Scaling a values-led podcasting platform with Craig Hewitt

Brian Sierakowski on September 22, 2021


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In this episode, we talk with Castos founder Craig Hewitt about building a remote team, acquiring other companies strategically, the EOS framework & who it works best for, and more!



Craig is the founder of Castos, where he leads of team of 15 extremely talented individuals that are crafting the best podcasting platform in the industry. He’s a husband to an amazing wife, and father to two incredible children.



Castos is a full-service podcast hosting, distribution, and analytics platform, with an industry-leading production service built right in. In our platform, you can easily create, promote, and distribute your podcast and grow your audience.

Learn more about starting and growing a podcast at the Castos Blog.



Brian Sierakowski: Welcome to Founder Chats by Baremetrics, where we chat with founders and hear about how they started and grew their businesses. My name is Brian Sierakowski, the Director of Ops at Baremetrics. This week I talked to Craig Hewitt, founder of Castro.

In this episode, we talk about Craig’s background and experience being an entrepreneur.

We also talked a lot about the actual operations and mentality of running a business and also EOS, which is something that I’ve heard of, didn’t think I knew about, but maybe we do it at Baremetrics. 

Anyways, onto the conversation! 

Brian Sierakowski: Hey Craig, thanks for joining us on the podcast today. How are you doing?

Craig Hewitt: Hey, doing great, Brian. Thanks so much for having me. 

Brian Sierakowski: Awesome. So Craig, you are the founder of Castos.

Craig Hewitt: Yeah, I am. 

Brian Sierakowski: The CEO as well, right? 

Craig Hewitt: Yeah. I wear a lot of hats, like a lot of founders.

Brian Sierakowski: Yeah, yeah. President… chairman of the board…

Craig Hewitt: Exactly. 

Brian Sierakowski: Well, awesome. Thanks so much for being with us today. I really appreciate it. Usually I like to start by saying, Hey, take us back. Where did your kind of entrepreneurial journey get started? 

Craig Hewitt: So it’s funny. My entrepreneurial journey got started in podcasting.I think a lot of folks kind of scratch their own itch or work in an industry or niche where they have a lot of experience and really understand the customer and the problems and things like that.

And for me, that was podcasting. I was a huge listener of podcasts. In a previous life, I was in field-based sales in the medical world selling to doctors and hospitals and stuff. I was traveling all over, going to doctor’s offices and hospitals and stuff like that, and had, you know, several hours a day in the car.

And so I just listened to a ton of Pat Flynn and Tropical MBA and all those guys, and just really got the bug. And it was like, I’m going to start a podcast about entrepreneurship. And so I started a podcast. It’s still going today. It’s called Rogue Sstartups. And just wanted to introduce, you know, entrepreneurs, other folks that I know in this bootstrappy kind of space and really quickly saw like, Man, this is a lot of fun, but it is a pain, right?

All of the editing and the recording and show notes and marketing and all this kind of stuff is just a hassle. So I started a productized service around it called Podcast Motor. And that was kind of my way to get out of the rat race and kind of get started as an entrepreneur. I was able to quit my day job after a couple of years of nights and weekends.

That kind of led me into what is now Castos. We’re a podcast hosting and analytics platform. The product I service is still a part of it. And Podcast Motor is now called Castos Productions. That’s the real quick version of it. I saw the pain in myself and, you know, we created a solution for it.

Castos Productions now is a kind of done-for-you podcast editing and production. 

Brian Sierakowski: That’s awesome. I had a similar attraction to podcasts myself, where I was driving around a lot. I had kind of a, maybe a similar role. I’d be interested to hear more about your life in field sales.

I had long drives and I realized like, especially if I was driving into the office in the morning, just like listening to NPR and, you know, realizing that the thing I liked the most is the interviews. Sometimes I’d be driving into work and they’d be like, you know, 45 people were killed in an explosion.

And I was like, Oh my God. Like, I don’t want to out myself for like, not being aware of what’s going on in the world. I kind of quickly realized that, you know, the information diet that I was taking in kind of would… hearing about all the terrible things that were happening in the world wasn’t the best way to show up and be my best self. 

So that’s when I kind of found. Podcasts, as well, these extensive interviews. Maybe sounds like it was somewhat similar for you. 

Craig Hewitt: Yeah. I think it’s great that we can choose the information we consume to a really high degree of specificity. It’s amazing. 

And really high quality content too, which is kind of the new development in the last few years, I think.

Brian Sierakowski: I just got hit by an overwhelming wave of like, just realizing that we’re doing a podcast right now. And it’s like, I got hit with the meta wave of being on a podcast and talking about podcasts.

I’ll cease that line of inquiry now, but yeah. I’m curious to hear, how was field sales for you? How did you get into that sort of role? 

Craig Hewitt: Yeah, so that is most of what I had done in my professional life before this. I have an engineering background, proper engineering, not like a developer background, and sold pretty technical equipment to the hospitals in the cardiac field.

And it was great. I mean, I say even to this day to our team members, people who have worked for big companies.. You know, I worked for fortune 100 companies… understand things about how companies work and how we all should work inside companies that some people who have just been freelancers all their lives don’t don’t really get.

I think, especially for us as founders, having seen the other side of it, as much as we despise some of the things like, you know, the TPS report, we do understand the usefulness of it. And, and if we choose not to do some of those things, we know that it comes with a price maybe in the end.

We try to not have a lot of red tape and meetings and garbage like that, but we do understand that communication is really super important. And I take that from my kind of corporate days. 

Brian Sierakowski: That’s cool. Is there anything in particular or like a mistake that you see smaller companies making, maybe because they’re not exposed to… some of these are like solved problems in the larger corporate world.

Craig Hewitt: It’s a thing that we’re going through right now. I think it is something that happens in teams around our size. So we’re 14 people right now. When you’re one or two people, it’s easy for everyone to understand that they have to own the entire thing they’re working on.

You know, every part of marketing or every part of engineering is, is their world. But you know, we’re five developers on our team right now. And we’re starting to see a bit of.. not “that’s not my problem”, but like “I can come and write the code and submit the PR and then like, someone else is going to deploy it, you know, or “I’d assign this ticket to someone else and it’s not my problem anymore”, just because, you know, we’re a bigger organization than two or three people. 

The type of work that we did was very consultative to where we really partnered with our customers, in my corporate life before. And so that’s just second nature to me to say like, Hey, we are here standing next to the customer.

I think that I try to impart a lot of that on, on our team. Some people haven’t worked in that kind of world before. I think that’s something that I bring over that some people on our team haven’t kind of had before in their work life. 

Brian Sierakowski: That’s interesting. Have you found any techniques that you’ve been able to deploy? I’ve experienced the same thing where depending on the size, or any teams that you work on, really, anybody in any field or any department within the company can become super insulated, even surprisingly on the marketing side or sales side. 

It’s like somehow, even though your full-time job is to communicate with customers, you know, it’s possible to do any job without talking or really like, deeply thinking about the customers.

I think, especially developers, because there is kind of inherently some distance between the people who are, I guess, quote, unquote, supposed to talk to the customers and then the people that actually do the work. But it sounds like maybe, or I don’t want to put words in your mouth, but maybe you’ve had a little bit of experience with that.

Have you found any techniques that work to kind of bridge that gap in a productive way? 

Craig Hewitt: Yeah, I think that that specifically, you know, everyone on our team talks to customers. That is just how we work. Everyone in our team participates in support to some extent, at least. So they all log in, they’re all seeing tickets, they’re all chatting with customers. 

I think it’s a really valuable thing that we do because they do just get in the habit of talking to customers. And when they do that, they naturally interface with other parts of the company to help solve customer’s problems. So that’s just something that we’ve baked into the DNA.

I know there’s a lot of arguments for things like, developers shouldn’t be doing support and it makes them less efficient and all this kind of stuff. And maybe that’s true. But you know, at the end of the day, a developer handling a support ticket from a technical perspective is absolutely the best way for a problem to get solved and, you know, marketing and sales folks, obviously talking to the customers and then talking to engineering and product and things like that as a result of that.

A lot of those discussions internally start with a conversation with the customer, whether it’s a sales call or a marketing campaign or a support ticket or a new feature, it all starts with the customer. And then the discussions internally kind of cross-pollinate between groups.

Happened pretty naturally because yeah, nobody has all the answers, uh, or they want to get a perspective from another part of the company like, Hey, customer conversation made me think about this. Never thought about that. What do we think about this? That’s kind of how that starts and it’s pretty natural. There’s no ongoing process that we have to follow or checklist or anything like that.

Brian Sierakowski: That’s awesome. And I’ve heard a lot of anecdotes and experienced firsthand. A similar thing has even specifically around developers being in the support queue, you know, where it’s the type of thing where the support team has been pushing the development team for like weeks or months, or years or whatever, to fix something.

And it just always kind of gets prioritized at the bottom of the list. And then you bring the development team into the support team and they’re talking to a customer. It just kind of feels like they get curious and they go, oh, well like, yeah, what is going on there? I always believe that, you know, the closer you can get to the customer or the more synchronous, like if you’re on a phone call with somebody or you’re on a video call somebody, that’s always like more valuable data.

I’ve seen the development team go from this is a ticket to be prioritized to, oh, well give me five minutes and I’ll fix it right now. 

There’s no bad intent by anybody in there. There’s just something a little bit different in looking at a long list of tasks in a backlog versus talking to a person who’s trying to solve some problem or make their business better or whatever it is that they’re trying to do.

That kind of humanity aspect kicks in. It’s like, I want to help this person. Craig seems like a good guy. I want to help them out. I wanna make sure that his business does the best that it can and I have the skills to do so. 

Craig Hewitt: Yeah. Yeah, absolutely. Folks listening to this might say, oh my gosh, I couldn’t put my developer in the support queue and have them answer emails, but they’re amazing at it. All of our developers do it. We’re on just kind of a regular rotation. So you just, I mean, five or six weeks, uh, someone’s on support rotation there for the week.

And it’s amazing. The tone that they use is fantastic. And they get really curious about the technical things that the customers are seeing in a way that I, or our other product people, you know, wouldn’t because they think about it from a different perspective. So I think it was just a really healthy kind of variety of ways that we view things that customers are experiencing.

Brian Sierakowski? Awesome. Can you speak a little bit more to how you have that set up logistically? It sounds like you have a rotation, but it’s just like one of the developers in the support queue for the whole week? Or how does that play out? 

Craig Hewitt: Yeah, that’s exactly right. So each developer takes a week at a time and they’re on kind of a regular rotation.

So again, every five or six weeks, they’re there on some kind of developer support. And they only handle tickets that the support team escalates to them. So it’s typically only a couple of tickets a day and their goal then is to…You know, they really have two options, right? Is this a bug or an issue? 

And then, you know, an issue is filed for it. And hopefully they can write the code to fix that bug. That week is really the goal if we’re firing on all cylinders, that’s that the goal is they see the bug, they write the issue, they’d write the test, they write the code to fix it. Or this is not really a thing for developer support, but here’s how we can train the customer support team to handle this themselves in the future.

So it doesn’t need to get escalated the next time they see this. 

Everything should fall in one of two buckets. Of course, it’s never a perfect world. But, the goal is that the developer on support, shouldn’t see the same thing twice. That’s the goal we’re shooting for.

Brian Sierakowski? Cool. That’s awesome. And what is the rest of the team doing while you have the elected support representative? What does everybody else do during that time?

Craig Hewitt: On the development team, you mean? 

Brian Sierakowski: Yes. 

Craig Hewitt: They’re doing their regular feature and bug related stuff. 

Brian Sierakowski: Got it. So they’re still working in a mix of.. I guess the thing I was wondering was does that make it so that the rest of the team is strictly focused on feature development. But it sounds like they’re handling a mix as well the bugs that one person hasn’t knocked out and those sorts of things. 

Craig Hewitt: Yeah. You know, we’re a relatively mature platform. We’re about four years old. So most things that we’re working on these days are new features and that’s where most of our time is spent.

But some things are, you know, Hey, this is not really a bug necessarily, but it isn’t quite perfect. And we need to kind of refactor/rework how this thing goes, just because customers run into bumps along the road when they encounter this thing sometimes. And that’s maybe the 20% of stuff that the development team works on.

The rest is new features and integrations and things like that.

Brian Sierakowski: Awesome. Cool. Well, I want to go back a little bit. So you were on the road, you were doing field sales, and then you kind of found this personal revelation with podcasts. Do you remember how you came across podcasts in the first place?

Craig Hewitt: Gosh, that’s a long time ago. I don’t remember. The strange and kind of sad thing is I was in San Diego at the time, which is kind of like the epicenter for a lot of the entrepreneurial podcasting stuff. And I found a lot of these folks just as we were leaving there, but no, I don’t remember how I came across podcasting, but the two people I mentioned earlier, like pat Flynn and then Dan and Ian from tropical MBA, Rob Walling from Startups For The Rest Of Us were some of the first that, that I kind of got hooked on and, and everything went from there.

Brian Sierakowski: Cool. Yeah. I don’t think I remember either. I don’t even think I remember the first batch and I don’t know if you remember this, but were they called podcasts at the time? I almost feel like there was this sort of level of  morphism in the very early days of like, well, what, is it exactly that we’re even listening to here?

Craig Hewitt: Yeah., I’m not that old school, see everything was called a podcast. It downloaded automatically onto your iPhone. So yeah, it wasn’t quite that old school. I know some people that you got to plug it into the USB on your computer and sync it and all this. No, that wasn’t my journey. 

Brian Sierakowski: Drive to the mall. There’s a guy there and he gives you the audio files. 

Craig Hewitt: Crank the wheel and everything. 

Brian Sierakowski: Light the fire.. and then the ball goes down the ramp and then that triggers the broom.. So you kind of found this thing and then can you speak a little bit more in detail about how you went from being a listener to becoming someone who’s like, oh, well, you know, what was that?

Do you remember what that moment was? Where like, oh, well not only can I listen to these things, but I could also make one as well. 

Craig Hewitt” This was in the part of my entrepreneurial journey where I literally knew nothing, you know? And so I just said, I want to be in this space.

You know, I want to be in this world. I want to know people that do this so that I can learn from them. Maybe we can do things together. And, and the only way that I knew that was to just start a podcast and interview a bunch of them. That’s how it started. The third person I interviewed ended up being my co-host and it’s been more of a co-host show since then, but yeah, I think I just saw that I wanted to participate in this community.

This seems like a really cool lifestyle and way to earn a living and support my family. I don’t know anything about it, you know, so I just want to have as many conversations with smart people as I can. And that’s really how the podcast started. And I mean, I think a lot of folks you talk to about their podcast, the stories of “Oh, because of my podcast, I was able to, XYZ” are amazing. 

We have people on our team now who I know from podcasting. You don’t even have to interview them because you’ve had them on your podcast, you’ve been on their podcasts, you know, them from this huge body of work that they do, that’s all public.

And you just like, Hey, let’s work together. It’s just a slam dunk. We call it the digital CV, right. It works on a personal level. On a brand level is, you know, you think about this podcast for you all, as you go into a partnership discussion or trying to sell a big enterprise deal or something, you can say, Hey, look, we can go have this meeting.

I can tell you all about what we’re about, or you can go listen to the last 20 episodes of my podcast and get a really good feel for who I am and what we stand for and what we do here. 

I think more and more people are seeing that these days. Especially things like a resume and a pitch deck and all this kind of stuff are so contrived compared to the body of work that you put out in public for everyone to consume, including your customers and your prospects.

And it’s just so much more powerful. 

Brian Sierakowski: That’s interesting. If you have a podcast that’s out there, it’s relatively easy for someone to know who you are and get to know you. in a way that yeah. To your point, like the resume, I think it’s an issue. I haven’t, I fortunately have not needed to apply for that many jobs.

I think it’s actually pretty common that people don’t apply for a lot of jobs. And then you sort of face down with the situations, like, okay, time to update the resume. And I have like one page to sum up who I am and my experience and my skills, but also my personality. And what’s important to me in a way that I think is like, kind of like maybe, maybe not deceptively difficult, but that’s what I’ll say.

That’s really challenging. I think it is really easy to come up with an incomplete picture of somebody. It would be relatively straightforward if somebody wanted to like, get to know me before they even reached out, this is what they could listen to and watch any recorded content that I have out there.

And then probably after like five minutes of that. They would know whether or not they wanted to interact with me. They’d be like, I don’t know if I want to know if I want to be around this guy too much. 

Craig Hewitt: Yeah. I mean, to that end, we don’t, we don’t ever ask for resumes when we’re hiring, just because yeah. It is a really contrived artificial source of information about someone, but much rather, Hey, let’s, you know, show me your work. If you’re a developer, show me your open-source contributions. Show me your test project. If you’re a marketer, Hey, let’s work on this campaign together. What have you done in the past?

That all of that is just so much more authentic than that one page of bullet points and dates. Really abstract stuff that a lot of times has absolutely nothing to do with the job you’re applying for. So we just don’t even ask for them. 

Brian Sierakowski: It’s interesting. I agree. Like the more you can get away from abstraction. I’ve been hiring developers for a while and that’s the way it’s always like the first meeting is like, let’s grab coffee or, you know, whatever, grab lunch. Let’s have a quick conversation just to see, like I’ve had candidates that just seemed like they weren’t actually interested or like, didn’t want to talk to me.

Maybe that’s more to the previous point I just made of like, they’re like, oh, geez, I don’t know about this guy or giving like one word answers of like, Hey, like, well, um, cool. You do. Or you just went to a developer bootcamp. Can you tell me about that? Like how was that? And they’re like, good. Yeah. So, you know, but you know, most people don’t do that.

They get through the second one. And then usually that one for me is like, well, bring your laptop or whatever you have, you know, if you want to bring your desktop, that’s fine. And then let’s sit down and work together on a project that you’re working on. You know, it doesn’t matter, whatever code base, whatever tool set that, you know, home field advantage for you.

And then let’s just sit down and then they’ll show me what they’re working on. And I’ll go, usually it’s like error stuff of like, oh, well there’s a field there. Well, what if he put a number instead of a string in there? And it breaks. I’m like, okay, cool. Let’s fix that. And then you can just kind of like, watch, like how fast are they  in their ID?

How fast are they? Like, how well do they know the tools? How long does it take them to determine if it’s like a model versus a view thing. A lot of times they even make passing references to, oh, well, here’s where I would write a test. If we weren’t, we weren’t in an interview, I’m going to skip that for now.

But you know, a lot of times people are like, you know, not even thinking about tests and you get to your, exactly to your point. It’s like, I’m not even putting you in front of a whiteboard. It’s like, just show me you doing the thing that I’m going to ask you to do. And then you’ll know, shockingly you’ll know how good they are at doing the thing that you’re going to hire them for, to, you know, much better than if you ask them, you know, a bunch of hypothetical things or, you know, you know, describe to me on a piece of paper, how good you are at this.That’s not particularly useful. 

Craig Hewitt: Yeah. And I think, I think it goes both ways, right? Like they want to.. especially developers these days. Well, everybody  in this kind of, you know, SaaS, digital world, everybody wants to do this, you know? The competition is really strong. I think, I guess for both ways. But it needs to be a really good fit for both sides.

Developers have a lot of options to go work other places. We’re finding that, you know, we need to sell Castos on the vision of what we’re doing, just as much as they need to sell them and who they are and their experience and their skills and, and all that to us. And that’s, that’s awesome because then it is really this genuinely good fit.

If we get to that point of saying.. We do test projects a lot, but, but I think we’re moving to more of just a, yeah, like a technical conversation, you know, like, Hey, I’m looking at this thing. How would you think about this? Like, I don’t need to see someone’s code necessarily if they can think through something appropriately.

And so we’re moving more towards that, because then it shows us how they think. And then it shows them kind of the things that we think are important and that we focus on because yeah, that good fit on both sides is hugely important. 

Brian Sierakowski: Have you found anything that works particularly well to sell the vision or kind of set up like who the company is and what you stand for in that interview process?

Craig Hewitt: Yeah. I mean, it’s funny, like if you would have told me, you know, three years ago, even that I would be talking about our values on our site, but like we reference our values all the time. And if you would have told me three years ago, “Craig is going to use the values on the website in job postings and interviews and when we’re filtering candidates, I would have told you you’re crazy.

But we took a lot of time to think through those and really distill them down to who we are and who we want to be as individuals and as a company. The cool thing about taking that much time to get that a hundred percent really close to a hundred percent right as we can is that then it’s just a yardstick against which we measure how we’re doing, and the people that we’re looking to bring into the company and how good a fit they are. 

So we talk a lot about our values and then like you, you can kind of see like, do people start squirming, you know, or do they really click with what you’re talking about? And that’s the starting point of, of a lot of the, the culture side of things.

Brian Sierakowski: Interesting. It’s like what you’re saying at the beginning around, there are some elements of that corporate culture that can be misused, but that might be, you know, the corporate values is something that is like, oh, there’s actually, there’s actually some good ideas here. There’s actually, there’s actually something useful here for us to make use of.

Craig: Some of our candidates come in and say, Hey, I was reading your about page. And I saw this value you listed. That is so incredible. Can you tell me more about that? And to me, that’s just like a huge light bulb. That’s a great sign. 

Brian Sierakowski: Would you share some of your, some of your values with us?

Craig Hewitt: Yeah, I will share all of them with us. I have them right here. Hang on just a second. Awesome. So yeah, we have six values. The first is: have a winning attitude. We work hard every day to be the absolute best podcasting platform for all of our customers. Second one is: We are humble, help others. First, we think of our team members and customers’ needs before our own and live to serve.

Or the next one is practice fanatical commitment to detail and consistency. No detail is too small. Nothing is overlooked. Building best in class tools takes consistent effort and focus over years. Have personal integrity and accountability, especially as a remote team. We’re individually accountable for our responsibilities every day.

This is both to our team members and our customers. Encourage individuality. A significant part of our strength is the diverse backgrounds that our team comes from. We encourage everyone to proudly be themselves and let that shine. And the last one is Communicate openly and proactively. Take the time to let all parties know what’s going on with us, how we’re feeling and what we need to be successful.

Brian Sierakowski: That’s great. Yeah. I love that. We went through a similar exercise. I sold one of my previous businesses and we were kind of installed as a sub business unit inside of a larger company. We kind of went through a similar thing. We actually had a lot of the, a lot of the same things that you had as far as like, especially around communication of like, it’s kind of my, my nature as well.

I do think there’s some natural, you know, rubbing off of the people in leadership of like how that actually enforces and informs the culture. I’m curious, like, I’m sure there’s probably some obvious and straightforward ways that culture has informed the way that you’ve proceeded. But, and if you have some of those, I’d love to hear it, but I’m also curious about any really challenging situations where.

Maybe you wanted to do something else, but relying upon your values, you were like, actually, you know, we’re, we’re not going to do that thing. We’re going to do something else because this is more in accordance with our values. 

Craig Hewitt: A couple of things come to mind. One is we recently raised a fundraising round of about $750,000.

And again, if you would have told me that like three years ago that I would be talking about our values as it relates to fundraising, I would tell you you’re crazy. But it really the values are just kind of who I am and who I want us to be. And, and so we raised money because we think that we can do more good for the company and for ourselves and for our customers with more resources.

That exists in most of our values. You know, that end result. And then fundraising is just like the vehicle that lets us have a better chance of achieving it. So that’s an example of why we did something and we have several examples of why we didn’t do something.

Most of it revolves around bringing people on or continuing to have people on the team because they did or didn’t align with our values. Especially the communication one. It’s just so obvious when everyone else is, you know, hanging out in slack and goofing off and showing all these GIFs and stuff like that.

And then you just never hear from this one person and you’re like, this is just obviously not a good fit. Right. That seems like a cop out, you know, reason for someone not to continue staying on the team. And if you have to let someone go, it’s like, Hey, you’re not a good fit, but that’s just honest to God the truth, right? This is who we are and this is who you are. And like, it’s just not great for everyone to continue to try to fit this square peg in a round hole. You’re going to be much happier somewhere else. And we will be too. And I think that’s kind of a graceful thing to give someone that, out and say like, Hey, I just don’t think this is a good fit.

You’re going to be much happier somewhere else, doing something different. The other side of that is we will too. 

Brian Sierakowski: Yep. We will also benefit from that. Yeah. I saw a conversation around kind of like the no assholes rule. And my, my reflection on that was that the type of, you know, asshole quote unquote, that will manifest in your business, it’s probably.

A lot less of an asshole than what, like, it’s like, yes, if somebody’s walking around your office and flipping desks over and like punching, punching holes in the wall, you’d be like, yeah, this guy, this guy’s an asshole. We’ll get them out of here. 

But if you have, so I think the actual manifestation of like, maybe to your point, and maybe this is not exactly the same thing, but it’s like, it’s like a lesson version of like, well, if everybody else in the company is like, if you have a value at responding to your teammate quickly, and this person like always waits until the next day, or, you know, they’re, they’re just not courteous when they’re doing, especially if it’s like a review process, a material review or a PR review or something like that.

It’s like, oh, this person’s just not quite as nice. Like I think that’s the actual manifestation of the no assholes rule. It’s like, it’s going to be much more subtle. It’s going to be less cartoony than what you might imagine when you say, Hey, like no assholes. 

Craig Hewitt: Yeah, it just creates friction. There’s enough of it doing this in a startup that you want everybody as onboard as you can with, without having to even think about those things. 

Brian Sierakowski: Have you ever been called out by a teammate for not following or not doing something that doesn’t line up with the values?

Craig Hewitt: Oh, that’s a good question. Not that I remember is what I’ll say. I don’t recall. I’m sure there are things I’ve done and whether I’ve been called out for them or not. I don’t know. 

Brian Sierakowski: Yeah. I figured that was a long shot, but it’d be a funny story of you got the whole company together and you’re doing an all hands and you’re like, yeah, we’re going to raise, you know, $20 million and somebody raises their hand and they go, Hey, what about this? Like, we’re in this for the long term, like, right. And you’re like, Ooh. Yeah. Yeah. Cause here you are correct. Maybe we should reevaluate that.

It’s kind of hard for you. As someone in a leadership position, it’s a little bit harder for you to not. Fall in line with the values, because it’s like you said, it’s kind of a reflection or representation of who you want to be. So it kind of like, almost like by doing, not exactly, this is going to sound a little bit harsh, but by you doing what you want to do that is going to naturally represent and reflect like what you’ve set out in the values.

Craig Hewitt: No, I think it’s spot on. I think it’s spot on. You know, when we got to eight people, II started thinking a lot about our culture and values relate to culture a lot. The phrase I heard that really resonated was your culture is the personification of your values.

I think it was like either the Buffer guys or the Helpscout guys talking about that. And so it’s just like, the culture is who I am, you know, as a leader and who everyone you’re bringing to the team is, and hopefully they all are aligned with the values that we state. 

Brian Sierakowski: So if somebody’s listening and they’re there maybe at a smaller scale company, or maybe they’ve not gone through this before, but they’re, they’re listening to this and they’re like, wow. Having these values written down sounds really, really nice and really useful. 

What would you recommend as a step one to get them moving in that direction? 

Craig Hewitt: Yeah. Yeah. I think that just listing out in plain English, like who you are and who you want to be is a really good place to start.

And, you know, like we all kind of stand on the shoulders of giants. I looked around at a lot of companies that I respect and, and saw the things they were saying because in a lot of ways that’s the same thing, right. Buffer is an amazing company. We want to be like Buffer. And so I looked at what they had to say and, and you kind of, you’re able to pick and choose and Hey, yep.

That one kind of doesn’t really make sense with what we’re saying. And this one does, and I want to add my own unique twist on it here. And I think it’s very much an iterative process where you write A bunch of this stuff down and you have a list that’s much longer than it will be in the end.

And then you let it sit there for a week and you come back to it with a fresh perspective. That’s how we did it. 

Brian Sierakowski: Interesting. Well, that seems super achievable. Just look around and see what resonates with you. And maybe you find that some of the things that resonate with you are aspirational.

Like, oh, well this is like the type of company we’d like to be. I guess, how would you, and maybe this doesn’t happen in practice. Maybe it’s only me imagining how this process goes. But like, if you have a company and they’ve written down this big list and they find that there are some, maybe they have some value that they find as something like, oh, well like only 40 hour weeks or something like that.

And then they go into a hard situation where there’s a requirement, you know, basically someone’s made a mistake and things are not going to plan and someone needs to spend more time and, and the founders, the leadership finds that like actually, you know what, I’m a kind of okay with that in this limited scenario, like how would you coach them and recommend to them if they’re like, well, is this a value that you want to continue to work towards? Or when is it okay to sort of let go of a value because you just, for lack of a better word, like the way that it sounds, but they actually didn’t, it doesn’t actually embody the organization. 

Craig Hewitt: Yeah. I don’t know specifically, I guess, but I would say generally that all of these things are, are written in pencil from our end, right.

We want to revisit them often and we want to consider them and we want to always be aware of them. And if something doesn’t make sense for us anymore, we can all agree that it doesn’t, and then it’s time to change it. It’s my company. And if I say that 40 hour weeks on what we’re going to do anymore, then, then that’s.

And there’s a good reason for it that is supported by other stuff about who we are and what we want to be, then I think it makes sense to change. I think a lot of folks get too hung up on, Hey, I said this thing, so I’m going to stick with it forever. You know, not wanting to be accused of being the flip-flop politician, but I think there’s so much that changes on a daily basis in our business that we have to have some things that are relatively firm and strict, and then we have to have some things that, that are going to change a lot.

Those can be different things at different times. 

Brian Sierakowski: Interesting. And it sounds like you lean on that communication aspect. So if you were to say one week, Hey, this is, this is what, we’re, what we’re doing. This is who we are. And then the next week you say like, ah, actually I thought about it and that’s not who we are.

You know, it wouldn’t just be like a one line email that says, you know, like everybody, please strike this line from our values. You would probably include a little bit more context of like, Hey, this is kind of the rule that I set and I thought it was going to help us get to this direction… and then I realized that, whatever the reason is, it’s actually totally tangential to the thing that we’re was trying to do. I don’t know how transparent you are, but maybe say something like, Hey, like I was just wrong. Or, I thought this is going to be good for us and then as I actually saw it in practice, like I was just wrong about that. It totally sucked. Like it was, it was awful and that’s, you know, a hundred percent on me. 

Craig Hewitt: Yeah, absolutely. Absolutely. I mean, that happens all the time and I am pretty transparent about it. I’m doing my best and definitely making up a lot of this as we go.

A lot of these things are experiments and some of them will be wrong. We had one recently where we got on the EOS bandwagon pretty hard around the end of last year. And for, I guess like the last half of last year in the first quarter of this year. At the end of the first quarter, I was just like, God, this is just not like, this doesn’t feel right.

You know,  I want to not do this anymore. And, so we didn’t have quarterly rocks. We didn’t have milestones, we didn’t have the typical kind of weekly meeting. And we got kind of listless, you know, people weren’t really clear on the goals and the big picture things we were trying to do, and they didn’t know what success looked like.

Starting this quarter in the third quarter, we went back to EOS had rocks, talked about rocks a lot, talked about the thing that we want each kind of group of the company to be doing and, and big things that we’re trying to ship or achieve this quarter. And it’s great because I hear everyone talking about their rocks and they’re very aware that like, Hey, this is when I show up at work, this is the thing I’m trying to achieve. 

We didn’t do it because like, I don’t want to be a big corporate behemoth, but something that I have come to realize (and it’s really counterintuitive to me because I’m an entrepreneur and I absolutely don’t want this), but is pretty much everyone who wants to be an employee at a company wants to be led somewhere.

And for everyone listening to this and for all of us, we don’t, you know, we want to make up the rules, but pretty much everybody else needs direction and feels really secure when they’re very clear about what the thing is. That was a really hard thing for me to get over because yeah, I mean, I just want to show up and do whatever I want to do today.

That requires or carries like a fair amount of cognitive load for me. But if I can say, Hey, support team, this is the goal, right? We have a net churn percentage that we want to try to achieve this quarter. However we achieve it, we achieve. And then that takes all the guesswork off their plate and just lets them focus on executing.

Brian Sierakowski: Yeah, I think that’s really, that’s really valuable and I agree. I’ve noticed the same thing where everything that has made me a terrible employee throughout, basically my entire career makes me a pretty good leader within a company. And yeah, I’ve totally found the same thing. And I think there’s like, there’s such an art to it. 

You want to make the goal specific enough that it’s clear and measurable and nobody asks like, what do you mean by that? Like, it should be pretty clear. In doing that too, I think one of the benefits that you give as a leader to the people that you’re giving those goals to is you’re kind of like eating the uncertainty of it.

Like you’re saying like, well, like we do kind of a similar thing too, for like our success team. We have this, this add on that basically for everybody who uses it, it makes the company more money than we charge for it. So, like 30% of our customers use it. That was my opportunity to say, Hey, well, let’s get that to 50% like, can we, can we get free money to 50% for everybody? 

And then that just gives them something. And maybe I think that’s kind of also inherent in what you’re saying, how they get there and what they want to try and how they want to experiment. 

You sort of have created the bounds of what you’re expecting and you have something that they can report on and something, you know, just kind of, it gets the department out of blank sheet of paper territory, but then you have total freedom to, as long as you can with a straight face say, and I thought this was going to help us hit our goal at the end, then you’re totally good.

It’s not like a failure elimination exercise or I don’t know. How do you think about it from that perspective? 

Craig Hewitt: This is like a spectrum. You know, like how deep into these kinds of things you go …it’s not binary. But the place that we are, and we’re just getting into is when we have these goals, a person or two people can be responsible for a goal.

And then they’re responsible and they’re like leadership level folks, right? They’re not, you know, like a junior developer responsible for a net bug goal or something like that, but they’re responsible for the goal. And then the onus does flip a bit to them to say, Hey, you’re the leader of the support and success team, our net revenue churn number is your number.

I am here to help you in any way I can. The people in resources and tools and process and all that kind of stuff. And we will come up with the plan together of how to achieve that. But it’s your goal. You know, I own all of the goals to some extent, but, but this is primarily your goal.

And this is something that I’ve heard from folks that really kind of drink the EOS Kool-Aid. It just lets you abstract away those goals too, and have someone else be responsible for them and the end. We’re just starting to see this where we kind of reviewed our goals in a meeting a couple weeks ago and then immediately I had three different DM’s from different leaders in the company saying, Hey, I got to talk to you about this thing that I’m responsible for now because I don’t know how we’re going to do this.

It was great. We hopped on a discussion and talked about this thing and went, we need to hire this person over here, get this tool or implement this process. And like five minutes they were, they were totally cool with it and they have a plan and a roadmap and they have all the tools they need. They know that I’m here to support them, but it is their thing.

That’s the big key for me. Otherwise it would just be a company of one and I would be responsible for everything, but we can achieve so much more. If people know what the goal is and that they know that I’m here to help them achieve it and that the company is behind them. That’s awesome.

I’m realizing we do more. I’ve never been at a company that has been going through the last company I worked at, started doing EOS after they got rid of me. So I don’t know. I don’t know if that was a part of the playbook, but it seemed like it was at a time… it sounds like you’ve had good experiences. Is EOS something you’d recommend to other businesses?

Craig Hewitt: You know, I think that we’re just the size now to where it really makes sense. And the reason we stopped doing it before is we were just such a smaller team that it’s silly when you’re five or six people because the founder owns all of those.

There’s less sense communicating all that. And certainly no one else is going to own many of those goals. So, you know, at this point now we have kind of leaders in each of the parts of the company that are of the caliber who can own a goal like that. So I think just the size we are now, or, we have the type of people on the team to where it makes more sense, but yeah, it’s been fantastic for us so far.

Brian Sierakowski: Yeah. Cool. It sounds like maybe the trigger is when each of your departments has somebody that could reasonably be in charge of that department. That’s when you might want to kick in. If it’s the person on the support team is also the person doing all the support and the person on the development team is doing all the development, then maybe that’s a little bit premature because then it’d be like, okay, well, we’re going to set a goal and I’m also going to do the goal. 

It feels very hand to mouth before you hit that, that type of scale. 

Craig Hewitt: That’s how we felt. I think everybody’s a little different, but that’s how we felt.

Brian Sierakowski: Maybe like if we put a number on it, maybe like, sounds like maybe like 12, 12 to 15 people might be kind of the entry point, depending on the shape of your business. 

Craig Hewitt:  I would think that, yeah. I’m sure they would tell you that too. Again, I’ve never interacted with ROS, but I’ve heard, I’ve always heard it kind of peripherally.

So it sounds like something, something useful for people to look into. Maybe you can speak to that too– if a company is in that right size, they have 15 employees, they have department leaders, like what were you feeling that made it a good fit for like, just to kind of connect anybody who’s listening to this?

Was it, you know, I’m responsible for everything or kind of what were the thoughts that you’re like, I’m going to reach for this tool to try to solve this. 

Craig Hewitt: Exactly. It’s not that I am doing everything, beause a lot of other people who are doing a lot of things in the company, but yeah, at the end of the day, it’s all on my shoulders and, and I am very kind of wary of like premature optimization and premature structure and process and things like that in an organization.

But I think most founders of companies like ours are too late to do some of these things. If you look at your company, right. Big, bigger companies, right, has all this process in place, it’s natural to impart those processes. When you acquire a new company for us, starting from nothing, from a process and structure perspective, doing that first bit of process or adopting that bit of structure seems like this thing that you should never do.

I think that a lot of founders struggle with that because they don’t want to be the stick in the mud. They don’t want to be the person to introduce the process. They don’t want to be the fuddy-duddy corporate office space kind of guy. But I think what, like what you’re, what we’re trying to unlock in the end is what if the 14 people on our team can operate at such a higher level to where we’re all more successful, we’re less stressed. We all know what is going on all the time. We know what the thing is, and we’re happier and more productive at work like that. 

That’s really what we’re trying to do. And it came from me shouldering all of that for too long and just kind of said, fuck this. Like, I can’t do this. I can’t, I can’t be the person that everyone comes to for everything anymore.

And then you got to say a little bit, like, maybe it’s like six months too early to do this, but in two years we will have absolutely had to do this a long time ago. So it’s about the right time. 

Brian Sierakowski: You want to kind of get out of the like mech suit CEO where it’s like, yeah, there’s a marketing team, but just kind of like, you are like, you are driving, like you’re, you know, you’re lifting that arm and you’re pointing it in the right direction.

You said, okay, go this direction. Yeah, totally. And I totally agree with you if like it’s, I think if anybody is, is hesitant to sort of put these sorts of processes in place, I’m actually kind of similar, cause I ran my own business and then I kinda came into this private equity world and you’re right.

It’s not totally opposite. It’s actually working within this environment is as close as I’ve ever been to running my own business, which is really cool. But there are other people who are running businesses who are not, you know, career entrepreneurs and they really, they get to kind of just like lean back into all these great proven processes where I feel like I sometimes I’m in the situation where I’m like fighting upstream of like, well, you know, I need to do everything at least first so that I can tell other people what to do.

And you know, like, well, you know, if I’m not willing to wake up at 4:00 AM, then I shouldn’t expect anybody else to wake up early. We have an international team in every time zone. So it’s always a bad time for somebody. But yeah, it’s like when you kind of set the goals and you get out of people’s way, then you see people, they have this awesome opportunity to step up and then they get to kind of almost in the same way that.

It’s a safe environment for me because I’m running a company within a portfolio of other companies kind of, you make it safe for them because it’s like, well, you’re running this department within, you know, hopefully a functional, well run company. And so you have a little bit more flexibility, but you also get the kind of, you know, get that joy of like, Hey, I had this idea and I tried it and probably is going to tank, but sometimes it works and that feels really good.

We had a guy join the team. He was at Google previously and he was just kind of laughing, is that in one of the other portfolio companies. And he was just like, I thought our pricing was too low. So I ran an experiment the next day and I got data over that week and I realized that, you know, we could raise our prices by 20% and you know what, actually, I think it’s more than that.

And then I was just laughing with them like, oh, when you were at Google, did they let you change the homepage at all? Or what was the process there? And he was like, yeah, no, you’re, you’re like 14 layers, you know, separated between you and the product obviously. Cause like one, one miss pixel on the Google homepage costs them like $14 trillion a second.

It’s just different scales and different experiences that you can have working in a company. 

Craig Hewitt: I have a question for you, if you don’t mind. How do you all approach that kind of individual contributor contribution back to kind of the vision and the plan and the process and stuff like that.How does somebody on your team bubble things back up to leadership? 

Brian Sierakowski: Sure. Yeah. It’s actually funny hearing you talk about EOS cause it seems like it’s a pretty similar set up that we have. And probably some of that’s just been amalgamated through the fund, but yeah, we have quarterly goals and I set those quarterly goals and they’re like, usually like big things, big rocks one might say. It’s something department wide. Like, you know, this is the amount of revenue I want us to get to. 

And then it’ll be something like, if there’s a big experiment or big project that we want to complete, for example, I think it was quarter two. Maybe it was quarter one. Stripe was changing the API, that they were the API that we were using to interact with Stripe data to super core, to our business, that API was going away and we needed to move to another one.

So that was an example of like, that would be a big rock for us so that the development team obviously is leading that, but the support team is supporting it. And the marketing team is like providing information to the customers. And then there’s any weirdness going on the sales team needs to be looped into that so when they were talking to customers, they were aware of like, oh yeah, you’re experiencing migration pain or whatever the case is. 

And then we’ll have like, kind of like special projects too. So if any of those actually materialize I’ll share about those and then. What I’ve been doing, I’ve just been experimenting with this as of this quarter is like, when you have something that’s big and kind of abstract enough, like, you know, I want us to go from this MRR to this MRR.

Well, there’s a lot of ways to get there. And so that’s where I find kind of doing like a second tier of like, okay, we’ll support. And we just hired a success team. Like what, what contribution can the success team make towards this school? Like what can you do to help us reach this goal? So you kind of have this like cascading effect and that’s where the idea of like, well, what, how much money or money would we make if we got the adoption of this add on from 30% to 50% and we could come up with other ideas too, but that’s probably big enough, you know, as far as from a goal standpoint, you know, development team, well, what can you do to help us hit this revenue goal?

Then I think that’s like the hardest department to put a, you know, a number on, but yeah, That requires us to have a lot of discipline around when customers are asking for a feature… we need to estimate the value of everything, and at least we try to, and I don’t know that we do a great job, but…

We know that we have one thing that hopefully we’ll be launching soon and we’ve done the math. And we think it’s worth about 2000 in MRR between current customers that are kind of working around what we have now and then future customers. And then, you know, kind of a rough estimation of like what, what it might be useful, what use that might be made to another team.

So we can say, okay, cool. Well, you know, maybe, you know, the development team, they’re responsible for generating 5K in MRR over this quarter. And then we can kind of track like, oh, well we prevented this customer from churning or, you know, whatever the case is, we’ll see how that goes. Everybody else is a little bit more discreet like marketing.

You are top of the funnel focused. I want you to increase top of funnel by 5% month over month. And we can show that and we track marketing all the way up to like a PQL stage, which is basically where sales picks up. There is overlap, but goes from a PQL all the way through to close.

So that’s kind of how we’ve been setting it up, but we’re still very, you know, I’ve been with Bare metrics for like, like eight or nine months. And one of those months I was in Texas during the freeze where we had no power or water and, you know, everybody caught COVID and that sort of stuff too.

It’s been a relatively short period of time. I think that that’s kind of like the high level structure. I think in about two months from now, I’ll have a picture of how good of a setup that was and how, and that’s definitely something to your point, I’ll look at it.

It’s like, well, how do people feel empowered? Like it was this something, was this a goal that people felt like they could contribute to? Did it make sense to them? Did they know when to ask for help that it caused good interaction between teams? Did we pit teams against each other? Did the marketing team and sales team, did they become, you know, bitter enemies or did that actually Did that have the sales team like, oh, we just had this great sales call. And as soon as I showed them this feature, their eyes lit up. So they might want to tell the marketing team. That’s like, Hey, find me more people that are looking for this thing. So we’ll see if that happens or not. But that’s kind of my, that’s kind of my goal at the end of the quarter.

Craig Hewitt: Got it. One thing that you describe that made me think is that a big kind of litmus test for us has been when we rolled these out. And we say to the leaders of, of a group, this is your thing. If they start squirming in their chair, that’s a bad sign to me, right? That this is not the right person in this role.

And, and I think it can, like you said, cascade down there to where like the success team can say to the individual members, okay, this is our thing, you know, I need you all to be on board and, and we all need to be accountable for this thing. If then, you know, the individual customer support rep says like, you know, whatever. No, that’s not my problem. Just here to answer tickets. Like that’s a bad sign. 

So like, I think that again, going back to like values and screening against those things, you know, people being comfortable with the level of ownership that we’re giving them is, is a big indicator of their success with us.

Brian Sierakowski: Yeah. I totally agree. And I think it’s sort of interesting because you’re the one setting the goals, but you’re not, you’re delegating it. You’re telling someone else to do it. So it’s almost like when I see the person squirm, when I give the goal, you know, there’s a part for me too, where I’m like, yeah, I get it.

I just gave you a really big goal and, you know, asking you to maybe double your effective output from last month or last, last quarter. You have three months to get twice as good at what you’re doing. So, yeah, I don’t know. I find myself in that position to where I don’t…. 

You can cross reference my teammates, but maybe like, I, I think I look very stoic and like, I’m like, yes, yes. This is the path. headed towards the stars and, you know, inside, I’m kind of like, you know, nervously sweating about the path that I have out ahead and say like, yeah, I get it.

And there’s a lot for us to figure out to hit our goals. But the alternative is what, like, we just do the same stuff over and over again? We don’t make any progress? That doesn’t sound like any fun. 

Craig Hewitt: Yup. And really, they should see you working just as hard as everyone else. And so I think that’s the thing that allows us to say this with a straight face.

Brian Sierakowski: Totally. It’s something I check myself on all the time, maybe too much, but it’s like, yeah, like, Hey, am I putting, you know, both the time and the effort in am I focused in the right places? 

Like, did I spend the whole day on Twitter? That’s a really bad sign for me. Like oh, well, you know, I wanted to do something that felt like work and, you know, kind of has an inbox type feel to it.

But yeah, I think like, keeping yourself honest with that is, is really because your point, you know, you’re, you’re delivering these goals and these objectives and you need to make sure that you’re not squirming first. If you’re squirming, you know, it’s like everybody else on the team, that’s going to be like, well, he knew this goal was not achievable.

Like, you know, look at him. He’s like, you know, he’s hiding under his desk. He’s not even on screen when he’s telling us about it. Like, clearly this is not, this is not a, you know, a real goal. We can’t, we don’t have to, we don’t have to take this seriously. Yeah, absolutely. The one other thing that I’ll say in that.

Before we run out of time here. I want to talk to you a little bit more about, you know, kind of the transition period for you. One other thing that I found that’s really useful is like, when you set that goal, probably something you already do, but we do department meetings once a week. And I’m really pushing, even though it’s a new thing, I’m like, all right, before we get into anything else that we’ve done for the week, how are we doing towards our goal?

And like, hopefully we’ve, we’ve delivered a quantifiable goal that we can report against, but I find it’s really interesting like, okay, here’s like, ah, we didn’t make any progress towards our goal this week. And then here’s everything we did. And it’s like, oh, none of that stuff that we did really could even logically contribute to the goal that we set.

And so I think it’s just like, almost without you even having to say it, say anything, it’s like, yeah. Oh, right. Like we didn’t make any progress on our goal. We’re aware of that. And we also didn’t do anything to make progress on our goal. Maybe next week we should not do that. Maybe we should maybe, you know, and it’s really hard, especially.

I think the biggest transition for us, it’s going from the team members handling so much and having so many different things thrown at them to really get into a place of focus. It’s like, okay, well, we can’t, if we want to sell this add on, then we’re not doing feature training or we’re not developing an, you know, a video series or we’re not, you know, we’re focusing on this one goal and anything that will contribute to that.

That’s what we need to focus on. But it’s really easy, you know, at our size company to think there’s an endless, literally an endless amount of things that you could do. So really almost like, it’s almost like you’re taking the pressure off of them and like, Hey, this is the only number I’m looking at. So you feel comfortable going for this goal and focusing on it a hundred percent, because this is where this is where we want to see success.

Craig Hewitt: I mean, this is the part that we’re just getting into. Yeah. And it’s super hard. I mean, there’s customers asking for this thing and we, as, you know, people that use the product all the time, want this thing, and we want to deliver chat, support to customers instead of just email and all these things.

And it’s really hard to say no to yourself, to all of these things every day. And I’m terrible at it. And, but again, like we’re talking about this as a spectrum, you know, like I’m proud of us for having the goals, checking in on the goals every week. Just like you’re saying both in our team meeting and individual like groups, we, we check in against the goal and, and I think the next phase, you know, or the next step in the process is really being diligent about not doing nothing but the goal, but making very sure that the goal is taken care.

Um, and we have the people and the resources and the focus towards it. And if we have extra of anything else, then, then we can do this other thing. That’s not the goal, but yeah, we’re not there yet. 

Brian Sierakowski: Yeah, for sure. It’s kind of like the no assholes thing from earlier of, like, it sounds like really easy and really obvious to give the advice of like, you know, focus on the goal and say no to everything else, but in practice, like all that other stuff, it’s like, it doesn’t feel like a distraction in the moment.

It feels like, oh, this’ll be really useful. Like this is going to be really great. Or like, you know, not to harp on like the success team. I feel like the success teams always interacting with customers and like, oh, well, you know, we could just create a video series around this or we could, you know, create a product tour or we could, you know, do whatever, like in like, wow, this could really, it’s not just like a fun, cool thing to do.

It’s like this could really improve our conversion rate, you know, the actual benefits to the business. And so those are the ones that are very difficult to say, like, Don’t worry about that right now, because you know, they might bring it up to me and be like, yeah, I think that can improve our conversion rate, but, you know, whatever, we improve it by 5%.

And it’s pretty difficult from a leadership perspective to be like, no, we don’t, you know, we don’t want on the list. We don’t need, we don’t need more customers. What we need is this other thing that I said, you know, a month and a half ago, that’s what we need. But I do feel like that’s the level of focus.

That’s where it gets hard, but it does feel like, and I don’t know, like again, that’s where I’m very early on in this too. You might talk to me in, you know, three or four months and I might say, yeah, no, that was everything I said that was bad. I don’t do whoo boy. That was really awful.

Early indications…  those are the difficult decisions are the ones that are going to yield. And then eventually people come around and they, you know, we start seeing eye to eye and we’re speaking the same language. And then the, everybody has alignment of like, okay, cool. I can just, you build that, that new habit, that new muscle memory of like, yeah, well we just don’t work on stuff outside the goal.

And then everything gets a little bit easier. 

Craig Hewitt: I don’t have an answer for this, but I have noticed that the kind of whip lashing that we did in our early years as team members of today, this is the thing. And tomorrow, literally today, and then tomorrow, this is the thing that is exhausting, you know, and, and giving people the calmness of saying, Hey, for this period of time, or at least I’m going to declare, you know, that this is the thing for the quarter and it might change.

But you do have a degree of certainty that this is the big thing we’re going to focus on for the quarter, it gives them some, some kind of peace at work. I think. And the other thing is like, you’ve probably seen this over and over too, if there is never the, Hey this’ll take me a half a day and it’ll improve our conversion rate by 5%.

Right. It ends up being a three week thing that is two developers and a designer. And then like, it just like, it’s never that easy is like, I mean, it’s just, there is never like one of our, one of our developers said, if you ever talked to an integration partner and they tell you, it’ll take a day, tell them to fuck off.

Don’t even have a discussion because like, nothing is that easy. And like, we don’t want to be this, this big behemoth, but like everything takes time and everything takes focus. And when you add this other thing, then you’re inherently taking away from something else. Yeah. Yeah. And not to get too esoteric, but I do feel like there is that, you know, when you have the…

There is this kind of psychological aspect of when you have a really difficult email to write, or you’re doing something that’s challenging, both challenging and consequential, like, oh, I need to write up this contract for this customer and I really have to get it right. You know, there is that tendency to like, well, let’s just go pop over to Twitter real quick.

Cause that’s there or whatever, you know, not that not to beat up on Twitter, but like, it’s like, what’s an easy thing to do that can kind of give me kind of a quick gratification and feels like I’m doing something, but I’m not actually doing anything. And I think there’s the same thing of like, when you set a quarterly goal, like within the first, you know, one to three weeks, you’ve already done everything.

That’s kind of easy. It’s like, okay, well let’s just email all of our customers and tell them about this, Adam. And then you’re going to get some success from that, but probably not as much as you want. 

And then there’s going to be that inclination of like, okay, well maybe there’s this other kind of similarly like straightforward thing to do versus it’s like, well, if we want to get complete success in towards this goal, We’re going to have to dig in and we’re going to, like, we’re going to have to push to that second level, you know, like the cardio workout where you get to like the second, you know, 30 minutes and they’re like, oh my God, I I’ve, I’m only halfway through.

And it’s like, you know, that last 15 minutes, you know, is more effort than, you know, the entire 45 minutes before it. So I think there is some component of that, of setting the goal and not changing it over the course of the quarter can begin to develop that muscle memory and that expertise of like, yeah, well, like we, we’ve learned that to completely hit the goals that we want, especially if they’re challenging goals.

That’s when we have. That’s when we have to develop the mental capacity to like dig in and really like, it’s going to get hard as I was going to be like, and there, there will be easier. There will be things that will feel like they’re easier and, you know, have more effect because there’s always low-hanging fruit all over the place.

So I think that’s the other important component of like, you will actually, it’ll actually dive in and be like, okay, cool. Well, we’ve already done all the easy stuff to do and we haven’t hit our goal. What’s next? How do we, how do we keep going? How do we either gain more information? Or how do we try something else out?

Or, you know, trying like when all else fails, just try some random shit and throw it out there. Like, eh, I don’t know, like, you know, let’s try and, you know, then you’re going to find some things that are going to hit and you’re going to start making, you know, you’ll hit the initial bump of progress and then there’ll be flat or zero, and then it’ll slowly start ramping back up.

And that’s when you get like, really nice, like network effects from that point for. I don’t want us to run out of time here, but I want to kind of zoom back. I had a little, you know, bookmark in our timeline. So you were, you were just starting and doing a podcast. I’m curious. What did you, what was your process like to you went from kind of nothing to starting.

Like, how did you get your first guests? Like, how did you, how did you even get that initial venture going? 

Craig Hewitt: I got my first couple of guests from a community I was a part of. I talked about Rob Walling and Startups For the Rest of Us. They have, you know, an online community where I connected with a few folks.

And that’s kinda how I got started and then just, you know, other people they knew in other podcasts that existed in this space is kind of how I went. And then the question after you interview somebody is, Hey, who else do you think I should talk to around this topic or in this space? is a really great way to keep getting guests.

Brian Sierakowski: That’s awesome. And then did it kind of just build on itself from there? You kind of like once you got the first couple, maybe were the most challenging and then from there it’s like, oh, well now we have had like what we were just saying. Now we have more ideas of, you know, then I need of who, who I should talk to and who I should go after.

Craig Hewitt: Yeah. I think that the world does open up a fair bit. Back in the day when I started, it was six years ago. Like getting people on a podcast was in a lot of ways easier and in some ways harder because a lot of people hadn’t heard of a podcast, but, there certainly was less competition for people’s airtime.

But yeah, I mean, I think it’s kind of just like, you try to be aspirational a bit like, who do I want to get on to, to connect with and network with who do I want to learn from and who do I think would have an interesting story to tell. And like, if someone ticks any of those boxes, then for me, they’re a good guest.

Brian Sierakowski: Awesome. And then how did you go from that phase? Like at what point did you realize like, Hey, this process of doing all this stuff, like without software kind of sucks, like how did you, how did you make that shift? And when did that happen? 

Craig Hewitt: That shift to like Podcast Motor as a business happens really quick.

Like in the first couple of weeks, their first couple of episodes, I should say, you know, first couple weeks, you know, kind of said, I’m doing all this stuff. This is a hassle, but I’m getting pretty decent at it should reach out to a few podcasts, as I know and see if they’d be interested.

And I did. And they were, so I put up a website and looked up Stripe to Gravity Form or something like that, and was away and had some paying customers. And then that kind of compounded and compounded. And then through one of our customers we actually got introduced to the person that had written the WordPress plugin that we ended up acquiring.

It’s a WordPress plugin in the podcasting space. And that’s how Casto says the hosting platform got started. As we acquired this WordPress plugin called Seriously Simple Podcasting and, you know, built the hosting platform to connect to it. And we’ve kind of gone from there. 

Brian Sierakowski:That’s awesome. How long were you in that phase of kind of still working and also, you know, in that in-between time of like, I’m not quite full-time yet, but I’m sure.

Spending most, or all of my free time on this project slash company too long, a year and a half. And was that, was that all during the beginning of the podcast, where were you still working another job during that? 

Craig Hewitt: Yeah, I was working my corporate sales job and doing this kind of nights and weekends and stuff and it was terrible. Yeah. I could never do it again. 

Brian Sierakowski: Did you do the acquisition while you were still working a full-time job?

Craig Hewitt: No, that was afterwards. 

Brian Sierakowski: Got it. What was the timeline between then of going full time to engaging in an acquisition? 

Craig Hewitt: It’s about six months. 

Brian Sierakowski: Wow. Okay. That’s pretty quick.

Yeah. Was that, was that just sort of a, a serendipity thing of like, oh, why I know someone who knows this person or were you actively like, yeah, I want to bite off a little bit of a bigger chunk of. 

Craig Hewitt: It was very much serendipitous. Yeah. I mean, just a friend who is also a customer, you know, said, Hey, I know this guy who wrote this plugin and he’s looking to get rid of it. And he introduced us.

And it went from there. Yeah. They knew that I was looking to do something more than just run a podcasting service. So that’s probably why, why we came to mind as a potentially good fit. 

Brian Sierakowski: That sounds like you… You put it on your vision board. 

Craig Hewitt: That’s right.That’s right. Put it out in the world. 

Brian Sierakowski: Yeah, that’s cool. It’s really interesting. I think that, I don’t know if I’ve ever heard of a story of someone who had gone full time with their company and in the first six months gone through an acquisition, did you have any like M and A experience before doing that?

Craig Hewitt: No. And, and, and to be fair, it was not a big deal in terms of like dollar amounts. But no, I had not had any M and A experience since then kind of have gotten the bug and we’ve acquired some other companies and assets and stuff like that. It’s a cool way to grow for sure, or something we have sites on doing more of yeah.

Brian Sierakowski: What advice would you have for people if they’re in a space where, you know, maybe there are appropriately priced assets out there… 

Craig Hewitt: There aren’t much of those these days, in our world (laughs)

Brian Sierakowski: Yeah. It’s interesting. Maybe that’s your advice: probably don’t? 

Craig Hewitt: Yeah. I mean, like for us, like it just made all the sense in the world. It was this tool that was not monetized at all. So it was not very expensive. We saw a very clear path from a product perspective of how to monetize it. And it had like this built in audience of free users that we could convert some of them to paying customers of our hosting service.

The plan was really obvious. Other people in the space had done it already. And so the model was proven. From that perspective, the risk was understood as much as I could understand it. 

I think the place where people get into trouble is like, you look at Tumblr, you know? How many times has Tumblr bounced around? You know, because I think those companies had no idea what to do with it. And it looked like a cool thing and a blogging tool, great Yahoo, and you know, now automatic. Well, you know, like automatics is a great company and is one of our investors, like, what the heck are they doing with tumblr?

Right? Like they have a really good logging system already. Like what? I just don’t. So, that’s just like, one thing I would say is like, have a really good idea of what you’re going to do with this, and then all the stuff about the due diligence and metrics and all of that absolutely has to make sense.

And there’s plenty that’s been written about how to do that, but I think from my perspective, it’s like, do you have an idea of how this thing fits into either your existing business and customer base and, and that whole kind of acquisition funnel? Or can you imagine how you could create that?

Brian Sierakowski: Yeah. Well, that’s really interesting. I’m sort of split because I’ve seen, you know, I seen firsthand a number of acquisitions that have blown up or, uh, ones that, you know, and we’ve all heard the stories of ones that have succeeded. I think, you know, Google’s relatively notorious for buying something and playing with it for a little bit and then shutting it down after the fact.

So on one hand there, there’s certainly the case of like, it’s very dangerous and you really have to like, have a really clear thesis when you buy something, you kind of have to, like, you kind of have to like, know something that they don’t, or like, to your point, like, well, they just never spent any time or effort or had no interest in getting people to pay for this plugin.

It’s like, okay, well we have the capability to ask people for money for this. It’s directly in the product offering that we have and we could sell it to our existing customers. Although that is something a lot of people say to themselves, and that turns out not to be true.

A lot of times I could probably do a separate, separate power on that. So on one hand, that’s kind of like all like, Hey, like don’t, don’t do this. Like don’t, don’t do acquisitions. It’s time-consuming, there’s generally a lot of emotion involved like it is something that somebody really loves and they’ve worked on and, you know, probably hasn’t quite gone the way that they want it to go.

So you have to be really thoughtful and really present for that while you’re also running the rest of your company. So that’s all like, don’t do it. But then on the other hand, I can’t help but imagine it’s like, especially with like microacquire existing now of like just having like, you know, a monthly or quarterly search on microacquire, like, Hey, is there any sort of like value added plugin that would make sense for us?

I, you know, maybe this is a quick way for us to increase, you know, like how easy is it to get like a 10% MRR increase? Like that’s pretty hard. So if you can do it through an acquisition and, you know, even make some bit of sense, then maybe it’s worth it, maybe it’s worth checking out. I think it’s really interesting and something I’ve just literally never thought about before, but maybe that is a way to go.

Or maybe that’s a good way to like, provide advice that drives a lot of otherwise very good companies into the ground. Like, oh yeah, like we were going great. But then we did this acquisition that called us to pause for six months on what we were doing. And then it fell apart and it was, you know, expensive and legal fees.

And then we went out of business. 

Craig Hewitt: I think both, both are very true, right? They’re always more complicated. They take more time and resources and focus, you know, away from, from your other priorities. But if it works right, then it’s a great opportunity to have inorganic growth, if everything lines up.

And if you have the capacity, you know, financial and people, focus to spare, then, then it’s a really good thing. But I think it’s harder to get a really good fit then we all tell ourselves. Yeah, 

Brian Sierakowski: Maybe it’s impossible. I’m trying to, like, it’s funny to like, listen to myself, I’m going back and forth between like, there’s no way this could ever work or maybe it’s the best idea I’ve ever heard.

On the line between those two. 

Craig Hewitt: Well I guess the truth is probably somewhere in between, and this is not, this is not financial advice. This is not a financial planner or yeah. Anything of that nature. 

Brian Sierakowski: This has been awesome. We’ve been chatting for quite a long time now. I just want to bring us in for a soft landing here. 

I’d love to just give you a minute to talk about where you’re at today with the business and what you have going on. And then also, if there’s anything you want to draw anybody’s attention to, you know, you mentioned the podcast and it seems like you are quite fluent in the world of podcasting.

So let’s give you a little chance to like, you know, give a little quick update. 

Craig Hewitt: Well, first of all, it’s really, really a great discussion. I do a lot of podcasting. This is a really, really cool chat. So, thank you very much for having me. If folks want to want to check out what we’re doing at Casos we’re at C A S T O S you know, one of the big focuses for us and kind of emerging area of podcasting is private podcasting us to think about like membership site for podcasting charge money, and, you know, hook it up to your, your online course or membership site or, or SAS app to, to offer like more of a personalized podcasting experience to a select group.

It’s a lot of our focus right now. And folks, you know, want to learn more about podcasting. You can Google it with our name and you’ll see a bunch of blog posts that we’ve written on it that maybe we could include in the show notes here. But yeah, I mean, we would love to connect with anybody.

If you have any questions at all, you know, shoot us a message, And I would love to talk about podcasting with anybody who’s interested in it. Hasn’t kind of taken the dive yet. 

Brian Sierakowski: Awesome. That’s great, Craig. Yeah. I love that. I love the private podcasts. Send it out to a membership community or your customers of your app have a private, you know, customers only podcasts or something like that.

That’s just such a, such a great idea and helps bridge the gap a little bit of how do you make money off of these things? I feel like you would have loved to have had in the early days too. 

Craig Hewitt: Yeah, absolutely. 

Brian Sierakowski: Awesome Craig. Well, yeah, thanks so much for joining us and thanks everybody for listening.

We will have all the, all the links and all the, the resources mentioned today in the, in the description and yeah. Thanks again, Craig. 

Craig Hewitt: Thanks, Brian. Have a good one. 

Brian Sierakowski: That was our conversation with Craig Hewitt, founder of Castos. If you’re looking for a little bit of help with your podcast, or maybe you’re looking to launch a private podcast, you know where to go. That’s Castos C A S T O

If it’s SaaS analytics, you’re looking for, check us out Hope you enjoyed the episode and invite you to check out our other Founder Chats. If you’re able to leave a review or share with a friend, it goes a long way. Thanks for listening. If it’s a SAS analytics tool that you’re looking for, well, then you can check us

I hope you enjoyed this episode. We invite you to check out our other founder chats. If you’re able to share with a friend or leave a review, it goes a long way. Thanks for listening.

Brian Sierakowski

Brian Sierakowski is the former General Manager of Baremetrics, an analytics and engagement tool for SaaS and subscription businesses. Before leading Baremetrics, Brian built TeamPassword, a password-sharing app that was acquired by Jungle Disk in 2018.