The $1M ARR calendar

Hey Rob, good to see you, man.

How's it going?

Uh, it's, it's going great. And according to today's post right now, instead of talking to you, I should be doing outbound. So we're, we're going to get into that in a moment. Uh, but anything, uh, anything on your mind before we jump into this week's post?

An update for our listener. I, by the way, I keep getting like 1 or 2 people a week reaching out, claiming to be the listener. And so you all need to like stop that because there is only one. And so you haven't shared any of the data with me, but you just keep telling me there's literally one listener per episode.

It's not a lot more than that. It's, uh, it's, you know, given, uh, given the depth of insight that we're discussing here, it's shocking that, oh yeah. Yeah.

But anyway, it's shocking that we have one listener. Yeah. Um, uh, 4:15 this week. That, that's all I'll say. We'll keep rolling.

All right. We're climbing. Um, hey, I'm gonna, I'm just gonna jump into something that you write in this week's post. It's called The Calendar Standard, what your calendar should look like as a B2B founder. And, uh, this is, uh, I'm, I wanna get your, I'm just gonna read this thing real quick and then give us the context on why you've put this together. Um, what you write is you might say that you want your startup to grow fast, but your calendar might reveal that you actually want to find important seeming reasons to avoid growth-related activities, or that you want to make work for your team, or that you believe that you need to model all aspects of the unknowable future before taking action. There's, there, one or two of those parts were like a little bit of a gut punch to me. And certainly 6 months ago would've been a much stronger gut punch. But anyways, Rob, give us context on why, what you're doing with this particular post, why we're focused on the calendar, you know, what's on, what's on your mind with this one?

So a couple of weeks ago we did the standard, which is basically like, here's what your metrics need to look like in order to claim that you have product market fit in order to earn the right to potentially be in that top tier of fast-growing startups. And so Those were the metrics, which is fine. And people, you know, I've gotten quite a few messages from people who are like, that was a slap in the face. But thank you for that. Also, like, uh, that's great. But I had in my mind, there's a, there's a founder and I'm going to call him out. He's, I don't know if he even listens to this. Um, but he's a friend of ours. Uh, his name's Michael Levitz and he's building a startup and he always reaches out to me. Yeah. Every couple of months he'll reach out to me and say like, basically, okay, fine. Your advice worked. I tried every possible, and whether it's outbound or whatever, I tried every possible way to not follow your advice and just kind of like went back to it because it wound up working. And so what I've been thinking about is, okay, cool. What's going to prevent a startup from hitting the standard? What's going to prevent a founder from hitting the standard? And it's just like how you spend your time. That's it. That's the thing, right? It's, it's the difference between you and the startup that takes off. Is how you invest your calendar, like the finite time that you have this today, this week, this month. And so I thought, okay, cool. Why don't I just put together an example calendar of if you're serious about hitting the standard, what will your calendar look like so that you can look at this example calendar and compare it to your actual calendar. And say, oh wow, one, the standard is actually quite achievable without, you don't have to like work an insane number of hours to hit the standard. And two is like, oh, okay, cool. I should change my calendar. Here's what's actually, what I'm actually, you know, how, how I'm spending my time the wrong way.

Yeah. Let's, uh, let's quickly recap for a listener who might have amnesia. Like, what are we talking about with the standard? Um, so that was, uh, basically what you did. We'll link to this, like, mid but it's going to be, you should just pull that up and read it. But you lay out the startup as a case study factory and there's 5 elements that you say like, here's what you need to hit. You need a repeatable case study. That's the most important thing first. You need a certain number of calls, first calls per week. You need, I'm trying to remember.

Oh, I thought you were, I was like waiting for you to nail all of them.

Well, if you, yeah, yeah. There's like first calls, there's close rates, I'm going to— I'm not going to get into that.

Yeah, yeah, yeah.

So it's—

yeah, it's— and I'm doing it from memory too. It's case study, number of first calls per week, calls with pull, close rate of calls with pull, and cycle time.

And then—

and I think there's a post-sale one too. Success rate.

Yep. Awesome. Perfect. So basically, and what you do with that is you kind of like lay it out. You're like, if you want to be one of these startups that finds hypergrowth and takes off, you need to be getting this number. And there's a, you know, there's a little bit of nuance there based on your contract size, whether you're selling to enterprise, whether you're selling to small businesses, if you can close on the first call or et cetera. But basically it's like, if you're not doing this, this is what your aspiration should be. And now what we're talking about is the mechanics of, okay, you've decided you want to get to that level and how do you structure your day to do that? Let's, uh, you know, there's one other, one other thing. What, what we're going to do, you, you do something incredibly helpful and deeply frustrating, which is you actually give us a calendar that we can just replicate if we're actually committed to doing it. Um, but before we get into the, into the calendar, yeah, I want to pause here to talk about operating philosophy. Um, this is one of your ideas that I think about quite frequently. Um, what you write in this one is your calendar, of course, reveals your operating philosophy. Your theory about what matters. Rob Snyder, tell us, you know, let's take just a quick moment. What do you mean by operating philosophy and why is it important?

So I think like a year ago I wrote a post on the operating philosophy and I still think it's like one, it's one of my favorite ideas and it is that, you know, there's like stated versus revealed preferences, which we've heard about. Your calendar. Expresses what you believe is important. It basically reveals a philosophy about how you think the world works and therefore how you should invest your time. And so, um, the, if you look at your calendar, it tells a story and it, and that story hopefully is, I'm serious about building a fast-growing startup. But if we're really honest and we look at our calendars, that's often not the story we see. That's the story we have in our head, obviously, but it's, but like, it doesn't matter the story that's in our head. It matters what plays out in time on, you know, every day. And so that's the, yeah, that's the idea of the operating philosophy. It's revealed. It's your revealed philosophy. Of what's actually important if we just look at your calendar and use that as the mirror into your soul.

There's two examples with the operating philosophy that are, you know, that made it resonate with me. One of them came, you know, I think it was something you said to me like a couple years ago actually. It was something like a lot of founders believe that It is imminent, basically like success is imminent because success has been imminent and sort of for a lot of us, you know, if you went, if you did the like the McKinsey, BCG, Bain thing, or you went to a top business school or you graduated, you know, top of your class in computer science, whatever it was, you're just like used to being successful. And so you sort of extrapolate that and believe that as a result of me being the kind of person that is successful, I will figure out being successful. And you, you kind of just, which when I reflected on myself and what I used to, you know, how I used to operate, it was like, yeah, I kind of, I kind of just thought it was gonna work, uh, eventually. And you were like, that's not like, welcome to startup land where you gotta build your own like thing. Yeah. If that's what you believe, you're just not gonna get there. And the, and the person that believes I've gotta earn this, like I've gotta figure this out, like if that's their philosophy, they're just gonna run circles around you. Um, and another one, this is, this one's kind of silly, but My, one of my family members actually told me at one point, like a decade ago, she was, and I was thinking about this through the lens of the operating philosophy. She was like, sometimes I think I wanted to lose weight, but then I keep eating tacos and I'm reminded that I don't lose weight if that's the thing that I do. And it's like, and the operating philosophy is I can eat whatever I want and I can still like have the body that I want. And that's, you know, it was an interesting application of like a similar idea where she was reminded like, Oh, this is serious. Like if I, if this is my goal, I have to do the things in order to achieve that goal. Totally.

Oh yeah. Like the operating philosophy concept is so useful. I just like pulled up the old blog post and like what, one of the things that, so, um, I'll read a couple points from it. Cause I think it's, I think it's good. If we choose to spend our time heads down building product and not talking to customers, maybe our operating philosophy is that the world is waiting on bated breath. For us to reveal our brilliance. Or if we try to sell, but we go through the motions selling reluctantly, we approach sales in a reluctant way. Maybe our operating philosophy is that we should be rewarded simply because we're trying, right? Like these are, these are almost like pathologies that are revealed by our calendar and how we, we spend our time. And so, okay. Let's show what the calendar is for if you are, if you are serious about hitting the standard.

Yeah, let me, uh, and I'm going to share that, um, uh, if I can figure out how to screen share. All right, and if you are listening on, uh, on a platform that doesn't, or, you know, if you're not in a space where you can actually look at a screen, um, We, there, I recommend pulling up the post itself, uh, cause Rob Snyder has just laid out what the calendar should look like. Rob, can you talk us through the key elements here? And then there's a couple of things specifically I have questions about. Yeah.

So, okay. Like I did just didn't feel like varying the days very much because that would have been too much work. So what I'm, what I'm doing here is I'm giving you a rough template for what a calendar would look like. And this is, by the way, 8 to 5, not, not like 9 to 9 or 8 to 8, right? Like this isn't a ridiculous calendar. There are a couple of, of components here. Like there's 2 hours spent scheduling sales calls, whether that's doing outbound, whether that's, you know, getting inbound, like whether there's a variety of things you can do, cold calls, all that. Um, there are 3. First sales calls in a day, there's 90 minutes of go-to-market admin. There's at least one second or after sales call. And there's a, there's, you know, an hour for post-sales calls. If you have all of that on your calendar, you still have 2 hours for anything else that you want to do while working a leisurely 42.5-hour workweek.

Hmm.

Yeah.

And let's, let's talk about. A couple pieces of this. One, maybe let's just define some of these.

Um, so first, first, sorry, sorry, sorry. If you do this calendar and have like a $10K annual contract value and hit the standard numbers, you're going to be, you're going to be adding like over $2 million ARR a year with this calendar. I just want to make that clear too, which is that like, it often seems unbelievable, unreasonable, like all those kinds of things. This calendar can get you there. So anyway, let's—

Wait, let's, yeah, let's pause on that for a second. That one's important. So in the math that you're doing in your head is, yeah, what you should be doing to hit the standard, uh, like you're, it's generating a certain number of sales calls. It's closing at a certain rate. It's delivering successfully after that. Um, and basically what you're saying is with this calendar, with, if you're, if you're hitting the standard and you're operating and like, this is the mechanics of hitting that standard. The math, essentially like the conversion rates work out to like, this is your, your guidepost for getting to that $2 million.

Yeah. Yeah. And it's, and, and to be clear, a $10K ACV, the $10K contract value is pretty low for the startups that I typically see here. And so, right. Yeah. Some stuff might move, but, but yeah, this would just at $10K contract value. With this calendar, you get, you add $2 million to, I think it's like $2.4 million in ARR per year.

Yeah. Yeah. And if your gut instinct is, I'm different because special Snowflake, just hold, like dare to hold yourself to a standard that isn't perfect, but that is, you know, or what's, you know, what's a better standard that you have? All right, Rob, let's, uh, scheduling sales calls. Oh, are you talking outbound? And why, why is that one 7 to, or 8 to, 8 to 10 AM? Like, why is that the first thing in the morning?

Yeah. So just a pattern that I've typically seen, um, this can be, so this to be clear is whatever works. I'm giving you 2 hours to do whatever works every single day. And so often that is outbound, like that's just because you can pick up a phone because you can do whatever. Um, and so I've found that, uh, and there's like an additional section on outbound. We can talk more about outbound by my book review on outbound, uh, still pissing me off. Uh, the, um, but, but 2 hours at the beginning of the day is actually like a pretty solid thing because what tends to happen is if you just block off that, every single day, it's the first 2 hours of your day. You will get it done. If you let it go till later, it's like the thing that nobody looks forward to doing. And so you'll find reasons not to do it unless you do it first.

Yeah. The way, the way that, and I've recently moved more to this. I used to put it later in the day and I would be like, oh, I just need to get this, that like there would be something with my business, like on the product side that was like on my mind. And I would start the day doing that and I would be like, I just have to cross this off. And then I would get 3 emails and then I would get, and I would like, you know, sort of black out and disappear into running the business and wake up 3 days later and be like, oh, like I didn't do the thing that I needed to do. Like it was just distractions piled up from the team or whatever it might be. So I love that it's there at the start. All right, then you've got, you've got, you know, essentially like a 2-hour block there that's like sales call 1. Um, and, and go-to-market admin. What are you talking about with go-to-market admin?

Sometimes you have to send follow-up emails. Sometimes you have to prep for other calls. I, I, uh, you actually don't necessarily have to spend. So, so what I have here in, in the blocks are like a couple of sales calls and some blocks for sales, for go-to-market admin, which would be, I don't know, just time that you spend prepping for your next call, time you send spot following up from your last call. These are often useful blocks of time to have.

Yeah. Um, and you've got a, you know, a, a second sales call, um, post-sales call.

What do you, what are you getting at with, um, onboarding, customer success, troubleshooting, what, what, whatever it might be, but like something for somebody who has already bought.

Yeah. And then everything else that's, yeah, product, that's coding, that's, you know, what, what, what else, what else could it be?

Right? Like if you're not doing these, uh, if you're not doing these core things, like what, what else? But yeah, it's, it's pro— like, yeah, it, it could be product work, it could be team stuff, it could be investor updates, it could be, it could be whatever.

Yeah. Yeah. And, uh, like Rob, do you have anything else that you would say about what is the operating philosophy that is reflected in this specific calendar?

This calendar says, I am, first of all, I am front-loading getting people to talk to me. I am front-loading pipeline and I am focused on go-to-market as the engine that's going to cause our startup to work.

Yeah. Yeah. I love how simple that is. And there's, um, I'm going to stop, stop sharing here. Um, you know, you, you also lay this, lay this out separately. Um, you say, uh, you know, in summary, it's an hour and a half of initial sales call per per day, half an hour of later stage sales calls and an hour of post sales call per day, 1.5 hours of go-to-market admin, 2 hours of scheduling initial sales call and 2 hours of everything else, you know, but for me, I was looking at this, I was like, I'm not, there's parts of this that I'm not hitting. I think it's going to be easy. Like you've just made it so easy here for us to ask ourselves like binary yes or no. Is this the shape of my calendar? Am I hitting this? You talk about objections. Let's hit objections that folks might have. And you outline two of them. One of them is, but I don't know my repeatable case study yet. And the second one is, but I, but I can't get people to meet with me. Rob Snyder, can we take those actually? And one other thing you write that I forgot to mention at the start is this is the calendar for 0 to 1 million. So it's the pre-hiring of sales reps. Stage, anything you would add on, on the stage or how this, yeah, who it applies to. Yeah.

So I'd say this is after you have, you're like pretty clear on what your case study is, but before you've hired a sales rep, once you, once you start doing this, like you're not going to do this calendar yourself forever, unless you want to bootstrap a startup and it's like, cool, this is what my calendar is going to look like. So that I can get us from zero or $100K to $2 million ARR. And guess what I'm going to do again next year? I'm going to do this again, or, or at some point I'm going to hire somebody and I'm going to just give them all the sales calls or all the first sales calls. I'm going to offload stuff to them. So at that point, it's, it should be pretty straightforward exactly how sales, sales works, how the engine works. Um, and so it's, yeah, this is for that stage where it's. Kind of on the path to repeatability, becoming increasingly repeatable.

Yeah. What would you say for, okay, let's say you've also worked with companies that are $50 million, something like that, but they're still trying to figure out something with their, with pull. Like what do they, how would you, you know, think about helping that business leader or that maybe they're a founder, maybe they're not, maybe they were a later hire, maybe they're the, you know, sales guy or something. How would you talk to them about what should they be thinking about with their calendar?

This should be their calendar. This should be, um, this is often, so like if you're launching a new product, this should be your product manager's calendar. Um, like the, the person who's, or the owner of that product, the person who is, who is leading that product, right? Like what I often find is that person wants to do product things, um, and features and all that kind of stuff. And then they have a salesperson they're partnering with who's doing the sales on it. And it just, it just doesn't work that way. It has to be, there has to be kind of one person leading. It's, it's, it's not multiple different things. It's one whole thing. It's not parts. It's a whole. And so the one person has to be leading the whole.

Yeah. Fascinating. All right. Let's hit these objections, but I don't know my repeatable case study yet. What do you, um, you know, what, what's your, uh, what's going on with that? And what do you tell that, that founder?

Yeah. So, so if you don't know, if you don't have a pull hypothesis, if you haven't figured out, if you haven't sold to like 3 or 5 people, cool, totally fine. In that case, you're not going to kind of be, but your goal is to figure out what your repeatable case study is as fast as humanly possible. And so you need to generate a pull hypothesis and test the pull hypothesis in a batch of 5 sales calls. And so that's what your calendar should look like. I created a calendar variant for that case, um, that does this within like 3 days. You can do it within a week. You can do it in one. I've seen people do it in one day too. So it, you know, you can do it in one day at a conference and then just go through this very quickly. And so, yeah, cool. Fine. We, there are variations of the calendar.

Yeah. And let's hit the, let's hit the second one, but I can't get people to meet with me.

Yeah. I mean, cool. This is the thing I like always the objection I always wind up getting. And it is the majority of cases when I review outbound from people who say this, one, they're sending basically no outbound. They're, they're like not doing any outbound or two, their messaging is awful. And it is, um, you know, it just has this, uh, again, I'm saying this because I've done it. If I read my old outbound messages, It reads as if I, I don't like there, there is a philosophy that comes through in outbound messages and it's almost, it never looks good on the sender. And it's, it's basically like, you know, I've copied some random template. I, for some reason, am saying not selling anything or something like that in the message. None of this makes any sense. So, um, I will probably have to do another thing on outbound at another point in time, which I just hate.

It's what we all want, Rob Snyder.

I hate it.

We love the outbound.

Hate it. Hate it.

Hate it.

Um, the point of outbound is you are not the main character in the outbound. What you want isn't the main character in the outbound. It's they are the main character. What they, what's interesting to them is what you should design your message around. And their pain point, like getting their pain points poked by a random person, uh, via email or LinkedIn or whatever is not actually super interesting to them or hearing about your product also not super interesting to them. Send them something that's actually interesting and then like, okay, fine, cool. And like, we're going to, we're going to go into that more in detail at another point in time. I'm just angry at Outbound at the moment. Um, Uh, but sometimes like that, so if you're in a situation where you're stuck and you've tried a bunch of things and it doesn't work, the answer is go find somebody who has sold into your target customer and figure out what their playbook is and just use that. It is unacceptable to stay stuck like this and just say, well, given that I can't figure out getting people to meet with me, I'm just going to doom scroll and get angry at the world that my startup isn't taking off. It's like, go figure it out.

Yeah. Yeah. Um, yeah. One of the one, you, you highlight a couple things that folks are doing with outbound. Um, you know, and one of 'em, you think the goal of outbound is to sell your product. No, the point is to just get the meeting, especially, uh, early on. And that one I thought was a really good characterization of thinking about most of my LinkedIn, uh, you know, inbound that's coming in. It's like, it's almost all too long and it's too focused on a product. And trying to sell in that. Awesome. Rob Snyder, what actions should listeners take after accidentally listening to this or reading your posts?

Yeah, look at the calendar, look at your calendar, compare, contrast, stare into the mirror for a little, think deeply and reorient towards like, just fix your calendar.

Yeah. Yeah. I'm putting blocks on mine is like tactically what I've been doing is especially for the outbound, like blocking off 2 hours a day to just do that, to make sure that it's protected, that people aren't dropping random meetings on it. And to also hold myself accountable to like, am I focused in this space? Anyways, I hope this was—

What I'll leave you with is smart people, like If you're smart, you will find ways to outsmart yourself to avoid doing the things that you really want to do. You'll find all sorts of reasons not to. And that's the goal of the standard and the calendar. Like, those are— that's what I'm trying to do here is put you in a position where you can't outsmart yourself. You can't find another door out.

Yeah, maybe just like try it for a week, see if, you know, what do you have, what do you have if you're, if you're struggling in that, that 0 to 1 million phase, like try it for a week, see how this feels, make yourself, you know, and then you can make a decision and leave an angry rage post on, on this and say Rob and RC wasted a week of my life. Awesome. Well, why don't we, why don't we leave it at there, leave it there and we'll catch everybody next week.

See y'all.