Forecasts are overrated—great founders build one step at a time. | PMF Observations

I break down my top insights from recent conversations with four founders who won in unconventional ways. You’ll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan’s startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into a $25M cash cow by solving one overlooked customer pain point. Plus, and how Cleerly used a 17 day-from- bankruptcy moment as its turning point. 

Why You Should Listen

• How to turn LinkedIn into your best sales channel without going viral

• Why a 95% downround doesn’t mean your startup is over

• How near-failure experiences can lead to breakthrough growth

• The power of uncovering overlooked customer problems to drive massive profits

• Why constraints and limited resources can become your biggest advantage

Keywords

product market fit, startup growth, LinkedIn lead generation, fundraising, downround, bootstrapping, founder lessons, pivoting, scaling startups, entrepreneurship

00:00:00 Intro

00:01:01 How Stacker Leveraged LinkedIn for Explosive Growth

00:04:43 Clutch’s Wild Ride from Unicorn to Nearly Bankrupt and Back

00:07:38 Navigating Market Cycles as a Founder

00:08:32 Retention.com’s Pivot from Stagnation to Massive Profits

00:13:33 Cleerly’s Near-Death Moment with Only 17 Days of Runway

00:16:21 Why Constraints Are a Secret Weapon

Chapters

• 0:00 Intro
• 1:01 How Stacker Leveraged LinkedIn for Explosive Growth
• 4:43 Clutch’s Wild Ride from Unicorn to Nearly Bankrupt and Back
• 7:38 Navigating Market Cycles as a Founder
• 8:32 Retention.com’s Pivot from Stagnation to Massive Profits
• 13:33 Cleerly’s Near-Death Moment with Only 17 Days of Runway
• 16:21 Why Constraints Are a Secret Weapon

Transcript

Pablo Srugo (00:00:00):
So I used to do these kind of like shorter-form episodes, and we just we've just been cranking out interviews over the last few months, maybe last few quarters even. So I really haven't done any of these kinds of short-form episodes in a long time. So we're starting that back up. We're going to start that back up because I think we're producing so much content. For me, I'm just talking, so many incredible founders, founders that have absolutely crushed it and are now late-stage, founders that are crushing it right now in the early stages and growing exceptionally fast, and even founders who failed. And frankly, there's so much to learn from failures. And so trying to put all that together. So the plan now is like, I'm going to go every four or so episodes and just take from each episode what I think is the most interesting, most insightful, but like maybe my number one observation from that episode and basically put all those observations in one place.

Previous Guests (00:00:49):
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit. 

Pablo Srugo (00:01:01):
Do you think the product market fit show has product market fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders, and it lets us get better guests. Thank you. 

So, the number one thing, like from talking to Stacker, I mean, Noah, he launched a product two years ago, went from zero to $300K MRR, so call it four million ARR or so in just two years. And the number one thing that I think he did right is he just absolutely crushed it on LinkedIn. Like he just made LinkedIn such a huge lead magnet for him. And I think LinkedIn, I mean, I post a lot on LinkedIn, and it's getting like I talk to founders more and more lately that are trying to use LinkedIn to generate leads, and frankly, a lot of them suck at it. And a few of them, like Noah, like a few other people that I know, actually know what they're doing. 

Pablo Srugo (00:01:52):
I'll tell you two things about LinkedIn. And I think Noah would agree with this. Like the first thing is it's all about the hook. It’s all about the hook. You have to pay a lot of attention to the hook you put out there. I see a lot of people putting out posts that have actually interesting content. No one's going to click on them. No one's going to stop on them because your hook absolutely sucks. The second thing I'll say is actually the hardest part about LinkedIn isn't so much writing, it's coming up with interesting ideas to write about in the first place. And so you have to come up with a way of, as you go about in your day, finding a way to capture interesting moments, insights, thoughts that come to you because you're talking to other people in your company, to other founders, to your customers, and capturing them in one place. Because if you don't write consistently on LinkedIn, it's never going to work. So, you need a way to actually capture the ideas in a consistent way. And then some interesting things that Noah was doing specifically is, he had these things called like watering hole posts. He’s selling into PR departments at enterprises. So, he would make a post, for example, and feature some company and say, like, you know, this company is doing PR right. Here are the sort of things that they're doing. Here’s another company that's also doing things well. Who am I missing? And it's a watering hole because other people like you kind of get a conversation started. And of course, other people come in and start pitching how they're doing PR right. And when you're doing that and you're getting these conversations started online, you turn what would have been an otherwise cold lead into a warm lead because you've had that interaction. The other thing that he did smart on LinkedIn is he actually had a list of all of the accounts that he wanted to tackle. And he added all of the people that are like kind of important in those accounts, but he wouldn't message them directly and start spamming them. All that that was doing was just getting the connection going so that they were more likely to see his posts. And of course, when somebody sees your post and starts to agree with you with some of the things that you're saying over time, you're again. You're turning something that would have been a cold lead into a warm lead. It takes time, but it works. And the other thing that he had that was really important is like, you don't really need to go viral, right? Like if you want to post on X and you want to actually get seen, you need to really post like truly viral things on LinkedIn. It doesn't really work that way. And Noah was saying, like, some of his posts, most of his posts, frankly, they're getting a few thousand views, like, you know, 5,000, 10,000 views. Like, it's not a lot in the world of social media, but because it's getting views from the right people, it's still driving leads. And actually, funny enough, like, the post that I saw was one that actually did go viral. Had like 700,000 views. He’s like, that post got me, you know, on this podcast, like it got me all this attention. It actually gave me leads because it wasn't focused on my ICP. And so, you have to find this delicate balance between writing stuff that's interesting and having a solid hook, having like insights that come from your daily life, because that always is credible and specific, but also stuff that's actually interesting to whoever your ICP is. Otherwise, you're going to make a lot of noise. You’re going to get a lot of followers. You’re not going to get a lot of leads. 

Pablo Srugo (00:04:43):
Clutch has one of the most insane startup stories I've ever heard. They’re kind of this COVID darling, right? Deserved, darling. They’re a Carvana, but for Canada, right? Like they're a used car marketplace. They buy and sell used cars. And they were scaling exceptionally fast in that kind of 2021, early 2022 period. And they're raising a lot of money to do it. Investors are telling them, spend more money, grow even faster. And so, Dan is doing that. And then the world kind of changes overnight. Like if you remember late 2022, early 2023, the macro just completely shifted as interest rates went up. And all of a sudden, the money was just not easy to get. And all these money-losing models, especially asset-heavy ones like what Clutch was doing, went from exceptionally hot to toxic literally overnight. And he even had Dan even had this like $95 million round ready to go, and the investors pulled out last minute. He had to cut from 350 people to 87 employees. His valuation went from half a billion to 15 million. I actually don't think I've ever heard of a more insane down rub than that. I mean, you've seen it happen in public markets where some companies are down like 99%. Sonder was 2 billion. Now it's 20 million. But I haven't seen that in the private market really ever before this story. It’s crazy. But he managed to make it work. That’s the most insane progress. Typically, when that happens, the best you can hope for is some kind of an exit, you know, get people's money back. He’s now back to the old valuation. He just raised around at half a billion dollars again. His revenue is like three times higher than it was at peak before all this happened. And in the meantime, he didn't lose anybody from his leadership team. And I think, like the lesson, like the observation for me, there is Dan would never have wanted to do this. And I don't know that if the macro hadn't changed, he would have just kept going on his previous path. So, nobody chooses to do this. But my point and my observation is, more companies can go through a lot more than you might think. I mean, at the outset, if I said to you, a company brought its valuation down like 99%, brought its employees from 350 to 87, what are the odds that that company not just survives but actually thrives again? And the odds might not be great. And yet it is possible. It is doable. And I think what you have to look at and fundamentally what Dan and his team did is they looked at the core business, and they thought to themselves and not just like reasoned in theory but even in practice. And you look at it and you say, wait a second, do customers actually want my product? Do the unit economics make sense? Or can we make them make sense? Can we find a way over time to get to profitability? And the answers were yes, yes, and yes. And so as long as that makes sense, what's going to come and go is the investor interest, the investor appetite for whatever it is that you're doing. That just comes in waves. 

Pablo Srugo (00:07:38):
Web3 was hot. Now it's not that hot. Then it's hot again. Same thing's going to happen to AI. Same thing's going to happen to foundational models. It’s going to happen to asset-heavy and asset-light. It’s just. That is just the way investment works. Things get hot, then they get not hot, then they come back again. You, as a founder, have to find a way to navigate that, make the most of it when it's hot, and find a way to still make it through when it's not. But what truly matters is do customers want your product? Do the economics fundamentally make sense? If that stuff stays true, then you have a business regardless of the sort of terrible decisions that you might have to make before something. These are decisions that nobody wants to make. And yet as a founder, it's your job, and only you can make them. But even though you might have to go through these insanely hard moments, there's no rule that says that because you do mass layoffs. Because you do a mass down, round, you're not going to ultimately be successful. 

Pablo Srugo (00:08:32):
Retention.com is an interesting one. This is a company that got bootstrapped to $25 million. It’s doing $14 million in profit. The founder, Adam, hasn't raised any money. So, he's laughing. He’s like, Dude, I don't care if I grow this year. I don't care if I don't grow this year. Obviously, I want to grow. But he's like, dude, if I don't grow, I'm making $14 million net income. So, I don't care. And that was exceptionally compelling from a bootstrap founder perspective. But what I thought was most interesting as an observation was how he found this revenue stream. So, he started off, and he was, he had this, was kind of a competitor to like Mailchimp. Right. And there were a bunch of other competitors for effectively sending mass email, like email marketing platforms. And when Mailchimp came in, he said it just dominated the market. They just did product right. They did marketing right. And it was kind of crushing him. And he had like 3 million in ARR, but he was just flatline. And at $3 million, I mean, you can flatline at $25 million with some solid margins. At $3 million, if you flatline, there's just not enough there. So, he's trying to figure out kind of what to do. And he goes to this conference, and he meets someone, and he has a conversation. And the person says to him, like, you know, you’re kind of just doing what everybody else is doing. Like there's all these competitors that are all building these email marketing platforms. You’re not the market leader. Find something that customers want, but nobody else is actually solving. And, you know, it seems simple at the outset, but for whatever reason, that just kind of set him back and maybe made him think. And he started just exploring things a little bit more instead of saying, OK, how do we keep building this kind of email marketing platform? What is there in this email marketing world that people desperately need and yet don't have? And with that kind of mindset of looking for those things, and often I'll say as an aside, when you kind of have a higher idea of what you're looking for, all of a sudden, these kinds of clues start coming in from the outside. It’s funny how things work, and I don't believe in karma or anything like that. I think that there's something to, when you're looking for something, you're just more likely to find it. And in his case, what he ended up discovering is that there was a way to find out who is on your website, even if they don't give you an email. If you think about the most important thing, frankly, if you're building an email marketing campaign, is you need a list of emails. So therefore, you need email capture. So typically, you go to a website, and it's like, oh, put in your email, subscribe, whatever. That’s great. And obviously everybody is doing that. But what about everybody that comes to your site that doesn't leave an email? Is there any way you could find a way to reach them? And then there's spam and all those other things, but obviously from a business perspective, if you could somehow get those emails, it would be exceptionally valuable, and he finds a technology that allows you to do that obviously for some subset of emails, and don't ask me exactly how it works because I don't know, and frankly, for this observation, I don't really care. Because my point is beyond this. But he ends up finding a way to do that. And that's the business. So, he kind of gives up the entire platform and just says, listen, I'm just going to get you more emails. I’m going to get you people that went to your website that obviously showed some indication of interest. For whatever reason, they didn't leave an email. And yet I can, through cookies and a bunch of different things that they're doing, figure out who some of those people are. That’s interesting as an observation because it's kind of this idea, this mantra, if you want to call it that, like you have to be in the market to win the market, right? On the one hand, he had to be in the email marketing world for him to stumble upon this in the way that he did. But I think the other thing that's really important is finding a way to always kind of keep your ear, like if the thing you're doing is just taking off and exceptionally working, you got to focus, you got to go all in on that thing. But when the thing you're doing is in that grey area, this is the hardest part, right? If your thing's working, you know what to do. If your thing's not working, you know what to do. It doesn't work. But when your thing's kind of working, in this case, you have $3 million ARR. You know, I've seen a lot of people in these places, right? They’re half a million, a million, $2 million ARR, but just don't have those growth rates. And I think when you're in that world, you have to find a way to say, look, because you have something. You have customers who are paying. You’re actually in a space. You are delivering value. You know a lot more subtleties than somebody would who's not there. But how can you still keep your eyes open? Rather than blinders on focus, we must grow faster, which hasn't worked. That’s why you're in this place. Keep your eyes and ears open to find problems that are adjacent, to find problems that your customers have but that nobody else is solving. Even if those problems feel more niche, because if you think about, email marketing platform is much broader than getting you emails for an email list. But getting your emails from an email list was very desired and unsolved. And so obviously the pull you can get if you do it is going to be much higher than if you're just doing the same thing everybody else is doing. That was just my observation was, like, because it's not the first time I've seen it. Like you look at the Noibu pivot. 

Pablo Srugo (00:13:04):
I mean, you look at a lot of pivot stories, and they're kind of like this. They’re somebody who was doing something in a space. It was going OK. All of a sudden, they noticed something else that was related, adjacent, and different. They solved that instead, and maybe it was smaller, maybe it was an e-shirt, but all of a sudden, the pull was stronger. So that's kind of the observation there is like, if you're kind of stuck, try to go back to those customers, try to go back a few steps to square one, try to ask yourself what problems, top-of-mind problems that customers have that may be small but unsolved, and how can you approach those? 

Pablo Srugo (00:13:33):
And then Cleerly, you know, it's an interesting one. Like, so here's a kind of an MD cardiologist, you know, 10 years, 15 years, something like that. Like a very experienced person who goes and starts in basically an AI startup to detect heart attacks. This company has done exceptionally well. Like they raised hundreds of millions. I mean, it's a long, long road. But, you know, I asked him at one point, I said, like, was there any point at which you thought you would fail? And he shares to me that there was a point where he had 17 days of runway, 17 days. Like that's one payroll cycle worth of runways. And of course, at that point, like failure was very much top of his mind, like very much on the horizon and very much a possibility. He found a way to get just enough angel funding to kind of get him through that period. And then after that, things started to click, and things ended up working out. My observation from that is like when I look at all the portfolio companies that we've worked with and even just founder stories beyond that, it's actually quite incredible. Like, you look from the outside looking in, you look at it Cleerly, you look at the fundraising history, you look at the profile of this founder, and you're like, seems like an up-and-to-the-right story. And you look at many successful companies that have gone on to exit or raise a lot of money and generate a lot of ARR. And again, from the outside looking in, you think to yourself, it must be an up-and-to-the-right story. And of course, some of them are. But it is incredible just how common it is for many of these stories to have been one or two steps away from complete failure. Take Cleerly, if he hadn't found a way to get that little bridge round, he was 17 days. Believe me, you don't get that close away from running out of money by design. He was probably trying to raise money before this, trying to make other things happen, and it didn't work, and finally, kind of pulled the rabbit out of the hat and made it happen. But the fact that he got to that position means that he was just that close, 17 days away from complete failure, and the story ended up completely different. And for me, I don't know, it brings me maybe a little peace. Like, I don't know if that's the right word, but like, you know, knowing that even exceptionally successful companies come so close to that. And it's just, it's part of the game. Like, it's so high-risk, high-reward, building a startup, building something from nothing, that to expect that even if you're right about the thesis, even if you have the right team, even if things are going generally in the right direction, you won't have moments that, really, truly could end up in failure is maybe a little bit naive. But again, from the outside looking, I remember the first time founder, looking at these companies that are raising money, and you assume not that it's easy, but that you must be the only one that feels like this may all fall apart and fail. But I'll tell you, I've been asking more and more founders this question, and most of them, even the very successful ones, were very close to failure at least once in their journey, if not multiple times.

Pablo Srugo (00:16:21):
And I think my maybe meta observation, if you want to call it that, like when I look at all these four stories together and I try and pull out some commonalities, like, you know, leanness as an edge. And it's a weird thing to say because,  you look at it Cleerly, you know, obviously raised a lot of money. Maybe that's a little different. Different than the other ones. Clutch definitely raised a lot of money. Stacker is more bootstrapped and retention.com is fully bootstrapped. But my point is, at least in three or four of those cases, just how much these founders were able to do with very limited resources. And how constraints sometimes can, like you saw with DeepSeek recently, how constraints can set you free in a way, how they can lead to creativity. Everybody wants more resources. And if you can raise a bigger round at the same prices, most people would. Why wouldn't you? If you could have a bigger team, especially post-product market fit, most people would. Why wouldn't you? Like, again, nobody chooses to lay off two thirds of their staff, but sometimes you get forced into situations where you just have a lot less than you wish you had. And there's some comfort in knowing that most other founders have been in the situations and, more so than, they made it through it. Often times it can actually make you better off. 

Pablo Srugo (00:17:32):
Listen, when you go to a restaurant, you eat a nice meal, maybe a fancy one, maybe not. Do you leave a tip? I assume you probably leave a tip. You probably leave a tip 100% of the time. Well, guess what? A review is just like a tip, and I know you haven't been leaving one. So just like the waiter that doesn't get a tip after hours of great service, I’m getting a little frustrated. So, take your phone out and leave a review. It helps the show move up rankings. It helps us get better guests. It doesn't just help me. It helps way more founders. Thank you.