Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.
Rick (00:00.536)
Tyler, what is up this week?
Tyler King (00:01.817)
Rick! Not much, Yeah, just a normal week for- I know right before you started recording you were asking me how I'm doing and I just have absolutely nothing to say about myself. I'm absolutely even keel across the board here. How are you doing?
Rick (00:16.95)
I'm well, you know, you know, when you've you're going through like one of the harder projects and you're I've had a couple of like projects in my career over the last 20 years, 20 years. I said that out loud. Yeah. Where it's just like, I don't think I can do this or this is way too hard. And then when you come out on the other side of it and it goes well or it goes well enough, I should say, you have this like euphoria of like, holy shit, like I feel so good.
Tyler King (00:28.071)
Don't say that. Shut up.
Rick (00:43.842)
I'm having that right now for some work I've done and it feels really, really good. Yeah, went full stuff. It's so ongoing project, but the first phase of the project, the context that I can share is it's basically a highly urgent, important project with very limited time constraints. And I had to get up to speed, you know.
Tyler King (00:49.341)
That's cool, this is windfall stuff.
Rick (01:12.184)
get it, get it going and then get, get moving on a couple of things. And it's, it's gone. It was very hard. and, but I, but now I've like got it. passed the point of like it being a question and now it's like rolling and I feel so good.
Tyler King (01:19.092)
Yeah.
Tyler King (01:26.717)
Hmm, that's cool. Where my head goes with that is like, think it's been a while since I've had a project like that. Which kind of maybe bums me out a little.
Rick (01:38.018)
Well, it's a trade off, right, between building a calm company, I think, and maybe a more chaotic or default dead company. And so I think, yeah, sure. I don't know, what do you think about that? Why don't you set yourself up for that?
Tyler King (01:42.674)
Yeah.
Tyler King (01:52.486)
Yeah, being more ambitious.
Tyler King (01:59.763)
Well, so like I have goals that are like that, but I don't think I have individual projects. Like getting our growth better has I've been working on for years and without a lot to show for it. And so in that sense, like that's a goal that I don't know that I can do or, know, I, still am optimistic that I can, but I haven't yet, but each individual project towards that goal is like, you know, okay, let's, build this feature or.
try this marketing channel and like the individual projects. I mean, some of the features are harder to build than others, none of them are like, don't even know if it's possible for us to achieve this, you know?
Rick (02:39.924)
Mm-hmm. Yeah. Yep. Do you think like, do you think like the cost of projects like that? It's on some frequency are healthy, like I guess like there is a huge cost. Like it was a very difficult, it like, you know, cascades to the family, you know, it affects like sleep, exercise, like there's like a pretty, you know, negative toll. But on the other side of it, it's like that.
Tyler King (02:43.121)
I mean.
Tyler King (02:54.033)
Yeah.
Rick (03:07.884)
that relationship seesaw between pain and pleasure. you go, the pain hurts, but then like on the other side of it, like it flips to, you know, really awesome euphoric feelings when, when you get over it.
Tyler King (03:10.962)
Right.
Tyler King (03:19.825)
Yeah, you don't want to be the people in Wall-E, who I've actually never seen Wall-E, but do know the reference I'm making? There's like, I don't know, it's some future civilization or something. Again, I haven't seen it. But humans are just like fat blobs sitting on lazy boys and the lazy boys can like drive around for them and they're just like staring at screens and you know, there's zero challenge. It's just absolute comfort. Obviously when I say I run a calm company, I don't mean like that calm.
Rick (03:25.1)
I don't.
Tyler King (03:48.911)
So it's still challenging, but yeah, I totally agree. None of this is fun if it's too easy. Yeah, I kind of think maybe just like the SaaS game is more mature now and there's still lots of interesting stuff to work on. I want to give the impression I'm bored or anything, like whatever feature, like I could make up features that would be, can we even do this? Can we execute on this? None of those are the features that customers need. Like I think it would be.
the tail wagging the dog to try. It's not like I have a bunch of these things and I'm avoiding them because I'm scared or it's too risky or not calm enough. I don't even know what the project would be that where the payoff would be worth it, you know?
Rick (04:30.86)
Yeah, the company has to present that opportunity, right? And there are stages, there are companies that don't have that opportunity and actually it could be counterproductive to the success of the company by trying to create those opportunities. Like that might be your situation.
Tyler King (04:44.999)
Yeah, yeah, there are a lot of boring companies out there running a CRM is pretty boring. think probably like up health is, mean, you, you could turn it into something a little more cutting edge or whatever, but at least technologically, I don't think it's all that exciting.
Rick (05:00.502)
Yeah, well, totally. And I'm getting kind of comfortable with like, you know, one of my other updates is that JD's rolling right now with, you know, building employer pipeline and and hitting executing against our financial plan. And it's it's because we calm things down. And so I actually I believe that like the distraction for leg up health of like high stress actually leads to better worse client interactions, less.
less deals getting done. It's actually like counterproductive to like a good insurance agency. So I think there is anyway, it's I don't think all companies should force this.
Tyler King (05:44.263)
Yeah, well, you want to segue into that? You want to give an update on JD?
Rick (05:46.134)
Yeah. Yeah. So JD's like killing it, man. Like I just pulled up the employer pipeline. We have five new employer customers onboarding to a paid or group health insurance commissioned offering. And we have another 10 or so in like qualified deals and pipeline. And as you may recall, we have one, one, our target is one deal a month to hit like one, setting up one employer a month.
Tyler King (06:09.394)
Yeah.
Rick (06:15.336)
for the rest of the year to hit our growth goals. And so like we like we have the pipeline right now to do like half of years worth of work.
Tyler King (06:22.769)
And okay, let's dive into this because in our partner meeting this month, I know we talked about this two weeks ago in our last episode, but earlier this month we had a partner meeting and just to summarize what our last conversation was, there is this Kanban board and pipe drive with like 80 cards in it or something, like a ton of cards, but then you were kind of picking it apart and being like, that's not a real opportunity, that's not a real opportunity. And JD basically went in and deleted almost all of them. I think there were only one or two real opportunities in there, right?
So how did we, and at the time I think it was a bit deflating cause it was like, it went from, look, there's 80 things on this pipeline to, there's two things on this pipeline. Fast forward just a few weeks and now there's 15 things on the pipeline. What happened?
Rick (07:03.702)
of focus in my opinion. haven't really debriefed with JD on this. I think that's a good thing for us to do on Monday. But yeah, I don't have a good answer. The, been a path leads, been a path leads. Yeah. And, and net, and network, like sort of existing relationships focusing on that. I don't think any of these are cold based on what I'm seeing.
Tyler King (07:14.147)
Do know where they're coming from? these new cold outreach? Okay, this is the buying leads from a lead generation.
Tyler King (07:28.611)
Okay, they're not cold, but they're not anytime. There's a big surge like this like in the past of leg up health every once in a while like Rick you'll be like, you know what? I have some contacts I'll call them up and ask them if they want to become a customer or you kind of like you have this finite resource of Favors to call in and you do it and then anytime that happens. It's like well, okay great That's a nice win, but it's not sustainable. This sounds like it's gonna like there's why won't this happen again next month?
Rick (07:55.042)
I think we should talk about it more in the partner meeting. I can make a bunch of assumptions. think this is the new standard and I actually think it's going to get better, not worse. And I think two things are happening. One, I JD was, I think any salesperson, founder, if you're in charge of sales, if you have too much stuff that you're looking at, it's overwhelming and paralyzing. And you end up actually not moving anything forward or very little forward.
When you shrink that and you get focused on what's really real and you actually give yourself permission to say, this is not a real deal. I'm going to focus elsewhere. And I'm just going to nurture this over every 90 days or so you, you, you, you end up realizing, that's the real stuff. Number one, you start moving that stuff in or forward or out. And then you also realize, there are these, all these other opportunities that I wasn't recognizing.
and tracking because I was so distracted by all this bullshit. And so I think that's probably the biggest thing that's happened is like JD had real opportunities that he wasn't tracking his opportunities. They might be upgrades for existing customers. They might be intros that he's taken that he's kind of just like going slow on. And he got, think those have become like risen to the, to the top, if you will.
Tyler King (09:12.467)
Yeah. The other thing I took away from the partner meeting, a thing you said that like, when you say it, sounds obvious, but I just don't think it occurs to everyone necessarily. And I don't think JD was doing it as like that first qualifying call. Cause you kind of said, okay, stop like JD was skipping the qualification and moving straight to the train, the sale. I kind of, I don't want to say I pushed back, but I was trying to learn from you why that's necessary. Cause I, in my mind, qualifying, by which I mean like getting on the call to make sure they're a good fit rather than just trying to move them forward.
In my mind, qualifying is for when you have too many leads to handle. and you were saying, no, even if you're dry on leads, even if you don't have that many, you still do the step. And one of the key things I took away that you said is in that call, you say, Hey, can you commit to making a yes or no decision by the end of the month? If not, no problem, but we're not going to follow up right now. so they don't get that. None of the value gets provided until they say, yes, there's a timeline because JD had a lot of these kinds of.
cold leads that were just in limbo. And it does seem like the fact, not just that he has 15 leads now, 15 real opportunities, but the fact that those opportunities all have a timeline and they'll either, we'll either win them or lose them within the next month. That is the big difference to me.
Rick (10:26.242)
That's a good point. Like, what that's a, that's another thing that happens when you have too many opportunities as you, as you, lose the discipline of like formally entering in to a sales process with the customer, with the customer's agreement. And that's in sales, like there are different terms for this. There's trades or like, upfront contracts is the Sandler term, but basically the way I like to think about sales is the first meetings is all about like,
feeling out, adding value while you feel out whether you can help them. And then if you can't help them, you tell them, right? And you don't enter a sales process. If you can, you say, here's how I think I can help you. Here's how I propose. I try to help you in order for me to do that. Here's what I ask of you. And that could be make a decision by the end of the, but by this date, or it could be you're going to agree to this time, you know, this next step.
And then the next, you could even outline the next three steps and say, you agree to go through this process. And if you can't, that's okay. But then they self-select out or they move forward in the process. There's really only three outcomes. I can't help you. We agree to move forward with our sales process or three, you are not ready to move forward with our sales process, but you understand that we can help.
Tyler King (11:44.689)
Yeah. Yeah. It reminds me. Yeah. I've had so many experiences at less annoying where people will waste your time if there's no cost to them to do it. and I'm not saying these people were deliberately doing it, but like the, this is kind of a totally different scenario, but it just reminds me of it. When a customer like is interested, but they send in this big Excel document. That's like a security questionnaire and it's like a hundred questions and it's like,
describe to us where your servers are located, describe to us your encryption policies. It's like this huge survey you have to fill out. They'll make us do all this work because it costs them nothing. If we just send them and say, here's a link to our security documentation, can you let us know which questions aren't answered there and we'll get them answered. They never do it, zero out of a hundred times do they do that. Because you've said, hey, you were happy for...
us to do this work, but as soon as you have to do anything at all, you realize you don't even care about this. It doesn't even matter to you. And so, just even in the case of JD's like kind of new sales process, he's not exactly making them do work, but he's saying, hey, you need to be on the timeline here. You can't just drag us along for it.
Rick (13:00.812)
In other words, this is not free. I'm not gonna charge you money for this, but my time is not free. I require an agreement of sorts that you will hold. And just so you know, if you can't hold the agreement, not a good customer for us. It's okay, we're willing to walk away.
Tyler King (13:03.367)
Yeah, yeah.
Tyler King (13:18.727)
Right, right. It's crazy how big of a difference this has made in less than a month.
Rick (13:23.15)
Yeah, the other thing I want to call out that I just want to give you some credit for is JD and I did our normal annual planning in February and we came with a 100 % year to 200 % growth goal and you're like guys What's the what does the world look like if you just like continue to do what like, know you can do and like why don't you just build the budget and the base plan based on that and we could have goals and all sorts of aggressive things above and beyond that like that we we talked about but like
Let's just create the base case that's like not stressful. and I think that that is like having a huge impact. Every time I call JD, like his energy is just very positive and, he stressed about the right things. Like what does he, what stresses in the right word? He's worried about the right things versus this, this, this, this, this goal that was only intended to motivate, but actually has the negative impact. anyway, I just want to call out that I think that having,
Tyler King (13:54.419)
Mm-hmm.
Tyler King (14:09.489)
Yeah.
Rick (14:20.332)
Meaning like reasonable, like not stress inducing goal, like base goals, is having a huge impact on his ability to focus and do the right things in the short term.
Tyler King (14:29.651)
Great. I love to hear that. Yeah. It I've talked to or listened to podcasts or I've heard from so many founders that kind of there's this circular logic going on in a lot of bootstrap startups where it's like, all, you know, I'm in general kind of anti-selling, not that, you know, it makes sense sometimes, but like, I don't like the fact that companies start with the intention of selling the P a lot of people are like, no, I always start with the intention of selling because I know it's going to be too like.
this I'm gonna burn out, it's too stressful, I don't wanna do this forever. But then if you examine why it's so stressful, it's because they feel like they have to be able to sell for a certain amount of money in a certain amount of time. I just feel like so many founders are trying to create this outcome, like this destination, rather than just saying, can we make this the job I want right now? Am I already at the destination? Yeah, yeah.
Rick (15:21.378)
Is it is a default right? that's like and it's not saying like you're not saying which I want to be very clear is you're not saying don't set aggressive stretch goals Above that you're saying default alive default base plan not crazy And then and that you like and that you're happy with and then it's like, okay, you want to stretch? Let's set a goal for the next three months that we we do above and beyond that that ensure, you know supercharges past that I'm finding Yeah, exactly. Not because you have to
Tyler King (15:36.316)
Yeah.
Tyler King (15:46.865)
Yeah, you do that for the love of the game though.
Rick (15:50.432)
And it's a totally different feeling. What I'm finding, and I don't know if this is true, is that that stretch goal may not be necessary when you have the right people and you don't stress them out. They'll set their own goals. And so I think that's a big, observation or learning for me.
Tyler King (16:04.605)
Yes.
Tyler King (16:08.147)
That's a great point too, sorry to belabor this, but so many of the mistakes bootstrappers make, or just small businesses in general make, is they look at how big companies do it and then they try to mimic that. At a 1,000 or 10,000 person company, that new hire you just hired on the sales team who will never meet the CEO in their entire life, that person needs goals and metrics and KPIs at a three person business where two of them are part time.
Rick (16:35.725)
Yeah
Tyler King (16:36.935)
Hopefully that one full-time person is intrinsically motivated.
Rick (16:40.046)
It has the context to set the right goals. So yeah, exactly. Tell me about you,
Tyler King (16:43.334)
Yeah, yeah.
Tyler King (16:47.595)
yeah, I don't, I had some, some banter for the beginning and we blew right into the, the meat of the stuff. So I'll go back to banter here. we're on Riverside now we're recording this podcast on Riverside. You don't listen to our, episodes, do you?
Rick (17:04.83)
I want to. I don't want to say no because it's not true. I do occasionally but like I don't do it like I used to listen to everyone religiously when I had like space to do that but I haven't done that in a while. Is it bad?
Tyler King (17:06.739)
Occasionally.
Tyler King (17:15.581)
Yeah, well, I listened to our last one, which is the first one we recorded with Riverside and I thought it sounded weird. I'm curious if anyone else noticed. It's also possible I did something wrong. So we've been using ZenCaster. ZenCaster is dead simple. Well, sorry. Their recording experience has gotten worse and worse. In particular, Rick and I, if you've noticed our episodes have been like 45 minutes instead of.
a normal 55 to an hour. It's because we spend the first 10 minutes every single time trying to get the right mic in Zencaster, because something is broken about it. So we switched to Riverside just for that. The production though, I just think it, like whatever AI crap it's doing to our voices, I think it like changed at least how I sound. Like my voice got a lot deeper, which is probably good. I bet a lot of podcasters are like,
yeah give me that Barry White voice, you know? But like that's not my voice. That's not what I sound like. So anyway, I'm curious if anyone else thinks this sounds worse than the older episodes.
Rick (18:19.448)
I'm gonna have to listen to last episode now. wanna hear the Barry White Tyler.
Tyler King (18:21.533)
Yeah, it's minor. Yeah, I don't want to make it seem like it's a big deal. The other thing is like, so can you hear like a fan blowing right now in the background? You can? Yeah, so I'm in my office. We record this on Thursdays, which is an in-person day. I'm always in my office and the fan is always blowing in our, like not like a fan, but like the HVAC system's always running. ZenCaster just filtered this out automatically. Riverside seemingly struggles with that a little more. So.
Rick (18:31.17)
Yes.
Rick (18:49.358)
Yeah, it definitely does. Now that I noticed that I can't stop hearing it. Well, we'll have to check it out again and then maybe we'll maybe the mic issues are worth it.
Tyler King (18:52.019)
Yeah, sorry, I shouldn't have said anything.
Tyler King (19:00.817)
Yeah, maybe. So, but Riverside, everyone loves Riverside. This is like the go-to for most people.
Rick (19:05.838)
I have another banter thing. I'm just curious. Have you filled out a bracket?
Tyler King (19:09.519)
No, it's been years since I've done that.
Rick (19:11.84)
Why? Because you don't have any friends who fill out brackets or because you don't want to.
Tyler King (19:16.881)
I don't have any friends and I don't watch any of the March Madness games. I used to do it when I was younger and even then, so I was born, my dad was a grad student at Arizona when I was, so I was born in their hospital. So I've always had a soft spot for Arizona. Otherwise, I'm just going off vibes entirely. I'm like, Maryland, they've got a turtle, I think. I'm into turtles. I have a pet turtle, so go Maryland. Like based on absolutely nothing.
Rick (19:43.342)
Well, just so you know, Duke and Arizona play tonight in the Sweet 16. So go Duke. No, but next year I'm going to remember to invite you to my pool that I run. So that you get back into it. Of course. This year, this year, this year. No, you don't have to pay anything. This year I've positioned it as a special prize that will be revealed later. I am sponsoring the prize. Yeah.
Tyler King (19:46.004)
really? Go Arizona!
Tyler King (19:55.259)
Is there money involved? Okay, well, so you're just trying to take my money, okay.
Tyler King (20:08.559)
so you're sponsoring the prize. People don't buy in. interesting. Yeah, I guess I used to like doing it, but I completely stopped watching sports when the St. Louis Rams moved to LA. Because to me, football is, American football is far and away the most interesting spectator sport on TV. Not the best live experience, but it's the best TV sport by a mile and nothing else is close.
Rick (20:33.806)
man.
Tyler King (20:36.517)
And when I decided like, fuck the NFL, I don't want to watch this anymore. I just can't get worked up about any other sport.
Rick (20:42.414)
you have the ability more so than anyone else I know to just go cold turkey on something but out of spite like for you like you you will like today if Microsoft pissed you off you will I guess you're on Apple already but like if you had a if if you had a PC you would turn you would you go buy an iMac or whatever they're called now and switch that today and never touch Microsoft products again if they pissed if they wronged you
Tyler King (20:51.655)
absolutely.
Tyler King (20:57.979)
I'm thinking about going back though.
Tyler King (21:08.525)
I'm completely driven by spite for sure. And you remember how, how into football I was like I watched. Yeah. I, and I built our own fantasy football website. I watched the Thursday game, three Sunday games and the Monday game every week. I was obsessed with football and then yeah, completely stopped. Cause the NFL sucks.
Rick (21:10.818)
Yeah.
You had at CBBlitz.com.
Rick (21:29.202)
Okay. What else is going on?
Tyler King (21:38.359)
I'm sorry that I always have the exact same topic, but, I'll talk about form stuff again. we're toying with maybe building our first AI feature, which is yes. So you and a bunch of other people, customers, people internally at less annoying have said like a, an obvious thing we should have with forms is templates. Like you, you go, you create a new form and we can say, here's a lead intake form or this or that. I've had two arguments against that in the past. One.
Rick (21:48.949)
Ooh.
Tyler King (22:08.427)
The lesser argument is I don't actually think they really save you much time because the template's gonna be wrong. It takes zero time to create a form. You have to know how to create and customize it anyway because what it comes up with will be wrong. I don't know, when you make a word, when you open up Microsoft Word and it's like, here are the templates you can use, I assume everyone on Earth just clicks blank document, right?
Rick (22:32.844)
I don't. Every day. No, in Google Docs.
Tyler King (22:33.659)
You don't use templates in Word? Which, in Google, I didn't even know they had them. Okay, okay, well, I didn't know, I've asked people about this and everyone's been like, I didn't know, I've never clicked on one of those templates, okay.
Rick (22:39.63)
Yeah, all the time.
Rick (22:48.012)
Yeah, I'm dying because I need to create one for like upheld because I have to manually update every doc to have our branding. And it's like.
Tyler King (22:54.84)
Sorry, I don't mean like that. I mean like, do you want to make a resume or do you want to make a shopping list? That type of template.
Rick (23:00.716)
I used to use those, now I use their built-in features. They have all sorts of snippets that you can build into the doc using like, you just type in Shift, Et, Shift 2 to get Et and it gives you all sorts of options. It's much more like Notion now.
Tyler King (23:06.397)
Mmm.
Tyler King (23:13.607)
Hmm, okay, I didn't even know that. Well, okay. Yeah, I have seen the notionification of Google Docs. Anyway, that was the lesser reason. The bigger reason is every customer, well, I'm about to say I'm caving on it. I'm not trying to like dig my heels in here, not like football. The bigger reason is every customer has a different set of fields in their account.
And so like a template would be like, okay, like, okay, everyone has name and email address probably, but after that, it really depends on the account. And so any template would, the form would work, but the data needs to go to the right field in the CRM in order for this to be useful. And that's like, that's not a trivial technical problem. But I think it would be a somewhat trivial problem for AI to handle. Just the mapping. So just saying.
Here are these 10 fields. Here are all the, here's the 10 fields on the forum. Here are all the fields on the user's account. Can you just tell us which fields should map to which?
Rick (24:14.498)
I mean, every conversation that we've had over the years about product goes back to the less annoying CRM user is less technical than the average Salesforce user. When it comes to setting up a pipeline, you're trying to simplify that for them. When it comes to connecting other tools, you're trying to simplify that for them. When it comes to AI, you're trying to give them, make that more accessible to them. Like to me, this makes total sense.
And all it has to do is provide value, like this much value, and then make AI easier for them to use than it would be elsewhere. And it's a win. So I don't really care what you're actually doing. You should do this. But like, what is the actual, like, are you saying like, help them build like a starting place for a new form?
Tyler King (25:01.649)
Yeah, so I think we're thinking about three phases of, like maybe one, this is the first phase and there's three steps in the first phase. The first one is very simple. You say, I want to create a new form. We pop up a thing that's like, do you want to start with a blank one or do you want to use one of our templates? And if you click a template, then it goes to, so we've already made the template, the templates hard coded in, but then we send that to the AI just to map the fields correctly. So that's step one should be pretty simple.
Rick (25:27.654)
Is the fact that you're using AI exposed to the end user? Okay. I think that's an opportunity. Just so you know, I feel like them using AI could excite them and actually provide value and also help them understand the use cases. That's not your goal with this particular project, but I just wanna go back to what I was saying earlier, which is like, you can help people bridge the gap to AI use cases, I think that's huge.
Tyler King (25:32.339)
Probably not. Well...
Tyler King (25:46.226)
Yeah.
Tyler King (25:55.077)
Yeah, I think it goes both ways. think we definitely have started having some people reaching out that have been like, so our customer base doesn't use AI, by and large. A few people have reached out and said, people have told me to use AI. Less Knowing CRM is the kind of modern tech company I trust. So I want to start with you. How do I do it? And right now our answer is, we don't have anything for you.
This isn't really what they mean. They mean more like help me write my emails or whatever, but well, I don't even think they know what they mean. But then there's a different set of people that are like, hate AI. Like AI being shoved into every other product, I immediately roll my eyes. If a Google product with Notion, even Figma is starting to do it in ways that I don't find very compelling. Some of them are compelling. think Loom is doing it pretty well, for example. I think any of the content creation apps, Riverside does it well.
But I think there are a lot of people who are like, you're just shoving AI in here just to say you've got it. And they have a negative reaction to it.
Rick (26:55.63)
So don't if you can see under my rants and shout outs, but I put a topic on here that is very relevant to this conversation where it's going. Like I actually disagree with everyone on this. think there were at a pivotal, like I don't know what it's called at the transformative moment where like pivotal, yeah, like I think we're here and like there are so many applications that are.
Tyler King (27:01.991)
Hahaha
Tyler King (27:14.035)
Crossing the chasm kind of thing.
Rick (27:22.863)
massive leverage for go-to-market teams. Okay.
Tyler King (27:24.837)
saying there aren't. I'm not saying there aren't. I'm saying we're being overwhelmed by bad use cases and it poisons all of the good ones.
Rick (27:29.804)
Agreed.
Yep, yeah, I mean, if you have a bad AI use case and it makes you look bad, it's kind of like Wikipedia back in the day. If you cited Wikipedia before it was like actual source of truth, like you probably looked bad.
Tyler King (27:45.681)
Yeah, yeah. And like, so a part of me thinks good AI doesn't brag about being AI. It's just, it's a product, it works and hopefully it kind of feels like magic versus like, like it would never occur to a customer that making a form template would be difficult because they wouldn't think, you have to figure out what custom fields I have in map to it. So I almost feel like it's trying to explain to them there's a problem they didn't know about so that we could tell them we fixed it rather than just not having the problem there at all.
I get what you're saying though. Like it's maybe a marketing opportunity.
Rick (28:16.213)
Yeah.
Yeah, yes. But yeah, not relevant to getting more use cases of forms. It's more of a broader topic. So what is the, like, where are you on your pace?
Tyler King (28:25.415)
Yeah, I think that-
Tyler King (28:30.971)
Still going well. We're on pace for July 1st. We're hoping to get 1200 submissions per week at that point and every week we have a little spreadsheet. It's like how many do we need to add per week to hit there and we've been exceeding that number. So we are ahead of pace for that right now. Yeah, it's going well.
Rick (28:47.032)
Woohoo! One thing you mentioned last time where you were gonna basically look at all the people who have looked at a, filled out a form, like based on their email address or something, and then compare that with signups. Is there any correlation, or any like overlap there? Okay.
Tyler King (29:01.511)
We haven't done that yet. And when we do, it will not be backward looking. We could do that, but again, there's sort of this like sketchy, can we scan our customers data? like, I'll admit this is sort of performative, but we want to hash all the emails just so that we're not ever looking at the real email address. Anyway, so we're not going to be able to do a backward looking. We have so little volume going backwards that I would be pretty surprised if there are any hits. Cause I know how many people are clicking the powered by.
And it, I mentioned last time it doubled recently cause we redesigned things, but it's like three people a day roughly are clicking this link. So I would guess based on our other marketing channels and stuff, I would guess something like a 1 % convert 1 to 2 % conversion rate of people clicking the link to signing up. Um, so we'd need like a hundred clicks and I don't think all time we've had a hundred clicks.
Rick (29:56.674)
That's enough. Like, that's great.
Tyler King (29:59.643)
Yeah, yeah, no, I'm excited about where it's going, but I would guess we don't have results yet that we could prove even if we had this data.
Rick (30:07.886)
What if you just like spun up like a data room if you call it, you were the only one who had access to it and you did a quick analysis and then deleted all the data. Like why not just do that real quick?
Tyler King (30:21.253)
Yeah, so partially because we have a developer building this right now and it'll be ready in a week. I'm just not, well, and it doesn't, this goes back to a constant question about data stuff. It won't change any of our behavior. Like I already have the appetite to keep working on this. So I wouldn't do anything with that information.
Rick (30:26.688)
Okay. It's not urgent.
Rick (30:40.034)
It might make you feel good.
Tyler King (30:41.533)
That's true. getting, I've told you before when line go up, check the graphs all the time. So I've got like four different things bookmarked right now and I'm checking them like multiple times a day. I can't help myself. But yeah, so we're also, we are gonna build a more AI type feature, more along the lines you're talking. Once we build that first step, which will be invisible to the customer, then we're gonna build a, hey, tell us about your business.
Rick (30:52.129)
Yeah
Tyler King (31:10.279)
What are you, what are you, cause you used this language last time that I really liked, like our CRM coaches should be asking customers like, you know, what initiatives are you working on? What are some challenges you're facing in your business? I want them to just, I want to see how this goes. Just type that in and we'll come up with a bunch of ideas for how you could use forms.
Rick (31:26.808)
That's a great use case. my God, that's amazing.
Tyler King (31:28.893)
Yeah, because this is the less important point of form templates is speeding up the process of making the form. Because again, it doesn't, takes like 30 seconds to make a form. The more important thing we can do here, Eunice, our marketers keeps talking to all our form people. She's manually onboarding people. When they hear about it, they're like, this sounds awesome. I'm really interested. I just can't think of what I would even use this for.
Rick (31:52.094)
Can we pivot for a second? Can we build an AI prompt like chatbot? Not chatbot, like, can we build AI into leg up health? I feel like there's a great use case here in terms of just getting people to use, it's the same problem, right? We're serving the same customer, less technical. They probably don't have chat GBT pulled up all day. It's probably an HR person employee. if we apply that to benefits that we could see their prompts, it would be.
Great feedback loop for product. Is that hard?
Tyler King (32:23.347)
If all you want to do is see their prompt you don't even need AI you just have a text box and they hit save and I email that to you
Rick (32:29.356)
Yeah, like we have, yeah, but we have to give them like real time value in order to get this prompts like.
Tyler King (32:35.271)
What's the problem? don't get what the question we're asking them is.
Rick (32:37.262)
What's your biggest benefit challenge right now? what I need to communicate, leg up benefits to a new hire, how do you recommend I do that? Those types of things. Could we have an AI?
Tyler King (32:53.223)
I mean, we could, my attitude here is.
Rick (32:56.002)
You would have a person put a person behind that in the short term.
Tyler King (32:59.249)
Well, especially because nobody's self-service signing up for LEGO Health. So if we don't know the answer to what are your biggest challenges, like JD should be asking that during the sales process, I would think.
Rick (33:10.318)
I guess what I'm thinking is that this will help them sell leg up health by saying we have AI and having that tool there. But it's okay, we can come back to that. I was just curious, I guess my question is how hard is it to build a V1 of a leg up health sort of skinned chat GPT within the leg up health portal?
Tyler King (33:16.252)
Yeah.
Tyler King (33:35.781)
If it's not, if it doesn't have any special training or anything like that, it's very, very easy. my, my basic summary for, you know, technically this is an integration. You're calling someone else's API. Hard integrations are one where you're sinking data back and forth, right? Where you're like, we have contacts on that end. have contacts in this end. And when one thing changes on one, it has, it has to push bi-directionally cause you can get duplicates and you can get conflicts. Easy integrations are we're just pushing stuff one way. This is a, simplest version of a one-way push. It's like, give them the text.
Then there's another push the other way. Give us the response. Super, super easy to build. I think where it gets hard is like, if you want to give them good advice, which I think with health insurance, you really, really do. Like if this is a consumer asking questions about their health insurance policy or something like that, we would probably want some kind of data source that is like, you could imagine training it on all of JD's emails and chats in front that I haven't gotten into that. know chat GPT has tools for it, but I think it gets harder to do that type of
Rick (34:35.05)
It's probably going to be a tool that we're already operating in that provides this to us probably front like that we like, like that's probably, it's probably going to be that or another tool we buy that already is, has their access to our data. It makes it simple for us because we are a small business ourselves. So I just need to be patient.
Tyler King (34:49.298)
Yes. Yeah, we've been trying it with front LS annoying. Man, again, these companies are all, feel like they're just letting the moment pass them. Like they're all trying AI, but there's all these things that should be like, I feel like everyone's just like the AI's magic, let the AI do its thing. But let me give you a specific example. And we're actually using a tool called Resolve 247, I think it is.
Yeah, 24 seven, guess. Okay. I never pieced together to the two four seven meant 24 seven. I believe their founder is a listener. Hello, if you're listening. And it's, it's been like kind of a good, not great. would say like it's better than what's front, what front is offering, but like, here's an example of the type of thing that these AI tools I would love for them to do that I don't think resolve can do, but front could is like, okay, it suggests it basically writes a draft.
Anytime a customer emails in, it writes a draft of a response and we just review it. And if it's good, we hit send. It's almost never like good enough that we send the actual draft, but it gives us a starting point. What it should be doing is detecting how we changed the draft and interpreting that. And again, I don't think front APIs allow resolve to do this, but what front could do is write the draft and only train future emails on the changes we make to their emails. Instead, what I know is gonna happen is it's gonna train on the
template that it wrote, it's gonna start training on its own data and it's gonna be the snake eating its own tail. I just know that's the direction this is headed. Like, Front's doing all this AI stuff, but it's all just like off, in my opinion.
Rick (36:25.718)
I mean, that's you're describing most AI, like broad AI applications, which is like based on fake bad data. Like at the end of the day, like if you don't like how many wiki internal wikis have you ever looked at that are up to date?
Tyler King (36:43.015)
Yeah, right.
Rick (36:43.756)
Like very rarely is it up to date in the minute, like every day it decays, right? And so unless you have, if you want to use AI for like an internal Wiki use case, just as a basic example, like a company internal documentation, someone's got to be very responsible and accountable to pruning and maintaining the content. Otherwise, like the AI can like totally mislead, not at the AI's fault, at the documentation's fault.
Tyler King (37:11.207)
Yeah, well, it's even worse than that. With your use case, I agree. With the email use case, we run into this all the time where the AI will recommend a thing that was true six months ago, but it's not true now. And we have updated the docs. We have sent more recent emails, but there's this whole backlog. how is the AI supposed to know that we changed something if there's like this email that it's referencing that said a different thing, you know?
Rick (37:35.854)
But I feel like that, especially for email, like, how do you, someone's got to, there's got to be like a date, like data set that it's, it's training off of, and you've got to be able to update the data set and retrain. Like there's got to be a recurring cycle for that. Someone's got to go archive that email and remove it from the training and mark it as bad.
Tyler King (37:53.265)
Yeah, but you want all of the old, like most of the old emails are still correct. Yeah, it's so hard. And then, and so like, is why human intelligence is great. Like we teach our team and they learn and stay on top of it. I'm pretty worried that the more we rely on AI, the harder it's going to be to train a new employee. And they're not even going to be able to do the stuff that our current serum coaches can do.
Rick (37:57.985)
Yeah.
Rick (38:14.528)
God, you're scared.
Tyler King (38:15.953)
So yeah, huge opportunity. And I'm not trying to bury my head in the sand. Like I want to be on top of this. I agree with you that there will be really big use cases. I don't agree with the people who are like, AI is advancing at leaps and bounds. Like the Chetchi BT, in my opinion, can still do roughly what it could do a year ago. Like it's gotten better in certain ways, but the use cases for it, we're still figuring out. And I think there's a lot more we can do in terms of building those tools into what.
like different SaaS products, but it's still just missing the mark so often, I think.
Rick (38:49.154)
Yep, I agree.
Tyler King (38:51.031)
anyway, I'd love to, I'm happy to explore it as a kind of product thing for, like a health, if for another, like, I'm not sure I'm excited about the idea as a stakeholder in the business, but as a technologist, I would love an excuse to go play around with this stuff.
Rick (39:06.646)
Yeah, exactly. We've got it. think like, I think we've got long like the reality is like we have some immediate product opportunities that don't need AI that we can deliver on. And we probably shouldn't get distracted this I think for leg up like AI should be used for generating business, not necessarily servicing businesses right now. And if we can't identify a growth use case, like it's probably you know, a backlog item for now, which is sad, but
It's true.
Tyler King (39:37.745)
Yeah, and what you'll notice about the AI use case that we're toying with for last night's serum. And again, I said, this is kind of phase one. If this works, I want to build it into our onboarding. This isn't a feature our customers use exactly. mean, it kind of is like, but a customer is not making a form all the time. This is partially for cost reasons. Like more expensive SaaS products are like might do something like this. Every time you look at a contact in your CRM, we're going to summarize.
the state of things for that contact, which means every time you look at a contact, we're making a call to the OpenAI API or whatever tool you're using and generating stuff. That adds up. Our typical good customer is using Lesson Learning Serum for eight hours a day, 20 days a month. That would put us out of business. We'd have to raise our prices dramatically to do that. But to be like, when you want to set up your account, we'll run one call to OpenAI, that's gonna cost like a penny.
I'm the growth version of this. I'm excited about is just making onboarding and set up way, way smoother, both faster and easier, but also just like, you wouldn't believe the number of customers we talked to. They've been using us for five years. We get on the phone with them. They've never set up a call with us. We've never talked to them before we get into their account and we're like, my God, you have, you have a disaster here. This was set up completely wrong from the beginning. If AI could avoid that.
I think that improves our trial to paid conversion. think it decreases churn. I think it could have a big impact.
Rick (41:08.75)
That's huge, yeah, I agree.
Tyler King (41:11.776)
yeah. What about you? Back to you.
Rick (41:17.592)
I mean, the main only update I have today is that I have this thing that I need to do, which is I have a lot of information in my head and I need to make sure that you, me and JD are on the same page related to our long-term product vision. kind of, the history is like one summer you came out when you first started working with Legapalith and we built a product, and we were very focused on the employer use case, but we basically scrapped all that work and then rebuilt the consumer application and have like,
Kind of been stagnant in terms of the employer experience since then. the, there's a huge opportunity to support like JD going to market with, employer value that he can demo, and like converting this pipeline that he's building. And I just need to figure, I need to, like, I want to like do, do some exercises with the end in mind and go, Hey, like in 10 years, this is what I think we could have. Here's what I think this looks like by year for the next 10 years. And then it.
Tyler King (42:14.845)
Mm-hmm.
Rick (42:16.64)
it becomes like very obvious, like what we should build first. And then I would love to get your feedback and JD's feedback on that. But I am having trouble finding time to do this, which is frustrating.
Tyler King (42:28.307)
Can I make you more frustrated? I think there is a window of time coming up where it would be really helpful for me to know what I should work on next because two weeks. Let me caveat this. So my child's due date is in about two weeks. I'm taking a month off. It's very possible I'm sleep deprived and get no work done during this time. But you talk to parents, different parents have different experiences. Some are like,
Rick (42:30.029)
Yeah.
Rick (42:36.846)
Okay, how soon? Two weeks, okay. All right.
Tyler King (42:56.135)
The husband can't really do anything anyway. I'm sure I'll be spending time bonding with the baby and stuff, but like there's a chance I'll have quite a bit of time to work on something and I'll spend it on like up health if we have good projects.
Rick (43:08.628)
Eat. This is what I needed. I needed a kick in the butt and I needed a deadline and now I'll get it done and it'll be like, it'll, it'll not be perfect, but it'll at least like be contextual. all the context we need to have like the next level of conversation, which I feel like we're missing right now. and so thank you for that. That's what I needed.
Tyler King (43:25.137)
Yeah. Can I also give some thoughts on, I mean, I'm going to follow whatever direction you set because you know this industry and I don't. would, you said a second ago, like make the 10 year vision and then kind of work backwards to what we build now. The 10 year vision is going to be wrong. No, it doesn't matter how smart you are. like, and maybe you would do this anyway, but like I'm interested in what are the things we are certain.
we need as opposed to what's the first step towards the 10 year vision? Even if it's like year four, but we know we're gonna need it. Yeah. Yeah, like what's something, yeah, if I do have time and I spend a month on it and I give it to JD and just imagine I never build anything else ever again, what's the thing that like a couple of weeks of work gets value we know we can sell today as opposed to like, it's not really that useful.
Rick (43:58.1)
skateboard versus the wheel.
Tyler King (44:20.805)
until we do years two, three, four, five.
Rick (44:23.33)
That makes sense. Cool.
Tyler King (44:26.035)
But yeah, that'll be fun to have a little product vision going on.
Rick (44:31.048)
Yeah, yeah, I'm excited. And it's like, I think it's, it's easier to justify, like, prioritizing this when you when there's pipeline that, like gets converted, like in real time as a result of the work, like, I think we now have because of JD's pipeline building, and his focus, we now have this cycle of market feedback that I think it's time to do this versus like, if we tried to do it last year, it would have just been, we released a feature, but no one's using it.
Tyler King (44:57.361)
Yeah, for sure. Yeah, I definitely want in this podcast to stay on top of like to keep getting updates on was this a fluke or if he doesn't even have to have what he's going to close like five employers this month. It sounds like I know, know a couple of them are really small, but
Rick (45:10.978)
Yeah, yeah. Yeah, if he has a pipeline of 20 or so employers that he gets to, he's at 13 right now. The steady state, they're leaving either from lost or they're being won and then they're being replaced by others. We have everything we need to like really grow the business this year and get lots of feedback on the product offering and improve the demonstration of value. that's what I'm, if I'm being,
totally honest, there's like two factors here. Like I want to make sure that we empower JD to demonstrate the value of our employer offering. And then second, I want the employer offering to deliver the product to deliver on what we're demonstrating. And so like that the pipeline should drive like the immediate pipeline really should drive what the prioritization.
Tyler King (45:59.389)
Yeah. Okay, great. We got four minutes. Can I give one more update thing? Yeah, basically, so at Lesson.0 CRM, I've said many times in the past, like we shifted from each developer works on their own project, meaning if there's seven developers, we need to have seven projects going on. Don't love that because priority number seven is not nearly as important as priority number one. So we shifted to like trying to put everyone on the top priority or one or two priorities.
Rick (46:04.642)
Yes, yes, yes.
Tyler King (46:29.873)
That worked well last year, but I'm realizing it's because the projects we working on were kind of uniquely good at having a lot of developers on them at once. The next two we're working on, we've started on mobile and Kanban, they're just not like five person projects, I don't think. So anyway, we're kind of going a little broader. We're kind of backstepping a little bit and saying, we're not gonna have seven projects going on at once, but I don't think one or two is realistic here.
All that to say, I've started designing our next big CarPlay feature, which is automations. So the idea of, you move a contact from one status to another and some things automatically happen. We don't have the ability to send emails yet, which is the obvious thing people will want, but we can create a task assigned to a group, whatever, and then we'll add emails later once we have that ability.
Rick (47:21.742)
Trigger, condition, action.
Tyler King (47:26.471)
Yes, and I think for our customers being less tech savvy, the trigger will often be manual. Like one of the features will be, you can just go to a contact and run an automation. like one of, click a button, a super common use case we hear is, I wanna, know, for every lead, I need to create like the same three tasks, like a next day follow-up, next week and next month or whatever it is. Now you'll be able to make that an automation and you can just go to a contact and say, add these three tasks all at once.
Rick (47:35.48)
Click a button.
Rick (47:54.2)
That's awesome. mean, this is something that I'm a pretty big Salesforce fan in terms of a rev ops work and CRM. they make creating buttons and driving workflows off of that extremely complex and hard to do. There are so many cool use cases for that, that if it was easier in Salesforce to do that, we would have more buttons.
Tyler King (48:12.573)
Hm, we don't have time right now, but I'd love to hear what you, obviously you're doing more fancy stuff, but I'd love to hear that just for, well, maybe do we have time?
Rick (48:18.402)
Yeah, it's all the same. Yeah, it's all it's all the same stuff. I mean, it's like in sales, oftentimes you're done with an account and you to drop the account, click a button. If you in
Tyler King (48:31.239)
So pause real quick though. When you click the button, what happens? It updates the status and the...
Rick (48:34.28)
It changes the owner, updates the status and moves it into a different user or queue. Say for example, out of your pipeline, basically. That's a very common one. Another one might be create a series of tasks. Another one could be mark as something that someone else needs to do. So for example, a handoff from sales to customer success.
I'm realizing a lot of these are ownership changes that, that act as something that needs to be done. yeah, like I've tried to think of other ones, round robinning, like around Robin button. that's a very common one.
Tyler King (49:11.953)
Okay.
Yeah, that's one we've been, so say like you've got a team of users, assign it to some random person on that team basically.
Rick (49:22.188)
Yeah, the, there's kind of two pieces. There's the button that triggers and then you have to have functionality that allows a randomness or round robin assignment, which is another feature. But like you can build that in Salesforce with workflows. like that's a really good one.
Tyler King (49:39.643)
Yeah, we've been toying with that one. That's like on the border of too advanced for our users. 70 % of our customers are single users, so assigning doesn't matter to them. But I bet we end up building that. I think it would be really easy and we could, the way our UI already works, it would not be complicated to set that up at all.
Rick (49:44.12)
Mm-hmm.
Rick (49:51.576)
Mm-hmm.
Rick (49:57.482)
Another example is like oftentimes in sales environments with multiple users, you'll have accounts that are pulled by a user who is not like it could be a manager or a generally a generic user or Q. And there's a requesting the account process. So two types of things, let's say an eight, an account executive owns an opportunity or an account that another AE wants to work. And there's what's called squatting on it. They're actually not actually doing any work, having a process for requesting the account.
be transferring, like that's a button. request related to records is another thing that needs to go into a queue for review. That's another use case. I've got a lot of these, if you get me going on them.
Tyler King (50:27.446)
interesting.
Tyler King (50:35.602)
Hmm.
Yeah, yeah. I might pick your brain later about that. One final note, I've held off on, so automations are actually going to be pretty easy to build. We already have the infrastructure because forms have automations. Like when a form gets submitted, you can already take all these actions. I've held off because I thought it's complicated. We're going to make it way simpler than Salesforce, but like our users are so low tech. But we had a realization that I think is kind of interesting, which is
Again, kind of like the form setup I was just talking about, it's kind of a one-time thing. Like you set up your automations and you're done. We have amazing customer service. We can just like, I think this could be make our product really sticky and kind of make our customers feel like, like software as a service, I feel like we forget the service part a lot. If we just say, hey, you can go set up automations if you want, but the main way, the main flow is come talk to us. Tell us what you want. You don't even have to talk in terms of automation. Tell us about your business.
What happens step after step, hour long call, we'll set up all your automations for you. You never have to learn how they work. They'll just run automatically for you. Yeah.
Rick (51:42.862)
100%. It's a huge opportunity.
Tyler King (51:46.723)
you gotta go.
Rick (51:47.118)
You gotta go.
all right. Yeah, you do have to go, right?
Tyler King (51:52.541)
I actually don't have anything right after this if you wanna extend a little.
Rick (51:55.406)
I'm interested in how you think about parental leave, but that might be a longer conversation. I guess we can talk about that next time.
Tyler King (52:00.775)
We can talk about, I mean, there's a good chance the next time we skip recording. Yeah, we can talk about that if you want.
Rick (52:04.726)
Okay. Are you, are you, are you setting it up so that no one can call you? Or are you setting it up so that you're available like once a week or that sort of thing?
Tyler King (52:16.909)
I'm not expecting, so I'm setting it up so no one should need to call me, but I also know I'm going to be checking email and Slack and stuff. So if you know, like I'll check the public Slack channels, like what's going on in dev chat, what's going on in company chat. I think everyone, I haven't said this explicitly, so maybe I should, but I actually feel pretty good. It's, taken 15 years to get here.
I'm bad at delegating, like over time we've gotten there. I think almost every question goes to either Michael, the head of the customer service team or Robert, head of the dev team or Eunice, the marketing part. Like questions rarely come to me first anyway. So I think people would now go to one of them and then they can escalate it to me if they want to is probably how it would work. But I'm no, I'm not, my intention is not to like fully 100 % unplug just cause I know I could, but I'm not going to anyway. So why bother?
Rick (53:11.032)
I'm very interested in how you react to this. Because my version was like two weeks and I was like, I need to do something else. And so I was like, super bored. Yeah.
Tyler King (53:22.195)
really? You got like kind of bored or whatever. Yeah. That's why I would love, I'd love the leg up health work. Like I could obviously do less annoying CRM work, but this is my once every three years sabbatical. Like the way our policy works, everyone gets a sabbatical every three years. If you have a kid, you can do it at more than every three years, but it just like extends the timeline. Like having a kid counts as a sabbatical. So yeah, this is my time and like working on a side project makes more sense than doing my normal job.
Rick (53:29.069)
Yeah.
Rick (53:50.378)
I am motivated to get you that document. Okay, I'm going. No, no, no, no, but it's good. need to do this. Rather you work on it in the next two weeks or in the next year. Like it doesn't matter. So, well, if you'd like to review past show notes and topics, visit StarUpToLast.com. We will see you next time if Tyler is not a father.
Tyler King (53:52.147)
Okay, but no promises. I need my sleep, so I might be a zombie. Yeah.
Tyler King (54:03.153)
Yeah.
Tyler King (54:12.039)
Yep, see ya.