Collin Stewart: 10:33
Because let’s rewind back to 2012. The cloud is still new, right? They were still the IT admins were still like on prem cloud argument. It was not the dominant.
John Corcoran: 10:46
Cloud had not won yet.
Collin Stewart: 10:48
Yeah, it wasn’t the dominant business model yet. Yeah. And so everybody had just started implementing Salesforce and they’re like, I don’t want to switch and go to another one. And like if I’m going to go to this cloud thingy, I’m going to go do it with Salesforce. The big one.
John Corcoran: 11:04
Guy. Yeah.
Collin Stewart: 11:05
Yeah, exactly.
John Corcoran: 11:06
You had one customer in 13 months with Voltage CRM. You must have felt like quitting at some point.
Collin Stewart: 11:14
Yeah. Yeah. I mean, not quitting, but it didn’t feel good. I don’t know how to spell quit, you know? It sounds really cheesy, but I’m super dyslexic.
No. No. Dyslexic with numbers, not with words. And I can’t spell quit. No, I just don’t. I don’t give up easily.
And I, I never wanted to quit. I never had that desire. I wanted to figure it out. I wanted to figure out the answer to the problem. And it was.
John Corcoran: 11:44
And so you pivoted into carb and was that the answer to the problem?
Collin Stewart: 11:48
Kind of. Yeah. Because effectively the answer was like, if we go and look at like, why was I in the situation I was in, the diagnosis is I wasn’t listening to customers or prospects. I had interviewed them like, aren’t I a genius? Goggles on.
And I was only listening to what I wanted to hear. And when I put those down and I started asking people what problems they wanted to solve, what I found was that everybody had these problems. Everybody recognized the insight and the problems. Everybody saw it as well. But the people who experienced that most frequently were sales development reps were these people that had extremely high volume of activity in Salesforce.
They felt it the most because it would take three minutes to send a single email. And like some. It took 15 minutes to send an email. A single email.
John Corcoran: 12:41
So what? What did your offering become after you started listening to the sales development reps? Did that offering become? We’ll help you increase the throughput.
Collin Stewart: 12:54
Yeah. Effectively. I had at the same time as we were figuring out that, hey, this voltage is not something that’s going to work out. I had read Predictable revenue, and I’d started using it to book these meetings for myself, and I started recognizing that, hey, I think folks that are doing the same thing that I am are probably going to struggle and might benefit from some of the hacks that I’ve thrown together in order to reach everybody. Because in order to book all these meetings I had.
I’m not joking. I booked 150 meetings in a couple of months. And like, that’s an extreme number of meetings to do solo because cold email worked extremely well back then. But I hacked it all together with a couple of Google scripts in, or I think they were called Google Apps scripts. It was basically macros in Google Sheets at the time, and I was really fast at finding folks’ email, and I was really fast at copy pasting stuff on LinkedIn.
John Corcoran: 13:44
So probably sending from your main domain. Oh yeah. Which, which of course people can’t do now. You’ll get yourself banned by Google.
Collin Stewart: 13:52
Yeah yeah, yeah. Exactly.
John Corcoran: 13:54
Yeah.
Collin Stewart: 13:55
Yeah. And so yeah, I janked a whole system together and then kind of recognized that one. I think sales development teams might need some help. And then as in the discovery process for that the folks just started asking me that like, hey, how did you reach me? Can I see what you did?
And I started showing them and they asked me to start implementing those systems for them. And so I started building these sales development systems for folks in probably 20 late 2012, early 2013, something like that. Yeah. And, and that basically pulled us into a services business where we were delivering. We were basically doing the product that we were offering, the product that we wanted to build, but as a service, you know.
So The Wizard of Oz kind of paid no attention to the man behind the curtain kind of version of the service.
John Corcoran: 14:43
And you went from growing past $1 million in revenue in three months. Was this the service that you did that with, or was that. Am I jumping ahead here?
Collin Stewart: 14:56
Yeah. So we got up to we got the service up to about a million in revenue, but that took a year. And then along that year we built a software product to support that. So instead of the crappy CRM that we were trying to sell, the engineering team said, hey, let’s build something to support this. And so we took a year to build that out.
And then when we launched it, the launch, the software. So our team had been using it internally on behalf of customers. And then when we started selling it externally, it just caught on like wildfire. And that’s when we went. The software itself went 0 to 1 million in three months.
John Corcoran: 15:31
Wow. And what were. And there must have been some big challenges in that period of time. When you take something from an internal tool to an external tool and you add that amount of revenue on top of it. Did it break along the way?
Did you, you know, run into unexpected challenges?
Collin Stewart: 15:46
Everything broke. Yeah. And that’s the reason software doesn’t exist today. I think the one of the core bad decisions I made back then was my engineering team. My CTO, co-founder Preston said, hey, like the right way to do this is to not build off this janky CRM system that we’ve been just frankensteining together as like tests and things. The right way to do it is to start fresh and like purpose, build something for this new startup because it is a new startup.
Even though we’ve got something that kind of works, we should just start fresh. And I went, no, we need to, you know, we need to get to like feature parity or we need to get to like X so quickly because I just wanted to. I didn’t want to wait. I didn’t want to lose any momentum. I wanted to get as much revenue as we could as quickly as possible.
And I didn’t understand the depth and complexity of what I was saying no to, like my co-founder, who was very good at articulating it, and I see my previous comments weren’t very good at listening back then. And so I didn’t do any listening. And ultimately, when we scaled 0 to 1 million in three months, it put so much stress on the servers that basically like we were Ruby on Rails, and if any technical folks are listening, are active, like active record, just couldn’t keep up. And like every one it just got swamped. And so you would go to click send to send an email and it would take two weeks for it to work its way all the way through.
John Corcoran: 17:12
Oh, geez. Wow. Yeah.
Collin Stewart: 17:15
And then our server costs went up because we’re like, oh, we’ll just try and we’ll just try and outmuscle our poor code with money. And so I think our AWS bill or I think we were Heroku and then we moved to AWS and we had these like dedicated instances and it was like tens of thousands of dollars a month for servers.
John Corcoran: 17:32
Wow.
Collin Stewart: 17:33
I’m like, yeah, it was not good.
John Corcoran: 17:36
I want to ask you. So you said you’d read Predictable Revenue. I read that book. I don’t know, ten years ago now or something like that. A great book based on Aaron’s experience with, you know, putting sales.
Yeah, yeah, putting the sales force in, in, in, in place. Ironically, that’s kind of like the big bad wolf, the demon that you were fighting against. And then you eventually acquire predictable revenue. So you kind of become CEO of a book company. I’m always curious about how people end up partnering with someone that they admire from afar, like an author of a book that was so impactful.
Like, what was the initial conversation like? Did you reach out to him and say, hey, just want to let you know, I really admire the book or what was the initial, like, outreach to him?
Collin Stewart: 18:24
Yeah, my buddy James Clift had stopped me in the hallway and was like, hey, I know you’re trying to do this idiot thing and taking on Salesforce. They just published a book, or one of the guys who worked there published a book outlining how they grew so quickly. You should probably check it out. I bought the book immediately. I read the book the guy wrote, like Aaron wrote a book on cold email, and I figured it’d be rude if I didn’t send him a cold email.
John Corcoran: 18:49
And so yeah, I did. I think he might have encouraged it in the book, I can’t remember, but I thought I thought it said something like that in there, but I’m sure he got a lot of them.
Collin Stewart: 18:57
I was already a dirty sales guy, and so I knew how to find folks, email and phone numbers and all that. And so I sent him an email with a couple of quick questions. I don’t remember specifically what they were, but I found all his information. And then I was basically his internet stalker for like six months and was building, like, hacking together these janky little tools. And I kept asking him questions and I would follow him on webinars and like, I was his internet stalker.
I think they call it social selling now, but back then it was called stalking somebody.
John Corcoran: 19:26
It’s a nice term for stalking. Totally.
Collin Stewart: 19:29
Totally not stalking him. But, like. Yes, I was stalking him. Yeah. And then it just came to a point where he was like, hey, we should find a way to work together.
And I was like, what do you mean by that? And he’s like, I think we should like, merge the companies. And so, yeah, that was 2014. We finally got the deal done around October 2014, something like that.
John Corcoran: 19:48
What year did the book come out?
Collin Stewart: 19:51
I think it came out in 2010.
John Corcoran: 19:53
Okay. All right. So I’ve been around for four years at that point. Yeah. And what.
Collin Stewart: 19:56
Something.
John Corcoran: 19:57
How did one plus one equal three? Why do you think merging the companies made sense?
Collin Stewart: 20:03
I mean, he had this methodology and this exposure, but he was bottlenecked on time, right? Doesn’t matter how much you charge by the hour, if your time is still bought, if your revenue, your income is still bottlenecked on your time. Right. He had no way of decoupling those two things. And I think he saw a carb and the things that were being built as a way of helping bootstrap the software company into existence.
John Corcoran: 20:27
And then what did you do? Did you at some point, throw out the old system built on Ruby on Rails and build something new? Or how you had all these clients that you’re running through it?
Collin Stewart: 20:37
Yeah, eventually we did, but it was too late. And like, we lost our momentum. We lost our like the positive word of mouth. Like the reason carbs went from 0 to 1 million is when we hit on an extremely valuable pain to solve. And we also hit on something that was extremely painful.
Right? Like the combination of those two things where these salespeople that are making a company money are bottlenecked on a process. And if you can fix that bottleneck, it is worth a ton of money to the company. And so every salesperson, every sales leader that had this problem, if they heard that somebody was trying to solve it, they were like demanding intros. Like when I first launched the service, the service version of the software, not even the software.
I was like, Hey, Preston, to my co-founder. I’m like, I’m sorry about this whole CRM thing that nobody bought my commitment to you. Before I ask you to write another line of code, I’ll find five paying customers too. I’ll do this manually. I’ll find I’ve got the process I think I can handle five max.
I’ll see if I can get them to give me 500 bucks a month, just for one month, and we’ll see if we can do it. I had five meetings and I came away. I came away with seven customers.
John Corcoran: 21:47
How’s that even possible? Like they signed up their buddy down the hall. Yeah, literally.
Collin Stewart: 21:51
Yeah, yeah.
John Corcoran: 21:52
Two of them.
Collin Stewart: 21:52
Called in the meeting. They called their buddy. They’re like, hey, I’ve got this guy here. He says he can do it. He says he can do cold email for 500 bucks a month.
Are you in? And the guy’s like, hell yeah. And so.
John Corcoran: 22:03
So that must have been like finding an oasis in the desert after your 13 month experience of only having one client.
Collin Stewart: 22:09
Yeah, like I liken it to pushing a giant rock up a hill and suddenly it’s running downhill and you’re like, I gotta keep up to this thing.
John Corcoran: 22:16
Yeah, obviously today in 20, 20, 25, it’s a totally different animal. There are tools like instantly, Apollo, Zoominfo, stuff like that. What do you say the world is like now as far as cold email, is it still effective? Is it no longer as effective?
Collin Stewart: 22:34
It’s still effective. It’s the. But the table stakes have gone up. Have you ever played poker or sat at a casino?
John Corcoran: 22:41
Yeah.
Collin Stewart: 22:41
You know, you used to play with, like, nickels and dimes, you know, with your buddies. Yeah. And then you go to the casino. It’s a dollar. It’s like one, two, no limit.
John Corcoran: 22:49
Yeah.
Collin Stewart: 22:50
That was kind of the early days of, like when I started playing cold email was like one to no limit. And now it’s like the blinds are 50 on 50, 100. You know, you need a significantly larger stack of cash to sit down and play outbound and, and get value out of it. So there’s still lots of companies that are getting tons of value out of it, but it’s significantly harder to do.
John Corcoran: 23:11
So you need to be more patient. It takes more time.
Collin Stewart: 23:18
You need to be more. I guess clever and personalized and like, I don’t want to be discouraging and saying, oh, it’s impossible for regular folks to do it. It’s just that it’s quite challenging. Like, I work with a lot of startups and help them build their first outbound teams, their first sales teams. And like when you’re a startup, you don’t know enough information to craft a really great cold email.
And it’s not it’s not it doesn’t just come down to writing the message. It, like most companies, screws it up in building the list because when you think about what goes into getting a reply, it is the targeting of how you built that list and the signals that and the reason you put somebody on that list. Married to the content that you are sending them. It’s those two things working together that creates the real magic. Right.
And I find one a lot of companies aren’t very intentional about putting those two things together. Right. And kind of the messaging should draw the through line of the through the targeting of like this is why this account is on the list. This is why this contact is on the list. And this is why this contact should be just rare.
Roaring to reply to us right now. This is why it’s super relevant and very actionable and it’s actually going to help them. You and.
John Corcoran: 24:32
Sorry.
Collin Stewart: 24:33
Go ahead go ahead.
John Corcoran: 24:34
Oh you mentioned earlier social selling which is a popular buzz term these days. Do you do you believe in that or do you believe in continuing you know, email is enough or do you is it does it depend on depend on budget? What are your thoughts on that?
Collin Stewart: 24:49
Yeah, I think it all depends on what you’re looking to accomplish. Social selling works, cold email works. The phone works. Going and knocking on doors works. I bet you if you sent homing pigeons to somebody’s office, you’d get a reply too.
You know.
John Corcoran: 25:02
That’d be pretty cool, honestly. Like this pigeon showed up on my windowsill. Yeah.
Collin Stewart: 25:07
One of my clients a long time ago, he was a door -to -door guy. I think he was selling it as Cintas, like the uniform company. Okay. And he he would show up, he’d go buy pizzas and he’d show up at, like, you know, just before lunchtime, and he’d walk in with, like, ten pizza boxes, but he would get he would buy ten pizzas, and then he’d ask the pizza shop for 20 pizza boxes, so he’d get ten full boxes and ten empty boxes. And then he’d take the empty boxes in and be like, hey, pizza delivery from, you know, me at Cintas.
And then the first one had a note like, hey, if you take a meeting with me, I’ve got the pizzas in my truck.
John Corcoran: 25:48
Okay.
Collin Stewart: 25:49
So everybody’s like, hell yeah, pizzas. So I’m sure the pizza truck still works.
John Corcoran: 25:55
You.
Collin Stewart: 25:55
Know?
John Corcoran: 25:55
And I’m sure. Yeah, sure.
Collin Stewart: 25:56
I’m sure. Door-to-door still works. But, like, you got to be creative about it. And I think right now what’s happening is AI, SDR is everywhere, and everybody thinks it’s amazing. But all AI SDR has allowed us to do like any.
I’ve looked at a bunch of AI, SDR tools. I’ve tried a few of them. I haven’t seen any good ones because they’re not the only AI there writing the emails. The AI is not building the list. It’s not figuring out who is targeting, who should be in the targeting.
The AI is not doing any sort of machine learning or analysis. These are all large language model based AI systems. Llms aren’t great for strategy. They aren’t great for the multi-armed bandits or single arm bandits or Monte Carlo simulations that machine learning traditional machine learning is like really, really great at. And so I think what everybody is implying or is thinking is like AI, SDR is like an artificial intelligence powered SDR, but it’s not.
It’s an LLM powered SDR, which means regular cold email deliverability stuff coupled with pretty average cold email messaging written by an LLM.
John Corcoran: 27:06
It’s amazing to me how much people actually don’t. Even when people talk about cold outreach that they talk about, like, where do I get a list? And they don’t. Talk about the messaging piece. And that is such an important piece that people are just kind.
Like whatever, like put a message in there and that makes such a massive difference, especially today.
Collin Stewart: 27:26
Totally. And I think the most important piece is the connection. And like today, what’s really working is finding that signal, finding the reason why somebody is reaching out so that instead of sending 10,000, you know, bulk emails, you can send a few hundred really targeted emails. And I’m not a big AI messaging fan or AI like having AI write the message. I like to write the message myself.
I might use AI to write a couple of custom snippets. You know, to write, you know, like to like, classify your podcast. If I was going to reach out and say, hey, you know, really like you or, you know, X podcast, you know, I might have AI fill in a word or two here or there. Yeah, but I’m not going to have it write the message.
John Corcoran: 28:07
The funny thing about those mail mergers is like, I just got one today that was like a private equity company that said they were reaching out because they had investors in my town that were looking to acquire companies like my company and my town has 9000 people in it. It’s not that many people. It’s a small town. So like clearly it was just a mail merge. They grabbed it off of LinkedIn, put it in there, like if it was like Chicago, San Francisco or something like that, that would maybe make sense.
But it was like, you know, it didn’t really work.
Collin Stewart: 28:36
It seems like they copy and pasted that from like a, like a porn ad that’s trying to get you to cheat on your wife and give you like 100 bucks a month or something like that.
John Corcoran: 28:43
That was probably.
Collin Stewart: 28:44
The fallout back in the day.
John Corcoran: 28:45
That was probably the follow up. Yeah. The Terrifying Art of Finding Customers A Sleep-Deprived Founders Guide to Revenue. What inspired writing that book?
Collin Stewart: 28:56
Running a sales development agency for as long as I did where it started was I recognized that a lot of founders were leaving money on the table in that they would We would run all these campaigns for clients where you’re prospecting, and then you’re booking a bunch of meetings and you’d see a customer, you know, like building an outbound team. Like the reason most companies don’t make it off the ground with outbound is they don’t invest the right amount of time. Right. They get mediocre results in the early days and they go, yeah, it’s not for me. This doesn’t work.
And what they should be saying is this hasn’t worked yet or we haven’t figured it out yet. Outbound from when you think about the investment profile, it sucks because you have to invest a lot and you get nothing. And then if you keep testing and tweaking and tuning, eventually you get something and then you get something extremely scalable because like, once you’ve figured it out, once you’ve cracked the code, then it’s it can be one of the like, best costing, customer acquisition, customer acquisition channels out there. But most companies don’t get off the ground with it. And where the book initially came from was I started writing a book calledThe Four Funnels, which was my frustration out of my frustration of seeing our clients come get these meetings, and we’d spend six months, nine months working with them.
They’d get a bunch of meetings and their AES would go, yeah, there’s no there’s no project in the next 90 days. So I’m not interested in talking to them.
John Corcoran: 30:24
And the challenge there that they the A is it compensated and that 90 day window. So they don’t care about a project that’s, you know, 180 days from now.
Collin Stewart: 30:34
Yeah. It’s the AES didn’t want to put the work in, and the company didn’t have a great process for tracking all these conversations, because with cold email, what you’re doing is you’re basically taking a company that you don’t know, and you’re reaching out to start a connection and then like to reach out and say, hey, can I sell you some shit? Yeah, sometimes that works, but only if they’re like, really in pain. Yeah, but to reach out and start a relationship and say, hey, I want to get to know you and to have folks reply back and say, yeah, let’s have a chat about it. I’m interested.
And then to have your salesperson say, yeah, you know what? You’re not far enough down your buyer’s journey. I’m not willing to put the work in is a crappy move. And so I found a bunch of companies were wasting money on this and that if you if a customer would just or if a company would just take those meetings, work them and then put them into their nurture funnel where that AI is working them, you know, once a month, once a quarter, just sending them a light follow up, keeping them in touch, keeping in touch with them. You get so much more like it, we even saw this when we hired our first SDR.
We got nothing for the first six months like zero deals, and we’re the company that had gone zero to a couple million dollars building our own service. It still took us time to figure out all the variables for us to get our own SDR going. It took us six months, then we got a deal every other month for the next six months. So we got three deals in the first year. It absolutely did not pay back the costs.
But then suddenly at the 12 month mark, we started to get a deal a month, and then we got a deal a month every month. And then we were able to scale that up to every SDR we added in about 3 to 6 months. They were adding a deal every month like that. Customer acquisition channels scale extremely well. And the thing that we did really well was we were reaching out to start a relationship, and then we were able to effectively nurture the relationships with those folks so that when they were ready, when they went from, yeah, I’m thinking about it to, you know what?
Yeah, I want to actually buy some outbound or I want help with outbound. We were the company that had just talked to them, and we had been in contact with them and sharing helpful docs for three, six, nine, 12, 18 months, whatever it took. And that’s really what it took. And that was really the thing that people missed was that, you know, everybody was looking for quick, quick money, easy money and thinking that, you know, buying a sales development team was like buying ads and it’s not. And so I started writing the book to kind of help with that.
And then I slowly realized that I didn’t really love sales development. It wasn’t like the thing that I was put on this earth to do. It was something that I was good at. at. But what I really wanted to do was help founders figure out how to find their first customers, and then how to go from once you found your first customer, or once you’ve kind of been in that customer development process where I got stuck, how do you draw a line between customer development and closing your first customers?
Because I was the sales guy at the co-working space where I worked and like where I started this company and all of my friends were engineers, all of my entrepreneur friends were engineers, and they all came to me with like, Hey, Collin, how do I how do I sell? How do I find my customers? How do I, like, get this? And like, what everybody was missing there was that you would do all this customer development research, like even I did it. I interviewed 150 sales leaders, and then I pivoted into Carb, and I didn’t go back and I and talk to them, you know, like if you’ve got 150 relationships with folks that say they have the problem, don’t you think it’s a good idea to go back and say, hey, remember that problem you told me about?
We’re solving it now. Yeah, and it seems super obvious, but most founders don’t do it.
John Corcoran: 33:58
Yeah. So then, is The Terrifying Art of Finding Customers… Is it? How does it relate to Predictable Revenue? Is it like the precursor to Predictable Revenue?
Collin Stewart: 34:10
Yeah, it’s kind of the prequel. Prequel?
John Corcoran: 34:12
Yeah. Yeah. That’s cool.
Collin Stewart: 34:14
It basically, it basically helps you go from trying to find your first customers and like strengthening your product market fit and the customer development process to how do you actually close and close those customers, and how do you basically look at the customer development funnel of going from learning to earning, and then how do you sell? How do you build your first sales team? So kind of a light touch on those second two pieces. But yeah, that’s the line I was trying to draw for folks.
John Corcoran: 34:38
That’s great. Well Collin, this has been great. I want to wrap up with my gratitude question. So I’m a big fan of giving our guests a little bit of space here to shout out any peers, contemporaries, mentors, investors, business partners, anyone in particular that you want to thank for being there with you over the years?
Collin Stewart: 34:59
Yeah, I think, you know, you asked this at the beginning and I’ve had a couple of I had a couple of thoughts, but I think the guy who’s who is most deserving of a shout out right now is my buddy Kenny McKenzie. There’s a couple pieces in the book on the market fit process, and it was just something that Kenny and I ended up working together on. And, you know, everybody has co-founder issues. And like, I was probably the root cause of most of the co-founder issues. Our co-founders had.
And so there was a lot of turmoil. And then Kenny came and joined the company. I don’t know, like ten years ago. I worked with us for maybe two years. It was the first time I felt like I had a positive, like, relationship with a co-founder.
And so Kenny and I stayed in touch. He’s got his own company now, feedback machines. But he had a tremendous impact on helping me understand customer development better, helping me, I don’t know, figure out how to lead people. And then he and I just always stay in touch and kind of push each other. So we have like a monthly ongoing call where it was just a, you know, it’s half like buddy buddy check in and have like, hey, help me with the work thing.
Yeah. And so that’s a relationship that I cherish.
John Corcoran: 36:02
That’s great. That’s great. Well, this has been great, Collin, where can people go to learn more about you and learn more about the book when it comes out?
Collin Stewart: 36:09
Yeah. You can find more at terrifyingart.com if you want to. You know, if you liked me blathering on about sales and customer development and stuff, I write a weekly newsletter called Founder’s Edition. It’s foundersedition.co.
John Corcoran: 36:22
Yes. That’s great. All right. Definitely sign up for that. I’m on the list.
I was just reading your message this morning. So it’s definitely valuable if you put a lot of content in there. So that’s really not one of these like you know newsletters that just kind of like you forget about. You actually put a lot of thought into those newsletters. So good job on that, Collin.
Thank you. Thank you so much.
Collin Stewart: 36:40
Thank you.
Outro: 36:44
Thanks for listening to the Smart Business Revolution podcast. We’ll see you again next time and be sure to click subscribe to get future episodes.