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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.
00:00.90
Rick
Um, Tyler where have you been for the last month and a half.
00:02.49
tylerking
I have been trying to find my login for our podcast software and I couldn't find it no sorry dear listeners that we've been gone for so long we had to postpone the last one a couple times and then it just made more sense to cancel it. So we're back.
00:17.44
Rick
Yes, we are. That's true. Yeah I should probably look at the calendar and cancel or move stuff around. Although it might be kind of fun to do a half a half awake podcast. The reason Tyler's referring to I have a.
00:20.96
tylerking
Although you're about to have to take another break aren't you.
00:36.76
Rick
We've scheduled to have our baby the week of June Nineteenth and so starting there I'll be very unavailable. Yeah, ah we pre we pre-scheduled the baby. So we're.
00:43.73
tylerking
That sounds like you ordered your baby on Amazon like we did the prerelease ah preordered the baby.
00:54.00
Rick
We're we're currently ah shooting for a assuming everything goes as planned a June twentieth birthday
00:59.51
tylerking
June Twentieth cool so hopefully we'll be back on the every other week schedule at least for another episode or 2 and then break and then back to normal again. Hopefully um, all right I guess we should dive in how a lot has happened in the last month I
01:10.80
Rick
I Don't even remember the last time I talked so I can't even reference the last podcast.
01:16.29
tylerking
I think it was a month ago anyway yeah I guess I'll get us started here. 1 of the things I said was coming up was we were going to launch I'm doing air quotes here launch. Um, the redesign what we call 4.0 of lessnoing cm um I say launch in air quotes because we have not like. Forced everyone over. We're giving users the ability to opt in I think at this point maybe fifteen twenty percent of our users have but the launch primarily meant 2 things 1 um, all new people who sign up are on the new version instead of the old version. Um. And that's a big deal because like all of our current customers obviously are perfectly happy or happy enough that they're paying us for the old version. They're not the main target the main target with a redesign is new people. So I don't really care how long the other people take to switch over. Honestly. The other reason it's a launch is we we did a product hunt launch for the first time ever. Are you like familiar with product hunt and stuff. Yeah, well thank you? but.
02:11.56
Rick
Why I have liked it for like I saw you post on Linkedin for the first time in a year and so I had to like click the link and and like it because that's like that's a big deal. But yeah I'm familiar with it but like I'm curious like why you did that and what you're hoping to. Was it an experiment.
02:30.68
tylerking
It was an experiment although it's probably a bad experiment because like you can't do it again like the whole point is it's a launch. So maybe every time you do a major update you can like Relaunch but ah, it's not something you can do regularly So I'm not really.
02:33.36
Rick
Oh.
02:45.71
tylerking
I learned stuff I'm going to share it momentarily but I'm not really sure what to what to do with any of these learnings because like I can't I can't do it again? Um, but yeah, mostly visibility I Guess um I have mor to actually you know what.
02:55.37
Rick
Ah, interesting. What were you hoping to gain from this.
03:04.79
tylerking
Maybe I can just be like that annoying podcast host that like teases a topic and say something else and then come back to this because I actually think I have a different topic that's going to lead into that really nicely. So we have I think I've touched on this before but maybe haven't gone in depth on it that we have a new kind of growth hypothesis at less annoying serum. Ah in terms of how we're thinking about growth.
03:08.51
Rick
Okay, okay, right, go ahead, Go ahead.
03:23.98
tylerking
Um, and especially in terms of how we're thinking about the cost of customer acquisition. Do you know what? I'm talking about how much have I told you about this on the podcast before okay well listener. If ah, if we have and I'm boring you with repeat information apologies. We haven't talked in a while. Ah so yeah.
03:31.14
Rick
I Don't think we've talked about this on the podcast.
03:43.60
tylerking
Basically so let me give maybe more information than people care about and this would be better if I can share visuals. But if you look at our growth curve from when we launched early twenty twenty ah early twenty ten what it looks like is kind of a chart that goes up into the right not like super acceleration anything just slow steady growth. Until like 2019. There's some ups and downs but pretty pretty steady upward trend of our growth. So that means our position function our actual number of paying users is slightly curving up because our growth is increasing over time. Um, then in 2019 it starts to go down and it tanks as of the bottom. Like the first couple months of the pandemic those were the worst then it immediately shoots back up again and then it immediately tanks again back down to basically where the bottom of 2020 was and then we've been slowly creeping up since then I share this only to say if you've been listening to the podcast about a year. You. You're in some odd months ago I was like we've got a growth problem. We're going to get serious about it. We're going to start working on it. You remember this happening. Um, yeah, ah so we did a lot of stuff. It seems like maybe it's kind of working but I want to talk through a few things here. First of all.
04:44.47
Rick
Oh yeah, was right on the time we started the podcast.
04:59.78
tylerking
Um, so the growth dropped and then came back up and then dropped again and we were trying to figure out what to do and what we did is we looked at the second drop because whatever the first drop was who cares it's over we recovered from it and then it dropped again. So what matters is that second drop. Ah, first of all, turns out that probably I now think was stupid. I think what actually happened is the spike after the first drop was a complete anomaly I think 3 things like I could name exactly what they are but I won't bore people but like I can point to 3 specific things that went really well in our favor during that time and they pretty much account for the whole spike. So I think we dropped in 2019 and never came back from it. We just got lucky and we were looking at the wrong problem this whole time.
05:44.56
Rick
That is super fascinating. Okay, so what did you learn when you examined the first cohort of dropping.
05:51.53
tylerking
Yeah, so we haven't we haven't had the bandwidth to like do kind of legit data analysis of this yet. So I'm really just going off my memory and like some kind of anecdotal stuff. But. Around the end of 2019 we decided to completely change our marketing strategy and we're actually going to go after this travel agent niche I don't know I think I mentioned this on the podcast maybe or maybe that was when we were off I don't remember but we basically were going to. We had this whole new campaign and all that it never actually launched because we're going to go after travel agents and then the pandemic hit and travel agents are not the right.
06:12.63
Rick
Yeah.
06:23.43
tylerking
Business to target in the middle of a pandemic so we never did it but I was looking back and I was talking people like why were we going to do that and the best we can come up with is ah we had gotten. You know we'd gotten better at measuring ah roi and looking at like we had years of history on all these ad ad channels and we're like. We're spending way too much money per customer that we get um you know we we have to spend three hundred four hundred five hundred dollars to acquire 1 paying user who will pay us $15 a month and all the advice out. There says like you know you want a twelve month or less payback period. We weren't anywhere close to that so we basically looked at the numbers and we're like none of our channels are working. Why are we wasting all this money. Let's stop putting money into that and find new things to try. We just have to try other stuff that was the logic at the time any reactions to that before I move on.
07:11.39
Rick
What what I mean did you act on that did you turn things down turn things off.
07:17.42
tylerking
I think so I don't we didn't fully 100 % turn things off, but um, yeah, we definitely like took our foot off the gas a little bit because again it looks like it wasn't working my best theory right now is that that that was the mistake and. Have a lot more to say on this topic. But basically if we were at at that time I I don't know we're at 3 point 6 or three point seven million a are right now we were at 3 point something 3 point two let's say back then. You don't build a three point two million dollars ar business without ever having a marketing channel work and yet we were sitting there thinking nothing we've ever done has worked and we turned it all off and then we started dropping our growth dropped and so i. My conclusion here or at least my my hypothesis going forward is something was working or maybe all of it was working. We just didn't know what it was and because we didn't we were missing that attribution. We turned stuff off that was actually helping us quite a bit and that was the problem.
08:18.84
Rick
Um, yeah I like that. Well I mean obviously be nice to have attribution.
08:22.27
tylerking
So what do you do with that. Yeah, the problem is so why? why wasn't our attribution attribution working I mean we have tracking setup. We actually have a pretty sophisticated because it's all homemade. It's not like trying to chain together Google Analytics and all these other things. Like if someone hits our site like we store the cookie we track it from sign up all the way to them paying the problem I think is that the buying journey is too complicated someone you know this is not a transactional purchase someone sees lessing crm on g 2 and then. Six months later they see an ad on Google Adwords and then three months after that they see that we won number 1 on us news and world report and like how do you How do you attribute the the ultimate signup is they just Google less knowing Crm and we can't track where they came from how do you attribute that.
09:13.76
Rick
I mean I guess you just ah well cohort analysis would be 1 so if you knew that someone came to the website um from an ad in ah six months ago and then you know convert it six months later you'd have ah an understanding of like that ad being important. Even though it wasn't maybe important in the reporting period of the payment of of where you spent money.
09:38.80
tylerking
If the cookies still active. That's true. Um, most of the time I think over 6 months either. You're on a new device or you cleared your cookies for 1 reason or another I think it's hard to reliably track people over that period of time. Um I kind of think i.
09:50.90
Rick
Yeah.
09:56.81
tylerking
I'd I'd love if if you are a listener has an idea here I don't I mean I guess 1 thing people might do is capture the email address right away if you can.
09:58.41
Rick
Yeah, yeah, what's interesting is you have a very like self-serve sales motion for a product that is traditionally sold through multiple phone conversations and so like your competitors are are focused on like.
10:12.00
tylerking
On earth.
10:17.62
Rick
Converting people on the website as leads um, capturing like identifying them and then like running multi multi campaign attribution through the whole journey. You don't care about them until they become a customer I mean you know you don't you don't like yeah.
10:27.63
tylerking
Um, yeah, yeah I mean we care about them. But they're low value enough that we're not doing a sales call with them.
10:35.62
Rick
Well yeah, and you're not like actually like tracking them as a person like identifiable person until they create an account. So.
10:42.76
tylerking
Yeah, so I could try to like get them to give me their email address or phone number or something earlier on like ah you know hey you read this blog post fill out this thing I think even that's tough though because a lot of these places they're seeing us I think just talking to people. It's G Two. It's kept terra. Um, it's crm.org. It's sites where we don't We don't have the ability to capture anything from them until they click the link and they aren't necessarily clicking the link.
11:05.43
Rick
Yeah I guess ah um I don't know I Just it seems like there's either. There's there's some buyer journey that's like repeatable um and happening over and over again and so you should be able to look at like the the data in pockets and say oh like.
11:13.40
tylerking
Um, and we're tracking that for sure.
11:22.70
Rick
When we do a lot of that it leads to this over time when you know when we did that in January ah in December you know this happened? Um, yeah, if you have the data you should be able to like draw some conclusions I think.
11:29.21
tylerking
Um, yeah.
11:36.80
tylerking
I'm that sounds right? and that's kind of where my head's been at this whole time until recently. But it's just like there's such a long delay and it's not like you can't be like for the next eighteen months we're only going to try 1 thing. Um. So I'm actually kind of becoming a bit of a heretic here and saying like fuck all that data-driven stuff like I'm becoming like a brand marketing believer all of a sudden where so forever here's some numbers I do know for every I'll use Google adwords as an example I'm just kind of using rough numbers. But I think these are approximately correct for every person who pays us. There were about 4 other people who signed up for a free trial and didn't pay us for every one of those 5 people there I think 50 to 100 people hit our website that didn't sign up for a free trial so they clicked the link for every one of those I think there's something like a thousand impressions on Google now. Do they actually see the ad I don't know. But. For every 1 person who pays us there's something like 5000 people or whatever the math comes out to that. Got some kind of an impression of lessening serum and so this is kind of my leading hypothesis here of I think that there is a lot of benefit that is not being measured in this traditional performance marketing model. And when people say you need a twelve month payback period. It's not factoring in all of those other impressions that you got that you that you aren't attributing to the the cost.
12:55.50
Rick
Yeah, that that that yes, a thousand percent
13:00.67
tylerking
Um, so now what I hate about this is okay so like what you just spend endlessly on tons of stuff with having no idea if any of it works I don't know but vaguely the direction we're going right now is like I just want a lot it like when people are looking for a s um I want to be there. Um, so.
13:12.72
Rick
Yeah, that's I mean I love it. But but but you're also going to like you know, try to monitor the things that you're doing and the costs and the costs that you're spending and and and the impact of those things and the ah roi of those things in aggregate.
13:18.44
tylerking
I might have more up.
13:24.18
tylerking
Um, if if.
13:28.47
tylerking
Yeah.
13:30.55
Rick
And if it's if it's directionally right? You're not going to worry about the new like the pity pinching. But um, you know if something's clearly you know not working. You're not going to keep spending that on that.
13:35.97
tylerking
So a hundred percent so let me give you a specific example of that. Um, 2 different ad channels 1 is software advice. Software advice is a pay per lead thing where people call up software advice gets people on the phone. That want to buy crms and then they kind of match make they say hey we'll put you in touch with 3 crms and we're one of them. There's no impressions for lessening serum aside from the people that we pay for There's no other impressions so we know what like what the kind of surface area of the opportunity is.
14:00.37
Rick
The.
14:07.37
tylerking
Compare that to Google Adwords where it's like well potentially a ton of people saw the ad or maybe capterra is a better example. Potentially a ton of people see us on Captera the name lodges in their brain but they didn't click the link. So Captera has a lot more of this unknown magic potential than software advice does just as 1 example and so we're we're trying to kind of look at all the channels and.
14:21.10
Rick
Big ten.
14:26.33
tylerking
Guess at how much magic there is and kind of add a multiplier on top top of what we're willing to pay based on that. Um, so I know I already talked a lot but this seggues into the product hunt launch If you don't mind me continuing so like what did I want to get out of product hunt like the new theory is the buying Journeys along.
14:30.86
Rick
And it's interesting. Cool.
14:38.00
Rick
Yes, Okay, so keep going keep going. Okay, that's helpful.
14:46.60
tylerking
Requires many touch points I don't expect many people on product hunt to like go sign up and pay immediately. But if thousands of people see it is it possible that dozens of them a year and a half from now will have eventually completed their buying journey.
14:59.48
Rick
And who who knows how many people are going to product time typing in crm every day and looking at what's what's available on product time from a Crm perspective.
15:06.61
tylerking
Yeah, exactly so I can share some numbers on the product hunt thing as of right now we have 17 free trial signups from that I'll talk more about the actual product hunt launch itself in a second like what we did, but. 17 trackable signups. We got a hundred with I actually haven't checked in last week or 2 maybe a couple more trickled in but something like one hundred and seventy eight up votes for perspective like it resets every day. Do you know how product hunt works like at midnight pacific time they kind of reset the counter. So basically it's a daily competition you you the idea is you post yourself at midnight. If you're doing it carefully. Um you get as many uploads as you can and you want to be in the top few ranked for that day. It's kind of like Google search results. No one sees number 5 they see 1 2 3 or whatever. So the idea is get as many upfotes as you can presumably mostly from your friends and customers and stuff not from strangers. That bumps you up and then the stranger see you if you get high up we were ranked like number 10 or something on the day so we never really got that high that led to about 17 signups that we can track and then who knows how many of these unattributable unattributable ones there are out there.
16:17.65
Rick
Yeah, interesting.
16:20.61
tylerking
So have you like ever read about how to do a product hunt launch.
16:25.41
Rick
No, it's like it's we're so focused on Utah it's just not a strategy we would employ. Um, so yeah, yeah.
16:28.50
tylerking
Yeah I think I wouldn't be good for like up health anyway. But for it's kind of got the group on problem where like everyone's tired like why does anyone spend time on product hunt. It's a stupid product in my opinion like you just want to learn about launches. It's just like reading press releases. It's a feat of press releases. Basically.
16:46.68
Rick
Um.
16:47.58
tylerking
But I don't know people use it. Um.
16:49.99
Rick
It's a cool tool discovery place and then also inspiration place for ideas. But I mean I haven't I don't subscribe to product hunt today or or go to the website. The only reason I went to the website in the last six months was because you.
16:55.97
tylerking
Um, yeah.
17:05.55
Rick
Ah, post about it on Linkedin.
17:06.76
tylerking
Yeah, well I appreciate that. Thanks for the support I'd say probably like the the product on audience is probably not the right fit for us like we're targeting kind of a lower to like these are more tech people who are interested in the the meta game of products. Um, which is not our customers. It's probably a better option if that's not the case but the the thing I don't like if if other people are considering doing it like we sent an email out to 25000 people and said hey you know we kind of acknowledge. We're like this is a pain in the ass. You don't need to do this. But if if you're a big lessing s here I'm fan like here's a solid you could do us go up go because you have to sign up for an account and up vote Twenty Five Thousand I'm ish 25000 ish people hundred and seventy eight up votes. You got to have a big fucking audience and we are still rank number 10 right.
17:54.00
Rick
Yeah.
17:56.55
tylerking
You you've either got have a big audience or an audience of people who already have product hunt accounts and really like uploading stuff to get high enough for this to really be a meaningful marketing channel I think now having said that if you're the type of person who's let's say you've already got a bunch of Twitter followers that you can send over there.
18:04.47
Rick
Yeah, interesting.
18:14.64
tylerking
And you're just getting started if you really are launching your first product. It's like maybe those 17 signups would have been I mean ah that would be a huge deal for a company that currently has 0 customers it. It wasn't it was less than a month ago. So it's hard to say if anyone will pay yet. But um.
18:22.97
Rick
Did he did you get any paid users out of this or just seventeen free trials.
18:34.35
tylerking
I don't think anyone who signed up then has logged in in the last couple days so probably we might get 1 or 2 but we're not getting many paying users out of this. So that's my ah.
18:42.61
Rick
Okay, interesting. So you would you do this again. Note knowing what you know now or would you not.
18:53.50
tylerking
Um, I'm I'm not I definitely don't regret that we did it I'm glad we did it I think it will probably have some benefit to us. But the the reputational capital cost of like asking everyone like you said I posted on Linkedin for the first time in a year I wrote a Twitter thread. We emailed our whole newsletter. You can only do that every so often before you kind of burn all your reputation. Um, so I don't regret doing it because I didn't have a better idea of how to use that that reputational capital but I wouldn't say that this is like I don't know if it was worth the effort and all that but it was I don't know it was close enough that I'm not.
19:10.98
Rick
And.
19:27.60
tylerking
Upset we did it certainly and I I got to give a shout out to eunice our marketer because she really did the the vast majority of the work here and I think she did a great job. Yeah.
19:30.71
Rick
The the heavy lived in. Yeah I mean it was I I like you didn't reach out to me directly about this but I saw it multiple times like pop up in my feed.
19:40.11
tylerking
No well, that's cool. Yeah, yeah, again, who knows how many new people saw this for the first time it's hard to say so anyway and the the redesigns launch which is exciting so big stuff. Oh thank you? The the the marketing site is kind of.
19:48.47
Rick
Um, hey.
19:53.17
Rick
Um I like the new website a lot. Yeah.
19:58.61
tylerking
Mostly unrelated to the the redesign. Although our positioning did just change. Okay, cool. Thank you.
20:01.95
Rick
I really like the positioning is what I'm trying to say um, less knowing CM promises 3 things no other crm can emphasis on no other serum I like it.
20:11.45
tylerking
Ah, yeah, we talked about this in the last episode I think or or maybe 2 episodes ago. But yeah, it's it's actually our conversion rate went up a little bit when we launched this new positioning too. So not not not a lot but a little anyway I've been talking a lot. What's up with you.
20:22.30
Rick
I like it? Um, well I've been really busy at my day job with winful and so I've been trying to get a bunch of stuff done so that I can take a healthy paternity leave.
20:39.99
tylerking
Um, has that been a good forcing function for you.
20:40.31
Rick
Um, and then also yeah, kind of I mean I don't know that um I don't I don't know that I've necessarily done anything I would have done differently. Um, but I think like I'm building instead of building things that are dependent on me I'm building things that are dependent on on anyone. Um, or or and and not dependent on anyone in some cases just automating things. So yeah, it definitely affects like how I approach tying off a project where sometimes you'd be okay with a little bit of like manual work. It's just or if it's a little bit more complex. You just go Nope Can't do that got to make it simpler. Um.
21:00.44
tylerking
Um, yeah.
21:16.41
tylerking
Um, yeah.
21:19.20
Rick
But yeah, so that's been really busy. Um, the probably the biggest milestone since the last ah podcast is that Jd has taken over um the monthly update process and I don't know if we talked about this on last podcast I don't think we did.
21:35.28
tylerking
Yeah, can can you explain what? the what the monthly update involves.
21:37.49
Rick
But so at leg up health there's a month like 1 of the core things that we do for our customers. Um, is you know 90% of our clients at Legup Health don't have a health insurance issue that they need help with in a given month so part of what we're. We we offer them as peace of mind that we're keep an eye on their policy to make sure it's up to date. Um, they' you know they're using it correctly. The payment is is not ah passed due and so we send a monthly email just kind of confirming ah the status the status of. Our clients policies to every every person and um, we now have I think 1151620 some clients and I don't I don't know I signed up a lot of the original people. But I don't know any of these the new clients and so when I would log in once a month to help construct this monthly. Update which I was responsible for.
22:28.10
tylerking
Um.
22:33.61
Rick
Really like starting from 0 and like going what is going on plus as you have come to know I have I built a very manual fake ah software product to make this happen and so Jd has taken that on and so what? what it means is like now it's it's just like I I meet with Jd once a week. And there's literally nothing on the business that is dependent on me in a given month. So if I if I wanted to just not work on leg up help I actually could now and Jd is truly running the show. Um, now that that brings up an interesting question which is well well now that that's not something I have to do but like.
23:00.59
tylerking
Um, for her.
23:11.24
Rick
What should I be s spendingtting my time on and we've talked you know for if you if you haven't heard Tyler joined leg up health as a partner. Um and has been um, building our new application out but we as part of joining as a partner. We created a new monthly partnership Cadence. Um. And I ah, you know I brought this up at our last partner meeting and I was just like what what what? you know should I be doing and and the general of the two things that I I've been working on since that meeting have been one. You know trying to get positioning to a place where it's good enough to launch. Um with our new. Broader positioning to small business owners and I think we're on track to get that done for ah and before the baby comes and then after that happens it's basically just generate demand like be a rain maker and so I'm excited about that. But but there's a like up health has a different feeling for me now.
23:54.89
tylerking
I have. Um, yeah, yeah.
24:07.73
Rick
That I am not like every at the end of every month hitting this big deadline on this big project that I have to figure out.
24:12.51
tylerking
I Obviously we haven't seen the results of this yet. But I think there is assuming this goes Well, there's a lesson to be learned here that I've learned about myself so many times which is just like there's such a difference between spending time working on the things you're good at there's a huge overlap between things you're good at and things you love doing. For most people and like as an entrepreneur if you find yourself spending a lot of time on something that like isn't one or both of those things. It's not great for the business If you're putting a bunch of time into something that's just not your wheelhouse and I can't wait to see your demand generations.
24:49.81
Rick
A.
24:50.67
tylerking
That's your wheelhouse and you know finally like you've been doing a lot of you've been spending a lot of time on something that anyone could do right? okay.
24:57.91
Rick
Yeah, well I don't know about that I don't know about anyone but you sir like like you've taken stuff off my plate too with the product development stuff. Jd's taken the the customer service piece here and like the fake product product stuff and um, it's just man. It's just interesting. But yeah, ah. I'm excited I think I got to get this baby thing. You know taken care of um, but like I think you know by you know? August first we're going to be pretty much focused on growing heading into the busy season which is way ahead of schedule of any like anytime. And like a health and then also any time at my previous company people keep with how prepared we are. Oh yeah, it's very seasonal business. Um, ah no, but the the product was was was primarily the funding source for insurance so insurance cycles.
25:38.77
tylerking
Was was open enrollment a big deal that people keep okay I just because you didn't sell insurance there.
25:53.70
tylerking
Yeah, interesting, um, cool.
25:54.19
Rick
Drove the buying process and then you know the kind of the big update that that I haven't shared yet on the podcast is that April was a record month for us think we were um like 7000 in revenue something like that which is pretty cool for a month through revenue. No.
26:08.50
tylerking
That's awesome. That's like a real business I in my head I'm still like this is just getting off the ground and I mean it is in a lot of ways like it can't support like you and j d or or even just j d but like $7000 and Mr R is a pretty legit business.
26:23.89
Rick
It got bumped a little bit I should be transparent with like this one. We got this unexpected one-time bonus um, due to like hitting certain route thresholds um, and we didn't even we weren't expecting it so it'll go back down to like 5 or 6 k.
26:30.17
tylerking
Oh because the insurance agencies have all these like if you satisfy something? yeah.
26:40.14
Rick
But it's like 6 5 6 k now like recurring which is real and if we can get a 10 k going into next year um it's very real.
26:48.88
tylerking
Yeah, awesome. Um, all right I guess I'll take the ball back. Ah so tori our designer who's been with lessening serum for a while but kind of like she went through the coding fellowship where we teach people to code and then. Ah, came on as kind of like a designer apprentice. So she's been with us for a while but like was training and and just kind of learning the skills. Ah, but she helped a lot with this recent redesign and and now that she's more experienced is very very productive for us. She had like left for a while. Ah, because she's one of our few remote people and wanted to go like see if she could find an in-person job because just sick of the isolation of remote work anyway, dotdot. dot she's back or as least as of June Sixth she'll be back. Um, and upping her hours a little so we're gonna have her for 30 hours a week which is more than we've had her for.
27:40.43
Rick
Wow.
27:43.50
tylerking
As long as she's been like experienced. Um, so yeah, we're about to have like meaningful design resources kind of for the first time ever.
27:48.46
Rick
When I look at your new website who designed a lot of the images on that website.
27:55.60
tylerking
So that's if you look at the marketing site. That's mostly eunice or marketing person. Um, yeah, she is not a designer I think she has for a person who's not a designer. She has great design instincts I think if like someone who's I don't think Rick you have ah an eye for design I hope I'm not insulting here. Um.
27:58.52
Rick
Um, really like.
28:12.21
tylerking
I think units can make designs that look very good to someone like you someone who's a little more of a snob about it would look at that and be like this is not a polished website. Um so unitunices can get us to that level and then like Tori could take it to the next level I think yep.
28:25.47
Rick
These images that like have ah blurbs on them and like colored text like that's eunice. Wow yeah.
28:31.74
tylerking
I Mean she's a full stack marketer like she does data stuff. She writes the copy she handles all our webflow hosting does email marketing I mean she she does everything. So yeah, it's It's actually when you think about like like you know back in the day I did all that stuff and it's like it is kind of like a founder skill set of um yeah, just.
28:40.68
Rick
That's cool. Wow It's really good.
28:48.86
Rick
Yeah, it is yeah you're saying I don't have a ah good design eye and it did not hurt my feelings but it frustrates me I will say that.
28:50.87
tylerking
Whatever needs to get done. Get it done.
28:56.96
tylerking
I You all? Yeah I don't know it's not even that it's not a good design eye. It's that you're not up your own ass about design.
29:06.50
Rick
I Want to be like I want to have a beautiful site like this. It's not not for lack of wanting. Ah I.
29:09.28
tylerking
Ah, yeah, um I don't know to tell you Rick I don't either to be like I think I have more than you do, but as if I'm a I'm a designer in a way that you're not and I still I mean until. A couple weeks ago lessowing crm looked like it was made by a kindergartner. So ah, I'm also not where I want to be um, but yeah, I'm just I don't really any much else to say about but starting June fifth or whatever I said ah toial will be back and I also with our redesign finishing.
29:28.66
Rick
Yeah, yeah, yeah.
29:43.64
tylerking
I think we're going to for the first time ever. Our designs will be ahead of our developers like there are so many times where ah we give a developer a project and we're like okay we don't have the second half of this designed yet. So just start working on it and we'll get that I think we'll actually be able to like have full designs. You know every screen you need? No one's going to have to be like. Hey what happens if you click this button. You didn't design that part. Um, so I'm pretty excited about that.
30:03.59
Rick
Um, ah, that's awesome and what? what? Um, what is everybody working on right now. What is the like out after outside of the redesign. What is the the stuff that's coming in the pipe.
30:16.17
tylerking
So there's still a ton of work to do on the redesign and this is another thing like my opinion is you ship something like this as soon as it's better than the old version. Not as soon as it's done. So I bet we've still got another three months on the redesign for the full stack people. That's 3 of the developers. Um. And then we're so we're kind of working on the last few projects of our Api our new Api. We launched a new Api earlier this year but like it doesn't we just finished oauth I don't know if you know what that means but a certain way to authenticate with Api. We're about to start working on. Webhooks. Just kind of making the api better and better. So this is the kind of current 2 projects.
30:56.55
Rick
Let's just that's cool. Any other updates on the Api thing any more people partners.
31:02.91
tylerking
Um, no we we we have like a trickle of partners who build integrations and stuff but I do think that so far the Api project has been more so as a reminder for anyone listening.
31:17.12
tylerking
We built the api partially to make our like we wanted to get more integrations more people to integrate with us so we can be more like a platform. There's 2 benefits that one is the more integrations we have the better. The product is for our customers. The other one is every person who integrates with us if they have customers. They might send. We're sending more customers to them than they are to us obviously because that's why they build the integration at us. But we were hoping if we get enough of these they send customers to us. We've not really seen signs of that happening. Um, but it's a nice It's great to have a growth project that even if the growth part doesn't work. It still makes the product a lot better. Yeah, um, and it it is a lot a lot better.
31:51.34
Rick
There's value. Yeah yeah, makes sense that makes a lot of sense. Are you? Um, So would you say that you're focused like.. The company is primarily focused on growth right now like if if if someone's building something. It's like how's this going to contribute to growth.
32:11.90
tylerking
Yeah, but in a I would say in a calm way. We're not like we're not like sprinting sprinting a year ago when I was talking about this. We were still on a downward trajectory and I was like I don't know how low this can go um and it it felt a lot more desperate now. It's like it seems to have bottomed out and we're actually.
32:20.63
Rick
And.
32:28.95
tylerking
We're not trending up quickly I'd like it to be faster. But and we're not. We're kind of burning a little bit of money right now but we could go for a decade or something like that before we run out of money So we're kind of slowly calmly focused on growth if that makes sense.
32:43.87
Rick
Um, yeah, that makes sense That's good.
32:47.82
tylerking
Um, but yeah, we are we are about to with the growth. Update I gave earlier we are about to like restart investing a lot more in Adwords and all all those channels that we we already spend a little bit on all of them. But we are going to just be like if if people use this channel to buy crms. We're going to put pay some money. Yeah. We're going to make it rain and try and get in front of people. Obviously our competitors make it rain a lot more than we do.
33:10.99
Rick
Yeah, yeah, you've got to be be careful not to throw money away. Um, which's really interesting at leg up health. Um, we we spend $5000 a month on Adwords. Um clicks primarily targeted Utah health insurance queries um towards the end of every month we see a ton of traffic start to pick up.
33:13.48
tylerking
Yeah, for sure.
33:30.70
Rick
Ah, because of the deadline to get coverage starting the first of the next month. Um, and so I I can't decide but I think I should like turn the budget off in the first like two weeks of the month and then just like double it the last two weeks
33:44.85
tylerking
I Don't want to give I know I'm very open about almost everything but this is such a competitive thing where if you give your strategy away someone else can copy it. So I'm not going to say the specifics but I we do that with one of our channels.
33:53.49
Rick
Um, yeah, yeah I I do think that's that makes logical sense though.
34:02.48
tylerking
Um, yes, and another thing so we do it for a different reason for me. Obviously no, one's trying to buy a crm by the end of the month the way they're trying to buy health insurance but competitors spend their marketing budget. That's what we've found is some people run out and then the cost per click goes down later in the month Um, So yeah I and I think it's a pretty minor optimization. But ah, every little bit counts.
34:25.78
Rick
Yeah especially in low but budget numbers. Um, cool. Yeah, like it's ah it's interesting on the growth theme. Um, one of the the projects that we've been working on at leg up health is we hired a marketing coach and so I'm not actively working on any sort of. Demandn activities right now outside of letting the adwords run but we were working through this positioning exercise and as part of the positioning exercise jd every week is trying to get 5 or 6 customer interviews in place and we're targeting small businesses for this exercise. We've kind of figured out the consumer business and now we're trying to. Break into the the employer business. Um, we had some really good call lately man like we we had a hypothesis that startup founders and professional service. Firms were going to be our target customer. Um, our ideal customer and we're finding that cpas are actually the ones. That are are perfect for us. Not only are cpa's very stable small businesses at like 5 6 7 8 boys. They serve other small businesses usually locally. So. There's a local influence and if they refer it's such a trusted.
35:29.21
tylerking
Um, yeah, that's awesome. Yeah.
35:36.76
Rick
Advisor refer that there's like it's like it's a slam dunk sale like.
35:38.15
tylerking
Yeah, business has a cpa and a lawyer. Basically those are the 2 outside counsels they go to for help on stuff.
35:46.19
Rick
Exactly And so um, we're we're learning that us within professional services cpas and and tax advisors are our but our and financial advisors are our sort of so sweet Spot. They're super hard to win over. But because they have high expectations on service like out of themselves. They actually expect more out of brokers and they are therefore let down more.
36:12.42
tylerking
That's interesting I Also wonder like you don't offer tax benefits yet tax savings right with premium tax rate. Okay so a conversation you and I have had a lot in private I don't know if we've had it on this podcast but you have a lot of clever ways.
36:16.33
Rick
We do with the premium tax credit stuff. Yeah.
36:29.54
tylerking
To save people tax money when they buy Health insurance and my point is always nobody understands how taxes work They don't want to hear about Taxes. That's not the pitch and I still stand by that for the vast majority of people but a Cpa. I Feel like it's going to get disproportionately excited about the ability to get around some taxes if they can. Yeah.
36:48.53
Rick
Yeah, and help their clients with it in particular. Um, so we've we've had a couple of interviews with cpas lately and they're turning into clients and there' they're actually it's interesting. They're the hardest interviews because they just like they come in with this assumption that we're like this group broker who they don't trust. But then we quickly like by the end of the call. It's just one eighty oh I have a referral for you? Um, so there's some really strong ah there and and like I'm always scared to focus but like this feels like something that if we just focused on cpas. Um, if let's say they have an average of 5 employees.
37:10.47
tylerking
Wow, That's awesome.
37:25.48
Rick
And we go get um you know a hundred of these. We'd have ah half a million dollars in revenue from just Cpa's ah and they would refer like just there just their network alone would be enough to double.
37:29.88
tylerking
Um, yeah.
37:39.80
tylerking
Right? So I'm bad at estimating numbers I mean how many cpas are there in the state of Utah. Oh yeah, for sure because how how many there's like a few million people in Utah is that right? okay.
37:45.81
Rick
I don't know but I think there's got to be at least a hundred right? like yeah few million.
37:58.49
tylerking
Yeah, that'd be a cat I don't want to do this is like 1 of those old Google interview questions like how many marshmallows fit in a school bus like.
38:03.92
Rick
But we're really like Cpa start like serving other small businesses like it's at the subset of cpas that I'm talking about how many cpas in Utah no there are 665000 people cpas in the Us.
38:10.70
tylerking
Yeah, yeah, it's not okay that makes sense and you're not going after like the giant firms. So Probably the majority. Okay and I would guess the majority work either work at a big firm or like basically don't work at all. Um. Probably in the like below 10% of them are kind of in your sweet spot here. But.
38:30.48
Rick
Probably yeah but I and I'm thinking that like if we can just go find the 2 like get Jd list of a thousand of these and he goes and converts 10% of them into customers over the next year like yay.
38:44.12
tylerking
Yeah, so something like 1 in a hundred people live in Utah and if there's 6 you said six hundred something thousand cpas so that's something like 6000 I mean doing that math right? Um Cpa is in Utah presumably and then if let's say 5% of them are. In your sweet spot. Yeah, we're we're talking about a pretty good number of people there cool I like it.
39:07.43
Rick
Um, So so that's a that's a pretty exciting thing and the the thing I'm liking about this is that Ah, it's all J D driving it. It's not me doing interviews and then sure like trying to educate Him. He's like doing it and thenynthesizing it to me. And I feel like he is he his pace of of of entrepreneurial learning and execution is accelerating which I didn't know is possible at this stage but like it's It's actually pretty inspiring and then also um I think he's enjoy ah getting value out of it. Ah that what.
39:29.73
tylerking
No.
39:41.31
Rick
Wasn't there before um when he because he joined kind of after the first initial interviews.
39:43.45
tylerking
Yeah that's awesome because I do think at a startup you can't normally pay. You know you're not competing with big tech companies in terms of pay. There's sometimes longer hours. There's more uncertainty and more risk and like a huge part of what makes up for it is that. Sense that you're learning. You're growing. You're you're doing interesting work and finding a way to offer that to everybody you possibly can in the early days of the business I think is hugely valuable cool um all right I've got a couple more topics I'm just going to give the short one and then skip the next? um.
40:09.60
Rick
Um, yep.
40:20.41
tylerking
So we'll talk about it next time but the short one is ah so the coding fellows and one of our interns started for the summer so it's funny. Shelly my wife is a college professor. So right as students are leaving her. They're coming to me and so our schedules are exactly opposite every time she wants to go for go travel I'm like no, it's my busy season.
40:25.47
Rick
Um, name.
40:39.39
tylerking
Ah, but yeah, so things are things are very busy teaching a bunch of people how to code and coming up with projects and all kinds of stuff. Yeah.
40:47.35
Rick
That's fun. Um you this is you you say every year I think this is like the energizing part of the year for everyone move all the deaths around is it is it getting to the point where this isn't this is just like ah another week for you because you've done it so many times.
40:59.48
tylerking
Yeah, it's interesting. Question. It's certainly not just another week but definitely some of the excitement is I don't think it's that it's gone. It's that it's shifted to other people like before like it's like people. I've only met in an interview six months ago and I don't even remember what their faces look like are going to walk in that door tomorrow and I have to babysit them for lack of a better term for quite a while before they can go off on their own That's just a lot It's so much prep work all this stuff now it's much more like. Well Robert's got the interns and Eva's got the fellows she like one of our developers is kind of like leading the fellowship and I'm in so kind of the the support position. So I'm like yeah I've got to like sit in a lot of meetings and I've got to be present and and all that but there is a lot less preparation. Um. So I'd still say there's some excitement for me, but it's it's more handled by other people now. It's great though because like everybody like it used to just crush me. It's like lose a month of productivity and I'm actually getting some other stuff done right now. Um, anyway, yeah, there's probably not much to talk about there though.
41:56.93
Rick
That's cool. Get note.
42:05.54
Rick
That's awesome.
42:10.74
tylerking
Um, so I got an email from a listener who I won't name because I'm not sure if this is a topic he would want attributed to him but um, just like ah like an hour before recording this. He emailed me and asked a question that I thought we could talk about on the podcast which is. Basically how do you deal with kind of the so everyone says entrepreneurship has ups and downs like how do you deal with the downs. Ah you know you lose a deal a big customer churns. Ah an employee quits growth just doesn't look in the way it's supposed to um I realize Iss a broad topic. But.
42:33.86
Rick
E.
42:47.30
tylerking
Let's maybe see if we can get anywhere with this.
42:50.53
Rick
I Guess I would just say is it any different than dealing with any other type of like frustration I Guess the the big difference is that ah with entrepreneurship it becomes part of your identity and um, it's like this thing that you can't control um like you can your behavior. Um, and it's it's this thing that it becomes comes to define you and then how do you like sort of every time I find myself I guess I mentioned my the question every time I find myself in lows of entrepreneurship I have to I find myself either like getting unhealthy like the way I I first deal with it is unhealthy and I try to work more um and that's like.
43:25.40
tylerking
Um, ah.
43:26.36
Rick
Usually that leads to like a cycle that is not good and it eventually hits you and you're like oh this is something I need to do ah do about and the the way that that it always works out for me is no matter what the situation is is that it turns into a recentering exercise and it almost always involves separating my identity from. The the business and saying no I am Rick the person I am Rick the family man I am Rick ah who can do anything and I can go get another job if I want to and it's almost like removing the the pressure of of of it being successful for purposes of my identity but that does not remove the pressure of like taking care of people if you have employees.
43:47.12
tylerking
Ah.
44:04.95
tylerking
Um, right.
44:05.42
Rick
Or that so that still exists. Um, and and I don't know how to like deal with that stuff other than just to be real and um, try to take care of myself personally.
44:10.82
tylerking
Well, let me pause you before you dive into that so because I I think you just said something early, insightful but like let me rephrase it to to like how I'm hearing it is. There's kind of 2 when your business has lows. There's two problems one is perceived and one is real. The real problems is like I'm going to have to fire somebody or I personally can't support my family or whatever and maybe we'll put a pin in that and talk about that in a minute but a lot of them are fake but we're not fake but like yeah the things you were talking about is do you feel a sense of shame. Do you feel.
44:31.24
Rick
The.
44:43.46
Rick
That's that's a great point.
44:50.70
tylerking
Oh I could be more than this or whatever and it's like you're fine.
44:52.36
Rick
When you' an entrepreneur you set goals especially a bootstrap entrepreneur. The goals are arbitrary like in some cases they're like life or death goals. Um, but like for the most part like the difference between hitting a goal and not hitting a goal is like how you like feel like it's not like in and so choosing.
45:06.83
tylerking
Yeah.
45:11.64
Rick
To look at things differently is like a big part of dealing with the downs.
45:15.67
tylerking
Yeah, so maybe let's talk for a second about experiences we've had and and tricks we've used 1 thing that comes to mind for me with this when I went to founder summit last year I was carpooling with somebody who um I forget the specifics nor should I share them publicly anyway. But he's running a business with. Like a couple employees and they're making enough money to support everybody. You know they're in the I don't know 5 to 15000? Um Mrr I'm guessing um, it's not like crushing it but pretty good and full time work and stable but he he was kind of like. You know why? Why is it so hard to grow. We're not growing faster. He was around all these other entrepreneurs who are making much more than him and he was just feeling really inadequate and I remember kind of saying like you know how many people would kill to start a business that got to where yours is and he thought about that. He's like that you're right when I started this. I didn't even want this I just wanted to make a little extra money in addition to my job and now I don't even have that job because I'm supporting myself full time and I think just a appreciating like how good it is to be a modestly successful entrepreneur relative to anything else. That doesn't help if you're not even modestly successful. But if you are modest like that's a I think that's a good way to reframe stuff.
46:31.80
Rick
Yeah, gratitude is a powerful thing being grateful for the for what you have done and accomplished. Yeah I like that.
46:37.93
tylerking
And just remembering what the alt like I've never hated a job I've liked all my jobs but being your own boss is better than any job. It's so good.
46:47.68
Rick
Yeah, yeah, um I don't know like I I can give an example of of like I I feel like I'm not contributing a ton right now leg of Health and I always like I Mean. Work. Ah at ah at a highly successful venture-backed company with lots of money and and and revenue a high growth rate like and it's It's pretty demoralizing to compare if I were to compare leg up health to that Business. It's demoralizing and so I think like.
47:18.43
tylerking
Um, so.
47:23.95
Rick
There there are pros to every con and so you can figure out like I mean what I'm building with you and Jd is something that like I get a significant amount of non-monetary value from and I focus on that like the fact that I get to have a podcast with you.
47:30.46
tylerking
Ah.
47:43.88
Rick
Focus The fact that I get to have a partner meeting with you every month. The fact that like we're helping people like I get focused on the things like like are the are the the things that I get to do which is the gratitude piece. Um, ah and and worry less about like the comparison stuff.
47:58.31
tylerking
Yeah, and I think that segues the thing we put a pin in of like well sometimes it is actually it's not just a perception thing. It's a big deal but you talked about how if you compared leg up health to windfall your day job. You'd feel very inadequate at the same time. When windfall I I know nothing about windfall's business or how you'a are doing or anything like that. But like if a company like windfall has a problem. It's existential. It's we raised a bunch of money for investors and we could go out of business because we're not default alive if we do go out of business. We have to lay off dozens or hundreds of people. And our investors like there's so much more pressure on you I do think like 1 of the benefits of running a bootstrap business and like a calm company. Is it shifts a lot of things from like life and death to perception. It's like if you can get to that default alive. All of those problems just become a matter of of pride instead of a matter of survival.
48:56.96
Rick
Yeah, yeah, and then then like I'm I agree with the hundred percent and I'm I was thinking about like default alive like I feel like it's a it's it's this really nice thing but it's so easy once you get it to get greedy.
49:12.93
tylerking
Yeah, yeah, oh for sure I mean I I experience this all the time with my with lessening serum.
49:14.65
Rick
And want more. How much of that. Do you think is baked into this question is it like greed driven versus like perform like there's like there's like hey I I wanted this and I I got greed I'm now greedier and I won't more versus like what I wanted originally isn't like actually happening.
49:24.89
tylerking
Ah I don't.
49:28.86
tylerking
But no I I I don't think the person asking this is is doing it with from a place of greed I think a lot of startups right now are experience You know? Ah, even if whatever recession may or may not be happening. It. It doesn't seem like there's like a reces a. Global recession going on right now but a lot of industries are tightening their belts with the higher interest rates and all this other stuff. A lot of companies are their growth is slowing in a pretty meaningful way and I think it's more that where it's like yeah you know a modest. Like success kind of slowly growing would be fine, but maybe it's not even that.
50:06.66
Rick
Yeah, and I guess where where I was going with this was was less about this individual more about like in if you're are trying to evaluate like something and how you feel about it. Are you beating what you set out to do or are you failing to set do what you set out to do that would like be a very like important thing to.
50:22.63
tylerking
Um, yeah.
50:25.46
Rick
To check and like it's very easy like to what do you have successful to like stretch yourself, especially if you're a high achiever and go oh well I know I said that was the goal but like here's a new goal and um, you know separating those 2 things.
50:32.39
tylerking
Um, here's a new goal.. It's so hard though because that is healthy too right? Like very few people who have the ambition to start a business are then like. Well one of 2 things should be true. Either. You have no interest in running the business at all in which case just sell it and get out or if you're still running it presumably. It's because you you get something out of running it and that's probably related to achieving the next milestone Stuff. So I think like um, a healthy mental state for a founder is to.
50:50.29
Rick
Yeah.
51:05.90
tylerking
To be able to see that next goal. Sorry let me let me give like ah a weird anecdote from my childhood I went to a school district that I really value the sports culture at the schools I went to because we really tried we practiced hard. We played hard and we lost all the time.
51:21.84
Rick
He.
51:23.92
tylerking
We just were. We were terrible and I think like if I were to ever have a kid not that you can necessarily force this but I I would wish the same thing for them. Get used to trying really hard and losing and enjoying the the journey of trying. Because the the alternative people who don't try Suck. It's so boring like playing a sport or playing a board game with someone who's like I don't even care if I win. It's like okay this game's not fun Anymore. So like you have to try to win. You know? yeah.
51:50.17
Rick
Yeah, yeah, no, it's a kind competition is like fun. Um, ah I don't know like I I feel like um, a lot of this stuff that the the anecdote the like the kind of the the the mental model for this is. You know you? if you're feeling down about something and it's like really really bumming you Out. It's probably a lack of sleep nutrition or exercise that you need to focus on because like literally the difference between a good day and a bad day is your attitude and and you can change like the way you see a problem on a lack of. Personal health and a lack of sleep is like a boulder. Ah you know? Ah, but when you're you have a good you know, sort of like Baseline It's a pebble um in general the same thing There's just a drastic contrast between like how you perceive life when you're um, when you're.
52:27.22
tylerking
Oh.
52:43.59
Rick
Taking care of yourself So like generally like when I get into these roads like I I have all these like failsafes in my life to try to catch me when I'm going down this like vicious cycle of of negativity to try to get me to focus like on like oh no, just just go sleep and just go work out and just go you know, stop drinking and and ah.
52:56.89
tylerking
Are.
53:02.84
Rick
And sleep and then the next day I'm like oh well actually this isn't a problem at all.
53:07.55
tylerking
That's really interesting I'm glad you said that and I'm glad we're talking about this instead of me just answering the email I got because like that would not occur to me like I've just never not gotten enough sleep My my reaction to like fear is to go to sleep.
53:23.10
Rick
Um, yeah, got it.
53:23.71
tylerking
When I was in college and I had a really hard test and I'm like I'm not prepared for this I'd be like maybe a nap will help. Um.
53:29.38
Rick
That's an amazing like if you I wonder if your parents taught you that somehow because like I have the exact opposite reaction I like I go into like planning mode and I I stop sleeping.
53:37.47
tylerking
So to be clear I'm not saying like this is not healthy sleeping this is I've never suffered from depression. But it's sounds like when depressed people say they they want to sleep. It's like if I'm asleep I can't deal like I don't have to deal with this if I'm asleep. It's pure avoidance. It's not like.
53:44.78
Rick
With.
53:54.56
Rick
Um, yeah, but it's a but much healthier like coping mechanism than than not sleeping.
53:56.40
tylerking
I need to take a break type sleep. Yeah, yeah, probably somewhere in between is appropriate. But I know I'm glad you said that? So yeah, it could be your mental state now. But sometimes the reality is like there are problems and like I'm potentially in this with last night here right now like I'm not I'm not too worried about our growth issues. But you could argue I should be right. Especially if my thing about 2019 is true and it's like we've been having growth problems for the last four years like that's potentially pretty concerning. Um, one of like I think I'm just in denial in a good way which is I'm just like.
54:22.91
Rick
If down.
54:36.96
tylerking
I Have unlimited Runway not not money runway. But just I'm going to keep doing this until it works I'm smart I work with smart people I don't know if this thing we're trying right now is going to work and if it doesn't. We're going to try something else and that's going to work and if it doesn't I'm going to try another thing and if that fails Maybe we'll start a new side project. It's gonna something's goingnna work I don't know.
55:00.11
Rick
That is there that is the answer I think it's just like um if it's not this one. It's the next one and this journey is going to get me to the next one is the the worst case scenario is that this thing fails and it leads to something else. That is the worst case scenario and I'm okay with that. Yeah.
55:18.31
tylerking
Yeah I Actually yeah, can I be a bit of a a downer here for a second because I have a friend who start a um startup and it was like successful ish but not like successful enough that like I I don't know exactly how it ended. Did it get acquired. But if it was it probably wasn't huge I don't know exactly but like it wasn't I don't think he considers his success but it's like well you've been a founder. You've raised money. You've got a bunch of things to put in your resume. Ah, he had a hard time getting the job he wanted after that and I think the reason is it's like well.
55:51.00
Rick
Um, hey.
55:54.18
tylerking
You don't know what it's like to work for anyone else and we like do you really want to hire a true entrepreneur at a company I always have told myself 3 9 years as a failed entrepreneur looks better on a resume than that same amount of time as like a successful software engineer working at Google after this friend's experience I am. I am questioning that a little bit. You've done a lot of hiring at windfall would what do you think about that.
56:21.29
Rick
Um, yeah I had ah ah I think I think honestly it has less to do with um the person the the skillset and more to do with the person's mindset like I've interviewed a few like immediately leading founders hoping that they would be like.
56:30.89
tylerking
Are.
56:38.15
Rick
This person I could hire right away and most of the time they were dealing with some serious mental health issues. Um, and it's not like it's like about who they wanted to be and so like their willingness to be the janitor. Um, and just like you know they they wanted.
56:56.59
Rick
I don't know like when you're when you're a founder of a 2 person company. It doesn't qualify you to be a Vp at a 200 person company and and if if you think it does. You're not going to get any job because you have an ego and.
57:02.55
tylerking
Yeah, that's fair.
57:11.87
Rick
And so I think like I think the the hardest part that I've noticed and I dealt with it too. Um is just like putting aside this ego that comes from being the head of a small thing. Um, obviously if it's something successful that gets to hundreds of employees like that's a different thing. But if it's a.
57:30.25
tylerking
Um, right.
57:30.77
Rick
If it's just if it's a sub 5 person sort of thing that ah never really took off never really made any money. There's always going to be questions around like what what can you do at a larger company. Um and it it. Um I think it's a very hard transition to make if you're not willing to just sort of go into like.
57:39.65
tylerking
Right.
57:50.13
Rick
An ic role um or ah and kind of a first frontline manager role.
57:56.27
tylerking
That's interesting. Yeah um I realize that's a bit of a tangent I just took us on but it's it's interesting to say like this is the first this is a step towards where you want to be I agree with that and I'm an internal optimist and also I think the realistic answer is. It'll for almost everyone listening this podcast. We're all for the most part privileged have a valuable skill set. We'll be able to find work and all that it is possible that running a startup for 10 years That's like sort of successful but not successful enough. It is possible that that's not like. The most direct passwords where you where you'll ultimately end up you know.
58:34.13
Rick
Yeah,, that's true. Um I can tell you my opinion on this. Um I believe that like these people who who I've who I ultimately did not Hire. Um that fall into this category I think that they have a tremendous amount of drive and skill and like if it's mostly ego. Um, and not like like they're in their own way kind of thing. Um, and so I don't but I don't know how like I think that they could I don't know how you how you deal with that. Um, it's hard.
58:51.62
tylerking
Um, yeah.
59:00.10
tylerking
Yeah I also a situation that I'm thankful to not have to deal with but like less knowing serum's big enough at this point that even if we like stopped growing in any meaningful way. But we could support that just keep doing what we're doing. It's like you don't you don't shut down a 19 person company that's making millions of dollars a year. Maybe. You find a different person to operate it or you know maybe you make changes but it it continues existing I do you see on Twitter and stuff a lot of people who are like kind of like you said, maybe a 5 person business that's like profitable enough the founders are making money but they're not. They're not making as much as they would at another job. They're still working really hard and at some and they plateau and it's like how long do you keep working like a founder of a startup without seeing that that progress but where you have some It's easy if you don't have any traction then it's easy. But. Yeah, I'm not looking for an answer from you but it's a tough question.
59:54.79
Rick
No, it's It's hard I was thinking about that too. Um I think yeah like I remember I think in relationships my dad always had this saying when I was in a relationship and I was like I don't know what I want to do with this relationship. Um, and you go you'll know when you have a stomach full and ah like you'll know like and if if you don't know it's not time and at some point it's going to be ah it means it's like you're Done. You're like.
01:00:19.89
tylerking
So sorry I'm not getting that What does a stomach full mean in this case.
01:00:26.24
Rick
I Can't do this anymore I'm going to go to the next thing and and if you have any doubt about it being time to leave then it's not time to leave.
01:00:31.80
tylerking
I Know a lot of people who have stayed in relationships and I think I know people have stayed in businesses longer than they should have but you're saying.
01:00:40.58
Rick
I'm not saying that that I'm not saying any that that's not true I'm saying that um until you know until you have that moment like it's not, You're not going to leave so like so it's like it's just like this thing you have to like figure out and now if you want someone to come sit down with you and tell you like.
01:00:49.90
tylerking
Um, yeah, that's fair.
01:00:58.16
Rick
Stop doing this like that's what therapies for um, to help you think through things but like but you're not going to listen to me if I tell you like oh that's a shitty business. You should stop doing that like in fact, that might have the opposite and like mental impact of you like doubling down on it.
01:01:02.90
tylerking
Um, yeah.
01:01:11.74
tylerking
Yeah, it's also I think probably the case for the examples I was thinking of they probably did know there's a difference between knowing and having the courage to act on knowing. Um, anyway, yeah.
01:01:25.50
tylerking
We've noodled around here. Obviously there's no right or wrong answer but like.
01:01:26.10
Rick
I hope but I love these conversations with you because it's like it just gets into the weeds of like semantic and debate and I like I love it. Um, so I don't know if it's interesting to anyone else. But um I actually it makes me think too. So um, yeah.
01:01:31.27
tylerking
Um, yeah, ah.
01:01:37.25
tylerking
Cool Yeah to what? what? how would you summarize just like like condense down everything. We just said like what are your takeaways from this.
01:01:52.85
Rick
Ah, take care of yourself mentally and physically um so that you can approach problems with ah a rational mind. Um you know identify whether you're being irrational. Um, when you're ah evaluating a down. Um. And then like when you aren't being irrational and it's a real problem like deal with it sanely like and calmly. Yeah.
01:02:14.84
tylerking
Yeah, just one foot ahead of the other yeah and then another ah I agree with all that and the start to last mindset is turn as many of those real problems into perception problems as you can.
01:02:30.92
Rick
The other thing that we we didn't say and it's just like I want to say ah is that you can avoid a lot of stress by creating buffer for yourself and and and and not getting so like in a situation where there is so much depending on.
01:02:40.87
tylerking
Um, you know.
01:02:48.47
Rick
An unknown being successful and.
01:02:52.14
tylerking
That's a great point I know we're running up on time. But if I can give a little anecdote about less knowing serum here. So I said we're burning money right now. Also if you've been so followinging this section I forget what it is the tax code thing. We're going to have probably a two hundred and fifty thousand dollars tax bill above and beyond what we expected this year um we're also starting to think about. Ah if if we want to switch billing providers from stripe to paddle which is going to cost us tens of thousands of dollars a year. And all these things are hitting at once and I don't care because we got some money in the bank if we didn't have money in the bank literally lessening Sarah might be on the verge of going out of business like today if if we were at break even which we were in 2020 before the pandemic hit. We did not have any buffer because we were just like.
01:03:43.99
Rick
A.
01:03:44.51
tylerking
Every month is better than the last. Why would we? Why would we save money and then the pandemic hit and we're like oh shit. But thankfully it wasn't a big deal. It bounced back right away and we got ppp money but that was the wakeup call that we needed buffer and if we didn't have buffer right now I think we might I wouldn't be on this podcast because I'd be afraid to say we're going out of business.
01:04:00.76
Rick
A.
01:04:04.38
tylerking
So I Absolutely agree Buffer is probably the answer to everything here.
01:04:10.22
Rick
Well um, if you'd like to review past topics and show notes visit startolast.com I'll see you next week Tyler we'll leave it at that.
01:04:15.38
tylerking
See ah bye.