'Weird if it didn't work' | w/ Rob Snyder

And welcome back, Rob. Hey, my man. What's going on?

We got feedback that, uh, the background here looks like I'm in a hostage situation. And I re— I just remembered there, the feedback we got was like, please don't wear white. And, uh, turns out we fixed, we fixed both of those problems.

Now we actually, you've got like a lucha libre thing going on there in the back. And so it's the only thing we know is that you're in Mexico somewhere at an undisclosed detention facility.

Yeah, I actually go on stage as a lucha libre person after this.

So, yeah, you know, I was thinking about that. Like, people don't know about your hobbies or they might, they might not. Lucha libre being one. But you're also— you play, you play guitar like you do. You're a Bills fan. I mean, what else? What else is— you raise a daughter.

Raise a daughter. I lift heavy weights. Yeah, I'm— we, to be clear, we went to Lucha Libre once because you wanted to go.

I mean, I only went because I've got season tickets. Like, I'm still waiting for them to call for crowd participation. I'm just like primed, just like I take 2 scoops of pre-workout and then show up to the Lucha Libre content ready to I remember we showed up, but we just wore the masks the entire time and nobody else was doing that except for the people on stage.

And we just seemed like idiots.

So yeah, anybody, anybody unfortunate enough to be watching, give me a shout if you're in Mexico City and we'll, we'll hit up Lucha Libre. Well, hey Rob, any, anything got you like fired up lately or anything exciting going on?

Yeah. I mean, like I had a, I had a couple of cool conversations this week. One was with a later stage startup. That they reached out and I was like, oh cool, yeah, I've heard of you. This is very cool. I would love to talk. And they come in the conversation and I thought we were just going to talk about the frameworks and stuff. And they come in and they're like, actually we have product market fit in this part of our business, but we're thinking about how to apply this in new segments. Like, oh, that's fascinating. So I just found that to be a, it wasn't a thing. It's like a thing that I knew,, but I just kind of assumed, okay, once you've done it once, you can kind of figure it out the next couple times. But turns out if you figured it out once, you have to figure it out again and you're distracted because you have to do this and you have to manage people and you have to do all this other stuff. So I found that kind of interesting.

Yeah, that is interesting. And the, did we talk about that in the coming up with new ideas or in the, like the case study factory one about how like this is a process that you run through that companies really should be like. It's a good innovation engine for companies that like see an opportunity to move like from their core product into a new— maybe it's a new set of customers or maybe it's actually a different product that they're launching.

Yeah, I think so. I like, I believe that, but it was just interesting to hear people come and say, listen, yeah, we found product market fit here and we're thinking about this next thing as a product market fit shaped problem. So, oh, and so I found that, and the other part of it that I found interesting was, I'm not going to like give too many details, but they, they're like, we only at multiple millions in ARR fairly recently figured out why we are successful in this segment. And what that like keeps resonating with the thing I keep hearing as I talk to successful founders is that Sometimes they know what causes their businesses to succeed and sometimes they don't. And it's just really interesting to observe people who are honest about, yeah, I actually didn't know why people were buying. I thought I knew, but I actually realized when I saw XYZ happening.

That is super, super interesting. Like it's almost like if you've jumped past, maybe you had a great idea, like you had a sense, like you built the right product that you struck demand and now you're looking at it and trying to understand through your framework, which is a replicable framework, not like we'll talk about it today about how it's not just getting lucky, it's like being methodical, but you can actually reverse, like reverse understand. Yes. Like what's actually going on with customers, which can help you dramatically improve the quality of your product. Yeah.

Yeah. And like, like not build the wrong product, not go in the wrong direction. And you don't— there's this old quote, which is like, the buyer rarely buys what the seller thinks they're selling. And the framework here, the set of the demand side thinking, the pull framework, the repeatable case study forces you to get explicit and just like show it to potential customers and say, is this what you're actually buying? Here? Is this what you're trying to accomplish? And it kind of forces you through the discipline of figuring out what people are really buying.

Yeah, I love that. I love that. And it brings out kind of jobs to be done, sort of like undertones. You know, there was a post this week on LinkedIn that I enjoyed. I was following like your activity there. There's a founder who tagged you and said, it seems like there's a million things to do all the time, but there's really just one, referring to demand. Uh, and then another founder commented, Rob's advice is simple, hard to follow, and exactly what I need to hear over and over. And it actually like kind of reminded me of, of Stoicism in a way. It's like the concepts of Stoicism are very simple. It's like, you know, virtues, reflection, um, you know, discipline, like these, uh, being present in the moment, but you need to hear them. Like, it's just so easy to forget them. And, uh, Uh, you know, there's a, there's a daily podcast, uh, The Daily Stoic. And I think that that podcast is successful because the refresh all the time is helpful. So I, like, I was thinking about your content. You say a lot of the same things frequently in different combinations of words, but it's still valuable to like get those kind of reminders because it's, there's so many distractions out there.

Yeah. I 100% agree. Like the. Classic example of this is, you know, look at your calendar at the end of the week on Friday. And if you, if all you do is look at your calendar at the end of the week on Friday and say, did I do what I thought I should have done? Right. That is, you're probably gonna be way more productive than that. Like that's like the most valuable productivity thing that you could possibly do. And it's simple and nobody does it. And so yeah, I think a lot of this we talked about the hard thing about simple things. A couple of weeks back. I think that is— I think that's the favorite, my favorite thing I've ever written because it is just most of these ingredients are simple. Applying them and holding yourself to applying them is hard. Yeah.

Yeah. Yeah. And the other benefit of that blog is you got to talk about weightlifting, which, you know, has been a goal for really All this, all this entrepreneurship talk is just a way for me to become a lifting coach or something. Yeah. Yeah, that's right. Maybe that's, maybe that's the goal. Okay, cool. Well, we're going to get into, I think my favorite Rob Snyder heuristic, it would be weird if today that the blog post is called Could Work Versus Weird If It Didn't Work. Before getting into the content, what's been, what's been on your mind? Why, why was this the right time to write it?

Yeah. So, um, as probably everybody knows, I just get furious at startup advice. Uh, and I can't— there's, there's this kind of— when you're in the pain cave and when you come out of it and when you kind of see the world differently, when you start to see demand, you get into arguments with people and who are like, well, you could just do a bunch of customer interviews. And you're like, yeah, there are examples of cases in which that works, but that's not what you really want to do. You really want to sell. And they're like, but well, but both are good, good options. And so, so I've just been getting frustrated and I couldn't figure out the language to articulate the difference between a lot of this startup advice that sounds right and sometimes works. Versus what I'm trying to do, which is figure out the method and the way of thinking such that it would be weird if it didn't work. And the difference between those, I've been kind of talking about it here and there. And I finally was just like, all right, I think this is, I think I have enough in the chamber to like, to write something on this and put a stake in the ground on it.

Yeah. Yeah. Let's start with some of the things you write in the opening. Which strike a chord, not just because they're practical, but I think they connect really well with what the founder is going through. You're right, this is fine if talking about approaches that could work, things that might work. This is fine if you are diversified like a VC. This is not fine if you're an undiversified founder. In our shoes, we aren't optimizing, we aren't optimizing for the chance to succeed, but instead for minimizing the chance of not succeeding. More simply, we don't want to do things that could work. We want to do things that would be weird if they didn't work. Can you talk a little bit more about that distinction and the diversified versus not diversified?

Yeah. So, so if you— so where to come at this from. So if you're a VC, what you care about is that you have one fund return per fund. What you care about is the payout, not the probability necessarily, because you just assume all of these are relatively low probability. And so because you're making a bunch of investments, you just want the chance that any one of these, and ideally you'd like a higher chance. So you want to invest in better founders, you want to invest in people from da da da, like whatever, right? Or you want to invest in growing spaces., but you're investing in the payout if you're right. We as founders do not want to die. We have a different calculus because we're not diversified. And so there's, there's a couple different ways to think about this. The first way is you could think about it as we don't wanna fail, but that's not quite right. Because there is a world in which you are just struggling along, barely profitable, which is technically not failing. What we really care about is we want to maximize the chance of success, but even that's not quite right. We wanna minimize the chance of not succeeding in our situation. And so when you look at it, the world that way from like, what would be weird if it didn't work? You come up with a totally different set of actions that you take, ways that you spend your time that seem unreasonable to people who are thinking in a could work, who are diversified or who don't have this kind of skin in the game.

That's interesting. It makes me think about, you know, like market sizing, SAM, TAM, whatever, which from with that framing makes more sense from a, like a VC that's thinking like, okay, if I'm investing here, is there a 100x whatever unicorn potential? How big could it be? Yes. Um, but that's mostly irrelevant for like the everyday, I don't know, everyday founder. You can still build like the other, like the thing that I'm wrestling with here is you can still build very big businesses using the approach that you're doing. And so it's not like VCs should ignore this. But it's like the thing that each founder should 100% be focused on is, uh, is different from the thing that VCs are naturally drawn to focus on.

Yeah. Well, and I think, I think there's some overlap here, right? Like we also, so if VCs generally care about the payout, if it works, we also care about the payout if it works, but So we should be shooting to build big companies. I'm not, like, I don't love the idea of just building small companies for the sake of not building large companies. Why not build a big company? But just looking at the payout doesn't, is like not the calculus that we, that founders use in their brains, that I use in my brain, that basically every founder I've ever talked to uses in their brain because they want the big payout, But they want an approach to that that would make it— that, that is not basically buying a lottery ticket. Yeah.

Yep. Yep. And let's, let's get into that lottery ticket kind of like what— so the point of departure here for like how we typically, or how founders might typically approach this is that could it work or what could work? What does that look like in, you know, in everyday life for a founder? Like what is a, it could work approach to developing a product.

And yeah, so, so the it could work approach, right, is, I mean, this infects everything, right? It's, well, if I do a bunch of discovery interviews and I get 10 out of 10 pain points out of people, I could build the right product. They could buy it. Like that's a microcosm of this. Okay, cool. If I just launch it on Product Hunt, it could go viral. It certainly could, right? And all of these things are kind of could work things. If you flip it on the other side, or if I send a bunch of cold emails, I could get somebody to talk to me. I could figure out sales that way. These things all, the challenge with them is not that they can't work. Because they could. They just, it's just coming at it from the angle of it could work means that if you stack a couple of these, the probability of anything actually working goes quite, quite low. And so instead, let's start with like the discovery interviews about pain points, right? Okay. What's your approach there? If it would be weird if it didn't work. Well, I'm going to go in person. I'm going to talk to people. I'm going to do the job firsthand to get an intuition of where demand might be versus kind of arm's length discovery interviews. And then I'm, I'm not going to go away and build something based on feedback. I'm going to get 5 people who I don't know to try to buy it from me, 10 people to, to try to buy it from me, to put money down, right? Once I'm there, It would be weird if that didn't work. And then like, let's take it a step further to make sure I'm not building the wrong thing. I'm gonna deliver that manually to make sure that they keep using it, that they get satisfied after. And so this approach is weird if it doesn't work because you've approached it in a totally different way than what we're typically taught to do.

Yeah. And the weirdness is also valuable. Like when it doesn't mean it never fails. It means like when it fails, it's weird. And you have something to understand about that particular weirdness, um, which is, you know, there was something that you were missing with a, with a, it could work reading over it. I, I was thinking about like the narratives that I run through in my head where I create a fictitious person in my brain. And I think about the series of events and the circumstances they're in. And imagine a product that is solving them and then being happy at the end and buying and like, you know, it just kind of like spirals. And there's this like bias toward that narrative element that gets, you know, a founder or me like excited that, you know, leads us to, oh, isn't this cool? And you start to tell the story to people and get feedback on that story without it being an actual sale that somebody is validating with actual money that, you know, they're saying there's This is solving something that I really, I can't not solve in my, in my business or in my life.

Yeah. Yeah. Totally. It's, it's, it's, you know, the kind of could work approach just leads you towards wishful thinking and it leads, it kind of leads you to go insane in a way because it makes sense in your brain and it doesn't, it's not playing out in the real world. And that's, and like, That's where a lot of the existential stress in startups comes from because it makes so much sense in your brain and you're trying to square what makes sense in your brain with what's happening on the ground.

Is this, is this fair to run something past you? Like with your, the sprints that you run, the first step is a hypothesis. Yes. The hypothesis is almost like the, where, where the, this could work stops almost. And then it's like applying this, like this rigor to the, this could work idea that you have to understand if that's like the thing that will end up being replicable.

Yeah. And so what is the hypothesis though? The hypothesis is a, is again, I guess, but it is, I believe this person in this situation has demand and would be weird not to buy, right? Versus this is a hypothesis of somebody who could buy. Right? No, we, what we have to do is we have to start from the perspective of who would be weird not to buy. And then we go try to sell to them and see what happens. Yeah. Then if they don't buy, it is weird. Just like you said, versus if we do it based on somebody who could want our product, who might have pain points and problems where our product would be, would be objectively valuable. We go talk to them and because they could buy, it's not weird if they don't buy and we don't really learn anything in those conversations.

Yeah, that's, that's super interesting. Um, you know, you talk about a couple stages where this applies, the, the idea stage, the first customers and early traction stage and the figuring out repeatability stage. Um, I, I think we've, we've touched a bit of the idea stage already. How about, Or any of those three that you want to jump into?

I think like the broader point is this applies in every task you do at every scale. It's kind of like this fractal concept that it's what market do you target? How do you approach this stage? How do you approach this task? When, right, you have a potential customer who is a really good fit and it seems like they might buy, how do you make it weird that they don't buy? Do you just kind of send a follow-up email or do you say, hey, I'm going to be in your town next week, like I'm flying out and do that. And so this approach infects everything.

Yeah. Yeah. You talk about that there's two parts to it. There's identifying the ICP and then there's the case study model applied to one customer. I think we've— you've addressed the ICP in this case, or the ideal client profile. Yeah. You know, who would be weird not to buy? On the selling to one customer, you really kind of went deeper in this one about you need to choose one. And that's something I see, you know, in the Slack with the founders and stuff, you get a lot of questions on. It's like, all right, I've got these like 3. Can I go after all 3 of these? Like, how do I— or, you know, how do I approach that? How do you think about responding to that?

Yeah, I mean, now I've got the language for it, which is it could work, but it would be weird if it worked. It almost never works. Like, it is so hard to figure out one that trying to do three is almost guaranteeing you fail. So, you know, like worst case scenario, sequence them based on which one would be weird not to work. Out of the three.

Yeah. And so it would be like tactically run a sprint using person A or archetype A, whatever you wanna, whatever you wanna say about that person with demand A. And then if you're failing with that sprint over and over, it's like, okay, let's move to B like that.

And yeah, it's basically you're creating a hypothesis for group A. I believe group A would It would be weird not to buy this in this situation. You have 5 sales conversations with them and everybody's like, this is the stupidest thing I've ever heard. I have no projects related to this. Why are you wasting your life on this? Say, hmm, that's very useful. Thank you for that. Let me check out B, right? And so, or you have 5 sales conversations and 3 say, Oh my gosh, this is the, this must be how Alexander Graham Bell felt when he invented the telephone. This is amazing, right? And the other two are like, yeah, this isn't relevant right now, but holy cow, if you had talked to me 3 months ago, I would've ripped this outta your hands. You do something different in that scenario. You're like, okay, cool, let me compare and contrast, refine my hypothesis, and let's sprint after this. Like, B and C be damned, I'm going after A.

Yeah, or if you run into like lukewarm, I feel like more than just those extremes, like you more frequently run into interesting idea, like let me know when it's developed or, you know, not willing to put skin in the game on it. And in that case, like maybe it's time to see if any of the three have that like red hot or white hot demand center that you talk about. And so it, you know, it can be valuable to have some ideas of who to run through, but just like, don't try to do them at the same time.

Yeah. And what you're looking for in those sprints is not lukewarm because lukewarm isn't really demand. Demand, pull, right? Maybe we should do something on this, which is like the difference between demand and pull, right? Pull is when they are like, yeah, I've been trying to do this. I'm blocked. My options suck. Sounds like you fit. Pull in. It's not a, "Okay, well, this could be on the priority list," right?

Like, that is equivalent to, "This is the stupidest thing I've ever heard." Equivalent in outcome, but less helpful.

It's a kind way to say that.

Yeah. Maybe let's jump into some of the, like, practical advice for founders from this. You write a really interesting line, it will change your approach to hiring, fundraising, priorities, product, sales calls, go-to-market, who to take advice from. What do you, you know, you've, what do you mean? Like what, choose your favorite two of those that are kind of not intuitive and tell us about them.

Hiring is the fun one, right? Which is, Usually I'll just give like an example, hiring your first sales rep or hiring in sales, right? Early on when we're hiring in sales, it's very easy to hire people who could work out. They, well, yeah, they, they have the right energy. They have the right, and like we can craft the job description based on that. We can the interviews and we can like, we, person has the right vibe, they have the right energy, they've sold software before.

I could imagine them being successful here.

I can see them being successful, right? If you craft the, if you look for people where it would be weird if they didn't work out, if it didn't work out, you would look for somebody who has sold something very similar to something, to a very similar target audience in an outbound heavy environment at the seed stage. Right? Where it would, you would like look for somebody whose experience is such that it would, there's the fewest possible variables that are different between their experience and you, such that it would be weird if they didn't succeed. Hmm.

Is there something in there around desperation? Like this person doesn't have an option to fail in a sales role. Like if you're, what if you don't have that luxury where you don't, you know, you don't have candidates that are that that close to what your product is or your vertical?

Is it find them? Find them. Find them. Like how would you make it weird that you don't talk to those people? It's not, it's, yes, it is kind of, we often settle on this for somebody who, you know, the person that we find, the person who applies, that's not the right way to come. And again, this is how it kind of impacts at every level, right? The other angle on hiring is When do you hire? Do you hire when a sales rep, when they could come in and figure it out? No, you hire a sales rep when it would be weird if they weren't successful. Yeah. By which I mean, you already know exactly who you're selling to. You generally have proven this out a couple of times and you know the, you know the general flow of it and you've done it without a bunch of founder magic. That's when you hire.

Yeah.

Yeah. Yeah. When it's like working, you understand the physics of it. You can hand it off to somebody.

Yeah. That's interesting. I like the discipline there around, you know, just don't hire the wrong people. Like everybody's seen how painful that is to unhire some, like to figure out your way out of a bad sales hire or out of a bad, you know, in general hire. Choice of a co-founder, whatever it might be. Uh, the, uh, it would be weird if it's an interesting one. Any, any of those others? Priorities? Um, fundraising? Uh, fundraising is kind of interesting.

Yeah. Okay. Here's the, here's the thing around fundraising, which is, um, how do you, how do you approach a fundraise such that the VC would be weird not to invest in you? Hmm. How, how do they think of, so It's basically how do— at early stage, it is how do we construct a narrative that makes it so obvious of the magnitude of the opportunity and that we are so unhinged that it would be weird if we didn't succeed, right? Like that's my version of an investor pitch. On the go-to-market side, we've already talked about this. Right? The toll booth is an approach to go-to-market where when somebody has demand, we are figuring out what's going on at that moment and developing an approach to go-to-market such that at that moment, it would be weird if they didn't hear about us. Yeah.

Yeah. I love it. Um, any, anything else we want to add on this? We've got a couple mailbags that we can, we can jump into real fast.

No, let's rock.

Highly recommend the blog or the Substack. It's again, my favorite heuristic. So, and I think it's really, really cool. Okay. This one is from Nev. It was a comment on the Substack, where to find ideas. Rob, what if you have a hypothesis, do cold outreach to talk to them and no one replies?

Yeah, this is pretty normal. Usually the reason this happens is because we are either doing, like we copied a HubSpot sequence that is, dear sir or madam, do you have this pain point? Our radically new solution, AI, da da da da da, blah blah blah. And of course nobody's gonna respond to that. It's either that or it's in the uncanny valley between like, I'm a founder, I'm a cool founder, would love to chat with you. And sales, which looks like, you know, hey, I'd love to get your feedback. I'm working on XYZ product that promises to 10x your ROI, right? So it's just none of these messages will work and you haven't learned anything. Your cold outreach is not testing demand. Your cold outreach is just getting people to a conversation. In the blog post, I think it's titled Be Weird. That's my approach to messaging.

Hmm. Yeah. And that, as, as you said in the past, like the goal there is pique their curiosity almost. It's like get somebody to sign up for a, you know, a 15-minute call or 30-minute call to have a conversation with you, which is very different from I'm interested in your product. Like those are, those are separate things, separate messages.

Yeah. And then, and then like the follow-up question is, but what if I change the messaging? What are they going to think? It's a bait and switch when I try to sell them my product. It's like, yeah, they will if you try to sell them your product. What you're trying to do is see if they have demand. If they don't have demand, you can try to sell them your product and it won't work.

Yeah.

If they do have demand, they will pull for more information about your product. They will make it a sales call.

Yeah, that's— I really like that. They will make it a sales call. All right. And one, one more in the mailbag. This one's— I think it's Petr. P-E-T-R. Is that like an Eastern European spelling of Peter. Anyway, sorry, sorry, Peter, if I've— if I'm butchering your name. Let's see, he writes, first want to thank you for sharing your work, shifted how I think about building products. Stuck on one thing, though, the very first step before forming a pull hypothesis. You say if your life depended on the outcome, you'd get firsthand experience, get your hands dirty and go where your customers are. Here's my problem. I don't even know who those customers are yet. So where do I go if I don't have an idea or an industry in mind? How do I decide where to go or who to observe?

Like, what are you doing, Peter? What are we doing here? We got it. Like, I like— I get we want to build a business, but like, you don't build a business by saying, I want to build a business. You build a business by saying, I want to serve X kind of person, right? Like that's, that's where it all starts. Now, often it starts with a product idea and then you hit your head against the wall for that until you realize that it's about who do I wanna serve? But that's the foundational question. So here, here's, uh, um, what you can do is create a list of people that you might wanna serve. And like I would suggest pulling in any of your previous experience of people you've worked with or any kind of firsthand things you have, creating a list there and then just go spend some time with them. I know there's an HBS guy I know that did this and he just was like, listen, I don't know what product I want to build. All I know is that I want to serve somebody that I enjoy serving. Yeah. Cool. That's the right way to think about it. So he went and like spent some time with like, I don't know, solar panel installers. And he was like, I hated them. So I crossed them off the list. I don't think, I don't know if it was solar panel installers, but I'm just making that up. But like, that's a good heuristic, right? I hated them. They hated me. Like, great. And then he just went down the list and kept going in person and just learning and kind of doing the work with them and found that he really liked wherever he wound up in. And that's where he figured it out. So that's an approach you can take., but like, remember that the purpose of building a business is not to build a business. It is to serve a specific kind of customer who is trying to accomplish something in their lives and their options are not good enough. And by real— like that is the core of it. It's not to build a product. It's not to grow revenue to the moon. It is to serve. And the sooner you can embrace that, the less you will get distracted by the trappings of the other things.

Yeah, I like that on the choice of customers, like choose people you don't hate and, or that you actively like and care about. And there's a, I don't remember, I think I picked this up from the Founders Podcast. Is that guy's name, is it David Sinja or something like that? I'm forgetting, but there we go. But one of the things that he talks about and he applies to different ones is like, do work. This might actually be a Bloomberg, a quote from Bloomberg, but it's like, do work that feels like play, cuz you'll do that like longer than anybody else will. And so choosing something that you actually enjoy and are, are passionate about to the extent, or that you enjoy more than anybody else in the world can be, that can include serving customers that you enjoy being around. Like your, you know, your Harvard, your Harvard friend.

Yeah. I would, I would reframe it that though towards serve somebody who you really want to spend time, who, who you you just really appreciate spending time around and that you, that you are just fascinated by or, or something like that. Yeah. Because the, the thing of like, do what you, what feels like play to you, like then everybody's gonna build a fucking Travel Trek startup or everyone's gonna just like put their head down in code all the time. Cause I, I like building, if building product feels like play to me, so let me lock myself in a room and, and do that. Right. Like we want it to be, we want that to be pointed in the right direction.

Yeah, I feel you. That was, to be fair, if it was Bloomberg, it was in the context of building terminals for financial data. So it's not, it's like, it's not all like, you know, totally, you know, hobbyist.

But I wake up every morning thinking about databases and some people do.

If you do, do that because like other people—

I just read the Oracle biography and it's a fact. We're going to do an Oracle versus Microsoft thing someday to talk about the nouns and waves. And it's just like the, the, the, it's just fascinating how much they think about like databases or, or kinda like the basic programming language on to, to get onto an Altair. It's like, it's fascinating.

Yeah. Just like totally obsessed with these things. Um, well, awesome. Thank you, uh, Neb and Peter for, for jumping in. Anybody else leave comments on, I check the YouTube and, uh, uh, and the, the Substacks for comments that we might be able to address. So drop 'em in there. Anything else, Rob, on your mind before we let folks go?

Nothing I can think of.

Awesome.

All right.

We'll catch y'all next week.