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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.
00:02.24
Rick
What's up this week Tyler
00:03.47
tylerking
I'm ah I'm back from ah Japan sorry we missed last week or two weeks ago everybody but it's been a month since last episode. But yeah I took a couple weeks ah to go vacationing.
00:16.14
Rick
That's awesome. Ah, would you go back to Japan.
00:18.56
tylerking
Yes I loved it. Um I like really big dense cities. Even if you don't do anything like just being because I live in St Louis which is I love st louis but just being in a a place with a lot of people feels good to me and Japan's doing that. Better than anywhere I've ever been. So ah yeah, I'd go back for sure. Have you ever been.
00:39.70
Rick
Do you I have not been to Japan but I heard it I've always heard. It's like super like another world in terms of culture and then I've also heard that it's super expensive.
00:51.40
tylerking
I did not find it to be that expensive. Um like that. What what you get is more modestly sized than America but like hotel rooms and stuff like that. Ah, they weren't worse than you know going to New York or London or any other kind of world city I don't think i. Actually was surprised by how cheap a lot of stuff was there terms of different culture. Yeah I mean it's not like you're on an alien planet. But there's a lot of like what to to us might seem like weird cultural things like you do not talk on the subway. It's totally silent on the subway and like you don't there are no trash cans anywhere. So you just carry your trash with you and you're not allowed to eat while walking down the sidewalk. So. It's just a lot of weird like not so like if it's so it's so wild. There's all these street food vendors. It's like the best street food scene I've ever seen in my life but it's a huge fauxpa to eat while walking.
01:33.44
Rick
What you're not allowed to eat while walking down the sidewalk.
01:46.10
tylerking
So you you can pull like step to the side of the street food vendor and eat standing right next to it but or take it to your hotel room or somewhere but like even drinking like you don't see anyone drinking a bottle of water while walking down the street in Tokyo ah.
01:59.91
Rick
Interesting.
02:02.25
tylerking
So but but like that doesn't really matter. It's not like oh I'm in a different planet it. It's still very much feels like a place you would know how to exist There's just a few little rules like that. Um I thought it was very cool though is fun. Lots of good history. Lots of ah, great food. Um.
02:16.89
Rick
Are go for it.
02:19.31
tylerking
Had a few ah random thoughts I wanted to share about it though. So one earlier this year. You said you're you're planning for windfall to you're you're expecting to travel more this year and you're trying to figure out how to get your sleep working. So I ah had a pretty big unlock for myself. This is the first time I've traveled with a pillow. Um. Have you ever done this you're you're looking like this is the most old man shit I've ever heard before. Okay.
02:38.72
Rick
No. Well, it's reminding me of a recent story that I need to tell you after you tell this So go ahead.
02:50.40
tylerking
Um, So my normal pillow on my bed at home is a purple pill purple is a mattress company I bought their pillow I Actually really like it. It's not for everyone but I like it and then my wife saw that they have like a small purple travel pillow and it fits perfect. My backpack has this weird little like. Compartment in the bottom that's for gym clothes. But anyway I can put the pillow on there. It doesn't really take any space out of my backpack I just have a pillow with me. It makes sleeping on a plane way easier and I used it to sleep in the hotel rooms. It actually helped my sleep quite a bit. Highly recommend.
03:21.47
Rick
Pillow is is a game changer consistent pillow but that's the first thing I noticed and ah and ah when I'm staying in another bed is oh man this pillow is not the same. Um, exactly exactly.
03:26.98
tylerking
Um, yeah, it's not even that it's worse. It's just not where you're used to.
03:34.17
Rick
Um, but this is a funny story so I was talking to I won't I won't disclose who this person was but another windfall employee who travels a lot and he literally stays at the same hotel every time and he bought the bed that they have in the hotel room for his main bed so that in the pillows, everything lenins like.
03:48.96
tylerking
Um, Wow That's I'm not sure if I'm impressed or is that some kind of like dystopia like ah I don't know but that's incredible. That's real commitments to your business travel.
03:52.40
Rick
It's the exact same bed and when he's in a hotel room.
04:04.60
Rick
Um I was like yes, exactly. Ah.
04:06.63
tylerking
Um, anyway I'd I'd recommend trying out a travel pillow if you haven't um the the next thing I mentioned we hired a travel agent for this and your response was travel agent still exist. This is incredible. This is like the best thing ever. Um.
04:13.88
Rick
04:22.61
tylerking
This was like a more expensive trip than I've ever taken but not like wildly more expensive. This was basically normally we go on 2 big trips a year we saved up the budget so we just kind of doubled the budget. Um, because we're doing one this year it's like a Japan specific boutique travel agent.
04:32.95
Rick
What service did you use.
04:39.43
tylerking
Um I don't know the name because Shelley handled it all. But ah, they like they kind of planned the whole thing that you know they they planned like as much free time as we wanted. But I mean it was incredible like we got to the airport we landed. There was just like. Ah, private driver waiting to pick us up so like no figuring out how the train system we we did eventually figure out how the train systems work but like that's not when you what you want to do first thing off the plane takes us to the hotel. They give us a wi-fi hotspot. So we've got like ah kind of cell phone data the whole time we're there. Ah. The next day like a tour guide picks us up and takes us places and then we've got like reservations at all these different restaurants some of which would have been very very hard like a lot of them. Don't speak english so it's like we couldn't have gotten reservations at these places without tremendous effort. We did a bunch of stuff we would have never been able to find on our own just kind of like because you know it's a Japan specific travel agent so they're like. We know what? what is good and what is bad and um, it was just like there's no way we would have planned to this good of a trip by ourselves and they they bill you for the whole thing. So I don't know how much did the hotel cost. How much did that driver cost how much of that private tour guide cost but like the whole trip was affordable even factoring in whatever commission. Or whatever the the asian took.
05:51.30
Rick
Yeah I mean what I'm realizing is that I'm learning learning this at windfall too is that there's this like kind of premier class of travel agency that targets um people like Tyler Rich rich affluent ah people in the us and. Ah, they basically build these like really custom vacations and um and so anyway, that's actually a really interesting target vertical for windfall to sell our services to we've actually signed up several ah like international travel ah services recently? yeah.
06:17.39
tylerking
Um, no interesting like they they buy data from you because I want to know who the rich people are to target. Yeah.
06:27.72
Rick
That's 1 concept but also like you know, ah you know? yeah basically understanding who in their database is you know able to spend what.
06:35.50
tylerking
Interesting side note on this when you travel like so I've never flown first class in my life or ah, a friend gave me his first class ticket for a flight from Detroit to St Louis which is not real first class I've never flown like real first class or business class in my life you go on there. There's like. Ah, hundred people on one of these big planes in these live flat seats. It's like $7000 to get 1 of these seats I know you're kind of jokingly calling me aff or I am affluent but like am I rich and sometimes I'm like yeah I'm rich I got a private tour guide like I'm I'm as rich as people get and then I'm like. I'm sitting back here in premium coach I did spring for premium coach a premium economy this time but I'm not spending $7000 and then I see the hundred people in front me on the plane doing this how many fucking rich people are there on this planet that all these people are buying these $7000 plane tickets.
07:24.65
Rick
Well, there's probably 2 factors there 1 There may be getting upgraded because they're frequent travelers to there may be business travelers they there but they might be business travelers. Their businesses paying for it that kind of thing.
07:28.73
tylerking
Um, but that that cost money too. Yeah, it's just incredible. How many it's not like oh there's 4 people at the front that get this special treatment anyway, apparently I'm not as affluent as I thought.
07:43.96
Rick
Um, it Yeah, the world is big is big but the world is also small. Um.
07:48.87
tylerking
Yeah, um, and then my final thought on the trip was as much I Loved It. Had a great time and the last few days but I was like I'm really ready to get back and I think that's a great feeling to be like ah hopefully or not. Escaping from the thing so much that you dread going back I Love kind of getting the escape but then being like real life is also pretty good. Well there's ah E I guy. Yeah, we're.
08:14.11
Rick
What's the Japanese term for this it it could it could got it could guy. Yeah, like yeah, but like that's like but yeah, like the reason like isn't there like don't the Japanese have like the longest lifespan because they the word of retirement doesn't exist in their language and.
08:19.80
tylerking
Yeah, we're both so ignorant here we we know we're talking about.
08:29.37
tylerking
Um, ah yeah, right? Yeah I I don't know the specific stats you just quoted. But yeah, every single person there. It's maybe my favorite thing about Japan was how much everyone takes pride in their work. No matter what their work is like.
08:30.79
Rick
They they maintain this. Ah what? we just the word. We just said it's which means reason for being.
08:47.34
tylerking
Garbage people have this like the garbage truck plays this like basically ice cream truck music and they like hop out and like have a spring in their step to get the garbage and like every single person just seems to take pride in what they do and the the flip side of what I'm saying is I it did make me think like when retirement age happens. Do I like is it a problem that I one week or two weeks into not working I was kind of like all right is this it like I'm just reading books and eating I need to work and and like you could you could flip that into a more negative spin which is like that's not. Like eventually that's going to be a problem. You know we'll see.
09:28.54
Rick
It's It's well yeah, we will like I ah I can't imagine not having something meaningful to work on in retirement. So I think you will be the same way knowing you.
09:38.19
tylerking
Yeah, yeah, anyway, enough blabbering about my trip. Thanks for listening. Ah, what's going on with you.
09:43.33
Rick
Ah, first men's group meeting so our our mutual friend Chase Murdoch has put together a group that is getting together every month. This is my I miss the first one due to pre-scheduled vacation. But I'm I'm going to my first one tonight um and so it it rotates different people's houses. So I actually volunteered to bring food and drink. So I'm showing up early to this brand and person's house I've never met which will be fun. Um, but it's a 3 hour ah session on you know, ah you know, kind of formal updates and and. Think today we're we're working through goal planning for the year and sharing our our goals. Um, and so it's kind. It's kind of like an opening meeting. Um, the first one was more introductions introductory meeting and and then I think we'll move into like a standard format after this one.
10:31.25
tylerking
Um, cool. So it's called the men's group. Okay, that's not the actual name of it.
10:34.99
Rick
I Don't know why I keep calling it. Men's group I need to stop saying that. But but ah, but but but it might be It might not be I don't know for some reason in my head. It's called the men's group. Ah I don't know if it's all men or not ah but because I've met any I've seen I've met people. Um, but it's it's meant to be like a mastermind group.
10:53.40
tylerking
Yeah, cool I like that it's 3 hours I've I've only done a couple mastermind type things before and they were shorter and I feel like it was always rushed. Um I assume with 3 hours you all have time to actually just this is what I really like about big snow tiny con conferences in general is you can.
10:54.19
Rick
Of some kind.
11:08.58
tylerking
Just sit there and hang out with somebody without every single minute being like what's on the agenda for right now cool So you'll report back on that.
11:18.80
Rick
I Will you know there's a confidentiality agreement so I'll have to anonymize any any takeaways but and be thoughtful about how I share but um, definitely I'll be reporting back on that.
11:21.73
tylerking
Um, sure.
11:24.89
tylerking
Yeah, great. Um, so I think in the last episode you mentioned it might be good to review our goals that we so we do this every year at the beginning of the year either late December early january we set goals for the coming year and then we don't review it at all until the next episode and I think. The way I feel I don't know if you do like you look at those goals a year later and you're like oh I forgot that's what I was supposed to be doing. Ah yeah so I thought it just go through. Yeah you want to you want to run through so we're one quarter in more or less. Um, okay, so my personal goals I said ah were.
11:51.30
Rick
I'm so glad you put this on here. Go like. Do you go first. Do your personal and professional goals.
12:03.30
tylerking
Maintain an exercise routine which is get 9000 steps a day on average each week so the the way I evaluate this is was a week. Yes, or no, so it's not like every day or whatever. It's do I average 9000 throughout a week ah get 2 rocks in and as a reminder that's rocking is carrying a £40 backpack around. Ah, 2 rocks and then two hundred pushups a week that was my ah kind of fitness and then I also have a weight goal of averaging under £140 I have done that every week except for 1 so far this year I miss one set of pushups one week because I just forgot um, but otherwise I think I've done it. I'm I'm feeling pretty good about that goal.
12:41.76
Rick
Are you I can't unsee ruckers now like I feel like ruckers are everywhere I go people rocking and so I didn't know a word exists before you set these personal goals. But that's awesome. Um, good good job. Yes.
12:48.14
tylerking
Um, yeah.
12:55.72
tylerking
There are dozens of us Rick um, the other personal goal was finish the house remodel and predictably absolutely nothing has happened on that we're waiting on the cabinet guy to get back to us. We've been waiting for a month. The contractor won't start until the cabinet guy gives him a timeline and so I know we're still in March right now I got to say it would not shock me if not only are we not done at the end of the year I would not shock me if we don't even start until late in this year so I hate this whole process. Big fail there so far.
13:29.10
Rick
Well let me tell you something at least you are coordinating the contractors we have a worse situation and that we have people because we're not the the general contractor we have people showing up doing work that was dependent on other people's work and then messing things up because they're out of order.
13:42.38
tylerking
Move.
13:48.60
Rick
And so we like went to redo the whole thing. It's really really painful. Um, so it's better to like do it take longer time. Do it right? than to like constantly have to redo it.
13:49.84
tylerking
Um, ah but sex.
13:55.70
tylerking
Yeah I do get the impression. It's being done right? like we hired an architect who's already done their job and they recently their their office burnt down and they hired a contractor to fix it and then they were like when we were considering that person another and they were like go with the other person we hear great things about them. Ah, so anyway, our architect tells us the person that we hired is great but it's going slow So We'll see ah professional goals see I said basically don't worry about growth unless something unexpected happens and what I meant by that is like we've got a plan. The plan is make the product Better. Ah.
14:20.10
Rick
Um, okay, ah.
14:31.36
tylerking
We're not going to see immediate results from that. So the fact that we're putting a lot of input in we're working hard and growth isn't changing is to be expected. Don't worry about it. So I have not been worrying about it I'm follow I'm saying still paying attention to growth numbers and stuff like that. But I'm not it's not like affecting my emotions or anything like that. So I'll give myself a check mark on that so far um, focus on customer delight if you ask a typical customer whether less knowing serum improved in 2024 their answer should be hell yeah ah yeah I think that's so.
15:03.10
tylerking
What we needed to do. We had a bunch of commitments from last year before we made this new plan and the plan was court q one of this year finish all of that so that q two we could really hit the grant like we could really go into this new strategy. That's that was the plan as of the end of last year we've basically hit it like it's the end of this quarter we have. Maybe we'll be like a couple weeks delayed on couple of these projects but we're we're done with all of our old commitments. Everything's kind of gone and and we're ready to we've actually already started a couple of our developers has started this new way of doing things so we'll have to see where we're at the end of the year but I feel like we've done the right thing so far there.
15:39.88
Rick
That's awesome.
15:40.90
tylerking
Yeah, feeling good so far. Um, maintain stability related to team culture etc. Unfortunately one of our developers announced. He's leaving so are we we've gone a little over 2 years with without anyone leaving and that streak is about to end bummer.
15:58.75
Rick
I'm sorry that's uncontrollable though I feel like that's still stable.
15:58.85
tylerking
Yeah, yeah, and he's not leaving for a different tech company. He's going into grad school and in a completely unrelated field. Um, and the plan is to still get part-time work for the first couple years of grad school so we're losing some of him. But um, yeah.
16:14.11
Rick
My gosh that sounds like a great situation.
16:17.48
tylerking
It's It's definitely yeah I mean I'd rather him not be leaving at all. But ah yes, it's when someone leaves it can be under kind of on bad terms or good terms and I would say this is very good terms so it it feels as good as it's going to feel when someone leaves.
16:33.51
Rick
But otherwise stability that's I would call that a stable exit. Um, ah a culturally positive exit. Ah any any other issues brewing or is this everything pretty stable.
16:38.95
tylerking
Um, yeah.
16:42.50
tylerking
Yeah, pretty stable. Um, you know it's so when I kind of look back over the last ten years um I've I'm I'm starting to kind of create this frame in my mind of like there's childhood years teenage years and adult years for a business like metaphorical. Um these eras and. I think we did really good in the child years where it's like me and bracken and Michael just hacking away doing our thing we did really well then and I think we really fucked up the teenage years just working on the wrong things didn't have like I didn't know how to hire didn't know how to manage all kinds of mistakes just from like kind of like running a business standpoint. And I think we're entering the adult years and I'm finally like it's like the midwit meme we're like the idiot and the the genius think the same thing in the person the middle like overcomplicates everything I think I'm finally getting back to the what the idiot thinks and hopefully hopefully because I'm a genius not because I'm an idiot but either way it doesn't matter. Ah. But yeah I think in the one 1 mistake I made in the past is I've like overthought a bunch of shit that didn't matter and not that it didn't matter but like I take a lot of pride in culture and stuff like that and a thing would come up and I'd be like all right for the next two weeks this is all I'm thinking about and I'd be like. Do we have the lights on in the co-working space or not, you know it's it's like stuff that's really not that important. Um, so I think I'm getting better at just being like if something matters I'll spend time on it and if it doesn't we'll just make a decision write it down in the wiki and move on you know.
18:08.91
Rick
That's hilarious because I remember coming to Utah and like these were like the number like the top issues that you were worried about and I was like dude but I but but I also admired it at the time and it's probably like.
18:09.58
tylerking
Yeah, yeah I know I know.
18:24.61
Rick
Like you could probably get faster to the culture that you want without those things but the point of that was you're prioritizing culture and you weren't sure necessarily where the leverage was ah versus where like it was it was getting into like you know my incremental improvement.
18:35.99
tylerking
I know we're we're giving our updates here, but this seggue is perfectly into one of my topics can we just do do it. So okay, so yes I I made a lot of mistakes over the last ten years and here's the question is if you let's say you knew all the answers I don't know if you necessarily did but you knew some of them anyway. But let's say you knew every answer.
18:40.50
Rick
Go for it. Go for it? Yeah yeah.
18:54.39
tylerking
And ten years ago you sat me down and said here's the deal here's how you should be doing everything here's how project management work yada yada yada would I actually be doing it right now like someone just telling you how to do it is that the same thing as learning it through experience.
19:10.78
Rick
No, but I do think that there's like an element of coaching like I think someone prescribing something is less useful. Although if you trust that person and you are open to it. It can turn into coaching and advice that you incorporate. But I think generally prescription is not the way you learn.
19:27.80
tylerking
Yeah, so let so let me we've we've got a specific scenario where so we have a developer who she this is a first job. She's ah she's ever had and so she has no no, not even internships or anything because she didn't major in computer science she mastered in it anyway. Ah so no experience at other companies. She's.
19:28.72
Rick
Um, it's experience.
19:45.77
tylerking
Entering kind of senior level here. She's you know, taking on some of the harder projects really doing great work here and so we're trying to level her up to like in the past it's been I Kind of say okay here's exactly what we want you to do and she doesn't She's good at doing it. But I'm telling her exactly what to do and she has asked for and I also support like. Part of leveling up to senior is taking a little more of that ownership herself and being like I want to I want to be able to self-direct more and like give me a project I'll kind of own the whole thing and so we're doing that and the hard thing is there's all these situations where it's like she's doing. All the whole front end before any part of the backend and I'm I'm like that is setting off warning signs in my head because in the past we've done this and it's led to problems or and you know just scoping things or that basically the analogy I would use is like I've touched the stove and burnt myself and I have like Scar tissue from it and I know I've learned those lessons. She hasn't touched the stove yet and I keep being like hey I think that's not the right like and not in a micromanaging kind of way like I think we have a good communicative relationship. But I'm like here's how I would approach it and she's like why like why? not just keep doing it this way and I'm I'm struggling with do I let her burn herself which probably. Wastes a lot of time in a sense. But maybe that's the only way to learn the lesson or do I try to just be like I'm the Boss. This is how we do things you know.
21:08.95
Rick
I I Love this topic. Um, so I go I go through a very similar thing in in revops at winfall in particular about yeah Junior employees because revops is like super critical work that touches multiple functions and like if you get something wrong I can like blow up the business for a day.
21:24.18
tylerking
Um, yeah.
21:26.57
Rick
Like like let's say this like we could take the crm down. As an example, we could blow up all the data in the crm we could ah you know, ah reroute leads the wrong way like all these like pretty critical operational projects and ah I think it's some combination of both. Um for my experience at least with with with trying to get yeah, ah. Less experienced employees to the point where they can own a project and there's 2 pieces I think to like senior project management that I you know one is like actually getting the work done without it negatively impacting others and minimizing sort of like the downside risks but there's also like sort of this general communication that you have to have which is like proactive. Like keeping people who need to know things without them having to ask it that that is like the the essence of good like senior execution and like when you're the founder. You don't have to communicate to anyone. Um, and so that's a big difference between I think you learning this versus that other person learning this is.
22:12.98
tylerking
Um, yeah.
22:23.64
Rick
Half of it's just making you feel her half of what she needs to learn here is making you feel comfortable with the approach that she's taking and that's a communication issue more so than her having Scar tissue or not.
22:27.72
tylerking
Um, and.
22:31.91
tylerking
I like that a lot because like the so the scenario she's going on sabbatical in mid-may and the project. She's working on we we don't do deadlines normally but it's like I really don't want to wait until after your sabbatical to get this shipped that would be a big problem if if the communication had been here is the plan for getting this shipped by that date. Here's the approach I'm taking I probably been like okay, cool and instead it was just like I'm I want to be clear. This is what like 1 of our star employees I'm not nothing I'm saying here is meant as a criticism right? but just like everyone learns the same way I did over the last ten years it was like here's what I'm working on right now and as far as I I can tell it's like. I don't know where this is leading I don't know you know are we going to get it done in time. So just communicating that there's a plan and and that yeah.
23:19.48
Rick
And then you can offer feedback on the plan. Um, which oftentimes is the way ah to to help coach. Um, you know is thinking through things ahead of time. So for example, like ah I'm I'm coaching someone right now through a pretty ah significant re-architecture of how we do lead reporting in salesforce ah, and. Um, part of what I like part there are 2 tactics I found helpful 1 is like coaching on communication like actively and then the second is um, showing like doing like walking how I build ah walking through how I build a plan for the project. Um, and ah structure it in a way to communicate to. My superiors. Um, and so I like actually working through the planning exercise in a shadow format was like a huge unlock recently.
23:56.76
tylerking
Um, yeah.
24:03.39
tylerking
Okay, so to to take that and apply it to this situation I think like I'm hearing 2 things 1 her goal should be to communicate to me what the plan is and 2 I I have kind of helped me and Robert and have helped. Helped kind of say here's how to write software here's how to do that side of the job we haven't done any training on this other part I've just kind of been like all right now you're doing it yourself and so I should I should sit down with her and like almost pair pair program but on the project management and the leadership side of things more? yeah.
24:36.36
Rick
Yeah, like the architecture side like let's let me tell you how to think through a project like in the in the multi like things and like you're gonna you're gonna get something wrong, but you want to minimize the mistakes and like an analogy I Always tell people is when you're doing this and you're new to it. Um.
24:41.56
tylerking
Are there.
24:51.14
Rick
You Want to make sure you understand the risk that you're taking um and you just need to be able to categorize them into 2 ways like imagine a boat. There are holes above the waterline and there are holes that it can take below the waterline. You just want to make sure the projects you're going to fail on are above the waterline. Um, and making sure that you have ah you're you're actively self-aware and getting ah consult. You know, consultation and coaching on the risk below the waterline.
25:14.84
tylerking
So have you found though. So that that's all very helpful. Do people still need to touch the stove sometimes.
25:22.27
Rick
Oh of course, but you want them to touch the stove above the waterline.
25:25.32
tylerking
Well so I mean maybe I'm not getting that analogy like I would think if if it's above the waterline. They don't actually burn themselves when they touch the stove you know like okay.
25:33.46
Rick
Um, oh they fail that you still fail. It just doesn't take the ship down. Ah so like like.
25:38.70
tylerking
What let them fail on a small project that doesn't matter rather than like oh the billing system broke or you know.
25:44.48
Rick
Well I think I think if they're working on it. Hopefully it matters So I'm not suggesting give them work that doesn't matter. But I'm just saying like the dependencies of that work shouldn't bring the the like for lessening serum. It shouldn't bring the site down because they learned ah they touched the stove. It should be you know.
25:57.27
tylerking
Um, yeah, okay.
26:00.37
Rick
They they shouldn't get cancer. You know they they should just get a little bit like ah, a little red on their finger.
26:03.73
tylerking
Okay, yeah, in that case I mean pretty much everything we do is above the waterline and like like the the failure in this case just means it doesn't ship before the spatacle it ships after So yeah, Ok, ok yeah I like that a lot. Um.
26:13.45
Rick
That's a that's a great feedback loop. That's very safe failure feedback loop in my opinion that you can live with.
26:21.37
tylerking
This is I think I kind of have a bad one of my bad leadership qualities that kind of baby people too much and just being like hey like if this ships before the sabbatical you win and if it ships after you lose I mean in different terminology than that. But like I I. I Feel nervous like putting pressure on people but like people who are really high performers kind of I think want that pressure especially like young people who are trying to level up. Um I should probably be more open to being like all right like like you want a challenge. Let's give you a challenge and there will actually be a way for you to Fail. And think I normally try to make it So. There's no such thing as failure and if there is a failure.. It's my fault not theirs. You know? Yeah, all the time.
26:57.95
Rick
Do you ever have conversations about like personal development. It seems like that like this is a like personal development issue. Um, and it's something that like are you are you? It sounds like you might be feeling like you're constraining personal development in some way.
27:15.49
tylerking
No I think I It's not that I'm constraining it. It's I think most people at the company like we have a culture at this company of most people are very much work to live. They're not trying they they want a low stress environment. They want me.
27:16.89
Rick
If you're not then I wouldn't worry about this.
27:30.31
tylerking
To take to to plan the project and to set the milestones and to make sure like if something goes wrong. They want it to be my fault not theirs. But there are a couple people and that that's thing we just don't have this culture for we have a better culture for the ah lifestyle worker than we do for the high performer I think. Um, where the the person who really wants to challenge themselves and all that I don't I don't think I'm good at shifting into. Oh you want the pressure all right like you can have it like here's how to do it. So um, again like I'm 15 years in keep learning stuff this sounds like 1 of those things I need to learn. Um.
28:01.47
Rick
Yeah, that makes sense. Yeah, and it's yeah that makes sense and I think that you'll figure it out.
28:07.51
tylerking
Yeah, okay, thanks, that's very helpful. Ah back to the goals for 2024 I just have one more which is protect coding time I said I should be averaging at least one full day of coding per week and I think coding or design but like individual contributor product work is what I mean by this. Um, and yeah I think I think I've averaged that there have been weeks where I haven't done any and there's been weeks where I've done 2 or three days but I think on average I've I've been getting at least one full day including this week I'm I'm back at it this week so ah I think I'm check check check across the board here. Yeah, thank you Thank you.
28:36.50
Rick
Woohoo. Nice work. Yeah um, ah, personal goals for me. Um, my first one is rebuild the exercise in writing habits I'm turning the right way on exercise I haven't really gotten to writing um ah but but I'm thinking about it a lot. So I Do think that. This will happen I'm on like I'm on track I would say Yellow um specific progress against the exercise habit is um, one I've got a Peloton now which is Fun. We should be friends on Peloton by the way I've only done 3 rides So I don't have a favorite yet. Um I've done 3 but 3 different people. Um I don't know their names yet. But i.
28:59.65
tylerking
Um, who's your who's your favorite instructor. Okay.
29:11.42
Rick
There's one woman who's like so smiling and bubbly that I really like um but I can't think of her name. Um, but ah second I ordered a tempo um workout thing which is like ah kind of like a mirror that that comes with a bunch of weights that puts you through weightlifting and so I've got that in sort of a compartment in the basement.
29:14.17
tylerking
Um, this.
29:30.43
tylerking
Um, cool.
29:31.72
Rick
So have a little workout area now. Um I'm doing pullups most days ah walks most days now. Um, and on Saturdays I've created a new ritual where I take my son to this community center daycare for 2 hours um and I get played basketball. So.
29:47.90
tylerking
Wow yeah, and does it feel sustainable or does it feel like it's January January New Year's resolution type thing.
29:48.59
Rick
Those are things all of those things were not happening prior to this year oh yeah no this is all very like incremental like continues improvement ah base. So I don't feel like I'm making any huge leaps. Um, you know the big leaps are making are are around making exercise. More like like easy like easier. Um I walk downstairs instead of having to get in a car. You know I you know that I roll out of bed I can jump on ah on a on a peloton kind of thing. Oh yeah, yeah.
30:11.60
tylerking
Um, yeah isn't owning a house So much better for this I mean you were in a house before I guess but like you have a lot more space now I think is that right.
30:25.51
Rick
Yeah, when you come visit and I'd love for you to stay with me sometime. It's just like you I think oh Bell youll ago like man This is so much better than what what I had in the past? Yeah, ah.
30:32.64
tylerking
Um I didn't see your old places so I actually but yeah, sounds good. Cool. Um.
30:38.62
Rick
So that you going? Well there. Ah once I get exercised under control I'll start shifting focus to writing and I'm doing kind of daily gratitude most days. Um, which is kind of ah like the initial start to a writing cadence. But I'm I'm starting to feel inspired which is great. Um, being more present with a family when I'm with them is another goal I've had I'm thinking of doing okay here I'm definitely intentionally putting my phone away and um I think ah being intentional about this I can do better. Um, so this is a good reminder for me to. Be even more present says sometimes I'm I'm trying to multitask and then ah regular dates was sable to per month minimum I'm failing here completely. Ah, but we you know I have I feel like I have good excuses. We've gone on 1 ah 1 date and it was really fine. We just need to do it again.
31:22.40
tylerking
Um.
31:30.59
Rick
Um, and then ah for the fourth. Yeah um, say sables got to I will not I'm going to deflect accountability here and say I am not the problem. Ah.
31:30.61
tylerking
Um, what can I ask what your excuses are just for a little accountability here.
31:42.64
tylerking
Um, ok, ok, all right fair enough.
31:47.96
Rick
Ah, sable Sorry I throw go to the bus here. Ah, sable's busy at work ah child care. Plus we've had a ton of stuff going on with the house and and parties and guests and so it'll happen. Um, the we have ah and then.
31:59.20
tylerking
Um, all right cool.
32:03.90
Rick
The final goal was 4 vacations this year um like true vacations with at least ah the next one scheduled at all times to look forward to this is true right now I've had ah we've had at least 1 vacation so far I'm taking a vacation next week um or like ah tomorrow Friday through Tuesday and then we have another ah beach trip schedule in july.
32:22.43
tylerking
Um, um.
32:22.94
Rick
So I just need to get before July I need to schedule our labor day trip and I'll hit the 4
32:25.46
tylerking
Awesome! and hopefully though labor day is not your last trip of the year either. So you should exceed the 4 Probably yeah.
32:34.79
Rick
Exactly yep, the the really cool thing. Ah that we got at windfall is like we have this access to this ah, one of our customer services called Ensperado have you heard of itsbrado it's like a luxury vacation application that.
32:42.80
tylerking
Now I haven't.
32:48.82
Rick
We're usually you have to pay like a significant membership fee but we get access as an employee benefit and so it's really fun to like scroll through that to look for vacation ideas I'm trying to I'm trying to find something that's kid friendly. Ah, that's the challenge right now is you know at at you know age 3 and close to one. It's like okay, what? what.
32:56.21
tylerking
Um, ask Paul.
33:03.26
tylerking
yeah yeah I I kind of admire parents who go on like cool adult trips with young kids like that like you know I I've heard people be like yeah I'd go to Japan I'd go to Paris and I'm not a parent. So maybe I can't relate but I'm that sounds like a nightmare to be.
33:06.16
Rick
What can we actually go do.
33:22.66
Rick
The travel is not worth it like I mean the Hawaii is probably as far as we would go just because we know that once we got there. It would be bliss. Um, and we went like it's not a place that you go to like leave the resort. Um, so that would be like the furthest we'd go Mexico seems a little hard. Um. With passports and you know that kind of thing so it's probably going to be somewhere in Utah or Arizona is probably where or California yeah, um, exactly ah and then um, ah, let's see professional goals. Um.
33:40.84
tylerking
Um.
33:45.81
tylerking
Um, yeah makes sense Kids kids don't know the difference.
33:56.65
Rick
First is apply the profit first framework at Legap Pt and pay partner distributions even as small check on the first part of this um we actually made the decision not to pay the distributions. Ah so I yeah yeah so i' like I've I set them aside. Okay, yeah so I feel like I said I would pay them even if they were small though.
34:04.40
tylerking
Well, it's in a bank account waiting for us I'm giving you a check I'm giving you a check on that.
34:16.44
Rick
And and we basically said that can we hold up for a little bit. It's kind of an administrative burden to take a hundred dollars and split it three ways. Yeah oh come on. It's more than that. Ah, it's like twenty bucks isn't it ten bucks
34:17.93
tylerking
Um, yeah to pay me like yeah a buck 70 coming my way I only well I'm not getting like an equal share I'm getting 10% of whatever you get and you're splitting some of I don't know what your deal with j d is but i'm.
34:36.31
Rick
Yeah, it's I think it's like you get like yeah five bucks I like that. Ah, um, so yeah, that's going well um, the next 2 goals are kind of the same thing you know part one is get legup help to 200 k and air are as part of that get jd to a start compensation.
34:37.42
tylerking
And getting like five bucks or something I bet but.
34:53.39
Rick
Um, those 2 things should happen if we do that and ah, we're at least close to it and what I am doing specifically to help with this is we're shifting Jd and I are pairing on on building the demand generation system and outreach to really help him get secure good meetings so that he can. Closes business. Um, ah and that's kind of this kind of translates into some of my updates if you don't mind. Ah so kind of the learnings from the last few weeks has been. We're we're making good ah system progress. Um, like we've we've we've we've got a good sort of framework for how we're thinking about data management. Um, you know, kind of. How we input new leads into the system how we qualify them and and do outreach and then how we would ultimately nurture them through marketing after that outreach segment ah phase. Um and so now we're so we're just going through the different steps of the system. Um. Where we are currently is. We're really good at like finding prospects um and sort of pre-qualifying them for outreach. But we're falling down on some of the outreach messaging and so Jd and I are spending time ah going through the messaging and you know I think the the big learning this week has been. We need to be a little bit more bold with our offer. Um that we're leading with when we're going out. Um, and we're settling on something like ah you know we are our new health insurance service that's helping employees um save money on. You know the coverage. That's right for them and ah you know.
36:23.76
Rick
You know we are working already working with you know, multiple Utah businesses like XYZ here's a link to all of our customer reviews out would this week or next week be a good time to see if there's a fit um and like getting a more aggressive with like hey we are for you. It's a no brainer. Let's get on a call and discuss versus trying to like.
36:33.85
tylerking
Are.
36:43.70
Rick
Do too much in an email or ah or ah, um, a phone call.
36:47.58
tylerking
Yeah, the the ah the previous version when you say do too much. You mean like it's explaining how it works and like why it's it. Yeah, and you're just saying. Yeah, so the the best version of this type of pitch that's ever worked on me I think came from demand maven which was that. Ah. Kind of growth consultancy. We hired last year I think it was the thing that happened there was I was reading their website and it wasn't like here's like here's the value we provide or anything it was just like does this sound like you ah you run a startup things were easy in the early days growth just happened naturally. Then it kind of stalled out. You've tried everything. You've tried ads you tried Seo Nothing Works you're not sure what anyway like it was like a paragraph that it didn't say what they do at all but it described my business exactly and I remember reading that and just being like well damn I have to talk to them. Um I wonder if like we know. What that story is for ah the perfect leg up health lead.
37:43.97
Rick
Oh yeah, like I think that's a great like second follow up email. So so what we're building is like a 3 touch cadence like the first cadence as a phone call with a live conversation or or voicemail a Linkedin connect and an email. Um, but it's basically like hey here's who we are. Can we can we you know does this week or next week work better like we're assuming that they're going to want to get on a quick get your call but what? what do we say next right? like it's annoying to say any thoughts you know like we don't want to be that. So um, you know the the next version could be something like hey. Um.
38:05.76
tylerking
Um, yeah.
38:09.70
tylerking
Um, right.
38:18.72
Rick
I sent you this message but I just wanted to to see if this sounds like you before before I move on like um, you know Boom Boom Boom Boom and I think there's a lot of I need to think through what the actual messaging is there but I love that tactic.
38:19.77
tylerking
Um, right.
38:27.40
tylerking
Cool. Yeah I Just know it worked on me. But yeah, that's great. So it sounds like the input is looking good. The output is tbd.
38:40.53
Rick
Well, what that that kind of shifts into like some of maybe like some negative learnings is um, we had a bet. Ah so one of our bets is just a system building and getting keep doing what's working um with employers. Ah, the the other bet was expanded Texas where jd resides. Um that had a sort of a setback this week where. Ah, we we tried to. We had you know 10 or so policies that we had helped people enroll in before we were licensed and appointed in Texas or we before we were appointed in Texas we were licensed at Texas when we helped them? um, but we we learned that the blue cross blue shield of Texas does not allow a consumer to ah. Ah, sign a new agent during the year which is completely crazy in my opinion but they're saying it's too much of an administrative headache now every Utah insurance company does this? Um, but um, you know we're not making a big deal of it right now we're just sort of tracking up to learnings and and working around it. Um, it just means that we'll have to wait until the renewal cycle to. Claim the customer as a new client. Um, so it's not It's just delayed revenue not not not necessarily no revenue. Um, but it's definitely one of those things where I kind of put this on like when I get loud at some point Legup Health is going to have enough clout where we can make some impacts on public policy and change some of these things. That's 1 thing that I want to zero in on is like I can. Ah, consumers should be able to fire their agent stop commission being paid and redirect that commission to an agent It's actually helping them at any time during the year
39:59.19
tylerking
Yeah I mean it. It kind of seems a little similar to the real estate thing that happened recently or it's like you shouldn't maybe I don't want to go too far with this because this might be bad for business but like you shouldn't have to pay every real estate agent the same commission regardless of how much work they do and what value they provide like. Giving consumers the ability to actually get value out of their ah agents rather than just having it be rent seeking like pay me my commission I'm not going to do anything at all. Yeah cool. Um, okay for my topics here. So I already talked about the.
40:27.55
Rick
Greed hundred percent
40:33.70
tylerking
Letting the employee touch the hot stove. So I'll skip that one? Um, yeah I probably need to go in about 10 minutes here so what's the right order I'll um yeah, so talk to sales updates. This is the thing I keep talking about this year where um, we're calling it tts talk to sales where Alex our sales guys kind of talking to more people. So first of all. One month in basically he started doing this in early March where um and by this I mean when someone goes to our website. We pop up a little thing in the corner almost like a chat bubble but it's not actually chat that's like rather than look around the website. Do you just want to talk to somebody um, prior to that he was spending all his time doing. Ah. Like buying leads and talking to them primarily through software advice. That's the main company. The best month he ever had. He's been doing that for about 2 years um with with a lot of time. The best month he ever had he got 11 paying accounts from software advice with 20 total users. And it cost $5500 to buy that set of leads. So that's the best month. The average was more like he got he spent $4500 to get 6 accounts with seven and a half users so he's he's been getting about seven and a half users per month which is not a lot right? Um March the first month of doing this talk to sales thing. He got 42 users um, which is pretty encouraging. Ah, all that makes sense in terms of like context of like what I just said.
41:56.30
Rick
So um I think what you're saying is you're getting 2 times twice as much bang for time spent for 0 spin marketing spend as you were getting for ah roughly 5000 spend a month.
42:10.00
tylerking
Yeah, and the twice as much as comparing it to the best month. It's actually more like 4 times as much. Ah, whatever I'm I'm doing mental math. It's quite a bit better compared to the average. Yes, now it's not apples apples because all of these leads were already on our website. Some of them might have signed up and paid anyway.
42:13.90
Rick
Or is that total.
42:21.92
Rick
M.
42:29.32
tylerking
So that that's the thing we don't know um, but probably ah we we have pretty strong confidence at least some of them wouldn't have some of them were like I was about to leave and then this thing popped up. Um, most of them. We have no clue but the fact that we're not spending $5000 a month and we're. Possibly getting better results. That's pretty encouraging I think yeah and it's not so sorry I said March this is for because we have a thirty day free trial. So most people don't pay until the end of the free trial. So we're at the end of March meaning people who signed up in late February are paying right now.
42:50.91
Rick
That's great.
43:02.52
tylerking
So basically most of the way through February there will still probably be some more people trickling in. So I think these numbers are actually low. Um, yeah.
43:09.90
Rick
Do you have? um, any view into like ah if you if you kind of put channels in play like you know, kind of ah, an online signup versus a sales assisted Signup and can you track you know as the sales assisted signup is going up through this effort.
43:24.42
tylerking
Are.
43:27.39
Rick
Whether or not ah the free sort of ah, not free, but like the the the website only sign up is going down or if this is like completely like ah like is the result of the increase.
43:40.40
tylerking
My guess is that the numbers I haven't looked at that. But these numbers are I think too small um because we add like 6 or 700 new users a month through the free or maybe it's paid that there's some overlap here someone could click Adwords pay. We pay for that and then talk to sales. How do you do attribution there but I I don't think we'd notice a 40 user like dip necessary like there's enough variance that I think it would be pretty hard to stress that out. Um, but yeah that it that is a good question I'll I'll have to put some thought into that. Um, but so anyway, yeah.
44:13.80
Rick
It be be good to have like a sort of a ah, a high level like is this thing working and is the machine working yes or no versus like maybe not necessarily knowing the detailed attribution.
44:18.16
tylerking
Um, yeah.
44:24.70
tylerking
I agree. Although I think I'm I think I have the answer of yes enough which is to say like I don't I don't know that the old thing was even worth it. Period um, and so just saving the money is helpful here and it just feels and that's not a great sign is it feels. So much more core like to some extent I'm becoming less and less data drivenve the more experienced like I'm going back to the left side of the midwit meme or the right side but like. But like 1 of the big mistakes I made in those teenage years is I was like okay like we literally one of our first hires was a data scientist. It's like we're going to measure everything we're going to track everything and the reality is to start a successful business. You have to do a lot of shit that can't be measured. Well I'm not saying this couldn't I think this could be but like if you do something and you're like. I know customers like this. They're telling me they like it and I have intuition and it tells me this is providing value to the world too often I would look at numbers and be like well the numbers don't show that it's good. Let's kill it. Ah. I'm trying to get back to the simple thing of like this is obviously good. Let's do it and this feels obviously good to me.
45:30.98
Rick
That's awesome. Yeah I I That's the right way to do things plus like this is just so much more aligned to who you want to be as a brand so like check like just move on.
45:35.64
tylerking
Right? Yeah I'll admit I've kind of had some like we hired Alex very early on with the hope like right when we hired him. He's a sales guy we we hired him because we got this big mlm network. That was like a potential multi thousand user opportunity that had just fallen into our labp and we're like here's a deal. go to go to franchise networks go to mlm's like get us all these big opportunities that was kind of the plan. It never worked out. Um, and then since then it's kind of been like you know he he works hard. He's very talented but like. We're not a salesdriven organization and that's his skill set. How do we fit together. This is the first time where I've been like Alex fits in exactly with what we're doing as a company and I don't feel like there's a mismatch there. Um, that alone is is worth a lot where like even if all of these people would have paid us anyway, they wanted to talk to a sales rep. Otherwise they wouldn't have clicked that button and they're all coming away with it having great things. They're like no one else I I reach out to 10 cms none of them responded you got on the call with me 30 minutes after I hit your website like it just feels. Yeah, exactly what? you just said it feels like the type of company. We want to be I'm just getting a lot of energy from ah from this project. Feel really good about it.
46:48.74
Rick
You're creating a virtuous cycle here. It's going to lead to good things. You can't you don't need to worry about what it is yet.
46:52.51
tylerking
Yeah, um, and so we haven't shipped yet and Alex on vacation. But once he's back. We I just finished building a new feature which is um, he'll be I've already talked about this on the podcast. But basically he gets a report of all of the people who are doing live demos meaning trying out our product without signing up for a free trial. Um. We added a question to that like you suggested which is how many users do you have um and so he's going to see a list of everyone who's doing it how many users they're going to have and he can just push a button and it'll pop up a thing in the app that's like hey rather than figuring this out on your and like Alex is free right now. Do you just want to talk to him right now. Um, so we haven't tested it yet. But I'm pretty optimant. Right now Alex has a bunch of these calls scheduled throughout the day but there's like weird gaps where okay, no one scheduled a call for an hour he can just take that hour and be like I'm just going to go push this offer to as many people as I can yeah I'm I'm I'm pretty st yeah I know i.
47:37.33
Rick
Love it. That's this great like if you just do like little things like this every month like by the end of this year who knows what's going to happen.
47:46.95
tylerking
I don't know that I have like enough ideas I really like the idea because I like building product and I think as the founder I should be working on growth. This is the first time in a while where I'm like I actually have good ideas on things I can build. Yeah, yeah, um, and then.
47:59.78
Rick
Um, means he's working on the right stuff. He's uncovering things so keep going.
48:06.38
tylerking
Ah, kind of like an add on to that is I was thinking about this that just yeah, we've talked before in the podcast you and I back when we work together. We kind of had this ah budding heads where I wanted to build everything in house and you wanted to outsource everything and i. Again I think you're mostly right about it. But I actually have been thinking more and more about because I'm building a lot of custom stuff for Alex to do this talk to sales thing and I've been thinking that like I think there might be a nice way to differentiate yourself by building by making the sales experience. Part of the product experience if that makes sense like like don't just be like oh here's a Zoom link but can you really integrate your getting the demo and we're you know we're ah like like you're you're trying this up. Yeah, yeah, exactly.
48:52.92
Rick
You're getting the product you're getting the first version of the product. Ah the free, the free me in version if you will as part of this.
48:58.40
tylerking
And so I've been exactly and I've been thinking through like does this apply to every company and I think the answer is no actually you're you're shake you're saying Yes, maybe it does but exactly what we're doing.
49:07.48
Rick
Not yeah, not necessarily online world software. But yes, like the first interaction with ah a brand should feel like the first interaction of the product experience.
49:14.25
tylerking
Oh sure, That's okay sorry I agree with that I guess what I mean is like is building custom sales tooling a useful thing to do for every ah company and I think probably not um so then I was thinking. Well why is it.
49:22.94
Rick
Different question.
49:29.60
tylerking
Why do I think it's a good idea I haven't proven that it's a good idea for lessening s hereum and I think the sweet spot we're in let me know you think about this is totally self-serve product but where you're talking to people that strikes me as where the opportunity is if you're like full on Enterprise like.. The product itself has nothing to do with the sales process like you're like you have someone book a call with you and callendly talk to them on Zoom You don't need you can use entirely off the-s shelf products for that If. You're fully self-service. Obviously you're spending a lot of time customizing onboarding and like that's that's a given everyone already knows that. Feel like there's this middle zone where we're in where it's like customers can sign up for the product they can use it themselves. They don't have to talk to us at all. But if we the customer service for us is a part of the product and if we can let them taste that while using the product and I don't think you can do that without building some amount of integration here.
50:24.88
Rick
Um, I think what you're saying is that if customer service is a high differentiator for your offering. Um, it's unlikely that you're going to find an off the toolshelf that makes it easy for you to to triple quadruple down on that differentiator.
50:37.94
tylerking
Um, yeah, maybe that's right.
50:41.12
Rick
Ah, otherwise ah you have to it just requires custom software development at some point to get what you want which maybe is a business opportunity for someone to build that um because it seems like that's something that's very solvable with a crm like tool. Um, but maybe not.
50:49.13
tylerking
Um.
50:55.13
tylerking
Agreed I I thought about I actually thought about you know I think us entrepreneurs are always like what if I go start that company. Um, and I thought about that I agree there could be an opportunity there that my only questions are there enough companies where customer service is that important to them.
51:00.26
Rick
Yes.
51:11.57
tylerking
Maybe the answer is yes but I feel like for most companies customer services like they're trying to reduce cost more than they're trying to be like how do we make our customer service almost like a sales team which is kind of what we're doing here. But so maybe there's an opportunity there. Maybe there's not but I think there's definitely an opportunity if you're starting a new business to say.
51:20.77
Rick
Me now.
51:30.83
tylerking
We're going to. We're going to follow this model and really build a human in the loop into the free trial process The you know demo process. Whatever it's so far working pretty well for us and I think it could be repeated in other businesses.
51:47.57
Rick
That's cool.
51:47.86
tylerking
Yeah, um, so I'm excited about all this so I got a run I got a meeting coming up but ah, good talking to you Rick.
51:52.99
Rick
If you'd like to review past topics and show notes visit starve tolast dot com see you next week
51:56.83
tylerking
See ya.