Dr. Jeremy Weisz: 12:45
Yeah. Messaging because I’m sure you’ve seen everything under the sun at this point.
Collin Stewart: 12:50
I mean, I think people care too much about their message, like especially with cold email or like a cold call because you’re writing it down. You’re like a human is saying it. I see a lot of founders thinking, oh, I’ve got a I should have a weigh in on this, and I should be able to dictate the words that you say, when in reality it should be a combination of the practitioner and the founder. Like obviously the founder is going to know, you know, the product and the market and the opportunity and the problem space and all of that. But the sales team are the ones that know the tactics of what’s going to work and how we’re going to get it and how we’re going to start the conversation. It’s sort of for the same reason that the founder doesn’t go and sit and look at your SEO keywords and go, no, don’t focus on those ones. Focus on these ones like, you would never think to do that because that’s a silly idea. You’ve got a certain set of SEO words that you rank for, and obviously they’ve got to be relevant to your business. But if you’re not like, it’s not like the founders coming in and going, oh, you have to rank for this one. That’s like way down on the chain that doesn’t matter. And like I guess I’m as I’m saying that I’m like, yeah, I’ve done that before. But I think the mix of like it’s got to be a mix of, of both coming in because there are just certain ways of opening conversations, there are certain ways of writing the messaging.
But ultimately I think the messaging to my first point, like the messaging doesn’t matter unless you have a great target audience. And I think the even bigger challenge I’ve had with founders is not being specific enough about the target audience that they’re going after. You know, I’ve been the salesperson off and on for PR for 13 years and the number of founders I’ve talked to and I’m like, hey, so who do you want to target? And they’re like, I want to go after, I don’t know, manufacturing. And you’re like, great. That’s like 60,000 companies. Like any other criteria. I’m like, no, just manufacturing, you know, the big ones enterprise and okay. And then, you know, like you only get a few criteria and you’re like, great, I’ve got a, you know, 10,000 companies and 40,000 people that I can reach. But, like, how do you know who to start with? And how do you know how to carve up to get to the most relevant. Like, this is going to be the most relevant thing to say to them right now. And the relevance piece is the hardest.
Dr. Jeremy Weisz: 15:05
Yeah. It seems like everything kind of bleeds from the targeting because if you’re, you know, doing farming, manufacturing equipment, it’s going to be different messaging. You can be very precise, very specific. And it’s going to hit home to that audience as opposed to we’re trying to speak to this too big of a niche.
Collin Stewart: 15:23
Yeah, I had two clients that were competitors and friends and they were resellers of this software product and they had one had this state, one had this state. And then they shared this middle state in between them. And I don’t think it was physically in between them, but they shared a state. The one guy told me to bring his friend on, even though they’re competitors and the friend’s like, hey, I’ve got Mike’s list and Mike’s messaging. Can I use that? And I was like, how did you get that? He’s like, well, Mike sent it to me. Like, what? You guys are competitors. Like, this is, we’ve already ran this. And so we used Mike’s messaging to for I can’t the names weren’t Mike and Jim, but let’s call them Mike and Jim.
So we used Mike’s messaging for Jim’s audience in Jim’s state and it bombed like Mike was producing like 20 meetings a month. Jim got like four and he’s like, what’s going on? And it was maybe it was the brand, maybe it was the execution, the timing. But like even the exact same messaging with a different context and a different brand and a different domain name behind it performed differently. And so like, everything’s got to be really tightly calibrated to this is what’s relevant. This is why it’s relevant to me right now.
Dr. Jeremy Weisz: 16:40
Wow. Yeah. That’s like the tale of I don’t remember the direct response copywriting piece on that. Right. And it’s like, who’s two pathways? So I love that story. So, you know, it’s interesting. I remember studying like Gary Halbert stuff, some of the top direct response marketers. And he said there was a point where he says, you know, what’s the number one thing that you want? And the answer was a starving crowd. Right. The right person who’s got a big need to it.
So, you know, on that topic of the journey, right. We talked about Brian, what do you see as just walk me through like a sales journey, a sales team journey, like starting with founder and like some of the recommendations you have. Okay. At this point, you start putting these people in place and what you actually obviously help these companies do. But just so people have an idea starting with kind of the founder.
Collin Stewart: 17:42
Cool. When I was starting my first company in like early in the founder journey, I always worried about, I felt like having a company was sort of like having like a suicidal pet that just kept trying to kill itself. And I was always worried, like the company was going to die and then and just, like, die suddenly and like I was going to be out of control. And the longer I’ve been doing this, the more I realized, like, companies don’t just die. They commit suicide. And the number one way they commit suicide is premature scaling. And that’s investing in growth, investing in things like trying to grow the company from a revenue perspective, trying to grow from a headcount perspective, trying to grow from making all these investments before you have a strong enough connection between your starving audience and the product that satisfies their hunger. And I think that’s the biggest, most important thing I’ve learned. I’ve had I’ve literally helped thousands of companies of startups, and specifically most of them were startups and in like build their first go to market channel. I’ve done it. I think I did the math. It was like 1200 times with startups.
The number one thing I saw was companies were trying to invest in hiring 4 or 5, six STARS, and they didn’t have a very strong product market fit. The founder couldn’t tell me exactly who it is they wanted to go after. If they did get a meeting, it wasn’t like oh, there’s a huge market pull here. It was just a oh, well, we think it’s this. It was a hypothetical. It wasn’t a oh, I know it. And I think to me this is founder suicide because you’re you really you’re the cash in the bank is really your lifeblood. And you only get so many shots, right? There’s only so much time you have. There’s only so much, so many opportunities. And so I’m a big fan of, like, conserve your cash until you’ve got the right you can kind of everything’s lined up and then all right, let’s double down.
And I think the way I see founders kind of making these investments, they’re doing it because their sales is something they didn’t want to do. Right. It’s not they don’t, I don’t come from sales. I don’t come from product or I come from product, I come from engineering. I want to get sales off my plate as quickly as I can. I’m going to hire a VP of sales, a CRO, a salesperson at Oracle. And like, those are all probably terrible hires because you haven’t proven anything like only the founder can prove product market fit, only the founder can prove this is the process to close a new customer. I don’t care if you’re an engineer. I don’t care if the only language you speak is XML or HTML or Ruby, right? Like you, you found the product opportunity, and whoever found that opportunity is the number one expert in that problem space in your company.
And there’s nobody, customers love talking to founders. They love talking to people who understand their pain. And if you’re the guy or the woman that found that opportunity, that found that problem space, nobody in the world understands it better than you. And there’s nothing better than somebody who’s in pain. Who’s that starving crowd looking at the person that invented the hot dog going, Jeez, I’m so hungry. And you’re the hot dog expert, right? Like, there’s nothing better. And so I think the if you’re a founder and you’re thinking about, like, going and hiring some people, prove it first, then scale it up and just make sure that you’re, the product market fit is strong.
And there’s ways of measuring that and quantifying that. And my favorite way there’s a number of different ways you can find kind of like early like first tracks. But I think my favorite way is just referrals. I use this any time I’m exploring a new product opportunity.
If I’m trying to say, hey, should we go open this market? Should I go create this product? Should I go? I’m going 0 to 1 on a side project right now and I’m literally doing this. I’m booking myself 3 to 5 meetings a week. And I’m going and I’m asking folks, and I’m getting meetings because I know how to book meetings. But the thing I watch really closely is of all the meetings and these are I’m doing customer development. I’m not selling anything. I don’t have anything to sell. But I’m the metric. I’m paying really close attention to is of all the people I talked to, how many of them give me a referral to somebody else who I could talk to? Because that’s a gauge of hunger, right?
And really, what I’m looking for, to your point, is that starving crowd, I don’t want to go and spend my time, my life building something that I want to build. I’ve already done that, and it didn’t go very well. I want to build something for a starving crowd. I want to build something like when we pivoted from voltage, which is the CRM company that had one customer to Carb, and it took us a while to kind of figure out that transition. But once we had the product and we started doing the customer development, once we had the idea and we started doing the customer development interviews for it, we went 0 to 1 million in revenue in three months. And that was all on the back of doing customer development interviews.
But there was such a great need that I was doing my interviews and I was asking questions and people were like, no, no, no, stop. You just said this, this and this. Are you really working on solving this problem? And I’m like, well, can I tell you at the end? I just want to get through my questions. And they’re like, no, tell me right now because I want to, if you’re solving this, I want it. I want it now. And I’ve got three friends that also want it because this sucks. This is a huge hair on fire problem. And so, some of.
Dr. Jeremy Weisz: 23:01
What are those key questions that you ask in a customer development session?
Collin Stewart: 23:08
I’m happy to share in fairness, it was about who I was sitting down with and like the pain that they were experiencing. And so I just do day in the life interviews and with Carb, I was focusing specifically on sales productivity for sales development reps. This was 12 years ago. So the sales loft and outreach and I think Zen Prospect or Zen leads Apollo was still Zen leads. Apollo was a data source. Sales loft was a tool for scraping data off of LinkedIn, and outreach was a recruiting tool at the time. And so there wasn’t really a lot of or maybe the three of them were like either there or about to pivot into the sales engagement space. But if you were an SDR 12 years ago and you wanted to send 50 emails, it was like 27 clicks per person. You wanted to email in Salesforce. It was extremely painful. And so the biggest bottleneck for every sales development leader was just automation. Just like, hey, I want to send this email, do all the things to make it appear in Salesforce and everybody sales, everybody had just implemented Salesforce. So everybody’s really hot and heavy on like everything’s got to be in Salesforce.
People were spending like, I talked to one company that spent $500,000 just implementing this system in their Salesforce. And so the question I was sitting down with said, hey, I want to talk about your sales team. Tell me about the tools you use. Tell me about what you love. Tell me about what you hate. And I would ask different questions. I’d want to understand their, you know, their job, their role in the organization, their goals for the year, their goals for the quarter, how they were measured with how they got their bonus and all? This led to the magic question, which is if I could solve any problem for you, what would it be? And everybody said productivity. Everybody, every sales development leader. And in fairness, actually every VP of sales that I talked to that I asked this question, said my sales development team, because there was just so much manual clicking. And so if I ever talked to a VP of sales, they’d refer me to their SDR team or their SDR leader.
The thing that helped like this was a pretty obvious pain. But the thing that really helped kind of quantify between like, this is something that’s painful and this is something that’s painful, that is going to get that we’re going to be willing to part with money in order to solve was the kind of three follow on questions I ask after every magic question, which is scale of 1 to 10, how important is this to you? Scale of 1 to 10? How satisfied are you with how you’re currently solving it? And then what would be the impact on your business or on your job of solving this. And so importance, satisfaction, impact. Importance tells you how pissed off they are about it. Satisfaction tells you how likely they are to move forward with a solution. And impact tells you how much you could charge for it. And in this case, it was ten and ten. Importance two out of ten. Satisfaction. Because nobody really wants to say one in this. They’re like really bad. So like twos and threes are great. And then the impact would be like 3 to 5 x in the productivity of SDR of their SDR team. And so this is a pretty tremendous impact. And that’s basically what pulled us up to a million so quickly.
Dr. Jeremy Weisz: 26:19
Collin, this is gold. I’m going to have to re-listen to this really. And I listened to it at three times speed. I have to slow it down to 0.5 just so I get it. Because this is really important. Anyone who’s launching a product, a new service, this is like golden. So I appreciate you kind of sharing your process with that.
And I do want to talk about a couple favorite stories from the book. You know, people can check it out. Terrifying Art of Finding Customers. You’ve said this. This is your words, not mine, but the $4 million hard drive. I think that has to do with voltage CRM. So talk about voltage CRM.
Collin Stewart: 27:01
Yeah. I mean.
Dr. Jeremy Weisz: 27:02
There was an interview. Did you like my hard drives in my closet right there. And it’s a $4 million hard drive.
Collin Stewart: 27:09
So yeah, it’s right up there now man. You went deep into the archives. So we basically spent a year and a half working on a CRM that nobody wanted. My customer development process was I read all the right books. I read The Mom Test, I read where is it? The Startup Owner’s Manual and Four Steps to the Epiphany. And like all of lean, Lean Customer Development, lean product like all those books.
But the thing I got wrong was I just did all the interviews wrong. I was like, hey, this is what I’m building. Isn’t that great? And everybody went yeah, love it. And then I went and built it and I came back and I was like, hey, we built the thing. And they’re like, good for you. Tiny golf clap. And I was like, damn. And so when I like and I have a good sales person and I’m probably not the best, probably not great, but like good, I could consistently close and so was my co-founder was like, hey, you know how to close. Like why isn’t anything closing? And I’m like, I don’t know, like, maybe I suddenly got the yips and I just forgot. And we didn’t have.
Dr. Jeremy Weisz: 28:15
The sales yips.
Collin Stewart: 28:16
The sales yips, and we just didn’t have a starving crowd. We didn’t build something that people wanted to, and we spent a year and a half of our lives on that. And with Carb, the thing that changed was I started asking questions. I started doing those day in the life interviews. I think the thing that’s easy to miss because the journey happened for us. It happened so incredibly quickly. And one of the gifts of writing the book is that it kind of forced me to look back and recognize some of the things that I’d done. I came. I started my life in sales. I still am in sales, but I learned how to start a company. I learned customer development, most importantly as a salesperson. And what I noticed is that customer development is just the first half of a great sales conversation. And the the biggest piece of the book, the reason I wrote the book is that the customer development world is not connected to the sales development world, and especially if you’re an early founder, if you’re trying to get that first million in revenue, those two, you have to be doing both of those at the same time.
And so I really wrote the book because I’d been, I was just tired of like talking about strength to product market fit. And you need to improve the strength of it before you start investing in go to market. And people kept saying how and I didn’t really have good words for it. And so that was really the genesis of the book, was the idea of the customer development funnel that you can and should sell to those people that you do your customer development research with, because you can’t call it customer development if none of them actually give you any money, because that’s the action that turns somebody from a just a person into a customer. And if none of them turn into customers, you didn’t do customer development at all. You did a university research project where you asked a bunch of people stuff, and then you went, cool. We learned something and you wrote a report, and then you were like, cool, now I got to sell it and you forgot about all those folks.
Like, imagine if your hair’s on fire and you interviewed 50 people with their hair on fire and you’re inventing a fire extinguisher. And if you allow me to stretch this silly analogy, you come back three months later and their hair is still sizzling. I know, silly, but then imagine looking at those folks and being like, hey, thanks for your help building this. And then like turning your back on them and walking away and be like, I got to go find some people to sell this thing to. Like, why don’t you just like their hair is on fire? Like, you could see the sparks. Like, why don’t you go ask them? And that’s where the idea of the customer development funnel came from is that you need to be able to level up the people you talk to in your customer development process from. Hey, I’m just here to learn to eventually sell to them without being a bad salesperson about it. And like bait and switching anybody into a sales conversation. When I do it, it’s very intentional. The first four calls we have are 100% learning only, and I know eventually if they’re going to be in pain, they’re going to ask me to use the product. And I’m if they’re if they don’t, I’m so.
Dr. Jeremy Weisz: 31:00
Naturally come about if you’re talking to the right person with the right problem.
Collin Stewart: 31:04
Exactly. So the first conversation is exploratory. Hey, what problems do you have? Right. The next conversation is focused. Hey, I want to talk about your sales productivity problem. The third conversation is a paper feedback. Hey, I’m thinking about building this. These are the chunks. If I built this with. Do you think that would solve this problem? Right. You kind of lay the hypothesis. Hey, I found this in exploratory. We focused on this, and it sounds like it’s painful. Yeah. Cool. These. If I wanted to solve it with these three chunks. Solve it? Yes. No. Oh. What else do we need to build? Cool.
The fourth step is the MVP feedback where you say, hey, you told us to build these three chunks. We built those three chunks. Did we do a good enough job? Does that solve it? Cool. And then like that’s the customer development funnel. And at the end of that, if they say yes, yes, yes to all of those things, one, they’re probably going to ask if they can use it. Two, if they don’t invite them into a sales process, or even if they do invite them into a sales process, hey, it sounds like this is going to be helpful. Why don’t we set up some time to talk about what it would look like to implement that for rise 25?
Dr. Jeremy Weisz: 32:05
Very simple in your mind. So like we’re talking founder, right? We’re proving it out. We’re finding product market fit. And then you’re like okay we find that. What do you see as you’re scaling up the team, what’s like an ideal team structure is like going from founder to the next phase and then the phase after that?
Collin Stewart: 32:26
Yeah. And just one, if I can kind of nitpick on one phrase, I don’t love the idea that you get product market fit and you have it forever. I don’t think product market fit is something that’s like a binary switch that just gets flipped. It’s not 0 or 1. It’s on a spectrum of weak product market fit to strong product market fit. If I only sold left handed scissors markets very, very small. But you could probably find some customers for that. But if you’re going to sell, I don’t know, a delivery driver and customer flow to restaurants. It’s going to save the money and make them money at the same time. There’s going to be a lot of folks that are going to care about that. And so I think strength of product market fit is kind of the the way I think about things. And as you go and as you progress you, the more you learn, the more you do the do customer development, the stronger it gets, the more you learn and build and adapt. And then when you open up a new market, there are new variables. And so your product market fit isn’t as strong because it’s impossible. The and the reason I kind of nitpick on this is when you sit down with the founder and say you don’t have product market fit, they’re like, no, no, no, I have customers, I have a market. Product market fit. Like it’s there. And I’ve had this argument hundreds of times and I got tired of it. And because they’re right, they do have a product. It is in market. You just don’t have very many of them. And the market’s not very big. And to your point, there isn’t a starving crowd. There was like we just went in Petite Pierre. Which if my French memory is okay. I think it just means like a little bit, but I don’t know.
Anyway, so you have a great starving crowd and you built a really great product for them, then like it makes everything so much easier. Now back to your question about what do I recommend founders from like, you know, how do they build the sales team underneath them? I mean, the first thing is like, make sure your product market fit is strong. And if you’re opening up a new market, just consider that your product market fit is really weak until you know more and it’s not really weak. It’s just you’ve got this equation and there’s a bunch of unknown variables. So you have to assume there’s zeros until you know more. And if you think about it that way, you don’t go charging in with like, you know, a $100,000 a month marketing spend on this new unknown market that might have a sales efficiency of like that, you’re never going to pay back that investment. It’s all about like keeping your powder dry until you’re, like, ready to roll. But to finally answer your question.
Dr. Jeremy Weisz: 34:57
I like how you kind of hound on this point because I’m sure you get the same question I’m asking. A founder comes to you and goes, Collin, I just want to get out of sales. Like, what do I do? And you’re like, wait, before you go to sales, you got to do this product market fit. You got to make sure, because then you’re just going to be spinning your wheels, wasting time, energy and money on a team. So I got you.
Collin Stewart: 35:23
Totally. Yeah. You want to get out of sales, quit your job, go join like a FAANG company. You know, like if you’re a founder, it’s always going to be a small part of your role. And so if you’re the founder, you’re in sales right now. You’re everything is on your plate. What you want to do is look at the what are the least valuable parts of your job, of the sales role? What are the things where you add the least amount of value? And that’s probably prospecting. That’s probably booking meetings. And when I say booking meetings, I mean like scheduling meetings, rescheduling meetings. It might be like writing the proposal, right? These are things that you can outsource to, like, you know, the proposal. If you’re doing it new, you could probably get like, I just send the call recordings to a GPT bot that I’ve got and it gives me recommendations on like, oh, here’s the state of work. Here’s this for, you know, booking meetings and things, having I wouldn’t say an SDR, but like.
Dr. Jeremy Weisz: 36:14
Start getting all the pieces of the process off of your plate so that when you do hire someone, you have these in place for them just to be in their zone of genius.
Collin Stewart: 36:23
Exactly. Yeah. You’re building the organization chart underneath you. And so like, pick the things where you add the least amount of value and then hire for that role. But keep your hands on all the rolls and don’t try and hire like four rolls up from what you’re doing now, right? Like, it’s really tempting to go and try and hire that like sales leader who’s been there done that before. But if you don’t need like if you don’t need a sales leader.
Dr. Jeremy Weisz: 36:53
I’ve heard varying opinions on this, so I’d love to hear yours because some people are like, yeah, just hire a sales manager and then they’ll help hire the sales people or you. I’ve heard there’s a million different things flying around.
Collin Stewart: 37:04
If you need a hammer, don’t pick up your screwdriver. Right. Like your hammer is something to beat nails with. Occasionally I hit them with a screwdriver or something to turn screws. You know, a sales manager, a sales leader is going to build a sales team if you don’t want to double click and then suddenly build the sales team, don’t hire that person. And I would argue that you probably don’t want to hire that person until you have proven it, that you can one, sell. Two you’ve got the process three that you’ve already hired and built the team, the systems, the infrastructure. Because there’s just so much risk that goes into creating a new department, especially sales is arguably the most important.
Once you’ve got the product and all that up, if you can’t take it to market, there’s no revenue, there’s no company. And so I hear a lot of founders say, I want to get it off my plate. And I’m like, why? This is the single most important thing to your company. And you’re the best at this in your company. I don’t care if you’re not a good salesperson, you’re going to be the best salesperson your company has ever seen. It doesn’t take that much. So that’s my advice is prove it, then scale it. Pick the least valuable part of your job kind of every week, every month, and like higher up and then only hire a sales leader. If you’ve already proven that you can make a sales motion work and you know precisely what you want. Because even if you’re hiring a sales leader, there are ten different types of sales leaders that you might want, and you really want to match that profile to the profile of what you’re going to be selling. Of your sales motion. And you can’t know that until you’ve done it.
Dr. Jeremy Weisz: 38:41
So can we have about three minutes? I have three questions that probably would take an hour, but we’ll condense it. We’ll see if we can. We can cover it. I want to hear about Uber because it’s very instructive in your book, obviously. Terrifying Art of Finding Customers. Also, I want to hear about your shelf of honor and what books are in there, and then maybe some favorite podcast episodes. So maybe start with Uber first, and then we’ll rapid fire, maybe through the shelf of honor so people can get inside your brain and what books you love and podcast episodes.
Collin Stewart: 39:12
Cool. When Uber launched Uber Eats, I’m excited to be able to tell the story on a podcast. I just got approval from Uber’s legal team or we got I guess it was a while ago now, but we got approval to tell the story in the book. I’ve been wanting to tell the story and alluding to it for a long time, but when they launched Uber Eats, they tapped us to book meetings for their sales team, with every restaurant in the top 50 cities in the top 25 restaurants. We did that for a couple of months. We booked it just it was like 300 and something meetings a month. And then they brought in. They literally hired 100 Bdrs to replace us. So it was a really interesting four months. And what that taught me was product market fit is a multiplier of your go to market because Uber got like, I don’t know, six x better sales efficiency than any client we’d ever seen.
The shelf of honor is the book shelf that’s closest to me. It’s got all the books that I reference on a regular basis. I’ve got Dan Olsen’s Lean Product Playbook. I’ve got Good Strategy, Bad Strategy in there. That’s the one that’s got probably the most notes on pages, obviously. Four Steps to the Epiphany. The Mom Test, The Messy Middle. Obviously awesome. Stop Asking Questions by Andrew Warner is an underrated, fantastic book if you’re in sales or running a podcast. It is just one of my favorite books and I didn’t find it until only recently.
Dr. Jeremy Weisz: 40:38
He came on. There is an episode with Andrew talking about some of the key points of the book, so people could check that out. It is a great book for sure. The Mom Test that I don’t think I’ve listened to that one.
Collin Stewart: 40:51
Yeah, it’s a good one, especially if you’re doing customer development and asking questions. My favorite episodes I’ll give you two. I don’t know the episode numbers, but my first one with Jamie Buss from Zendesk, she taught me how she is. She was forecasting Zendesk’s revenue within 1% at the time. They were doing a half billion in revenue a year. And so we got into like medic and sales stages. It was really geeky sales podcast. It was early days, so the quality from my side is terrible, but from Jamie, she’s like, she was one of my favorite guests ever. And then the last one would probably be most recently, I think it just came out with Mase from Fixify. And we’ve transitioned the podcast from like only sales development to doing founder stories and revenue kind of going deep on revenue tactics. So Mase from Fixify and Jamie Buss.
Dr. Jeremy Weisz: 41:44
Michael Feaster or Michelle Feaster.
Collin Stewart: 41:47
Oh Michel Feaster that one was incredible too. Yeah.
Dr. Jeremy Weisz: 41:50
Yeah. That was a good one for sure. First of all, Collin, thank you everyone. Check out PredictableRevenue.com and of course as we mentioned get the book. I’m going to listen to an audible Terrifying Art of Finding Customers. Thank you so much Collin. Appreciate it.
Collin Stewart: 42:09
Thanks for having me on, Jeremy. It’s good to see you again.
