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.
00:00.00
tylerking
What up Rick.
00:00.53
Rick
Um, I feel like you Jumpst startedt that like I feel like that was early I think you went too early. Yeah, okay if if you say so ah.
00:03.68
tylerking
I went too early I think I think we got it I think the recording got it but we'll find out although so the moment we're done here I'm going to hit stop and take a uber to the Airport. So I'm and we have no time to edit this I think there we're probably not going to have the normal intro of this time and startup to last the the intro when we change things up. Yeah, um, absolutely.
00:22.31
Rick
Ah, well I like it though I like I like it when we change things up now keeps people on their toes. Ah yeah, well, um.
00:33.40
tylerking
We've been doing this for 3 years or whatever.
00:37.49
Rick
Not much. It's a second to last day of open enrollment for leg up health. So um j d is drinking from a fire hose with all the people who procrastinated to the last minute to complete their health insurance enrollment for the year um so he's busy, busy. Ah, but.
00:44.13
tylerking
Um, yeah.
00:53.35
Rick
Um, overall it's been really really a really positive openrollment.
00:56.82
tylerking
Yeah that's great to hear it. It seems crazy to me that filing taxes is the same way where it's just like everyone is filing taxes on like April fourteenth um and every accountant is filing. Everyone's taxes on April fourteenth and it's like is there really nothing. We can do. To spread this out over more than like this one day out of the year like I I proposed in like a partner meeting or whatever for like up health is there some kind of incentive that can be offered or something like hey can someone sign up for health insurance like a week early and there's just nothing that can be done.
01:30.16
Rick
I think I think there's absolutely stuff that can be done I think um, we could listen I think ah next year we'll definitely do something to incentivize ah early. Ah, not even early like not last minute renewals. It's really, it's not like you're renewing early. It's it's just that you're not waiting to last minute.
01:41.76
tylerking
Um, yeah, right.
01:47.54
Rick
And but I think we could do something like even if it's just like a hey we'll put a deposit into your health savings account. We'll give you ah a gift card to you know Amazon.
01:54.36
tylerking
But I thought the problem that you could run Into. You're not allowed to incentivize people for signing up for insurance because otherwise like insurance agents would be undercutting each other and stuff like that. So So there's a delicate balance where you want to say. This is the reward for doing it earlier but can you are you allowed to do that.
02:16.71
Rick
Um I believe as long as it's not conditioned on making us the agent. Um, so if if I think as long as it gets you know the reward is available whether they continue us as the agent or not then it's fine.
02:29.16
tylerking
But you don't want to give the I mean what would it mean to give the reward to someone if we're not the agent.
02:35.69
Rick
Um, well I think we can offer it to say hey you're if you're an existing client. Um, whether you renew with us or with someone else if you if you were new and you can prove that you renewed in the first week of open enrollment.
02:46.70
tylerking
Yeah, okay.
02:49.69
Rick
And or it's not even renewed. It's like completed your open enrollment application. Update ah then you know we'll give you $20
02:52.94
tylerking
Um, yeah.
02:59.90
tylerking
Fair enough it sure does sound bizarre to ah, give someone an Amazon gift card for switching to a different agent but okay, yeah, absolutely okay, well cool, but it was yeah well who's going to switch and then take.
03:05.73
Rick
But well, that's but that's what if you don't do that. That's when you get into the rebaating issue. But who's going to switch to another agent. We've only had one person ever switched another agent.
03:17.62
tylerking
And then take the the gift card.
03:19.45
Rick
Yeah, we all the so j d and I were talking this week and we've only had 1 person like actively fire us for another agent and it was like it keeps us up at night like it's the only person but you know what they did it. It's their spouse's best friend.
03:27.55
tylerking
M. I Assume it's like their brother in law or something.
03:38.77
Rick
Um, and so it's like why we had to do it. She like corner us you know she cornered us one night you know and sorry guys thanks for 2 years of great service.
03:43.50
tylerking
Yeah, it's like yeah, fair enough. But ah, that's a person leaving for another agent but like there's still a pretty decent amount of Churn. It sounds like during it. It's an interesting business because all the new customers come in during open enrollment. Not all but a lot do but also. That's when you lose everybody because it's you know in the sass World. You're always talking about monthly versus annual subscriptions like Health insurance is always an annual subscription and the Churn always happens during open and or almost always happens during open enrollment.
04:10.98
Rick
Yeah, yeah, and I don't know why it it doesn't make sense for that to be true. Um, because generally health insurance is driven by life events not a calendar year but it is this. You know the the reason it does happen is that prices change.
04:23.27
tylerking
Um, ah.
04:27.92
Rick
You you do budget your health care on an annual basis around your deductible and so there almost is this like like if you sign up for a year and you' already like six months in it's like well why am I going to cancel this now I've already like met some of my deductible like ah but if if you are starting a year it's like and do I want to pay this or do I want to like.
04:39.94
tylerking
Are.
04:46.11
Rick
Yeah, roll the dice and see if I don't get sick.
04:48.29
tylerking
Yeah, also just no one wants to think about it. But you you have to think about it during open enrollment. So yeah, yeah, um, cool any topics to discuss. There are just it's almost over is is life I Know you've said open enrollment goes another month for if people want to start.
04:51.45
Rick
Yeah, it's easier just to let it Bill.
05:06.26
tylerking
Ah, February first but are do you things are going to calm down. They must calm down a little bit after um, okay.
05:12.57
Rick
I think it'll calm down big time through the holidays. Um, ah you know what will shift to like updating our database. Ah. Got to get our yeah 2024 plans in for jd to be able to catalog people and then he'll start adding people's policies and so he'll have some time to sort of get organized around service. Um, and then yeah I think ah, there'll be another wave that comes in the first you know, maybe the last week of December and then the first couple weeks of of January. Um.
05:29.64
tylerking
Um, here.
05:36.76
tylerking
Yeah.
05:39.67
Rick
But yeah, it's very seasonal. The the cool thing about this open enrollment though has been um I can see um so so I have 2 things I want to talk about and I want to separate them because they're completely independent. 1 is like the biggest concern I think both of us have with this business is can we scale it profitably. Um, given the high service component um and sort of the seasonality right? like it's this It's it's like requires lots of focus for three or four months and then it's like dead and then how do you How do you make that work operationally, um, and then it's you know it's intensive like.
06:02.24
tylerking
Um, for.
06:15.34
Rick
So um, so so one is capacity I'll talk about in the second is ah I just want to talk about how like I think this this open enrollment is different than all the rest in terms of like observed learnings and how I think it'll set up a different type of year next year in terms of how we think about the business and growing it.
06:31.80
tylerking
Are.
06:34.15
Rick
Um, I know we've touched on that in the in the past but I I would love to dig into that today if we have time but on the capacity front. Um, ah I was talking to Jd on Wednesday and we we kind of separated into 2 capacities. There's like functional capacity which is how many.
06:39.78
tylerking
Um, Katherine.
06:52.56
Rick
Like if I was a robot how many like enrollments can I do with the time and energy that I have and then there's this other capacity which is emotional capacity. Um, and because a lot of Health insurance. Decisions are fairly emotional. Um. Could be someone has cancer or they're having a baby or they're having a divorce. Ah it can get and they and it and you know so some of them get into like super like nuanced things like hey I just lost my job I am I going to be eligible for medicaid like the um, the toll on like.
07:28.55
tylerking
Yeah.
07:28.72
Rick
Am I going to let this person down am I going to like if if I advise them the wrong way This family with a you know a serious health condition in their family or someone in their household has could could I could screw up their lives like and so I think that weighs heavy on.
07:42.38
tylerking
Are.
07:47.61
Rick
The leg up health employee or whoever's the advisor and or coach in that situation and so the more we can do so anyway I think I think we've we've sort of hit a limit with j d on emotional capacity like in terms of at about 2 you know 200 people but functional capacity. He's like.
08:01.96
tylerking
Her.
08:07.19
Rick
Um, nowhere near the limit. Um, and so it's a very interesting different problem. Yeah, so so the way where I wentt with this was and I'm interested in your thoughts on this um was with emotional. Yeah most of the emotional um toll comes from the uncertainty of.
08:08.30
tylerking
Wow. So what do you do with that? yeah.
08:24.99
Rick
Being able to advise confidently. Um, and so ah, this open enrollment. We're we're because of the volume we we're seeing a lot of edge cases that we haven't seen before like ah what if ah I've got nine nine family members and one of them is you know ah you know has a different dad and you know it's just like all this like. Very complex stuff that you don't you don't see until you get to like larger numbers. Um, so so in 1 way like this is just a rite of passage where in order to like become an expert on some of these edge cases. You've got to go through and advise on the expert. But then it becomes a sort of a tribal knowledge like documented knowledge center.
08:47.70
tylerking
On her.
09:02.62
Rick
Um, and so part of it's like maybe it just gets better with time. The other part is you you probably can contemplate this stuff to a degree if you're intentional about it outside of open enrollment and have sort of unemotional playbooks for you know 95% of the stuff.
09:18.60
tylerking
Yeah, it's tough though, you know so 1 person needs to be able to handle more than 200 clients at scale I realized we're not you know in the early days of a startup things don't necessarily need to scale well but like that's saying you know, ah, $100000 of revenue per. Person or whatever that doesn't work like um for a business.
09:37.65
Rick
Unless we have subscription revenue from a leg up benefits customer or some other revenue source that's juicing it. But yes I agree with you Two two hundred is the bare minimum to like where this thing can make sense but it's not ideal.
09:46.81
tylerking
Um, yeah, um.
09:52.85
tylerking
Yeah, so less knowing serum just got to about 200? Um, but like our model is a little different in that. Ah we hire almost entirely entry level people pay them well for like customer service but we're not like our engineers are not making a lot of money. But everyone has built in raises so they get more expensive every year. Um, with a you know, average tenure of about five years two hundred per employee is about breakeven for us right now. Um, so not that leg up health will necessarily pay people the same way. But yeah, 200 as just for anyone else. Starting a bit this is something I wish I'd thought about earlier because we kind of hired ahead of this we we hired what we could afford to pay in the moment not thinking well people need to get paid more as they get more experience and stuff like that I wish I had had this number 200 in mind because we would have hired slower which I think would have been better anyway.
10:40.90
Rick
And just to be clear. We're talking about $200 two $100000 of airr per employee per headcount and it's a very like ar per headcount is a very interesting metric to track and try to optimize around a target as you scale because it can give you competence that you have something that will um.
10:42.76
tylerking
Right? yes.
10:57.91
Rick
Have some margin and some cushion in there for mistakes and growth and retention.
10:58.57
tylerking
Yeah, so I have my head to 50 s where I want to be two hundred s acceptable anyway, I realize that's not what you're talking about. But yeah, if you're at 100 that's probably like I think a lot of businesses are like yeah we're not at that the number we need to be at you're not at it with your first employee but you got to get there. Unk d be a lot easier to imagine that like it's all achievable right? But the emotional thing is probably harder like normally what you say is oh we'll automate stuff. We'll we'll systematize stuff. It's hard to automate emotions you know? Um, but I think you're probably right that if confidence is the problem. You can definitely get more confident.
11:20.78
Rick
Are.
11:35.24
Rick
Yeah, and then you eliminate exactly. So there's only so much you can do but where where I I sort of dug in a little bit with JD and I was like you know what is it really? It's like well it's when someone asks a question that has a huge impact on their lives and we don't have the answer right in front of us.
11:37.98
tylerking
But you're still going to be thrilling with these hard situations.
11:52.00
tylerking
On her.
11:54.55
Rick
Um, that we're confident in I mean that requires a phone call multiple phone calls research online. Um, and then sometimes like it's so such an extreme situation that like there is no. There is no answer. It's like we're dealing with the government. We're going to have to work through this with you and that's a very unsettling thing as an advisor to feel.
12:13.74
tylerking
And again in these early stages. It's probably not worth doing what I'm saying here. But as this thing scales Probably there needs to be a point where you say this is this is too complicated. We we like we could figure it out.
12:29.86
Rick
We recommend you talk to so someone else like that. But we we found this person who specializes in this this is like if you really want to This is a serious issue We this is gets gets out of sort of our expertise. Let me recommend you to someone else.
12:31.82
tylerking
But talk to who oh yeah.
12:45.15
tylerking
Yeah, because like I you know we used to we we kind of still have this attitude of like help the customer with whatever you can, but sometimes they're just like oh you know I need to set up Mailchimp I don't know how Mailchimp works and we're like we got. We've just got to be like we can't help you with that I'm sorry that's that's between you and Mailchimp.
13:03.17
Rick
Yeah, here's here's a link to the help dot mailchimp.com website
13:05.11
tylerking
You know, yeah and then then they the customer says Mailchimp support sucks. They don't have help docs on this, you'll you'll pick up the phone. They they always try to get support from us on other tools and we we help a little bit but yeah, obviously with health insurance. It'll be different but I do think like eventually we'll need to say. This one client is taking up a ton of time but also a ton of emotional bandwidth and we just can't do that.
13:30.23
Rick
What both of these examples. The health insurance example and then also the mailchi example sort of Beg is like is there a upsell opportunity for like ah um, you know Premium Concierge service. Um.
13:39.17
tylerking
Um, you know.
13:44.00
Rick
Have you considered that from Mailchimp standpoint I think it probably applies in this case too.
13:45.74
tylerking
Yes, we've considered it. Um, every time I do the math on that it's like the the number of people who need that is low enough. Basically anytime we ever think about. Could we charge more money for something. It's like okay 10 people would pay us an extra hundred dollars a month but we'd have to spend like. Tons of time ramping this up as a thing we could offer I think it's different for leg up health because like lego health is a service business and building that expertise like is much more core to the like the business than I think providing Mailchimp support is a listening serum.
14:21.70
Rick
This is a tangent. Um, but at windfall we had our exec offsite last week in San Francisco um really hard trip by the way like I was gone Monday through Sunday um, we had our holiday party on Saturday so it just like worked out that the offsite were back to back and.
14:33.92
tylerking
Um.
14:38.43
Rick
Like part of my feedback I'm going to have to say like let's do those different weeks. So I can come home and you know break it up into 2 trips. Um, but but it was a really productive offsite we hired. Ah um, or I guess it's the coach of our Ceo who came in and did like a facilitation with the executive team and like worked through his workbook really cool like.
14:40.71
tylerking
Yeah.
14:57.94
Rick
Like thought process in terms of like how to spend exact offsite time in terms of not thinking about the business it like created all this space we spent most of our time like talking about how to talk to each other which seems so silly but it was very productive. Ah, but but ah.
15:10.73
tylerking
Um, it doesn't seem silly at all.
15:13.88
Rick
Anyway, there's this concept called ah that this that I'm now I see it everywhere now. Um, it's called the sucker's choice and um I can I use it as like what you just said was like either. You don't offer the service or you offer it. You scale it all the way up. Um, and it's like there's there's his his ah his. His his. You should check about his company's middle path consulting very cool. Um, but like the middle path would be like actually you could offer it. You know, paid to see bites and then shut it down in five months if if it didn't you know bite.
15:47.14
tylerking
Yeah I I think there's often opportunity for that for this specific one. What I mean is like we have to build the expertise in Mailchimp which we we don't know Mailchimp works. Um, so the amount of money we would get paid for those client like well they wouldn't.
15:57.40
Rick
Do you have to is or is that sucker choice. No see I see so you get the free consulting piece.
16:03.31
tylerking
We do if we know the answer we help them. Ah we would have to build up Expertise We don't have I think you're probably right that there's that the thing is even if it worked out there I feel very confident.. There's no ramping up the demand. Like there's no way this turns into a $20000 a month line of you know business for us. So at best. It's a very slight profit which is I Just don't think it's worth the distraction.
16:32.56
Rick
Yeah, yeah, usually like what I've noticed is that these sucker choice situations are often like our bias is actually saving us a lot of time by simplifying the decision into like a or B and oftentimes it is the right decision. Um.
16:43.19
tylerking
Um, but sometimes there's a c that we should consider.
16:46.14
Rick
But so but sometimes like you if you if you get challenged on it like there that it it opens up this. You know it's not a fork in the road. It's you know it's something else.
16:51.83
tylerking
Yeah I think that's a good mental model to keep in mind and I'm sure there's other ways in which I've messed that up I don't think Mailchimp is one of them.
17:01.20
Rick
Yeah, um, I'm just you know anyway. Um, so that's the capacity thing I think that's something we're going to have to like come out of this open enrollment. Ah period focused on fixing between now and next year and or fixing is not the right word but like addressing.
17:15.95
tylerking
Um, yeah I mean yeah I know it sorry I'm sound like a broken record here but just spreading so in physics. There's like this concept of.
17:18.98
Rick
Because it's not we can't fix it. Um.
17:30.30
tylerking
What does it impact and it's like force over time or something like that. Um, and the idea is if if you have like a collision between two things if if they're kind of elastic elastics wrong word but like rubber versus metal or something and it kind of spreads the collision out over a hundred milliseconds instead of one nanosecond it's the same amount of force being applied but it's spread out over enough time that the actual impact is much lower. Um I feel like spreading out if there is any way to spread out this really intense period of open enrollment. Over a longer period of time that would go a long way towards scaling up Jd to be able to handle more customers I bet.
18:09.41
Rick
That's that's a great segue into like why I think ah next year's open enromment's going to be different and then I'd love to hear what's on your mind. Um, so so like this past year it was all like we last year we exited openrom and all we did was individual health journeys and we were like okay this was like.
18:11.12
tylerking
Are.
18:24.52
tylerking
Um.
18:27.38
Rick
Interesting. Ah, but but we really want to be in the in the b two b space we were. We want to serve employers and so we spent most of this year up until middle of October figuring out how to sell group health insurance and service it and then what our leg up thing for this leg up benefits thing was which is our stipend like. Product shouldn't call it a stipend product which is our employer solution for companies that don't offer group health insurance and I feel like we figured that out in next year's that would be about like how do we get more It's like how do we scale which is the capacity issue and then how do we get more ah top of funnel. Um.
19:06.31
tylerking
Um, written.
19:06.79
Rick
And I feel like that's ah, it's going to be just being able to focus on that for a full year versus like figuring out how to do how to build it how to position it how to explain it is going to be really really interesting.
19:16.79
tylerking
Yeah, and yeah, if the employer thing opens up like oh we can get customers in April because employers aren't locked in to open enrollment I get I mean I guess during open enrollment this year J D wasn't doing a ton of sales. He was mostly just like fulfilling service. Expected service to kind of existing or new clients. But it it was about service. But yeah, that's another thing that a way to smooth everything out is to say you know the sales all happened during the slow months. This is just let's get renewals. Let's let's renew health insurance for all the people who we already have as clients.
19:52.13
Rick
Yep, and then just like formalize our relationship with the new people. Um, yeah anyway, ah thank you for for letting me talk that was therapeutic. What's up with you.
19:54.16
tylerking
Yeah.
20:03.65
tylerking
Um, yeah, still relatively calm I honestly had a really great past couple of weeks at work I I feel I just feel so good about the team right now. Um I think I mentioned like it's been about 2 years since anyone's left and everyone just likes each other and is happy and ike. Keep following. Um, no one in particular comes to mind but like you know, an amalgamation of lots of founders that I follow who ah like are more successful than me and they all want to sell or have already sold and it it comes down to their unhat like in. The way they got so successful is by creating an environment. They don't actually want to be in um and so I've been really grateful lately about just like like we had a holiday party last Friday and you know pretty much the whole company showed up and we did like a white elephant exchange and I mean it was just a really fun time and just a reminder to me that. Making a lot less money than others. You know the dream and like super like I wouldn't trade having a great team and enjoying going into work every single day for more money. Um I just feel really grateful for that right now. So I figured I'd share that. Ah.
21:11.11
Rick
Thank you that sobered me up a little bit like I Ah yeah, we should be more grateful for like the pros of the path that we're on versus because there's like yeah the yeah so there's certainly pros of the other path but it's not all.
21:26.29
tylerking
Yeah, like if you don't want the job you have right now. You're not successful I don't care what else is going on if you don't want your current situation if you want something else if you're looking forward to the next thing more than you're what the thing you're doing right now that's not success in my opinion.
21:27.90
Rick
Rainbows and sunshine.
21:44.60
Rick
I'm going to write that down one second. Um, that was a good one that should be the title of this episode where ah this is the 21 minute Mark ah, it's worth I think it's worth editing the title for this is the definition of success by tilllic king.
21:44.19
tylerking
That's kind of the 1 minute Mark ok um
21:59.89
tylerking
Ah, um, but that does lead into so ah this week we so there's an employee led group called idea which stands for ah inclusion diversity equity and accessibility. Um, basically like dei diversity equity and um inclusion work. Ah, it's kind of I do some de I like like the company officially does some dei work and then this this employee led group does kind of additional work above and beyond that. Um. And they had a kind of they have a monthly meeting which I normally don't attend because I want to. It's supposed to be employee led so I feel like me being there is counterproductive to that. But this was like the annual recap where they put a presentation together that was kind of like here's all the stuff we did this year. Um, and it was really great ah seeing. All the stuff that's happened this year on the de friend I tweeted about this and 1 of our listeners actually was like can you share more on the podcast. So I thought maybe we'd spend a little bit of time diving into this I know d I is a topic that a lot of people kind of roll their eyes at but it's been really important for less annoying. So I thought we'd talk about it.
23:09.73
Rick
Yeah, and I don't know if this is true or not but it it sort of feels like something that came and went um I don't know if that.
23:14.23
tylerking
Yeah but especially I so I think a lot of people probably well my my understanding of the timeline is from ah Michael Brown getting killed in Ferguson through George Floyd in Minneapolis. There was kind of this crescendo of interest in this that carried on for the next couple years after George Floyd and then basically layoffs started happening and interest rates started going up and everyone was like I think there are a lot of people who are kind of like reluctantly going along with it that were like. We can get away with whatever we want now we we can stop pretending we care about this and they all stopped pretending That's my impression.
23:52.62
Rick
Um, and I also feel like ah some of the the like recent massive Blowups Um I'm thinking of Silicon Bank and um I can't remember the other one's name but but I feel like Dei was like blamed almost for the.
24:03.26
tylerking
Ah.
24:08.76
tylerking
Yeah I mean you see a lot of it like the the harvard and ah Penn and whoever else. Ah, you know these college presidents and chancellors and stuff are getting in hot water and I again I'm not I'm not sure what it has to do with dei but it's certainly getting blamed for a lot of it. Um.
24:09.32
Rick
The failures.
24:26.22
tylerking
There's certain there seems to be a backlash going on right now which is unfortunate.
24:27.45
Rick
Isn it so funny. How things just go like at Flow E flow and we're in one of those es.
24:35.12
tylerking
Yeah, we are um and you know what I bet it's going to come back. But I I still care about it. Um, our company really cares. There are a lot of people who still care about I Just think like ah a bunch of billionaires and vcs have stopped caring. Basically.
24:48.29
Rick
What? what? Well What? what? what is making your your company and this committee like stay focused and ah amid all this.
24:56.71
tylerking
Yeah, um, so I want to answer that but let me answer it in a roundabout way which is like let me share some of the kind of failures slash my impression of why people kind of roll their eyes at this and let me let me start with you like I. I'm sure you've had moments I certainly have I think everyone has where you like see some people doing Dei work and you kind of can't help but roll your eyes. Do you know what? I'm talking about where and let me be more more specific where it's like is the work you're doing actually having any impact at All. That's the question I often. Ask myself when I see some of this work. Do you know what? I'm talking about.
25:30.47
Rick
Yeah, yeah, yeah, it's like I'm imagining um someone like picking up trash and then putting it like on top of a counter and then it blows off and then it it sits on the ground again and then they're picking the trash up and putting on the counter again. It's just like circular but not going anywhere.
25:46.13
tylerking
Yeah, like you know Google announces they're going to invest $100000000 in whatever initiative and then five years later it's like you know they're investing in getting more women in in programming and then it's like five years later you find out they actually have fewer women per capita at google than they did when they started that thing. And it's like does is any of this working does any of this matter. Um I think we went through that phase a little bit and and in particular my my observation is okay I'm going to say a bunch of shit I don't actually know about here. But. Here's my guess as to how a lot of things got where they are and that is I think um dei work seems to me to be dominated or it seems to have a very academic culture academic meaning like the academy like universities. And university professors are kind of well this is actually what the harvard and pen people just got in trouble for. They just talk and talk and talk and don't do anything kind of and to some extent listen my wife's professor my dad's a professor I have respect for what they do. Ah.
26:56.60
tylerking
It it serves a role but you can't just talk in research all day that is like step one maybe and then someone has to go take action and that's like that normally happens outside of academia. Um, but I feel like the di world is just a bunch of people having workshops and reading books and giving talks and having conferences. And for a long time I was kind of like well what? what are we doing? what What's the actual work. You know? Yeah, so um, we I'd say about a year and a half ago or something like that. so so the
27:20.96
Rick
Yep, So what does the actual work look like.
27:32.55
tylerking
The person the company who was kind of leading this ended up leaving her go to her own thing and so we had to figure out Well who's going to be in charge of this and all that and I took I I Certainly don't want to take credit for this but like my my instinct on anything that is like run it like a business kind of. And in particular run the project man not like run it like a business like you have to make money but run it like project management like how did Kpis work um or or okay ours but I actually don't I'm pretty fuzzy on what all these these terms mean but the basic idea of like let's set goals and let's figure out. Yeah.
28:02.76
Rick
Well that they're all the same. This is let's be very clear like like.
28:07.42
tylerking
All the same. Yeah, but I think before it was just like before where we were is. We're like we had a budget $10000 a year could go towards this stuff. Ah plus the fellowship we the coding fellowship we do or we teach people how to code that that's a meaningful extra expenditure but $10000 and we had a time budget which was like. Ah, basically four days a week of people's time um, can go towards de type work and then it was like well I guess let's fill that and so is like well there's this consulting company that ah does workshops on this and I think we spent honestly like ah a ludicrous amount of money on this. Um, and they came in and they gave a workshop and it was like okay ah but cool I learned stuff I don't even mean to like say it was a bad thing but it just wasn't connected to outcomes anyway, when we the thing we're doing now is we're actually saying what are like what are the constraints here right. When we're talking about lessening serum the product if someone were to come in and be like let's ah, let's build like the world's best project management system. We'd be like no, we're a crm that's not what we do I don't think we were doing that before so we kind of set constraints and then we said what are all the goals that could fit within those constraints. Let's pick 1 or 2 or 3 and then we said what are actual concrete things we can do to impact those like like can we make a metric we can measure and then how can we impact that metric. it's like it's it's how every other part of a business runs right? I'm saying like really obvious stuff.
29:35.48
tylerking
We started doing that and I have specifics I can share but like just that basic philosophy is I think all it took really.
29:40.74
Rick
The thing that stood out to me of what you said is like I feel like someone smart said something like the definition of strategy is what you will not do um and I feel like that's that's stood out. It's like oh no, this is not This is what this isn't um, ah that seems like that was a ah magical point and so.
29:49.47
tylerking
Um, her.
29:52.19
tylerking
Yeah, yeah.
29:58.10
Rick
Within this of you know smaller box. What can we do? Um, and yeah, it's like the minute you you use you shrink? ah ah, things become much more tangible. Go.
30:05.31
tylerking
Yeah, and so and I do want to I want to start getting into specifics because I'm anyone listening is well let me say 1 more vague thing before I do because let me talk about the constraints. You're just saying um let me talk like the worst part the worst. Period in history for less knowing here I'm doing de work here's what was going on. We had this budget. Everyone at the company cares believes in this and cares deeply about it. Um, or you know on average compared to other companies I think people care a lot about it but we're in this I think a lot of people have experienced d I work being like. Shame fit filled with shame and guilt and disappointment and it's it's all about how bad things are and like why aren't things better and we're going to talk about all the inequities in the world and so on and when we were really wallowing in that the mode we hadn't set these constraints and so people were like. Should we should we all go volunteer at a soup kitchen. There's this really great soup kitchen near our office should we go volunteer there. We have a $10000 budget. There's just really great charity I know about can we just give some money to that charity. Um, we you know, go go volunteer at this program summer program for kids that. You know, whatever and these are all great causes. But the problem is we were just a drop in the bucket for all of these and there was no continuity between any of them and I think everybody just had this attitude of the world is so fucked up and we can't solve all these problems which means we're failing.
31:35.10
tylerking
That was the worst and that was maybe a year and a half or two years ago where we were in that mode you can imagine how demoralizing that is right? Um, so the constraints we set we kind of did a whole reset and I talked about this on the podcast at the time but we did this whole reset with the idea of saying like let's let's focus on things where we actually can have an impact and so. 1 of 2 things has to be true for anything we work on number one. It has to either it. It has to be a byproduct of what we're already working on. Um I everyone probably knows this but classic example of a byproduct is you have a lumber mill you're sawingwood all day that creates sawdust. Take that sawdust packet with glue and make plywood or whatever. Um or particle board particle board and it apparently it actually was like they used to throw all this.
32:16.69
Rick
Is that what playwood is I mean that's I didn't know that that's cool.
32:28.44
tylerking
Sawdust away and then someone's like is there a way to like that's basically would is there a way to kind of turn that into shitty wood they do um so like the coding fellowship for us I would argue is ah is a byproduct. It's like we we have developers we already like have all this training like if you hire an intern or a new hire. You have to be able to train someone. Half of our Dev team didn't know how to code when they started here I taught them how so already have this whole cycle of like getting someone ramped up as a developer. What have you just offered that to people that's a byproduct so that's one way something can qualify the other way is directly reducing harm that we directly caused. So my example of that would be like like we compost and recycle in our office St Louis is kind of backwards and like the city doesn't do this stuff so you have to pay private companies to come and do that. Yeah, we are the ones creating this waste. We should try to dispose of it responsibly. We're not going to go up and pick up litter outside right? That's not like. We didn't cause that problem. It's we can't solve every problem in the world but we can try to reduce the harm that we're causing as a company. Um, so those are the the main constraints that I kind of put on what this work could be yeah, so um, we kind of as a company got together and said well what are the main things within that like like what are the main goals.
33:33.70
Rick
So what's come out of that.
33:44.10
tylerking
That we would like to target um and we kind of focused on really to I think we technically define them as 3 things but in my mind they're kind of 2 things 1 is um from a diversity standpoint we would like to hire more black people and. I think people get uncomfortable like saying something that bluntly but let me explain what I mean here with diversity. It's hard to ever be like like quotas and stuff like that feels really uncomfortable. But I think it's useful to be able to say what is the goal here. What like what should it look like if everything's going well and I think like a nice like. Any company can do. This is say what community do we exist in or if you're a remote company. What are all the communities we care about the company in a perfectly equitable world. The employees at this company would probably look something like the members of the surrounding community um St Louis is a city with a high white population and a high black population. Like it's more or less a 2 race city. Um, we have a lot of white employees. We don't have a lot of black employees. We. We actually it used to be women. We actually think like have addressed that and that's no longer a shortcoming of the company. So we just looked at and said that's very clearly the biggest discrepancy between the community we live in and the company last swing serum. That's going to be 1 of our targets now that's that's kind of like the in. Ok our world. That's the objective more than the key result if I understand how will we do that? Yeah um, oh ok, the key result is how we'll measure. Whatever there's that then there's like what's the actual What's the actual thing we're going to do to move the needle. Um.
35:05.87
Rick
Yeah, how So yeah, the key results typically how you will measure success. Yeah.
35:19.28
Rick
Um.
35:19.46
tylerking
I Haven't said yet what we're going to do to move the needle but we we agreed on that goal. Yeah.
35:21.56
Rick
So just just a tangent on okayrs for a second. So every time I talk to someone about oks I get like confused but the way I just want to be clear but with you about how I think about. Okay, there's objective and then there's key result Objective is like the fluffy stuff like explanation should be.
35:31.96
tylerking
Um, me too.
35:39.31
tylerking
Um, in earth.
35:40.28
Rick
Like pump you up kind of thing. The result is how you measure whether you accomplish the objective. But then that cascades that key result becomes another objective and then you set key results on that and so it should like you know work. Its way down. Yeah yeah.
35:44.10
tylerking
Um, ok.
35:47.17
tylerking
Um, it gets more and more specific specific as it goes. Ok so the objective would be like be an equitable workplace that marks as our surrounding community and then the key result would be. Percentage of black employee or percentage of employees of less serum that are black something like that. Okay got you? Ok but so that makes sense thanks for clarifying that there's still the question of like at a at a company as small as ours where there's really only 1 level. Ah.
36:02.82
Rick
And you could have more than one key result per objective that spiders from there.
36:18.15
tylerking
You need the next like the next thing which is well what? what the fuck are you actually going to do about this.
36:21.65
Rick
Yeah, and and that is where um so many people fall down with okay ours is they try to make it like like too many levels. It's like just jump to what you're going to do and call that a result. Um ah the the general guidance is I spent a lot of time on this. So I think it's useful to talk about. Ah.
36:28.76
tylerking
Um, yes, right.
36:38.35
Rick
Generally the guidance is like be clear about like what the outcomes are um that you want to achieve and then you know it's worth going into like some measurable outcome because that's like it forces you to it forces you to like build infrastructure around ah long-term success criteria um, but then like the the thing eventually you've got to get to like binary projects like a one or zero I got done.
36:49.87
tylerking
The.
36:58.70
tylerking
Um, yeah.
36:58.21
Rick
Um, but that doesn't have to happen within an okr. So what I find helpful is like set the measurable outcome and then have initiatives that you think you're you're going to try related to the okir that that whether you do them or not or whether they're those things are successful isn't the goal. It's whether you move the needle in the number.
37:13.33
tylerking
Yeah, that makes sense the the the other comment I'll say about this is I think the number itself is more important in a bigger company where there's kind of a trust issue or just like if you're delegating someone something to someone who delegates it to someone who delegates it. You can't use personal judgment as much at a company our size a 20 person company. So like the other one. The first one was what I just said the other goal I don't think I need to be able to measure it with data I think I can look at and be like yeah, that's better and that is we've decided to make our ah our software more accessible for users with disabilities.
37:49.24
Rick
That's oh what early that is interesting.
37:50.51
tylerking
Yeah I Think that's this is one I'm I'm particularly interested in talking about because I think the whole world. The Dei diversity equity and inclusion I think people really focus on the diversity part of it and there's a lot of other work than just like hire people from underrepresented groups and the. Type of person who's skeptical about this because it's overly academic. This is the one that's not at all academic. It's like can our software be used by somebody that doesn't use a mouse. That's a pretty concrete question and. Making it better like a classic example in the de world of like why it's especially accessibility white like accessibility matters is like Curb Cutouts on sidewalks. Um, if you've ever had a stroller or been wheeling luggage around you probably appreciate that the Curb cutout exists so that you can get from the curb to this Street. Um. That exists as I understand it because of the Ada for people with wheelchairs. That's an example of like it really doesn't cost much to do it. Everyone's life gets better, but it's done because of accessibility concerns. This is one where like even if you're not disabled, you probably prefer having better keyboard support in lessnoying serum. Um, it's just a win win win. It's really related to our product. It's not like let's go volunteer for a soup Kitchen. It's let's make our product better.
39:05.17
Rick
Yeah, exactly I it's like what why are you already doing this.
39:11.41
tylerking
Yeah, um, and that one ah, that's been like super energizing we had. We have a handful of I mean we probably have more blind users than we realize, but um and it's not just for blind people. But um, one in particular reached out. Earlier this year and was like when we were ah still honestly pretty early on and kind of embarrassed about where we were at and you're shining. He's like I can tell you like we didn't tell him anything he was just like I can tell you've put some time into this this is like I've tried a bunch of c ourms is is the only one I can even use at all. There was like here's some feedback on some more things you could do and we did it and he like. Emails all the time he had me on his podcast like we've got this great relationship with this kind of advocate in the disability community of that just wouldn't have existed if we hadn't done this so there's a lot of really good feelings around that um, but to the ok our thing I don't really feel the need to put a metric on that because it's like.
39:53.92
Rick
So cool Now that's so cool.
40:05.84
tylerking
We ship something. It's like okay you couldn't use a keyboard and now you can um so yeah, ah, where are we going? Where am I going with all of this. Yeah you got a thought.
40:08.46
Rick
Um, yeah.
40:20.30
Rick
Ah, part of this was a listener request but like I think like what? what? what do you? What? like if I take 1 thing away from this like or like what do you want there? There's kind of a soapbox. There's there's a yeah, there's a bit of a soapbox here. so like what but yeah so what what is the point.
40:26.70
tylerking
Yeah, can I get 2 things instead of 1 Yeah, absolutely let me give you 2 things instead of 1 so one is.
40:37.92
Rick
All right.
40:39.93
tylerking
The culture at last knowing serum around dei work right now is one where we celebrate wins. We're excited about all the progress we're making um that the meeting we had was not oh the world's fucked up here's the things we aren't doing well here's how it was. Look at the actual progress we've made and how things that were a certain way a year ago are better now and how they're going to be even better a year from now again, it's exactly how you'd treat any other aspect of a company celebrate the wins try to have a positive attitude I just don't think that happens or at least at lessening him that that wasn't happening in the de work we were doing. And it just completely shifted. Everyone's energy levels around it. So that's one thing I'd say and then the other one I'd say is while I I kind of agree with the skeptics that the the dei world is full of a lot of fluff and talking it all. You have to do for it to not be that way is just. Pick things to actually do and do them and we're actually seeing impact so the fellowship I've mentioned um like again, our app is more accessible. We've partnered with a bunch of student groups for various marginalized groups of people in local universities and given talks and stuff like that and gotten a lot of feedback from them that. Like I have a handful of people I can say who work in tech right now that said they probably wouldn't without lessnoing serum's influence. Our office is more accessible. We we audited it. Very simple just like we had to move the microwave down three feet because it was too high for someone in a wheelchair to access like very basic stuff like that.
42:14.60
tylerking
That's concrete and it's not theoretical. It's not academic. It's like move the fucking microwave and I don't know like the work can actually be pretty practical I think.
42:22.77
Rick
Yeah I think 1 thing that I took away from what you just said is generally when we hear people talk about d I I should say when I hear people talk about de I think of it and it's very abstract. It's like okay that.
42:37.48
tylerking
Um, yeah.
42:39.81
Rick
Do action here like I don't know how to translate it that into my life So it it becomes somewhat of like ah like background noise like you just don't hear it anymore. Um, and what I heard right? there is There's actually like some very basic things that every single individual.
42:48.31
tylerking
Um, yeah.
42:58.29
Rick
Or company can do that has a meaningful impact on inclusion.
43:02.50
tylerking
Like and pretty minor thing like I don't think every company should even have the level of like I I think we probably objectively spend more money and time on this than a lot of ceos would want to but if you just gave someone half a day a week to to go review some of this stuff I mean a a lot of stuff could change and and the team would feel really good about it. Um I I don't like giving the argument that you do d I work for the roi I prefer just it's the right thing to do do it for that reason. But if you are looking for it. Team morale. And at least at at this company is so much higher because of this and it really doesn't take that big of a commitment to get people excited about the the de I work. So yeah, thanks your thanks for listening.
43:48.70
Rick
That's cool. Thank you for sharing that? Um, yeah, ah my I'm I am positive that our my our microwave is Ada accessible because it's basically on the floor like.
43:57.50
tylerking
And on the floor.
44:02.76
Rick
I Think it's in this. It's It's the weirdest thing for me because I'm used to like reaching like up here. You know like I'm like I like above the stove for microwave. It's it's like in a cabinet below the counter. Yeah.
44:05.53
tylerking
With.
44:16.39
tylerking
Yeah, it's a type thing you never you never think about um that there were a dozen different little things with our office where it's like super easy to change. But you know apparently and and as soon as you hear it, You're like oh yeah I see why that matters. But anyway that that was my soapbox Thanks for listening.
44:31.62
Rick
That good job now I like that um the ah, there's something that I thought of when we were talking when you were talking that I wanted to talk about I forgot what it was I should I was like I should write this down and then I didn't write it down. So now I've lost it. Oh well.
44:44.93
tylerking
Um, too bad. Um cool I've got a couple other little updates I could give but um, we got what 10 minutes here anything else. You want to talk about but you lost it. Um all right? Well if you remember it interrupt me we can dive right in but since we are talking about that I mentioned should segway you got it.
44:52.89
Rick
I mean I did have something but I it's gone. Yeah, all right? Oh yes, um this is another learning from the coach on how to talk because we literally talked.
45:02.39
tylerking
Ah, no yeah, go for it.
45:10.27
Rick
We like talked about how to talk we practiced how to talk and then we actually talked about things that we needed to talk about um, but 1 thing I noticed I learned that I that I do and I have ah it's actually really not good for for clear communication and I'm just sharing this because I don't know if you I don't think you do it actually I think you're actually really. You would just ace this guy's class without even have to study. Um, ah yeah, rub the shows off. Um, but but they ah but but but if you if you have like formal management sort of training or you you have an Mba. We're taught as leaders to talk it as we like.
45:30.64
tylerking
Cheer. Cheers! yeah.
45:47.78
Rick
Let's us go do this. Let's we should do this and it's actually when you're trying to communicate something extremely confusing when you use the word we um and I so I've always struggled with window I Overindex on we but I found myself since learning the difference between like I and we and specificivity of like who we is when you're using we.
45:48.22
tylerking
Um.
46:06.99
Rick
Now I'm like finding myself saying we and I'm like actually I mean like 3 people not everyone. Um, so ah, it is but you can still say like Steve Johnny and and I like ah so.
46:12.34
tylerking
Um, it is hard when it is 3 people though because the pronoun is still we for that.
46:20.21
tylerking
Um, yeah.
46:23.60
Rick
Um, anyway, that's ah, this sort of little trick that came out of this coaching session like pay attention to um when you're saying we to someone when you actually mean like you and 1 other person decided something that you want that person to ah you know act on they actually aren't part of the we and you just need them to to get it done. I'm I'm finding myself. Maybe that's unique to me. But I'm finding myself like I'm saying like we to a group of salespeople and what I'm actually saying is ah me and the Ceo have decided the Ceo and I have decided that this is the way it's going to be.
46:44.10
tylerking
Um.
46:55.55
tylerking
Yeah, so I like that just from the standpoint of like precision and honesty tends to be good but is that is the thought here that if you say we inappropriately that the person listening is like well hang on I didn't say that and they they kind of think you're bullshitting them is that ok.
47:10.70
Rick
It's it's confusing. It's like wait wait like either you're manipulating me um, intentionally or like now I'm confused like I would I miss a meeting where this was decided and I was part of that. So.
47:15.61
tylerking
Ah.
47:23.51
tylerking
Yeah there's a different form of I think like 1 form of it is ah trying to give people credit or trying trying to make it feel more like a team. Um and build consensus. That's 1 reason someone might say we but the other form is like a lot of solo founder like very early stage startups will say we to pretend to be bigger than they are. And that that's an especially bad one because like the other person knows like you're not fooling anybody with that. Yeah, and then you put a hello. Yeah, exactly and I you and I but like.
47:47.44
Rick
And let me hold 1 second let me call um our legal team real quick.
47:57.70
Rick
Ah.
47:58.98
tylerking
Feel like it's zayn benefits where you and I both like our first job out of college. There was a whole lot of like pretending to be a bigger company than we are I I remember one day way. Ah, we had a client coming in and we had an office with maybe like 25 seats like cubicles and seat. But like maybe 16 employees.
48:03.13
Rick
Yeah I think it worked.
48:16.59
Rick
I care I know where you're going with this but your mom and we literally had family members sit pretending to work I remember that.
48:18.81
tylerking
And so one day they were like everyone bring your friends in tell them to dress in business casual and sit at a cubicle. But yeah was so stupid. Um, but okay maybe I don't know if it worked or not.
48:34.64
Rick
Ah, that's a true story that is not made up I'm embarrassed to have been a part of that.
48:39.38
tylerking
Ah, were you were you? Ah I think that was I didn't I don't remember you being like the ringleader behind that maybe you were I don't know that I was before the layoffs right? Yeah what you? yeah.
48:42.92
Rick
Oh that was pre me being like that was before the big layoffs. Yeah yeah, we were We were peons at that point.
48:52.96
tylerking
But yeah, maybe if you really put effort into faking it I mean there are plenty of hucksters out there who get away with faking it. But um, generally speaking I think saying I for a solo founder is ah a much better way to to communicate that stuff. Yeah, um, yeah think thanks for saying that though and I appreciate you saying I.
49:06.35
Rick
It's It's more honest.
49:12.76
tylerking
Do that naturally but I ah I'm going to try my best to have that in my head and and do better as well. We're going to. We're going to remember this Rick.
49:17.86
Rick
You said I right there. It's a good job. Yeah, um, all right? Well I got to run but um, so maybe um, if you'd like to review past notes and past episodes and show notes you can visit start blast.com
49:26.86
tylerking
Um, okay.
49:31.79
tylerking
For roughty here.
49:35.61
Rick
Um, otherwise ah hope the intro is was pleasant.
49:40.20
tylerking
All right talk to you later? ah.