Sharing Our Fails (& Wins) with Craig Hewitt

Sharing Our Fails (& Wins) w/ Craig Hewitt (1)

Brian Casel : [00:00:00] Hey, it's Open Threads. It's my podcast. I'm Brian Casel. Welcome to it. Today I'm talking to my buddy Craig Hewitt. He is the founder of Castos. They are a podcast hosting company. They also offer Castos Productions, which is podcast editing service. I've been a longtime customer of both of their services for many years, and a long time fan of Craig as a founder.

And he's built a pretty impressive company. We talked a bit about that, of course, but really in this episode, We wanted to talk about failing, what it's like to fail, why building a business, especially this type of software startup business only gets harder. It actually doesn't get easier.

And how can we actually share our fails publicly? You know, Craig, like me we've both been podcasting and doing this quote unquote build in public thing for a long time. And you know, I think this is a running [00:01:00] theme on this podcast where, You know, we're pretty wary of sharing too many wins in public.

I think we're overweighted on the the highlight reel side of things. so Craig and I are both interested and Craig is actively doing some of this with a new project that he'll tell you about. Maybe folks like us can be a little bit more transparent about the real struggles, the real challenges, and the mistakes that we're making in real time by sharing them publicly so that folks who are just a few years behind us can benefit.

I think that's, I think that's a really good thing. And we unpack what it means to get into all that. As always, today's episode is brought to you by ZipMessage. That's my product. It's for async messaging with your team, with your customers, with your clients. I'll tell you a thing or two about that later in the show.

For now, let's talk failing with Craig. See ya.

Craig Hewitt, welcome to uh, Open Threads. How you doing?

Craig Hewitt: Hey, Brian. Good man. Thanks for having me.[00:02:00]

Brian Casel : Great to finally connect cuz you, you and I have known each other for a long time now, and I'm trying to remember, I don't know if we've ever actually been on a podcast together, which is kind of crazy.

Craig Hewitt: Yeah, it's been a hot minute. I think you've been on Rogue Startups, but it's been...

Brian Casel : Yes, that's right.

Craig Hewitt: - an embarrassingly long amount... Like three or four years. Like it's terrible. Yeah.

Brian Casel : Yeah. Yeah. Well, I, I've always been a fan of everything that you do. I've been a long time customer of Casto s both as the podcast hosting side and you guys do all the editing and production for my other podcast, Bootstrapped Web, and I think we were probably one of your very first clients on that.

So, yeah great stuff over there. Lot of stuff to to dive into. And by the way, like I've, you know, you are a great podcaster. I've been lately actually really getting into following Seeking Scale. You know, that's a, that's another one of these really good, like bootstrapper behind the scenes kind of podcasts.

Craig Hewitt: Yeah, that, that one's fun. So I do a Seeking Scale with Andy Baldacci. Andy's like, marketing, non-technical founder. Kinda like [00:03:00] you used to be but but like me. And, And yeah. I mean, we talk about, we're at similar spots in our business, which is cool. Like, you know how and the whole kind of premise is, you know, zero to one, there's a lot out there and then like, you know one to five kind of how do you how do you do that?

And it's fucking hard. I mean, sorry, I don't know if I can cuss, but like,

Brian Casel : Cuss away man.

Craig Hewitt: Think, I think we'll both tell you like, nothing is easier at decent scale to, to really good scale where we're going. And I think that's, that's a misconception. You know, everybody thinks, Oh, when I get uh, you know, a million ARR. a hundred thousand dollars a month or whatever that like, everything's sunshine, rainbows, and it's basically just all still really hard. so it's been interesting.

Brian Casel : Well, that, that's like a perfect segue into what I actually wanna talk to you about .We, we were chatting a bit about this beforehand. I think the theme of this episode here, this first one is gonna be about failing and sharing fails publicly. And basically just talking about how hard it is to build a company like this, especially a SaaS..

And, you know, I was [00:04:00] actually, last week I was hanging out with a bunch of our mutual friends, at, a little trip that we call NoSnowTinyConf out in Colorado. And. You know, you you just mentioned how like, it doesn't get any easier as, as you grow, as the company grows and you go year to year. And, and actually a question I was asking a lot of my friends there, and I love to ask this sort of question in general is like, looking back on your current company, can you point to a time that was hard? Like what was the hardest phase of the company? You know?

I mean I've been through different phases across different businesses and I'm sort of back to the beginning phase of new startup with, ZipMessage. Most of my circle of friends, including you, are are several years into it. You know, grew a bit further, you know, much, much further past where I'm at right now. So I like to sort of share notes like that and just hear about like, is it actually harder now or was it harder in like the, you know, when you're around the 10K MRR range or... Yeah, how do you think about that?

Craig Hewitt: Yeah. So I think there's like one thing that's important to establish, and I think it's really interesting [00:05:00] listening to you and Jordan talk on Bootstrapped Web because there's where you are in your business and where you are as a founder and they're not the same thing. You know like I think you and I and you and Jordan are at the same kind of place as like founders in our capacity, right? To run a business. Even though our businesses are in really different places. And so I think that like, that's, that's not the same thing. Like your MRR is not your kind of capacity as a founder, and that's like good for everyone. you know you personally

Brian Casel : Something I constantly have to remind myself.

Craig Hewitt: Yeah. Yeah A And then I think that, like, aside from that, like to answer your question, I think that like, I have been very fortunate, both with Podcast Motor before and now with Castos, to not have to struggle to get initial product market fit. You know, like you were our first customer at Podcast Motor and we still have our third customer. I think it's, we just, like, we had product market fit right out the door. It evolved a lot. It's still evolving. Castos' the same way. We had customers literally on the first day and we were at 10,000 MRR, like less than a [00:06:00] year later. And so like, I never had to struggle with that. And I think if I did a hundred percent, that would be the biggest challenge because you're working and you're working and you're working and you're at, you know, whatever, not huge growth right off the bat. And you're asking yourself like, What am I doing? What am I missing? Do I have to pivot? And, and I know like you you know, a lot of people ask themselves these questions and, and like, I think that would be really hard.

For me, I think where I am right now is the hardest, because if you grow bootstrapped it's just really predictable and really slow. We raised a little bit of money joining TinySeed. We raised a little more money about a year ago, year and a half ago. And we're coming out of that funded phase, even mildly funded you know we didn't raise a whole ton of money, to having to be self-sufficient, bootstrapped.

And that like landing is super challenging, especially like in a shitty economy, you know, [00:07:00] where nothing is predictable. Raising more money is not an option for most people. And a lot of customers are saying like, Hey, I don't know what's coming around the corner, I'm less likely to buy than before. And so everybody you talk to says like, nothing is going well right now. And, and us trying to make this kind of soft landing. Right now is just hard because we think we know where it's going and I have a lot of confidence in it, but I don't know. You know, that's just really, it's really stressful. And it's, it's a hundred percent like... the challenge of funding, I think is like, you can either be funded and keep raising more money. And the goal of raising money is to get to the next funding round. And I think there's nothing wrong with that it's just a totally different kind of business. And there's being totally bootstrapped where everything is predictable and you're just funding your way. And there's this in between. And the, I think the problem with in between is you're switching, you know, you start bootstrapped and then you have some funding, and then you have to switch back to being bootstrapped at some point. And that's just a, like a mindset shift.

Brian Casel : It's interesting because you you and I share a unique thing in our in [00:08:00] our path through different businesses in that you and I both had a productized service business and then shifted to SaaS. And you still run, you know the productized service side of of Castos And I had Audience Ops and then later sold that. But you know and and there another sort of running theme with a lot of the people that I'm talking to on this show is I'm talking to a lot of founders who've who've been through multiple businesses and exits and started again. And you know, one thing that I've definitely experienced, and it seems to be apparent with a lot of others too, is that like, just because it's not your first rodeo it it doesn't necessarily get easier in, in a lot of ways it can be harder.

I mean, you know, you were talking about how Castos productions it was previously called Podcast Motor. You know it, got customers product market fit right away. And I definitely experienced the same thing with Audience Ops back in 2015 when I... I mean it crossed 10K MRR in like less than three months.

Like, it was like a really fast revenue growth sort of business. And like first year it was like, totally [00:09:00] clear, totally even surpassed my expectations. Like this is gonna be a solid business that I could just run for a little while And then I've had like three SaaS attempts since then , which have not grown nearly as fast I mean they they did surpass in terms of like number of customers. And you know ZipMessage has done better than the previous ones but like it, it is definitely a lot more challenging you know and totally different business model and all that. So um yeah. what you also just said about bootstrapped to funding I find it's the mentality of switching between those things right. The vast majority of my business career has been completely bootstrapped. The beginning of of ZipMessage in the last several years has been self-funded through profits from from Audience Ops And then like you, I switched to, you know, fund strapping or or like a tiny bit of funding to sustain the the initial runway.

And it took me a little while to like wrap my head around like, Oh, I'm supposed to spend this money. I'm not supposed [00:10:00] to just look at it in the bank and hope..., you know cuz I think at first it was sort of like Oh this is just a runway material to add like a safety net But then at a certain point it was like, I need to deploy this and spend more I'm I'm curious how how you've sort of navigated between the bootstrapper mentality and actually having cash to spend ahead of profitability. That's a whole new game

Craig Hewitt: Yeah, So, so it wasn't hard at all for me to spend the money,

Brian Casel : Hmm

Craig Hewitt: Yeah I I mean, probably the opposite, right? Like probably spent more too quickly than than I should've. But I mean, for me it is, if you take investment, you need to spend it. And, and I think you need to spend it as quickly as you can to where it's smart that's really hard and subjective.

But like, if there's an opportunity to hire salespeople like we did, or bring on a marketing person or run PPC or whatever, there's no sense waiting three or six or 12 months to do that because the market changes and your business needs are different and all this kinda stuff. for me, if you raise [00:11:00] money and you have a need, spend the money right now, because it could pay off hugely and you could just have more money to spend down the road.

So like that, that's how we approached it. And, and for the most part, like it's worked out, but I think that. There's a lot of people I know like in the TinySeed group, that that money's still just sitting in their accounting and there's still a one or two person shop and, and it's just like, Dude, what, what are you doing? Like, why did you do this? You know, if, I mean, you joined for the community and the support or something like that, that, that's cool, but like to give up a chunk of your company and equity, and I don't know how, you know, Comm does their, does their agreements but like, you're giving up a decent chunk of your company and like, if you don't take advantage of the things you get for that, and a lot of that is money, then you shouldn't have done it, I think.

Brian Casel : Yeah. On TinySeed and Comm Fund which is what I uh joined The community and the mentorship and the other support aspects are nice but I wouldn't have taken the money just for that. I, it was definitely a financial decision for sure You know. And and so it it [00:12:00] took me like about eight to 10 months of frankly not spending aggressively enough to get to a point where I started to understand we do need to spend now and spend more than than I've historically spent, like more aggressively faster on people, and spend on marketing, spend and things like that. What I believe that that buys is like you're you're essentially buying your way to faster revenue growth. And once you get there, hopefully quickly enough, that is what ultimately extends your runway to a sustainable path. It's you know cuz if you don't then you're literally just have a date on the calendar when you're going to run outta money, you know?

That's what sort of clicked in my mind was like, be more aggressive for at least a year to two years ahead of profitability. To get the revenue to a point where, okay, now we're at break even and now we can figure out how much we wanna reinvest and where we go from there.

You know, you're at a much better position once you grow the revenue.

Craig Hewitt: Yep. Absolutely I I think of it as like living in the future.

Brian Casel : Yeah you know you you've been again you've been podcasting for many years [00:13:00] especially in these uh bootstrapper formatted podcasts where I I always think it's funny how it like folks like us like to tune into stuff like that, but most of the internet is not interested at all. But to us it's like the best type of show there is you know because we're being transparent about what what we're working on and the real challenges behind the scenes and you know, just telling the story ongoing

So, you know, what you and I were chatting about before, before we hit record on this, is sharing fails sharing the the transparency I mean Talk to me about that Like what what's been on your mind there Cuz you know I do think that our circles and our industry, our little software startup industry, sort of, it does suffer a little bit from just seeing too much of the highlight reel of the wins from everyone, which can be helpful, can be inspiring. You can learn lessons from what worked for someone else. Maybe you could take a lesson and apply in your case. But I always find that that what's more educational for me is trying [00:14:00] something and failing at it and learning the hard way so yeah What what do you what do you see in there?

Craig Hewitt: Yeah, I mean, I, I think that running, you know Rogue Startups and now Seeking Scale I've been doing it for seven years. It's amazing right? Like it's it's just a long time. And in that time, I mean, I never have been the one to talk about MRR and all these kinds of things, like super openly. but, But try to abstract away like the lessons I'm learning so that they're one, just not super personal, but also so that everyone else can kind of like benefit from like how it applies to their business. And just like really honestly, like I basically only share the good stuff , you know, and I think that you probably do too, and Jordan probably does too and Dave does too on Rogue Startups. Because it sucks to tell people that you had to lay team members off or that you didn't get funding or that you don't have product market fit and are struggling to get traction and and like, I think that it's natural, [00:15:00] right?

For us, like we do these podcasts because we enjoy talking to our cohosts and that we hope we provide value to like the community that has given so much back to us. I mean, I think that's really , where my like podcasting comes from at this point is just like, people like Josh Pigford and the folks from Buffer are just so transparent and open and have shared so much about what they know that I've benefited so much from that if I can do some or some version of that, then that's super helpful.

But it's really disingenuous for me only to talk about the good stuff you know and I say that, and at the same time, I don't know that I can share a whole lot of really bad stuff because that's just not cool. That's just not cool. And so, like, I sent you a a message the other day that I have this idea for a place where people can share their fails, you know? and I I should have it better fleshed out as we're talking about it on this podcast, but by the time this goes out, so go to, right? Whale, like the mammal, right? [00:16:00] And I want it to be a place where people can share the bad things they've learned, right Like Startups, For the Rest of Us used to have the tagline of like, sharing our experiences to help you avoid the same mistakes we made right. And that's really like the essence of what, of I think this could be is not just the good right, but only the bad, basically because all of the good is everything out there in entre porn land, on Twitter And uh, and I think there should be like a safe place to, to do the rest. And so whether that's like anonymized or not, or you kind of, again, like abstract away the lesson you learn so that it doesn't totally, you know, defame you and in your business and, and cast a person in the wrong light, like whatever.

Brian Casel : I was gonna say that when you first you know, sent me the link and sent me the concept a couple weeks ago that was actually my first thought was like, it, is it anonymized? Cuz I think that is an interesting angle you know, because it is really difficult to share fails like you said And it's [00:17:00] it's not even so much because like I'm necessarily ashamed of it, or I mean, I guess there's probably part of...

Craig Hewitt: yeah.

Brian Casel : But there but but a lot of the fails are just sensitive information that like, technically we can't share. So it, it might be about like firing someone or it might be about I don't know, like maybe something went really wrong that that does affect customers and customers might be listening or something like that. You know, like you just don't -

Craig Hewitt: Or team members, right? Like I, I think a

Brian Casel : yeah Or or something that, that we, that might not even happen, but it's a problem and those team members might be listening. So there's all sorts of ways that like, you just don't want certain information to be out there but if there is some way to let other founders in on what actually goes on and the nuances of these challenges and how we think about them and how we deal with them.

You know as you know I I go to these tiny conferences two three times a year with with a lot of our mutual friends, and that's where the real stuff comes out, we're we're hanging out we're going snowboarding We're doing [00:18:00] sessions in a house. It's totally private. We've known each other for years. We're not sharing it on Twitter right. So that's that's where the real support stuff comes out. But there is a broader community here online that should benefit from it.

And so here's like a random thought, I don't know where you're gonna take Fail Whale, but like, if there's some way to, to make it anonymous, but still share enough information about the company, you know so like think like like MicroAcquire where they don't reveal the name of the company on the listing, but they reveal enough about it like the the revenue level and the and the industry that you're in and stuff like that you know to give you some context

Craig Hewitt: Yeah, yeah. And so I, I, I don't know, I don't know where it's gonna go If, Yeah, I guess folks who are listening, if it's interesting, like hit me up on Twitter dms, @thecraighewitt on Twitter yeah, I'd love to just hear about it because I think that it it doesn't make any sense for me to just share like what I'm learning the bad stuff that I'm learning. But if everybody, or a lot of people, could share across a wide range of types of experiences and levels [00:19:00] of, you know, kind of company size and that kind of stuff. Like it it would be really interesting.

I mean, I'll just share like the handful of just really broad things that I wanna write about, but am just scared shitless about like, one, like having to lay people off. That's terrible. Right. Had to do it. It's terrible. Never, ever, ever wanna do it again. a couple of really big, like, developer mess ups, right? Like canceling everyone's plan , you know, on the live database, like things like that. you know, wasting a bunch of money on, on marketing, our sales efforts that probably didn't do enough due diligence and planning on, like. I have so many and I think everybody does too. It's like probably nodding your head listening to this thing. Yeah, I could, I could write the same, you know, three or four blog posts.

And, and I think that's just the, the point is like, Twitter and blog posts and podcasts are just full of the good stuff. And it's just not helpful because I think especially for like the, people who have been here and [00:20:00] doing it, as long as you and I have see that, and they're just like, Oh, I, I heard this one thing that someone said and know, there's a lot more badness behind that. You know? I know you said, Oh, we had a rough patch, and that means you're shitting the bed and you you have to fire people and you don't know if you're gonna make it.

But a new entrepreneur who is just starting out, hears that and says, Oh, this SaaS stuff is so easy. I just like cobble together some rails and get some customers and write some blog posts and it's all great. And it's not like, it's really f and hard and like, that's where I think that these kind of podcasts and, and I run one too, right? So two, you know, so like, I'm, I'm as guilty as everyone else, but like, This kind of content is dangerous to some people, and, and I think that like striking that balance is pretty important.

Brian Casel : Yeah, absolutely. I mean think you're totally right that the more experience that you gain and and the further along your company goes it's almost like you don't know what you don't even know, people starting out have no idea what kinds of [00:21:00] challenges are going to arise. And and you're right they can be a lot harder and a lot worse. And I know there's plenty that I haven't even run up into yet You know and I and I think it's you know folks who listen to Bootstrapped Web or Seeking Scale think if if they're sort of like in our quote unquote generation, our age, and and been around this game a bit like you could probably tell the ballpark of what the challenges are that that we might be talking about and dancing around but not saying specifically. But you're right like there's a lot of younger folks and that's how I generally think about building in public and sharing and going all the way back to my blogging days and email and Twitter and podcasting I'm always thinking about like I'm speaking to myself from three years ago five years ago you know I'm speaking to a version of myself where where I just did not run up into these things yet. And if if I could share that knowledge that cuz that's how I've always learned is by following folks and and following their their story and seeing you know the different paths that people took [00:22:00] and then seeing myself in those paths like you know

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Okay, back to the show.

I I wonder how you think about fails though, cuz I, I've been asked that question a lot like on podcasts and stuff they're like, you know, if you could do some this or that over again, or, what were the biggest mistakes that you've made in your career? And I, I always have a hard time with that question because looking back, I could point to a lot of stuff, but at the same time I I wouldn't have gotten to where I am now had I not made a bunch of those mistakes.

Craig Hewitt: Yeah.

Brian Casel : And also, like, at the time, looking back, maybe it was the, this was, that was the wrong decision. But like, at the time, given this, the data that I had in front of [00:24:00] me I think I probably made the right decision. It just turned out to be wrong later. but I didn't have the the necessary insight at the time.

Craig Hewitt: Yeah. Yeah. I mean, I think that, I I have two things that, that this brings to mind. I I mostly agree with what you're saying, like you have to have the bumps and the bruises to form who you are and your, you know, character you know, but, but also like knowledge and, and capacity. I think that, one thing I really am missing, this is just me really personally, is like, again, there's a lot of mentorship and content and stuff at the 10 k a month kind of target audience, but there's almost nothing for like one to 5 million And and

I think there's not, because it gets so different so quickly, you know, like you get to 10 k you do the same thing as everyone else basically, and you should be able to get there. But to go from one to 5 million is really different and really nuanced. And so, like right now, that's what I'm struggling the most with. Is like. I need somebody to be able to talk to, really in depth, really share [00:25:00] all the bad things that I'm going through. and, and like I don't find that person. And I've asked a whole bunch, I've asked a lot of really connected people and that they just don't exist, I guess. So anyways, if somebody knows -

Brian Casel : Where do you go for for like advice or or stuff like that? Like know Yeah Between like communities, mastermind groups, coaches What do you look to?

Craig Hewitt: Yeah, I mean, so, so, so we're in a community. You and I are in a community together of, you know, about 20 people. That's one The tiny seed group is probably my best source of, knowledge right now. but What I'm looking for is like, I mean, just really specific, like a paid community, like mastermind plus or minus, like individual coaching only for SaaS founders over a million dollars.

Brian Casel : Mm-hmm

Craig Hewitt: That's not a huge world, but it's not super small either. And like everyone says Dan Martell, Like I, I don't know. Like I, I like Dan. Dan and I are actually talking right now about like working together. but I'm not sure that's exactly right either I think there's a lot of people that are in this boat and, and need this kind of thing. so anyways, that, that's like,

Brian Casel : Mm

Craig Hewitt: That's one. But to, to answer your question, like, I think [00:26:00] really specifically, like if I had one thing to do over again, in my business it is that I wish that we could charge more money

Brian Casel : Mm

Craig Hewitt: Cuz it is such a massive lever. You know, our RPU is $29 and if it was 80, like you can just, you know like Marc from Powered By Search Tweeted the other day. He says like, there's one common thread in high growth companies and its RPU. Totally.

Brian Casel : That's so I totally relate to that. ZipMessage is is in the same challenge right now too And you know like I said looking back on the business that I was able to grow MRR the fastest was by far the one with the highest RPU, you know. Audience Ops was was in the thousands RPU.

And you know there's there's definitely trade offs. I found with process kit that we had a bit higher RPU than than ZipMessage, but it also required more setup and onboarding and and activation Right. And switching costs and stuff like that But we're making a big shift right now with ZipMessage and and the [00:27:00] aim is to increase our RPU And you one of the reasons aside from the customer research and the product market fit kind of stuff I've I've been working on is I have a spreadsheet where I can you know, see the next 12 months of -

Craig Hewitt: Forecast.

Brian Casel : Yeah. Like a forecasting spreadsheet. Right. And I can plug in our current numbers and I can play with if we increase traffic or if we increase conversion rate or if if we increase RPU or if we increase churn rate. You know, how do all these changes impact and far and away every time I run the projection you play with RPU that that gets you to the goal

Craig Hewitt: Yeah. Yep. Joel From Buffer had a really interesting like tweet thread- and talk about like, transparency, they're like the, the poster child for like, transparency. And it was it was the downside of chasing this though. It was, they have always been kind of like this, you know, 20 bucks a month, whatever. And they tried to go after the enterprise and just failed, you know, like product and [00:28:00] marketing and sales and all these decisions you do to try to go after the higher value. customers and it takes you away from your base that got you to a million or 10 million or whatever it is. And And I think we've been guilty of that a little bit, with with some of the stuff we've tried to do around like private podcasting.

Brian Casel : But again, like everything is trade offs, right I mean one thing that I that I notice about ZipMessage, I'm curious if you see this with podcast hosting is that I have been genuinely surprised at how low of a pain the support load has been with ZipMessage. This business has literally more customers, including both paid users and we have thousands of free users on ZipMessage and respondent users to those to our customers We don't get a lot of customer support, like problems like, how to reset my password or like low level we just don't have a high load of that relatively, we're still not at a huge volume, but we're at a much higher volume than any of my previous businesses. And those with much [00:29:00] fewer customers had a much higher support load than we have, you know.

And I think it's like the nature of like we're a lower priced product, which in some ways I think makes it simpler because we're solving a smaller problem that like, part of the goal of moving RPU up is to solve a bigger problem right? Do more. And so it's always a trade off I think as you as you add more complexity you're gonna add more support and and all that kind of stuff.

Craig Hewitt: Yeah, we, we see the same thing. I mean, we have a lot of customers that we've never heard from, you know? I think I think the one the one interesting thing for us there is, you know we have a Word Press plugin, which is how, like the whole business got started is us acquiring the Word Press plugin. And that is where almost all of our support comes from.. Just because WordPress is, you know, a complicated thing with a lot of variables that we don't control a lot of 'em. So that, that's where a lot of our support comes from is, is that integration and people's bonkers WordPress setups and all the million themes and plugins that that can conflict with what we do.

But yeah, I mean, I think that's the model, right, is you can build a bigger [00:30:00] company at a lower price point just by having a lot of customers that are very low friction. Onboarding, paying, being successful, you know all this kind of stuff. A a higher price point a hundred percent needs more actual people being involved. It's just, yeah, trade off.

Brian Casel : Yeah, I mean, just getting back to where we turn to for support, so you and I are in this like private like Slack group and podcast. And and that sort of overlaps with some of the folks that I hang out with two, three times a year on these tiny conferences, like 10 or 12 of us.

So that, that's been really key for me cuz I, I've literally been attending these trips and hanging out with them for going on 10 years now which is pretty amazing That's turned into like an annual mastermind with some interaction throughout the year and then I also have like a a more traditional mastermind group like three other people and and myself we we meet every two weeks.

Those are like the main channels that I turn to when I have like a sticky question that I'm dealing with that I'm probably not gonna talk about publicly but I'll talk to to these people about. One other thing that I'm [00:31:00] that I'm beginning to turn to more is one on one. And and I'm also in Com fund and I do some mentor calls there but I'm I'm not quite as plugged in as I am with with these other groups. I think you and I both do these investor update emails. Once a month. I, and that's just a good exercise in itself like writing up uh the the monthly recap.

And and again, like with going back to those trips, like we each like present a session, like a slide deck of like the a recap of the year and some of the big challenges and and wins and stuff like that So that that's a good exercise. But I also find that like sending the the monthly update email also triggers more one to one advising from from friends. And I find that that can even be even more helpful. So like, my direct responses to my investor update email or like dms with with friends and advisors and you're certainly one of 'em you know like I find that's even more helpful be I think because of the one to one privacy of it. [00:32:00] Cuz I think sometimes in a group setting, the feedback can be influenced Sometimes feedback can be a little bit performative.

Craig Hewitt: mm-hmm.

Brian Casel : Yeah somebody's giving me feedback, but they're also. Performing in front of these other 20 people on on what they're gonna say in response to my thing. You know? Whereas when it's private, I do find that like there's a lot more variance. Like if I ask the same question to five or 10 different people, there's a much wider range and probably more detailed feedback I I find you you know.

Craig Hewitt: Yeah, I, I mean, I, I mostly agree, like on the, the investor update email is amazing, right? Even, you know I I saw Anchor formerly of Teachable is starting a new thing and he's like, I don't have investors, but I'm still sending a monthly email. Like, if, let me know if you wanna be in that. Like, that's amazing. I think everyone should do it. Ed Frayfogel, one of our, you know, friends and investors, turned me onto this like a long time ago, and it's, it's great. It's super helpful. It makes me think critically about, about what we do. And I I agree that like, getting feedback from those folks is good. [00:33:00] The problem I have with it is it's inconsistent. You know, like I'll go three months without hearing from anyone and then, you know one person responds this month and next month one other person might respond and stuff like. So like, yes, it's helpful, but it's totally ad hoc and I think. I think just for me, like, yeah, I mean that thing I'm missing is a person to talk to every two weeks because like, I mean, this sounds conceited, but like I don't do a mastermind because I don't think that many of my friends have a lot to teach me at this point. You know?

Brian Casel : Yep

Craig Hewitt: That sounds really conceited coming outta my mouth but like I wanna learn from the guy who sold for 25 million and that's basically the only person I wanna learn from you know?

Brian Casel : Yeah no I mean I I get it you know And for me, like in, in a lot of these groups that, that we hang out with in person mo most of our mutual friends are way ahead years ahead in business or company level. So I still [00:34:00] get that like future experience

Craig Hewitt: Yeah. And, and it's that but it's also like they have a, like 'n' of one, like they have an experience set of one. Whereas like a professional coach has an experience set of, like, you talk to Rob Walling and he's an investor in 120 companies. Like he has seen so much shit in the last, you know seven or eight years that like his perspective is so much better than any other individual person running a single business. So anyways, that's, kind of a subtle point..

Brian Casel : And and you're right though because it's like if if they don't offer like a paid coaching service, then they're doing it because they're, Or if they're not invested in your company, then they're doing it because they're nice. Maybe they like to talk to you,

Craig Hewitt: Yeah. And that's great.

Brian Casel : Great.

But they don't necessarily have the time to invest every week for a long period of time because that's where you you can really go deep with someone you know Yeah I I totally get it. Well, I think like most episodes here it's it's one of those things where we have way more questions than answers but but we'll come back for another one

Craig Hewitt: Sounds good. [00:35:00] Well, that wraps up today's open thread. Hey, tell me what you think. I'm on Twitter @casjam, and right after that, head over to iTunes and give this show a five star review. Really helps it reach more folks like us. I appreciate it. Talk to you next week.

Sharing Our Fails (& Wins) with Craig Hewitt
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