Rick (00:01.233)
What's up, Tyler?

Tyler King (00:02.766)
How much? What's going on with you?

Rick (00:04.705)
I am very busy. I'm trying to keep it all under control. hate saying that I'm busy, by the way. It feels annoying to say that. I hate it when people say it to me. Yeah, but I'm busy and trying to get under control. It's the first month of a fiscal quarter at Windfall. And so in my job, there's lots of stuff to wrap up. There's lots of stuff to kick off. There's reviews, there's board meeting, you know, all good stuff.

Tyler King (00:12.046)
Yeah

Tyler King (00:32.078)
I can't imagine. Yeah, I'm busy as well, but you I think in a less high pressure way, that makes like busy, like you come in in the morning, there's a lot of stuff in the inbox, but not like there's any major consequences if I don't do it, but I do it, you know, so in that sense, I'm also busy. We've got the fellowship ending this week today. Actually, this is the last day of the summer coding fellowship. So that will, yeah.

Rick (00:58.919)
Success.

Tyler King (01:00.846)
Um, I'm less involved than I have been like, we've gone through various phases of it throughout the years where, uh, I started it like, and for a reminder for people who don't know what that is, it's just like basically an internship, except they're it's pre-internship. They're working on their own projects because they don't have the experience to really contribute on a real code base yet. Um, I s

Rick (01:21.765)
It's paid. It's well, let me just give a little more contact. It is paid basically learning. It is like the best deal you could possibly get. If you have children who are in college, you should have them look at the fellowship next summer.

Tyler King (01:27.086)
Yeah.

Tyler King (01:32.494)
Yeah, no, it's a program I'm very proud of. I will say, part of me, it's to help people get jobs in software engineering. Now that the job market for software engineering is terrible, I am feeling a little conflicted about that. Like, should we be, like five, 10 years ago, it was easy, well, we weren't doing it 10 years ago, but seven years ago, it was easy to be like, learn how to code, you'll get a job, it'll go great for you. It's not quite as simple anymore. Anyway.

I'm not as involved as I once was so yes, like I think the summer went well, but also it's more of I'm more of an observer than like a You know feeling like hands-on super proud of my accomplishment, you know

Rick (02:16.411)
And as a result, you're like, I think we might cut it.

Tyler King (02:20.445)
Yeah, get it out of here. It only exists to inflate my ego. But then I also have, it's funny, my wife and I are on opposite schedules because she's a college professor, so she's busy every time except summer. And then the summer is when those college students come and work for me and I get more busy. So I'm about to ease off and then she's about to go back to work, which then trickles down to me. So my schedule this fall semester is going to be that I'm taking

one and a half days off per week for parental leave instead of one. So I'm about to lose a half day of work to that, which will make me even busier.

Rick (02:59.274)
Have you liked the four day work week?

Tyler King (03:02.859)
Mostly no. get it. if I were coasting with less knowing CRM, yes, I would love it. Like that extra day is huge in terms of your personal life, but I'm and I know I'm going to look back and really cherish being able to spend more time with my daughter and stuff like that. So I'm not in any way regretting it. But if I'm like, let's say I didn't have a kid, should I have gone to a four day work week? Absolutely not. That extra day.

that I would spend working would be fulfilling, I learn stuff. It gives me the things that make for a rich life. Whereas if I didn't have a kid right now and I were taking that day, I don't think I would use it. It would be more relaxing, life would be easier, but I don't think, looking back over the course of a year, I don't think I would feel good about how I spent my time, if that makes sense.

Rick (03:57.305)
Mm-hmm Yeah, that's cool. Yeah, I I'm jealous obviously, but I feel like there's like phases of that of where that's really great I could imagine like if you're in Like you're not pushing something forward or you're in like exploration mode and you just want to like think Think more have less more space. I could imagine it be really useful. That's not where you are right now from a work perspective

Tyler King (04:20.621)
Yeah.

Tyler King (04:26.635)
Yeah, right. especially I'm in a weird place with work where we know, well, I'm about to contradict myself because what we're talking about today is like, and we've been talking about is very big picture brainstorming stuff, but for the next six months or whatever, I know what we need to do. We just have to go execute and go do it. And it's not a, I'm not somewhere where I need a lot of space right now. I just need to put my head down and work.

Rick (04:53.085)
Yep. uh, when I was, when I left my, uh, my last job, my last real job, I should say, uh, in 2018, I, I took like eight, like six to 12 months off, like I've just like doing nothing. And I, everyone I would talk to was in a totally different mode. Uh, because it was mostly like an exploration of what I should do next. Um, and I, every, like, I got lots of what I would call interest from, from people who wanted to hire me.

my next job but my conviction on what to do with myself was so low like what I like conviction on how to spend time like you have high conviction on how to spend time right now I had zero conviction so like I would talk to these people they're like you know Rick it sounds like you have no conviction I like I really want to hire you or I would I really want to like progress this conversation but like I need a little bit more and I'm like you know what you're right and you know it was

Tyler King (05:48.406)
Yeah.

Rick (05:52.593)
Perfect for me at the time.

Tyler King (05:53.986)
Yeah, it's hard to have that many options though. Like there's something kind of freeing about, and again, I'm about to enter a phase where I have very low conviction, but like the projects we're currently working on, I have high conviction about. So, but yeah, there's, I know you said it was perfect for you at the time. I would, this is one reason I don't want to exit less knowing CRM. I'd want to start another business, but like what, it could be anything? No, absolutely not.

Rick (06:16.509)
Yeah, there's a lot of questions when you like have a blank slate and you have to decide what to do with your time. That is a hard place to be. It's challenging. It was a challenging time, but at the time I needed that space. I think I grew from it. Like I think it forces you to like reevaluate things. You have way more time to think.

Tyler King (06:28.567)
Yeah.

Tyler King (06:34.573)
I like the fact, by the way, I'm gonna plant a little seed, because I think I'm gonna come back to this later. I feel like there's this concept I run into all the time, you're, imagine you're at point A, and you're trying to get to point B, but you don't know point B is where you're trying to get yet. And you kind of like wander around in the darkness. And I kind of in my head imagine this as a spiral, like you go in a full circle, you go, you know, well, what if we did that thing? What if we did that other thing? You kind of open yourself to all kinds of ideas.

And after lots and lots and lots of work trying to figure out what to do, you've circled back around almost to where you started, but you're like an inch closer to the center of the spiral. and you kind of have to keep circling and circling and circling, but in most cases, I feel like where you end up is more similar to where you started than you ever met. And I feel like that happened with you where you went through this whole adventure and then you started a health benefits company. mean, something very, very similar to your last company.

Rick (07:29.317)
Yeah, there were two pieces, there are two factors there. One, I had a two year non-compete, so I couldn't do it like for two years. that was off the table, right? And then, you know, but yeah, that's, it's true. It's true.

Tyler King (07:36.275)
Mm, yeah.

Tyler King (07:46.458)
That actually happened, that almost happened to me with LessonWing CRM. I worked with you at Zane Benefits. I built a something like a CRM. You and I, you know, together kind of came up with this idea and we, and that was the inspiration for LessonWing CRM. Then I quit and it was like, I'm going to start my own business. But like, obviously I can't, I can't just build that same product that I just built for Zane Benefits. I don't know if I would have gotten sued or whatever, but it seemed like obviously I shouldn't do that.

And then like a couple of weeks later, Zane benefits comes back to me and is like, Hey, do you want to consult part-time? And I was like, yes. Can I get in writing that it's fine if I basically recreate that, that same CRM thing. But so for like two weeks, my brother and I were like, what are we going to build? Like we have to build something else. Yeah. So we went through, we were like, let's make an email client. Let's make a website hosting tool. Like we thought about all kinds of stuff, but then the moment I got that contract sign, I was like, it's a CRM. Okay. Great.

Rick (08:31.485)
Like what? Less annoying software.

Rick (08:43.677)
That's awesome. That's so awesome.

Tyler King (08:47.053)
I don't know how we got there. What's going on work-wise with you?

Rick (08:51.933)
I like leg up wise we had so I guess we had a really interesting partner meeting like let me just back up. July was the record month for leg up. We hit almost 22,000 in revenue for the month with after JD like with after like base pay payroll $9,000 in profit almost $10,000 in profit.

And so we have sort of a rule set for what to do with that up to like, uh, there's like $3,000 leftover. And so we did, we, were like, uh, what do we do with the $3,000? And I thought we had a really good discussion. And after our discussion, I went back to the waterfall and I realized we actually already had this set up. just hadn't followed it through. So, um, anyway, there's, you know, I don't want to rehash the entire conversation, but I think it was really interesting to think about, okay, like,

Everything we've done to this point has been to get to the point where there's after we get JD to a comfortable compensation, what we have leftover money to reinvest in the business or hire other people, et cetera, or pay ourselves more money. And we're there and it was like, we got there and we didn't know what to do. Yeah. Yeah.

Tyler King (10:09.687)
Yeah, it's hard. I've run into this at West annoying all the time where, cause like you want to go fast. You want to spend it, especially hiring people. That's the most exciting way to spend money, but that's such a commitment.

Rick (10:23.995)
Yep. Yep. it's, mean, July is the slowest month of the year for leg up. like if there's any, if there was any conviction in prior months about lead sources, like they went away in July, you know, so it's like, where do we spend the money? but we had a, I thought we had a really good discussion about like the buckets of how to spend money and I, and the framework that I would share for people, if you are in this situation, either personally or professionally where you have money that you don't know what to do with. And you're like, I want to spend it. That's like,

you know, I'm going to buy something, but I, and you feel anxious about it, which is what I was feeling is to talk about it with someone. And you can actually come up with buckets of like prioritized spending. one of those spendings could be like savings, you know, and, for, for the future. And so what we did was we came up with a number of buckets, where we were like, Hey, you know, we could pay JD more, we could pay Tyler more, we could pay Rick more, we could pay.

We could hire someone new. could hire a part-time person. We could invest it in marketing or leads. We could hire a dev person to supplement what Tyler's doing. We went through the list, agnostic, and then bucketed them into four or five things and ranked them. And what we found was the number one thing we wanted to spin it on isn't available. And then the number two thing we wanted to spin it on, we don't really have a whole lot of conviction around.

the ROI. And so the third thing was saving the money until we have conviction around the first two things. And that's what we're doing. And that, you know, I think we can reassess that every, every month. And worst case, we just have a kind of a treasure of cash to, to throw it at number one or two when we're ready.

Tyler King (12:06.369)
Yeah, when you say number one wasn't available just for clarification, like it's a lead source that we're already maxing out basically.

Rick (12:12.931)
Exactly. like there's it's it's not clear. Like it's not clear that we would we would be able to quickly turn that into a sale, for example, or be able to buy more of the same thing. So.

Tyler King (12:30.541)
We've had that so much with like AdWords, Google AdWords for example. Obviously you can spend an unlimited amount of money on it. is making hundreds of billions of dollars a year off of this. many times I've run into a scenario where we make a campaign that's on like small niche keywords and it works okay. And we're spending a thousand bucks a month or something. And then we're like, well, great, it's working. Let's spend 10,000 bucks a month. And it completely kills the ROI.

So we just have to sit there spending a thousand bucks a month, seeing this working channel and knowing we can't make it grow. It's real frustrating. Yeah.

Rick (13:05.913)
You don't want mess up the ad group, right? We don't have any ads running on Google right now. And I think that's a mistake. That's probably something we should, if we could find the right, if we could find the time and the right people to manage it, we should be running, yeah. Yeah, but it works.

Tyler King (13:22.157)
It's just so expensive and competitive though.

Tyler King (13:28.639)
It works for, yeah.

Rick (13:30.321)
I mean, our leads that we're buying are coming from search, right? And so I know that we could pay most likely less money per lead if we were, yeah, yeah, yeah, good.

Tyler King (13:33.91)
Yeah, that's true.

Tyler King (13:42.946)
Yeah, let me say what you're saying just like there is a different company that's getting leads somehow. And you're saying it's probably through organic search, paid search, do we know? We don't know how, but they're getting them somehow. They're getting these leads and then they're selling the leads to us. Presumably we could do whatever they're doing, get the leads directly, cut out the middle man. So yeah, it works for somebody, but yeah, you're better at this than I am. And I have a lot more faith that you could figure it out than me, but.

Rick (13:54.374)
No. It's most likely paid.

Tyler King (14:12.797)
I've, it's hard. There are people out there who are really, really fucking good at that. It's kind of like investing. like, I'm not going to pick individual stocks. They're like a whole industry of Wall Street professionals trying to beat me. I'm not going to win that game. Also Google's whole model is like, eventually you'd expect the price of the ads to get bit up enough that there is no real like ROI. There's just enough ROI that like people keep bidding, but not there. There's not like a lot of juice to squeeze there.

Rick (14:42.865)
I agree. mean, it should do, we should do, we should do, but do I have the conviction to actually spend the money? I mean, probably not.

So, but anyway, the win was 22K in revenue, 9K in profit, leftover money. Good things are happening.

Tyler King (14:52.925)
cool.

Tyler King (15:00.833)
Yeah, I think of it more like whatever the two to three K in profit, like a lot of that profit is still part of JD's like expected comp.

Rick (15:09.757)
Yeah, that's fair. 3K and like slush profit.

Tyler King (15:15.713)
Yeah. Which is still huge. mean, I, I, in my mind, it's still when we talk about like up health, I still feel like we're back in 2021 or whatever, where it's like, yeah. Like you've got a few customers and like an unimportant amount of revenue and it's about growing, you know, where does it go from here? And like, it really turned into a legit business, over those years.

Rick (15:17.479)
Yeah.

Rick (15:36.093)
Yeah, yeah, yeah like the the and this podcast chronicled it right I actually need to go start up to last calm start up I Need to look I need to look at what's on there because I know updated it at one point But I didn't I don't think I've updated in a very long time, but maybe I did log I Have 10 10 ext it since $2,000 and that was actually before leg up helped exist existed

Tyler King (15:40.812)
Yeah.

Tyler King (15:45.763)
yeah, because we have your revenue on there and it's completely wrong.

Tyler King (15:54.357)
Revenue, 2,000 MRR is what it says for you.

Rick (16:04.717)
because LegUp Health did not exist until 2020. So LegUp Ventures was started to start group current. And so what's happened since then is lots of businesses have failed other than LegUp Health.

Tyler King (16:05.26)
yeah.

Tyler King (16:22.861)
Yeah, well that's cool. I've still got my just big topic.

Rick (16:25.842)
Yep.

Rick (16:29.425)
What's your MRR?

Tyler King (16:32.237)
or like four and a half million ARR, what does that come out to in

Rick (16:38.141)
360, 300.

Tyler King (16:39.693)
Yeah, yeah. Here, I'll do- I'll give you down to the penny. I'll tell you what it is right now.

Rick (16:48.189)
400?

Tyler King (16:48.525)
divided by 12, 380,790.

Rick (16:52.441)
Nice. So when we posted yours, it was 240.

Tyler King (16:58.219)
Yeah, now most of that growth is because of the price increase, not user growth, but some of it is user growth. Yeah.

Rick (17:06.705)
We've both effectively grown the business over the course of this podcast. That's all that matters.

Tyler King (17:13.197)
That's all that matters, folks. Don't pay attention to the user number.

Rick (17:17.053)
Yeah, don't look under the hood. Just it's vanity. Vanity only.

Tyler King (17:18.925)
Yeah. you want to dive? Can I just take over the rest of the podcast? Do have any other smaller topics? okay.

Rick (17:24.221)
What about you, what's going on?

Rick (17:28.189)
Of course. the only, yeah, let me, the smallest thing I have, the only other thing that I'd like to tell you about is I did a level 10 exercise. So we've been talking about like rich life, both on the podcast and offline too about, you know, I think we're at a, we've, we've, we're settling again. So we took, we took, and our nephew and niece, six, seven months ago, our life is settling in. We have another two kids, Sable and I have like, okay, like we got to, we bought a house three years ago.

Anyway, things are settling, leg up health is in a good place. And we've been trying to figure out how to have conversations about what we both want to maximize in life. Cause we have a lot of responsibilities. Say what works full time, I work full time. so anyway, level 10 life, I don't know if you've heard of this, but it's basically a framework for defining the 10. There's a lot of tens. So effectively it's you define 10 areas of your life that you want to measure yourself against that are the, that represent your full life.

Tyler King (18:20.779)
You

Rick (18:27.547)
You then define those 10 life areas. So it could be like finances, health and personal and health, romance, partner slash romantic romance. It could be an in-home environment, work at professional, that kind of stuff. Anyway, we define the 10 of those. And then you want you to find what it entails. You then write your vision of what a level 10 life looks like. And that's like the ideal space for each of those.

And then you assess yourself on a scale of one to 10 on how you're doing against your level 10 vision. It was actually a pretty useful exercise to see one, how much overlap do we have on our level 10s for each of these life areas? Where is there friction? Where is there overlap? And then also seeing where you're really low, where you're high, where you're in the middle.

The areas that I am struggling, that what it exposed to me is like my health and fitness is by far my lowest level 10 life area. so since realizing that I've like totally shifted my, my, my health and my health routines. and, so like, that's number one. Number two is actually Sable and I's relationship, to where it used to be. And so we've got, you know, both of us were like, we got work to do, you know, we've been prioritizing other people, other things.

Yes, we've been prioritizing each other indirectly, but we have to actually get back into what we both want our relationship to be. And then the third is home environment, which I didn't expect, but it's like, we have this beautiful house, but like we haven't really fully settled since moving. And we haven't really figured out how to set the rules of the house with the new folks in the house. And so there's just like little pieces we got to work out.

But those were not the areas I spent were spending any of my time thinking about. But after I did this level 10, I realized, oh wow, like my areas of life that I thought were like actually not going well, I was getting frustrating with like career or social life or fun and recreation. Like, no, actually those are good. Like they're good enough. I need to focus on these other things. Anyway, just wanted to share that. It could be a really useful exercise if you type in level 10 life, chat GBT is super useful and a partner in assessing this.

Tyler King (20:41.665)
Mm-hmm.

Tyler King (20:54.497)
Yeah. I wonder if it almost has to be true that. So like there's there's people there are people who don't have the resources they need to live the life they want. Like they don't have the time or the money or the whatever the privilege. You do like you should be like you know you you have multiple sources of good income and you have control of your life. So I wonder if it's almost definitely true in every case for someone like you that the things

you need to work on most are the things you're not working on. Right? Because like otherwise you're a capable person if you had been working on it, it wouldn't be a thing you need to work on. You know what I mean?

Rick (21:28.091)
Mm, it's probably true.

Rick (21:37.265)
Fair, yeah, true. think, yeah, that's probably true. two, like health and fitness is very much like a personal controllable thing. I think when you're married and you have children, home environment becomes a very much like a less controllable thing and it requires partnership. And so like to an extent, like I could have been working on that, but like not making progress because of disagreements. But that's not the case in this situation.

Same thing with like the part, like romantic relationship area of life. Like that requires partnership. if again, like I could be put, I wasn't focused on it. If I was pushing on it, do I think I could have affected it? Absolutely. You know? so.

Tyler King (22:15.649)
Yeah, you're either failing at something or you're not working on it. It's one of those two things.

Rick (22:19.29)
That's I think you're probably right. I think you're probably right

Tyler King (22:23.797)
Okay, I'm gonna, I'm not gonna like read whatever the level 10 life thing is, but I'm gonna informally think about what you said, because I'm not disciplined enough to go through the whole process.

Rick (22:32.861)
Well, the thing I think that the two utilities here are like one if you're if you're if you're like having ongoing dissatisfaction and you can't like get your put your finger on it, but you're pretty privileged like this is a useful tool to zero in on exactly what might be bothering you and for me it's like Okay, Rick, like stop practicing everything else other than your personal health like it's very important to you like go you got to start working out again, you got to

Really prior like eat better. You got to get down to a better weight. Like that was very, very clear. And then the second thing is like, if you have a partner, I think we haven't gotten to this part of the exercise yet, but I think overlaying your two level 10 life visions relative to the same life areas. I think, I think that's going to be a really useful exercise, but we haven't, we haven't done that yet.

Tyler King (23:17.473)
Yeah. Cool. Indeed. so yeah, back to my stuff. Yeah. So I'm still kind of in this ongoing, I would just say product strategy is the high level description for this. It started out as the discussion was framed around VoIP. I kind of hinted at last time we are maybe moving in another direction. I think at this point I can say I've officially ruled out VoIP as the next product, not like officially ruled it out forever.

Rick (23:19.121)
Thanks for letting me talk about that.

Take it over.

Tyler King (23:46.882)
you know, indefinitely into the future, but that is not the next thing. So I maybe I'd start with just running through my reasoning there. And then again, this is a conversation that could go in any number of directions. So like, okay, to set the context as a reminder for what we're talking about here, West Nowing Serum has one product, one price, which means the only way to grow revenue is to grow users. And we, that's the best thing. We would love to just keep having one price forever, grow users.

And that's our growth strategy. like for the past, you know, three years or whatever on this podcast, we've talked about nothing, but how do I grow users? And none of it's worked. So that got us thinking, well, okay, could we also side by side with that? Try to grow revenue by having something else we can, we can charge for in addition to CRM that led us to VoIP. It may seem like a counterintuitive solution to it, but the thing I liked about VoIP is that it.

is something I think we could build a competitive standalone VoIP product. Not necessarily like way better than all the other ones out there, but like as good. And then we could differentiate the way we always do on price and customer service. So we'd have kind of two separate things to market and have more actual top level leads coming in. That was the thought process there. In examining that more, what occurs to me is we're not good at that type of marketing. I'm not saying it couldn't happen, but like,

Going from zero to one is really fucking hard. So we're just, we're turning the problem we already have into another exact same problem, basically. The opportunity here is instead to say we've already got hundreds of users coming in a month. We need to sell something to them. What? Yeah, exactly. That's why I set that up. We're going, sorry, Rick is making the spiral motion with his hand. Yeah, we came back to where we started, right? But like,

Rick (25:36.509)
You

Okay, I was not expecting this today, but okay keep going.

Tyler King (25:44.535)
but like an inch closer to the center.

Tyler King (25:49.736)
the whole thing that started this is increasing ARPU, not creating a whole new business that we can mark or, like having to go from zero to one. It's, where's the easy money. And the easy money is we're getting hundreds of users a month. Now that we're also churning hundreds. So we're netting zero, but hundreds of new users a month are coming in. If we could just sell them something in addition to the CRM, what would it be? And like some people would, would, take an upcharge to do VoIP, but that's not at the top of the list.

and that, that led to what I teased or we talked about a little bit in the last episode, but we didn't like really fully sink our teeth into is like, can think of it as a separate bundle and add on a second pricing tier, however the pricing is structured, but just like a lot of people buying less knowing serum are already, they're coming in. They're like, I've got a budget set $50 per user per month. That's what I'm willing to pay for CRM. They look at us and like, 15 great. But if we were like, there's also another one for 30.

10 % of them or something would just be like, well, sure, yeah, like that's still cheaper than I was planning on spending, like why not?

Rick (26:55.601)
Yeah, and as long as there's something in there that they really want, then they're going to buy it. All it takes one thing.

Tyler King (26:59.627)
Yeah. So I think exactly. I think we've more or less settled on that again, back to the, you know, the, the spiral has taken us back to close to where we began that the goal here is not to like ship something totally new, but something that's more of a compliment to what we've got. Okay. Now that brings us to something you said in the last episode was, well, you know, I'm, don't exactly disagree with you, but it's so you said increasing our poos nice, but increasing users is even better.

Rick (27:20.128)
You calling me out?

Tyler King (27:30.475)
Right, which I mean, am I representing your opinion correctly there?

Rick (27:34.973)
The context is long term, like for the long term sustainability of the business.

Tyler King (27:41.1)
Yeah. These two are kind of at odds with one another in the sense that every feature you build, if you offer it for free, it's a more, that $15 tier is a more appealing thing for users. And that's how that's one of many ways maybe, but we've tried many of these things, none of them work. That's one way to get more users is to have a more competitive product by moving it into the upper tier. You get more revenue per user, but the overall value proposition is worse because you're paying more to get the same thing, right?

Rick (28:10.269)
Yes, but you can also, this is I think also what I said, which is you can spend more money on marketing when you're buying a $30 user versus a $15 user.

Tyler King (28:19.115)
Yeah. Okay. That's, that's true. So I'm not saying they're like 100 % fundamentally in conflict with one another, but they are, the more this is the same challenge that any freemium business has is like, you want to make the freemium, the free tier as good as you can to get all those free users. But then you, you also want to limit it so that they feel like they need to upgrade. You don't want to make the free tier so good that no one ever bothers to upgrade. It's a difficult trade off.

This is the same type of thing. So for example, we're about to be done building an automation feature. Should that be a 15, should we just ship that to all our customers the way we always have with every feature ever? Or should we say, no, we need, that's going to be a part of some second pricing tier or bundle or.

So that's one of the things on my mind is, we offer, man, I've got so many different directions I want to talk about this in. Let me follow that thread. Sorry, I'm talking so much. Feel free to interrupt me and.

Rick (29:17.991)
This is great. No, this is good. I appreciated your, if you hadn't played to the seat earlier, I would have probably approached the conversation a little differently, like with more challenging, but I'm following. So keep going.

Tyler King (29:27.767)
You

Okay. So I said, we've spent the last few years trying to increase user growth and it's failed. The reality is that our current approach to that, we don't know if it's failed or not yet. We haven't really executed on it. And this is as a reminder, the term car play is our like code word for this, which is like, we've shifted how we think about what features we should build next from what are our current customers asking for to what are the like highest.

effort to impact ratio for new customers and in particular, checking a box. Like someone's coming, they're looking for a CRM, they're like, I need these five things. Oh, you only have four of them. Nope. I'm not considering you. How do we add that fifth thing? And the list is different for everybody, right? We already check all the boxes for some people, but we can expand the total addressable market or whatever. So we've been working on these features, but we've only shipped a couple of them.

Really one, we shipped automatic email logging, like an email integration, but we're working currently on mobile Kanban and automations. And those are like big carplay features for us. It's big enough that like after that, I don't even know what's next. Like these are clearly in a tier separate from everything else until we've actually shipped them and seen does that impact our free trial to paid conversion. It's hard to say whether that strategy was valid or not. You know what I mean?

Rick (30:55.953)
Mm-hmm.

Tyler King (30:57.795)
so that's like a conviction question. I'm asking myself, if we think it works, we should just keep doing that. And if we think it doesn't work, we should say, you know what? We've got to go after this higher ARPU thing. And if we have to sacrifice the, the value prop for our $15 tier, so be it.

So that's kind of where we're at. There's, other decisions like around what products would we build, et cetera, but.

Rick (31:21.053)
Do you have a timeline on when you wanna make those decisions?

Tyler King (31:26.187)
Well, maybe, so there's a kick the can down the road option, which is to say, give ourselves time to decide whether we think CarPlay worked or not. I think that would be probably end of 2026. Like I think we'll probably ship all these features around the end of 2025. And I think it takes a while for the effect of it to be known if there is any effect.

Rick (31:50.385)
Yeah, and does that include packaging changes or just keeping the $15 per user?

Tyler King (31:55.18)
Potentially. yeah, so that's a different, a different question is, that that's also on my list here is like the, should we reposition ourselves for kind of a more specific type of customer?

Rick (32:05.565)
Yeah, I mean to me like well, I guess let me back up there There's like positioning for different customer, but then there's also like $15 verse $30 bucket Does your carplay approach like I just want to make sure I'm clear on when you say carplay it does it include the potential for 15 and 30 dollar packages? Okay

Tyler King (32:21.101)
It could, so like let's take automations for example. We could ship it in the $15, I mean, we only have one price, just ship it to everyone. And that makes the $15 tier more competitive. Or we could say, no, you need to pay more if you want that. We'd probably also pull out form. Like one of the hard things here is you need like a critical mass of things to have that extra tier. I think those both count as carplay, but charging more for it weakens the carplay argument again, like.

Rick (32:48.199)
Yeah, yeah.

Tyler King (32:49.013)
more people would want it at 15 than the number who would want it at 30.

Rick (32:52.465)
And the other thing that like you, that we don't, that you don't know the answer to is when you add two packages to the website, how does that affect your conversion? Just because of the, of the choice paradox of choice, right? Like, and then you potentially, have this, relativity, bot, you know, misjudgment. so like when you put a $30 product, even if it's, you could put a $30 product next to the $50 product and take

have less features in it. But because it's worth more and it's sitting right next to the $15, all of a sudden the $15 item is devalued in our brains. And so there's a lot of like, I think pricing and like psychology here that you're gonna have to think, like be ready to pivot on. like, I mean, you're already like kind of like that break even on user growth. If you introduce a major change to your packaging,

Tyler King (33:30.775)
Mm-hmm.

Rick (33:51.453)
Uh, on pricing, not positioning anything like from a, from a personal standpoint, but you basically say, now there's choice. Who knows what could happen from a user conversion perspective? Like it could go down. could get, yeah. Yeah. So that, that's something you could probably test, um, over the course of a month. Uh, if you were willing to take the hit and learn a lot, like you probably could reposition your entire, uh, packaging a little bit. And like your $30 product might not be as good.

Tyler King (33:54.754)
Yeah.

Tyler King (34:01.813)
It could get better, could get worse, yeah.

Rick (34:21.041)
but you'd at least start to understand some of the user behaviors, you know, of like, does like, how does our current traffic react to choice? Does it, you know, is it like a massive swing one way or the other, or is it just like a ripple?

Tyler King (34:25.654)
Yeah.

Tyler King (34:38.187)
Yes. So I'm going to give the why that's harder than it sounds thing, but I don't want to make it sound like I'm copying out. Like we're going to have to do something at some point. So I'm not saying like we shouldn't, but I do think when people talk about testing pricing, there are some companies like I'll use intercom as an example. Everyone knows they're just assholes when it comes to pricing. And when you go to their pricing page, whatever you see, it's not going to surprise you because they're just brutal. we

Rick (34:57.01)
Ha

Rick (35:02.717)
But they also have an enterprise sales motion with salespeople behind it. They're not trying to do online. Their online conversion is, they do online conversion, but the entire point of their online conversion is to feed leads to their sales team. It's a freemium product. That's not their end goal.

Tyler King (35:05.611)
Yeah, yeah. Well, no, they do both.

Tyler King (35:15.213)
don't know if that's...

Tyler King (35:20.385)
I think that's partially true and not entirely true, but in any event, our brand is built around, we have one price, we're not trying to screw you, we're not trying to maximize shareholder value. If you go to any of the review sites like G2 or Captera or whatever, which a lot of our marketing comes through those, they're like, what's one of the big pros? Only one price, you don't even have to worry about this. Even our current customers,

We just, in 2020, we raised prices on new customers only. And then in 2024, we said, hey, current customers, sorry, we were hoping to keep that old price as long as we could, but it's time to raise it. And most of them were very understanding, but some of them were like, hey, I thought I got the legacy pricing, what the fuck? A lot of people might see this, oh, you're getting ready to charge me more again, huh? Like I do worry about bit by bit by bit chipping away at the trust that we've built. I just adding a new tier and then removing it a month later.

isn't as, you don't go back to where you started. You've made everyone think, this pricing is not something I'm secure in anymore.

So that's not to say we shouldn't touch pricing. It's just to say, I don't wanna do this like move fast and break things. So just try it out and see what happens. I wanna put my best guess forward and try that so I don't risk burning all the trust.

Yeah.

Rick (36:49.287)
That's getting into how to do it more so than like what to do. So like it's a little premature, but.

Tyler King (36:53.803)
Yeah, it's premature, but just to say, want this conversation to be, let's try to come up with the best idea, not let's come up with five ideas and test them all, if that makes sense.

Rick (37:07.069)
I know, to me it feels like for a less annoying CRM.

You've got to, think, to me, like, you can always go the new product route. Like that is always on the table. And then if it works, you can do whatever you want with the old product, right? If you, if you believe, if you have any form of conviction that you can improve the product and get to the next phase of growth for less annoying CRM within the context of being what you are,

I think that that's the path you have to go to. Now that's very broad. That's a very broad statement, but like, then it gets into like, okay, how do you do that? I mean, to me, don't, I have, I always want to look at more data. Like who are you losing? Um, you know, why are people choosing other CRMs versus you? Like these are user interviews and I'd want to like have some conviction around like,

Tyler King (37:56.375)
Yeah.

Rick (38:06.109)
These are the reasons why we're losing those customers. And if we had, if we did this, we have a strong conviction that we would win them, um, even at a $30 package or $15. So that would be kind of my, my math. Um, and I would go pretty hard at that for, I like, I liked your timeline 18 months.

Tyler King (38:22.701)
Okay. And so that's what we did to get a mobile Kanban and automations. Like those are the three really clear trends when you look at cancellation notices and I mean also quantitative, qualitative, talking to people and stuff. And then after that, I have a lot less conviction. This is what always happens is you build, you're like this one feature is everyone wants it. I don't even know what's next. And then you build it and A, nobody cares. And B, you just start getting a whole new set of requests then.

Rick (38:39.869)
Mm-hmm.

Rick (38:51.937)
There's a framework from, I don't know if it's the organization or just the framework's name called Pragmatic Marketing that has like a big circle and then you've got like your slice of customers, your slice of like, and it's like minuscule and then you've got like all the people that were prospects that didn't, you know, that may or may not have bought and then you've got the rest of the market. How much of the rest of the market and the prospects that didn't buy have you talked to lately? Like that would be, that's.

Tyler King (39:19.637)
Yeah, no. Well, but someone who signs up for a free trial and doesn't pay strikes me as the most important person, right?

Rick (39:20.645)
That's where I would go to get the.

Rick (39:28.25)
yes.

Tyler King (39:30.391)
The people who we aren't even getting to consider us, doesn't matter what we're billed, there's still, our marketing, our like top level marketing isn't getting them to our website. I feel like it's the people who are considering us but not going with us.

Rick (39:42.521)
Or yeah, or I would be interested in people who are hitting the website and not setting up a free trial and then go into pipe drive or some alternative because of something you're saying or the way that you're there's quickly saying, do you have this feature or something? I don't know the buying pattern. I know like my buying pattern, which is I'm not your ideal customer profile is like the first thing I look at when I'm going to a CRM is integrations like number one thing. And when we started the podcast, that was a weak point, right? Like you've addressed that.

Tyler King (39:55.202)
Yeah, I agree.

Tyler King (40:05.207)
Yeah.

Tyler King (40:10.463)
No, it's still a weak point. We've gotten better, but...

Rick (40:11.919)
Yeah, but like I'm talking about like my buying, like I can go, you have an integration section on your website. It looks compelling. Like, you know, I'm like, I clicked that in the boxes check. Like that wasn't true a few years ago. now when I get into the actual evaluation, like maybe the integrations aren't powerful enough or that sort of thing, but I'm going to set up a free trial, to figure that out.

Tyler King (40:19.009)
Okay.

Tyler King (40:23.329)
Okay, that's fair. This is a...

Tyler King (40:32.203)
Yeah, that's fair. This is actually an interesting point that on the, on the topic of like one pricing tier reverse two, was talking to Breck and about what, like, what should we build? There's, have a lot of ideas for things we could build that people want. And an interesting point was like, if it doesn't go on the like top five or maybe 10 things list, it doesn't matter. Like to the, to the person you're talking about, who's just looking at the marketing site saying, do you check the boxes and leaving?

If we build something that doesn't make it into that list, we have not affected that person's perception of us at all. And that's interesting. Multiple pricing tiers actually helps with that because with one pricing tier, you get to be like, here's, here's what we have. it's a CRM it's pipelines, know, custom fields. When you have a second one, you can be like, here's another set of things that we have.

which is interesting. Whereas if we build that same thing for free into the $15 tier, it doesn't make the list because the $15 tier already has too much shit in it. That was an interesting, I don't know what to do with that, but that was an interesting insight, I thought.

Rick (41:34.813)
Mm hmm. Yeah. At the end of the day, like where I'm going is I'm kind of going to that sales positioning conversation. Like, who are you for? When I go to the website, like I've hit in the home page and it's like it's you're selling to someone who doesn't want like you're very you're selling to the non consumer, right? Like you're you're saying, hey, like you want a CRM that is powerful, but not too complex and not too expensive and not too much. And we're talking about adding more stuff.

And so there is like, there is like a, like, there is like what there is some at work to do. I've gone like, who are we actually for moving forward? and what does that mean for like what we need to build? have you thought about that? Like we talked about sales last time, but I don't know if you've gone any further on that.

Tyler King (42:19.895)
Yeah. Yes, we have a bit. and yeah, I think I can maybe rephrase what you just said is like our current website is positioning us for the people we're currently getting and it's not positioning us for the people we're not getting. Right. And that that's the tension here is like the people we're not getting want more features. The people we are getting are happy with the features we have. this is another thing kind of similar to the point I just made having a second tier, I think makes that positioning you just said even easier.

So let me pitch you on this. And I should say, like again, we're considering two options. One is keep building the stuff that we think would go in the second tier, but add it into the $15 tier. Like you said, give it 18 months, see if it works. If it works, we don't have to have the second tier at all. And option two is start pulling stuff out, start that second tier right now. Are your kids okay? Yeah. No, that's okay. wonder, know,

Rick (43:11.293)
Can you hear that? I'm sorry. Yeah, no, my kids are high energy and very loud. And people like who don't live with them are like, they're so impressive, but like they're extremely, extremely loud at home. And so.

Tyler King (43:24.365)
I'm curious if the listener will be able to hear, cause you know, Riverside does all this like automatic noise reduction. I wonder if that'll make it through in it. Okay. Okay. I know I have that to look forward to. Sorry. Anyway, the second option is start pulling things into the second tier. It's not going to be a very compelling tier yet, but like it's really hard to kind of break the seal to go from one to two and then over time add more and more to it until it's good. Those are the two basic paths we're considering, right?

Rick (43:29.788)
Yeah.

Rick (43:33.147)
And Tyler, that was nothing, just so know. That was just nothing.

Rick (43:51.969)
And the, yeah, the ideal story here from like a marketing perspective, like staying true to where you came from would be something like we built a CRM for people who hated other CRMs. And then those people hit the limits of that CRM we built. And so we needed to build the ability to scale. And so, yeah, we are all the things we were in the past, plus this additional package that you can add on when you're ready to, to, to, that is competitive with the other pieces.

Tyler King (44:19.085)
So here's the, I agree. Here's the positioning that like I designed a whole pricing page. Just, think that's a good way to think through this as well. The pricing page looked like I actually really liked the way it came out because at the same time, while we have all these people saying, I want these, I want a sales dashboard. I want financial reporting things we don't have. A bunch of other people are coming to us and saying, I want the simplest thing possible. And we need to, we need to tell those people we're right for them. So it's two, two pricing tiers. The $15 tier is called basic contact manager. And the $30 tier or whatever it would cost is called

like sales CRM or something like that. So it's kind of saying the $15 one, it's not even a CRM. Don't even think of it as a CRM because you're not ready for a CRM. And then, if you need these other things that we have, I liked the way that came across, I think. What do you think?

Rick (45:04.955)
Yeah, I said again one more time.

Tyler King (45:06.765)
So $15 is a basic contact manager, $30 is a sales CRM.

Rick (45:14.013)
I don't love, I'm not ready to, I like the idea of doubling down on sales, but I don't know that it gains, I don't know your user flow to know that it gains, I don't have conviction that that gains you anything. don't think, so, yeah.

Tyler King (45:26.645)
Or even just CRM. Even just the idea that what we have now isn't even a CRM really.

Rick (45:34.555)
I think it is. Are you saying? Yeah.

Tyler King (45:35.969)
it is. No it is. I'm saying like to say, what I'm hoping is that the pricing actually improves our positioning for the $15 people. It's not just that it's upselling it to the 30.

Rick (45:46.439)
I agree with that statement, yes. I agree that there is this base package that sticks to your core value proposition of a less annoying CRM. And then you've got to go, I think what we're saying here is at some point you need more than a less annoying CRM. it might be the people, like not today, and it might be in 10 years, but we have that too. Yeah.

Tyler King (45:56.973)
Mm-hmm.

Tyler King (46:13.131)
Yeah, now let me throw a wrinkle in it though. Here's the, so that's how every, every SaaS pricing tier system works like that. It's, this is one product with basic intermediate advanced or whatever. There's a different way to position this, which is the CRM is the $15 tier. The $30 isn't saying we're making a more complicated CRM. It's saying we're like, if you want to stay simple, you don't go deep.

You go broad. say, can't build a more advanced CRM cause that would go against our values. So instead we're building other things. We're giving you a document library. We're giving you web forms. We're giving you scheduling. It's not more CRM. It's the same amount of CRM and more other stuff. Yeah.

Rick (46:54.045)
Yeah, yeah, like I like the idea I do like the idea of like there is one for you for less annoying serum I would probably I'm a principles guy I'm willing to Like go down with the ship over certain things and it feels like staying true to that 15 dot like whatever that base package is is like something that less swing serum Could do right and then it's like okay. Well, how do you build on top of that? And I like the concept of like

Tyler King (47:18.711)
Yeah.

Rick (47:22.877)
the sales package add-on, which includes this, or the marketing section add-on, which includes this, or telephony add-on, or VoIP, or whatever, however you wanna position it. I like that idea. And I would bias towards constraining to that, unless you had to go a different direction after you release it. Because I really don't like the risk to your...

Tyler King (47:42.743)
Yeah.

Rick (47:51.645)
position, your current positioning of going to 15 and 30, for example.

Tyler King (47:56.43)
You don't want it to look like a tear. You want it to look like an

Rick (47:59.803)
I think positioning $15 next to 30 destroys, is highly risked destroying your current and historical positioning and your values.

Tyler King (48:09.655)
Yeah, that is definitely a concern I have. the path it sounds like you're saying we take, which is one of the two main ones we're considering, build, like try and come up with the best list of stuff to build we can, build it all, include it in the $15 tier for now, see if that works, see if the CarPlay thing works, maybe our user growth 18 months from now is looking fine, in which case we don't need to worry about the pricing thing. And if it's not, then we figure out how do we pull some of these things out?

Probably our current customers, the main opportunity cost here is we, I wouldn't feel comfortable charging our current customers who are already using those features for it. So it's saying we don't get to upsell our current customers, but we get to upsell new customers coming in with whatever features we wanna pull out into some other tier or bundle or whatever.

Rick (48:57.831)
The only caveat I would say to that, I agree with what you said, have you thought about like the counterpoint here, which is like perhaps adding more stuff to the $15 package is actually reducing your value prop to the people it originally built for and that maybe you should more proactively reduce what's in the $15 package for new users.

Tyler King (49:12.087)
Yeah.

Tyler King (49:16.819)
we have thought about that and I think the answer is it depends on the feature. So for example, if we added a document library, that would have to like go in the nav bar and like when you sign up and you look at the nav bar, you're like, that's more complicated versus, adding a mobile app. It doesn't change the interface at all. I don't, con band changes the interface, but it's not like a setting it's, it's just, go to your pipeline report and it looks better. So I think some features, yes, some no.

Rick (49:44.125)
So I would just, the only thing I would change is like perhaps with your existing feature set, there's already a $15 plus add-ons that would even make your $15 package more compelling to a new user because it's simpler. So that's the only thing I would call out. And perhaps if you think about it that way, each new feature you add, you're actually scrutinizing, is this actually value added to our $50 package or should it be a standalone product for the right person? Standalone add-on.

Tyler King (50:08.235)
Yeah, I want that to be true, but here's why I think I don't really buy it, which is we're already winning those people. Like no one's even playing in the same arena as us for that simplicity. I'm not saying there aren't more of those people out there. There's like millions that we're not capturing, but we're still not gonna get them. Like they're still not gonna be landing on our website. So I hear what you're saying and I definitely wanna be careful not to lose what we've got, but I don't think the growth channel...

Rick (50:28.605)
Mm-hmm.

Tyler King (50:35.721)
is to go deeper on the people who are already winning, because that's what we've been trying for three years with no real success.

Rick (50:42.779)
Yeah, then I'm getting into like, okay, I think I agree with what you're saying. It's more just changing the way you're thinking about. I think right now you're still in this mode of everything goes into the $50 package. I don't think that, I think it's pretty clear to me that that's not going to change anything dramatically if you just keep doing that over the next 18 months. I think you should, but I do think

Tyler King (50:57.26)
Yeah.

Rick (51:11.697)
you should build additional features. but like the question becomes like, how do you package them? And I'm like, as a result of this conversation, I'm moving very far away from like, tiers. I don't think that's the right play for less links here. But I'm also realizing like, well, we've been at this car play thing for 18, 24 months or even longer, perhaps. We've been talking about it.

Tyler King (51:31.905)
We haven't yet. We haven't done it yet. We've done other things, but not CarPlay.

Rick (51:37.629)
Okay, we've been adding more stuff to the $15 package and not seeing necessarily like any bang for the buck except maybe getting to like from $10 to $15. Comfort. Yeah.

Tyler King (51:48.619)
No, but I think this is what I was saying earlier. Like we have a totally different system now for figuring out what to build. And we haven't shipped any of it yet. We've been working on it, but we haven't shipped it. I'm not saying it will work, but I'm saying we have not found out if it works yet.

Rick (51:54.503)
Okay.

Rick (51:58.833)
Got it. Yeah.

That's fair. I am very interested. I think if you can figure out how to introduce add-ons, potentially conserve and make your $15 per month package more valuable and simpler for the right person. And then you have additional revenue sources and potentially more compelling offers and packages for the other people. And you don't just because like your core pricing page presents in a certain way doesn't mean when you market it or sell it.

to a more sophisticated complex user. You have to package it that way. You could create a separate package that isn't on your pricing page, that is the sales premiere package, not that you would do this, but that you market through landing pages and sales pages that are more of an outbound motion or marketing motion. I like where this is going. I just want to say in summary, I know that we're at time.

Tyler King (53:00.43)
Okay, yeah, I won't share what I took away from that, because we gotta go, but I'll have more updates in two weeks and we'll continue then. Thank you. See ya.

Rick (53:08.733)
Thanks, Tyler. All right, see you later.