No Broke Months For Salespeople - This One Mistake Can Kill Your Startup Before It Grows | Collin Stewart

Episode Date: May 16, 2026

What you’ll learn in this episode: Why being “60% right and 40% wrong” can still destroy a business The biggest mistake founders make during customer development Why product-market fit exists on a spectrum—not as a yes/no answer The customer development funnel that creates referrals naturally How to know when your product is ready to scale The danger of building based on your own assumptions instead of customer pain Why entrepreneurs struggle to balance confidence with humility The exact questions to ask customers before investing in growth How Uber Eats generated 33x stronger sales results than average clients Why slowing down can actually help you grow faster About Collin Stewart Founder, CEO, podcast host & failed musician How can he help you? Bootstrapped PR to millions in revenue Built a revenue team to 11 Grew 3 companies from $0–$1M as the only sales hire Hosts a podcast with 120+ episodes Nailed product-market fit but whiffed on building it (and learned a tonne from it) Connect with Collin Stewart: Predictable Revenue Founder's Edition The Terrifying Art Collin Stewart LinkedIn Predictable Revenue Podcast 👉 Don’t miss out! Sign up here:No Broke Months Community Shadow Hour Updates to get the latest updates and reminders for our Shadow Hour sessions. Stay informed, stay ahead! To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook Page: https://www.facebook.com/NoBrokeMonths/Facebook: Dan RochonLinkedIn: Dan RochonTeach to Sell Preorder: Teach to Sell: Why Top Performers Never Sell – And What They Do Instead

You're listening to No Broke Months for Salespeople Podcast. Welcome to the No Broke Months podcast. My name is Dan Roshan. Today I'm joined with Colin Stewart, or Colin Stewart rather joins me. No, that's still wrong. Colin Stewart is my guest. Damn it, I got it that time. Colin is the author of the terrifying art of finding customers.

You can check out terrifyingart.com to learn more about that. We're going to talk about how to avoid wasting months building the wrong. wrong things. So if you have ever wasted months in the past by building something that didn't work out, today shows the one for you. Colin, hello, sir. Dan, thanks for having me on. Great intro. I thought that was the worst intro I've ever done in my life. And I think that it's going to end up being like the best, the greatest. Yeah, it's authentic, you know. I've bought my fair share of intros. So yeah, you're doing it live. I respect that. Colin, thank you for joining me today. So before we jump into how to avoid

wasting months building the wrong thing. I'd love to hear a little bit about your, a little bit about your background, a little bit about your story. What would you like to share with us? For sure. I mean, the short version is, I spent 10 years as a salesperson as my first kind of career or trade, kind of. And then I was always the geeky sales guy. And so I was always the one who got pulled into the CRM project. So spent 10 years selling, thought I was an expert in CRM, wanted to start my own company, started a CRM company. I thought it was an expert. And so I just went and I built my ideas. And I read all the books,

you know, the mom test, Steve Blanks, all the Steve Blank stuff, the Lean Startup. And so I was like, I got to do customer development. And so I went and I had my sketch

of what I was going to do. It's like, hey, I'm going to build this. What do you think? And they're like, awesome. I was like, cool.

I'm a genius. Everybody thinks this is great. I'm having all of these great conversations. And then my team went and built it. And I came back to those same people. And I was like, hey, we built that thing.

Do you want to? And they were like, cool. I'm like, It's like, well, how come? They're like, oh, we would never pay for something like that because X, Y, Z. And I was like, oh, I really should have asked those questions ahead of time. And so when I finally pulled my head out of my butt, I realized that I was doing customer

development wrong. And I was building my ideas and not solving problems that like my customers who are my prospects were asking for. But the hard part was I was 60% correct and 40% wrong. And like the insight that I have. was old enough to have been a salesperson that had CRM installed on their laptop and had to go through the like get the SQL set up and blah, blah, blah, blah, blah. And I remember the transition from that, which was my piece of software to using Salesforce,

which was my boss's piece of software. And what we lost as salespeople was that piece of software is no longer mine. It is no longer my personal productivity tool. It is my boss's tool that I have to fill in so he can have his dashboards, which is, I think, a totally valid use case for CRM. felt some loss. And so that was the insight that I had is that CRM isn't a sales productivity tool anymore. So I was going to build a sales productivity focused CRM. That turned out to be the wrong hypothesis. And when I went and interviewed customers and I listened for folks that were

struggling with that, I found an even bigger opportunity. And when we built that, we went zero to a million an ARR in three months. And what was that bigger opportunity? It was taking the insight. And we found a very specific use case within the sales realm, which, at the time was sales development reps, and they were struggling to get, like, send cold emails in Salesforce because it was 17 clicks to keep everything up to date. And like my, the company I had started, my early co-founder was Aaron Ross. He was the author of predictable revenue. That book came out of Salesforce.

I think he was employee 150 or something like that. And when the way Salesforce did it was every email you sent, you had to create a task and you had to name it and like email. And then the next one was follow up one and follow up two and then call, call one, call two. It's not exactly that, but is directionally correct. And all the reporting was based on those. And so everybody was following that system, which meant as an SDR, it was a ton of manual labor in Salesforce. And this is click labor.

So it's not like. What's SDR? What's SDR for? Oh, sales development rep. So cold caller, cold emailer. Yeah, got you. Person who's going to interrupt. All right.

So it was a pain in the ass. In other words. Exactly. Huge. And then you helped the stream mine at? Yeah. Yeah. Yeah.

We built a tool that automated all of that away and made it easier for them. And did you sell that product to Salesforce? Is it still in existence? Like, what happened next? Yeah, that's the fun part. So we spent about a year bootstrapping on that product. And we were running a cold email agency in order to build it out and build out the tool. And then when we were in that process, my CTO came to me and said, hey, listen, if we're going to make this, we really should, instead of forking the code of our old crappy CRM, we should start fresh.

and build something purpose built for this opportunity. And I said, no. And he said, well, there's going to be tradeoffs. And it's going to, like, one, it's going to take longer or two, there's going to be risk that it won't work or that it won't work as well. And I was like, ah, no, that's fine. I read Joel Spolsky. He said, you're never supposed to rebuild, blah, blah, blah, blah, blah.

So I made this terrible decision early days. We basically said yes to everybody who wanted it. Like, for three months, we were the hot startup. Like, everybody knew who we were. Everybody knew who I was. It was my 15 minutes of fame. and I let that go to my head and thinking, oh, my God, I'm a genius and this growth is going to go on forever. But what we, the mistake we made was one, not letting Preston our CTO build something that was going to scale.

And then two, taking on so many customers so quickly and just assuming that we would figure it out when the product wasn't built. And so in hindsight, what I would do the next time and what I am doing this next time is taking on a few customers at a time, making sure they're extremely happy. and then asking them, hey, what do I need to build to get you to refer me to three other customers? Because in the first place, everybody was so excited that this thing just existed, that I would close a customer. And after they signed the contract, they would refer me to three other friends before they'd even use the product. And so that's how we had this such crazy growth. Like, I was spending eight hours a day on calls.

We had some, like, newsletter and we had some brand awareness. But eight hours of back-to-back calls and they were all closed, like, not I shouldn't say all-closing calls, but I had a like 60, 80% closing ratio. It was insane. And because nobody had like, we were replacing clicking around 20 times per email that you wanted to send in Salesforce. So it was really easy. The problem was the product wasn't as built as it needed to be.

And so customers would come. They would love the demo. They would love the initial vision. And then they'd come to use the product. And there were just so many rough edges that they're like, hey, man, this thing isn't ready for prime time yet. What did you learn from that experience? I mean, the contrast between it was almost the same vision with the CRM company as with the one that exploded.

And so one was like, okay, I was correct and wrong at the same time. And that was a really hard idea to get my head around that like 60% right, 40% wrong was like really challenging. The second piece was that I had done customer development incorrectly the first time by saying, hey, look at this thing that I'm building. Isn't that great? And they'll go, yeah. That was silly to put it politely. And then the third thing was the mistake I made in terms of not allowing or not having something

there's purpose built for the product opportunity that we were creating. And like just listening to the smart people around me. I think that that is probably an overarching theme in my early years as an entrepreneur of just like, I had a lot of smart people around me that said, hey, that thing, see that oven? That element on the oven. It's really hot. I highly recommend not touching it. And I was like, ah, I'm invincible.

I'll touch it anyway. So yeah, I did that a whole much. It's interesting, Colin, because that's what you just described is a blessing and a curse of the entrepreneur, right? You've got to have the faith in yourself and your ability. Yeah. You know, you have to believe in yourself. And then, but the other side of that is when you listen to other smart people, right? And consider their points of view, then, you know, it's sort of that balancing that, like, certainty, right?

Like, because an entrepreneur is not going to be an entrepreneur if you're not certain, right? But then that same certainty can sort of screw you up because now you're 60% right and 40% wrong. And you're like, oh, goodness. Like, you know, and that's a balance. I don't know really. What are your thoughts on that? And like, how do you position yourself so you can still remain certain as an entrepreneur, still remain confident as an entrepreneur? These are all the qualities an entrepreneur has yet also be humble and let your ego, you know, set aside and listen to other smart people.

What are your thoughts on that? Yeah. I think the best advice, and I shouldn't say advice, but I think I picked up something from a parenting book that kind of helped me understand the complexity that we're talking about. And it was, Dr. Becky, I think it was good inside was the book. And her idea was two things can be true. And I was like, I read that. I was like, oh, my God, this is, this applies more to just parenting.

But like, the idea that I could be right about the insight around sales, CRM is not a sales productivity tool, but I could also be wrong about this particular thing is the way to solve it. And like balancing that, because candidly, if I was more pragmatic and I came into this more open-eyed, if I was smarter, I probably wouldn't have started a company. I certainly wouldn't have started a CRM company. But that failure got me here. And like the characteristics and the traits that like got me into all this, all these problems are also the ones that carried me up the roller coaster, you know, the other direction. And so 14 years

in, I'm still doing the thing. I'm still writing my own paychecks. And like, I appreciate that. And so, yeah, I say, I say, so I'm a single guy. And I went on a date not too long ago. And I told the women, I've been unemployed for 20 years. No, not a good, no. I mean, we're also unemployable, you know, like. I am. And that. And Man, you just took it. I am unemployable, right? I get it, man. I get it. I am unemployable. I want to, it's funny. Colin, so let's talk about the how to avoid, or I'm sorry, let's talk about the terrifying art of finding customers, which is a book that you authored. So tell us like what caused you to write that book. What's the theme of the book? What can we take from that book to, you know, what problem does it solve? So I started writing the book because we had this. So the short. version of the story of like got zero to a million with carb the software product and then it kind of plateaued at a million and we'd bootstrapped we'd built a services business around it and that

business made up to 85 people and five million of revenue and like in theory i should have been happy having a five million dollar business and 85 people and a management layer and this and that like i should have been satisfied or at least happy and i was the most miserable i'd ever been and i think a big piece of that was I felt like I missed out on the opportunity, on the product opportunity, and I wanted to get back to that. And then the other piece was I felt like I was stuck running the services business, and I didn't want to get stuck running this business for the rest of my life because I wanted an opportunity to say, to prove that like, hey, I got this thing.

I caught lightning in a bottle briefly, but then I screwed it up and I dropped the bottle. I wanted to prove that that wasn't a fluke. And so my board was pushing me to write because the original book was predictable revenue and that brought a bunch of customers. they were pushing me to write predictable revenue too. And so I started and I was hating it. And I imagine you're an entrepreneur like me. If I don't want to do something,

I am the absolute best in the world at not doing that thing. Like I can make it look like I am. And I'm sitting there writing things, but my brain's like, mm-mm, I'm not involved. And like my hands are basically writing the book and that's it. It's up to my wrist level of effort. And then everything else is disconnected. And I spent a couple months writing,

like that and I hated it. And I was like, you know what, I'm not going to listen to them. I'm going to write a book, but I'm not going to write that book. And everybody else told me, you know, don't write this book. But I was like, I don't care. I'm going to write the book that I care about writing. And through the sales agency, I'd had thousands of conversations with founders about kind of on the same journey as I was in saying like, hey, I don't think you have product market fit. And nobody wants to hear they don't have product market fit. It basically means, you know, they're like, well, I have customers. I have a product. I have product market fit. And I think the words I was looking for was, it's not that you don't have product market fit.

It's that your product market fit could be stronger. It's that you don't have strong enough product market fit to pay back the investment that you're going to make with me. And so I was trying to warn them like, hey, I don't think this is going to be a profitable investment for you. And I was using the words, you don't have product market fit. And so they totally ignored me. And I think the connection I was trying to, I wanted to draw with the book, the thing that I really cared about was the idea that product market fit is not binary. It exists on a curve or on a spectrum. from, you know, zero to one, which is like you've got some customers and you've got a product

in market to like Uber when they launched Uber Eats. And every restaurant in the world wanted to get on Uber Eats. Now, the sentiment has probably changed now. But for the first couple of months, they were like the hotness. And so like product market fit is a strength or exists on a spectrum. And it is a multiplier of your go-to-market efforts. Meaning when Uber, and this is a real example from the book, well, from my experience, when Uber Lunch, Uber Eats, they tapped me and my team to book the

meetings for their 100 sales people that were going out into market. And in 30 days, we booked 327 meetings. And we sent a thousand emails to book 327 meetings. Okay. It was like 12 times better than our typical metrics for. Yeah, I was going to say, that's an amazing, like, that's probably even more than 12 times. But that's amazing. Our best customer for like meeting production. I think it was top toll. And it was like the talent agency that had like top one percent of engineer outsource engineer talent. And you could hire them directly through the platform.

And they were they were getting like 60 meetings a month. And I was like, that's an insane number. We launched with Uber. It was 327 and it broke everything. We had to like we had to shuffle things around. It took us. Yeah.

It just it pointed me to the fact that like we had one rep on it. And I was like, did Krista magically get 33 times better from December to January, or is it something specific to the client that she has? And I mean, Krista was amazing. She was our best person, hands down. But there's no reality where she used magically 33x better from one month to the next. And so how did we reconcile that?

And to me, the learning was the insight was, okay, well, if Krista didn't magically get better, then Uber is getting 33 times more value from our same service that we're providing to everybody else for the same price. And so that is the brand. It is the product, but it's how the product fit into the market. And so strength of product market fit or the fact that they had such strong product market fit acted as a multiplier of their go-to-market efforts. So they got 33x better than everybody else because they had such strong product market fit. And so that was the core insight behind the book and how I wanted to, the message and the idea that I wanted to get across is like the one of the best takeaways you could take you could get from the book is how

to time your go-to-market investment, how to know when you're ready to invest and go to market. Because I think a lot of founders that read sales books, you kind of read the mom test over here and you find an opportunity. Maybe you read the lean startup and you're like, or you read any of Steve Blanks stuff. And you're like, okay, I need to get out of the building and talk to people. And you think that customer development is something that happens over here and sales is something that happens over here. But the idea I show in the book is that they're not two separate processes. They are one and the same. And you need to start with customer development. And then as a dirty salesperson, you need to book the next call on the call. And so you start by asking them for

advice, hey, you know, if I could solve any problem for you, what would it be? And then at the end of that call, you say, hey, when I, when I decide to, if I decide to build this, you know, would you be up for giving me some feedback? And then you get on that call and you say, hey, I built it. Feedback. Great. When we decide to build, like, if, if you decide to build, like, if, if you're, you know, we decide to build a full version or any of these features, would you be able to give me any feedback on these features? Great. Then you book that call. Then you show up to that call and say, hey, what do I need? What features do I need to build in order to get you to use this full time? Then you go build those features and you book the next call. And then they're using it full time.

You say, hey, what do I need to build to get you to give me some money for this? And then once they're using it, giving you money. Yes, the last question, which is, what features do I need to build to get you to refer me to three friends? And then that's how you get the referral funnel going. That's phenomenal. You're not spending money on go-to-market. You're just investing time, learning from your prospective customers, and then working them along this funnel until they turn into referrals.

And the best part of this is you're not, you don't have to, like, this is something the founder can drive. You don't have to turn this into, let's go hire an SDR, let's go hire AEs, let's go invest a crazy amount of money. You can look at this customer development funnel as a funnel, and you can look at the efficiency of that funnel. You can look at the number of people you put in. You can look at the conversion rate from stage to stage.

And you can look at the velocity. How many people to go into this funnel? How likely are they to go from one stage to the next? And then how quickly do they do it? And the higher the conversion rate and the faster they move through is a very strong indicator of strength of product market fit. And so if you're following this process and nobody's moving forward, that's an indication that you probably shouldn't keep investing in this or you need to go back

because you're 60% right, 40% wrong. And so that was the whole idea that I was trying to do. to get out in the book. And that's the thing that I hope people take away is you need to strengthen your product market fit before you invest in go to market. And the customer development funnel is the way how. If you're a real estate agent averaging four to 12 closings a year, and you want to know what it looks like to join a team that sets your appointments, handles all your administrative task, and gives you daily live training. Visit www. W.nobrook months.com for slash join us.

Nobrook months.com for slash join us. We review every application. What if so many founders end up building the wrong thing? Or spending their time on the wrong activities? I don't speak for everybody, but I can't speak for myself. And that I thought I knew the answers. And I thought I was doing it correctly. And I thought I was an expert.

I am embarrassed to admit this. but I once said the words, I'm the Steve Jobs of CRM out loud. And it wasn't in jest. And like, that guy, that version of me is an idiot. And like, I'm glad he existed because I got here. But looking back, I'm like, those are stupid, arrogant words said by somebody who doesn't know what they're doing.

And so I'm not going to say that all founders are dumb and arrogant because they're building their own ideas. I'm saying that I specifically was. but I've seen different versions of that through my career. Well, I'm curious, Colin. Do you think Steve Jobs was arrogant? I think it's pretty well documented that he was. I'm just saying.

I mean, he's one of the goats. Like, of course he would be. Yeah. I mean, I'm just, right? So that arrogance, again, you know, you're using it as a negative context. And perhaps it is. But I mean, goodness, you're literally using somebody who would be synonymous. with arrogant yet you know he has an urge he definitely had an earned arrogance right yes but he had the

arrogance before he earned it I may you know it probably I'm not sure I've read his biography and it's hard to say but yeah I don't know his early life but you know um we only know him through reading books um of course but yeah I mean I certainly hadn't earned it at that stage and I think I was making the mistake of overweating putting too much empathy and emphasis, too much importance on my thoughts, my ideas, and not enough emphasis on what the market actually wanted. And I think that is the number one thing is building the thing that you want to build or the thing that you think is the right solution instead of going and asking the market, what is it that you want, need, what is the pain that you'll pay for? Like my two favorite

questions, I stole from Dan Olson, which is like, I asked the magic one question, if I could solve any problem for you, what would it be? And then when they answer, say, cool, how important is that to you on a scale of 1 to 10. And then I shut up and listen. And then I say, great. Okay, so you said it's a 10 out of 10 importance. On a scale of 1 to 10, how satisfied are you with how you're currently solving that? And this is how you calculate the opportunity score for should I, should I follow up on this?

Because when you ask the magic wand question, the thing that might be at top of their mind is like, I can't update my Excel because my company's IT policy won't blah, blah, blah, blah, blah. And like, sure, that's a big pain, but, like, there's, it's not tied to any impact, right? And so you need to ask importance, satisfaction. And then once you have that impact, if I, if you were to solve this, how would it impact your personally, you personally, you professionally, your company, your OKRs, your bonus? And like, is it going to increase money, increase revenue, decrease cost or decrease risk, right? Like, those are the three kind of values that you need to be able to tie to.

and it's got to be a short walk to get to one of those. What are the early warning signs that you may be going down the wrong path? I think if customers, if you ask for that next step in the customer development funnel and they're not open to taking that call, it's probably a sign that it might be a sign that things aren't going the way you want. If at the end of calls, if you're asking for referrals, hey, do you know anybody else I could interview for this? And they're like, no, I literally know nobody else.

And you ask everybody else or everybody in your network. and nobody else knows anybody or is willing to make those intros to folks that have the same pain might not be that strong. That's brilliant. Would you like to leave our audience with a word of advice? And I'm going to ask you specifically to consider the biggest mistake you've ever made in business. And what could you do to avoid it? And what could somebody else do to avoid the same mistake?

Yeah. I mean, I feel like I'm coming back to, you know, playing the same song over and over. again, but I do think the biggest own goal I scored was the, yeah, like the missed opportunity around how we planned out our market opportunity for car, or how we planned out the launch of carb and not having something that was not listening to our customers, not, not building something to solve their needs. Like even with carb, I still did a version of like, I'm building my vision and not listening to customers because I thought, oh, I've got this nailed. In sales calls eight hours a day. I've got so much. We have so much revenue that's coming in. I assume that we'd

keep going forever. What I wish I would have done and what I will do next time is go slower, talk to folks, find their pains, even after we found the problem, stay in close contact with them and continue asking these questions until we built 100% of it, until they're saying, yeah, we don't need any other features. And now I'm going to refer you to three other friends. I love it. How can somebody get in touch with you? Can find me on LinkedIn, Colin Stewart, email me at predictablerevenue.com. You can follow me on the newsletter at foundersedition.com. And terrifyingart.com as well.

I recommend that you go and find the terrifying art of finding customers to learn more about how you can avoid wasting months building a wrong thing. Colin, thank you so much for joining us today. Audience, thank you as well. Until next time, have the best of your life. Be grateful to make your choices to go help somebody. God bless you. I love you today.

I'm on a mission to help one million people to sell without selling by teaching them how to think through teach to sell. Thank you for being a part of that mission. And to be able to spread the word, I'm going to have a very simple request of you. Give me a five-star review because that's going to help us to be able to reach more salespeople, more entrepreneurs, more business people who are looking for consistent, predictable income so that they can start building their faith in their self today. So just take a second. Five-star review, cost you nothing. Thanks so much. Love you to death.