a founder, you know? It's really hard when there's still work left to be done at five o 'clock, I'm done. And on those days I sometimes go, okay, you know what? I'm going to finish at five, hang out with my kids, have dinner, sit down with my wife, watch some TV. She goes to bed at like 9 .30 and I'm going to go an hour and a half to catch up after that.
Adam Sockel (26:42.795)
Mm -hmm.
Will Aitken (27:00.233)
And that doesn't sound that healthy, but it is healthier than me spending that entire five hours kind of working, kind of doing something and not giving those people who I care about 100 % of myself.
Adam Sockel (27:13.099)
Yeah, it's, I think we just described as healthy as you can, especially in like tech and like the, I feel like that is, if I was to describe my days to my parents and I do sometimes they'd be like, my God, you're working till 10 o 'clock. I'm like, well, there's a run in there and there's a dinner in there, but yes, yes, yes I am. But I'm also just now thinking about one of my nieces or nephews calling and asking if I have 25 seconds to talk about Bluey or something. And yes, I do 100%.
Will Aitken (27:37.544)
Hello, it's Archie here. Dad, do you have 25 seconds to help me build Legos? Like, yeah. No. Send me an email about this, buddy. Bye. Beep.
Adam Sockel (27:45.9)
Yes, I do. Yeah, I'll follow up. I promise I'll open it. All right, let's transition to the third segment of the show here where we're just a little speed around of some fun questions. So the first one is, what was the first job you ever had? This can be the first job when you were a kid. It can be out of college, whatever you want to talk about, your first job.
Will Aitken (28:07.399)
I was a bar nightclub promoter in Oxford, you know, the kingdom. One of the worst bars there. That's why they needed promoters. So every set Friday and Saturday night, it was during my first year of university when I was 18 years old, I'd just go stand out in this room of Oxford and hand out flyers. We'll try and grab groups and drive them into the bar.
Adam Sockel (28:28.171)
Was it like, I'm just picturing a Will Aitken with like five buttons unbuttoned and like sunglasses.
Will Aitken (28:34.15)
Yeah, the UK isn't quite that tropical. The bar was a Hawaiian -themed bar, but my ties and stuff. But I had a dress code, I had to wear a blazer. And this bar had sticky floors, so I don't know why they had me dress up so much, but yeah. It was quite fun. They actually never, they didn't actually pay me that much. They were so slow to get my stuff on payroll that by the time they put me on payroll, it was the week I quit. And they ended up paying me like a fifth of what I was due for the hours I'd worked.
And I never chased them on it.
Adam Sockel (29:07.723)
Yeah, I think that might be lost money. The next question is, what was your worst job? But I'm worried it might be the same job.
Will Aitken (29:10.597)
Yeah.
No, I wouldn't say that. I would actually say the worst job I ever had. it's a hard one actually. Because when you go to Australia, which is where I met my Canadian wife and which brought me to North America, you can do work on a farm to earn a second year of a visa there. And so you get one year as a Canadian or a Brit and I think the US gets one year as well. You just apply for it, they give it to you most of the time.
but the Canadians and the British can work on a farm somewhere in Australia because they have a worker shortage. And you can work on like an orange farm, an apple farm, pineapple farm, whatever it may be. And I worked on a potato farm driving a tractor, which was pretty fun. But then I lost that job because the season ended and we went and worked on an orange farm, which wasn't paid by the hour, it was paid by the bin of how much fruit you pick that day. And you would have to be...
Adam Sockel (30:06.666)
Mm.
Will Aitken (30:13.155)
very, very quick and very, very fit to fill up a bin at a rate that would give you any kind of reasonable hourly wage. And so I went to work on an orange farm and these orange trees were just packed full of spiders. And I don't mind spiders that much, but big spiders and poisonous spiders, I'm obviously gonna have a few objections about that one. And you had to get right inside the tree to get the ones in the middle. If you didn't pick the tree right, they'll take the docupe. And that was rough.
I only did that for five days, but it was sweaty work. My wife and I were working together. She was quite slow and she hates spiders, so she wasn't really getting in the tree. So I was doing a lot of the grunt work and she was kind of doing the stuff on the outside. No shade to her. I get it. It was a bad job and that's why we left it after five days and probably made about $200 in that time between us.
Adam Sockel (31:00.491)
Man, I like just last night saw a TikTok of a person who she's a like fifth generation tree planter in I think British Columbia. It's talking about like she makes it's like 19 cents per tree she plants. It's like that. That's rough. Yeah. Do you have a favorite app for productivity like that you use during your day that's really helped maximize what you can do?
Will Aitken (31:16.13)
Backbreaking work.
Will Aitken (31:26.338)
Do you mind if I have a look at my phone real quick? Because I need to jog my memory.
Adam Sockel (31:28.074)
I don't mind at all.
I also appreciate you not saying Oram because I would have been hokey and, you know.
Will Aitken (31:35.008)
All right, everyone just stop listening right there with the full plug. I don't use ORM every day. I use it once a week for my live calling. Let me just have a quick look. One I use every day, I would have to say...
Adam Sockel (31:38.666)
Yeah.
Will Aitken (31:51.519)
I make a lot of video content.
but I also do a lot of design as well. So it's somewhere between my editor, which I use, which I use DaVinci Resolve or Canva because I'm not design savvy and they do a lot of the work for me and Photoshop scares the crap out of me. I have to watch a YouTube tutorial just to do one thing that I could have done in Canva in two seconds, right? So I'd probably say Canva to be honest.
Adam Sockel (32:01.514)
Mm -hmm.
Adam Sockel (32:07.114)
Mm -hmm.
Adam Sockel (32:14.987)
Yeah, Canva I feel like has been this tool that I've been using for so long that I started using it because same thing, I have no design skills and if our designers at previous companies weren't available to help me with something, I was like, well my God, Photoshop scares me, so I'm gonna use Canva. And now it's like all this time later that people are still like, yeah, no, it's actually wonderful. I fully, fully agree there. How about for fun? Do you have an app that you...
love for fun is it you know it could be tiktok or instagram something like that or it could be a games or something you like to kind of zone out and use.
Will Aitken (32:47.901)
Let me have another look. Fun apps that I have on here. Let me just have a look.
This is so lame looking at this and not seeing anything that I really find that fun. I...
Will Aitken (33:05.02)
Popeyes app count? No. I spend a lot of time on more than I should probably. And I've gone through phases of deleting it and reinstalling it on Reddit. Mainly just because I find that there's such a wealth of information that I can go down some serious rabbit holes and I love reading about new stuff and learning about it. Like when I was at university, I would do this weird thing. I would see something and I'd want to know what it was. Like for example, I went to university in Brighton and out in the distance in the sea, there was like this lighthouse.
Adam Sockel (33:09.194)
I mean, it's.
Will Aitken (33:34.94)
but it was like a platform and I looked at it and I was like, I need to know what that is. So then I like went on, like did all this research and land on the Wikipedia page of it and just found myself in this down this rabbit hole and I find myself doing that a lot. And Reddit is one of the places where I do that. There are sides of the app that I don't like, which is like any social media can be bad, but I find Reddit is especially can be very negative and that can have an impact on my headspace. So I need to recognise when that is and that's why I've sometimes deleted, sometimes bring it back, sometimes delete it.
Adam Sockel (33:57.29)
Hmm.
Will Aitken (34:04.636)
So that's probably where I spend a lot of time.
Adam Sockel (34:08.138)
Yeah. What is, describe like an ideal workday for you.
Will Aitken (34:12.54)
Hmm, that's a good question.
Will Aitken (34:18.012)
Probably maximum of three external facing calls. Any more than that and I find myself not productive. Something where I get so new produced, reach new people, do some prospecting, knock off at least two things from my weekly to -do list, and then finish on time and accomplish what I set out to do that day.
And that really often comes down to not how productive I am, but how much I try to stretch myself. Like if I look at my seven days a week planner, I can look at the days where I didn't hit my goals. I'm like, no duh. Like how many things do you think you're gonna get done in that day, right? It's really easy to reflect on that. So it really comes down to setting the right goals for me to feel fulfilled and knowing that I've done well that day. Because otherwise I could write a hundred things in there, I'm never gonna get them done, right? So it's setting the right goals for myself.
Adam Sockel (35:13.995)
I'm very good at writing a to -do list the night before every day and be like, I'm going to get all this done for sure and then hating myself and I get the, no I'm not. I'm so, absolutely. All right, last question for you. What is a cold call opener or pitch that would get you to at least stay on the phone with the person who had called you?
Will Aitken (35:18.908)
No you ain't.
Will Aitken (35:31.644)
There's very few calls that I won't stay on the phone for if I'm honest, and I might be an exception case to this. I find a lot of salespeople and sales leaders kind of fall into this camp of like, I'll always hear someone out for two reasons. Number one, they're gonna do something bad. Three reasons. Number one, I have empathy for what they're doing, right? I get it. And I respect the grind and anyone who's cold calling these days immediately is getting way more of my attention than someone who's emailing or my LinkedIn inbox is just, it's horrible. Like there's nuances to that obviously.
If someone cold calls me, I'm always gonna hear them out. So with the exception, so I would hear out any cold call, I would stay on the line for any cold call except for the ones that are so blatantly trying to get me to sign up for a credit card. Those ones drive me nuts because I get five of them a week and I don't, I'm like, I've got enough credit cards, not that I have lots, I just know, I'm very intentional about my credit cards, I love my points.
You know, I love getting my air miles. I love getting my aeroplan points for Air Canada. Love getting my cash back. I know what credit cards I have. I'm not gonna sign up for a new one no matter what anyone does because I'm always planning that with my wife. We'll be like, okay, now you've got the points, the bonus points for this one. Let's do Will next and now get the bonus points for that. And then we'll add them. Like I just know I've got that down. There's very little someone could say to me to make me wanna get a new credit card because I've already thought about it so much. So when someone calls me and says,
Hello there, it's so and so from Scotiabank. Just a heads up, this call is being recorded. How are you today? I'm like, I know what this is and I've got so many of these and I'm like, I always try and be kind and I'm just like, I'll be very honest, this just isn't interesting for me and I would appreciate it. I don't really look into credit cards, so if you could make a note, I'm just not gonna be good for you. And then normally they're like, no worries, have a good one. Sometimes they'll fight me a little on that.
And that's probably the only time I've ever been mean to a salesperson and really hate myself for it because I hate the fact that people chew out salespeople because I was having a horrible day and this person was like, well, if you did, and then they were trying to tell me, and I was like, mate, enough. I had to get stern. I don't like that. I don't like doing that. And I still think about it today because I feel so bad because I'm meant to have empathy with these people, but sometimes everyone has a bad day on that day. So answer your question, cold, cool, any cold, cool. You can say whatever you want.
Adam Sockel (37:39.721)
Mm -hmm.
Will Aitken (37:53.852)
as long as you're not blatantly calling on behalf or in association with Scotiabank to sell me a credit card.
Adam Sockel (37:59.242)
Beautiful, beautiful. Where can people find more information about you and get a hold of you? And we've been making jokes about willyacon .com, obviously, but where else can they track you down if they want to see more of the stuff you're doing?
Will Aitken (38:06.748)
Yeah.
Will Aitken (38:11.697)
I have a lot of fun on LinkedIn obviously, that's a great place to find me and also on my YouTube which is, you know, our YouTube should I say for sales feed. I have a lot of fun making those videos. They don't make me any money so if I'm doing them then it's normally because I actually want to and that content often turns out to be the best. So sales feed on YouTube, great place to go. Subscribe, check out some of the old videos, there's great stuff on there and look out for the new ones.
Adam Sockel (38:35.209)
Beautiful, I will make sure all that is in the show notes as well. Will, I really appreciate you joining us today before you get on your marathon cold call a -thon. So thank you for joining me today, this was a blast.
Will Aitken (38:46.928)
It was a blast. Thank you so much for inviting me on, Adam.
In the world of SaaS, especially for startups and founders, the idea of turning down an opportunity is crippling. We work tirelessly to create leads, foster relationships, and earn decision-makers' respect. So when partnerships and deals present themselves, it’s natural to want to say yes.
For Will Aitken, this problem of “more” is genuine. As a successful seller, Will found he had a talent for creating engaging video content. Both informative and entertaining, his videos built him a following across multiple platforms, leading him to start working for himself at the beginning of 2024.
Will understands that we buy from people we trust. By being extremely online, he has created a large audience of sales professionals who trust his advice. Working for himself, he’s also learned that there is a limit to what he can offer and agree to.
“I work hard to ensure I don’t overpromise and underdeliver. That means saying no more often than I’d like.”
A departure from previous episodes centered around tactical and practical sales advice, this conversation with Will is about structuring our time and growing comfortable with setting boundaries.
Equal parts therapy and introspection, this is a fantastic conversation with one of the sales industry’s leading minds.