Episode Transcript
Speaker 1 00:00:08 Welcome to the rogue startups podcast. We're to startup founders are sharing lessons learned and pitfalls to avoid in their online businesses. And now here's Dave and Craig.
Speaker 2 00:00:19 All right. Welcome to episode 2 65 of rogue startups. Craig, my God, it's been for forever. How are you doing?
Speaker 3 00:00:28 It's been a hot minute, man. I'm good. I'm glad to be able to chat. It's been many, many weeks since we've talked. Last things are good. It is almost springtime here in new England, which is very welcome, but yeah, it's nice. You know, getting settled back in the U S and looking forward to seeing you and our other SAS friends in Minnesota next week.
Speaker 2 00:00:51 Yes, I am looking forward to that as well. It has been far too long since we've all had a chance to get together and you and I were just reminiscing. The last time we saw each other in person was like five, six years ago. So long, long, damn time, long damn time. Yeah,
Speaker 3 00:01:08 Crazy. How's the business.
Speaker 2 00:01:11 Things are good over here. It's been busy. It's been all over the place. And part of the reason that we weren't able to record in February is that I was doing prep for big snow, tiny comp. And we had that at the end of February. And it was good to see everybody and to go over what was going on in the business, but what was very poignant and what was very needed is that we always talk about how we're supposed to talk to our customers, how you're supposed to listen to them, try to figure out exactly what they want, understand their pains, do this all deeply. And you and I have talked about this dozens of times in the podcast, but when it comes down to like, how much you do that on your day to day stuff in the business, I don't know about you, but in my case, I feel like with my direct hands and customer support that I felt like I had kind of enough touch points with the customers.
Speaker 2 00:02:06 But the truth was I got asked some really hard fucking questions at big snow. And they were like, well, you should know this stuff. Talk to your customers. Like, why are they doing these things? And I'm like, God dammit. You're right. And so I kind of ended up spending the vast majority of March scheduling and running these various customer interviews. And originally I had said I was going to do three. And then later I was like, oh, this seems to be going pretty well. Let's try to double that. So I ended up saying I was going to do six it's Tuesday, March 29th. And I'm going to hit five by the end of the month, I had one that was scheduled and then they canceled on me and they're not able to do it. So my sixth one dropped, but I still got five good ones.
Speaker 2 00:02:51 And I've been asking like side questions on customer support. So I've been like in this, I guess you could call it customer development phase. It's not really customer development. It's more like customer discovery. And just trying to get more clarity on why people switch to the platform, why people stuck with the platform, what they love about the platform, what they feel like could be improved. Cause I realized also that I hadn't done a customer survey since like 2018 about like what things you want to improve and stuff like that. So I started all these roadmap calls and then I turned it into a general customer interview. So I've been talking with people on the side, talking with people that are migrating talking with all of these people that have already been with the platform for a long time, just to kind of figure out like, what is the essence of why you want to be on our platform here?
Speaker 2 00:03:43 And that has been a very intense experience and a bit of a good learning one too. I think it's shaping some new Q2 strategies here. The flip side of all of that is that because I'm doing all these customer interviews and I'm also trying to finish up with the closing of the, the Jilt windows closing now. So that has been another part of stress on the business, trying to get all these people to shit or get off the pot, so to speak. And yeah, we're not seeing as much conversion on that, on the tail side as I was at the flip side of that. So yeah, that's kind of been
Speaker 3 00:04:20 To be expected probably. Right. I mean, I think everyone who's serious about migrating off of Jill would have done it already. And now you have the hobbyists or people that aren't that pressed about it, right?
Speaker 2 00:04:30 I'd say it's a mix, but you know, the ones that were truly serious about it definitely did it earlier. The ones that were like, oh my God, email marketing is my bread and butter. I can't mess with this like a need to get it done while I have control over this. And I have the time to execute and, and if, basically leave huge amounts of space for problems that we run into glitches that we have. And if all else fails, you know, I'm assuming that the ability to move to somebody else, if it didn't work. Right. So we definitely had a lot of those, but then we also, I know that there are a lot of people that are probably just waiting till the last minute and they are going to be very sad when that happens, because we're not going to have the ability to access their Jilt account on May 1st. And I have a feeling I'm going to get a rash of people that first week of may coming in and saying, all right, we're ready to migrate. And I'll be like, okay, here's your blank recapture account. Let's just set you up some basic campaigns. I have no access to your information anymore. I'm really sorry about that. I only sent you like 15 emails and a couple of phone calls. So I don't know what to say, man.
Speaker 3 00:05:33 Yeah. That's tough. That's tough. I have a question about the customer calls, customer discovery development. Did you get the questions answered that were raised during like the big snow events? Like, did you get what you were looking for there overall?
Speaker 2 00:05:49 I believe I did. The thing that they really wanted to hammer me on was basically like what it, that makes them want to move to your solution as opposed to somebody else. Do you deeply understand why they want to do that? And I feel like I have a much better insight into that now the specific things like the specific triggers and even some very specific language that they're using to do that. And I think this is going to help shape what our marketing message is going to be in Q2. And I have a website redesign I'm looking at for Q2 and all of this language is going to end up going on that website as a result of that work. So yes, I do feel like there has been a greater level of clarity. And before I was like, you know, an EOS, the, one of the things that you're supposed to do is like document the blank difference where blank is your business name. Right? So document the recapture difference, you know, what is it that makes you better or different or why somebody wants to switch to you compared to all your competitors. Right. And that was one of the things that I was supposed to write this quarter. And before big Snell, I was struggling with that. I really was. And after I got these interviews and I put this thing up, boom, it just rolled. Right.
Speaker 3 00:07:06 I was talking with Asia around Joe a couple months ago, I guess now about like a lot of these kind of growth questions. And yeah, she asked me, she's like, okay, when's the last time you surveyed your customers? Or like had a bunch of calls with them. And I was like, never. And we still do send the product market fit survey to customers and like very few actually fill it out. And it's been a long time since I've looked at, but it's interesting because like, those are your existing customers and that language and why they come to your platform and all that is good and interesting, I think, but I think another interesting question is like, you're not standing still, right? You're going to be developing recapture into like, you have SMS now and you have all these other things. And so like where your product is going and where the messaging is going, is going to shift.
Speaker 3 00:07:51 And so I think the like serving customers is a data point and like the language they use is something you should consider. But it's just a launching point probably for a lot of the other insights for more of the forward-looking stuff. You have all these insights. Now, this is how I'm thinking about it. Like we will use that plus kind of like what I think and where I think we're going to really get it, a lot of that messaging, because I think if you just market to the persona of your existing customers, you're going to end up behind pretty quickly because your competitors are all iterating and pivoting. I think that serving customers can be a bit of a trap in that respect.
Speaker 2 00:08:30 I'm not sure if I hundred percent agree with that. I hear where you're going with it. And I think I partially agree with that. So I think that there are basically customers all over the map, right? And the customers that we recently got, or the customers that are staying with us, obviously I want more of those kinds of people and you're right, that we want to do the forward-looking stuff and I can help bring them along with additional messaging after I get them. But I feel like I also need to meet them where they're at. Right. And I need to find the customers that are struggling with the things that other people have come to recapture to solve. So basically this isn't going to sound like too much of a revelation, but basically the messaging that I've kind of landed on here is that we can give you agency results without the agency price tag, because there's a lot of email marketing agencies that are out there that charge huge amounts of money.
Speaker 2 00:09:22 And the customers that have used them are all universally disappointed. And they just want to come to recapture to have us do a simplified version of what the agency was doing and which still is very lucrative for them. And they don't like the complexity because they're the ones who have to manage it themselves. They don't want to pay somebody else to do it. They just want it done. And they want it not so complicated that they can manage it themselves because they don't have a big budget. They don't have a lot of staff. They don't have a lot of time. And so my messaging needs to speak to that piece of it. And I feel like that is already kind of universal. Like I can move forward and I can add new things to the platform that are going to help that segment without compromising that message. Like, I can still put that message out there. And it doesn't mean that my customers are stuck somewhere. It means that I can get them where they're at and pull them up to where recapture is going. So I partially agree with your assessment there, but I feel like I still have to meet them in that middle. Right?
Speaker 3 00:10:19 Yep. Yeah. That's why I said like that language is a good starting point. And then like with a twist, you know, that's how we're thinking about it, but it's hard. It's hard cause you don't want to alienate your customer base too much. You know? And I think about like an example that a lot of us know and relate to is drip, right? Drip with Robin Derrick was marketing automation. Right. And then it pivoted to e-commerce and I think that was a good example of like, eh, they did and they didn't alienate their base. And like, I think arguably like we maybe aren't their base and that's why we feel a little alienated as like going to Indy SAS folks. But they probably had a lot of good data that like the majority of their best customers were e-commerce. So anyways, I know this is a tangent, but I think it's a super interesting to look at your customer base and talking to them. And then that informing messaging is still it's great. It's neat that you're able to get all that insight. I'm sure it'll be super helpful.
Speaker 2 00:11:11 I certainly hope so. Unfortunately it now means that I have a shit ton of work to do, to try to execute on that messaging. And so we're still closing out other things and the cold sales has been shut down and other things have gone on along the way here, but one of the things that I'm actually going to do at MicroComp, so I'm coming in on Saturday, but I'm getting in pretty early. And while I'm basically waiting for all of the festivities and things to begin, I'm going to do my EOS retreat that afternoon. So I mean, I'm basically in a different place. So it's like I did the go somewhere different. Right. And I'm sure I can find a place that's quiet, it's a hotel. It can't be that hard. Right. And just sit down, answer those questions. Last time I did it, I had it done like an hour and a half.
Speaker 2 00:11:56 Cause if you're doing your quarterly updates, they say it takes an all day thing. But when you're doing it by yourself, I've not found that all day is necessarily useful. Even when I did it the very first time and I had all these questions to answer for the very first time and I sat down and I thought about it and tried to be careful and brainstorm. I didn't feel like the extra time I spent on it really made it super valuable. What I initially sketched out was kind of where I ended up. Maybe I did a little bit of refinement along the way. So, you know, I only need a few hours to do the EOS update for the rocks, but you know, I've got all this insight now I've got some time to do that. So that's kind of my pre MicroComp game plan here. Cool. Yeah. How are things going on the Casto side?
Speaker 3 00:12:41 Things are good, man. We we've had several months of pretty strong growth, which is cool to see like our sales guys are selling a lot, which is neat. Like they just have been on about six and a half months now. And so it's cool to see them really slotting in like the sales process and the sales team is starting to inform like product direction a little bit, which is cool. Like that's what we wanted is like kind of like your customer discovery stuff is like potential customers and like listening to what they need and what's making, or keeping us from making those sales. So that's cool. Like I'm finding like the product process that we talk about a lot and I just struggle endlessly with is getting better from our end. It's still is just like, it's a lot more data points and a lot more structure to it, but it's still just at the end, like flipping a coin on what we work on next to like, we have a lot more educated to the educated guests than we did before, but it's still an end is a little bit of like intuition and kind of what, what I want to do, which is fine.
Speaker 3 00:13:45 Like, I don't think it's wrong. We're making those decisions on like a quarterly basis now, which is nice instead of like a weekly basis kind of setting out like a product roadmap for a quarter. So that's been cool, like having a little more structure, having a little more intentionality to it, to say like, we're going to build these things and we're going to improve this part and things like that.
Speaker 2 00:14:05 Yeah. Product roadmap stuff is hard. Every time I've sat down and done the product roadmap and I'll go through the whole Kanban board with Mike and I'll be like, all right, these are our priorities, inevitably within one or two weeks of doing that customer shit comes in and screws everything up. So then, you know, we've got some really high profile customers that are like a significant chunk of our MRR. So when they basically say jump I'm yelling how high sir. And I really want to take care of those customers because they're super important to the business. So when they come and ask for a bigger features and it makes a lot of sense platform wise, then I'm trying to find a way to slot those in. But that also disrupts like all of the other short, medium long-term stuff we want to do because you get these demands that just sort of come in.
Speaker 2 00:14:57 So I'm like, alright, I gotta thread this in. And you're right. It's like voodoo, you know, I'm slotting stuff around in the Kanban board trying to make stuff happen. But you know, once I get past like the first 10 issues on the board, I'm noticing that it just kind of falls into a black hole after that. And unless something comes to bump those into the top five, we almost kind of start ignoring them. And I saw this on our old Kanban board in Trello. And now that we're back in GitHub, I'm seeing it again here. And I don't know what the right answer is to make that work better. Aside from hire more engineers to work on stuff faster, which we all have budget constraints on that. And we're no different here, but aside from like taking funding or hiring outside of a budget, I'm not really sure how to address that aspect of it and try to keep everything on track.
Speaker 2 00:15:48 You know, at one point I think we had sort of flirted with the idea of saying, all right, we've got our product backlog and we've got the customer backlog and the customer backlog we'll decide like the idea originally was going to be keep the customer backlog clear. And then the product backlog is what you work on when there's nothing on the customer backlog. But what that quickly turned into was the customer backlog always gets focused on and the product backlog gets maybe 10 to 20% of the time. And that's not right. Either. Like you just not pushing anything forward at that point. So yeah, I don't, I don't know any better insights on this side to that. We're struggling with it here too.
Speaker 3 00:16:23 Yeah. And I mean, for us, it even comes down to like, yeah, we have several, I think everybody has like a couple different customer personas, you know? So, so like for us, everything is about private podcasting, right? Like that's all of our kind of intentional new focus. And then like within private podcasting, there's like the use case for the customers or for, for the companies. Right. Like companies using it internally. And then we launched an integration with Stripe a couple weeks ago. And so now, like you can charge for access to your private podcast on cast us. Right. So like we could have a private podcast, we charged 10 bucks a month and people that pay us that money, get this secret feed. Right. Where you, we talk about like the behind the scenes stuff. It's really cool. So like we're even making decisions like, okay, how much new features do we build for that creator segment or for the company segment?
Speaker 3 00:17:07 And it's all just like, yeah, I agree. Like the first, next couple steps are usually pretty clear and then it's just a void of uncertainty and just nothing happens. So we're trying to make one or two good decisions per quarter and like just limit our world to that. Because otherwise it's just daunting to think about like, from a product perspective, like where do we want to be in three years? Like, that's just not even worth thinking about like in, in depth or like trying to plan it out. I think conceptually, we want to know where we're going. So we're making progress towards that. But like, we don't try to roadmap any more than that because like you said, just shit comes up and you go spend a quarter on something that's totally different. And your whole, you know, the big plan is, is thrown off.
Speaker 2 00:17:50 Right. And like, so in the context of your, okay, ours, are you finding that, that you put too many OKR hours in, in a quarter and you basically need to cut back on those because I just noticed that of the rocks I had. I think I put in a total of like seven rocks. And when I wrote them all down, I tried to tell myself, oh, it's fine. Because some of these rocks aren't really mine, but five of them still were, and I didn't finish all of them. And I I'm looking at that now going, I bit off way more than I could chew here. That was not smart. Are you seeing the same thing with your okay, ours?
Speaker 3 00:18:24 I think it's a little different cause like I don't have okay. Ours, you know, like the company has okay. Ours and then like each group, which has a person or people that are responsible for those, like, you know, we call them like division level OKR, but like, I don't have a set of KRS for myself. Like if I were you, I would try to set like three max, you know, and just make them super high impact. And then you're giving yourself about a month to finish each of them. You know, if you think about it, sequentially like that for us, one thing we learned with, okay, ours, and they're a little different than rocks because there, and I think this is where EOS and OKR is differ, is like, it can be hierarchical. Is that a term like they can cascade? And that's how we try to do it at the beginning.
Speaker 3 00:19:09 And it kind of made sense. So like the company would have an objective and then to meet that objective, we thought that the key results, like the rocks needed to be assigned to each group specifically, and then for the group to meet that they had to do X, Y, and Z. You know? So like an example would be like, be the leader in private podcasting, right? That's the goal, the old part of the objective. And then the key result would be like product design, this feature development, build the feature marketing, have the marketing copy sales, have collateral and sell three deals or something. What I learned is that I think is wrong because like the company can have a goal and the groups can have goals that are not directly associated with it. And you think about like development, like building a feature is a worthwhile goal, but, but they have other things that are maybe more important, you know, like uptime and code coverage and developer happiness and you know, some of these things. And so like, what we've said is the company has goals. Okay. Ours. And then the groups have, okay, ours and they're related, but not like in a one-to-one fashion where say we have six divisions, there's not six key results or what you would call like rocks on the company level. Like they all just live on the group level.
Speaker 2 00:20:27 Interesting. So when you said that you didn't have an OKR, my jaw kind of hit the floor a little bit. I feel like the OKR is for the company kind of are owned by you. So I'm Get explained to me how that works. Cause obviously there were things that, I mean, all of my rocks are mine. Like there, the company rocks, but at the same time, it's not like I have other groups to run them. So I mean, by default they sort of become mine. I'm curious how you set those OKR is, but then you aren't responsible for them in some way.
Speaker 3 00:20:59 Yeah. I mean like at the end of the day, um, I think, well, I think a couple of things, one the size of company we are, I think is really weird for setting goals and having people entirely own them. Right. Because like they don't have budgets, they can't hire people like, you know, Sam, our head of growth, can't just go hire another marketing person or content writer or an SEO specialist, something like that. Like we're just not that size of company. I think when you're 30 or 40 people, then you really should say like, okay, Sam is in charge of marketing and he owns everything. I am very much involved in like setting those OKR hours and helping report and resolve things. So that folks stay on target. And to that end, like I think I'm kind of responsible for all of them and responsible for like all of them funneling up into our company level goals.
Speaker 3 00:21:50 We're not so big to where I'm not involved on like the group level at all and just I'm involved at the company level. But so I kind of do both. So like, yeah, I guess I own the company level goals in the respect that like, if we set group level goals, right. They will be S like the company level goals will be successful and we'll meet those and the coordination right. Of each of those groups and working together and stuff like that. But it's not like I'm not doing marketing and I'm not doing support and stuff. So like, in that respect, I, I try very hard not to be directly responsible for any deliverable, because I've just found that like, I have too much other stuff going on and too many other things I think about to be able to like, write that email or be on that too many sales calls.
Speaker 2 00:22:34 Gotcha. Okay. That makes a little more sense. Yeah. When you said that, I was like, you got to own those it's like, but you do, it's just the way you stated it was not. Yeah. It it's, it's basically, you're the one in charge of those things and you kind of, I don't want to say, you're not really directing them. You're not really shepherding them, but you're making sure that everything is kind of getting done. So you're the coordinator. Sure. We'll call it coordinator.
Speaker 3 00:23:03 Yeah. I mean like what, what is the saying like, uh, CEO's job is to make sure there's enough money in the bank, like hire the right people and set the vision. And like, I try really hard to basically do those things and like the set, the vision set, set, and communicate the vision is, uh, is like that right with, okay, ours, right. Is every quarter we think about where we're going and talk with everyone in the company, especially like the group leads. And I've just found like, and I think this is a lesson for everyone who's building like past a couple person team is like that middle ground of like you're trying to set and communicate the vision and think big picture and be in the weeds is super hard and like it's yeah. I just, I can't do it anymore. And I think like, if I'm honest about like my highest leverage use of my time, it is like making sure we have enough money and hiring people and communicating the vision so that like awesome people we have on our team can do their best work to help us achieve those goals, you know?
Speaker 2 00:24:04 Yeah, absolutely. I'm finding those same struggles as well, because we had two new people on the team in the last few months here, and I probably didn't communicate as much about the values of what we're all about and really sort of focus on the vision, even though that was, I mean, that's not fair. They really should have heard that vision from me multiple times to make it clear. Like, why are they selling? Why are they doing this QA this way? Like, why does it matter to the customers? Why do customers use our platform? That kind of stuff. I wasn't communicating that very clearly. Now I will say to Mike's great credit. He was actually, you know, he and I have had plenty of discussions about those values and why we're doing things and why simplicity is so important and things like that, which is one of our values. And he was able to communicate that to her. And I found this out because our QA engineer, Julia was coming back and telling me, oh, we're doing all of this UX stuff because I understand it's important for customers. And I was like, yes, I should have been the one saying, where did that
Speaker 3 00:25:11 Come from?
Speaker 2 00:25:14 I'm like, thank God that the values got communicated, but that really should have been my job, you know? And it is because I'm like trying to do all those other things. So I, you know, I'm focused heavily on sales and support and marketing. And so trying to also be the visionary leader guy on top of all that you're right. It's like, I don't know what your vision is like, but like, my vision has gotten to a point now that I'm older, where if I'm reading something, my eyes will get tired very, very quickly. And I had to like, take a break and put whatever it is down. It's, I'm pretty sure it's from all the time that I've spent on the computer. But it's one of the things that I think my eye doctor said to me is that when your eyes get tired of focusing, what you need to do is go outside and look at stuff far away. It's the same switch and vision, right? You got to go from big picture to tiny stuff, big picture. And you can't, if you're focusing on one all the time, the other one becomes very difficult to do. And you have to switch to the other to give yourself a break from the former one, if, when it's fatiguing you, and it's kind of where I'm at, but unfortunately, you know, I'm, I'm stuck with these roles for now for better or for worse, and that's what has to happen. So, yeah.
Speaker 3 00:26:24 Do you, you asked like about vision, I haven't done the EOS like three and five-year plan and a while I might do it on the airplane on the way there. Cause I have like four hours of travel time. Cause we have a layover in Chicago. I heard from Jordan gall. Like it was a couple of years ago, like 5 million in revenue and a million in profit. That would be pretty cool. Like we're not there for sure. But, but like that's a good medium term goal. I don't know if that's exactly right, but like something like that would be a really cool goal. Like to build high growth, large profitable company would be cool. Like we definitely want to be profitable because we don't want to keep raising money. That's kind of the medium term goal. And I guess the only, only update for me, Dave is we are having a team retreat.
Speaker 3 00:27:04 We are going to Chicago in June. We awesome going to white Sox game and yeah, hoping everyone can make it evidently getting visas to come to the United States for our team members outside of the U S is pretty challenging more than I, more than I thought it would be essentially like the fricking embassies are just not working. Full-time still because of COVID. And so like the backlog is a year and a half long in one case. So that crept up on us and kind of bit us in the butt, but you know, it's cool. We'll be zooming in our team members who can't make it for like, we're going to do basically a half day of like working together. We'll rent an office in a co-working place and like zoom everyone in who can't make it in person. And then like, we're hoping to get more than half of everyone, which is like everyone in the states to come. So yeah, it should be cool looking forward to it.
Speaker 2 00:27:52 Nice. Nice. And why did you pick Chicago? Just centrally located?
Speaker 3 00:27:58 Yeah. Essentially located should be really beautiful in June. Wanted like fun stuff to do. And there's just a ton of shit there. Yeah. Nice. I've only been a few times all for conferences and it's just a cool place, you know, to go to conferences. So yeah.
Speaker 2 00:28:12 Nice, nice,
Speaker 3 00:28:13 Good. The podcast again, after too many weeks, uh, of a break, but, but it's, it's really cool to catch up. Sounds like things are going well, which is awesome. Yeah.
Speaker 2 00:28:22 Yes. And I look forward to being able to see you and anybody in our listener audience at MicroComp growth. So if you are around and you see Crager, I wandering the halls, please come by and say, hi, we'd love to chat with you. Hopefully we can get this episode out before we go to MicroComp.
Speaker 3 00:28:42 I think we can cool everyone. Thanks for listening. And if you're enjoying the show, we'd love for you to share it with someone who you think would enjoy it as well until next time.
Speaker 1 00:28:51 Thanks for listening to another episode of rogue startups. If you haven't already head over to iTunes and leave a rating and review for the show for show notes from each episode and a few extra resources to help you along your journey, head over to rogue startups.com to learn more
