Collin Stewart joins this episode to share his journey from humble beginnings as a “geeky sales guy” to becoming a sought-after expert in achieving product-market fit. With a career spanning multiple startups and countless lessons learned, Collin’s insights are a must-hear for anyone building a business from the ground up. Through candid stories and hard-won wisdom, Collin reveals the mistakes many entrepreneurs make when trying to scale too soon, as well as the key strategies for finding product-market fit. He explains why understanding your customers’ pain points is non-negotiable and how early-stage founders can use customer development to turn insights into revenue. Collin doesn’t just talk theory—he provides a clear, actionable framework to help entrepreneurs identify real market opportunities, validate their products, and scale sustainably. His emphasis on listening to the market and aligning growth with timing offers a refreshing perspective for founders navigating the challenges of early-stage business. Whether you’re an entrepreneur searching for direction or a founder ready to scale smartly, this episode is packed with value. Collin’s practical advice, combined with his no-nonsense delivery, will leave you inspired to rethink your approach to product-market fit. Key Takeaways: * Why product-market fit isn’t binary and how to measure it effectively. * The dangers of premature scaling and how to avoid them. * A step-by-step guide to using customer development as a foundation for growth. * Real-life lessons on creating products the market can’t live without. Head over to podcast.iamcharlesschwartz.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode. KEY POINTS: 2:01 - Common Mistakes: Collin highlights frequent entrepreneurial pitfalls, including ignoring market signals, rushing to scale, and failing to truly understand customer needs. 9:32 - Premature Scaling Risks: The dangers of scaling too early are laid bare as Collin explains why investing in sales teams or development too soon can drain resources without delivering results. 12:11 - Understanding Product-Market Fit: Collin breaks down product-market fit as a spectrum, where success depends on identifying market needs and crafting a solution that directly addresses them. 14:19 - Market Need Importance: Collin emphasizes that strong market demand—not personal passion—is the foundation for sustainable business success. 19:00 - Customer Development Process: A step-by-step framework for engaging with customers, uncovering their pain points, and refining your product to meet market demands. 35:00 - Outbound Sales Timing: Collin discusses the importance of timing outbound efforts to align with market readiness and long-term sales goals. 37:26 - Long-Term Thinking: Founders are urged to adopt a mindset of patience, focusing on sustainable growth and avoiding the trap of short-term gratification.
Chapter 2: What are common mistakes entrepreneurs make?
Chapter 3: How can premature scaling be avoided?
We basically used the agency to bootstrap a couple of SaaS companies into existence and made some huge mistakes and learned a lot along the way. But I'd say finding that first market opportunity and then figuring out how to transition that into your first customers.
You mentioned that there's a bunch of mistakes along the way, which I think all of us do. So before we get into the strategies on how to do it right, let's talk about some of the ways that people just do it wrong or some of the mistakes you've made along the way.
Well, initially, like I came from sales. And when I walked into the accelerator incubator co-working space where I started, it's called Launch Academy. I think it was the only person that came from sales. Like everybody else was product and engineering. And I was the obnoxious guy who was always on the phone talking to people. And I remember engineers being like, why is this guy? Can I swear?
Yeah, absolutely. Okay. What the fuck? Why is this guy always talking to somebody? Like, doesn't he actually do any work? And that was kind of the perception. And I came to it because I had come from sales and I was trying to figure out how to do customer development. But I had spent 10 years, 12 years in sales as the geeky sales guy.
And so when you're the geeky sales guy and you're the youngest on the team, you naturally get pulled into every CRM project. And I got into sales because I was in marketing, and I found a way to write a copy and paste a macro from Stack Overflow and basically automate my job.
And then I was sitting there, and I was playing solitaire, and I almost got fired because I was playing solitaire because it was the only thing on my computer that would run, and I couldn't do anything else. And so after almost getting fired, the sales guy across the hall was like, hey, I got some cold calling. Here's a list. Come join me.
And so he sat me down and kind of gave me the spiel, and I started cold calling. And so that was my entry point into sales.
And as you were going through that and you kind of entered into sales from playing solitaire, and I love that you started as the geeky sales guy because I started as the geeky IT guy that ended up being able to bridge the gap between the business owners and tech because tech couldn't talk human and human couldn't talk tech.
And I was like, all right, I got to find a way to get these guys to talk to each other. So it's a similar path. But in this situation, you talk about a bunch of the failures that people do when they're trying to get it and do that initial launch. What are some of the failures or classic mistakes people do?
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Chapter 4: What is the customer development process?
Chapter 5: Why is understanding market needs crucial?
And then I was sitting there, and I was playing solitaire, and I almost got fired because I was playing solitaire because it was the only thing on my computer that would run, and I couldn't do anything else. And so after almost getting fired, the sales guy across the hall was like, hey, I got some cold calling. Here's a list. Come join me.
And so he sat me down and kind of gave me the spiel, and I started cold calling. And so that was my entry point into sales.
And as you were going through that and you kind of entered into sales from playing solitaire, and I love that you started as the geeky sales guy because I started as the geeky IT guy that ended up being able to bridge the gap between the business owners and tech because tech couldn't talk human and human couldn't talk tech.
And I was like, all right, I got to find a way to get these guys to talk to each other. So it's a similar path. But in this situation, you talk about a bunch of the failures that people do when they're trying to get it and do that initial launch. What are some of the failures or classic mistakes people do?
Well, I think because I had spent so long in sales and I'd been involved in so many CRM projects. Not I think, I know. I considered myself an expert. I'm an expert in CRM. I've set up a bunch. I've been using Salesforce since 2005, like early, early, early Salesforce. So I had a very... large opinion of myself.
And so when it came, when I read, you know, all the books on customer development and get out of the building and interviewing people, I think I took the term customer validation a little bit too literally. I had sketched out my idea and I went and did, I put the effort in and I interviewed 50 people and went, look at my idea. Isn't it great? Not quite in those words, but that was the effect.
And I've seen this in a lot of other entrepreneurs where I wasn't open-minded enough to hear people actually saying, we don't want another CRM. Your idea is interesting. You have a valid insight, but we don't want that insight packaged as a CRM. We want it. as part of Salesforce or working along Salesforce.
And I couldn't, I couldn't, it was like a belief that I had, you know, like some people have these beliefs that they just are not willing to change. Yes. And this was one of them. It was like, no, no, no. I'm going to, I believe that I'm smarter than everybody. I'm this deep jobs, a CRM, and I am going to, you know, break this thing wide open.
I'm going to take on Salesforce and obviously it didn't work. Um, I eventually, I had a mentor sit me down and I'm Canadian. And he said about the meanest thing you could say as another Canadian, which is, I can't wait till you're working on something where you have a chance of being successful.
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