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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.
Tyler King (00:00)
In this episode, we talk about the challenges leg up health is facing during open enrollment. Let's go.
Rick (00:23)
What's up this week, Tyler?
Tyler King (00:25)
Not a whole lot. I feel like you've got all the activity going on right now with leg up health stuff, so maybe we can start with you.
Rick (00:34)
Yep. So, ⁓ first, ⁓ last time we talked, there was an email issue and I want to provide a quick update on that. it sounds like one, same grid is notorious. our email provider is send grid front. The tool that is having the issues issue is send grid is provider send grid.
Tyler King (00:52)
they only work
with SendGrid or like they have multiple providers and you chose SendGrid.
Rick (00:56)
That's
their outsource SFTP server is SendGrid. ⁓ We're having issues with SendGrid on our own system. They're having issues with SendGrid on their side, sending our emails. It sounds like you've heard from some listeners where they've had issues with SendGrid in the past. So SendGrid seems to be the issue. We've narrowed it into it's a SendGrid issue, but it's not a SendGrid issue in isolation. It's a SendGrid issue in multiple places or like in multiple different like rel-
I don't know what the right word is, like ⁓ instances of Syngrid. ⁓ So ⁓ the front people are still working on like understanding what's going on from there. And with Syngrid, they did get in touch with someone and they said that our, our, ⁓ send it, our sort of portion of fronts Syngrid is compromised. ⁓ they, and they haven't provided details on why, but I don't know if remember, but we got, we got fished.
Tyler King (01:52)
yeah.
Rick (01:53)
a year ago or so, and I don't know what it was, ⁓ we addressed it. It was a very minimal impact. ⁓ No impact on the business operations. was just like someone used our hacktist to spam a bunch of people. ⁓ And we fixed it really quickly. We addressed the security issues, but I, yeah.
Tyler King (02:12)
Just to, can I make it,
because someone, a customer might hear that and think our email got hacked. The SendGrid account got phished. So only the ability to send emails, not the ability to read any emails that were received. So no customer information.
Rick (02:26)
Correct. Yeah, exactly. And so anyway, I think that's probably the root issue here ⁓ is that we have some sort of like flag still on our account with SendGrid that is affecting our any, any emails associated with the leg of the leg up health.com domain. That would be my hypothesis at this point. ⁓ I have a workaround with front where we can use, we can set up a Google group for each of the groups. It's just a cost thing. Like what I've told friend is like, we already pay you guys a lot of money.
It seems kind of crazy that we'd have to pay another tool, a lot of money to use a core function of your service that we're paying a lot of money for. Um, so I'd really like to fix this. Um, but they're not moving super fast. We're, small fish. Um, but anyway, that's the update note. The update is no very minimal, like solution progress, but progress and understanding.
Tyler King (03:16)
Well, can I also say, why
are we sending bulk emails through Front? Like, I just didn't, I didn't even know Front did this. This is not a core part of what Front is for.
Rick (03:23)
It's
not a bulk email. ⁓ it's so we have a, we have Google, we have groups like help at windfall.com. so the best example of this is that's uncontrollable is let's say someone comes into leg up help.com, which happens and they chat. ⁓ if they leave the chat, they help at went at leg up help.com sends a. ⁓ transcript or a follow up email to them that bounces currently because it's going through the front email system.
Tyler King (03:51)
So,
like Less Annoying Serum uses Front, and we have a help at LessAnnoyingSerum.com. We just have a Google account for help at LessAnnoyingSerum.com, so it's going through.
Rick (04:00)
That's
the work around is we could start using Google's sending service by setting up an actual account help at, sorry, it's a Google group currently. It's a Google group currently. We need to switch it to a full account, but that's hundreds of dollars a year.
Tyler King (04:06)
Okay, so not Google Groups, it's just a full account.
Okay.
Yeah.
Rick (04:18)
So it's like, okay, why are we paying for rent?
Tyler King (04:23)
Yeah, I just, that's not what front is. They've never been the email sender, I don't think.
Rick (04:23)
for the collaboration, yeah.
That's what we've used them for the entire time we've been there. And they have two options. You can do it through a Google account or you can do it through their SFTP servers.
Tyler King (04:39)
Yeah. It's a, yeah. Okay. It's a shame they're using SendGrid, I guess.
Rick (04:41)
So yeah,
exactly. I think what I probably need to do, I mean, I would like to leverage front's clout with SynGrid to get an answer on what's going on with SynGrid, because I think that will help us with our own issues without having to move off of SynGrid potentially. But it sounds like ultimately the solution here is we gotta get rid of SynGrid.
Tyler King (05:02)
I mean, paying Google $200 a year, I would do that anyway. Like SendGrid's never gonna have the deliverability that a full Gmail account has. That is such a small amount of money for such a high impact thing.
Rick (05:14)
We have
four of these groups. it's, it's, it's no, we can, we can, ⁓ I think we could probably live with not sent. There's an occasional case where the other use cases compliance. So, ⁓ appointments at and commissions at, ⁓ we use those, those listservs to approve direct deposit changes, ⁓ with carriers licensing stuff. and it helps have a group.
Tyler King (05:17)
Do emails have to go out from all four?
You receive
emails from them.
Rick (05:45)
to receive and sometimes they say we need the email on file to send us the person with the email on file. And I have these emails on file with everyone. So anyway.
Tyler King (05:54)
That is crazy. That doesn't make any sense from security. Cause you can spoof any email from address like that. Okay. Okay. Well, sorry. Yeah. I would get at least the important one that goes to customers. I would get that moved off of. Yeah.
Rick (05:59)
Talking about insurance companies.
Yeah. And a Google group.
And then we need to decide, like I think in February, after open enrollment, we can decide what we want to do with our transaction emails for like a Pelt account. Like it sounds like it isn't. I think the thing that's scary to me is the monthly update process, which we use, we have a template.
Tyler King (06:19)
Yeah, it's not that hard to move them off.
except if they're
not going out, then there's not much to lose here.
Rick (06:31)
Yeah,
yeah, okay. ⁓ Well, I would like, I mean, maybe we could just quickly solution then. So the solution that I have in front of me now is move to Google groups on front, ⁓ pay Google a couple hundred dollars a year per account and just get over it. ⁓ And then move off of SendGrid to Postmark for our leg up transactional emails that we're sending from our servers. And ⁓ I guess the question is like, what's the effort involved in?
transitioning from sync grid to postmark.
Tyler King (07:03)
Yeah, the effort for me is minimal. Let me just walk through what I think is involved. You set up the Postmark account. There's like various DNS things like DKIM and I forget all the different acronyms, but like to prove that we're sending on who we actually are, who we say we are. ⁓ Once it's set up, I think there's two parts of it. One is I need my code to call the Postmark API instead of the SendGrid API. I think that's very easy.
And then the other part is JD, what you were referencing earlier, JD uses a SendGrid specific feature that basically it's more like how like a MailChimp works. It's like a kind of, write an email in SendGrid itself and then it kind of merges in all the data for the different people.
Rick (07:51)
He uses mustache, think is what's called the template inks tool and takes variables from the API call.
Tyler King (07:58)
Right, so the code,
he pushes a button on code I wrote that calls ⁓ SendGrid's API, but the actual email content is stored in SendGrid, not in our system. So that way he has an editor, he can go in and change the email each month. Do other tools have that? Maybe not, that might be a weird tool.
Rick (08:17)
⁓ I'm almost
positive postmark has something similar. And if it doesn't, there are other workarounds he could, that we could come up with that either make that monthly update less ⁓ variable ⁓ within less editable by him. ⁓ Like we just create a transaction email that template that is less. Yeah. And then maybe he has some variables he can change in the backend, you know, like the change, the opening line.
Tyler King (08:38)
Yeah, it's just the same every time.
Rick (08:46)
You know, like, so.
Tyler King (08:46)
Yeah.
Okay, well yeah, let's talk about that, on my end, I don't think it's very hard.
Rick (08:54)
Okay, that's good to know. Thank you for, I will, I'm gonna let this play for the rest of this month and then we can decide what to do in December.
Tyler King (09:02)
Cool. Yeah, what else is going on at Legat?
Rick (09:05)
this that, I mean, this is business update, I guess. ⁓ so we hit our goal for context for everyone is like up health. hit our goal for the year. We surpassed 20 K and, monthly recurring revenue. That's great. We've got to, like lead purchasing. So in terms of growth and open enrollment, want open enrollment to be this awesome thing, but there are two factors that are, that are really impacting us. One is, ⁓ the ACE there, there is, ⁓
I don't know if everyone followed the, the, you followed the government shutdown, but basically when the major issue for the Democrats was there are some serious subsidies that the Biden administration expanded for health insurance and the exchanges that are expiring at the end of this year. Um, and the, and the most important piece of it is like, if you make more than like 400 % of the FPL, which is, uh, I don't know a couple hundred thousand, like $120,000 family of four.
Let's say you make $121,000. You don't, you, go from receiving $20,000 of subsidies to receiving zero subsidies. There's a big cliff. These extent, these extended subsidies fix that long story short, the subsidies are going away at the end of this year and premiums are skyrocketing like effective premiums. The people that the, the amount of money that people have to pay out of pocket is skyrocketing. And so we're seeing people.
Tyler King (10:22)
Yeah.
And both of these
things, right? Like both premiums are going up and subsidies are going down. So it's like a double whammy.
Rick (10:31)
Yes. That's
a double whammy. And so it's impact. We have a lot of what I would call. Like a lot of people like our ICP from a consumer perspective is someone who's right on this threshold. Like we serve the 400 to 600 percent FPL people, business owners of America, you know, and they are getting crushed. Like it's like these people are are like, can't I can't justify paying.
you know, going from paying $5,000 a year to $2,000 a month. Like, I'm sorry, I just, I can't justify this. So what are my options? And so the answer is you either go uninsured, you buy a short-term plan and like, hopefully you don't have a pre-existing condition that isn't covered, or you buy a crappy fake plan that has gaps and it's fake insurance.
Tyler King (11:29)
So just like, yeah. So just huge parts of the country are gonna go from having like full legit insurance to somewhere between no insurance and like kind of garbage fake insurance. Yeah.
Rick (11:30)
Or you pay the premium.
Yes. There's no other option.
I, it's and so anyway, I, I think there's going to be a, I mean, if you, if you lean Democrat, you're going to be happy that the, of the blowback the Republicans get on this because it's going to be very, very ugly. ⁓ people are going to be pissed about this once they, once they wake up. I'm surprised the, and I'm surprised the coverage isn't more aggressive right now.
Tyler King (12:03)
Yeah.
Yeah, because I mean, we're talking, I know you just gave numbers and those are big numbers, but like, I feel like every year health insurance premiums go up and most years it's like more than inflation. this is an ongoing, you know, the old saying that like people act like ⁓ it has to be big problems only. People only care about big problems if they're sudden, right? If there's like a hurricane and it destroys the city, everyone's like, that's a big deal. But if there's like a slow problem,
that destroys the city over 20 years, no one cares. ⁓
Rick (12:38)
Yeah, it's
the relative like relativity effect like like you I think the saying is like if you throw a frog in a pot of boiling water, he's like jumps out. But if you put him in cold water and slowly heat it up, you cook him.
Tyler King (12:47)
Right.
Yes. So I feel like we're all frogs boiling in the water of American healthcare over the last, over our entire lifetimes. But like, this is a sudden problem, a new problem on top of it that normally you would think would get a lot more attention than it, than it's getting.
Rick (13:07)
Yep. And it's, think, I think the pressure is going to, going to amp up here in the next 30 days. So, but the, but, but timing wise, like people are making their health insurance decisions right now. So it's great. It's creating a lot of administrative headache for the system. ⁓ anyway, it's supposed to work. So, ⁓ anyway,
Tyler King (13:16)
Right, it's too late.
Are there
opportunities for leg up health here that, I mean, obviously it'll be a hit in the short term in the sense that churn will go up and it'll be harder to get new clients, but what might happen in the aftermath of this?
Rick (13:36)
Yeah.
So I think like I like we always think like that, like when things aren't going well, there's opportunity, right? Or when there's change, there's opportunity. So I think in the meantime, like we're going to differentiate, we're going to expand the consumer plans that we offer and deepen our expertise and non ACA or non Obamacare stuff. And so that's going to be good for our customers in that we're going to have a more confident opinion about when it's okay to buy health sharing ministry or
how to educate someone on a short-term plan and how to think about it. And I think that'll be good long-term for our customers. I also think, you know, well, I mean, people are, it's hard to put lipstick on a pig, though, right? Like, how much value are we providing, even if we say, hey, we're getting you crappy insurance instead of you paying us $20,000? I mean, is that something that gets referred? Like, it doesn't feel like we, the counter to this is like, I feel like,
the referability of our services is really going down right now. Like, like no one's having a great experience and saying, wow, yeah, exactly. And so I think the word of mouth component of our business suffers in the short term. ⁓ but anyway, ⁓ I think, ⁓ well, ultimately this is all going to lead to is it's, it's, it's kind of reaching another breaking point. We were at this 10, 15 years ago when Obamacare passed. And I think we're, we're approaching that now. The difference is we have a Republican administration.
Tyler King (14:34)
Yeah.
Right, even if you're giving good advice, their outcome is not good.
Rick (15:00)
And the question is, will they do anything? ⁓ And if they do, what does it look like? And I think that ⁓ there are opportunities that if they can do stuff that for us to seize the opportunity, come up with an innovative solution, that sort of thing. But fundamentally, the issue is insurance is just fricking expensive. And if the government doesn't subsidize it, you know, in the guaranteed issue world, you know, like for preexisting conditions are covered, then like
Tyler King (15:15)
Yeah.
Rick (15:29)
It's unaffordable. you know, either you subsidize it, you make it a government sponsored program with private upside, you know, on a base plan, or you remove pre-existing additions and figure out, you separate like the risk pools from healthy to sick, and then there's a whole other issue at play.
Tyler King (15:32)
Yeah. ⁓
Right. So, ⁓ I'm going to give a thought that you shouldn't do because I think it would be a waste of time, but just to say, we've talked many times on this podcast about how certain types of content that work for some businesses don't work for either of our businesses because, and in particular, I'm going to talk about a newsletter. No one wants to read a newsletter about CRMs generically. If you're a customer of Less Knowing CRM, you might want to read about new features and stuff, but you're not like, I just want to stay up to date on the CRM industry.
I think the same thing is true with health insurance. This might be a rare moment where a temporary newsletter would actually get some interest because it's not a newsletter about health insurance, it's a newsletter about politics, but specifically how politics affects health insurance. ⁓ I bet there are a lot of people who would be like, I see this as a big issue, no one's talking about it, I would love to subscribe to a weekly or monthly update on just what is the situation right now.
Rick (16:47)
Interesting.
So just to recap what I think you're saying is because this is going to change a lot and people are interested in how it impacts them personally, there is a content opportunity to provide unique perspectives and help people follow along as the change occurs.
Tyler King (17:07)
Yeah, and just generally, nobody's interested in health insurance, but lots of people are interested in politics. Like, lots of newsletters are about politics, and lots of people have obviously subscribed to those.
Rick (17:13)
Mm.
Yeah, mean, is what I mean, fundamentally, this is why back in the days, they benefit such a big following as we made it political. Like our our content was like fighting the departments of insurance and what like literally documenting the conversations that we had with them.
Tyler King (17:33)
Yeah, it was interesting because it wasn't really partisan, right? It wasn't like Democrat versus Republican. It was like all 50 states have this fucked up insurance system and we're fighting against it.
Rick (17:35)
Yeah.
Yeah, that was my favorite part of my job too. Like back in the day is like, loved carrying that banner. It's just, yeah. So, I'm right. I wrote it down as an idea. Yeah, it's a good idea. But even if it's not something that I think proactively updating our customers, even if it's not in a newsletter on our perspective, like that's the extreme version of like effort.
Tyler King (17:54)
I don't think you have time to execute on that, but I think it could work. Yeah.
Rick (18:12)
required to go after that opportunity. But there is another version, which is once a year or twice a year, we email all of our customers and prospects and we say, Hey, we just going to want, we want to proactively update you on what's going on in Washington related to health insurance. ⁓ and also give you some perspectives that we have. and, hopefully this is valuable to you. I don't think like anyone's going to get that email and say, I really hate that you sent this to me. ⁓ you know, it's like, thank you. so I think that's like, like a nice thing to do for our customers. that, ⁓
it leads to content, but it's not like making a monthly commitment.
Tyler King (18:45)
So yeah, maybe to connect the two, originally said, you don't know, like, this is gonna hurt referrals because like the end result is bad, even if the advice you're giving is good. People might still, I could still see someone saying like, listen, things are fucked. It sucks that Legop Health couldn't solve this for me, but I at least feel like I know where things stand. Like I'm glad I'm on their newsletter.
Rick (19:06)
Yeah, yeah, that's a good point. Like, uh, I think the larger theme here is like what differentiates us from other players in the space is our willing to edu our willingness and focus on education versus sales. And I think that like in times like this, where the options are not great, like we need to do more to educate on what future options might, might entail and how we're helping to facilitate that or advocate.
And we should do that. So thank you. That was a really good opportunity. only other thing I would say that's affecting us is, I mean, don't know if you're seeing this at Less Than Learning CRM yet, but I am seeing a massive change in search traffic across my personal website and LegUp Health, where people who would normally hit blog type articles through organic searches are no longer hitting the site and instead just reading content.
in chat bots and or in AI summarized searches. And it's, think it's having a pretty huge impact on our organic word of mouth and Legion, ⁓ particularly content Legion. Do you have any thoughts there?
Tyler King (20:20)
We predicted this, right? So first you said, has this happened at LessonWing Serum? We've never really had that type of content to customer funnel. ⁓ The serum equivalent of this would be like you write a blog post, it's like 10 ways to increase leads for salespeople and someone finds that and then they're like, what's LessonWing Serum? We've never gotten that to work. So we do have a lot of those blog posts and they do get some traffic, but that traffic never converts. So. ⁓
I have no idea is the answer, but it wouldn't hurt us if we lost all that traffic.
Rick (20:55)
man, well it's, ⁓ mean my newsletter subscribers went from like 30 a month to one to two a month over, it seems like overnight. like all that, 100 % of that content is like, I wanna read about something or I have a question about a book I read or, you know, it's like, it's pretty extreme there. ⁓ So the solution to that problem is starting to think about AEO or Agenic Engine Optimization versus SEO.
Tyler King (21:02)
Wow.
Right.
Rick (21:24)
⁓ I think the game is totally, totally different anyway than SEO, ⁓ in terms of what the outcome you want is, but, ⁓ I'm spending a lot of time thinking about this now, not just from a leg up health perspective, but also at my day job. And I think this is going to become a very, ⁓ SEO, like. Like kind of a sprint in this. think people are going to start talking about this a lot over the next six
Tyler King (21:27)
Yeah.
Yeah.
Tyler King (21:47)
Okay, so I think this is what you're already saying, but like the shallow version of this is Google used to be the thing that linked to me. Now I need to make it so chat GPT is the thing that linked to me. And if you're selling a good, like leg up benefits, right? If you're like someone needs a platform to manage their health benefits, like they're not gonna get that directly from chat GPT. So they might go to chat GPT and say, hey, what system should I use? And it'll work very similarly to Google. It's also probably based on similar
signals, right? Do you have backlinks and do you have good content and stuff like that? But then the whole like top of funnel stuff or like content game where it's not about directly selling the thing to the customer, it's about here's information to build trust, to get you aware of our brand, and then we'll nurture you down to the point of buying. The customer doesn't want to click through to a website. They want the answer from Chatchie BT. So there's just no point in even trying that in the AI world.
Rick (22:43)
Exactly. So it's, I think it becomes more about like getting mentioned by chat, GBT, which is further down the funnel. So like, let's say the question is what is a premium tax credit subsidy? You know, you're not going to like getting cited there for like up health as a win, but like, that's not going to lead to any sort of like Legion or brand awareness because they're not going to go look at the citations like long-term, right? Cause they're to start trusting chat GBT. then it's like, okay. ⁓ what's the next question they're going to ask? Well, are you interested in getting help finding a premium tax credit?
Um, would, uh, if so, I'm happy to recommend some local brokers. Where do you live? And it's like, okay, well, we're only going to get recommended in Utah. If we are chat, LGBT thinks we're a Utah broker and worthy of their top recommendation. Um, and so how do you get that? Which is the ultimate goal, I think.
Tyler King (23:29)
Yeah, and I can say I am far from an expert on this, but LessonWing Serum is actually doing pretty well at this. We are hearing a lot of people saying they're finding us through ChatGPT and our free trial pipeline. I'm not sure I would say it's gone up, but it has not gone down since any of this stuff. So basically people who used to find us on Google are now finding us on ChatGPT. But if you dive into that, it seems like ChatGPT primarily, at least for us,
is looking at review sites and rating sites and directories. It's not who has really good blog posts about this topic.
Rick (24:03)
100%. ⁓ that's what I've heard time and time again is that if you're, the third party reviews that you have, ⁓ are what dominate, the agent, like sort of a bias towards including you in a category. It also matters what category you're listed in and, ⁓ on those review sites.
Tyler King (24:23)
And I don't get the impression that they're saying, ⁓ less annoying CRM has 600 reviews on G2 and they average this amount and here are the pros and cons. I think it's much simpler, like keyword type stuff where, almost, we've started this customer interview project, by the way, which I won't go too deep into that because that's not what we're talking about here. But Eunice has been talking to our customers and at least a couple of them who she talked to so far were like, I found you on chat GPT. It's always the second query. It's always.
I need a CRM, what should I use? And it's Salesforce, HubSpot, whatever. And then they say, no, those are too complex. need something. And then they give more detail. And that's when we come up. And it really seems like it's just because a few reviews on G2 use the exact words that they used or something like that. So I don't think the game is get as many five star views as you can. It's like, get the reviews to say the right words more than anything.
Rick (25:15)
So that
you get associated with that pain or solutioning ⁓ when the question comes up. makes sense. So anyway, kind of wrapping up my open enrollment spiel is like consumer down due to things outside of our control. ⁓ This inbound lead content thing that I've made a living on for my whole life is going away and I'm scared about it.
Tyler King (25:21)
Yeah.
Yeah, total guess, obviously. I don't know what's going on behind the scenes there.
Rick (25:44)
And I have no solution yet, but I'm going to start thinking about this a lot more in terms of both like long-term for my own, like I think AEO is something I want to understand. And ⁓ I think we should be intentional about making sure that we're just like we were with SEO for years.
Tyler King (25:59)
Yeah. The other final thought here is like, it seems like maybe in the short term, focus more on group plans. ⁓ I think the average listener hears us talking about health insurance all the time and probably doesn't know. I barely know what you're talking about and I work with the company. ⁓ But group plans are not going up by a lot, They're getting the normal 10 to 15 % premium increase, but they never had these subsidies to begin with.
So that market should be pretty much undisturbed, whereas it's the individual people that were getting these subsidies that's totally fucked right now. So probably just stay away from that and focus on group for a while.
Rick (26:37)
Yeah, I think so. Or paid leg up benefits, right? Like, you know, it's, it's, ⁓ you know, giving people money, but you know, to go pay for their own health care is now even more valuable than buying health insurance or doing nothing. ⁓ so, ⁓ anyway, ⁓ but yeah, you're right. It's a nice thing that I'm glad we have a diversified business at this point before this all went down. What's going on with you now that I've dominated the episode.
Tyler King (26:58)
Yeah.
yeah, I got a, just a handful of little updates. ⁓ we kind of soft launched automations yesterday. ⁓ I feel like every big feature now kind of has two launches. our normal approach now is like, there's very little urgency to launch it to current customers because current customers hate change. They're very few of them are actually going to use the new feature. So it's like.
we can wait to get the whole thing fully ready to go before we ship it. But new customers who are like, this is my moment where I'm deciding if this product has what I want. If we think we're building a feature that for some people is one of their key features they're looking for, we want to ship it as soon as possible. So when I say we soft launch it, what I mean is all new accounts that sign up for Lessoning Serum going forward will have automations enabled by default as we continue to work on the feature and make it better. And then once all that's done, we'll ship it to all of our current users.
Rick (27:58)
Nice. Any learning so far, is it still?
Tyler King (28:02)
We've had some people beta testing it for a while overall. So we don't send emails, which is the obvious thing you want to do with automations. like that it's less interesting of a launch because of that, but people are getting, yeah.
Rick (28:13)
Can you can the automation
trigger his app?
Tyler King (28:17)
sorta Zaps could already do all of this. Like we don't need to trigger the zap. The zap could already get triggered. ⁓ so this doesn't really unlock anything for Zapier. the people who are beta testing it, some people have given, given rave reviews. Cause it is like, if you think every time I create a new lead in my system and I'm like manually entering them, it's like, I need to add them to a group. So they sync over to MailChimp. need to add a lead pipeline to him. I need to assign a seven day, 10 day and 30 day follow up or whatever.
Do that all with a click of a button. If you're doing that a dozen times a day, it really does save a lot of time. I think that's gonna be five or 10 % of our customers, but it's really good for them. I think of our big features right now, like I have more clarity about product strategy right now than I did six or 12 months ago. Of the three big things we're doing, automations is the one that doesn't really fit what I currently think our product strategy is. The other two do still fit, which two out of three ain't bad. ⁓
Rick (28:57)
Makes sense.
Tyler King (29:16)
But still, nice to have it done. A year and a half ago, we said there's five big things we want. Email sending, email receiving, ⁓ automations, mobile app, and Kanban. And we did email receiving earlier this year, automations is number two, and then mobile and Kanban are both coming probably in the next few months. So we'll really just have email sending left after that.
Rick (29:40)
That's awesome.
Tyler King (29:42)
Yeah, let's hope it works. I think I hinted at this last episode, but I gave ⁓ the normal six month presentation to the company. I did just want to kind of give a thought ⁓ about this, because people who have been listening for a while, you we've been doing this podcast for years. If I give this presentation every six months, this is probably like the eighth time you've heard me say this or something. A lot of times this, me preparing for this presentation,
kind of feels like a waste of time ⁓ in the sense that it's like, I have to just go up and talk for 45 minutes to the company. do think they get like the team gets value out of it if I do it well in the sense that it's kind of like a motivator. ⁓ But it, yeah, it just kind of feels like, okay, I'm just spending hours and hours and hours prepping to say a bunch of stuff that I've already said basically. This last time didn't feel that way. I actually took longer than normal.
but it was a forcing function to make me think about like what we should be focusing on. Because again, I said a year and a half ago, we set these, this kind of product strategy and we're not done with it yet. So I hadn't really like picked my head up and looked around at all. Cause I think it was a good strategy a year and a half ago. don't unlike previous, like if you go back three years, everything I said, I was just totally wrong about. I don't think I was totally wrong a year and a half ago, but there was some refinement to be made.
And if I hadn't needed to give the six month presentation, I wouldn't have taken the time to dive deep into that. And that actually led to this ICP stuff I've been talking about doing customer interviews ⁓ and giving a lot more thought into like, are the next features we should build? ⁓ All of that is a direct result of me having to prepare this presentation.
Rick (31:30)
Nice. So basically your six month company presentation is a, it's almost like a forcing function for you to reflect on what you said six months ago, what the mission, vision, values strategy are like, and whether or not you were right six months ago, tweaks, then getting basically saying, here's what's going well. Here's what's not going well. And here's what's changing.
Tyler King (31:54)
Yeah. I think like five years ago, I didn't need that because I was spending too much of my normal time thinking about the, like, there's this delicate balance, right? Where you want to give yourself space to, like, this is what retreats are for or whatever. You want to give yourself space to think big picture and all that. But once you've got a plan, you need to stop thinking about that and just go execute the plan. So I had never really practiced what I'm preaching right now until right now, but like,
saying I'm only gonna think about this stuff every six months or every 12 months and the rest of time I'm not even gonna give myself that space, I'm just gonna put my head down and do the work is probably a better cadence than what I did in the past.
Rick (32:35)
I like that. And I, we were talking earlier, I think before we started recording about open enrollment a little bit and how it's like my, my, my feeling right now, it's like, want to go fix it, but it requires a new plan. And it's like, no, let the plan play out in February. have a, like, we have two kind of planning, natural planning cases in February, in February and August, let these things play out. we will, we will fix it. We will fix the plan in February and put our heads down again.
Tyler King (32:46)
Mm-hmm.
Yeah, it's a very calm business approach. Of course, sometimes there are things that happen where like if Utah's largest health insurance agency goes out of business right now, you should probably be like, all right, all hands on deck, we're going to get those customers. But if nothing like that happens, yeah, stick to the plan.
Rick (33:18)
Yeah. they are plan and nothing has changed. Like we knew the subsidies were going away and we had a plan for it. We thought that they would get extended, but that didn't happen. So we were wrong about that. Like that's something I'll be reflecting about in February. We were wrong about that. We should have probably played, played more defense against this.
Tyler King (33:28)
Yeah.
haha
I think a lot of people were wrong about that, but yeah.
All right, another up, yep.
Rick (33:40)
Can you
just like quickly, what is your two minute product strategy? Just refresh.
Tyler King (33:46)
Yeah, so
the old one as a reminder, not that, so the old one was CarPlay, which is ⁓ when you're buying a car 10 years ago, you did not necessarily need the car to have CarPlay. Now you do. What aspects of the CRM, like we are a simple CRM. Our goal is not to have every feature ever, but there are some things that have become standard over the last 10 years that we fell behind on. Email stuff, Kanban, mobile and automations are what we decided those things are. When someone's looking for a CRM, even if they want a simple one, they still want those things.
Again, I think automation doesn't quite fit, but I think the rest of them do. ⁓ That has been the strategy. We don't know if that will, quote unquote, work or not. Time will tell. But even whether it works or not doesn't change the fact that we should not keep doing it. To continue on with that strategy is to say, our long-term goal is to have every feature, which just isn't in our DNA. So the question is, if we think we've checked all the boxes for a simple CRM for our ICP,
what comes next. And I'm still kind of trying to figure out the right way to say this, but my current language for this is first 30 minutes. It's all about the first 30 minute experience in the CRM. Some of this is the obvious stuff like basic onboarding. We're going to invest really heavily in making our import process a lot better. ⁓ And some of it is less about the onboarding experience itself and more about just making the product fundamentally simpler to use. So
Like what are the questions we get from people who have spent 30 minutes in the CRM? And I said this before, but I'll give another example of it. Like very common, someone imports their contacts, each row of their spreadsheet has a contact name and a company name. We create a contact and a company, then they go into their contact list and they see one row for a contact, one row for a company, and they say, you duplicated everything. I imported a hundred rows, but there's 200 rows in my CRM now.
We can just solve that. We can just make it so we don't co-mingle contacts and companies in the same place anymore. ⁓ So I have a long list of stuff like that, but where it's just like everything that confuses someone in the first 30 minutes, we can just make it not confusing.
Rick (35:57)
we hired a new VP of customer success at one fall. Who's amazing. I'm so much from, from him, but time to value is one of the core things he talks about in terms of minimizing, ⁓ law, like churn. ⁓ and it's a different business model at windfall, but like same, same principles apply here. And I totally support this and I've never heard you talk about this this way. ⁓ I think there's probably a lot of juice to squeeze in, your, the first 30 minutes of a customer, a customer's experience with.
Tyler King (36:11)
Mm-hmm.
Yeah.
Rick (36:26)
⁓ listening serum. That's really cool.
Tyler King (36:28)
Yeah,
there's a ton. I've heard time to value a lot before, but the way it's always described is like, the value is, so for example, what's the value of a CRM? It's like, I closed a lead I wouldn't have closed otherwise or something like that. And that normally doesn't happen for weeks or months after you sign up. So there's kind of this other thing, which is like time to perceived value, ⁓ which, so part of the focus Eunice is doing it with these customer interviews is she's talking both to people who didn't.
convert after the free trial, which hard to get on the phone with those people, easy to get on the phone with people who did convert. For the people who did, like when was the moment you knew we were a good fit? And so far what we've been seeing is for a lot of people, it's the moment their contacts get imported correctly. They haven't gotten any value yet, but they're like, ⁓ that was really easy. I get it, this is gonna work for me.
Rick (37:21)
It's maybe it's not time to value, maybe it's time to implementation. know, like implement it so that you can get start to get value.
Tyler King (37:25)
Yeah.
Yeah, cause I think everyone knows what the value of a CRM is. They don't really need to be convinced of that. They just need to be convinced that this one will get them the value they're expecting. Yeah. So, yeah, I'm pretty excited about this direction. I'm kind of impatient though, cause we still have four months of finishing up our current projects probably, but I think 2026, it's going to be the year of the first 30 minutes. And ⁓ I think at the end of 2026,
Rick (37:37)
Yeah, this thing will work.
Tyler King (37:56)
I'm gonna look back at this. We'll see, but I think I'm gonna be like, why did we wait so long to do all that stuff?
I got more updates. We got a few minutes here. Do you wanna talk about either of your topics? No? Okay, I'll just cram another one in here then. Long term, a long time kind of cultural thing at Less Annoying Serum has been everyone at the company does support. Partially this is good for like optics with customers, like look at how our developers have to do support, yada yada, we care about you. We're not a normal tech company.
Also good for internal company culture. The two teams have to interact with each other and it's good for as much as possible both sides to know what the other is going through. Support has gotten too complicated at less annoying CRM. The devs have been for a while, like in 2015, the devs were speeding up. They were helping, right? It'd be like, oh, we have a developer on support for the next hour. We're going to move faster.
For a long time now, it has been, they're probably net neutral. Like they cause as many problems as they fix. And I think we've reached a point where the CRM coaches are kind of like, I hope no dev is doing support today because it'll be better for us if they aren't. ⁓ So we have made the decision to stop having developers do support, which I feel conflicted about, but yeah, any reactions?
Rick (39:25)
I think this is one of those things you're gonna go back and forth on over the next five years. ⁓ But good. yeah.
Tyler King (39:31)
You think we're gonna change our mind?
Say more about that.
Rick (39:35)
I think, uh, there it, well, I don't know if you're a change your mind and go back to exactly what you are, but I think like ultimately devs doing support was intended to do a certain thing. Uh, customer empathy, whatever you want to call it. Um, understanding the customer, uh, understanding the deficiency of the product, um, what, what problems is the product actually solving that kind of stuff? If, if that was working, you know, to do that and you don't replace it with something else, you'll
ultimately come back to the same thing that was working. So either you're going to figure out how to do this without support or you're going to go back to support because you know it works.
Tyler King (40:13)
Yeah.
So I actually think it was also failing on the developer empathy side because what happened was increasingly developers were picking the easiest tickets to answer because they didn't know how to answer the hard ones. So they weren't even seeing like the product efficiencies. So what we're moving towards, we're going to experiment and see what happens, but like something along the lines of a CRM coach giving a one hour, it might be like showing a recorded demo or giving a workshop on like, here's this
whole area. Let me show you 10 different support tickets. They're all complaining about different parts of the same thing, but kind of being like giving more insight into where the points of friction are, but the developer's not actually directly providing support.
Rick (40:55)
Yeah, I mean the, the, you're describing as a product manager, ⁓ type function, who is basically collecting customer and prospect and market data points and summarizing it for the devs. ⁓ so yeah, I think someone needs to do it.
Tyler King (41:12)
Yeah, we are doing that. Too early to say if it's working or not, but.
Rick (41:16)
And it's the customer support version of that, the right, is that the only angle, right? Like perhaps there's a marketing version too, like why are people not, you know, converting on, on, free trials? ⁓ but is that support?
Tyler King (41:29)
So do I care
about them knowing that? ⁓
Rick (41:32)
If the, if the first 30 minutes is the focus, don't you want them to know about that?
Tyler King (41:36)
This is gonna go against how a lot of people think about their, I think a lot of companies are like, I want every person on my team to be their own entrepreneur and come up with their own ideas and solve all the problems themselves. like, I've never been in an environment where it works like that. So if that's actually a real thing, that sounds great. But what we do is I decide what we're gonna work on. I get it designed with our designer, Tory, but like I'm overseeing to make sure it happens. And then I give it to the developers and they just implement whatever I tell them to. Yeah.
Rick (42:04)
The only, the only thing that I'll say, cause you're not saying it is you do get a lot of input on what people think are the priorities before you make your decision. like people feel like they're, they had to say, even though maybe you're making the decision.
Tyler King (42:16)
Yeah.
Yes, but almost all that input is coming from the customer facing people, not the developers. ⁓ There are a couple of developers who are more proactive and more involved. if they are interested in this, I want to absolutely encourage them. So what I didn't mention, me and Robert are continuing to do support because we're more engaged in it. The other developers though are for the most part, I'm maybe painting with too broad of a brush, but they're much more like, give me some designs and let me code.
Rick (42:45)
Yeah.
Tyler King (42:45)
They don't want to be talking to customers.
Rick (42:46)
I mean, what you're talking about here is specialization fundamentally. And, ⁓ you know, it seems like that's you're specializing and that makes sense.
Tyler King (42:55)
Yeah, okay, absolutely that's the right way to frame this. That is a thing time and time again, as we specialize, there's a lot of upside to it. And it also does feel like you lose a little bit of that magic from the early days of the company. Cause we're not, we're not bigger. We don't have more employees than we did five years ago, but we are more specialized. Yeah. Okay. Well, I may or may not update on if I, if you don't hear any updates on that, assume it was good enough.
Rick (43:12)
Yep. Yeah, there's trade-offs.
I
did.
Tyler King (43:25)
⁓ I think that's it for me.
Rick (43:27)
Cool. ⁓ well, thanks for letting me vent a little bit about leg up health struggles. ⁓ I think we were due for a tough stretch. ⁓ I think we had a really good year. Yeah. Yeah. So, ⁓ I think, ⁓ I dunno, I'm, I'm just, I'm trying really hard not to react to it. I'm trying to just like reassure JD saying, Hey, like you're w we did our, we did our goals, like do the best you can. Don't let off the gas, execute the plan and we'll, you know, if you see opportunity to shift the plan.
Tyler King (43:36)
Yeah, the beginning of this year went too well.
Rick (43:57)
Let's do it, but like don't overthink this.
Tyler King (43:59)
Well, let's reference back to an earlier episode this year where there was a question of like, what should the goal be? And ⁓ it was like, okay, maybe there's a stretch goal of like, what could we get to if everything goes right? But that's not what the company needs. The company doesn't need to hit that goal. And so you made the decision to set a more conservative goal, make it a little calmer. And that's why right now you can say, I'm disappointed by open enrollment, but it's okay, as opposed to like, I'm losing sleep over this.
Rick (44:29)
Yes. And I, what I need to make sure, cause I think we have the benefit you and I have being pretty distant from the business day to day. And I just need to make sure JD is able to do that even though he's in the grind. So that's an accident for me. Well, if you'd like to review past topics and show notes, visit startup to last.com. We'll see you next time.
Tyler King (44:39)
Yeah, yeah, good point.
See ya.