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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.
00:01.28
r
What's up this week, Tyler?
00:03.27
Tyler King
How much you're, you're in a hotel right now.
00:06.47
r
I'm in a hotel. I'm in San Francisco this week. Um, and it's fine.
00:11.58
Tyler King
So it's an hour early cause we record this at 9 AM my time, which is normally 8 AM m your time, but now it's 7 AM your time. Cause you're in the Pacific time zone. So I hope that coffee's doing its job.
00:24.52
r
It's, it's not, uh, yeah, I, I, I struggled. Uh, it was a rough travel day. My, my flight got moved, you know, ah delayed. I had to get a different flight. I didn't sleep all the night before. And then man, last night, I just don't sleep well in hotel rooms. i I wish I did because if I did, I'd probably catch up on sleep because it, you know, it's probably better than.
00:47.68
r
being around two, two titles, you know, two, two, two kids.
00:47.96
Tyler King
Having kids around That I Yeah, I I don't but it's my own fault because I don't have cable at home when I'm in a hotel room I'm like, I'm watching HGTV.
00:50.59
r
Uh, but man, I just, yeah, I just don't sleep well in hotel rooms.
01:03.53
Tyler King
I'm leaving it on all night That's my guilty pleasure.
01:05.83
r
What is, what is HGTV?
01:08.86
Tyler King
It's this terrible TV channel. It's just like home renovation shows. And they're like, we we redid your house in seven days. Look how nice it looks. It's absolute trash. But both Shelley and I both really like HGTV and can't watch it at home.
01:23.79
Tyler King
So when we're traveling, we're just like, we're going to inject that into our veins.
01:28.23
r
I feel like this is something like a stoner would watch. Are you saying that you like to get stoned and watch a random TV shows?
01:34.87
Tyler King
No, I don't think it's stoner TV. It's more like it's the trashiness of reality TV with none of the drama. It's it's just watching people buy houses.
01:45.81
Tyler King
It's so stupid.
01:46.01
r
Okay.
01:46.76
Tyler King
Anyway, anyway, I do it to myself. um Well, sorry, you're tired. I know you got a long day ahead of you. Hopefully you make it through.
01:53.67
r
Oh, it'll be fine.
01:53.75
Tyler King
um Yeah. How's stuff ah aside from the sleep?
01:59.18
r
ah Good. um you know trying to ah Windfall has been incredibly busy this quarter, which is good. um Usually, like i'm I'm in a function called revenue revenue operations. ah and What's interesting about it is we we have ah a fiscal year that runs February 1 to January 31.
02:19.72
r
And so ah the first month of a quarter and the last month of a quarter are incredibly busy for me. But I'm entering, I enter a lull in like the middle month, which is this month.
02:30.38
r
And so after this week, things start to settle down and I can actually, I stopped reacting and get more proactive. So I'm looking forward to it.
02:36.79
Tyler King
Yeah.
02:37.92
r
But I've, you know, if you look backwards, I've had two months of just like go, go, go.
02:42.47
Tyler King
Yeah.
02:43.80
r
So I'm ready.
02:44.06
Tyler King
I guess that's that's the price of fast growth, right?
02:44.78
r
I'm ready. I'm ready for, this is not started to last.
02:49.90
Tyler King
ah not Not calm.
02:50.20
r
Not calling. That's what I mean. It's a bit, but, but it um, but yeah, things are going well. I'm JD is doing a good job on leg up health. Um, we've, uh, you know, you'd ask for an update on lead purchasing from the last episode, uh, that, you know, as you, as ah you may recall, we, we were, um,
03:09.81
r
pretty excited about the ability to purchase ah leads from lead vendors who these with with leads who are business owners actively looking for health insurance. ah When we first turned the test on, we got like four great leads and JD was like, these are great. like If we get this continues, like this is this is a gold mine. And then no more came in for like four weeks.
03:34.26
Tyler King
Yeah, this feels solvable. Like the the the first four were so good, we would have paid twice what we were paying to get them, right?
03:42.75
r
more, I don't know about, I should, I don't want to say twice, but like, it feels like we'd paid a lot more. I'll just put it that way.
03:47.93
Tyler King
Yeah, yeah.
03:48.08
r
Like at least, at least some amount more.
03:48.45
Tyler King
and and there And there are presumably other vendors out there. So it's a bummer that things dried up, but like I've got to imagine it's worth putting a little more into trying to get get some more.
03:59.17
r
I agree. And what's interesting is, uh, you know, we talked about it on and ah Monday and our partner meeting, uh, uh, right. Like since then we've had like four or five more leads come in.
04:10.16
Tyler King
oh wow it's
04:10.27
r
Um, just because of, I have no idea why like seasonality or.
04:13.03
Tyler King
you know Yeah, we had this with, so we used to buy, we we tried this at lesson knowing serum. it It makes less sense at lesson knowing serum for just like unit economic reasons and various other things. But, uh, we were primarily buying from a company called software advice and yeah, it was super streaky like this where we'd just get hammered with leads one day and then kind of nothing for awhile. So I assume these, these lead vendors, you know, they run their own websites, you know, do SEO or PPC, whatever they're doing to get traffic. And then they.
04:43.51
Tyler King
people who hit their website, they're like, Hey, fill out this form for whatever reason. And then they sell that person's information to like a health or listening CRM. So I assume they must be getting really streaky traffic for some reason. Does that sound right to you?
04:58.52
r
Yes. and i also i think that they're probably like My guess is that what what they're bidding on for us is fairly competitive. um we're we're like There's kind of two factors, I think. One is it's a competitive search term. like There's lots of vendors trying to bid on this. um The second is we are making it Utah specific, so we're condensing the population of which they could serve ads to.
05:22.08
Tyler King
Hmm.
05:22.25
r
and then um I also, and so I think like what's happening is that there's probably was a surge of people searching, um, in December, uh, because it's now getting like urgent.
05:31.52
Tyler King
Mm-hmm.
05:33.65
r
Um, and people are, uh, you know, eating through the competitive budgets and then finally we're getting to the top. That's, that's my guess.
05:41.06
Tyler King
Gotcha, yeah.
05:41.11
r
Uh, cause, cause this happened without JD saying a word to them. Um, but, but, uh, hypothetically, like if we could. if If they're doing this and making money, we should be able to also do this locally and probably do it um spend spend more money you know and and get more leads.
05:57.50
Tyler King
Yeah. Yeah. Yeah. You mentioned that last time that it that's, yeah, I don't think we slash you have the bandwidth for that right now, but yeah, that's a cool long-term thing.
05:59.01
r
so
06:07.30
r
Yeah, that's that's optimization, right? like we are One of my favorite things that I've learned at Windfall is one of our core values of leverage over optimization. The leverage, in this case, is ah figuring out a a repeatable lead source. ah The long-term optimization is saving some money on it by bringing it in-house.
06:25.95
Tyler King
Yeah. Yeah, that makes sense. It's it's like the the big company version of this is whenever like a giant company like Apple says, well, we're going to start manufacturing our own processors or whatever. And it's like, yeah, you reach a certain scale and you should probably own every single part of the supply chain, but probably doesn't make sense for a small company.
06:41.44
r
Got it.
06:44.01
r
Exactly, exactly.
06:45.21
Tyler King
Yeah.
06:45.71
r
so um That's my lead purchasing update.
06:46.60
Tyler King
Cool.
06:47.65
r
um you know I guess ah you should hold me accountable to this, but like one thing I could do to help JD is just research other lead purchasing vendors and try to get more leads to him.
06:58.23
r
We we had this conversation ah last night i'm on the way to the ah while I was on the way to the airport, um and I was just like, hey like um What's going on with this lead?
07:09.16
r
like How many leads do you think you can handle a day? Because we one thing we we talk about is we know that if we do outbound, we get leads good things happen. like we We generate opportunities, revenue goes up.
07:22.61
Tyler King
yeah yeah
07:23.01
r
And it goes up like significantly, not like insignificantly. Um, but when he's like, he's the only guy right now, he's the only person. And so he's, uh, his ability to to put the like outbounds of volume game.
07:36.39
r
So his ability to like put his head down and do the volume necessary to get to the wind is limited. Um, and so it's like, that's where lead purchasing becomes such a high signal. Uh, thing where if we could get him, I was like, how many leads do you think you actually need to be able to do to replicate what outbound is doing?
07:46.78
Tyler King
Yeah, yeah.
07:53.00
Tyler King
Mm hmm.
07:53.12
r
And he's, and and he thinks it's like, well like 10 to 20 leads.
07:57.56
Tyler King
per Per a month.
07:57.55
r
10 to 20 quality leads a month. Yeah.
08:00.87
Tyler King
Yeah. Yeah. I mean, that makes sense because, yeah, if you close one employer client a month, that's not bad.
08:06.39
r
We double the business.
08:07.42
Tyler King
Yeah.
08:07.69
r
ah
08:09.85
Tyler King
This actually ties into something I've been thinking about with listening to him a lot is, I don't know, like we all have our kind of grass is always greener thing where you look at other people and you're like, Oh, they're so good at that. Or you look at other businesses and you're like that, that specific thing comes so easily, so easily to them. One thing I often find myself kind of jealous of other people about is the ability to hire.
08:30.85
Tyler King
uh non full-time w2 employees like i'm gonna hire a little freelancer for this project or a contractor to do this or that and they kind of they they're able to keep their teams really small and just do this like outsourcing or part-time work or whatever to to fill in the gaps that they need when they need them and i've never had I'll admit I haven't tried that much, but I've never had any success. But anyway, I think ah a thing that I didn't realize until a little more recently is a different way to do it is rather than saying I'm going to hire a person to do this because like Rick, and you've said before kind of brought up at some point, we're going to need to hire another JD or an assistant to JD or something like that. A different version of this is you
09:13.24
Tyler King
Like there's kind of a spectrum of hiring people. Like on on one end of the spectrum is W2 full-time employee. On the other, in the middle I'd say is like a contractor or freelancer. On the other side is like a company that is selling you a product or service.
09:27.95
Tyler King
that by no definition is an employee of yours. And so for example, at Lessening CRM, we work with Conversion Factory for marketing now. So we only have one marketing person, but she kind of manages Conversion Factory, which is like an agency of a handful of experts in different areas. And so we kind of get we get that extra labor. Anyway, I'm taking a long time getting here, but my point is maybe hiring another person isn't the solution.
09:56.77
Tyler King
It's outsourcing it by making it so JD doesn't have to do any of the outbound at all anymore.
10:01.84
r
I think you're right. ah The more I think about it, you're absolutely right. um The one thing we don't want to outsource is the service component. I'm i'm pretty convinced about that. um I could be unconvinced, but yeah.
10:13.21
Tyler King
No, no, i I fully agree with that.
10:15.06
r
yeah but um so like so like If we're going to bring someone like on to payroll, like under the leg up health, let's just call it ah sort of W2 or direct contracting um approach, which is more on like the first side of your scale, it's going to be customer service related.
10:35.54
r
it's going to be like Or it's going to be converting leads that are coming in. It's not going to be doing outbound first.
10:40.49
Tyler King
Mm hmm.
10:41.81
r
um So then it goes, okay, well, um that doesn't help really JD right now. So what that could do is like, okay, we do that. Now JD can do more outbound, which is, which is good.
10:53.13
r
Um, but he's, you you know, when you hire someone, what happens? You got to train him. So the reality is you hire someone JD needs more leads, not less, uh, not, not fewer, uh, you know, uh, for the, for some period of time while he's ramping the person.
10:57.39
Tyler King
yeah Yeah, yeah, that's true.
11:08.84
r
Um, and this, you know, you know, there's no guarantee you get the right hire the first time. So you could be, you know, cycling, for a little but little bit there into until you know it down. So um yeah, I think I agree. Like I think um i think there there's,
11:22.60
r
it's interesting. Like one pocket is just like inbound lead generation, which lead purchasing would fall under and and ja ja like you could hire someone to to manage that. right? Like on a contractor basis.
11:33.97
r
um There's also, you know, the concept of out ah outsourced SDRs or um like there's people out there who do outsourced SDRs. I worry about that a little bit in terms of ah brand um representation.
11:49.68
r
Because I think a lot of what JD does so well on on the phones is like, hey, like we're not actually trying to sell you. Whereas like, you you you pay someone for a lead, they're gonna be like,
11:56.62
Tyler King
yeah
11:59.26
r
you need to talk to JD or you're gonna die. you know like It's gonna be extreme.
12:02.80
Tyler King
let me Let me riff on that real quick. so I was listening to ah the Startups for the Rest of Us podcast with Rob Walling, and he had on, I think his name is Wes Bush. He's the author of product-led growth, the book. They were talking about product-led growth. and ah People use this term and have very different definitions of it. and so Rob asked Wes, how do you define product-led growth? And i'm I'm going to paraphrase here, but more or less what he said is, traditional growth, and let's call it, ah he didn't use this term, but I'll use the term sales-led growth. Sales-led growth is, first, you get the lead, second, you monetize the lead you sell, and third, you provide value. That's the old way. or that not People still do this, of course, but that's one way. Product-led growth basically just means you flip the last two. You get the lead, you provide value, and then you monetize.
12:52.26
Tyler King
um And I was listening to this and I was thinking about it through the lens of listening CRM thinking this really helped me get clarity on what. Like. We have a customer service team, but they talk to customers before they sign up and pay. Is that sales? And I think we've had a bit of like ah some ah indecision because like none of these people want to be salespeople and all that. and And this really helps solidify in my mind, it's not sales. your Your job isn't to monetize them. Your job is to get them value. They'll they'll be monetized later when their free trial ends. You don't have to do that part.
13:25.52
Tyler King
Anyway, I think we can connect that to what JD's role here is, is like he should be, and and why you you said you're nervous about s outsourcing SDRs. The outsourced SDRs are trying to monetize and then provide value. And that's not the model of like up health. It's let's get them value. And then the the monetization is a by-product of that, I think.
13:45.42
r
I agree. yeah that's I like that that simplification of, you know are we providing value and then monetizing later or are we just trying to monetize? ah get when we start When we start doing the latter, it it gets out ah away from our core positioning and values, um which is limiting but a good limitation, I think.
13:59.91
Tyler King
Yeah.
14:05.91
Tyler King
Yeah, it's it's such an interesting business like a health because health insurance is so commoditized. Like you're not selling your own product. You're selling these insurance products that anyone can resell. So you're selling the exact same product as someone else. The lead generation process is basically the same for everybody.
14:22.17
Tyler King
Which, in a sense, this creates a huge, I mean, you don't control pricing. So you can't compete on price. So in a sense, it's very challenging that it's such a commodity. Everyone's offering the exact same thing. But in a sense, it it feels kind of liberating because it's like JD is better at service than any of these other people are offering. So it's it's kind of like the only thing you can differentiate on, leg up health is way better at. So it seems like that should be a good thing for leg up health.
14:44.01
r
And just remembering, but but but it's easy to it's it's easy to forget that and make a decision, try to do a shortcut and then get back into the rest of you know being just another sales insurance agent.
14:48.55
Tyler King
Yeah, yeah.
14:55.18
Tyler King
Yeah. So anyway, I really liked the idea of like, rather than thinking, how do we scale JD thinking, how do we narrow his role to the part that he's really differentiated at?
14:56.61
r
um
15:05.07
Tyler King
And everything else is just like a service that we buy from someone else.
15:08.75
r
I love this. um We should talk more about this before, you know, we we set budget for next year because it's like, we we've all yeah one of the things we struggle with, ah you know, we and this case translates into my last topic and then I'd love to just spend the rest of the time talking about less knowing CRM.
15:14.71
Tyler King
Yeah.
15:25.53
r
One of the challenges I think any bootstrapper faces um is how do you grow ah Uh, like step function headcount, um, ahead, you know, what within the constraints of budget, um, while also taking care of your people that you have today.
15:35.95
Tyler King
Mhm.
15:42.81
r
So for example, JD is really close to being, you know, exceeding his target comp and, and like us having some extra money. ah to spend, it's likely that we'll be in that position ah February 1st as we move into the next year's budget.
15:55.47
r
But then you're like, okay, ah how do how do we hire another person? It's like, well, that's a you know multiple of what our free cash flow is. so um So I'm starting to think about like, okay, does that mean that we just need to be patient until we can hire someone?
16:03.73
Tyler King
Yeah.
16:09.94
r
Does it mean we need to set start saving money so that we have ah a bank account of cash with at least 12 months of runway we can guarantee someone if we hire them.
16:20.37
r
Do we try to hire someone for you know flat out cheap and say, hey, you know you're in this with us, you're another partner? like ah do Or or or do do we try to do I put money in the company to to fund ahead of this?
16:26.03
Tyler King
Mhm.
16:31.04
r
Do do we raise ah ah equity, which I'm pretty opposed to? Do we raise debt? um And so i'm I'm starting to think about like how do we finance Um, the next phase of growth, is it, you know, bootstrapping, um, is it, uh, or is it aided by some third party factor?
16:44.59
Tyler King
Mhm.
16:48.00
r
And then with that, within each of those, like there's a question of like, what's the order of, uh, expending, uh, uh, things.
16:55.79
Tyler King
Yeah.
16:56.37
r
So.
16:57.74
Tyler King
Yeah, you said like, I think leg up health is arguably already past this point, but like the first couple people don't necessarily have this problem. Like, like a lesson knowing like, okay, it's me and a co-founder, my brother.
17:09.53
Tyler King
We both were like, he's very clear with co-founders. Like you just don't, you don't get paid yet. Um, that's easy. But then we brought on, uh, four partners early on who were kind of, you could think of them as late stage co-founders in some ways where it's, it's like you get paid way under your market rate, but you have a lot of extra upside.
17:26.87
Tyler King
Um,
17:29.42
Tyler King
That's what I am right now. And that's what JD is, right? like You're the only true founder of the business. But JD, this is his primary source of income that he was making less than he would somewhere else for quite a while. And now he's hitting kind of his market rate. And then the hope is in the future, there's that upside. In my case, I'm just like,
17:47.70
Tyler King
I'm not doing much work so it's not a big deal.
17:48.96
r
You got 50 bucks. You got 50 bucks.
17:50.38
Tyler King
Yeah, 50 bucks this year.
17:51.01
r
Come on.
17:53.06
Tyler King
I'm raking it in. um But yeah, i'm just i might my hope is that like I'll continue putting in relatively little effort and 10 years from now it'll you know pay me money. I i don't know that... like it feel You hit a point where you can't do that anymore, I feel like.
18:08.34
Tyler King
Although, I don't know.
18:08.31
r
not not an not a
18:08.91
Tyler King
like
18:09.92
r
not in you know That's what multi-level marketing is, I think.
18:12.69
Tyler King
Yeah, that's, that's a good point. Well, or that, that is how like venture back startups grow. They do pay people, but they continue motivating people with equity for a long, long time, you know, into hundreds or even thousands of employees. Well, they do it forever, but I'd say employee number 100 at open AI is like, I don't give a fuck what my salary is. Like it's all about the the equity. Um, does that work at a bootstrapped company? Does it make sense? I question that.
18:40.99
r
Yep. Yep. ah So, yeah, I mean that's, but that's the dilemma. ah I, I'm worried about this. So what what what I did was I reached out to our mutual friend Chase and I was like, Hey, I don't understand debt.
18:55.44
r
um Is this an option for me? And I gave him the numbers and he said, you're early. um And then I was just like, I hear about all these business owners who have capital intensive businesses, they raise debt to get off the ground, right? like they And he was like, well, well yes, but um they have a business that has like you know inventory and um collateral that that you can you know raise debt against. I'm like, oh, okay, I see. um But still, they had no revenue when they started and and they they needed capital. I'm like, so so help me understand this. And he goes, well, at the end of the day, if you can if you have a strong personal credit,
19:35.91
r
And you can personally guarantee a a business loan. um And it's, you know, within certain parameters, it gets it's doable at any stage, as long as you have a plan and and some sort of historical, you know, support of that. um And so i I got to a place where it's like, I probably could raise some debt. He's going to introduce me to someone.
19:55.95
r
Um, and we could raise like anywhere between anything, I think it's under $200,000, uh, is like, uh, what's called an S B a small business, uh, uh, something alone.
20:07.36
Tyler King
Like a lions or something.
20:08.30
r
Uh, yeah, it's like, uh, yeah, I don't know what SBA stands for small business, something.
20:08.52
Tyler King
Yeah.
20:13.31
r
And it's like basically a, a, a backed loan that is 75% government guaranteed. And if it's under if that type of loan is under $200,000, apparently it's it's an express approval process. um So we could go raise $150,000 or $100,000. 75% of it is guaranteed by the government. i I would have to personally guarantee probably most likely at our state of business. that's That's one way to hire ahead.
20:36.71
r
of growth. um What I think what what what what Chase's advice was is like equities for ah for like, this sounds more like an equity raise is what he said.
20:45.50
Tyler King
Yeah, yeah I was gonna say that
20:46.20
r
You know, yeah yeah like equities more for like ah experimentation, um debts more for scaling what's working. And so he kind of cautioned me a little bit of you're probably too early to try to raise debt for this purpose unless you have a lot of conviction.
21:00.80
Tyler King
Yeah. Cause you have to pay the debt back. So you can't risk hiring someone that doesn't work out.
21:02.96
r
Yes.
21:06.22
Tyler King
And then it's like, okay, like that could crush the whole business. Whereas with equity, and I'm very and opposed to raising equity, but, uh, equity capital, but like you can. Fail.
21:16.72
Tyler King
And then you're just like, well, when we eventually succeed later, these shareholders are going to get their money.
21:22.07
r
Yep.
21:23.18
Tyler King
um Yeah, I have two experiences just to to add onto what you said. so like one A friend of mine was starting a brewery that never ended up taking off for other reasons, but he was able to raise, I think, over a million dollars of debt. and it's It's for exactly the reason you said. He's like, well, what are you going to spend the million dollars on? I'm going to build a building and I'm going to buy a bunch of vats or whatever you use to brew beer. and it's like if the If the business fails, like all of that is still worth $800,000 or something. so It's a relatively low risk for the bank.
21:52.75
Tyler King
When we were earlier, we were trying, less knowing serum. We were trying to get a line of credit, which is barely even debt. Cause with the line of credit, you pay it off almost immediately. It's, it's, it's not meant to be like long-term debt. So it's, it's not nearly as risky for the bank, I think, but even then they were like, I was talking to the bank and they were like,
22:08.84
Tyler King
Okay. So like, what assets do you have? And I was like, what do you mean? We don't have, we're a software company. And they're like, well, surely you have like desks and monitors. And I was like, you're going to base the value of this loan off of the price of our desks. And they're like, yup. That because if you fail, we're going to come and take all your desks. And I was like, well, we have like $2,000 worth of desks maybe. And they're like, yeah, this is, this isn't happening.
22:32.23
r
did you um Did you ever personally guarantee any any credit at the early days of less annoying CRM?
22:38.12
Tyler King
Yes, i don't so we're so old. Things like Stripe and Mercury did not exist back then. There are much more startup-friendly banking services now. ah But in 2010, if you wanted a credit card for your business, you were going to like Chase or Bank of America. And they yeah they were basically like, yes, we need a personal guarantee. It was only on the credit card itself. I never got like a loan. We didn't end up getting the line of credit. I think we could have, but we were like,
23:07.45
Tyler King
10 hours into paperwork and we're just like, we don't actually need this. So this is a waste of time. Um, so it was just the credit cards that I actually personally guaranteed.
23:16.09
r
Yeah, I guess I'm taking, that's interesting. So yeah, Mercury is a, it's a blessing. it's It's a bank account that we have baking so solution. They have makes it super easy to provision credit cards.
23:26.15
Tyler King
Yeah.
23:26.25
r
Holy the cow. And you just have to maintain a, I think it's a bank balance of $20,000 or more and they, they give you credit. Um, just, just, you know, for that, um, which is great.
23:32.95
Tyler King
yeah
23:36.00
r
Um, and then, uh, uh, quick books, um, which is interesting. ah sees our financials and they're they're they're starting to market to me that I'm pre-approved for 20K.
23:47.97
r
So i'm just I'm starting to realize that there's probably like like I was having a a very like high level conversation with Chase, but there's probably $20,000 we could go get right now from our existing vendors because they've seen our cashflow.
24:05.82
r
But like is that worth it?
24:07.33
Tyler King
Yeah, so the the similar the parallel to this that I've looked at before is Stripe Capital, which has probably changed.
24:07.70
r
I don't know.
24:13.10
Tyler King
But like when it first came out, it makes sense. like The idea of all our revenue is processing through Stripe. They know what our cash flow well they don't know what our outgoing cash looks like, but they know what our incoming cash looks like.
24:23.99
Tyler King
and they So they Stripe Capital is basically like, you get a loan for whatever amount. And they literally just pay themselves. like You don't pay them back. You just get less from your credit card processing, if that makes sense.
24:35.41
Tyler King
um And yeah, it it sounded interesting cause it's literally like press this button and we'll wire $60,000 in your account right now. And I kept being like, well, that sounds cool.
24:46.84
Tyler King
A with stripes specifically when I did the math on what the effect, they like are very sketchy about how they describe interest rate. They're like, we're going to take this percent of your payments until this it's very hard to figure out what the actual interest rate calculation is.
24:59.39
Tyler King
When you do the math, you're like, that is a very high interest rate. But secondly, Oh no, like 20, probably.
25:02.36
r
Like what, 10%?
25:06.60
r
Okay.
25:07.64
Tyler King
the the
25:07.59
r
Yeah. the The rates I'm looking at are 10%.
25:09.62
Tyler King
Okay. But even setting that aside, they kind of, the way it worked is like they would get paid back in like eight months or something. And it's like, what is the point of a loan?
25:15.80
r
Wow.
25:18.02
Tyler King
You, you have to have a real cash generating machine where it's like you pour cash at the top and you get it immediately at the bottom for that to make sense. I could never figure out a thing where it would make sense to do that.
25:25.58
r
Yeah.
25:28.04
r
Yeah, the the the loans that I've looked at are 10-year terms. So um there it's it's it's a long horizon, um it's but it's you know a lot of interest over the over the course of that term.
25:36.88
Tyler King
Yeah. Yeah. and And then it's like, okay, well, what do you do with 20 K? Like it's just not enough, you know?
25:43.62
r
Is it? it's one I mean, it could it could be the difference between hiring someone in July versus December for our business, and customer service person.
25:51.21
Tyler King
Yeah, it could be, it could be. I I'm very open. I mean, first of all, obviously it's not my decision. It's yours, but like, I guess my question, this is my attitude towards entrepreneurship is like, then just wait till December.
25:56.13
r
Yeah.
26:02.60
r
that That's what I always come back to is like time, like we always have time and we can always wait. Um, I think the only risk that that we run is, is JD going to burn out. And I think that should be the only reason that we like, that should be the primary reason where we go. Uh, like we can't wait. Um, is, is JD going, I, this is too hard.
26:23.77
Tyler King
i Yes, I think that's a good thing to consider, but i'm gonna I think this might be a weakness of yours, Rick, which is your when when things are tough, your attitude is go faster. and I think if burnout is the concern, going faster is not the solution. Going slower is the solution to burnout.
26:44.79
r
No, that's fair. Yeah. What you're saying is that that that there are multiple options in that situation that include what you could, you know, hire help, or you could also just decide to do less or different do things differently or take the pressure off, whatever it is.
26:58.59
r
There's lots of options in this situation.
26:58.73
Tyler King
Yeah, yeah.
27:00.07
r
i my My default is hire people. Let's let's go let's let's double the business.
27:04.61
Tyler King
yeah And now JD has two jobs instead of one. Now, ah it's a different story.
27:06.81
r
yeah
27:08.35
Tyler King
If you're not making enough money, totally different story. like I think prior to basically right now, this moment, JD was making an amount of money where he's able to survive, but it's not sustainable.
27:19.73
Tyler King
like His income could be a cause of burnout. like I'm working so hard and I'm not i'm not saving for retirement. i I'm having trouble supporting my family. In that situation, you have to move faster to get to the point where you're making enough money.
27:32.21
Tyler King
Once you're making enough money, now you have the option of saying, okay, maybe the next year we'll grow 50% instead of a hundred percent, but I'm just going to kind of have a good time doing it. That's an option.
27:42.45
r
This is the major difference between like the term Ramen profitable and default alive. I feel like um yeah what you're describing is a default alive situation and that changes everything.
27:46.86
Tyler King
Yeah. Yeah.
27:52.05
Tyler King
yeah Um, I I'm, oh yeah.
27:54.07
r
Tell me about you, man. that this
27:55.87
Tyler King
Yeah.
27:56.86
r
yeah but Let's move off this.
27:57.06
Tyler King
Sorry. What?
27:57.98
r
like I was just going to say, like yeah this is tell me about what's going on in your world.
27:58.49
Tyler King
okay sure
28:01.67
r
I appreciated this. this was um I've been thinking a lot about the whole ah like what's next for leg up and what you're telling me is like slow down, man. if any Work on lead purchasing and you know if that work like that's what you can do to help JD right now and then like we'll figure it out.
28:17.71
Tyler King
Okay, sure.
28:17.74
r
like but don't have it There's not a lot of urgency here.
28:18.25
Tyler King
i I'm open to talking about the the fast path. I'm just making sure you keep in mind the other option, but yeah.
28:24.59
r
Okay, cool.
28:25.38
Tyler King
ah ah Yeah, for my stuff, I don't have a...
28:26.83
r
Tell me what's new with you. Thanks for letting me dominate the first half hour of this podcast. I was, it was great.
28:32.43
Tyler King
Absolutely, I thought that was good stuff. um Yeah, I honestly don't have a ton of, I think, interesting stuff. I'll give a forms update just on like trying to get people to use our form builder. um So last week was Thanksgiving.
28:44.41
Tyler King
it's so One of the problems with anything that's kind of metrics driven is any holiday just
28:45.69
r
um
28:50.48
Tyler King
destroys your metrics. Or at least for ah for a B2B type thing, like businesses aren't working. So no one's buying a CRM. No one's using a CRM. Even like Labor Day or something where it's a single day. And honestly, I don't think that many people even care about it. Still, the metrics drop. And for the next month, you look back at your how many people are on free trials. And it's like, oh, we have 50 fewer people than we should have right now because no one signed up for a free trial on Labor Day.
29:15.44
Tyler King
um So having said that, our metrics are down, but not not in a way that concerns me. um The big win we've had, I think I've shared that there's there's a bunch of different things to look at with with forms to see how how do we measure if we're getting people actually using them. The main metric we're looking at is the total number of submissions we're getting per month or per week or whatever.
29:36.21
Tyler King
But to me, kind of the upstream of that is how many active form users do we have? And I'm defining active as getting at least four or more submissions over the course of seven days. um To me, that means like you've you've actually done something with forms.
29:52.59
Tyler King
Last time we talked, I think I said we were kind of having a drought with that. Like we still had, we were, our form submissions were increasing, but it was all coming from people who activated like a month or two ago.
30:03.77
Tyler King
Um, we did have six new active users in the second half of November, which I'm pretty excited about. And to to put this in perspective, we have 10 current active users and 10 people have gotten four or more submissions in the last week.
30:16.46
Tyler King
So like more than half of them came on very recently.
30:16.44
r
Woo hoo.
30:20.15
Tyler King
Um, no, no, that's the problem.
30:20.30
r
And did you do anything differently to get those six or, uh, yeah.
30:23.08
Tyler King
No, it does go onto the, just like the emotion, you know, people talk about how much a startup is an emotional roller coaster.
30:23.68
r
Yeah. Okay.
30:31.53
Tyler King
We can have a bad week and it's easy to beat yourself up and be like, Oh, we need to change things. We need to do something different. And then we have a good week and we're like, Oh, it's working. We just have to keep doing this. And the reality is neither is correct. It's probably in between the two, right?
30:44.59
r
Yeah, your your version of lead purchasing now is form submissions, active form users.
30:48.55
Tyler King
Yeah, yeah, exactly. um Now, I said we haven't done anything yet. we we are It's not because we're not doing anything. It's because the next step required a little dev work. And there's kind of two next pieces. ah One is we're making it. You've kind of been encouraging me the last couple episodes, like kind of let loose a little more, like stop the beta period and just ship it. And my my argument against you was, it it wasn't an argument against you, but my defense of what we were doing was,
31:17.26
Tyler King
We want to be able to talk to people, the the bait the whales, the people are going to get a lot of submissions. We want to offer, like we'll port your forms over from your existing form tool. We'll we'll show you how it works. And by making it totally self-serve, we risk that. Anyway, so I think we found an okay middle ground here where it's a new pattern. We've never done this before. What we're going to do is require users to turn on the feature.
31:40.07
Tyler King
um So normally, the way it works is like you go to the pipeline settings and you make a pipeline. like There's no concept of like pipelines being on or off. You just go there and you use it, which kind of it's good from a low friction standpoint, but it doesn't give us that moment to kind of grab their attention and be like, hey,
31:57.69
Tyler King
We're here. Um, so we're doing with the form builder. One thing is we're going to start advertising, pushing it more in other parts of the app, like little graphics being like, Hey, you could use a form for this. But then once they get to the form builder settings page, instead of being like opt into the beta, we're going to be like, do you want to turn this on?
32:14.13
Tyler King
And if so, do you want to turn it on for self-serve? Do you want to schedule a call with us or do you want us to port your form over? How do you want to get started here? So we haven't shipped that yet.
32:23.38
r
I love it.
32:23.79
Tyler King
It takes some dev work, but that's what we're going to try.
32:26.07
r
I love it. And you can also, I feel like it just, like it is your your conversion moment, right? and Like the first part of it and you can market that.
32:31.13
Tyler King
Mm hmm.
32:33.71
r
So I think that's cool.
32:34.69
Tyler King
Say more about how we can market that.
32:35.28
r
um ah There's a new feature for you to turn on.
32:40.05
Tyler King
Oh, yeah, like send it to cu like, like send a newsletter out and say, yeah, yeah, that's that's a good point.
32:42.50
r
Yeah. Yeah.
32:45.32
Tyler King
It also like.
32:45.39
r
um, versus like, check out this new page. Like it's, it is, it's a bigger thing to like, would you, have you, you haven't, turned we've noticed you haven't turned on, um, our newest feature.
32:53.93
Tyler King
Hmm.
32:55.09
r
Why, why haven't you turned it on?
32:57.30
Tyler King
Yeah, that's a good point. I think that's like a trap that a lot of entrepreneurs fall into. And I did in the past, but I think i'm I'm better about this now is like, it's so tempting to, to spend a lot of time, like metrics, everything, and people might be like, anytime I'm talking to other founders, they're like, well, how many people use this feature? How many people use that feature? And I'm like, I don't know. And it would take a lot of effort for me to get the answer to that.
33:18.75
Tyler King
It does also make it much easier to track that, though, to be like literally they have to push a button and that has to save a thing in a database to turn the feature on. So it's very easy to be like who has turned the feature on.
33:29.55
r
Yep. That's great.
33:30.42
Tyler King
Much harder to say who's using pipelines. like that That's a more complicated question to answer.
33:33.35
r
Yeah. First you got to define what that means.
33:34.46
Tyler King
and Yeah.
33:35.56
r
yeah
33:36.89
Tyler King
um So I think that's probably all I've got to say about forms.
33:38.16
r
Are you bullish on this still?
33:42.08
Tyler King
but i
33:42.73
r
Like what's your, what's your mood on this?
33:45.21
Tyler King
Oh yeah. Yeah. Sorry. I had one other thing I want to say, which is basically that I'm in the middle. It's, it's definitely a slog. It's not like it's, it's, I remember the early days of less knowing CRM, I built this like custom analytics tool that it was like a live before analytics tools were like live updating. It was like, it would show me every user who's logged in most recently and like where they are in the app. Maybe this is like invasive and we shouldn't have done this, but like,
34:12.24
Tyler King
you Every time someone loaded a page, it would like update this and I'd see it and I had it open on my screen and I'd be like, hell yeah. And I remember that feeling of just like one single person loading one single page felt good. I'm past that now. like With actual less knowing CRM, our report shows 250 users at a time sorted by their most recent usage. All 250 are from the last minute. So it's like,
34:39.03
Tyler King
There's just like overwhelming usage. And this is nothing compared to a actually big company, but I'm used to. I can log in at 2 AM and 250 people in Australia have loaded the site in the last minute. It is so hard to go back from that to go to, like here, let me tell you right now at 9.40 central time, we've had six form submissions today.
35:05.25
Tyler King
That's not six people making forms. That's not six people using forms. That's they sent the forms out and six people have filled out their forms. It's tough going back to these really small numbers.
35:15.02
r
I can relate to this. ah that i mean Leg Up Health is not too different from the business we built at Zane Benefits and PeopleKeep.
35:23.70
Tyler King
Mm hmm.
35:24.04
r
And i I did what you're doing. You did a lesson on CRM with Zane Benefits. like It was like, oh, we've got a lead. Oh, we've got two leads. And then eventually you're like, we have too many leads. And we need to die and and and like it's very hard to do the same thing over again.
35:38.34
r
and and like have the patients and we're not even the patients just like have the adrenaline hits of like that matter.
35:43.78
Tyler King
Mm hmm.
35:44.82
r
Like there's milestones mattering again.
35:46.56
Tyler King
Yeah, it doesn't make you feel good the way it yeah I mean, it still feels good, but it's like I I need more to make my my brain get excited about this.
35:54.59
r
Yeah. Yeah. Yeah. That's funny. um
35:58.26
Tyler King
This is all.
35:58.19
r
I wonder if, I'm curious, like, would it be different if, if you, if you went like, if this was a new business and it wasn't related to less knowing CRM at all, would you be able to get the adrenaline hit or are you just like over this early stage for you?
35:59.64
Tyler King
Yeah.
36:09.58
Tyler King
Yeah, well, great point. I don't know. I'll say I like it with like a health, but that's, I'm also not the one doing all the work. I'm sitting in the Slack channel. JD's like, I just got one more consumer client, which like an individual health insurance policy. And I'm like, great. Cause I didn't have anything to do with it, but it it'd be hard to spend all day. Just spend a week working and get one of those.
36:30.28
Tyler King
This is why you know it's so common. Everyone assumes the goal of a startup is to exit, right? And one of like of the reasons I wanted to call this, I think we both wanted to call this startup to last, but one of the reasons for me why I like the name of this podcast, I don't want to exit because I don't want to do that shit again.
36:46.46
Tyler King
like i It was so much fun at the time, and I really miss those times, but I don't think in my current age, my current energy level, and like I'm a little more jaded now, I don't think I could go back and do that again.
36:46.92
r
Yeah.
36:56.88
Tyler King
No.
37:01.27
Tyler King
And I don't want to retire.
37:01.61
r
thats Yeah.
37:02.77
Tyler King
Like if you exit, you either have to retire or you have to go do it again. And I don't want either of those options.
37:07.42
r
Well, yeah there's a middle path that you can, you can, uh, buy a business. Let's pass that stage.
37:11.85
Tyler King
and That's true. That, that would not play to my strengths at all, but you're right. Um, there are, or you could go get a job working for someone else, but, uh, I wouldn't want to do.
37:18.30
r
Yeah.
37:20.52
Tyler King
Of all of those options, starting a new business is what I would do. If less knowing serum imploded, I wake up tomorrow. I don't know what's next. I'm thinking either I got to go talk to Rick and figure out how I can become a full-time employee at leg up health, or I got to go start my own business.
37:34.07
Tyler King
Those are the two options I'd be considering.
37:36.66
r
ah So speaking of that, ah this made me think of something that I've been meaning to tell you. And I wasn't going to tell you on the podcast, but I'll tell you on the podcast now. So like yeah yesterday um during an an internal windfall meeting, we're doing an enablement and ah so we're we're doing we're basically showing how you can do something based on the the CRM a customer has.
37:57.21
r
And there is one customer that has less annoying CRM.
38:00.11
Tyler King
Really?
38:00.92
r
And the person that's presenting says, ah don't let the name fool you. It's definitely annoying.
38:09.03
Tyler King
Fuck that person Yeah, yeah
38:10.24
r
Well, I just, I explained to everyone very kindly that one, I would give you crap about this. And two, that um Windfall's ideal customer versus ah does not have an overlap with less knowing CRM's ideal customer. and And so it's very strange that we have a customer in in common.
38:27.41
Tyler King
Right, who who is that person that wants a almost borderline worthless CRM with this like really sophisticated data tool on top of it? That's weird.
38:36.01
r
Exactly. Well, hey, maybe maybe we should, maybe maybe there's an opportunity for you here.
38:39.90
Tyler King
Yeah, yeah, synergy. um ah Where were we?
38:41.94
r
yeah
38:46.56
Tyler King
um Anyway, yeah, to back up a little, that's very funny though. You asked like, yeah how is it feeling? How am I feeling about forms? Yeah, I'm in the middle. It's definitely going up. um The goals I set for myself are I want 1,500 form submissions per month by April 1, 5,000 by July 1, and 25,000 by the end of the year. I feel very confident about the 1,500 because like all we have to do is just turn like push this out to all our users. We've got a lot of a lot more people will use it than are currently using it. That'll get us to 1,500, no problem, I think.
39:21.31
Tyler King
um But the thing that's but harder than I wanted it to be, I just wanted some people to come in and be like, yup, I'm getting 500 submissions a month. Nope. Like I already had a form. I just switched it out with your form. I'm getting 500 a month. Boom. Instead, it's like people are getting one a day, two a day, even two a day would be like, put them as our most active user.
39:44.47
Tyler King
and And then they drop off, for and then you find out, oh, they went to a conference, and they were using it at the conference, and they got a few. But then they're not going to go to another conference. for It's just like so like our customers have such a low volume. they don't They don't really have websites. They don't have this web presence. And so it's it's just more of a slog than I was hoping for.
40:03.31
r
Yeah, it makes sense. um At what point do you just let this run for a little bit and go work on something else?
40:07.87
Tyler King
Great question. so um Let me start with the high level, but then like the devil's in the details. Our approach that we've been planning for a while now, this is not a new idea, is we need to get it good enough that like people aren't not using it because it's it's like the product's not good enough. Obviously, there are going to be some people. There are going to be power users that we don't have all the features they need. But we need to be able to get like a significant chunk, kind of an 80-20 type of thing, where most of our customers can get their form needs handled by what we offer. We need to get it to that point.
40:40.27
Tyler King
Then the plan was stop working on it, move on, but keep keep it as our marketing focus. So like marketing in 2025, we've already kind of announced the whole company. Our marketing priority, it's not getting more customers, it's not increasing free trial, it's getting people to use our form product and getting more submissions. But the hope is we're not like working on the product during that time on the form product. The question, of course, is, like well, what is enough? like When can we actually say we've gotten far enough that we can do that?
41:09.10
Tyler King
Uh, I'm happy to go into more details, but like my very short answer to that is I think April 1st is what I'm targeting. I think we're going to keep working on it for a few more months. And then I think that'll get us where we need to be.
41:22.90
Tyler King
But that is that is one of the really hard questions. like When we started, you know I've been doing a lot of customer interviews and like onboarding calls and stuff with this with the hope of learning like what features do we need before we can say, yeah, it's it's good enough. We can move on. We're getting to that. at At first, it was like, oh, when someone submits a form, I want to add them to a group. That's like everybody was asking for that. It's like, OK, we obviously need to have that. And then it's like, oh, I need a signature field. I didn't actually realize this. Ton of people have people sign at the bottom of a form. OK, we need that.
41:50.92
Tyler King
We're getting to the point now where, yes, everybody has requests, but they're all different requests, which maybe is a sign that like we are approaching the time where it's ah it's time to move on. But it may it's so much harder prioritizing when everyone wants a totally different thing.
42:03.86
r
I mean, that's great that you're still getting that kind of feedback.
42:07.15
Tyler King
Yeah. no yeah it's Overall, it's been good. it's just everything's when you When you think about it, you you think about all the stuff going right.
42:11.57
r
Let's log.
42:15.27
Tyler King
And then when you get in it, you're like, oh, this is actually work. OK.
42:18.64
r
Well, one, one, a lot more question. Is there someone else that should be sort of champ, like kind of jockeying this, uh, versus you that might be more excited by it? feel Like, not that you're not excited about it, but like that that is like, not does it.
42:30.60
r
It's like, Oh yeah, two users. Or is it, do you know what I'm saying?
42:33.25
Tyler King
Um, hmm. So I would say like Eunice our marketing person, it's like, we're managing this together. For example, she's doing half the, actually more than half the onboarding calls, uh, and like the customer discovery calls. Um, she just happened to be out of town for two weeks. So I i did a lot over the last two weeks, but, um,
42:51.55
Tyler King
Yeah, I would say she's, I am running it from a product standpoint and she's running it from a marketing standpoint. And I do think she probably has, I don't want to give the impression.
42:56.30
r
Cool.
42:58.43
Tyler King
I don't have energy for this. I'm still like very stoked for this, but yeah, you're right. And I should have been mentioning her in this conversation as well.
43:05.40
r
Cool. All right. ah that Congrats. Listen, this is a new product. This is like legit new product feature you for you've been talking about doing something like this for years.
43:15.49
Tyler King
Yeah.
43:15.76
r
um And so this is like, it's a big deal that you've got this out. And I think you can run this play again with other features. You don't, you know, there's other, there's other features to do this with.
43:21.81
Tyler King
Yeah, I hope so. Well, let me sorry to belabor this. ah ah tod what Why are we waiting? Why are we going to stop working on the product while we market it? But not like why aren't we going to move on to like the the next feature like this would be like appointment scheduling.
43:40.01
Tyler King
And by like this, I mean where you can send a link out and kind of get that viral loop. Big question mark is will the viral loop thing work, right? We built the feature. Our customers love it. It'll be a good feature for making our CRM better.
43:51.36
Tyler King
Will it be a good feature for viral growth? Absolutely no idea. And so our plan is to not do any more of this until we at least see some traction with this. But think fingers crossed.
44:00.81
r
Makes sense.
44:03.93
Tyler King
Anyway, um, I probably need to run in about a five, 10 minutes here. Um, anything else on your mind or should I just keep rambling?
44:08.63
r
You got anything else? Yeah, keep rambling. we got what's your What's your next most interesting, biggest, urgent topic?
44:17.12
Tyler King
Yeah, this is what is is not urgent. this is um As you know, I probably spend too much time thinking about like the internals of the company when I should be thinking about marketing and product as my two main things. One of the problems with running a company that's 15 years old is you've just got so much legacy cultural stuff that you probably wouldn't create from scratch. but There's changes hard, even if the change is for the best. One of those things, I think I've mentioned this before, we have a company-wide weekly meeting. The whole company meets for an hour. um This is a thing everybody likes because you know we're in person. This company is small. And if we sit in a circle of couches, we talk, we laugh, we have a good time, it actually is really good for bringing people together. It's not a particularly effective meeting. And I don't think there's any way for a meeting with 20 people to be effective.
45:07.61
Tyler King
like What are you going to do? like you can You can brainstorm, but that's too many people to like. What's what's actually happening is 17 people are watching three of us brainstorm. you know It's not like 20 people can actually brainstorm effectively. I've known this for a long time. When I meet with employees one-on-one, some of them are like, hey, the weekly meeting, kind of it's fun, but it's worthless. Why are we doing this? And then the other 75% of people are like, this is my favorite time all week. I would be devastated if we lost it. And that's like a pretty tough place to be.
45:34.75
r
Yeah.
45:36.34
Tyler King
Um, anyway, yeah, we're playing around with it.
45:36.51
r
So what's the solution?
45:39.20
Tyler King
So at first, what I was saying is let's make this more effective. Cause like literally the first half of it is Rosen Thorne. It's people just giving updates on their lives. It's like, got nothing to do with work. And it's like, well, let's, let's cut that out then.
45:49.80
Tyler King
But I say that, and then the 75% of people who like it are like, no, that's my favorite part. Like I, I, I love that part. Um, so I've kind of, I think I've accepted it's not going to be a good meeting.
46:00.97
Tyler King
And I can't get rid of it. um But this this is going to be so simple and basic. The thing we're going to try is just doing less of it. um either Either biweekly or make it 30 minutes instead of an hour.
46:09.48
r
biweekly.
46:12.99
Tyler King
I think biweekly is more promising, personally. But it occurred to me, 20 people in an hour-long meeting, even just going biweekly, that's a full-time person's worth of work. That's 40 hours. That's a full-time week of work per month that we're going to save if we go biweekly. That's fucking crazy.
46:32.07
r
You could do the rose and thorn thing like over a team lunch like that. Maybe that's a different thing altogether.
46:37.11
Tyler King
Yeah, agreed. we Yes, we thought about that as well. Maybe I should push for that. The thing is, if I'm being honest, I think the Rosenthorn is the best part of it. like not Everyone who's ever sat in a 20 person meeting knows it is a complete waste of time.
46:48.24
r
Yeah.
46:51.95
Tyler King
So if you're going to do it, sorry, if it's a present, if it's a presentation, absolutely.
46:52.24
r
Well, you didn't talk to it. Like it's not a meeting. It's more of a present. Yeah.
46:57.79
Tyler King
But then it's like, well, someone has to prepare for that. That's who's, who's doing that.
47:00.63
r
Yep.
47:01.34
Tyler King
Am I spending six hours getting ready to present to everybody for an hour? Anyway, yeah. So part of me is like the Rosenthorn is the part I want to save if anything.
47:11.04
r
yeah you know There's very little preparation. Everyone does their little preparation. there's It's a notice on anyone. and um It fills time.
47:16.89
Tyler King
Yeah.
47:18.09
r
um
47:18.48
Tyler King
And it legitimately is like 20 people going in a circle. Most people just have random updates. It's not a big deal. But probably three or four people in a given week are saying something that causes the whole room to erupt in laughter or you know a sweet story about what like it really is a fantastic kind of company bonding thing.
47:35.87
Tyler King
Do we need that every single week? Probably not. But it is it there there is value to it.
47:38.63
r
ah Yep. ah Well, a a couple of other ideas just throughout while we're on the topic. but like I'm a big fan of biweekly on these. I think ah weekly is a lot, particularly as it moves to more of a presentation that people have to prepare for and away from ah conversation.
47:49.11
Tyler King
hu Yeah.
47:55.01
r
um I think you can like have conversation as part of it. You just got to manage it, right? like And it becomes, otherwise it becomes like people are like, oh man, I'd rather go get work done. um the but the ah In terms of like being like helping with the preparation, when it becomes as it becomes more of a presentation of lot fewer people talking, ah more content for them to prepare, is you can kind of create ah rituals, like your Rosenthorne ritual, but like have little presentation rituals where maybe you're doing a department spotlight every every two weeks.
48:24.55
Tyler King
Hmm.
48:25.24
r
or um ah you know there's a You have a regular sort of CEO update at the end every two weeks. it's just And you break it into like these many things that are just ritualized and ah some of them rotate across people and departments over ah you know eight weeks. um And you know then you've got you know some standard things in there that just get you kind of updated.
48:47.39
Tyler King
So let me ask your opinion on this because so I currently send out a weekly newsletter to the company, which is where I share more of that type of stuff. Do you think there's a good argument for doing that live versus asynchronously?
49:00.72
r
Oh, yeah. I mean, i think I think some people don't read the email. um Most people probably do.
49:04.64
Tyler King
Well, OK, let's let's assume we have a culture where people do.
49:05.84
r
yeah ah Yeah. Yeah. Yeah. So, I mean, like I think, I think, ah it ri I mean, we've talked about this before, but like the the as the as a company grows, the CEO's job becomes ah much more of like, ah say less more often.
49:21.42
r
um And so, ah you know to the extent that you're reinforcing important messages and and like sort of taking a ah narrative and putting it on one slide and saying, here are the here are the five things that are going well. Here are the five things that aren't going well. I hear my observations um and and synthesizing that re and reinforcing it. like I think that's a good thing.
49:41.02
Tyler King
But couldn't that be a loom video? for Like, why does everyone have to watch this at the same? To me, if something's synchronous, if it's live, that implies there should be like interaction. If there's no interaction, what are we getting out of the live?
49:51.25
r
yeah Yeah, there should be, there could be, there could be questions, uh, clarifying questions, uh, uh, that sort of thing.
49:54.12
Tyler King
and
49:57.14
r
But, um, you know, I think that's how it depends on how you want to run it. Um, but yeah, to your point, it could be async.
50:01.41
Tyler King
yeah
50:03.08
r
Um, I, uh, I think async leads a lot to like people reading like watching it at a different times. like what what what One thing that comes with ah synchronous is everyone watches at the same time.
50:15.95
r
they leave The meeting ends, they then have conversation about it.
50:18.78
Tyler King
yeah
50:18.89
r
um yeah know that you can't That doesn't happen with async.
50:19.27
Tyler King
yeah
50:22.41
Tyler King
I'll put some more thought into this. I think what you're saying is right. I, this isn't exactly a disagreement, but I do think like a lot of your experiences at windfall where a it's a lot bigger and like getting messages out to everyone or harder. And B you you guys are moving so much faster than we are. I don't have ah an interesting thing to say all that often, which is part of the problem.
50:41.82
r
if you're writing a weekly newsletter, don't you have something interesting interesting to say every week?
50:44.39
Tyler King
Yeah, but these are, yeah. the The weekly newsletters are like very, I'm going to opine on something. It's it's like cross-training sort of. It's like, hey, if you're a customer service person, would you like to understand the philosophical considerations behind a feature we're considering building?
50:59.34
Tyler King
um It's not like, oh, this is an important company initiative that you have to know about.
50:59.76
r
Okay.
51:03.40
r
ah Tyler's musings.
51:05.35
Tyler King
Yeah, pretty much.
51:05.63
r
It's Tyler's musings. Okay.
51:07.75
Tyler King
Yeah. I mean, sometimes there's important stuff in there, but if it's like every other week, I have to have something to say, I probably wouldn't have that.
51:13.39
r
Yep.
51:14.40
Tyler King
Anyway, I'll put some more thought into it, but that's one of the things on my mind. Um, yeah, I probably need to run here, but good talking to you.
51:18.81
r
All right. Yeah, you too. If you'd like to review past topics and show notes, visit it startup to last.com. See you next time.
51:27.29
Tyler King
Bye.