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Index/Startups & Founders/Startup to Last
Startup to Last artwork

A new cross-sell opportunity

Startup to Last · 2026-10-29 · 42 min

0:00--:--

Key moments - from our scoring

Substance score

50 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality10 / 20
Guest Caliber11 / 20
Specificity & Evidence13 / 20
Conversational Craft7 / 20

Lesson Wing CRM faces a shifting market dynamic revealed during the host's six-month internal presentation. While the product team has been executing exceptionally well - shipping eight meaningful features during Cupholder Week and building sophisticated internal tools like an automated bug-fix system using AMP orbs and Claude Code - the underlying demand for CRM software appears to be declining. Using LLM-based analysis of cancellation messages, the host discovered a troubling trend: customers citing self-built CRM replacements in Notion, Airtable with Zapier, and especially Claude Code have surged from roughly one per month historically to nearly daily occurrences in recent months. This isn't a reflection of product failure; rather, it signals that generative AI has lowered the barrier to DIY solutions so dramatically that traditional SaaS CRM may face secular headwinds. To address this, the host has reframed the company's 30-year North Star: ensuring current employees can make their adjusted-for-inflation salary and retire, which requires protecting the $4.5M annual revenue while hedging through inversely-correlated business initiatives. The episode explores whether businesses can survive in a world where code becomes commoditized, touching on Cal Newport's argument that LLMs have only demonstrably improved at computer science, cybersecurity, and math - not universal intelligence.

Key takeaways

  • →Claude Code-driven DIY CRM replacements are now a daily cancellation reason, up from roughly one monthly, suggesting AI commoditization of core SaaS features is accelerating.
  • →Building a bug-fix automation agent using AMP orbs and webhooks proved feasible, but revealed that stability may matter more than shipping velocity for financial services tools like Lesson Wing CRM.
  • →The company's 30-year goal shifted from scale and dominance to ensuring every current employee can retire at inflation-adjusted salary, requiring both defensive moves to protect $4.5M revenue and asymmetric hedges against AI-driven market disruption.
  • →Cupholder Week - a fully-blocked week for shipping quality-of-life improvements with AI assistance - yielded eight meaningful features that were previously thought too large, suggesting AI-accelerated execution can solve backlog problems.
  • →CRM demand appears to be declining structurally, not due to Lesson Wing's execution or product quality, but because the cost of entry to self-service alternatives has collapsed.

About Startup to Last

Hosted by Rick Lindquist and Tyler King. The show scores 68.5/100 on substance across its analysed episodes. See the full show profile.

Topics in this episode

bootstrappingClaude CodeNotionCal NewportSaaSMCPs (Model Context Protocols)softwarefoundersAMP orbsAirtable with ZapierBug-fix automation agentsCupholder WeekLesson Wing CRMAnthropic IPO hedge

Questions this episode answers

Why are customers canceling Lesson Wing CRM specifically to build their own with Claude Code?

The barrier to entry for DIY CRM solutions has collapsed with Claude Code and AI agents; customers who previously would have bought a SaaS product can now vibe code functional alternatives in Notion, Airtable, or as standalone apps, making the purchase decision less necessary.

How does Lesson Wing's bug-fix automation tool using AMP orbs work?

A CRM coach creates a bug card in Notion and triggers a webhook that spawns a dedicated orb (cloud-hosted instance of the app); an AI agent fixes the bug and pings the coach to test; the coach approves or rejects, and a developer then either ships or reviews the fix, reducing dev review time significantly.

What is the new company North Star for Lesson Wing CRM?

To ensure every current employee can make their inflation-adjusted salary and retire within 30 years, requiring protection of the current $4.5M annual revenue and hedging against potential AI-driven market disruption through inversely-correlated business initiatives.

What did the host discover using LLM analysis of cancellation messages?

Categorizing cancellations revealed that the baseline of customers building their own solutions in Notion or Airtable (roughly one per month since 2020) surged to approximately eight two months ago and nearly daily now, suggesting rapid adoption of AI-powered DIY alternatives.

Why does product execution matter less if the market is declining?

The host shipped exceptional work over two years - including features before Claude Code existed - yet the business plateaued for five years, indicating that declining CRM market demand from AI commoditization is a structural problem that superior execution cannot solve alone.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

The episode contains a handful of genuinely useful operational insights - using an LLM to categorize cancellation reasons, the rising 'vibe-coded CRM' churn signal, and a concrete cross-sell hypothesis targeting gmail.com customers - but they are buried under roughly 10+ minutes of oyster anecdotes, Charleston small talk, and unfocused AI doom-looping that dilutes the useful content-per-minute significantly.

I used an LLM to categorize all these cancellation messages and group them into categories. The category wasn't AI. It was who canceled because they built their own.
We have a thousand users in our free trial uh pipeline right now. Four hundred of them have an at gmail.com domain name. Can we just email those 400 people and say, hey, do you want a real domain name for your email? 50 bucks a month.

Originality

10 / 20

The most original contribution is the founder presenting actual longitudinal churn data - going back to 2020 - showing the 'built their own' cancellation category growing from ~1/month to near-daily, which pushes back on the widespread VC/Twitter consensus that no one vibe-codes a SaaS tool; this is a lived, data-backed contrarian observation. The rest of the episode recycles well-worn AI displacement discourse without adding much.

there is this very low baseline for the last for I I went back to 2020 of people like. I'm doing it in Notion. I'm doing it with Airtable and Zapier. But we're talking like one per month or something, right? And then three months ago it was like four. And then two months ago it was like eight.
the number of people canceling their accounts because they vibe coded a CRM in Claude Code. This thing that all these big brain geniuses on Twitter are like, It's never gonna happen. No one's gonna vibe code a SAS tool.

Guest Caliber

11 / 20

The primary speaker is a genuine operator running a real bootstrapped SaaS ($4.5M ARR, 25k users) and speaks from actual company data rather than theory, which is valuable; however, this is a two-host format with no external guests, and the second host contributes little beyond light affirmations, limiting the depth and breadth of practitioner perspective on offer.

we've got 20 minutes here. Um I think these are two different topics. One is what do we do with less annoying CRM? One is what's the hedge?
If my goal were just to do that for myself, there's a very clear path, which is lay almost everyone off, pay myself two million dollars a year while the sun is shining, and I can retire if even if the business is gone in five years

Specificity & Evidence

13 / 20

The episode is notably concrete for a conversational format: real revenue figures, user counts, team sizing, cost-per-hour for CRM coaches, gmail.com segment sizes, and a longitudinal churn trend going back to 2020 all ground the discussion in actual data from a real operating business rather than hypotheticals.

if you look at the fully loaded cost of a CRM coach, it's like a hundred bucks an hour. Like we'd have to charge a hundred bucks an hour to our customers
we've got 25,000 ish users. How many of them need a VoIP product?... four thousand existing customers with at gmail.com addresses

Conversational Craft

7 / 20

The episode is functionally a monologue by one host, with the second offering almost no substantive follow-up questions, no pushback on claims, and only surface-level prompts; there is no external guest to probe, and even within the co-host dynamic the conversation rarely sharpens an idea through genuine interrogation.

what's your meaty topic?
Yeah, yeah. No, I makes makes less sense.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

less26hedge18saying15better14annoying14customers13back12oysters12five12hundred12code12idea12true11podcast10three10real10

Episode notes

In this episode, we talk about a new service Less Annoying CRM is going to offer to its customers.

Full transcript

42 min

Transcribed and scored by The B2B Podcast Index.

What's up, Tyler? No. I know. I'm sorry.

My schedule has been insane. I went and saw J D and then I was I saw you and then I I saw um I went to uh see my family in Charleston. Uh then we had our anniversary, so it's we're back on the the podcast train. Well, and I think we postponed four times.

One of them was me, cause Sydney had strep throat. Um, so yeah, we we both sharing some of the blame here. So to our three listeners, thank you for sticking with us here. But I think we got a lot to talk about now.

Yeah. dad. I don't know who the third is. It's probably you.

Yeah, I do I do I do listen to to every episode. Um but yeah, okay, so any any uh just personal updates from Charleston or anything? No, just love Charleston, love the beaches there, love the food. It's good food.

I know Shelly didn't love it. yeah. went right before you did and came back and was like, I don't get it. Yeah, so shrimp and grits, I had it like three times uh from life.

There's a one restaurant on Isle of Palms called Acme that has the best shrimp and grits and loved it. I got a funny story for ya. Um Do you like oysters? Raw?

All right, so my dad came down and we we went went to this restaurant and we hadn't had oysters yet on the trip and Sable and I love oysters love love oysters. Um so we get, you know, a dozen oysters. And I I had forgotten how much my dad likes oysters too. So we put we put away a dozen.

We order another dozen. Then we order two more dozen. So we're we're at like forty 48 oysters. And Oliver Oliver, who's my five year old, is like, Can I try one?

And he eats an oyster. And then he's like, he swallows it without chewing it or anything. And he's like, Okay. and then he just pounds five of them.

Wow. 'Cause I feel like that's one of the slimiest, like least kid friendly foods that at least in America that we eat. Wow, good for him. yep.

So he he and then every restaurant we went to after that it was like, Hey Dad, do they have oysters here? And so we ordered we had probably another hundred oysters by the time we left. It's it was not healthy. let me gripe about oysters real quick.

I don't hate them or anything. They're fine. But A, like it's all about what you put on them. Like it's just a it's a vehicle for yeah.

Um, but B, I hate the way they are marketed on a menu where it's like, oh, this is Fallen Bay oysters. That's the bay they're from. And I'm like, that means nothing to me. Like, you're just telling me the name like imagine if they sold fish that way.

If they were like is it small? Is it sweet or is it salty? here are the GPS coordinates of where we got this tuna. Like that doesn't help me understand what this dish is gonna be.

I hate it. Well they're also like a I mean, you know what an oyster does, right? Like it's like a filter system. Like if you put an oyster in a dirt in dirty water, the water gets clean.

Where does the dirt go? Yeah. No, I think pearls are oysters. Yeah.

That that's like uh anyway, okay. This is now a seafood podcast. So anyway, strip and grits was my is my m favorite meal from the South that uh Acme does the best version of. and then uh we we had so we had a good time and we came back.

Um JD's got got full control over leg up health right now and he's um he's adopted he's he's he's taken the next sort of leap with using AI in his day to day and it it really we've always talked with technology When we first started the podcast in the no code days about one of the one of the bets with Leg Up Health being the idea of like it'll always there'll always be some some concept of a human in the loop with with financial services and um building a super agent, you know, uh Iron Man, you know, five X, ten X agent and with AI tooling used responsibly.

I think that's even more po more and more possible. So it's cool to see him uh doing that and uh being on top of everything. Yeah, for sure. What's going on with you?

Cool. Well, lots of stuff. Like, before this got delayed, I was like, this is gonna be one of my most like, I wanna just take over and talk about all my stuff for this episode because I had so much. And since then, uh, it's been completely replaced with a whole different set of things.

We the stuff I don't want to talk about anymore because it's like overshadowed, but we had Cupholder Week, which is basically where we take a week off and cancel our meetings, everything, everyone's in office every day. And just like shipping like the little quality of life improvements for customers, but we shipped I think eight like nice like some of these were actually pretty meaningful features that customers have been asking for for years and we keep telling them it's too big of a project.

And then with AI, we we get it done in a week. Um so we had that. Uh I wanted to talk about AMP orbs, which are the Like that's the coding agent we're using we're using now is AMP and orbs are their like online virtual machine thing. I slacked you about this, but like talking about the new, like a cloud environment for running for for coding and running the actual dev environment, which is huge, which then led to my project during Cupholder Week was I code vibe coded uh like a bug fix automation tool.

So like sorry, I'm I'm I know I'm running through this stuff quickly, but Like that's a lot of progress. And I don't care about any of it anymore. Um, so but I'll I'll spend a minute on this. So um it's all our workflow for years has been uh most bugs are reported by CRM coaches.

Like a customer reports it to support, the support puts it in Notion as a Notion card on this bug fix board we have. Uh and then a developer triages it, assigns it to a dev, and then the dev every Wednesday is bug fix day, the devs go in and fix everything. But now the f yeah. Notion, that whole workflow?

So you don't use like a Jira or Linear for ticketing, you use Notion. rebuilt a Jira linear type thing in Notion. So it's it's less like specializ you know, like it doesn't have all the quality of life improvements that a linear has, but it's I tried linear and it just doesn't work the way my brain works. So it's more tailored to us, but it's that type of idea.

But it's built on Notions AI platform. So like you can use all the Notions features. Never used any Notion AI tied to this. Yeah.

I mean, we I built this years ago. Um we we we use a lot of like agents through an MCP to spec out cards and stuff, but not Notion AI. Which is maybe a theme I want to talk about later. Um but yeah, so now the CRM coach creates the bug card and pushes a button in Notion.

That calls a webhook to our so an orb is like a single coding thread. Like it it's like a claud code thread, but it also hosts the website. So each orb is a different instance of our w of our whole app hosted in the cloud. So every single bug creates its own orb, then the agent fixes the bug as best it can, and then pings the CRM coach and says, I think it's fixed.

Can you test it in the orb? The CRM coach tests it and either either gives a thumbs up or a thumbs down. Either way, it still goes through a dev, but like if if the solution. Yeah, if the solution is approved by the CRM coach, all the dev has to do is just glance at the code and be like, you know, sometimes it's like this is five thousand lines of code, that's wrong.

Sometimes it's like, this is ten lines, nothing looks horrible, ship it. Like I don't even need to do anymore. So like an agent at some point? Yeah, I think probably.

if I'm being honest, I think the biggest hurdle to that is cultural, not technical. Um But at the same time, I'm there's for a business like Less and Wing Serum, I do think stability maybe matters more than like shipping velocity, arguably. Um this is another theme kind of connected to something I want talk about later. Yeah, and these companies that are like vibing real, real hard, they are putting out a lot of shit.

And If what you want is the max features, like I want to be on the cutting edge, I just want all the functionality and I can handle some rough edges, then that's fine. But I don't think that's the business we're in at Lesson Wing CRM. Um but yes, I think that I I don't think the full thing can fully get replaced. Sorry.

If the CRM tests a fix and we could probably have an LLM that's like, here's how you decide if it needs a human review or not. And it's like, If it's a simple front end change or whatever, like we could probably codify here are the the things that could be done automatically. But it's already like I don't think it's like a huge game changer because the reality is before the the dev was just telling their agent to do it. It's not like the dev was doing it by hand.

It's just like the the agent does it and the CRM coach can approve it rather than the dev asking their agent to do it, sitting there for twenty minutes while it's doing it and then testing it themselves. It's it's a slight improvement. No, I get it. It's great.

It's awesome. it is the first time I've ever built like you've talked a lot about agents on this podcast. I've talked a lot about like well, coding I've talked about coding agents, cloud code, et cetera. You've talked a lot about like I built an agent in Slack to do whatever.

This is the first time I've built, I think you would call it an agent. Like I've I've built something with AI to automate a thing at Less and Wings Serum. Um, not much. Like I It's i honestly in a way that I find problematic.

I I find it very troubling because it's like there has to be something hard that that humans do and I I'm not seeing it. But um I just I I haven't seen any of the code. I don't even know. I think it's in TypeScript.

I'm not positive what programming language it's in. uh AMP has the wet like handles the webhooks and all so I'm just talking to this one orb, and when something breaks, I just say to the orb like, Hey, it broke and it's like, All right, I fixed it. Um that's the level of I'm just I like you you could one hundred percent have done what I did here w without having to learn anything. Yeah.

Um also during Cupholder Week, I vibe coded a bunch of our a bunch of marketing reports. Some most of these we already had a version of it, but like, you know, back in the day, like you had to hand code any internal report, and they're like they're wrong. Like there's no right way to do certain statistics stuff. It's like, well, what do you want to count as churn?

And like if you're looking monthly over a year and someone churns between months but then pays the next month, do you count that as churn and then reactivation or you know, like there's lots of judgment calls. But anyway, these reports were straight up bad. Uh pointed AI at made them all better, uh made some new ones we didn't have before. Um Another update that is in in this quick summary.

I have something here that says found out why our biggest account is shrinking. Uh since then they canceled. So we lost our biggest account. But th this is one we well, so we had two really big accounts by our standards, like in the you know, mid-hundreds of users.

Uh one of them told us a year ago they're canceling. Since then, they've almost doubled in size and they have not canceled. Uh the other one that was the biggest one. Shrunk and shrunk and shrunk and shrunk and I think the whole company went out of business, so they're gone now.

Um Yeah. That's my quick updates before I get into my meaty topic. Yeah. what's your meaty topic?

Um okay, here. Let me let me clear out all these topics from our notion board so I don't get distracted here. I'm just knocking them out. Um okay, so I gave uh as as you know, every six months I and the other like the leadership team at the company gives a six-month presentation to internally at Less Knowing Serum to the employees.

Um sometimes this feels like a real drag on my time. It normally takes like a week of full-time work to. Prepare for this, and oftentimes I'm like, I don't know if it's worth the week, but sometimes it's really valuable because like a lot of times I don't know what to say. I'm like, you know, we've got a plan where X we're only halfway through the plan.

So it's like, what am I gonna go up there and say, let's keep doing it? Like, that's not a very rousing speech to give. So I always like have to think about what I'm gonna say. And in doing so this time, I I often have to go into the I just it it's a it's a forcing function to make you like.

I'm gonna go run through our numbers real quick and make sure all the things I'm saying are actually true and all this. And um one of the things that stood out to me is this narrative I've been saying for years on this podcast and internally at the company is like we're plateaued and nothing we ever do matters. We're not going down, we're not going up. We're kind of going down.

It's so minor, like when you zoom out, it still looks exactly like a plateau. But and and there's ups and downs throughout the last like we've been plateaued for five years. There's ups and downs. Our down right now is not any worse than the other downs we've had in this period.

So it's very possible we just bounce back up, right? but then I was like, I wonder if I can figure out why. And of course, you gotta think AI. Can I find any evidence of that?

And unfortunately, the answer is yes. I can find evidence. Um the most concrete thing to point out, even though the numbers are very small. Is like the number of people, well, A, the number of people asking for an MCP, which we kind of have, but we need to build a better one, skyrocketing tons and tons.

That's no surprise to anybody. Uh, and we already have that prioritized once our current projects are done. Um, but the number of people canceling their account, not because we lack AI features, because that can be solved. We just build the AI features.

The number of people canceling their accounts because they vibe coded a CRM in Claude Code. This thing that all these big brain geniuses on Twitter are like, It's never gonna happen. No one's gonna vibe code a SAS tool. And I maybe you can go back a year on this podcast and hear us saying that.

I don't know. I don't think we ever said it with that level of confidence, but uh people who say it's never gonna h for sure. yeah replace uh a CRM. But but I don't know that we ever said it about and even that it's interesting you say that because the way I presented this in this presentation is like we've had I I didn't say who said they're replacing us with AI.

I s I said who you know, I I used an LLM to categorize all these cancellation messages and group them into categories. The category wasn't AI. It was who canceled because they built their own. And there is this very low baseline for the last for I I went back to 2020 of people like.

I'm doing it in Notion. I'm doing it with Airtable and Zapier. But we're talking like one per month or something, right? And then three months ago it was like four.

And then two months ago it was like eight. And then I mean it's it's every I think basically every day now, or pretty close to it. some of those are free trial users canceling. It's not all like current, it's not at all churn, but the Yeah like they're the ones in the market.

Well, and it also strongly implies if if pe it's kind of weird to be like, I signed up for a CRM trial and I canceled because I don't need a CRM. Like how many people didn't sign up for the trial in the first place? Um, and that's another thing. Our free trial pipeline is down, our churn is up, like everything kind of points to not that we're doing anything wrong.

Cause I a different thing I did in this presentation is I worked went through our execution since 2020. What did we ship this year? What did we ship this year? And on and on.

The last two years have been unreal. Like we've and not just because of AI, like even before Plawed code came out. We were our product has gotten so much better. We've been executing, we've been doing our job.

Uh, and it just doesn't matter. Like the demand for CRM, I think, is definitely declining, is what I'm seeing. Um, still a major question of like, there, there, I could tell a number of stories for why we're gonna be fine. Like, just because the demand's declining doesn't mean like the fact that we're the cheaper option, the fact that we could do this or that, but like we.

The market is still so, so, so big that I'm not saying there's no hope for us, but when we're already a plateaued company for five years, it's not an encouraging thing to see. And I I I you started this conversation with like something about a thirty year business, right? Like yeah. And I I I just I I to me, like, have you done the like what the world like not not even thirty years, but like ten years from now, what does the world look like?

Like, have you done that deep thought? I mean we're all everyone's I have not like like I have not thought ten years ahead. I have not. have like panicking in the shower, not like uh not like I'm a consultant putting a report together on it.

Um But the thing the reality is I don't even think it's a useful I think it's a good question for you to ask. It's not useful to spend a lot of time thinking about because the answer is it could go off in any direction. Uh i i it's so many things are possible over the next ten years. I d d I would imagine that if if if you thought about this uh enough, you could get to a pretty strong sort of hypothesis around what is likely to be true, what's likely not to be true, and what is you know, what um as a result of what's likely to be true would still maybe be be useful.

Yeah. thinking about that. Uh I d uh what what maybe the reason I'm like kind of hemming and hawing here is I what everyone wants right now is to say, what will humans still w what what will the AI need the human for ten years from now? A thing you hear a lot of people say is like there will always be a role for humans.

AI can't like creativity, whatever, blah blah blah. It's bullshit. Like I I mean it might be true. But people say it with this confidence that like AI could never make a great song.

It's like AI can now make a great song. Like and then they're like, Yeah, but it's not new, it's derivative. And it's like, I'm I I'm a musician. I used to be in bands, like never like that successful bands, but like r playing gigs and writing real music and like recording at a professional studio.

Um the way a real human makes music is they listen to a bunch of fucking music and they get inspired by it, and then they like mix shit together. in their own way and like AI can do it. Not only can they do it, they can do it in the exact same way a human can do it. And the people who are d in a much broader and more influenced way.

Like it's it's like it's still something to be said for like are the the claim that humans are just gonna listen to personalized AI generated music and no one's gonna be listening to the same music, I'm not sure I buy that. I do think there's like a shared experience and like this song is really popular right now. But does that song have to be written by humans? I don't see any reason why.

I mean I want it that to be true, but is it? I don't see why it is. It's not clear to me that humans will be needed at all. But that's not a useful thought.

What do you do with that, you know? So I do have a thought on the I don't want I know where sp I Here's my thought. I listen to a podcast. I don't know what to talk about right now.

I listened to a podcast with Do you know who Cal Newport is? Yeah, I I do too. What I don't know it's a podcast that probably it has some really good people on it, but also some some jokers. Okay.

I don't know if he's credible or not. i so let me caveat all of this. But he made a claim that I found at least encouraging, which is he was like, if you look at like it feels like AI has gotten so much better over the last year. And then like dot, dot, dot, therefore it will replace all human intelligence.

And he's like, if you look at it, it has only gotten better at computer science, cybersecurity, and math. That's it. Um and he has this whole I think this was on the um Prof G markets, maybe I for I forget where I listen to this, but he has this whole thing being like, It will be very good at these things, it will keep getting better at these things. That you should not interpret from that that it's going to get better at everything.

And there will like other f other models, other technologies might. It's I he's not saying it's impossible to have AGI, but he's saying like LLMs by themselves will not be will not fully replace humans at everything. That's his claim. But I I still just struggle to under anyway, sorry, I'm I'm doom lipping here, but like I am going through that exercise right now of in a world where code is free, yada yada, like what What would a business even do?

And so that's what the the the six month presentation got into was so A, like, okay. High level, why are we doing any of this? Like we need a we need a North Star here. And I think I've got more clarity on that than I have had before.

Like or before it was like at one point it was, I want to get rich, I wanna be a billionaire, I wanna change the world, I wanna replace Salesforce. Like obviously it's been years since that. Um What it is right now is I want every current employee of lessoning CRM to be able to make their current salary adjusted for inflation for the next 30 years and retire. Um that's the goal, I think.

If my goal were just to do that for myself, there's a very clear path, which is lay almost everyone off, pay myself two million dollars a year while the sun is shining, and I can retire if even if the business is gone in five years, I've made enough to retire. I'd rather go down with the ship. Let's do it. So we're The goal is how do we get less knowing CRM so that every current employee that wants to can retire here?

One level down from that. So what do we I'll break into two categories. To achieve that goal, there's no question our current business is the most important thing. Even if we think there's a 80% chance that AI makes it irrelevant well before that 30-year time horizon, whatever the other thing is, we're not gonna make it if we lose that four and a half million.

in in revenue that we got now. So it's like top priority is protect and ideally not growing is maybe unrealistic, but like protect and maintain and help less annoying thrive as much as possible. So that's one part of it. That's what we've been doing this whole time, but I have new ideas on how to do that.

And then the other one is hedge. Like maybe less annoying will be good for 30 years, but if it's not, we've got to have some other seeds planted somewhere else. Um so yeah, yeah. D diversify But like in a perfect world, like like a true hedge is inversely correlated with the original business, right?

So we could just have five different businesses going, but the the same thing that kills less annoying serum kills the other four. That's not good div maybe you would say that's not diversification at all, I guess. Anyway. Yeah, but you're looking for a an asymmetric an asymmetric uh risk adjustment on the business that is basically the opposite of the opposite risk of less than CRM.

Yeah. Bracken had a very funny this is a joke, not something we're actually considering, but he had a very funny, like, what is the most pure hedge we could do? And it's we have about a million dollars in our like non No, better than that. Take a million dollars, invest it in Anthropic's IPO.

Now, I don't actually believe in anthropic. I think they are I do I do not think they are going to be a good investment. So that's that's a bad idea. But like that's what I mean by a true hedge.

Uh I Think there's a good chance five years from now, anthropic's not worth very much. It could go the other way, but any anyway, but that's a true hedge where it's like if we think Claude specifically is what's gonna kill less and wing CRM, invest in Claude. I I know, yeah. But that highlights the idea of a true hedge, right?

Um so you know, we've got 20 minutes here. Um I think these are two different topics. One is what do we do with less annoying CRM? One is what's the hedge?

and I pitched a few different ideas to the company, and then I met with every I've met with all but one person so far. have my last meeting right when we hang up here. And then I'm gonna kind of put it all together and figure out what's the plan. Um we can, if you want, we can shift and talk about something else.

If we're gonna dive deep into one of these, I'd like to dive deep into the less annoying CRM. Yeah, yeah. So so maybe can we fly up high for a second and just any like feedback that you've gotten from team members that you can share around like the concept of what you're talking about? Like is it pot is it is it well received?

Is it negative? Is this like scary? Um it's been well received. Uh I would guess there is a fair amount of fear, but I have not been told that.

Now so I said in the presentation, I said, I I got one rule for you all. You have to come with yes energy, not no energy. No energy is saying, I'm looking for reasons not to do this. I'm operating out of fear.

I'm when a new idea comes up, I'm gonna point out all the reasons it'll be hard or it won't work or whatever. Yes, energy is saying we're gonna do something. The question is, what's the best thing? And everything that gets suggested, we're gonna try to come up with the best version of it possible.

And then we're gonna compare them all apples to apples and pick the best one, or two or three of the best ones. So I kind of said to everyone, like, I I do not want negative energy here. Don't even try that. So maybe that's why nobody said fearful stuff to me.

Um, but no, everybody agreed that a hedge makes sense. I don't think a single person dissented. Uh To different degrees. I mean, definitely some people were like, let's not forget the main business here, right?

Which I absolutely is true. But no, I don't think a single person said. Like they understand that what I mean by a hedge is probably some small group of employees, which would include me most likely, basically start a new startup within Less Annoying CRM and like separate from the rest of the company at least for a while. Um, it would be a big, big change.

I don't know if they understand just how big of a change it would be, but like everybody was like, Yeah, I agree that we should do a hedge of some sort. That's good. I think it's basically set in stone we're gonna do something, if not more than one thing. Honestly, the thing I'm most excited about that came out of these one on ones was what I think is a very good idea for less annoying serum itself.

Like, not good enough that I'm like, we're gonna get back to growth, but good enough that I'm thinking this could extend our runway significantly. Um do you want me to get into that? Yeah, I'm just you're ki what you're kind of framing less annoying C R in this case is like it's an annuity. How long can you make it go?

Yes. With the understanding I could be wrong about all this. There's upside. I'm I'm not like completely disregarding the possibility that things go well, but I think you gotta prepare for the worst, right?

Yeah, yeah. No, I makes makes less sense. Um so this the I here's the idea. This is kind of merging together multiple pe what multiple different ideas from these one-on-ones.

And it's gonna sound similar to something I've said before on this podcast. Maybe I just didn't okay, whatever, I'll get into it. No, I won't get into it. I'm gonna preamble even more.

Uh remember like two years ago I was talking about VoIP, or I don't know when it was, but a while ago. It's not VoIP, that's not the idea. But if you recall what I said then The idea of building a VoIP product and selling it to our customers is like it's a cross sell. We've got 25,000 ish users.

How many of them need a VoIP product? They trust us. We could sell it to them and make whatever. Just like increase revenue per use.

Like, I think I'm past the point of thinking we can increase the number of customers. We've been trying and trying and trying. It's not happening. But can we make more money per customer?

And VoIP was at. Then in VoIP, I was looking at the numbers, and at the time the numbers looked a little better. And we were saying, actually, we've got a good number of free trial users. I think if we can just get that conversion rate up a little.

Let's let's put that on hold and go try to convert our free trial users better. And it I said at the time, if that doesn't work, let's come back. Whether it's VoIP or something like VoIP, it's a cross sell, right? So I think I'm I'm remembering that now and I'm back in that mode of like, let's try to sell something else to our current customers.

And then the question is what? Pause, hold on to that thought. Separate thing, the number one biggest opportunity at less annoying CRM, or the the number one thing we should do is figure out how to make money off of idle CRM coach time. Hm.

You have excess capacity. excess capacity, if we were any other business, we lay off three CRM coaches and I'm not saying it solves all our problems, but like quite a bit, like I mean, unless things get a lot worse, but and potentially frees up cash flow for hedge hedge investments. Yes, absolutely. So it's kind of like I I I'm not gonna I the reason I'm willing to say the word layoff so freely here is because it's not gonna happen.

We're not gonna do that. Again, we'll go down with the ship if that's what it takes. But we're sorry, let me rephrase. If the business is actively failing and we have no other choice, that we would, but like we're not anywhere close to that.

Um but it's like, how do we this is just a big financial weakness in the company is we're paying a team of eight people really good money when we we could get away with a team of four. A team of six would be fine. We have eight. Um so what do we do with that excess capacity?

So these are the two thoughts. We need to cross cells yeah. and if you invested more aggressively in AI uh support, potentially you need fewer even fewer CRM coaches. Yeah.

uh I have so many things I didn't even have time to say. Michael, the head of customer service, built this thing we're calling Scribe during Cupholder Week. We previously paid for a tool that would draft emails in front for us and then a CRM coach would review it and hit send. Um the the tool was resolved 247.

I have good things to say about it. I liked it, but the reality is we do customer service in such a unique way. No off-the-shelf tool is built for us. Um, Michael, a non-programmer, in one week, vibe coded something that works quite a bit better.

I'm not saying it would be a better product to sell to someone else, but for the way we work, how personalized, how tailored it is, it's the CRM coach is like, this is much, much better. Um, yeah. It's cool, but it's that's scary. Yeah, it's it's it's a it's a it's a it's the threat to s less C C R less annoying C RM in a box, but it's also very cool.

But also like when you talk about the hedges, you're like, yeah, build an AI tool. Well that resolve is an AI tool and w we just vibe coded it. Like where is the moat anywhere? But it's very cool.

Um, yeah. It's I mean, it's honestly really good. It writes the the main com yeah, go ahead. I saw you said moat.

I saw a uh post. I can't remember who wrote it, uh, but like the end like the the his point was like it this is the end of moats. There are no moats. You can't you have to c yeah, I I didn't read the article, I just like I was like, yeah, like I it's but the point is like it's it's hard to build defensibility.

and it's you have to s like the the other th trend that's like this is that that I'm experiencing at w at Windfalls is You have these situations where in a at a in the in the old days, maybe maybe you you set an org chart for eighteen months to three years and you're like ran ran the business a certain way. That doesn't like that the li the the the the lifespan of an org chart in this world is three to six months. And if you're not rethinking what people are doing and who reports to who and how you operate the business, like the whole thing breaks.

What all the AI optimists say is they're like, yeah, every technology ever, people have been worried about this. Um, and there is a period of creative destruction where things like businesses go out, go under, and yeah, organizations have to be restructured all the time. But a few years later it it steadies out and there's actually more jobs afterwards. And that's whatever a lot of people are saying that about this, but like, do you not see a difference between railroads and general human intelligence replacement?

Like yeah. Uh the the other the like the other there there's like three very similar themes here. One is the org chart, sort of how you operate the business, acceleration of like it's it's just like the sustainability of it. Like you have to re self self uh sort of uh disrupt um the mo the moat piece.

Um another another example of it is a talent acquisition. Um like the the the the uh will the the value of an a player uh versus the risk of a B C D E player higher. It's just like skyrocketing. Like and and it's like the just everything I feel like the the just the pool of opportunity to win is shrinking.

Uh that feels like a temporary state where it's like you need it f like it's it's not like it shrinks and then stays there. It's like every every time it gets better it shrinks more and more to the point of like there's one person saying, Here's what I want, you know? and that's that's kind of like what it feels like uh just just another another version of this is the uh w widening wealth gap. You know, like the it it's but it's it it does feel like that's what's happening is like there they're the the the the competitive advantages opportunities are so few, uh that whoever controls access to the superintelligence actually is owns everything.

Yeah, a hundred percent. So okay. But yes. I'm I'm terrified of all this.

Um but so uh making good use of excess CRM coach time, big opportunity, cross-selling something to our current customers, big opportunity. The obvious place this leads is can we offer some sort of service to our current customers rather than a product? Our devs can keep working on what they can work on the hedge, they can work on our normal stuff and the CRM coaches can go sell their time. Uh so that's like The direction I'm headed in here.

The challenge there is if you look at the fully loaded cost of a CRM coach, it's like a hundred bucks an hour. Like we'd have to charge a hundred bucks an hour to our customers, and even that would not really make us any profit. Our customers are price sensitive, they can't pay a hundred bucks an hour. That maybe here and there they could, but for the most part they wouldn't.

So where what is where does that leave us? Um the idea here is build something like a productized service, but with someone else's product. And what I really mean here is like well, I'll just give you I'll I'm gonna go all the way to the bottom of the idea and then what we can pull back up if there's time. We have a thousand users in our free trial uh pipeline right now.

Four hundred of them have an at gmail.com domain name. Can we just email those 400 people and say, hey, do you want a real domain name for your email? 50 bucks a month.

We'll do that. We'll get you a little website set up. We'll set up your Google Places listing. You know, whatever.

Like some set of services where it's like, it's not just general consulting. It's not general IT services. It's like we have a menu of things we offer where the value the customer receives is high enough that like it, but it doesn't require that much of our time. Th this is the S and B version of another idea I have, which is like every like if you want to do services right now, you want to specialize in what I would the broad topic here is AI transformation.

Um, and so what you're saying is accelerate the technical adoption and excel transformation of a a very small business that's using Gmail still as their primary business email. But like if you extrapolate that up to like where where like maybe the bigger dollars are, it's helping any company accelerate their adoption of technology, namely uh AI. Yes. And but and I wanna separate the value provided from like the hours we're putting into it.

So at if you're doing this at the enterprise level, you have to you have to be like, it's five hundred dollars an hour, we're gonna send a team of people in, we're gonna spend six months embedded in your company. If you're doing it at small business, you have to say, We've done the exact same thing a thousand times and we'll do it for you. And you pull you pull the resource across multiple of these. It's like an insurance policy basically.

Fifty bucks a month and you don't have to worry about it Yeah. And you can you need to update your uh how many of our customers do you think have a website? They paid someone to set it up, they're s probably still paying for it, but they don't even know how to update it, you know? I have two examples of this in my own family.

My dad has his own law firm now. My uh my my father-in-law has a painting business. Guess who manages their websites and email addresses? Me and Sable.

Sable, her dad, yeah. So like I would love and it's it's not worth my like I would say, Dad, you gotta pay you gotta pay less than like scaraby bucks for this. exactly. I and obviously this isn't a few the reason I'm not listing this as a hedge.

This dies the same way less annoying serum dies, probably. It's a crop but like I think I did the math. Um yeah, go ahead. I was just gonna say, I I just I think that this is if you can get I think this you're you're operating still with the less annoying CRM constraint of like what less annoying CRM is.

If it if there is a hedge um and you have this like resource, like if if your larger hedge is like we build software, we uh adopt AI, and we have people that do uh value added services uh that are packaged in a certain way, uh sometimes it's and that's gonna be an advantage for us. You can do a lot of different things. Uh okay. All right.

I I think there's a the safest, most real if if you said I need to make a hundred thousand dollars a year in revenue from something some new line of business, guaranteed or close to guaranteed a year from now, we sell the safe thing, which is Gmail. We'll get a Google Workspace account set up for you, we'll buy your domain, we'll manage it. I agree that as time goes on and we have the bandwidth to grow this and customers and AI and all this, I think that. Other things like this that are more in the AI realm is more of a hedge, but also less of like a guaranteed revenue, right?

Yeah, and I this is 30, I'm I've I'm flying down this is like the six month plan that we're talking about. This I I flew up to the 30 year plan. Like what are what are the pillars of strategic sort of like truths that we're gonna bet on? one of them is we're gonna have uh humans whose job it is to to is to help uh other companies use technology.

Let's just call it that. Yep. Um, I feel very confident that like there are enough boomers and late Gen X people in the workforce that there will be a market for this for five or ten years. Uh a market for this by w I don't mean that I there will be people who are like, I want to call somebody and have them do it for me.

I don't know if Gen Z or millennials will want that. So I don't know if there's a 30 year I I don't know if services business, IT businesses exist 30 years from now, but I do think there's like I it feels stable enough to me for five or ten years, at least. Is my guess. Yep.

Until you know more. Until we know more. So yeah, it it would just be a starting point, but that's the safe bet, I think. Lots to figure out there.

But you know, we have about f I I think four thousand existing customers with at gmail.com addresses. And then again, four hundred four hundred is probably a little, probably three hundred, three fifty per month coming in. Those are not all qualified leads.

Many of those are tire kickers. They were never gonna use less than serum in the first place. But the anyone who uses us as a CRM, they trust us, they've seen were quality, even if they didn't use our support, they know they see they got all those drip emails from a real person saying, Hey, just reply to this and I'll get back to you. Like they're gonna trust us.

I yeah. I I'm pretty excited about this as just like a safe way to extend the runway. Mm-hmm. Cool.

Yeah. So I haven't announced this to the company yet, but we're gonna do it. Cool. That's awesome.

And there's a lot there's a lot of automation opportunities with that type of service too. Like Yeah. of all these different ideas that, you know, some are hedges and some are not, the ones I really like are ones that you can sell with having built almost nothing, but then you can build it. Like we can do this manually with just human labor and then we can automate it away, as opposed to like we have to go I know building is quote unquote free, but certain things still take months to build if you want to do it well and you wanna com you're competing with other big tech companies and stuff like that.

Yeah. That's why I like leg up health as a as a business. Um I o I always knew like, yeah, we can do quotes on Health Sherpa, we can string together tools, we can do these things, but we don't need to build anything to build revenue. And then yeah, we can start to chip away at this thing.

And I that was before AI. So it's pretty cool. I agree. It's cool.

Progress. Yeah. Um, so we're basically out of time here. Next episode I'm guessing I will have the hedge options, if not fully figured out, at least partially, so I can talk more about that uh next time.

Awesome. Well, um, thank you for sharing nice work and look forward to hearing more. I will talk we I guess we're gonna talk again in two weeks. Yeah, is that right?

This w this was a normally scheduled one? Okay. All right, cool. See you in two weeks then.

Bye. In this episode, we talk about a new service Less Annoying CRM is going to offer to its customers. Let's go.

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