Rick (00:00.3)
What's up this week, Tyler?

Tyler King (00:02.369)
Not a whole lot. And I always say not a whole lot and then I have stuff to talk about and this time I really not much is going on. What's going on with you?

Rick (00:10.7)
What is that good? Is that a good thing?

Tyler King (00:13.685)
yeah, no, it's fine. I'm working on stuff. Just nothing's changing. I, we just went through a cycle on this podcast of me having a lot of, big grandiose brainstorming stuff. And then I can talk about this more later, but the conclusion ended up being like, we're not going to do any of that. So now I'm back to just normal day to day work. Yeah. Yeah. Yeah. So we'll talk, we'll talk about that for sure.

Rick (00:31.63)
Well that's a topic of itself, so... Okay, so...

Rick (00:38.578)
Wow, I feel like we've, I can't wait to hear more about what you just said. was like a total, I mean that's just like a morsel of the topic there. But I'm good. I'm just living life. Yeah, I'm trying, it's getting to be that time of year where leg up health business picks up. I mean 75 % of the growth happens starting.

Tyler King (00:39.788)
What's up with you?

Tyler King (00:45.453)
You

Rick (01:06.798)
between October 1st and January 31st and really more specifically like 11-1 through 12-15 and so it's starting to feel that.

Tyler King (01:19.383)
So I feel like every year you say that and I'm not saying it's not true, but what happens, and I'm mostly just saying this so that we can emotionally process it this year when it happens again, then you get to like December 1st and it's all, if I feel like it's always like, well, not, not that much has happened yet. so like, it true that all that growth happens then, or is it all just super backloaded?

Rick (01:43.246)
Consumers are backloaded businesses are frontloaded. So if you think about our like our revenue growth, it's frontloaded like if we're gonna make a huge pop it's gonna be because we sign up a bunch of businesses and Generally that's gonna happen before Thanksgiving because that's when they're making decisions But we haven't done like a huge pop on employers before we've always made like modest gains there during open enrollment So I'm hoping I mean, I'm hoping this year that it's a little bit more

aggressive and I feel the momentum building a bit. Like JD's got some serious pipeline, like legit pipeline coming up just from one, him re-engaging opportunities that didn't close in the past or his out-bounds generating stuff. We've got, I forget what the, I think it's called buyer zone leads, purchase leads that we didn't have last year. So anyway, I think it's.

Tyler King (02:37.728)
I mean, I think the theme of this whole year for Leg Up Health has been shifting from a consumer focus to a business focus. Whether that shows up during open enrollment or not remains to be seen, but it certainly makes sense that it would.

Rick (02:49.848)
Correct. it should happen, I mean, to counter, you're right, first of all, that after 12-1 is when consumers wait till last minute to sign up. If we will know probably, my guess is by the first couple of weeks of November on whether or we're gonna have a good employer season.

Tyler King (03:11.668)
So if mid to late November, you're saying not much has happened with employers in the past that has happened with consumers and it hasn't actually been a problem, but it actually would be a problem this year if that's how things are.

Rick (03:26.574)
Problem probably not, like, disappointment, yes. The thing that happened this year that we weren't expecting was like sort of steady growth outside of the season. what typically has happened is most of our, like we set these goals to kind of double or, you know, every year and we're on track to do that linearly this year, which is weird.

Tyler King (03:28.434)
disappointing like

Tyler King (03:52.47)
Meaning if open enrollment just does the same as the rest of the year, the doubling goal will be.

Rick (03:55.724)
Yeah. Yeah. Yeah. And, and what's hap-

Tyler King (04:00.108)
It's hard not to get greedy when you hear that.

Rick (04:03.23)
Yeah. so it feels, but, but, I, don't know. I just have, I think what you said is true, which is we really didn't focus on employers as the business ICP, ideal customer until really March of this year. And I think we're just now starting to see the impact of that in terms of, messaging outbound pipeline building, that sort of thing. So I'd be very surprised if we didn't bring on.

10 to 20 new employers. But we should actually get clear about what success would be in terms of number of employers. We should get some groups, we should get some free leg up benefits customers, and we should get some paid leg up benefits customers.

Tyler King (04:50.752)
Yeah, I was listening to a different podcast where they were talking about, like the two hosts had different ideas of what goals are and whether you should even have goals and stuff like that. Do you think, like JD is the main person doing the work here. He's doing the sales and the fulfillment and everything. He seems pretty driven. Do you think there's value in talking through like, let's set some goals or something, or is it just like, he's going to go as hard as he can anyway, so let's just let him go.

Rick (05:19.842)
Well, two things. First, think the overarching goal for us right now is get me into the business, right? Like get me to the point where I can afford the consideration of me or more of me, right? And so I think at the end of the day, that's the North Star. And there's lots of different variations of that. It could be me into the business after JD's hired a bunch of people, or it could be me into the business as the next hire.

Like the details don't matter, but that's the North Star. But I think what you're asking is a little bit more granular, which is what about quarterly goals or open enrollment goals? I think it could be valuable for motivation purposes and also just like, I don't know. People work harder, I feel like, when they're being measured and generally. Maybe it's not harder, but more intentionally. I think there's a reason that

the concept of OKRs were popularized, like it creates focus and it creates, you know, constraint, you know, and I think it can be good, but it can also be, there's also a dark side of it.

Tyler King (06:28.79)
think OKRs specifically though serve a slightly different purpose, which is at a large organization, the CEO can't be, they don't know JD, they've never met JD and JD's compensation is not as directly, interests are not as aligned as well. So OKRs are really about like setting a top level goal and how does each level of the company, how does it trickle down into the actual actions that the lowest level is taking?

That's not a concern here, right? It's more just like having that thermometer that's going up for the fundraiser type of thing.

Rick (07:03.534)
Yeah, and I should have been more clear. The portion of OKRs I was referencing wasn't the cascading effect, it was the stretch effect. I think, let me just be more clear, stretch goals could be useful in terms of saying, hey, let's stretch ourselves to try to figure out how to do this to force us to differently and or stop doing other things that we might have done if we didn't set this audacious goal. And I think that could be value.

think it'd be of value is I think JD's money motivated. And so to the extent that we could create some additional monetary incentive for him during the open-rollout period, like that would be kind of a fun thing to think about.

Tyler King (07:45.643)
Yeah, that feels more concrete to me of it could be like as simple as here's a bonus if you hit this number, but even just like this is maybe more the type of thing that relates to me and my role at less annoying CRM is like painting a picture for people of what it would actually mean. Right. It's one thing to say, I want to add 50 users a month or whatever. Well, what does that mean? That means every year we can hire a developer and our product's going to move faster or

we'll start paying for 100 % of health benefits instead of 50 or, you know, it could be something that directly benefits the person. could be something related to just like, you want to be a part of something exciting. But yeah, that strikes me as maybe where goals could be more useful here is just what does it actually mean to hit different numbers here? How's that going to affect us?

Rick (08:32.27)
Yeah, I like that. I like that a lot. Thank you. Yeah, while we're on this topic of goals, I'll just transition into like what I said I would do at the last podcast and what I've done. So there's two kind of big updates on accomplishments. One is I did go through the website and update the navigation and the top above the fold messaging to the group cancel your group messaging. And it's going.

Tyler King (08:36.46)
Mm-hmm.

Rick (09:01.358)
I feel really good about it. So that's phase one. I did realize we already had a pricing page. So I moved that to the navigation and it needs an update, but because it's basically geared towards consumers and saying leg ups free. So that's my next step is to update the pricing page. The other thing that I did was JD is coming to Utah the 7th of October through the 16th. I rented an Airbnb in my neighborhood for us.

so that we could have a really big, not really big, like a big, a comfortable space to collaborate. And I figured it'd be easy for me to go over there and spend the night if I wanted to, or hang out. He could come over here for dinners, the kind of that stuff. And so we're gonna use that time to really get planning done. so in context of the goals, I think I need to do some work.

ahead of that to think about like here's what this means here are different variations of this and we could come out of that with a proposal for the partners

Tyler King (10:08.406)
Sounds good. Yeah, those work or treat things are so much fun.

Rick (10:12.77)
I just gave two updates in one, but do you have any thoughts on the website?

Tyler King (10:17.612)
No, it looks good. My first thought you already addressed, which is like when you go to the pricing page, it doesn't feel right. And you already explained why. I think the navigation is definitely way, way more focused. I know I've said this before, but I, you and I both came of age during this period of abundance in the tech world where companies like Facebook were A B testing every little thing.

and growing endlessly and I got this sense, I don't know if you did, that just like every little detail really matters. And the thing is that's not true. Or at least like maybe at Facebook scale it's true, but it's not true for you or me. Only a few things really matter. And even though you've only touched a small fraction of the website, I feel like you touched 75 % of what matters already. The H1 is way more focused. The Nav is way more focused.

feels a lot better to me. So I know there's still work to do, but yeah, I feel like you've already gotten most of the benefit here.

Rick (11:21.314)
Thank you. I feel the same way. And I was actually like, I put a lot of effort in my sabbatical. I don't know what to call it into learning how to build websites better and design better. And I feel like this was easy for me and I would have not been able to do this in the past. So I just wanted to call that out too. But one little thing that I did was I changed the, I added like a little review snippet at the top.

top above the fold and add it. Yeah, so just little things like that that I'm able to do. And then the other thing is, so the two next steps for me you can hold me accountable to are one, the pricing page, getting that to be business focused and actually useful. And then I'd like to put a landing page on it for get started that is helping someone decide their route and then routing them either to, you know,

Tyler King (11:52.672)
Yeah, I saw that. That looks really good.

Rick (12:19.79)
a forum where they schedule time with JD in a different way or a consumer sign up.

Tyler King (12:29.942)
Okay, the get started page. Okay, right now it takes you to the sign up page. You're gonna take them to some other landing page. The other thing that I, okay, gotcha. And then there's the see how it works call to action above the fold. Is that like, haven't, I'm like looking at this as we're talking, so I haven't read this whole thing. Is this page like where you want it to be?

Rick (12:33.176)
goes to the consumer sign up right now.

Rick (12:37.824)
or the business side of page.

Rick (12:51.604)
No, I was thinking that I would have this page go to pricing. So I was the thing that I took away from our last site is less is more. And I was thinking that pricing should answer how it works. And I was thinking that if they click on see how it works, it goes to the pricing page, even though it's not necessarily labeled that at the top. You disagree?

Tyler King (13:18.346)
probably change what the button says if you're gonna do that. Like it feels like a bit of a bait and switch to say see how it works and then go to a pricing page but yeah I don't think you necessarily need a see how it works. See how it works is just scroll down I feel like. That's the rest of the home page. You don't even need a second CTA necessarily.

Rick (13:24.238)
Mm-hmm.

Rick (13:31.82)
Yeah, could. could. It could. It could.

Got it, I see what you're saying. Yeah, what it could do is instead of going to a different page, just autoscrolls down to the...

Tyler King (13:45.866)
Yeah, or that could be another get started button. Like in the navigation, you have book a call and get started. In the hero section, you have book a call and see how it works.

Rick (13:49.037)
Yep.

Rick (13:55.13)
Yep, and the get started thing will make sense there. It will act as a how it works page anyway once I say, well, tell us more about you. Our approach depends on who you are and that sort of thing. All right.

Tyler King (14:04.213)
Yeah, yeah.

Tyler King (14:09.292)
This might be weird radio for people who can't see the website, but hopefully you can tell what we're talking about. And if you listen to this right away, go look at the website and see what Rick's working on. But it won't be this way for long, I guess.

Rick (14:17.462)
Yes, if you're in Utah and you need health insurance, you know what to do. Thank you. Before we leave the other, the second topic I mentioned, do you have any, you're a really good, I think, in disciplined about doing and setting time aside for these off sites, if you will. When JD comes out here,

Tyler King (14:24.064)
There you go. Yeah, this looks great though.

Rick (14:42.318)
I'm gonna try to take some time off work. I think we'll have a weekend at least that we could work. I'm trying really hard to figure out like, okay, how do I maximize this time with him? Do you have any suggestions for him, for me? There are two priorities here. One is, I think there's three little things. One is spend time together. We don't get to spend time in person. So that could be any kind of time together. could be working out, it could be going to dinners, it could be eating breakfast, having drinks, whatever.

He wants to spend time with customers and prospects. So he's going to be out in the field and partners. And then the third thing is we want to spend time actually working together on the business. So those are like the three outcomes we talked about, but do you have any, any sage sage advice on how to do this?

Tyler King (15:30.477)
Probably not sage advice, but let me think out loud here I think what you said makes a lot of stuff like even if all you do is hang out together That's probably worth it. Especially as we've discussed before Even though this is your business. It is a business that really hinges on JD's morale and just like Giving him that time Even if that's all it does is probably worth it him seeing customers also makes sense so much that the two thoughts

that came into my head as you were talking. One is use this as a forcing function. Actually, it's one thought with two different. Anyway, use this as a forcing function just to make you, work more. Like in a normal week, you have a different day job, you have your family. This is just a time to force yourself. This is what these retreats are for in a lot of ways. And then so the fork beneath that is, well, what should you do if you're working more?

And that's where I'm a little conflicted because earlier you said the kind of Northstar goal is to get you like more into the business. And the main reason for that is because you can do marketing. You can put like scalable systems together to build leads and feed those leads to JD. JD is very good. Once the lead is there, he can sell them, he can service them.

he's less comfortable generating leads. So that's like what the long-term dynamic between you two would be, is you're generating leads and then he's taking them from there. So part of me thinks, well, what progress can you make on that right now? Another part of me thinks, if you're just taking a few days off work, you're not gonna make enough progress on that. And so instead acting as a multiplier on what JD's already doing, which might mean like, can you sit in on some of his calls or go with him to do some of these customer visits and just kind of like coach him a little bit?

And as I'm talking, that feels like the more... thing.

Rick (17:30.476)
Basically, don't try to create more things to do. Help JD do the things we're already doing faster, better, stronger.

Tyler King (17:38.944)
I think, just don't think there's time to execute on like a real meaningful project in that amount of time. What do you think about

Rick (17:46.062)
The only, the thing that we've done historically, and it hasn't necessarily led to good results, is we've put together what's called, we call it an open enrollment plan. And so like, there's kind of two piece, and I think it helps us know what needs to get done. There's a lot of things that need to get done to serve our customers the way we want to serve them. From between 10.1 and, or 11.1 and.

January 31, we've got to update the database, we've got to send renewal notices, you know, there's these little things. And so like, think it's useful to, this is in the bucket of go with JD and coach, sort of. It's more like help JD build a plan for what he needs to do to be successful with what he's already doing. So that kind of goes to the top of the list, I think, because I think it gives everyone peace of mind that.

we know what needs to get done or what JD needs to do to be successful on a base case. But then it's like, okay, well, how do we, where's the leverage to accelerate this plan? And so perhaps like maybe that's where we focus and it could be, you know, helping JD do something better. Coaching is one thing, but even like, let me see your decks. would you like a better template for this deck? Or when you go meet with these customers, do you have like a

Tyler King (19:04.779)
Yeah.

Rick (19:11.27)
One-pager you're leaving behind like would that be helpful? I'm not just like find the areas where JD need actually needs help Or there's leverage and helping him and help him there the one area that I do feel we could benefit from is just like I Really? I've said this for a couple years now, and I just haven't done it I feel terrible about it is we have a number of people that we've tried to sell before and particularly businesses

but like even consumers. It seems crazy that we don't just send them an email saying, hey, you know, we don't want to be annoying, but like it's this time of year. We're better than everyone. Look at our new webs. Like look at all the reasons why we've proven it. We've told you this for years now. If you're going to give us a try, now's the time this year. Otherwise we'll see you in a year. You know, it seems like that would be really low hanging fruit.

Tyler King (19:45.238)
Yeah.

Tyler King (20:01.42)
Yeah.

Okay. I buy that. so that's more in the first category of work I was talking about, but let me like subdivide that into two categories. There's like trying to put systems together, which this is what in partner meetings and stuff like that has come up a lot of like you go into HubSpot and like, let's make a lead magnet and we need an ebook for them to get when they, or, you know, there's this whole like series of steps that generates top of funnel, turns it into qualified leads and passes it to JD. You're not going to do that.

But if there is a single tactical thing you can do, send an email blast to this group of people, then absolutely, yes, I think that makes sense.

Rick (20:41.432)
Yeah, so it's like systems building versus experimental exit, like campaign or touch.

Tyler King (20:46.506)
Yeah. It's not even, I wouldn't even think of it as an experiment. You're gonna do it. It'll happen once. There's no follow-up. Like, there's no learning. I mean, maybe a year from now you'll have learned something from it, but it's just a... Yeah, like, yeah, and it's hustling. Like in this stage of a business, you're just throwing a bunch of shit at the wall. Not everything needs to be systematic.

Rick (21:00.738)
Tactical execution. Yeah.

Rick (21:08.046)
So let's put this into two buckets, say three buckets. There's just basically, JD, what do you need? Let me help you with what you're doing. And then there's like, okay, we've got a bunch of ideas that are tactical execution hustle things. Let's just go through a bunch. Let's try as many of them as we can in the next week. And then there's system building. So system building is off. We're not gonna do any system building. But it seems like...

perhaps this tactical execution and hustle could be the highest leverage for JD. I think the planning thing I think is helpful to him. to me it seems like there's some work I could do on these goals and painting the picture stuff that we talked about at the beginning of the podcast episode. And then there is the plan, which we could probably draft before this thing and just have a quick, are we aligned on this or is there anything we need to talk about?

Tyler King (21:45.376)
Yeah, sure, sure.

Tyler King (22:05.046)
Yeah, the plan only needs to be good enough. You don't want to put any extra effort in

Rick (22:07.052)
Yeah, good enough. And we do it ahead of time. So it's not like something we're building there. And then it's like, okay, how do we, how do we de-risk this plan is like one question. And then how do we, like, what are some ideas to supercharge this plan that we could hustle on this week?

Tyler King (22:25.078)
think, not that you need to commit to this, but five, 10 years in the future, this is still probably true that systems building happens between February and September or whatever. Like this is the time of year for you to stop being a CEO and get in the trenches with the people, which doesn't mean you're doing the exact same work as everyone else. I'm imagining a world where there's like a whole team of people, but it's like, it's go time, you know, lead from the front type of moment.

Rick (22:52.43)
Have you watched War Chief on Apple TV? It's about the Hawaiian sort of history of, yeah, Justin Momoa, I think he wrote it. But he's really good in it. But yeah, he's the War Chief and he is out in front and very funny in the battle scenes. I was just imagining that when you're... No, but he...

Tyler King (22:59.244)
Is that Jason Momoa?

Tyler King (23:09.269)
Nice.

Tyler King (23:15.587)
it's a, is it a comedy?

Rick (23:20.824)
There's a lot of bravado before they spear each other in a battle about talking about how feminine the other warrior is. anyway, that's I was thinking about. Cool, that covers my major updates. Anything going on? Can we start to pick apart what you said at the beginning of the podcast?

Tyler King (23:35.39)
Yeah, go do that.

Tyler King (23:46.765)
Yeah, I think I, it was like six weeks ago. So I, I think I kind of mentioned this, but, um, maybe it didn't like totally have a conclusion, but yeah, like for the last several months, you know, I went through this whole, should we build VoIP? Should we have a second, depending on how you want to package it, but have a second pricing tier or an add-on bundle or a totally separate product, but some way to increase ARPU.

We went through that whole thing. And I think I explained that we decided not to do that right the second, but let me just sum, do you remember this?

Rick (24:25.964)
Well, I don't remember it in that context, but what I do remember, let me just make it move, think, confirm that we're talking about the same thing, is we went down a bunch of different products and whether or not we should have separate brands for that, or it's a feature add-on and then how to package it. And then is it, you know, one price with add-ons or is it packages of, you know, basic growth, that sort of thing.

And I don't think we talked about it again after that.

Tyler King (24:57.032)
Okay. So the basic logic of, of what, like the way I think about that. So first of all, let me summarize. If we were to go that route, where were we when we stopped planning on going that route? That is, I don't think we want to make a totally separate product. Like why, why are we doing any of this? It's not because we want a separate product to market. It's because we've tried everything to grow users and everything has failed. And so the, the main growth.

mechanism that we have not explored is increasing ARPU. The easy money in increasing ARPU is to sell something to our current customers, not to go out and get a bunch of other people to buy something totally different. So from a packaging standpoint, if we were to do this, it would be something like a second tier or an add-on package or something. It would probably be a bundle of things because I think any individual thing being valued by itself,

is like, we could charge five bucks a month for it and 10 % of our customers might use it max. Even 10 is too many, like 3 % might use it. I just think the numbers are really hard to work out, but I think when you bundle stuff together and it's more like a second tier and less like buying out a la carte products, I think that the buying psychology is more like, I want all the features the CRM has, so I'm gonna pay more. That's not 100 % locked in, but that's where we were at the time. But anyway.

Then Bracken and I were talking and like, we just wanted to revisit why are we doing this and not sticking to the old plan? And I just said the reason. The reason is we've tried everything and it's failed. But then as we talked through it more, one thing hasn't failed. It hasn't worked. It hasn't succeeded, but it hasn't failed either. And that is this whole car play strategy that we've been doing, which I feel like every episode I'm redefining or I'm...

Her listeners are probably bored of me defining what car play is. But as a reminder, it's let's there are some key features that are is expected. Every CRM is going to have, it doesn't matter what niche you're in or anything. It doesn't matter what CRM you are. You're expected to have a mobile app. You're expected to have a Kanban view. You're expected to be able to send emails and we don't have any of that stuff right

Rick (27:08.94)
And soon you're going to be expected to have AI, a genetic workflows. I'm just teasing. I just, I just, I just teased that. I'm teasing that.

Tyler King (27:11.25)
AI, well, maybe. No, no, but that's what people, anyway, yeah. So that's actually a great teaser for one of the topics I want to ask you about in just a minute. But so what we realized is we've been working on CarPlay for a while now, but we haven't actually shipped most of the stuff. Like we've shipped email integration for logging emails automatically. That was one of our big, that was our first big CarPlay feature that shipped earlier this year. The next two big ones are mobile app and Kanban. Those are.

well underway, they should ship before the end of the year, but they haven't shipped yet. like, just cause we've been working on this for a year doesn't mean, like we can't say it hasn't worked when we haven't even shipped any of the stuff yet, right? So the big question is will CarPlay work? But I think maybe we were getting, we were jumping the gun on abandoning, like on moving on to the next thing as if this current thing had failed without actually seeing if this current thing would succeed.

Especially, you know, another thing Brack and I looked at is like, are we desperate is a big part of the question here. Is it like, if it fails, we need that we need something to work immediately or elsewhere in big trouble. And the answer to that is no, I was just reviewing all our finance stuff, which I do periodically yesterday. We are, we've got a lot of money in the bank and we are way more profitable than we've ever been before. If you fast forward like years, like three, four years, the money doesn't look as good because our expenses will keep going up.

But we've got plenty of time here. So where we are right now is like, all that brainstorming we were doing earlier this year, actually I still like, I think it could be helpful if CarPlay doesn't work, that is the next move. But we can be patient and give CarPlay time to work, because that's what we want to be our strategy.

Rick (28:59.244)
Yeah, and do you like, this feels like something that the reason that this is happening is you don't have good measurement in place to know when CarPlay is working or what the early signs are. And so you're, because of that, you're, having this ambiguity around what is CarPlay, like not just what is CarPlay, but like is CarPlay working? so that, you, have you thought about like how to actually measure whether this is working and like what?

like defining like what beginning and end is of the carplay you know sort of strategy or like plan

Tyler King (29:27.989)
Yeah.

Tyler King (29:35.585)
Yes and no, I've definitely had that thought that like what you want is an early indicator. So I've said before on this podcast, I think we need to ship all this stuff and then wait a year because I think that's how long it's going to take. It would be nice to have some very, very early metrics of, well, this thing changed and that's an indicator that like that way we don't have to wait a year.

Rick (29:55.778)
I think that's good enough. Waiting a year is good enough. Like that gives you focus. Like we need to ship all this stuff and wait a year. Well, you haven't shipped all this stuff. So the only thing that matters right now is shipping all this stuff. I think that's good.

Tyler King (29:59.371)
Yeah. Yeah.

Tyler King (30:04.944)
Exactly. So, A, we're definitely going to ship this stuff. One of my questions, which I'll ask for real in a second is what do do during that year? And then at the end of that year, if we can give ourselves, like, let's say another year to ship every, or another nine months to ship everything, like this current phase of CarPlay and the next phase of CarPlay, then wait a year, whatever. We're talking about end of 2026, maybe into 2027. I don't think, I don't think the dates I just said add up, but whatever.

If we can give ourselves that amount of time, the answer to your question of what metrics to look at are very simple. It's, we growing? And in particular, I think it's, the free trial or free trial signups higher or sorry, sorry. There's two metrics. The most likely one is the conversion rate from trial to paid goes up. We already have this pipeline of about a thousand people a month coming in, signing up for a free trial. If CarPlay matters, you would expect that to be the most direct thing you can impact. like, Oh, some percentage weren't.

Subscribing because we didn't have Kanban now, you know an extra Three people out of a hundred are subscribing or whatever the number is. That's what we would expect to see Yeah, sorry just that one

Rick (31:15.662)
And then the question becomes, okay, what is CarPlay? Like, I think in this case you're saying we have it defined these features that we need to ship, or are you still adding to that list? Okay.

Tyler King (31:25.726)
Yeah. So, okay. Let's dive into that. That's one of my big topics here is, okay. So I realized everyone listening doesn't necessarily know our product really well, but it's a CRM. The first big one was automatically logging emails. So previously we had this like, have to forward emails to this, you know, in, or BCC them if you wanted them in the CRM. Now you just connect your Gmail, your Outlook account. It pulls them down. That was the first one that launched earlier this year. The current phase is a Kanban view for your like pipeline report and a mobile app.

Anyone who's used a CRM, think that's pretty self-explanatory. Any questions about what I mean by those? No. The next one is the ability to send emails or sorry, there's one other one in this current phase, is automations. These are not the type of automations you are used to Rick. This is a simpler, less annoying version of it. But the basics being I can go to a contact and run an automation manually. like, I want to automatically add my series of seven follow-up tasks or whatever.

add them to groups, whatever. Or you can trigger them when pipeline statuses change. So it's pretty bare bones, but I think it'll satisfy what a lot of people want. The final thing that I feel pretty confident needs to be counted as a CarPlay feature is the ability to send emails, which will include just a basic email composition window, nothing too fancy. then the reason this is so important, because you can right now click on a contact's email address, it opens up a Gmail window and you send from there. It's fine right now.

But the reason we need to be able to send emails is so that then you can connect them to automations.

Rick (32:59.136)
and templates.

Tyler King (33:00.798)
and templates, even that, you can do templates in Gmail, can do templates in Outlook.

Rick (33:05.142)
No, I mean like field-based templates.

Tyler King (33:07.806)
Yeah, that's fair. This won't be bulk emailing though, to be clear.

Rick (33:10.988)
Yeah, just, but like I'm saying, like if you're sending us a standard follow up email to someone after a call, when they just reach a certain stage in a CRM, like having a template pre-populate is pretty standard. That's happening usually in like a business of my size and a different tool that's connected to the CRM. But I would say that, for example, HubSpot, if you're composing an email, you can customize the email.

Tyler King (33:34.475)
Yeah.

Rick (33:39.382)
have the email prepopulate based on the record that you're sending to, information that you've collected. Yep, okay.

Tyler King (33:46.411)
Yeah. Fair enough. Yes. Agreed. And that that's definitely on the, you have to have templates in order to do email automations, right? Because the automation is sending a template. so, okay, we could stop there. Like I, it's pretty clear to me if we don't have those things. Well, a, those things are all expected for any CRM to have, and they're not like beyond the scope of what a less annoying CRM should have. the concern is that, okay, what about after that?

Rick (33:53.624)
Yep. Yep, yep, yep.

Tyler King (34:16.938)
I have two concerns with continuing down the car, even if car play works, whatever that means. A like each additional feature presumably has less impact than the last, like assuming we did a good job of picking what these features are. Okay. Well, what's the next one? I don't know. Better reporting maybe. Well, okay. That's not going to have the same impact and on and on and on. And B if we just keep adding these features, we're, we're no longer less annoying CRM. We're just shitty HubSpot or whatever. I want to protect our simplicity. So.

I'm a little nervous about the idea of like, we just keep doing carplay forever.

Even if we do, should we, is that what we should, there's that one year waiting period where we don't know if CarPlay has worked yet. What do we do during that year? So I have thoughts and all that, but I'm curious what your initial reaction to that is.

Rick (35:08.222)
So when you were talking you said you had a thousand users per month I Want more users per month so like carplay to me is not necessarily going to bring more use per month I think the primary metric is the free trial to paid conversion. You're basically Systematically addressing the reasons people don't convert into paid users through carplay. And yes, there might also be more word of mouth, but I think it's very hard to manage that so

And message and know whether that's working or not because there's like so many other variables into the traffic so to me like the if you finish the carplay stuff that The next thing has to be focused on actually driving more leads

Tyler King (35:51.437)
Do mean the next product thing though? So here's, I agree, except again, we've tried everything or I have no remaining ideas for that aside from, well, why do we get the thousand leads we do now? Good product, good brand reputation. So I agree and I'm very, very interested in if you have any ideas there, but we hired a marketing strategy firm, every idea they gave us we're already doing. We, you know.

Rick (35:53.354)
The company focus like like it. Yeah.

Rick (36:05.55)
Mm-hmm. Yeah.

Rick (36:10.786)
Yeah. Yeah.

Tyler King (36:19.574)
We did all the last two or three years, a lot of our product, tried product led growth in a lot of different ways. We tried the viral thing. I don't know what to do on that front at this point.

Rick (36:28.662)
Yeah, so to the extent that you are doing everything that I guess that goes away. But that's where I just, it feels to me like the things that you can do, anything you can do that will help with getting more eyeballs and more new people interacting with the brand should be next. And that doesn't seem like CarPlay to me, that seems like something different. It goes back into the realm of how do you provide tooling to customers that

exposes the less annoying CRM brand to other people. Appointment scheduling, you've already got forms, but like maybe it's like more use cases for forms, but you have a low adoption on forms. like the thing that has been interesting to watch, let me just take a step back, is I think when I was talking to you about this a year ago and we were like, yeah, you should do these things. I saw the risk and like what was hard here was building the product, not necessarily.

Tyler King (37:11.041)
Yeah.

Rick (37:26.968)
getting people to use it. And I think that that's something I've learned watching you is, yeah, you could build up, first of all, building the product's hard. But let's say you do that. It's just like battle one. The second battle is actually like getting your existing users to use it.

Tyler King (37:39.68)
Yeah.

Tyler King (37:43.861)
Right? Not even new use. Like for a brand new startup, it's you have to build a thing and then you have to get customers, which is much, much harder. It's hard even when you've got 25,000 people using your product every day just to get them to use the new feature. Yeah. It's crazy.

Rick (37:45.656)
Yeah.

Rick (37:57.932)
Yeah, yeah, so that's, mean, I didn't think about that. That wasn't really a huge consideration when we were talking about this in theory, but after the forums thing, I was like, man, this adoption stuff's hard. But I just, wonder if, I don't know, I wonder if the reason that adoption's hard for you is the same reason getting new leads is hard. Like, it's just maybe these things that you're not comfortable doing to drive demand. Could be, like, there could be some similarities there, but anyway, I don't have good answers here.

Tyler King (38:26.262)
I think with adoption, really tried. Quick side note, by the way, forms is actually still growing. Adoption is still growing. I forget if I shared this on the podcast, but it's something like 1 % of users are using it, but it's like 5 % of new users or something like.

Rick (38:41.07)
That's promising. That also tells me is that you've got 4 % of your existing users that are missing out on this thing that is probably due to a lack of awareness slash, yeah.

Tyler King (38:55.466)
I don't think it's awareness. We pushed it really hard. think it's inertia. I'm sure you do this all the time where...

Rick (39:03.384)
When you buy a new tool, it's easier to adopt new workflows. When you're in your workflows, what's the event that causes you to change your workflow? It's hard. Sorry, I didn't mean to interrupt you. Yeah.

Tyler King (39:06.358)
Yeah.

Tyler King (39:11.564)
So we're still pushing it and no, no, you're absolutely right. We're still pushing in the newsletter and stuff like that, but this is one area where we have not been shy. We've put ads directly in our app for people to see. We've email blasted people. You know, we've, we've done the things we could think of to do. And I think like, I think 10 years from now, we're going to look back and say, forms actually did kind of work. I don't think it's like the solution to all of our growth problems, but I think we're going to look back kind of like our affiliate program is right now. We're going to say, you know what? I'm glad we have it now. Like that's a.

a brick in the wall of our growth strategy.

Rick (39:44.91)
Yep. Do you have ideas on what happens after CarPlay? Like, do you have a about anything?

Tyler King (39:48.535)
for pro, no, let me, so let me run through those options. I also want to address the growth thing. I don't want to give the impression we're not working on growth. We are working on a new user community forum. We're talking about some improvements to like our partner programs. We're talking about a new YouTube thing. So we are doing things there. I just don't think any of it's going to work. On the product side. Okay, so car, more car play is one thing.

One option is to say, let's assume CarPlay is not gonna work. Let's start, and in which case we've already, I don't wanna say decided, but we are leaning towards that additional like increasing ARPU product bundle is next. Let's start building whatever we think would go in there, but launch it for free for now. This is what we're doing with automations. I think automations would probably be a premium feature depending on how we package that extra tier.

but we're just launching it for free for now to see if that helps growth or conversion rates. But then we can pull it off into a higher tier later if we want to. So one thing we could do is say, what would the features be? Let's get started on them so that we're ready to go the moment we've decided CarPlay fails. One thing is to really, really focus on onboarding type stuff, which I partially mean the actual onboarding experience, but also, you can like go look what...

Actually, very similar to what you're doing with your marketing site. People click on the pricing link first. What do people click on when they sign up for a free trial? What are the pages they actually see? Let's just obsess over the design of those pages. We are probably today or tomorrow are gonna ship a new signup process because we've already started this a little. That's just like, it's a little sexier to give a really good first impression. I think there's a lot of stuff we could do there. And then the final category I've got here is just cup holders, which again, I define as just like little quality of life improvements for our current users like

If we don't have clarity around what our product strategy should be, the safest thing is just to make our current customers happier. And we have a long list of things that we have very high confidence would do.

Tyler King (41:56.567)
So those are the main categories I've got.

Rick (42:00.174)
man, they're all good. I don't have, the good, so here's the, I think all these are good. I think like I lean towards like if I was gonna start taking things away and focusing, would probably alter between the middle two that you mentioned, starting to prepare for charging more, because I think that could lead to some more intentional higher impact features and then also like revenue. And then,

Tyler King (42:01.6)
You

Rick (42:30.456)
the onboarding initial impression. So I would probably go parallel path those two things, because they're very similar. The reason that I like the charging more thing is twofold. I've said this a couple times and I just wanna say it again, which is I still think that figuring out how to drive more users to the site is ultimately like the long-term objective that is going to be like the thing that you need to solve. And charging.

more opens up new possibilities. So I do think like, while it's not directly like, how do I increase visitors? You having a package that is more expensive that could fund more, I don't wanna say aggressive, like expensive lead generation campaigns is something that is interesting to me. And we've talked about this a couple of times, but like, just, that's probably, yeah, yeah.

Tyler King (43:23.828)
Yeah. You do keep saying it and I keep forgetting it. I keep thinking, well, how does having a higher price generate leads? And I keep forgetting, cause you have more money to spend. Yeah.

Rick (43:32.91)
could spend more money. And so that one is probably the one that I would bias towards. But I could see how maybe to wrap up CarPlay, you go and focus on onboarding initial oppression just to maximize the free trial conversion right there before you move to that. But so I think all of these are good. I guess I'm trying to say anyway.

Tyler King (43:52.055)
Yeah, yeah. So here's a number that might, the onboarding stuff is the most boring from a product. It doesn't really provide much value to, it provides zero value to our current customers. And it doesn't even provide much value to our new customers, except for the ones that wouldn't have signed up and paid us otherwise. Like an example being, get your Google integration set up during the signup process so that the first time you see your CRM, you've already got stuff in there. But like,

The alternative is you sign up and then you go set this up. It's a lot of extra work to do it the new way, but it doesn't really provide value. But here's a number that makes it sort of compelling to me. We're converting something like 20 % of our free trials to paid right now. Yes, it's good for no credit. I think it's bad if you have a credit card upfront. It's good if you don't have a credit card upfront. One thing I'll mention though, we have this like live demo thing on our website. So people get to try the live demo.

Rick (44:36.43)
Pretty good, right?

Tyler King (44:50.954)
without signing up and then, and not everyone does, but a lot of people do. So a lot of the non-fits don't sign up for the free trial because the live demo didn't work for them, which maybe that's another avenue here is like make the live demo even better. Anyway, yeah, I think 20 % is pretty good. It used to be more like 25 or 30%. It's kind of slowly gone down over the years. If we got from 20 to 25 or whatever, if we got a five percentage point bump, our growth problems are solved. We don't need anything else.

sure. Yes. But when I say, so, mean like solved as in like, we can start hiring devs again. We can start investing more in marketing. Like we're a different company with an extra five point conversion.

Rick (45:21.176)
Short trip for now.

Rick (45:35.246)
You can switch back to offense. Okay, so here's some thoughts. I think the onboarding and initial impression potentially is something, I don't know. Let me say this. I think number two, the start prepping for charging more slash packaging is where you should focus next. Yeah, let me tell you why. So I think this.

Tyler King (45:37.322)
Yes. Yes.

Tyler King (46:00.215)
Can I? sorry.

Rick (46:05.386)
Ultimately, if you're serious about that, if you focus on it, you will get to what you need to do and a clear path and you either will see it happening in two years or in one year or three months. Like it'll be some sort of timeline to it. And then you're going to go, okay, so there's all these other things that need to be true in order for me to do that. So now I'm working on that. Meanwhile, I need to go focus on the onboarding and initial impression. I, what I worry about is like there's the, if you don't do that work, it does impact onboarding and initial impression. So

Tyler King (46:35.274)
Yeah, sure.

Rick (46:35.278)
You could end up doing a bunch of onboard initial impression work come back to that and you're like, well We're closer to this thing than we thought now. We just spent you know, I've Months updating an onboarding in an initial impression process that actually is we need to redo anyway because we're gonna have packaging Anyway, that's that's the logic. Go ahead

Tyler King (46:50.646)
different.

The thing that scares me about it or the reason I'm gun shy is like, the hope is we never add that second tier. Like one of the things in all this brainstorming, one of the big things was like, man, we hate what this does to our company. A huge differentiators are simple pricing. It would have us build a bunch of features we don't really want to build. If CarPlay works, it's not like we're going to do that eventually. It's a question of when it's like, we hope we never have to do it.

Now the features we would build we would just offer for free forever. It wouldn't be the end of the world, but that's why I'm a little gun shy.

Rick (47:25.806)
Well, that, okay. So like, yeah, I would divide these ideas into two buckets. Buckets that enhance car play and we would prefer the route we prefer to go if car play works and we don't have to go do these other things. And then bucket two of like, we are worried car plays not going to get us there. We need to try something different. And then you have a different path. You have kind of like this, this backlog of things. That's like, if we want to pull the E brake, this is where we go.

the other thing I was thinking about, I don't know, I feel like he benefited in the early days from, I don't wanna call edginess, but like less annoying-ishness. And I don't know what to call it. Yeah, being different. And I'm just wondering, have you really thought about enhancing and doubling down on that from a word of mouth perspective? There's so many different ways to create content now.

Tyler King (48:09.643)
We were different.

Rick (48:23.734)
and promote content in a brand awareness way more so than like a demand capture or gen way. And I'm just wondering like, if you just focused on getting more people to know less annoying CRM and the humor behind it and the story behind it, eventually, like if you do that strategically in the right places with your, where your people hang out, know, is that worth like a long-term bet of like spending, I don't know, 20 grand, like what you would spend on a full-time marketer every month?

just like telling people, like giving people interesting, funny, educational, humorous, edgy content. That's just another idea that I would have that you spend a bunch of money on it and not work, but like it would be, you wouldn't feel bad about it.

Tyler King (48:52.864)
Right.

Tyler King (49:05.324)
I. It's really appealing to me and we've tried things like this in the past. Like less annoying business was meant to be one of these things. I think of everything you just said, the one that I've gotten stuck on is the where people hang out. 37 signals or I guess they want, yeah, they're called 37 signals again. they have like this community of kind of.

tech adjacent, buildery, kind of marketing agency type people, and there's, there's community and you know, whatever. We have invested time in trying to figure out, like we've surveyed our customers and talked to them and all that. Like, where do you hang out online to try and find where the communities are? And the answer has been there aren't any. That doesn't mean they aren't consuming content. I fully acknowledge that, but I've never figured out who to talk to and where with this content.

Rick (50:01.966)
Interesting. Yeah, it's like, you don't want to boil the ocean. But here's the thing, like this is what we do at WinFall. Like what WinFall does, so WinFall is a consumer data company. basically can't, most of it's focused on helping organizations target consumers. But the concept applies to businesses as well. And so there are ways today to identify an audience that is less annoying CRM target buyers, let's call it.

And we can, can have an online audience and an offline audience. And the offline audience is more around like direct mail or, you know, knowing where they live or work and that kind of thing, door knocking, that kind of thing. And then there's an online audience, which is like, we want to, if one of these people in this audience are on Twitter, we want to show them, you know, a sponsor, sorry, not Twitter X, we want to show them a sponsored video, you know, that kind of thing.

And so you can't, I think there are ways in which you can worry less about where they hang out and, focus more on like who they are and then, uh, experiment across different channels, um, or, uh, platforms, uh, to, to, to introduce the content and you pay more for precision, right? Like the audience is smaller. Uh, so you're going to pay more per like impression or click, but you know that you're getting the right person to watch the video or interact with the ad.

And so I think that that could be something worth exploring at some point where it's like, hey, we're gonna go, and then what's the, I think right now the challenge that you're gonna face is, okay, they're not ready to do a free trial. So what's the call to action?

Tyler King (51:47.628)
Yeah, cause we've definitely done this like let's go on Facebook and target, you know, like insurance agents are a really good fit for us. Let's go make, make some.

Rick (51:57.966)
So this goes back to the community forums and it does feel like you need something that is a value like content or community or something of free value that is widely applicable, which goes back to the annoying business idea. And so I do feel like there's probably, there's something there is all I'm trying to say that probably should be the focus for a marketing team at less annoying CRM, which is what is this free,

pre CRM product that any, whether you buy less knowing CRM or not, it's valuable to you. And then how do you get people to join that community that aren't less knowing CRM customers? That's probably the bucket of thing that I would, that's the marketing plan in my opinion.

Tyler King (52:41.932)
Yeah. I don't think when you, you said join that community, the pro like this relates, we need to end this pretty soon, but this relates to a different topic on my list, which is like we've, we've teased in the past of should we be positioning ourselves more as like a sales tool and like, cause right now are the type of person I said, insurance agent or travel agent or business coach.

They don't hang out together. They don't have that common thread. Salespeople maybe do. I don't know the answer to that, but like that's one of the big problems that our customer base right now isn't one like well-defined type of person.

Rick (53:26.104)
I would suggest that we deep dive on this another time, because I think we're just getting to the actual thing here. One final thought is content. If there's not shared community, there's content that is of value. And I was just like, this is just a random idea that we could noodle on. How to be less annoying at your job. How to be a less annoying salesperson. How to be a less annoying business coach. That's ultimately value-added content that helps them do their job. And if you had...

that type of content, I think it would bring people into the brand. Anyway.

Tyler King (53:59.69)
Yeah, we've tried that so many times, but that doesn't mean we tried it well. I mean, we might've executed poorly, but anyway. Okay, we are out of time. All interesting stuff, I added a little bit for a future topic. So thank you for all that, Rick. That was helpful.

Rick (54:01.94)
Okay, I didn't know that. Yeah.

Rick (54:14.294)
If you'd like to review past topics and show notes, visit star-up-to-last.com. We'll see you next time.

Tyler King (54:18.253)
See ya.