Ali Schwanke on creative diligence and AI’s constant iteration

Ali Schwanker, Founder of Simple Strat and host of HubSpot Hacks, joins Bold Calling to discuss navigating AI to ensure scalability and her heightened awareness about shifting marketing strategies as a founder.

Adam Sockel (00:01.167)
You're listening to Bolt 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 a 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 Ali Schwanky, founder and CEO of SimpleStrat. Ali, thank you so much for taking some time to join me today.

Ali (00:22.271)
Thanks for the invite. Excited to be here.

Adam Sockel (00:24.271)
Yeah, so as people may know who have listened into previous episodes, which is a weird thing to say because we are recording this before it's actually gone live. So I feel like I'm in a time machine, but we will be breaking these episodes up into three kind of segments. The first one we're going to talk about Allie and her business and her background. And then we're going to get into the things that are keeping her up at night and then we'll have some fun. So so first things first, can you kind of introduce yourself and your background and.

Simple strap, but first let's build up to how you got to where you are today and we'll have some fun breaking down your history.

Ali (00:56.671)
Sure, well, the first thing that I'll tell folks is if you happen to search on YouTube for any sort of HubSpot support, HubSpot help, you might recognize myself or my team from a series called HubSpot Hacks. We're most well known for our tutorial series over there. We get about 150 videos on YouTube. So that brings us to the company we have today, which is a HubSpot consultancy. We help people build, grow, implement, fix all the things you could do on HubSpot. We're kind of like a general contractor of all HubSpot related problems.

And then, you know, my background is I've done a lot of video, photo, podcasting, content creation, just I love educating and helping people, which landed me in marketing. And there's way too many roles probably to mention before I started this company, but ultimately like love finding out what makes customers tick and finding out how to create content and paths in order to reach those people.

Adam Sockel (01:45.294)
I will say, you can always tell and people who listen or who watch some segments of this on social media will see this. The first thing I told Allie when the first time we ever had a conversation, I can tell you're a person who likes to create content because your background is very soothing. That is a thing that people don't realize how important it is. I need to work on this one a little bit. But for people who are listening into the podcast, Allie has these like, are they like foam Legos kind of that are sort of like make walls behind you. That'd be a good way to describe them.

Ali (01:58.462)

Ali (02:10.815)
I wish they were foam, that would be more fun, but these are hard plastic, but they are, they're giant, they are, they're giant Lego pieces. And we built a whole wall behind me. We have my business partner has them behind him. They used to be in our office as cubicle dividers, but now they just, they fit well for the series that we're working on, which is called Marketing Deconstructeds or Deconstructing Things. So it just, it makes a lot of sense.

Adam Sockel (02:31.822)
That's honestly kudos to you guys. That's really well done. You mentioned, obviously, like you said, people who are familiar with you are very likely are familiar with through all of the content you have created through the sphere of HubSpot. And I'm curious as a generalist by nature, I have always, lots of marketers, people like to say, we like to wear many hats. I just think generalist is an easier way of saying, we do a bunch of different things.

I'm curious how you got into the realm of sort of niching down because it really does help people find you more consistently. It is something that they always say from a content creation standpoint, if you want to grow your following on like TikTok or something like you do want to have a niche, but for you, how did you discover that this was the one where you would find the most success? Is there something you had a lot of joy doing or sort of just walk me through that process?

Ali (03:24.159)
I think it comes down to two things. One is I find joy finding gaps and digging into those gaps. And as we were thinking as a company, we wanted to help people get better marketing and sales results. And so that's kind of where it started and not unlike probably your audience wanting to get better sales results as well. And how you solve that goes about like there was enough shows about kind of like sales strategy. There was enough shows about marketing strategy. There was enough business shows. And so we just dug into like, who's really helping people with kind of the tactical piece.

And both myself and my business partner are very, very tactical in nature in terms of like, okay, that's great philosophy, but like, what do I do today? Right? How do I fix this today? So we found a lot of people talking about HubSpot, but they would like give you their life story and they would talk about how they got into the business. And I was like, I got to build this freaking workflow. Like tell me how to do it. And I don't, I have to use 75 of their systems today. So I think Adam, with your note about being a generalist, we realized there's a lot of marketers out there, a lot of sales teams, a lot of founders.

that need to use HubSpot and HubSpot, I love them, but they continue to say it's easy to use. That used to be true years ago and now it's hard to even figure out how to buy it because there's so many features and so many things. So our goal was taking like niching down into HubSpot specifically, because we knew that we could just create this content quick. We knew we were good at it. And as the more we did that, kind of like you and I were talking about you playing baseball, the more times you're up at bat, the more types of pitches that you see, the more you know what to swing at, what to not swing at.

We just found those patterns in our consulting and so it just really kind of like blew up our content strategy because we knew what we should talk about and what we shouldn't and how people would respond.

Adam Sockel (04:59.054)
This may sound like a silly question on its surface, but as a person who markets a platform that we innovate and iterate very quickly, but it's still the platform that I live and breathe in every single day here at Orem. But even still for me, as we roll out new features, it can even be hard for me to keep straight all of the different things. And we are a still relatively small, relatively straightforward business model. As someone who I know you work closely with HubSpot, but not technically, you know, or.

Ali (05:18.463)
Mm -hmm.

Adam Sockel (05:28.653)
for HubSpot, how are you all, honestly, how are you all kind of keeping up to speed with all of the things that they're coming out with so that you can ensure that you're offering best practices for those?

Ali (05:29.567)
Mm -hmm.

Ali (05:40.544)
Yeah, I mean, that's a full -time job for sure. We've got six full -time HubSpot specialists on our team. We're continuing to add to our team. We've got six more people that support that through content and development and that kind of thing. But we're a small team. We do a webinar every month that requires us to sit down and look at all the product updates. We have one person on our team who kind of looks through that. But I think for us, we're always looking at it through the lens of like, what is the business use case for this feature? And so hopefully we don't get too feature happy because that I think is where people drown.

and like, you could do all these things. So with our clients, like, and with the webinars, it's, okay, what are you doing today? Where are the inefficiencies and what could you do to make this better? And then looking at the product updates in that lens. So, and then sharing best practices among team members and the community. I think it's probably a community sort of effort.

Adam Sockel (06:09.837)
Mm -hmm.

Adam Sockel (06:27.67)
Having someone who has the expertise that you do in this space, I want to ask at the beginning of this year, there was a lot of nervousness about email that came out with a lot of changes. There was a lot of misinformation and confusion and people were like, can we just not email anymore? Are we not going to be able to use HubSpot or Outreach? What do we do? So for you, now this is kind of like the dust has settled. Has...

Ali (06:39.52)
Mm -hmm.

Ali (06:46.29)

Adam Sockel (06:57.261)
Has business changed for people who are using HubSpot from an email marketing standpoint? Like have you seen market changes or was it a lot of just like there was some misconfusion when that first initial bit came out?

Ali (07:12.768)
Yeah, I think by nature marketers, good, better, and different, we tend to make a big deal out of everything. So I think whether it's a, whether you're trying to combat it from a competitive perspective. So here's, let's say, for instance, let's say HubSpot was going to attack outreach, which they didn't, but let's say they were, and they'd say like, all these cold outreach tools are just not going to work anymore, which is why you should move to HubSpot. They could use that message to their advantage. Outreach is like, no, no, no, listen, nobody really knows what the future holds. Stop freaking out.

You know, there's just a couple of things you need to do. So I think it's kind of a go to advice that my data given me and that is be a skeptic about everything and that should prove to be a valid strategy. So the world's never like it's never chicken little. Like the sky is never falling as fast as everyone says it is. We saw that with AI. We see this with the email changes. We're seeing stuff like this. Like, my God, TikTok's going away. Yes, they're going away. Maybe hedge your strategy, hedge your bets. Like,

Adam Sockel (07:53.965)
Mm -hmm.

Ali (08:10.176)
make sure you have another bag or another basket of eggs, but like, don't just stop and become paralyzed because the news seems to be shifting in a certain direction.

Adam Sockel (08:19.629)
Yeah, it's such an easy social media post to say, insert X thing here is dead. Working at Orem, I literally, yeah, exactly. I am marketing chat GPT, hello. But it is, it's, you know, we here at Orem, people know us for cold calling and cold call outreach. And so as the person who, one of my many hats here is our social media and...

Ali (08:25.376)
Yes. Recipe for engagement right there, Adam. Insert X dead.

Ali (08:34.24)
Ha ha ha!

Adam Sockel (08:46.861)
I could, if I, you know, the old saying, like if I had a dollar, if every time I saw cold calling is dead on LinkedIn, I would retire. And it, to your point, it's like, we, you know, people ask us like, well, you're a cold call tool. So do you exclusively tell people to call? I'm like, well, no, we tell them to use calling and email and social selling and content. And it's an omnichannel, all bound insert word here that you want to use. That's buzzy. Like they all have impactful.

Ali (08:52.128)
Yep. Mm -hmm.

Ali (09:06.4)
Mm -hmm.

Ali (09:12.256)
Mm -hmm.

Adam Sockel (09:16.557)
important aspects of the outreach process because it takes longer and longer now to get people to book a meeting and to pay attention to you. And so you really do need all of those avenues. So I do think, like I said, I wanted to hear it from you, especially just because like even us, I was tasked with writing a blog post about being like, what do you do if you can't email tomorrow morning? And I was like, goodness gracious. Yeah, it was very.

Ali (09:41.376)
Yeah. And all of a sudden you're like, hmm, okay, I need to come up with something in 24 hours here to write about, right?

Adam Sockel (09:47.181)
Yeah, it's all the joys of being a startup, which I know you're also very, very aware of, but it makes for never a slow day. But along with being a founder and someone who is managing a growing company to kind of transition into our second aspect of this conversation, I am curious, what's the thing that keeps you up at night? What is stressing you out job -wise, day in and day out that you're working to constantly solve?

Ali (09:52.576)

Ali (10:12.306)
Yeah, I mean, I think there's two things and one from the founder hat is, are the problems that we're solving scalable? Are the things that we're solving for today going to be replaced by AI? How do we mitigate that? How do we consistently prove our value? I think one thing we've realized is that AI has a very valuable place in the market, but the problem we're now fighting actually is sheer overwhelm of information. So the problem we thought we were solving before was like save time, save money, which is still inherently like the B2B playbook and the value prop.

but people are just, they're overwhelmed. So how, as a company, how do we become more of like a navigator to the market and almost take on like a McKinsey or like a Boston Global sort of like approach to how people grow on MarTech as opposed to here's how to run your campaigns, right? Cause there is no answer. From a marketing standpoint, I'd say what keeps me up at night is the, you know, when you're consistently producing in a channel and that channel changes. So we are heavily into YouTube, as you mentioned.

And we are now, you know, we're in the podcasting space too, but should either of those platforms shift or change on how you capture leads, that's a big piece of our strategy. So I think always looking at, having this like a friend of mine called it a healthy paranoia, having a healthy paranoia for your lead generation and marketing programs to be always vigilant, yet not knee -jerk reaction to change them very fast if there seems to be something awry.

Adam Sockel (11:35.885)
I like to joke my, my fiance is also in marketing in tech. She works in cybersecurity, but she does demand Jen and I do content creation. So we, we joke all the time about how, like at a certain point we get exhausted. Like we have to have a cutoff time every day. We're like, okay, no more saying, shoot, what's the next thing that we feel like the sky is falling because it all, it does feel like everything is always iterating and changing. But, you know, you mentioned AI is one of, one of the interesting both.

Ali (11:49.952)

Mm -hmm.

Adam Sockel (12:04.653)
challenges and opportunities, I think personally, and like I said, our platform, we are all about making human connection. We use AI to eliminate a lot of the manual tasks of cold calling, but inherently, in theory, that really does reduce the amount of people that you would need to do all of the work. And so it's this interesting dichotomy of like, we're making your people more efficient, but there absolutely are going to be some sales leaders who say, efficiency means I can reduce headcount and reduce what we're paying.

Ali (12:12.129)
Mm -hmm.

Ali (12:32.928)
Mm -hmm.

Adam Sockel (12:33.933)
And so, I'm curious for you guys the same thing, how are you approaching AI, especially from a HubSpot space where it is written content, where a lot of things can absolutely be automated, how are you approaching the constant iteration and growth of AI in this space with your clients, and how are you using it from a written content standpoint?

Ali (13:00.705)
Yeah, we probably have the benefit of being a, since we're not HubSpot themselves, we're consultants on top of the platform. And we have a couple of things we're working on as products of our own, but by and large, we don't have our own technology. And so I think we get the benefit of HubSpot kind of making a big fanfare about all these AI tools and how it all is amazing. But yet, then we kind of are in the field seeing how the people are actually using AI. And I'm still finding it a discrepancy between like, my God, I can do all these things. I'm like, what are people actually doing with it? So.

I, you know, and there's a lot to there in terms of written content. So, you know, Google is going to be releasing, you know, chat GPT sort of served AI search results as opposed to like the way we've been doing it before. So I have no doubt that the platform will probably shift in how we create content, but most of my, again, my skepticism over here says there's a lot more talk about AI inside of every one of these tools. It's just kind of like, it's like, if you didn't bake it in, like you're going to be written off.

But no one really knows what it is inside there. They don't know how to use it. And still today, Adam, a lot of people still struggle to know their customers well enough to even put it to use.

Adam Sockel (14:07.116)
That's so that is such a great point. And that is something where one of the one of the first conversations on this platform on this platform on this podcast was with a founder of a company called actively dot AI is names, Angela Gupta and like their tool basically takes all of the information, the data enrichment that a rep would call and have a conversation with you and say, you know, Ali, I know that you're probably not buying right now because 95 % of the market isn't at any given time, but.

Ali (14:35.488)
Mm -hmm.

Adam Sockel (14:36.14)
I would love to learn more about you, yada, yada, yada, how's the conversation and then they can take all that information so that they actually can when those people are ready to buy have a truly informed conversation because to your point, if you don't have the proper data about your prospects, your clients, your customers, it doesn't really matter what your AI, how strong it is because it doesn't have the ability to do anything unless you can provide the proper data. And this is really interesting because you know, you saying like a lot of people still.

don't understand what it can do and so they're maybe not using it. I am in this world where it seems like everyone is using AI because everyone says AI, AI, like you said, it's table stakes to say our platform has AI and if it doesn't, it kind of gets fallen by the wayside. So for you, what interests you when someone approaches you and says, hey, Ali, I'd like to pitch you on X, Y, and Z to add to your tech stack or I'm interested in doing something with your company like,

Ali (15:17.408)
Mm -hmm.

Adam Sockel (15:35.308)
How do people get your attention to someone who is living and breathing this outreach space?

Ali (15:42.146)
Yeah, I mean, the thing that the way I like to look at AI right now, maybe this will change, but the way I love to look at it is what AI tools can I use to allow me to be more human? So for instance, if I'm on a call and I have a really good process in AI note taker, there's a ton of note takers, right? Lots of note takers. But your selection of products and your customization of that product should depend on whether or not you can be fully committed to a conversation or over here trying to frantically take notes at the same time.

Adam Sockel (15:52.203)
Mm -hmm.

Ali (16:09.954)
And I know people that have had AI note takers in their meetings and they still frantically take notes because they don't trust the AI note taker. Is it the AI note taker software fault? Is it their fault because they never customize it to fit the way they run meetings? Do they run, do they need to run meetings differently? All of those questions for me come into pass and I have one that I love and it allows me to get out, follow up communication faster. So me as a human, I believe that follow up is very important. There should be a follow up email by the end of the day out to that person with the key things we talked about.

this AI tool I found is the best at that with further customization. And then I found that that is the best in briefing our team instead of having to do a like 15 minute handoff of a meeting. I just summarize the key pain points and interests and send them to the rep. And that's actually the best thing. I don't have to actually do a 15 minute meeting anymore. So that's the way I think about it. Can I be more human? Can AI actually go through and identify all the folks in our CRM that happen to be, you know,

Adam Sockel (16:55.468)
Mm -hmm.

Ali (17:04.898)
stagnant, they haven't done anything for a while, and can it also help me understand who is worth the phone call, who is actually bounced or not worth anything. It's some of that sort of stuff that I think I'm more excited about. And then, man, we just, for me overall, like the ability to brainstorm better ideas, that's where I think a lot of us are finding success. And I personally, I am finding a ton of success in using AI and idea generation strategy.

Adam Sockel (17:30.156)
Okay, it can be work related or not work related, but what is, can you give me an example of that? Because I will, I'll kind of give you one to let you think about it, but from an AI standpoint, I'm a distance runner and I recently, I ran my most recent marathon relatively recently, and now I'm transitioning to half marathons because training for marathons is exhausting and I want some of my time back in the weekends. And so I asked chat GPT, I based it was like.

Ali (17:50.946)
It's a lot. It's a lot.

Adam Sockel (17:57.644)
Here was my most recent marathon. Here's the pace I ran. Here is my training. In X amount of months, I'm running a half marathon and I want to hit this pace, built me a training regimen and it did. And so I love that. So that had nothing to do with work, but it was one of my favorite ways I've used it so far. What is one of your favorite ways you've used AI to brainstorm something again, work or non -work related?

Ali (18:06.977)
Mm -hmm.

Ali (18:21.986)
Yeah, well, there's two ways that I use AI and one of them might be giving away some secrets, but I'll say here in a second. The first way non -work related is, I don't know, so I don't think you're a parent, but I have two boys in the schools, anybody who is a parent and they deal with school communication. I love schools, but they tend to email you and text you and like, they don't send you meeting invites like we're used to in this B2B world. So they send out an email with the dates in them. And I just, I'm like,

I don't have time to read all this and go through all this, so I'll take the emails and throw them through AI and basically say pull out the key dates, throw them in a spreadsheet in a CSV and upload the, like I can upload that to my calendar.

Adam Sockel (18:55.82)
That's amazing. That's...

Ali (18:56.738)
Yes, so I'm always like how was how could I literally do this every day every day I have a notion template and it's called daily review and every day I have key questions I ask myself and I'm like, where did I feel like I could have like I shouldn't it was it was hard today Why was this hard or take too much time and how can I automate this? So then I'll you know, that's that's my hobby essentially is trying to figure that out work related one place that I have found this to be helpful is I mean this might be a little bit on the like don't everybody do this but I

Adam Sockel (19:04.299)
Mm -hmm.

Ali (19:25.73)
When I'm on a Zoom call and I'm on with, let's say, a community of people, or if I'm on a webinar where they actually have everybody's names instead of actually being a webinar, they actually have a meeting, I will screenshot the meeting with everyone's names on there, throw that picture in a chat dbt, ask it to read the picture and give me the names, run it through Apollo, and then go and find all the people and actually reach out and connect with everyone that was on that meeting.

Adam Sockel (19:29.099)
Mm -hmm.

Adam Sockel (19:47.818)
You are a genius.

Ali (19:49.154)
Yeah, if you do that, please do not abuse that privilege, please. But I do. And the reason around that was every community I'm part of talks about the value of the members. But honestly, the interface and the ability for me to go find that contact information is time consuming. And so when I figured out this little trick of just screenshotting the members on the screen and having chat GBT, you have to pay the $20 a month to get that feature. But man, that's.

Adam Sockel (19:53.803)

Adam Sockel (20:07.628)
Mm -hmm.

Adam Sockel (20:15.115)
Mm -hmm.

Ali (20:18.05)
That's been really effective.

Adam Sockel (20:21.004)
I promise I will only use that power for good. I won't. I feel like you can see my brain like churning. I was like, my God, this is such a good idea. I love that so much. Yeah, everyone don't be spammy. Like use it respectfully. Use the power that Ali has given for good.

Ali (20:22.786)

Ali (20:35.714)
Yeah, if you send a LinkedIn invite also after that says like, hey, I see that we're both supercharged sales leaders. Don't say stupid stuff. Say like, hey, I was on the XYZ community call with you. I'd just like to reach out and connect. That's perfect. You can use that same message to everybody.

Adam Sockel (20:52.075)
I honestly, I love when people do that, whether it's a webinar I'm moderating or I'm just a part of. That's some of my, those end up being some of the people that I chat with the most frequently. So that part, yeah, I fully, I double stamped that all day, yeah, 100%. So, okay, let's have some fun. I've got the third segment of this podcast is all about just a couple of lighthearted questions. So the first one is, what is the first job you ever had?

Ali (20:57.217)
Mm -hmm.

Ali (21:16.226)
Yeah, my first real job was most likely, I'll say it's working as a waitress at Pizza Hut, which for those of you like this is way back when when Pizza Hut had locations and they had waitresses. And I think my minimum wage was like $3 .50 an hour or something terrible because you're supposed to make it up in wages. But what I learned there was the importance of listening to what people don't say. So it's like, OK, they would say, let's say I'm going to have a whatever kind of pizza. And then you would see them talk to Johnny, the little kid, and be like, what kind do you like? And I.

Adam Sockel (21:29.547)
Mm -hmm.

Ali (21:45.858)
So then you'd know how to cross -sell, upsell. Well, did you know that you can actually just get a personal plan for him by himself? And so it was these like little skills. And then I worked with my best friend. So it was just, work was fun. You could win. And then I would use all my tips and go buy donuts at the gas station on the way home because my parents didn't ever buy donuts. Like it was just this kind of fun time to learn sales and customer service.

Adam Sockel (22:03.627)

I just to like, not my first job, but one of my first jobs when I was in grad school, I bartended actually at the college that I was attending. Yeah, great skill. Like you said, I feel like everyone should work in like the food industry of some sort, but I'm laughing because you're like, I would take all my tips and go like buy donuts because my parents wouldn't ever buy that. I would take all my tips and go gambling. So I don't know what that says about our two like paths in life, but.

Ali (22:14.177)
Great skill.

Ali (22:27.442)
There was nowhere that I could gamble nearby, like literally nowhere. I mean, yeah, the closest I could have gone is maybe like gone and bought some pickle cards, but my win rate on that kind of stuff is just so low that it's just, no.

Adam Sockel (22:37.706)

Adam Sockel (22:43.147)
Yeah, that's fair. What was your worst job? This could be from when you were a kid. This could be, you know, as an adult, whatever. What was your worst job?

Ali (22:50.626)
Yeah, I had a job that I think I would put in the worst category. I was working at a, not because the facility itself or the, or the place was bad. I worked in an assisted living facility for a while in the kitchen and you have all different types of things you're preparing, you know, different types of diets. But the person that I worked with there, it was just a very negative environment. And so I realized at that point that, you know, I was dreading going to work every time I was on break. I was like trying to get myself as far away from the coworkers as possible. It just.

It taught me a lot about the importance of culture and how if other people hate their jobs, you just become part of this like cynicism of talking about hating your job. And I just didn't want to be that person. So that didn't last very long, but I did learn a lot working there, but I think I learned that who you surround yourself with is as important as the job itself.

Adam Sockel (23:37.419)
Yeah, one of my earliest jobs when I was in high school, my dad had me work at a foundry, like pouring concrete that they would then pour liquid metal through. And so it was like 120 degrees in this space and we would pour this concrete and you had to wear long sleeves, which makes me laugh. They're like, well, there's liquid metal around here. You have to wear long sleeves just in case as if that sleeve is going to protect you from liquid metal. And it was my best friend and I, we worked there.

Ali (23:45.986)

Adam Sockel (24:02.923)
And I would, I would notice to your point, like there were some days where we were working so hard, but we were surrounded by like these people who genuinely loved manual labor as their jobs. And then there were other days where these people were just miserable. And you're absolutely like, I found myself not minding this very challenging job on the days when I was surrounded by, by good people. And I think that is such an important lesson to learn. Like that's one of the reasons I love the Orem team so much is not just because I'm representing them on a podcast like this, but because they're great people. And that makes.

Ali (24:11.905)
Mm -hmm.

Adam Sockel (24:31.915)
that is such like if anyone listening is an account executive or an STR and you're like miserable, it might be because of the people surrounding you. And that's such a good lesson. I love that so much. That's so wonderful. What is your favorite app from a productivity standpoint that you use for work? It could be like a GPT type thing, but what's your favorite app from a work standpoint?

Ali (24:41.474)
Yeah, definitely.

Ali (24:53.283)
Yeah, my favorite app is one that I got about 10 years ago. It's called Focus at Will. And it is a, I mean, back then they were probably one of the only ones doing this, you know, even before Spotify started releasing kind of like work playlists. But it's a app that has neuroscience based, I guess music, as you could say. And you can either do timed pomodoro type techniques and it has different levels. There's settings for ADHD, but I bought a lifetime subscription for $99 about 10 years ago.

I feel like that's one of the best, you know, you have like the list of like best purchases in your life and that's been one, but I've used it so much that when I use the app and I turn it on and I do what I would call my deep work, my brain is just Pavlovian. Like my brain's like, all right, we're doing this now. So unlike the lo -fi playlist you might see on YouTube or Spotify, this like the quote unquote songs and sounds are all the same every time, depending on what you listen to. So my brain just goes into that space.

Adam Sockel (25:21.483)

Ali (25:48.995)
I think the other, the reason I like it is I am a classically trained musician. I also am a very like, I can hear a song, play it on the radio and in two minutes later, I can play it on the piano. Like I just, I have that thing. So if I listen to classical music, I can't concentrate because I know where the melody is going. I know all, like I know all the things. So I find myself getting wrapped up in that. So I, this kind of like focus it well, not really melodic type of stuff just gets me in that brain space and.

Adam Sockel (25:58.955)
Mm -hmm.

Adam Sockel (26:07.178)
Mm -hmm.

Ali (26:16.354)
I use it every morning to plan and brainstorm.

Adam Sockel (26:20.171)
That's amazing. Do you have a favorite app for fun? It could be TikTok or Instagram or Strava is mine because like I said, I'm a distance runner. Is there something that you love to use for fun?

Ali (26:31.043)
Hmm, I think that that's a good question because it kind of depends on what I'm doing. I would say there's two apps like I love playing this. I don't play a lot of games on my phone, but whenever I travel, I play Candy Crush because if you don't play it for a while and so it's been like, let's say 30 days, then they're like, thanks for coming back to the app. Now you get like 75 lives. And I'm like, OK, that's enough for my flight. So that'd probably be one. And I think the other one would happen to be I'm a big reader. And so I love the Libby app where you can check out books from the library.

Adam Sockel (26:42.026)
Mm -hmm.

Ali (27:00.931)
And I've checked out so many books that I don't feel bad. So I'll like check them out and then I'll read a little bit. I'm like, eh, this isn't doing it. So I'll put it back. I feel like that gets me going.

Adam Sockel (27:11.339)
Did we talk about the Libby app before this conversation? The reason I ask is that I used to work for Overdrive who built the Libby app and for, we, okay, I was having a deja vu cause my job, people who are listening in, I don't think I've talked about this on the podcast, but my job was B2C marketing for the Libby app for almost a decade. So I'm going to take credit for Ali having heard of that because that was my entire job is to make sure that millions of readers knew about it. But I will double stamp that. I still.

Ali (27:15.011)
I don't know, maybe.

Ali (27:19.747)
wait a minute. We must have yes. Yes, because you were like overdrive.

Adam Sockel (27:39.019)
I obviously no longer work for Overdrive, but I listen to audiobooks every single day. So get yourself a library card. It is free and then you can borrow books on your phone. So I double tap that. What is your ideal workday?

Ali (27:47.029)
Yeah, definitely.

Ali (27:52.259)
Ideal work day is definitely half of the day has to have some sort of people involvement. So interviews like this are great because I get a chance to kind of work human -human. I would love to be in person at an event if that would happen to be an opportunity, kind of an after work sort of thing. I'm definitely extroverted, but not to the point where, like I'm extroverted in work. I don't necessarily like, I'm not like, I don't like going to public events, concerts, that kind of stuff. Like I'll go with a friend, but I won't go just because it's like cool or something.

Adam Sockel (28:01.002)
Mm -hmm.

Adam Sockel (28:20.617)
Mm -hmm.

Ali (28:21.347)
I'm also like the least cool person probably people know. But I think the other half of the day would be, you know, really getting to create content. Like I, sometimes editing can be a drain, but I love taking a raw product and producing this like really compelling, stitching the story together. And so I love being able to do that. So some of my best days are recording content, editing it down, and then kind of getting it to the point where it's ready to release. But ideally it's solving problems and it's getting some good deep work.

balance with, meaning with, and talking to people.

Adam Sockel (28:53.29)
And then last question for you. I've been asking everyone what is a cold call opener that they would hear that would get them to at least hear the pitch. But I'm going to let you use cold call or cold email given the space that you're in. What is a message you could get from a stranger that would at least you would continue letting them pitch you.

Ali (29:14.275)
I was thinking that's one that I would give. Okay.

Adam Sockel (29:17.386)
You can give one if you want to, but I am biased because I work at Oram. So if I get a spam call, I'll pick it up. And if they're kind and genuine, I'll be like, all right, give me your pitch. We'll see what happens. But I didn't used to be that way. So I'm always just curious, if you pick up the phone and it's a cold call, what is something that would at least get you to be like, OK, let me hear your pitch? And again, it could be an email. But I would also love to hear what you would do to get someone's attention.

Ali (29:44.099)
So I'll give you two. I'll give you what you could use. Now watch, I'll get a bunch of calls. But if you wanted to say, hey, Allie, I found your YouTube channel on HubSpot Hacks. Like if you said that and that was your first opener on a cold call, I would talk to you. Usually what happens is they butcher my name, they butcher my last name, and then they're asking like, there's just too much pause. It doesn't feel like you're trying. It just feels silly. Like it just does. And then if I do get,

Adam Sockel (29:57.481)
Mm -hmm.

Adam Sockel (30:08.425)
Mm -hmm.

Ali (30:11.715)
an email and actually Katie, who you know on our team is also doing cold outreach. And so finding something that I did that you could tell is impacting you in some way and creating conversation about that, that's the best cold opener you can give me. I will respond to that. Even if I'm not interested, I'll respond and say, thank you. Not interested at this time, right? For me, if I were to call somebody or email lately, the phrase that's resonating is,

On a scale of one to 10, how much of a dumpster fire is your hub spot?

And when, I mean, they're like, is 10 the highest I can go? So I mean, we have a program called Fix My Hub Spot for this reason. Like we didn't call it the Dumpster Fire Program, because we don't want you to like send a purchase order to your procurement department. And they're like, what is this Dumpster Fire Program we're part of? But when we say Fix My Hub Spot, people go, yes. And so we're using phrases there. But I think if in cold outreach, it's like,

Adam Sockel (30:45.45)
How often is it a 10?

Ali (31:10.788)
Hey, do you feel like your HubSpot's a mess? Is your HubSpot a dumpster fire? Have you inherited a messy portal? All of those things tend to resonate quite well and they speak to the type of value we provide.

Adam Sockel (31:21.13)
I love that so much. So I will put links in the show notes. But for people who are listening in, where can listeners find you and get more information about your company and everything? What's the best place to track you all down?

Ali (31:33.764)
Yeah, the top two places are gonna be go to HubSpot hacks on YouTube. So search HubSpot hacks where myself and my business partner Tyler in the banner up there, you'll know that we're not HubSpot because it's not orange. And we also have the big giant like unofficial sticker. Cause that's what HubSpot makes us for good reason so that people don't confuse us with them. And then I have a new podcast out called marketing deconstructed. So if you just type in marketing deconstructed .com, you'll head to that landing page. There's some free resources, the podcast itself, got a YouTube channel.

and then you'll end up finding our company page, which is simple strat. It's hard to say, easy to spell, but hard on a podcast to get people to go there. So.

Adam Sockel (32:11.338)
Well, Ali, I really, really appreciate your time. I will give you and Katie a whole bunch of credit that she was the person who first reached out to me and I loved what you guys were doing so much. So now we've had a few conversations. So thank you so much for joining me today.

Ali (32:25.092)
Yeah, thanks for having me and I'll look forward to when this comes out. We'll do a good push behind it as well, because this is a new series, so I'm excited to get some love for folks that are also doing a lot of sales with the Orem platform.


Mad-Eye Moody may have demanded constant vigilance from Hogwarts students, but for Ali Schwanke, the key is creative diligence regarding AI and its impact on marketing strategies.

Ali is the Founder of Simple Strat and hosts the wildly successful HubSpot Hacks YouTube show. She joined the latest episode of Bold Calling to discuss how she consults organizations to navigate AI to ensure scalability, and her heightened awareness about shifting marketing strategies as a founder.

Ali’s team excels at helping organizations improve their HubSpot processes, and it all starts with what might be our favorite cold call opener: “On a scale of one to 10, how much of a dumpster fire is your HubSpot?"

The recent addition of AI to Google search results has massive implications for platforms such as podcasts and video. For a content creator like Ali, understanding how to shift value propositions for her clients and prospects reflects every seller's real problems.

In this insightful discussion, Ali and host Adam Sockel delve into how she’s adapting her approach to AI in both her professional and personal life, offering practical advice that sales professionals can apply in their own strategies.

The conversation concludes with a reflection on the present and future of email, its connection to cold calling, and a deep dive into the significance of working in service industries, a topic that Ali is particularly passionate about.