Tyler (00:01)
Rick's outbound prospecting is starting to generate leads, so now it's time to get the funnel working for real. Let's go.

Rick (00:25)
What's up this week, Tyler? I beat you.

Tyler (00:25)
What's Rick?

you beat me. got back from my trip to to France, so from France. So not a lot's happened with me since we last talked 'cause I've been on vacation pretty much the whole time.

What's going on with you? I was in Paris. We were supposed to do half the trip in Paris, half the trip in like French countryside. We rented out like a little mini castle looking thing for the the whole family. but it there was a big heat wave, and the castle is not air conditioned. Basically, nothing in France is air conditioned, although thankfully the hotel in Paris was. So at the very last minute.

Rick (00:40)
Were you in Paris?

Tyler (01:06)
We just cancel well, we didn't can't we still had to pay for the whole other part of the trip that we didn't even go on, but we just booked our hotel in Paris for another few days and stayed in Paris the whole time.

Rick (01:18)
That's awesome. So much to do there.

Tyler (01:20)
Well, yeah.

yeah. You definitely don't run out of stuff to do. It's a bummer that you know, like having to cancel half the trip and refigure it out immediately was a bit of a bummer. But no, it was amazing. I I was not expecting to like Paris. I didn't think everything you hear about it, the reputation, all that the things that people say they love about it aren't things that matter to me, but but I thought it was great.

Rick (01:42)
Yeah.

That's awesome. Well, did you have a highlight?

Tyler (01:48)
yeah, I can I'll maybe talk about a few, but the the overall highlight is it's good to travel when you have money. I'm kind of entering the point of my life where I'm comfortable like spending it's not just like fly coach and then stay in a hostel and then, you know, do like go to a museum by yourself and try and figure out what's going on. It's like this is my first time ever flying international business class. That's awesome.

Staying in a really nice hotel. Everything we did basically had a private tour guide. and like a lot of private transportation. You know, someone just picks you up from the hotel and drives you there. So main takeaway, it's good to have money. I highly recommend it. money's good. But I I feel like in my normal day to day life, money, additional money does nothing for me. Like you I could buy a bigger house, I could buy a more expensive car. That would not bring me happiness at all.

Rick (02:31)
Money money's good. Money helps.

Tyler (02:45)
Travel is one thing where I feel like the money is buying happiness very directly. So an example of this, we went to Notre Dame. Of course, everyone does that. The tour guide was a so you know it like there was a big fire there in 2019, and basically they had to rebuild the whole thing. The tour guide was one of the master sculptors that they hired to rebuild it. So the tour wasn't just like, hey, this is a church. Here's the history of the stained glass window. He was like,

Hey, here's how we rebuilt this part of it, and here's a picture of me doing it. And let me tell you about all the other people that you know were helping. And then we walked around the whole outside, and he just gave us all these cool details that you would never get, certainly not by doing it by yourself, but even with like a normal tour guide. so anyway, I that was probably the most unique, memorable one, but like several different things we did kind of had that feel of like the person walking us through it was an actual expert on that thing, not just some random tour guide.

Rick (03:39)
Yeah, you're talking about like a premium experience tr tour kind of thing. Yeah.

Tyler (03:42)
Yeah. Yes. Ver

very I obviously I'm I'm joking with the highly recommend in the sense like of course everyone would love to be able to do this, but this is one of the main times in my life I've felt the benefits of the the financial success of less annoying CRM.

Rick (03:56)
having some money.

That's awesome. That's that's great. did do do you did did did anyone when France lost riot?

Tyler (04:08)
I left before they lost. so we were there for two of their wins and you know, it's it's the middle of the night there because the World Cup's happening in North America. So we're sleeping and then at three AM you just hear like Brah and everyone's cheering and

Rick (04:10)
Okay, that's good.

Yeah.

They're passionate people. Like they get they take to the streets.

Tyler (04:28)
Yeah. Yeah, I'm I'm kinda glad I wasn't there when they lost 'cause that would not be f I mean, they I care about sports and that like or I I used to when the Rams were in St. Louis. I you know, I wanted them to win, but I wasn't like it wasn't ruining my life if they lost. Several of the like tour guides and other people we interacted with there, we'd talk to them and they'd be like we you know, just ca p politely like, how are you doing? How's your day going? And they're just like, man, I c I I can't think about anything. Tonight, the game's tonight

I'm just so nervous. Like it it takes over their whole existence in a way that I I don't experience. So yeah, I bet they're pretty bummed.

Rick (05:05)
that was a bummer. Well I'm excited to to see Argentina and Spain in the World Cup. I'm I'm rooting for Argentina. I'm a messy fan. You don't care at all.

Tyler (05:13)
you can't

but you can't root for the same team that won last time. I mean you are, but I'm a I'm you're one of them. I'm always root for the underdog not that Spain's much of an underdog, but anyway. Yeah, yeah. But still it's it's t two two overdogs competing with each other.

Rick (05:18)
I I am definitely doing that. I rooted for Michael Jordan too. Yeah.

No. I think they're fa I think Argentina is the underdog this year.

Did you work at

all while you were on vacation or did you take complete time off?

Tyler (05:39)
Basically complete time off. I mean, I had my computer I j I like check email and Slack almost as a hobby. Like I don't I don't have Facebook, I don't have Instagram. checking Slack is actually kind of a form of mindless scrolling for me. But no, I didn't really work aside from one day the site was having problems and you know, Bracken and I were both in France and so everyone in America was asleep at the time. So we we handled one server issue for

thirty minutes, but other than that, we did not work.

Rick (06:12)
For you. That's that's awesome. What w did you come back to any fires or is it all like smooth sailing?

Tyler (06:13)
Yeah, feels good to unplug.

I'll pretty good. I mean things are really hectic for me personally right now because HIPAA, like we have to have HIPAA launched basically a week from today. And it is not ready yet. I mean it will be, but I got a lot to do, but no, not nothing like when we were gone big problems happened that needed to wait for us. Nothing like that.

Rick (06:39)
That's awesome. Did you use AI at all on the trip, like to help you with experience the culture, or was it mostly what did you what was those some of the use cases?

Tyler (06:44)
yeah.

I mean some of it's just like like for example, my nephew is getting into Magic the Gathering. Did you ever play that? you know what it is, like nerdy card game. Yeah, I was very into it.

Rick (06:54)
Mm. No. I do, yeah. I mean, isn't isn't

like that Netflix show based on Magic the Gathering? the the the horror the horror one that just concluded. Stranger Things. Yeah, I thought it was. They like they they get in a room and they have like make believe storytelling stuff that's happening. Yeah, is that different?

Tyler (07:01)
Which one? I don't know

I don't know. I don't even know what that is. is it? I don't I don't know.

Dungeons and Dragons, maybe? Yeah.

Magic the Othering is a card game. I mean, same probably appeals to the same type of person. anyway, I had to take

Rick (07:21)
no.

Okay. Yeah. I don't know either what

either of those are in detail, I just know of them.

Tyler (07:29)
you're such a jock.

Rick (07:32)
I was I was

nice to the guy. to I wasn't like the mean jock. I was like, I want to be a play card game, so just it's very it's hard for me to understand what's happening.

Tyler (07:36)
Yeah.

Well, I was the nerd that you were trying to be nice to. anyway, I was taking my nephew to get some cards and just like I need to buy cards that are in English. How do I find the place that will have that? That's just a type yeah, that's the specific example that comes to mind. But yeah, I probably used AI a few times a day. You know, translate something. I need to say something or not not say, I can't pronounce anything in French, but I need to write something to somebody, translate it for me. yeah, just find me a restaurant, things like that.

For sure.

Rick (08:12)
That's awesome. Yeah, I've had a couple of AI wins lately. Like one of D I tell you, I don't know if I've covered this on the pod podcast before, but we've connected Claude to like a lot of different tools at Windfall. and recently Salesforce and Gong, which are like Salesforce is our CRM, gong is our what do you call it? recording tool, like for meetings.

Tyler (08:25)
Yeah.

Rick (08:39)
And between those two tools, it unlocks some really cool stuff. But like one thing in my job that I really, really hate doing is, and y this will relate to less and CRM, is if you're if you're like me at a company, you're responsible for making sure the pipeline reporting is accurate so that you know the company can forecast what future sales are. And that's all based on your pipeline reports in a CRM, which have closed dates associated with them. And one of the like most negative signals of bad pipeline health and a bad forecast are closed dates in the past. and so I used to

Tyler (09:06)
Mm, yeah.

Rick (09:09)
Every week, have a report that fires, and then like basically mass flame everyone or chatter them and you know basically say please update your opportunities. It's like the worst part of my Monday. I basically had Claude, so in Cloud Cowork, there is this thing where you can r run tasks on your computer. but then I was like, I don't really want it to run in the computer, I want it to run in the cloud. Can't do that with cowork. So I went over to code and there's this thing called routines, which are basically cron jobs that you schedule in the cloud.

Tyler (09:36)
Uh-huh.

Rick (09:37)
And I scheduled a routine that basically I I basically gave Claude Code a Salesforce report and it was like, tell me the filters. And it basically created a a Salesforce SQL query that runs every morning at nine a.m. It goes and grabs all the deals with closest in the past, identifies the sums up the ARR amount that they represent, sums up the unit numbers, and then matches them to a Slack handle.

And then it sends a Slack message to our pipeline channel and mentions the people in in a in a in a top to bottom order of who has the most past due ops and links to the report for them to update it. Every morning at nine AM.

Tyler (10:18)
Little is this

deliberately like shaming like is shame part of the intention here?

Rick (10:23)
No, it's it's helpfulness. Like I'm not being like you're bad. I'm just like, hey, this is a helpful report for you to know that you have some opportunities to do it up and fast. The number went from a hundred it's at a public jail. Yeah, it's in a public jail. and so anyway, it fires every day and that list has is the it's gone from one hundred and twenty on Monday to six today in one week.

Tyler (10:30)
But it's in a public channel rather than DMing them. Yeah.

Wow.

I mean, does it the work that needs to be done is just change the date? Or is it like you have to actually follow up with them or

Rick (10:48)
Yeah, that's it.

Well, I it's like, hey, you should be working this opportunity, like, make sure that it's got an accurate forecast date of when it's going to close. And usually when it's in the in the past, two one of two things needs to happen. One, it needs to be closed out as a loss deal, which is a good outcome, right? For reporting purposes. And then two, or two, it needs to be like re restrategized. Like, okay, what we said was was going to happen did not happen. What is the go forward path? I'm going to adjust my expectations of this deal. Maybe the amount needs to be adjusted too.

closed date needs to be pushed out and my forecast category needs to be downgraded.

Tyler (11:27)
Yeah. Yeah, I mean that's cool. Yeah, for sure. I kind of I keep hearing things like that and it always sounds like, yeah, duh, not not that that's not transformational or anything, right? But if if you do that in enough different places, I think the dream is human labor is being spent on the highest leverage things possible. And we all experience this. You you know, it's it's eleven thirty AM and you're like, I haven't done anything yet today 'cause I'm just moving emails around and yeah.

Rick (11:28)
Anyway, that's a s I thought that was a cool AI like win.

Clearing the queues.

Tyler (11:57)
the dream is you don't have that anymore. I just like have never come up with one of those for me. Like, I I do I have the 1130, I haven't done anything thing all the time, but then I look at it, I'm like, well, this was a one off thing I've never done before. Like I couldn't have automated that. Or like, well, this one I can't, there's not a system to connect it to, or whatever. I I don't know. I'm jealous, is my point.

Rick (12:05)
Yeah, it's interesting

Yeah,

yeah, yeah. It's I think thinking of it in Q if you're clearing cues every day in a repeatable way, like that's probably the thing to point this at. if you're not, then that's hard. Like it's hard to make it's hard to make something up.

Tyler (12:27)
Yeah.

Yeah. This is also a good reason to use Salesforce as much as I hate Salesforce or these enterprise y tools is you can just there is a source of truth, you can connect to it. V versus like, I've got some stuff's in a spreadsheet, some stuff's in a notion doc. Even the stuff in a notion doc is not structured the way I assume Salesforce is for you. yeah, okay, I'm rambling.

Rick (12:58)
Yeah.

Yeah.

Tyler (13:01)
Cool. what's up with your coding journey?

Rick (13:06)
made much progress. No progress. I mean, I I've been shifting a lot of my AO work to Claude sort of on like deeper clawed co work and chat and code things, but very few like custom coding projects. My website's working great. Like I think it actually improved my SEO. I'm getting much more traffic to my website as a result of the the updated personal website. I am definite yeah.

Tyler (13:07)
No progress.

Do you think

well s d do you think you need to keep going? Like, the reason you were doing this is not that you needed to update your website. It's that you wanted an excuse to kind of jump into the AI coding stuff. Do you but I I think there's a world where you you do what you did and you say, I can just ask Claude Code anything and figure it out, got it, but I don't actually have a thing I need to do. Like, is there more learning you need to do, or did you get what you needed out of it?

Rick (13:40)
Learn.

I think there's this frontier with a crud app that I never really crossed in terms of the front end talking to the back end in a like way that I fully understand and can can do on demand. And I I do want to force myself to understand that and and kind of cross that gap. so I I do plan to do that. It's just not at the top of the list. there there are actual problems that I can use AI to solve right now that make my life better.

but that is I still something I want to do is is have a app that I under that that has people logging in, has me logging into it. and I'm planning to do that through my personal website. I haven't published any new content on my website since I launched it. And so I I kind of am gonna use the publishing process to build that out.

Tyler (14:42)
But you're if I recall correctly, you built the website basically like a static site generator, by which I mean locally it pulls the content down from Notion, turns it into like an HTML page or something, and then pushes it up to a server.

Rick (14:55)
it's it's not that sophisticated. Basically, it there are markdown files that ha host the content the the variable content, and then they're temp there are templates and then at sort of like the the the load loading of the website, like it constructs all the pages.

Tyler (15:03)
Mm-hmm.

I thought you said it does it when you deploy it, not when the the site loads.

Rick (15:16)
So when the de when the site deploys. Mm.

Tyler (15:18)
Okay. So th th the

reason I say like you don't have that world doesn't need any back end. Like you're saying, I'm shipping, it's gonna run some whatever, and then it's gonna generate static front end code and that's the whole website.

Rick (15:30)
Yeah.

It's the but right now, like there's the way the only way I can publish is either cr no go in and understand the markdown file format that I need to understand or interface with Claude Claude to to do it. basically say, here's here's a post that I have, please please make it happen. And so I there I think there's a an opportunity for me to experiment with like building myself a back end that I can log into at RickliQuist dot com that lets me manage the content.

Tyler (15:40)
yeah, okay.

Yeah.

Gotcha. That would be a pretty different structure though from what you've got. Okay.

Rick (16:01)
Which could be a shortcut. Yeah.

Yep.

Tyler (16:07)
Cool. yeah, I don't have a ton of updates. Again, well, A, I was out most of the the last two weeks, but also, I I'm just doing HIPAA right now, which I'm busy, but I don't know that there's anything for me to say about it, aside from I couldn't do this without Claude, and I fucking hate Claude right now. Like, it's such this interesting thing of like so useful and critical to this project, and also I feel like

Twenty five percent of my time right now is spent telling it like, No, you idiot, we've been over this. Don't do it like that. So I'm that's my life right now. Sorry?

Rick (16:44)
How much are you using skills?

How much are you using skills, plugins, that kind of stuff? Yeah.

Tyler (16:50)
Not at all. Th this is Claude

Co work connected to Notion. So like Notion is the source of truth for everything in the HIPAA world, they called a HIPAA binder, because I think at most companies you literally print out a bunch of pages and put it in a binder and that's that's the documentation that if if someone from the government comes and says, Hey, prove you're HIPAA compliant, you you hand them this binder. And so that's it's that, it's making the binder.

Plus, of course, like the policies and the actual procedures at the company need to match what the binder says. I think we've got all the policies and procedures either where they need to be or someone's working on making the changes that need to happen. So my job is just put this binder together, which is just like, you know, there's 60 documents. There's got to be more than that, but interlinked pages, and it's like the way you're supposed to do it, I guess, is there's

Like you have to have a list of risks, and a risk might be one of our employees' computers gets stolen and whatever. And you just have to list all of the things that could go wrong. And then for each risk, you have to have a control and say, here's what we're doing to actually fix that. And then for each control, you have to have a recurring operation that's like every quarter we're gonna go in and review that we're doing this. So there's like something like six or seven of these different notion databases that are all saying the exact same thing, but with different language. It's just a nightmare. But I

I don't think it's like the type of thing where sophisticated AI use is needed. It's just like brute force. Go make sure everything is consistent.

Rick (18:19)
Do you have a shredder in there somewhere that you shred documents on a regular basis that are sensitive? Have you gotten to that one? No, like a paper shredder. Like is there a policy around a paper shredder that gets you taken to the to to the sensitive shredder shredder service every week or something like that?

Tyler (18:26)
Like w do you mean like a metaphorical shredder in notion?

I do remember when Zane Benefits did that. Yeah, we had like it was like a like one of those bank trucks, like an armored

truck would come and take all our paper and then take it to some off site location. Jeez. No. Well, n that's one of the things. So all the best practices about HIPAA are like a very enterprise and also probably very outdated. So they are all like there's a whole lot of office security stuff in there. If someone broke into our office, they wouldn't it's like, okay, you can look at our plants. What are you gonna do? We don't have any data in our office.

Rick (18:49)
And shred and shredded.

Yeah.

Ha ha ha.

Tyler (19:09)
Yeah. No, we do it would be very funny to be like, Every year we're gonna print out our HIPAA binder and then shred it. That's a security measure.

Rick (19:14)
Right.

Tyler (19:20)
anyway, that's my life. Not much to talk about there. how about you?

Rick (19:26)
we've launched our AI SDR. I should say JD has launched our AI SDR. we've sent over one thousand, I think we've contacted over one thousand leads according to like the latest milestone. I think we've gotten over fifty or sixty responses. Some of them are like not interested, some of them are you know, hey, like sure, like in response to the offer that that the AI did. And some of them are, you know, in between there.

Tyler (19:45)
Uh-huh.

So

let me pause you 'cause I know we've talked about this before, but it's been a little bit so SDR sales development rep the the normally a human that prospects and then gets sales leads to give to the real sales rep. this

Rick (20:02)
Basically, this is outbound prospecting. Like imagine cold

like a a a human would be cold calling and emailing cold lists of people, oftentimes that we have never talked to before or didn't even know about they existed prior to the outreach.

Tyler (20:17)
Yeah. And it f it gets

the list too. Like it the AI tool goes out and you give it like, here's what we're looking for. It scours LinkedIn or wherever, gets these leads, and then you said it emailed about a thousand people. And of those thousand, you got something like sixty responses saying, like, sure, let's talk.

Rick (20:33)
Yes, or not interested at this time, call me it'd be better to talk about this NQ four or not interested. You know, though but responses. Yeah, negative responses too.

Tyler (20:40)
the sixty includes not interesting, gotcha. Wha

what I mean, how many are positive responses? That seems important.

Rick (20:47)
I don't know. I need to

look at the data, but i enough to where it's like this is encouraging. so so two things. One, JD launched this without any help from anyone and he's feeling really good about it. And I'm and he's like learning and like adding more campaigns. So I think it's repeatable. second, we're getting responses that are positive and we're learn like it just it okay, so there was like learning and effort to figure out how to get these launched.

Tyler (20:51)
Yeah.

Mm-hmm.

Rick (21:16)
Now it's launched and now we're getting responses and conversations. It's like, okay, how do we have these conversations? And so it's like just a reminder of just how hard it is to do something new when you haven't done it before. The difference is what I love about this approach is the volume is high enough to where you're getting enough at bats where you don't feel like you have to perfect. And so what part of my message to JD right now is like, no, no, don't worry about being perfect. Like the fact that you got a response, like try different things. Like freestyle here, like you don't have to win it. The the point isn't to have a perfect conversation, the point is to learn.

Tyler (21:27)
Mm-hmm.

Rick (21:47)
and so what what a lot of the offers are is like, hey, would it be helpful if I sent you over some, you know, the latest like market rates across what what your options are? And of course they say, sure. And so Jay's like, I didn't expect you to, yeah, yeah. And so that's where that's where your tool comes in. and he's starting to use that more as like, hey, like here's a here's a quote I prepared prepared for you. Now that has a lot of work it needs still to to to be useful, but it but it leads nicely into like that's the

Tyler (22:01)
Gotta go get those

Rick (22:16)
That's the tool to use to fulfill the request. but anyway, it's still early. We I don't I I haven't seen a lot of the conversations that have like progressed from like, you know, our offer to them saying yes, please, to JD responding. And so I think there's gonna be some feedback from JD for you and me on like, hey, I need help. Like, how do I, how do I meet the like the offer is resonating? Yay. but now I don't know how to deliver on the offer. can you help, please?

Tyler (22:40)
Uh-huh.

Yeah, I mean that's great. Like the the analogy I've always used for this is obviously a funnel, but like a funnel with I'm mixing metaphors, but like it's a leaky bucket funnel, and you're pouring water in the top, and water's leaking out at each step, and some of it comes out the bottom, hopefully. The bottom of the funnel is generally the most impactful place to fix the leaks. But if you aren't pouring any water in the top, you can't tell where the leaks are at the bottom. So like

This seems to have unlocked the water is coming in at the top, and there's probably leaks in every step of the funnel. and now it's a matter of patching all those leaks, which honestly, that that always felt easy to me. Like in the if I think about the early days of lessoning CRM, I know a lot of people maybe don't they're used to like showing up to work and knowing how to do their job. And so it feels uncomfortable dealing with an unknown, unknown type of situation, or unknown unknown, I guess we're talking about.

But yeah, like when you can look at it and say, well, this part isn't working, this part isn't working, this part isn't working, that's just such a concrete thing to be like, okay, let's go. What do we need to send them in this email so that they reply? they they it was too expensive, so they didn't switch, or the timing was wrong. Like all of those are just it's it seems so straightforward at this point.

Rick (24:05)
Yep. Exactly. And what one of the responses that that came in, I I remember probably a year ago, you were like, Hey, we should run a campaign where we're just saying free health benefits. Like you don't offer benefits, we've got the perfect solution. That is resonating with people, like people who don't offer benefits are applying saying, Tell me more, like is there a way for me to offer benefits without any money? And and so I do think right right now we're targeting fifteen employees and above.

Tyler (24:15)
huh.

Mm-hmm.

Rick (24:31)
But I

do think there's a follow up campaign that we could go after that kind of brings back your hypothesis that targets that 10 and below with hey, like the new way to offer benefits is free. Here's how it works. you know, sign up today and get started.

Tyler (24:42)
Yeah.

Yeah, that's interesting. The flip side to that is the way we monetize that is by then selling individual policies to the employees. And we've we previously kind of said we're willing to do that, but it's hard to grow a business off of that. Like, is it good enough of a business to get a bunch of 10 person free accounts?

Rick (25:04)
The if we believe so the the data says that our best customers started out that way. Our best business customers were first individual clients, they then offered an HRA, they offered group health insurance. And they're and they're Yeah.

Tyler (25:18)
Okay. So I see two paths to that. One

is you're saying they're an individual client, so maybe they're like, it is a fifty person business, but only they individually sign up or it is a startup and they're they're growing quickly and they grow into it. D are both of those what you're talking about, or one or the other?

Rick (25:36)
It's more the the tech space, like startup founders. so like that's the t the sub segment like sweet spot to target with getting them on individual policies. and some of them are gonna, you know, turn over and and go do other things and the other ones are the the rest of some percentage of them are gonna, you know, skyrocket.

Tyler (25:54)
Yeah, that makes sense to me. I don't know if this is already being factored in with the outreach, but like if that's the case, it's I I I know in the past you've talked about who's the ICP and I feel like salon, like haircut people is just a a industry you've thrown out in the past. Like they're never gonna scale in that way, right? So they may be good free clients, but they're not gonna grow into eventually a group plan.

Rick (26:17)
Correct. but but I would I would argue that if we could figure out a package for a hair salon a multi location hair salon, that is a good customer for us to service because we should be able to convert and serve some percentage of the stylists to client the client base and they have turnover so there's new leads coming in constantly. So there is revenue there. It's just not the tier one revenue that I would I would say.

Tyler (26:41)
Yeah.

I assume Utah only has so many startups though. Like if you're sending it a thousand emails out per month, you're gonna saturate the number of startups pretty quickly, I would think.

Rick (26:51)
Yep. Yeah. And that's not what we're doing currently. so but but yeah, like and it would be nice if we had some sort of like monthly campaign that's identifying all the new seed stage or you know angel stage startups being launched or being notified and having like them be reached out to. Because I don't know, let's say it's 20 a month, you know, that are happening in Utah that get angel funded. I don't know what the right number is, but like we could identify those and then hit them and then when the when they

Tyler (27:08)
Mm-hmm.

Rick (27:21)
maybe we don't hit up get but they get a seed stage investment. We reach out. Like that could be that could be interesting.

Tyler (27:26)
Yeah. Yeah, cool. all right, so these outreaches are happening. Something like a thousand emails sent, sixty responses. We don't know the percentage of positive responses. but enough that JD's got like stuff to do. And now it's keep that going and then start plugging the holes in the leaky funnel.

Rick (27:49)
Yeah, and I would say like just to clarify, it's a thousand leads contacted, which probably means that there are this is multimedium, so it's it's it's email and LinkedIn messages. So there's probably something like a multiple of three times a thousand that maybe two, two thousand messages that have been sent. If that makes sense. Yeah, we've had forty one responses. So here's the here's the here's the numbers. Twelve hundred leads have been contacted.

2,000 messages have been sent. six hundred and forty-four LinkedIn connections have been requested, forty-one responses, and one meeting book.

Tyler (28:29)
One meeting booked.

Rick (28:32)
And most of the messages have been sent like there's a there's a massive increase in sort of like the number of leads I've been contacted in the last week. So like it looks like about half of these leads have been contacted for the first time in the last week. So

Tyler (28:46)
Probably some more responses are are coming in. Yeah. Okay.

Rick (28:48)
Are coming. Yep. And it looks about

like of all responses, it looks about like positive is about somewhere between thirty and forty percent positive. So, you know, fifteen positive responses.

Tyler (29:02)
Okay. And one meeting booked from that so far. It might be more, but Hmm. Okay. I would love to hear those numbers again in a month to to hear. This is one one of the hard thing. I know I spend a lot of time complaining about like metrics aren't as useful as everyone thinks they are. One of the really hard versions of this, I think I maybe talked about this on the podcast before, which is like we get a free trial user, and what you want to do is say, Did they pay it? Like it's a 30 day free trial.

Rick (29:05)
So far. Yep.

Tyler (29:30)
Did they pay us at the end of the 30 days? Yes, no, that's the number. But then I actually and I f the whole history of the company, I've used that number of like who's paying us 30 days after the free trial, maybe 45. I looked into it recently and the actual we get a meaningful number of signups, conversions from free trials, up to 180 days after they signed up.

You just don't know. You can you can look at how many people signed up for a free trial this month, but you won't really know who's gonna convert for like six months-ish. and I that's kind of the same thing here, right? Like who knows what the actual value of that campaign's gonna be? You probably won't know until open enrollment.

Rick (30:12)
That's the thing is like a lot of this is what what what okay, there's like what's happening now, and then there's probably some value that we're going to get from this campaign right now in October that we can't possibly predict. And that's what I'm very interested to see.

Tyler (30:24)
Mm-hmm.

Yeah. It reminds me so much of like back in the day before Less Annoying CRM, Bracken and I were trying to run a fantasy football website. And the the feedback loop, there's one football season per year. So like if you don't get someone it to start a league by sep September when the season starts, you don't have another shot until the next September. And so you're just working all year hoping that

Now we were doing this as a hobby. I don't want to act like it was a real business, but like, yeah, it's like we're gonna put in twelve months worth of work and we're not gonna find out if any of it mattered until next September. Not quite true for you. Like the leg up health can get customers mid year, but yeah. It's it's just so annoying not knowing if any of this is working. Yeah.

Rick (31:16)
No, seasonality's s yeah, seas

seasonality is so annoying. but I do believe like I believe it I believe this business is a snowball and it's like as long as we're doing the right things consistently over the course of the off season, like good things are gonna happen in the in season. but we have to show up every day.

Tyler (31:34)
Yeah. Yeah, a hundred percent. okay. I've got a a topic that's been on my list for quite a while. It's not like time sensitive for me, but it's been on my mind. So if you recall earlier this year, we did AI week. And th the the context for that was obviously I've been using AI for a long time, we all have, but Claude Code happened I think it launched like spring twenty twenty five or something, but really it had its moment.

Around the holidays in 2025. that's when I first I went from like, yes, I know like AI is ChatGPT to no, AI is claud code. that's when most of the world went through that transition. My team at Les Wang Serum had not was not following that. And so I did AI week early this year, I think maybe early February or something like that, to basically say, you don't get to write any code yourself for a week. You have to use cloud code for everything. We're we're canceling all our meetings.

We're stopping all of our normal projects, and for one week we're just sprinting on seeing what we can do with cloud code.

That was good for a lot of reasons. You know, the main point was to take a step change up in terms of how we're using AI, and I think it somewhat accomplished that. But the another way in which it was really good is it was just fun. it felt like a startup again. People were like we were hanging out after work. People came in five days a week, which is very different from coming in two days a week. it just felt energy, and we did like a happy hour.

After work, I say happy hour, it went to like 1 a.m. But the last Friday, we kind of went to a bar and hung out as a team after work. And the people who have been on the team l longer, like pre-pandemic, were just like, this week felt like the old days. It felt like when we really were a startup and in a good way. and so it's just been on my mind since then. Like, how do you how do you replicate that energy? Because there's a reason we don't have it anymore. I mean, one is

We're 16 years old. Like you just can't trick I I kind of teased you in the episode in the last episode that at Windfall, ever it seems like you're constantly ending a quarter. I mean, every quarter you are, but like that takes a month. Like a third of your life is the end of a quarter. And that's like a way to create a sense of urgency, but it's like kind of fake. Like I I don't want to do that at less annoying CRM. so like there's a natural reason to it, and also.

I don't wanna jump between priorities over and over. I don't wanna be like, there's a new project, everyone shift your focus. So anyway, there's reasons not to do it. I like coming in two days a week. I don't want to go in five days a week, but I do like how do we get that energy that that we're missing? I have thoughts, but yeah, what's your reaction?

Rick (34:18)
Yeah. It's yeah, I mean

I mean the this is the I think the primary idea behind goaling, right? Like having goals and that are time bound and measurable and have clear owners and that cascade through the organization. But there you're what you're also highlighting is there's trade offs that are negative by introducing that. But I I mean I think most companies do this by by having people commit to some form of of a a deliverable

on a some sort of form of cadence that is aligned to some larger thing that you're measuring so that it it and then you're you're rowing together towards that thing and there is pressure, there's time pressure on doing that. Like and there's different ways to set this. Like you can set the bar low and try to outperform it. You can set the bar high and know that you're gonna underperform and that's okay. but there's there's trade offs with all sorts of different approaches to this. But I don't know how you do it without setting

saying something like we want to do X by Y.

Tyler (35:21)
Yeah. Well n that okay, we basically have two teams, right? We have developers and and CRM coaches. It's easy to see how that applies to developers. Like we need to ship this feature. You can do something similar with CRM coaches, but it it's only motivating through a sense of fear and desperation, not excitement, which is like you've got to send this many emails every day. Or like it's not you're not working towards a goal per se, you're working towards hitting metrics, I think.

Rick (35:50)
Yeah.

Well that's I think that's how you've looked at it historically. But like I don't know, there's probably some metric that matters more than response time to your co to to the business that coaches could contribute to. it could be something like weekly act daily active users, like or you

Tyler (36:11)
They don't they

are so disconnected from that. Like

Rick (36:14)
The the yeah, and that maybe that's like maybe that is a opportunity, right? Like to connect them to that. I I don't I I would just yeah.

Tyler (36:21)
But I guess what I mean is

some jobs are just routine. Like this is a thing that always rubs me the wrong way when you hear about like kind of enterprise startup y talk is like everyone should be an entrepreneur and tell them the problem and let them figure out how to solve it. It's like someone needs to show up and respond to the emails. Like there's room for a certain amount of that. But at it and and at Windfall, where y'all are growing really, really fast, it's probably there's probably room for everyone to do that because every single employee can say, six months from now,

For every one of me, there will be three of me. And those people will be the the worker bees doing the work, and I'm gonna be the genius on top. I can't tell that story at a company that has been flat on employee count for literally a decade. someone's gotta s to to respond to the emails, and we don't really have a motivation problem to be clear. Like I think we have a good culture for people understand customer service is important, it's valuable to the business, we gotta come in and show up, but it just doesn't have.

Rick (37:04)
Yeah.

Tyler (37:18)
The energy that it had in the early days when we were gross.

Rick (37:21)
Yeah. yeah, I think it's hard. Like if you the problem is if you if you set a goal that is not that is disconnected from the routine, then you have like some negative side effects, right? Like where they're they're they're feeling pressure to hit a goal, but like what their core job is is is different than what the goal is. and then it's like, okay, well, now you're stressed out for no reason and up creating distraction from what I want you to be doing. So I do think like if it

It'd be interesting to think through this a little bit more because like I think it's easy on the R and D side. So I agree with you. Like you could just say b be more ambitious on the R and D side and be more deadline oriented, you know, time oriented. With coaches, like, I don't know, do they work on projects? Do they have things outside of the routine?

Tyler (38:01)
Mm-hmm.

Yeah. I

mean they have twenty percent work for sure. We've talked about this before that like a a d a kind of unpleasant reality of customer service is what what you want to do as the business owner is have the perfect number of people such that 100% of their time is spent doing customer service work. If you have time for them to do other stuff, it means you are misallocating resources. Like you'd be better off having one less support person and hiring a specialist in something else if they there's that much time.

Rick (38:32)
Yeah,

the the way I thought about this at Zane Benefits and People Keep was capacity sort of assumptions. Like what do I want? What is the target capacity for a customer support team or service team or a rep? Like you look at it on what's their capacity, what's the team's capacity, what's what happens if someone loses, like how much redundancy do we have, that kind of thing. Like I think like there's probably a target capacity in order for you to be able to set proactive goals for them that is higher that is

Tyler (38:39)
Yeah.

Rick (39:02)
their capacity needs to be the coverage ratio needs to be higher and than probably eighty percent that for for them to really have be able to take on meaningful goals. so so perhaps like what

Tyler (39:12)
Mm-hmm. Is sorry,

you're saying they need more than one day a week if they're gonna do anything worthwhile?

Rick (39:17)
Yeah,

like it probably is fifty-fifty versus eighty-twenty. and so could perhaps like goal number one for the twenty percent time is create the fifty-fifty by implementing workflows, tooling, self-service, that kind of thing. And then now you've got a a half a r a job that is half routine, half not.

Tyler (39:28)
Yeah.

Interesting side note, maybe I don't think this is super related to the topic, but that made me think of like a a a kind of change of mindset I've had recently. we've talked about how maybe AI could help with customer service one day. I mean, we we already are, but like, are we gonna need half our company to be customer service people long term? And I would guess the answer is no. In the past I thought of it like let's pull off one person at a time. Like let's say right now we have eight people, but in the future we only need seven. Pull off one person, give them a different job.

Now we've got seven people. Increasingly, I'm actually thinking a better model is keep the eight people and have two of them at 50% time. do you know what I mean by that? Like n not not the not I haven't explained why I feel this way, but you get what I'm saying. partially for this capacity reason. One of the really hard things about support is you there's like surges, you know. you do a product launch, something changed, you get a ton of emails all of a sudden, or like

Rick (40:22)
Why why do you feel that yeah, why do you feel that way?

Tyler (40:36)
We're not as seasonal as like up health, but like the first Q one is 20% busier or something than Q3. so part of it is to be able to handle that capacity where you either need to have enough people to handle the surges, or what most companies do is they just don't handle the surges. They're just like, you can't talk to support at this time. What I like about the idea of a larger team where people are kind of splitting time between things is you can flex that time. You have way more options to flex that time.

The downside, of course, is it means you don't have specialists as much. Like y rather than having a full time marketer, you have two customer service people that are combining together to do marketing. But I I there's there's definite downsides to it. But from a customer service standpoint, that feels appealing to me.

Rick (41:22)
Yep. Yeah, I I I g I agree. I agree. I'm not gonna argue with that at all.

Tyler (41:29)
so for example, we're toying with what like if we could have fewer customer service people, what should they be doing? One of the hard the one of the reasons I struggle to answer this is like we don't know how to grow. That's been a common theme. If I if I was like, I could put human labor towards this thing and it would lead to growth, I'd just be doing that already. but design is one that came up. And so now what we have is two CRM coaches are dabbling with design on the side to see if either of them, or hopefully both of them, have like that kind of natural ability to to

Rather than saying they're going like we're gonna have a full time designer from here, just say as much extra CRM coach time as we have available, we can put it towards design via these two people. anyway, that's sort of off topic, but made me think of that. Okay. good the goals, all that. I like that. I don't think it's in our culture. I don't think we're likely to do that, but I I think that is probably the generic answer to this question.

Rick (42:21)
You have project, like it doesn't have to be goals, like it could I think it's just like a culture of like committing to timelines on deliverables and projects.

Tyler (42:31)
Well,

so I think part of the thing, like what you're answering, you're answering this from the standpoint of like I am a business owner and I want my employees to perform really highly all the time. That's not actually my goal here. It's the energy and I think by definition it has to be temporary. That that's the thing is I don't think it's like, I don't think you can keep up a sprint all the time. startups do it by burning people out.

Rick (42:42)
No no. It's it's the energy.

Tyler (42:56)
Churning through people, but like there's enough growth and enough people getting rich and all that. But there's a reason startups talk about time timelines of five years, not not 30 years.

Rick (43:03)
That's okay, I like where you're going with this. are are you like a couple questions. So let's just say it's funny, like most R and D teams talk about the sprint, and there's always a sprint, right? are

Tyler (43:14)
Yeah. And we by

the way call them jogs for this reason.

Rick (43:17)
Yeah, yeah, cool. that's funny.

I remember this. I've we've had this conversation before. So do you believe that people need to be sprinting at the same time in order to and feel the energy, or can people have different sprint cycles?

Tyler (43:30)
Yeah, that's a good question. I mean I think I think you need some so the energy that I'm talking about is at least partially social and c based on camaraderie. So you need at least some other people sprinting with you on something similar so you can feel that camaraderie. I don't think it's essential that the whole company is doing it at once.

Rick (43:48)
yeah. So but some some meaningful number of people need to that work together need to be that are dependent on each other for work need to be sprinting at the same time in order to have the energy the energy. Yeah. Okay. Yeah. So there's some coordination. Like one one thing that you could test is like you could have one sprint week a month where people are gonna try to, you know, you know, we're gonna have like the third week of the month, the third the third Monday through the third Friday, or

Tyler (43:56)
Yeah, I don't think a solo sprint works, yeah.

Rick (44:16)
Whatever, I'm not sure if I'm saying that right. it is about sprinting and we're gonna just like make crazy commitments and just see how how crazy we can push what we're working on forward that week. And then we're gonna have a party, you know, happy hour on Friday to share the win, stuff like

Tyler (44:35)
Yeah. Okay, this is this is very similar to the direction that I've been heading in as well. Once a month feels is is a higher f I was thinking more like once a quarter. but because you know, but yes, like say, okay, everyone's coming in every day this week. We're getting lunch catered every day this week. We've got a yeah, party may be a strong word, but we're we're hanging out after work on Friday and celebrating. so okay, I think I think we're good on that. I I totally agree with that. I like that idea. Then that led me to

I don't think you can just say do your normal work but s but try harder. some projects are more receptive to sprinting than others. Like some of them can be vibe coded. Some of them you can move fast and break things, and some of them it's like, no, do not move fast and break do not break things with this project, right? So

Rick (45:22)
Yeah, may and maybe

it's maybe it's like maximize your current projects while and then if you don't if you are have extra capacity for sprint week, identify new try to help other people. And if you've you've you've maxed that out, identify new things to work on.

Tyler (45:35)
Well, I what I've been toying with is like giving in the what we did with AI week we said, put all your normal projects down. We're gonna give you special projects that I picked because they would be a good fit for a sprint week. Like I think you can actually finish it in a week. It's hard to sprint, it's hard to motivate yourself to sprint if the end of the week isn't you're not gonna be done. Right? If it's like this was a two-month project, but because I sprinted this week, it's now only a seven-week project. is not very motivational. But saying like,

If you can get this done by Friday and ship it, awesome. And if you can't, we're deleting all your code. It's gone. And you're moving you're going back to normal life on Monday. That that's the the the downside to this approach is it means we're not working on our top priorities. But if the goal here is to build energy and kind of it's about culture and morale and less about like we have to ship the most important stuff as quickly as possible, that's what I'm thinking.

Rick (46:29)
Yeah, I like it. Do it and report back. And I I would say the only thing I would say is like if you do it only once a quarter, like that you're you risk not having the enough reps to build the the the the muscle to do it. And so you might like start with a higher frequency and then move to quarterly once the team knows how to do it, to maximize it. But at the same time, like doing it once a quarter is better than not doing it at all.

Tyler (46:53)
Yeah, I I think you're right. I think the if this is about culture, like there's also a major cultural cost to saying you're required to come into work five days a week. and like we have a very calm environment, people are used to certain things. Obviously I could do it, like plenty of companies are in person five days a week, but it is a big it is changing the contract quite a bit, saying one out of every four weeks you're coming in every day.

So I think you're right. I don't think I have the courage to d to do that. anyway, so yeah, we're we're still planning it. I think we're gonna do this. I think we're gonna pick like a theme of projects. Like it's hard to we have eight developers, it's hard to find a project that all eight people can work on at once. Or even if you feel like you're working on the same project, what you do is you break it into eight subprojects, you know, whatever. So everyone's kind of working on different things, but hopefully they're related enough that that it all feels interconnected.

I'm still trying to figure out how do we involve the CRM coaches in this. it's really easy to make like a themed sprint week for devs. If again, the point is not we need to ship this, the point is like culture, morale, involving the other half of the company would make it a lot more effective. So still trying to figure that piece out.

okay. I think we're gonna do it in s September, October. It's scheduled. I forget I forget when though, but I'll I'll update when when that happens.

Rick (48:25)
I'd yeah, I'd be curious if there's like what what the observations are, like positive side effects, negative side effects when you do it.

Tyler (48:32)
Yeah. All right. Well I'll get back to you. anything else or should we call it?

Rick (48:37)
Let's call it. I guess we're we have a I don't know when our next recording is, but I think before our next recording you and I are spending some time in Minneapolis, so maybe we we do a live rec in person recording when we're together. yeah.

Tyler (48:48)
We've done that once before. I think it was in like

twenty eighteen or something. yeah, yeah, we're gonna see each other a week from Saturday. And then the next scheduled recording is the following Thursday after that, the J July thirtieth.

Rick (49:01)
Maybe that's the way to do it. I like that. We'll yeah, we'll do off the record conversation, completely off the record, and then we'll we'll provide a summary when we record.

Tyler (49:03)
Do a recap after we've done it.

A summary.

Okay, cool. Well I'll see you a week from tomorrow. Yeah, me too. All right. Bye.

Rick (49:15)
Really looking forward to it. All right. See ya.