The Hourglass w/ Jordan Gal

Aaron

Alright. Welcome, back to Mostly Technical this week. No, Ian. Ian is a no man, and he said no to the podcast. And so he's out today.

I think he's at Disney, which we all know my feelings on Disney. But, you know, no shade to Ian. I I think we might we might have a better cohost here. We'll see. Uh-oh.

We got Jordan Gall on the show today. I'm super excited. We've been friends feel like we've been Internet friends for a long time, but never spoken. So this is, this is our maiden voyage. Welcome, Jordan, to the show.

Jordan

Thank you very much. Thanks for having me on. Aaron, have we not spoken, like, on Zoom or something? We must

Aaron

I I don't think we have. I've heard you talk about me on your show, and you've heard me talk about you on my show. Yes. We've DM ed, but we've never spoken.

Jordan

Very funny. I feel like I know you. Same. I have questions for you. I'm looking forward to getting to know you more.

Aaron

I can't wait. Also, I'm kinda nervous, but I can't wait.

Jordan

Well, look. The number one rule I have for this podcast is we cannot talk trash by Ian. He's not here to defend himself. Ah. So, Ian, that was

Aaron

my number one that was my number one topic. So dang it. That's too bad. And thank you for wearing the uniform, the black shirt and the glasses. I really appreciate that.

Jordan

You know, this is my actual uniform.

Aaron

Uh-huh.

Jordan

This is maybe four out of five days a week.

Aaron

Yep.

Jordan

So it's not for you. It's just the uniform. It happens to be very similar to yours.

Aaron

Yeah. I appreciate that.

Jordan

Have you considered the LASIK surgery?

Aaron

No. I haven't because at this point, it's part of the it's part of the style. Like, I like I like wearing glasses.

Jordan

That's how I feel. The other day, I thought I maybe I can get the surgery in silverware glasses. No. I can't live with myself if I do that.

Aaron

Yeah. Fashion glasses are tough to rationalize in in my opinion. I know that people do it, but I would feel a little bit I would feel a little bit inauthentic wearing fashion glasses.

Jordan

Fair. Fair.

Aaron

Yeah. Alright. So you're here. I am. I've heard you doing the tour.

I've listened to all of your your guest shows. You did one with Rob recently. Rob Walling started for the rest of us. Yeah. So I feel like I have a little bit of, a little bit of fact story of what you're up to.

Where do you where do you wanna start? We've I've got topics. I've got topics for you. We could talk Rosie, which is your your new startup. You can ask me questions.

What do you wanna do?

Jordan

Okay. Okay. So I do have some topics. I don't I I I wanna, like, give, you know, to to at least some of these topics around Rosie and what I've learned. It is but before we get there, let's get there.

But I do want to talk first. I want to ask you about podcasting. Okay. I want to ask you one thing very specifically to start off. Okay?

I associate you with the phrase, you can just do things.

Aaron

Love that for me.

Jordan

What what I wanna know is is is it your original, or is it are you do you so embody this phrase that my the association is very close for me? Which which one is it?

Aaron

You know, it's good for the lore and for the aura to say, this is mine, and I invented it. Yes. I'm not sure that that is true. I'm I'm pretty sure that that is not true. I don't think I am the originator of the phrase, but I think to some extent in our in our maybe our little corner, I have popularized it enough that people associate it with me, which is good enough.

That's good enough for me.

Jordan

Yes. Fair, humble, honest, and it does answer the question. Because I And I was trying to

Aaron

be clear.

Jordan

Because I find myself saying it all the time now.

Aaron

It's great. It's just so pithy. You'll be pleased to know I do own the domain. You can justdothings.com. That might be that might,

Jordan

you know, be the deciding factor. You now will maybe There you go.

Aaron

It's mine. I don't know who can say. Okay. So yeah. And I do love I do love when, like, Sam Altman will say something like, You can just do things and people will tag like, Hey, did you steal that from Aaron?

And I'm like, I don't know, guys.

Jordan

Look, good ideas are contagious as are bad ideas, but we push the good ideas. I have another question for you.

Aaron

I love this. This is great.

Jordan

Alright. So here's the thing. Okay. You've you've seen me on a bunch of podcasts for

Aaron

for two reasons. Mhmm.

Jordan

One good, one not bad, maybe ugly. Let's call it. K. The first reason is because I am trying to figure out how to create more content.

Aaron

Sure.

Jordan

And I plan on starting my own podcast in the future. So I was like, best way to do that, let me go on to these shows. The the second reason you've seen me on all this all these, just seeing more of me is because Rosie's doing well.

Aaron

Okay.

Jordan

And and that is a weird thing because that means that means my confidence is directly tied to the performance of the business. And my willingness to go out there and create content and be in front of people and basically talk with some sense of authority relies on the success of the company that I'm currently building. And I have to kind of, like, confess, when things were not going well with Rally, I felt inauthentic coming out and being like, here's what you should do. Do. Here's what works for me.

Because nothing was really working. So anyway, that's somewhat ugly. The question is, what makes a podcast compelling? What makes you want to hit play on a podcast? All of this stuff that I'm doing, I'm trying to figure out what kind of podcast I want to create.

Aaron

Mhmm.

Jordan

And I have been trying to analyze it by looking at my Spotify podcast list

Aaron

Mhmm.

Jordan

And trying to identify why do I want to hit play or not hit play. So what is it? I think of your podcast, Dean, as one of the ones that I wanna hit play. I wanna ask you what what you think does it. What makes a podcast?

Aaron

That's interesting. Compelling. Okay. So as as an avid podcast listener, I listen to tons of podcasts. Yep.

So I feel well qualified to answer this. I really like, I really like the the ride along shows. That's what I like. That's what I what I liked about your show, that you did with Brian for so long. That's what I liked about Art of Product, Hackers Incorporated for a second, old school, old school startups for the rest of us when Rob and Mike were on there just sharing the journey.

Okay. I like I like the ride alongs, the, you know, what's going on this week? How's your father? What's the good word? That kind of stuff.

Right? So I like I like to know the cast of characters, and I like to know, like, hey. This person I get it's like a longitudinal study in a business. And so I get to hear the ups and the downs. I get to hear that we tried this.

We you know, this didn't work. That's why I think art of product was so good because Ben and Derek were both, like, building. Yes. Yeah. They were building.

And every week, you know, Ben would come on and be like, well, I did a enterprise sale, and I just, you know, multiplied the number times 10, and they still said yes. And I'm like, this is great. This is gold. I love hearing this. And and you you

Jordan

hear something that came up a month ago and then where it ended up.

Aaron

Yes. Exactly. And so the thing, the thing that I don't like as much is when people pivot to people pivot to interview only. I don't like that as much. Mhmm.

Because then I'm like, do I wanna listen to this guest talk about this thing that doesn't matter to me? Right.

Jordan

And the host that you might have a connection with isn't really part of that conversation. They're facilitating the conversation, but it's not the same thing.

Aaron

Okay. Exactly. So when you're when you and or you are, Jordan. When you and Brian are talking about how you're, like, trying to do you know, back in the rally days, you're trying to, like, figure out this headless, you know, checkout thing, and it's like, this doesn't apply to me at all. And if you if I didn't know you and you were a guest and went on somebody else's show, I'd be like, headless checkout.

Like, I don't even know what you're talking about. Skip that. But I've listened to every single one of your episodes because it's like, I am invested, and I am following along. And so maybe back to your back to your your bad or your ugly reason for not going on, I have found the most enjoyable podcasts to not be the ones that are like, here's exactly what you should do. Here are 10 takeaways for, you know, b to b sales or something.

I found the ones that I enjoy the most to be, here's what I have done. And maybe it worked, maybe it didn't work. But the, like, the big difference is, here's what you should do, and here's what I have done. I'm always picking, here's what I have done every time.

Jordan

Okay. Very interesting. We we line up on a lot of it. First of all, you like narrative nonfiction. Yes.

That's basically what it's just in real time. A podcast allows for narrative nonfiction in real time.

Aaron

Mhmm.

Jordan

Written on the spot audibly. Yes.

Aaron

It is kind of exactly. It's fun that way.

Jordan

Yes. Yes. Yep. Yeah. I I when I first set out in my mind, I said, okay.

I'm gonna I'm gonna start a podcast.

Aaron

Mhmm.

Jordan

The obvious thing in front of you is an interview show.

Aaron

Mhmm.

Jordan

Yep. Because that allows you to interview people from your space, from your ICP. You you can interview people. It's, like, strategic. Like, I'm gonna talk to this person who runs a $20,000,000 roofing company that they acquired using an SBA loan, and that is gonna get pushed out, and my ICP is gonna be attracted to that because it is just like them or just like who they wanna be.

Mhmm. My problem with that that's that was my original thought on on the new podcast. I promised it didn't sound like any fun.

Aaron

No. I'll I'll be honest. It doesn't. Doesn't sound like fun? It really it really doesn't.

Jordan

And and when I think about my Spotify playlist, what does it for me is that it sounds like fun. Mhmm. I listen to too much politics. So when I get real full on that, because that's not fun these days

Aaron

Mhmm.

Jordan

I look for some form of an escape, but that's business adjacent Right. Or interest adjacent.

Aaron

You can at least tell yourself it's business.

Jordan

Yes. Kinda. Yeah. I'm not looking to, like, make my business better. I'm looking to hang out with some people.

Aaron

Exactly. K. Yes. K.

Jordan

I like David Chang.

Aaron

Okay. I don't know David Chang.

Jordan

Okay. He's a chef. He runs Momofuku, interesting businesses, interesting restaurants, and it's like a hang. Mhmm. I think about your podcast, and one of the reasons I really like it, is because it is half hang

Aaron

and

Jordan

half business. So it's got the narrative nonfiction line running through it, but you're you got you're not in a rush to just get to business and talk about the thing that worked or didn't work and just, you know, focus on that.

Aaron

It is not the most value dense format. The way that we do do the show is not the most value dense, but we're also not in we're not in the value dense game. We're in the sweet hang game. You know? Yes.

That's that's the game that we're playing. And I saw you tagged, group chat news. That's why we love group chat. That's why we love that podcast. Yep.

Because they, like, they yuck it up for half the show, and the other half, they're talking about what they're seeing as, you know, retailers and is the consumer soft. And I'm like, I don't know anything about this. Tell me more.

Jordan

Right. And it doesn't directly impact your business, but it's just interesting in general.

Aaron

It is. If you take ten

Jordan

minutes and talk about the golf tournament you went to, it's still interesting because I like you, and I wanna hear about it. Yeah. So I've been trying to figure out what what what that is and what that format is. Yeah. And so maybe this is a good transition.

I can talk about the thinking there and where the podcast is going to live in Rosie's business in general, because this is not for me personally.

Aaron

Yes. So I wanna hear, I wanna hear you back up a little bit and tell me the story of, the end of Bootstrapped Web, and now you've both gone both gone on to do new podcasts that are similar and different formats. I mean, he's doing the panel with Justin Jackson, which is very enjoyable. Yes. Same.

You're looking you're looking for something that I think is more, like, pointed at the people that would consume Rosie. And so tell us, like, couch it in that narrative. Give us the kind of the story there.

Jordan

Sure. Well, Brian and I had a great time. We we did podcast for ten years. Ten ten years. Yep.

We really saw each other through, you know, a big portion of our lives and careers, family having kids, moving cities, the whole thing. So it was a lot of fun. The way Brian and I started out was through Mixer GE. Back in the day, Mixer, he posted something about, like, Andrew Warner, right, from Mixergy. He posted something that was like, what if I did a mastermind?

Would you be interested in it? So both Brian and I reached out and were accepted into the original mastermind with Brennan Dunn, with a few other guys. Boy.

Aaron

Yep. Old school years ago. I remember Brennan Dunn being big on the scene. That's right. Those were those were the days.

Jordan

What Brian and I realized by some insane coincidence is that we lived ten minutes from each other.

Aaron

I did not know that. Yes.

Jordan

We both lived in Connecticut. I lived in Westport. He lived in in Norwalk. Ten Minutes from each other, and we were like, well, this is weird. I guess we should, like, get to know each other.

And that's where the podcast started from. So we really started way back.

Aaron

Yeah.

Jordan

In terms of the end of the podcast, I think it was just time we were starting to go in different directions.

Aaron

Uh-huh.

Jordan

I think the most important thing is I was holding him back. Mhmm. Because I started looking at the podcast. This is just a fun thing I did on Fridays. Mhmm.

But I needed to put more effort in, and it wasn't fair to him because he was putting effort in. And I was just showing up on Friday and then walking away. I didn't promote it. I didn't even say, hey.

Aaron

We should have

Jordan

a new episode. I just thought of it as, like, this therapy session for myself. Mhmm. And I had fun, and it was valuable for me to synthesize the stuff at the end of the week. But but it it started coming out of whack.

And I'm not surprised right now that he's going off and doing something, I think, better. And I'm gonna go off and do something better because we're breathing new life and energy into what we're doing on the podcast front

Aaron

Mhmm. From a

Jordan

different point of view, maybe a more honest point of view. Like, no. I I need to do this, and I wanna do this for myself in this way. So it was just time. It was ten years.

It was awesome.

Aaron

Ten years. I remember I think I started listening back when restaurant engine was a thing. I remember listening through your decision to move cities. Yep. I man, I just, like I followed that thing for forever.

Yeah. So It's a trip. It's So it had a big impact on on me. So it's a fun fun show.

Jordan

Thank you for saying that. And I'm

Aaron

I'm glad it exists and lives on the Internet Mhmm.

Jordan

In general. And that that that's great. Yeah. Now now it's time to do something else. And I don't necessarily care to link it to Rosie's ICP.

I think the most important thing is to have a great time and really enjoy it, and I think that will that will be the most compelling version of a podcast that I can do.

Aaron

Mhmm.

Jordan

The exact format, I'm not sure of.

Aaron

So what is the, so if you're justifying putting more time into it and you're saying, alright. I need to put some effort. I need to bring some stuff. I need to promote. Like, I'm gonna make this a part of my life and my business.

What is your, like, desired outcome from doing a podcast like that if not necessarily linked to Rosie's ICP?

Jordan

Yeah. So a lot of this stuff, I end up going through a a similar cycle where a lot of it starts off as this very calculated, somewhat cynical decision of I I want content for Rosie.

Aaron

K.

Jordan

And then I back away off the cynicism, and I say, well, okay. How do I make enjoyable? How do I make it so that I care about it? Because that's actually the best version of the product.

Aaron

I I would I would challenge cynicism, and I would say it's strategic. That's extremely strategic.

Jordan

Sure. Sure.

Aaron

Yeah.

Jordan

Okay. So here's where it fits in. We launched Rosie, I guess, July, we took on our first users, and then August 1, like, you know, Yes, you can log in. Here's a username and password version of the product. And then October, it started working with the first cohort and we asked them for money.

And then we started making our way toward self serve. And then it really kind of popped when we added a few features and self serve. And we can talk about that process, that I'm calling an hourglass process. We'll get into that.

Aaron

We love a name we love a name for things.

Jordan

That's great. Names are important.

Aaron

Oh, that's

Jordan

great. You know what I call these? I call all these lies. L a h. Like, learning in hindsight.

Lessons in hindsight.

Aaron

That's great. That's great. You fit in you fit in perfectly here. Okay. Keep going.

Jordan

Yes.

Aaron

We'll we'll come to Hourglass later. That's great.

Jordan

So where it fits in right now is that advertising is working for us. I did not expect ads to work for us, but I had a hunch that it could because our ICP being like small businesses and local services, I just think they behave like consumers and they're just hanging out on Instagram and TikTok like everybody else. So we have been pushing ads there, and it really worked. So we are ramping up investment, and I'm a little shocked by how much money we're spending on ads. It feels very strange to do so, but that's why we raised venture.

So, ads are working. Okay. Got a great SEO company on board. Got them on board probably in December, and now it's like officially working and publishing things all the time and so on. And so the next step is more content.

And so I've tried to think about how do I create content that makes sense for the business in a way that doesn't make me cringe too much and and all that. I decided that the best way to go with content for me as the founder, because I think people don't pay attention to companies. I don't pay attention to any companies.

Aaron

I agree. I don't

Jordan

care at all what a company says. Okay. So that was, like, the first big fork in the road. Okay. It's gotta come from me.

So what I did is I hired a content agency that creates content from me as the founder. K. Okay. So now we're talking strategic. You don't wanna call it cynical, but strategic.

Okay. Next thing you

Aaron

know We can call it ruthlessly strategic if you want. Yes. That's fine.

Jordan

So think about put yourself in in these shoes. You're gonna go spend money, and this company is gonna create a lot of content that comes from you and your Twitter profile and your Facebook profile and your LinkedIn profile and everything else. Once you internalize that that's about to happen, you have a choice. You could not care and embrace the cringe, or you could care and say, I gotta make this good.

Aaron

Mhmm.

Jordan

So that's where I'm at right now. Yep. There's a whole bunch of content. I'm about to be a thread boy, okay, on the Earth.

Aaron

And you gotta live with

Jordan

your decisions. Right? Here we go. So starting in, like, a week or two, you're gonna start to see a lot more content from me. And when I thought about that, I started to sweat from shame and embarrassment.

Aaron

Sure.

Jordan

And the only way I can kinda get through that is by saying, I'm gonna make this good. And the best way that I can make it good is to generate the foundational content for all of it through a podcast. The medium sparring partner. The medium that I'm most comfortable and most confident in talking on video like this

Aaron

Yep.

Jordan

Let that be the foundation of the content that they can clip from, they could take ideas from, turn into threads, turn into posts, turn into carousels or whatever else there is. Yep. So that is where the podcast thinking came.

Aaron

Okay. So I buy it because backup backup thirty to sixty seconds. Okay. You're the agency. Backup this show thirty to sixty seconds, and you've got a blog post, a thread, a LinkedIn post all about authentic content from the founders.

And then you just it came off the top of your head while you were speaking in the zone hyped up. And now in that chunk, they've got a week's worth of content right there.

Jordan

Yes. So that is the ideal. And so that because of that, I am allowing myself to not worry about the content being so right for the ICP. Mhmm. Right that look.

I I started off thinking I need to create a show for SMB AI. Right. How are SMBs using AI in their business? In a calculated way, that's probably the best content for our ICP.

Aaron

Mhmm.

Jordan

But I'm gonna I'm gonna lose my mind from boredom doing that.

Aaron

And and honestly, Chris, my lawn guy isn't looking for podcasts about AI and SMB, frankly. He's just mowing lawns and making a ton of money. Do you understand? Yeah. It's

Jordan

great that this actually

Aaron

Yeah. I know. I pay him. It must be.

Jordan

Yeah. I have the kind of landscaper that just doesn't bill me and then sends me, like, a $2,000 bill six weeks later. And I'm like, what what why? What'd you do?

Aaron

I got one of those when we sold like, a few years ago, we sold a house. And I to my credit, I had flagged this guy down three or four or five times and been like, hey. Do you have can I, like, pay you?

Jordan

Yes. Do

Aaron

you have a invoice? Can I pay you? And he's like, yes. You can pay me. I'll I'll get you an invoice.

Right. Nothing. Nothing. Nothing. Put a for sale sign in my yard, got a bill for $3.

Yes. There you go. Okay. Okay. Where's, like, where's the documentation?

Yeah.

Jordan

Help me out.

Aaron

Oh, I don't I don't have it.

Jordan

So yes. It's tough. It's my job to make sure that that guy has an AI answering their phone before they have an invoicing system. Okay?

Aaron

Wish me luck. That's fine. Good luck. Yeah. That's fine.

The new guy sends me a a Venmo request every week, and I just yes. Good job. There you go. It's great. I love it.

Jordan

So if we if we go back into the in into the the podcasting Mhmm. What I now that I'm fully engaged in this mindset around Mhmm. Generating content, I think what you'll find whatever everyone listening to this, if you become more aware of what you're doing during the week, you're actually a content machine. You have 100%. There's so much.

There's so much. And I have a list of things that I can go through from the last few weeks and months of Rosie that I basically just formalized. I talk about them all the time internally. It's almost like I practice explaining my thinking to people on our team effectively to justify my decisions as CEO. Here's an example.

Why are why is Rosie a horizontal software and not verticalized? Okay. Generally speaking, advice to a a software founder, I would say, don't be general. Find a niche. Yep.

Nail it for them.

Aaron

Worry about that. Do the Nathan Barry. Do the Nathan Barry. Do bloggers or whatever, and then just make a ton of money.

Jordan

You are you are good at this because that's why

Aaron

I'm in the game. I've listened, man.

Jordan

That is okay. You good. So that's my example. Yep. My example is ConvertKit.

If email gets invented, you don't build ConvertKit. You build Mailchimp. When the market is just forming, you go very horizontal to capture as much of the wave that's on the way as possible. And then you have a problem on how to verticalize. Do you build extra features for specific verticals?

Is it just a marketing play where you have a page and a case study and a whatever geared toward that? And that's kind of later. So here's the thing. You've probably heard me say that before, right, on Rob's podcast. So I'm, like, turned into, like, an actor practicing my lines.

Aaron

Yep. Yep. Mhmm.

Jordan

And then I oh, look. That's a little bundle of content. It is. That's a little package. And how do I I've never been able I don't have discipline like you.

Aaron

Well, I appreciate it, but I don't know. You

Jordan

make, like, 30 videos a week. Sometimes. I think about them, and I don't make them. And my hope is that this content agency and this potential shame around being too cringey and my own content coming from me being bad has finally motivated me to go just far enough in packaging these little bits of content Mhmm. To at least hand them over to someone that I paid to actually post them as content.

Aaron

That's You know, being being driven by shame. I can't I can't endorse I can't endorse that strategy, but if it works, I'm proud I'm proud for you. So here's, I fundamentally 100% agree. And to point out someone who does this super well, I think, would be pointing back to our mutual friend, Justin Jackson. So Justin will back when he was on Twitter, RIP, Justin Justin will go on Twitter and throw out an idea.

Right? He'll throw out an idea. He'll he'll, like, you know, yuck it up with the normies and go back and forth in banter. K. Then it becomes then he talks about it on some podcast.

Then he puts it out in some newsletter, and then it comes back out on Twitter in a more refined fashion. And it's just like, he just kinda he just kinda bandies about the idea or the problem until it's refined and honed down into something that ends up as a blog post and a newsletter and a podcast episode and now a YouTube video. And I think that is a very that's, like, a very good way to hone the message. And I think, partially, also what you're describing is bits and sticks. Right?

We've got bits. We've got sticks. I've got my you can just do things, you know, try hard. Like, all of those things, like, they end up being, I think, functionally memes, but not like, you know, cheap images. But it's like Yeah.

It's a it's a simplification of kind of like a point of view or a way of living or an idea. And if you do that enough, people start adding on to it for you. Like you asked at the beginning, like, I see people saying this. Did you invent this? It's like, no.

But if you say something enough, people start attributing it to you. And podcasts are a great way to get that, like, that first draft out there, especially if you, like me, have a good sparring partner. I've got Ian who is, like, very smart, doesn't always agree with me, which is amazing, but wants, like, wants me to succeed. And so he's always trying to, like, let's let's get to a good place together even if we fundamentally disagree on some things. And so I'm I'm all on board as podcast as, like, we could say content engine.

Even if, you know, Chris, at the light landscaping service doesn't listen to the show, it is the nugget from which other things can, you know, spring.

Jordan

Yes. I'm I'm pushing off the ICP concern out into the future Mhmm. Because I think it's because I have felt what you feel and other podcasters feel. You don't just give, and and it works out. It'll it'll all come back around.

You really don't have to think about the outcome. You just keep doing your thing and keep giving, and it makes everything easier and better. So I'm just really just pushing off that concern. Because in reality, after two months of doing my podcast and eight episodes are out, when I then reach out to the amazing, deck building company in California, this guy on Twitter is awesome. He doesn't know me right now.

Two months from now, it's much more likely that he'll say, yes. I'd love to come on the podcast.

Aaron

A %. Yes. So it's

Jordan

like Yep. I'll worry about that later. That's that's

Aaron

fine. Yep. Yep. And now with, as you well know, all these AI tools, your, they can gather your your digital detritus. Right?

So you've got a bunch of tweets. You've got a bunch of podcast transcripts. You've got maybe some newsletters. They can grab it all, and I have done this. I have actively done this many times.

I have, like I exported, an archive of all my tweets, so I have them all. I've got blog posts that I've written turned into, like, you know, one giant PDF, and then I've got all podcast transcripts on aaronfrancis.com. And so then I can go to Gemini deep research and say, hey. Here's what I want you to look at. Look at everything I've said on this topic, this idea, pull examples from the shows I've been on, and write me a first draft.

Here's the title, and here are the key highlights I want you to hit. And it, like, spits out a first draft. And it's all stuff that I've said. It's just, like, scattered across the web, and it pulls it all together for me. It's awesome.

Jordan

Yeah. Very interesting. I have not I have not I have not done anything like that. Reminds me of a very funny experience we had a few nights ago. My wife had her first AI experience of, like,

Aaron

oh

Jordan

my god, this thing works. And what was it for? It was for a scavenger hunt, a set of poems on where to go in our house next. Cool. It did it so perfectly.

But it's a reminder, you you you can do more with your content than you think you can.

Aaron

Yes.

Jordan

With these AI tools, I I I don't think of that, but that's very interesting. I would love to put all of my podcasts somewhere to be able to access it. Yeah.

Aaron

Yes. Yeah. Especially you with ten years of of podcasts. You've got transcripts. I mean, you've you've talked about a ton of stuff.

And so getting all of that transcribed and searchable yes. Searchable, but, like, consumable by an LLM Yes. Your agency you're gonna be the easiest client your agency has ever had. It's unbelievable.

Jordan

Yeah. That's that's my my hope is that the content they create originates from my thinking and my experience.

Aaron

As it yes. Yeah. As it should. Yeah.

Jordan

Right. That's kind of what you want. And I have been taking tweets and posts and showing them I like this and I don't like this, and I identify very, very strongly with your your preference for advice

Aaron

Mhmm.

Jordan

On it being, here's what I did. Here's what I

Aaron

learned. Mhmm.

Jordan

As opposed to, this is the way it's done.

Aaron

Yes.

Jordan

Here's how here's how you should do it. If you're not doing it, you're doing it wrong.

Aaron

Yes. Yep. Don't I don't like that. I don't like that to consume. I also don't like that to produce, and I think a lot of people try to produce content like that.

Like, here's the way you should do things, and it's a very high bar. Like, if you're if you're intellectually honest, it's a very high bar to say, here's the way you should

Jordan

do things with no doubt.

Aaron

If you're if you're a grifter, it's fine. You can just say that. Right?

Jordan

The danger is the grifter is confident. And then there's, like, this memetic, like, experience where people, like, I guess that's what gets likes. Yep. But it is it is unhealthy. Not good.

Aaron

Yes. Yes. And so it it creates this artificially high bar, and people don't produce content because they're intellectually honest and don't wanna say this is the 100% right way to do things, when really, I wanna hear how you did something. Yeah. And you can tell me why you thought it was the best way to do it, but don't tell me that it is.

But just tell me what you did. That's all I wanna know.

Jordan

It's tough because declarative on Twitter is better than caveats and Oh, it's a nightmare.

Aaron

I don't know if you've seen the most recent trend of, like, the first sentence is Salesforce is dead. And then it's, like, you know, three paragraphs of, like, why AI

Jordan

is I'm like, triggered

Aaron

out loud. One of them one of them recently was like, Stripe is dead. And then it was pitching a product that's built on top of Stripe. And I'm like, what are you doing?

Jordan

That's perfect.

Aaron

Oh, god. Yeah. It's the it's a nightmare. Okay. I'm pro I'm pro podcast for you.

Yeah. We gotta get we gotta get this going.

Jordan

Yeah. I'm I'm I'm going. Well, I'm not going right now because I'm going to Hawaii on Wednesday.

Aaron

Yeah. You are. I'm not

Jordan

gonna think about any of this. K. I ain't gonna think about it, but just think.

Aaron

Of course you are.

Jordan

Yeah. Of course you are. You know, here's a recommendation. I wanna I wanna do a recommendation real quick, and then I want to get into something concrete, about, time. You can choose.

Early product model fit, the hourglass process, or time versus usage based trials. Okay? But first, while you think about that, here's my recommendation. My recommendation is a little piece of hardware called Brick.

Aaron

Got it. You you got it? I have it. I think because of you.

Jordan

On the way. Okay. So I'm I'm so excited for this week to use it in my hotel room because you you have to touch your phone up against it. And when you do that, it blocks only certain apps. Because I need, and this is a perfect excuse, I need my phone.

When I'm in Hawaii, I need Waze, I need Google Maps, I need Yelp, I need the phone itself. And I don't need Slack, and I don't need Twitter. And so Slack

Aaron

I agree with, but, yeah, keep going.

Jordan

Right. Well, for me, it's business and politics. I'd rather read Kindle than hang out with my kids.

Aaron

Yes. That's probably fair.

Jordan

So that's that's my recommendation. There's this piece of hardware called Brick that's fantastic. And then in order to unlock those apps, you have to touch it physically up against the brick.

Aaron

Physically.

Jordan

So I'll leave in the hotel room.

Aaron

Yep. And okay.

Jordan

So I'm very excited about that and my ability to unplug. And and I'm

Aaron

I'm excited for you. The brick, I think it's, like, brick it app or you'll you'll find it. You can Google it. Brick.

Jordan

You know? And it it's

Aaron

an NFC thing. And I don't know how they do it, but it, like, hooks into the screen time APIs. And so you're like, alright. I'm ready to break. And you click the button on your phone, and then you walk over to your physical device, and you, like, push your phone down, and it scans.

And then you can't you can't get in. Yep. Like, it's it's game over. Yeah. To only see And so Yeah.

And so then I have one I have one in my car and one on my nightstand. And so, like, you know, on Saturday, I'll you know, I try to break my phone before I walk out to go get the kids out because it's like, it's Saturday. You don't need to be arguing with people on Twitter, so brick your phone. Yes. Yes.

Yeah. It's awesome. I love brick.

Jordan

I do the same for for dinner time. Yep. Like, my kids are finally home, like, get get off get off the damn phone.

Aaron

Yes. Exactly.

Jordan

With moderate success

Aaron

if if Moderate. Yes.

Jordan

But this week in Hawaii, full success. I'm looking forward to it.

Aaron

I love I love that you're as much of a Twitter addict as I am. I think you you lean way harder onto politics Twitter and for for good reasons in most cases, but you're very you're very online, and I I love that about you.

Jordan

It's addicting knowing everything.

Aaron

It is. It's not great. It's not great. It's not

Jordan

it's not great. It's not great.

Aaron

No.

Jordan

Plenty of, money spent on therapy.

Aaron

Yes. Yes. Okay. Are you

Jordan

ready? I'm gonna give you I'm gonna give you the choices. K. Hourglass

Aaron

Mhmm.

Jordan

Like feature product process Mhmm. Early product market fit, and time versus usage based trials.

Aaron

K. I've got my answer. Before we do that, this podcast is brought to you by Bento. Bentonow.com. Bento is the email service provider, the refreshingly delightful email marketing platform.

We use that at TryHard Studios for both marketing and transactional emails. So check out bento at bento now dot com. Thank you to Bento for sponsoring. And PHP Tech twenty twenty five. PHP Tech is the conference for continuing education and community building for PHP developers.

It is May at in Chicago. So thank you to PHP Tech at PHPTech.i0 for sponsoring the show. Alright. I've got my answer. Early product market fit.

For sure. Because you've taken off like a rocket. You banged your head against the wall trying to beat, you know, the goons at Shopify, which I don't wanna do generational trauma, but I wanna talk to you about Shopify checkout because I just had an experience. Sure. But you banged your head against the wall, sheer force of will for a super long time, and you're like, finally, you know what?

F this. I'm gonna switch into AI voice answering Yep. And you took off like a rocket. This is what I wanna hear about.

Jordan

Okay. I I think I talked about this maybe on Rob's pattern. Maybe it was in private with Rob, But it was a strange experience to have product market fit a few years ago with the checkout product

Aaron

Mhmm.

Jordan

Then rebuild the same checkout product more

Aaron

or less, but better with more money, with better design, with better team, with better everything,

Jordan

and then just not a product market fit. So, you know, that was a painful lesson

Aaron

in in time. When you've been to the mountaintop

Jordan

Yep. Yep. And then you build the same product, and you're like, Same mountaintop. Here we go, but bigger and better and more resources and all that. And nope.

It's not really in your control. And then all of a sudden, to basically just face reality

Aaron

Mhmm.

Jordan

And say, we should stop pushing this boulder up the hill. It's too heavy. Mhmm. You know, pushing a boulder up the hill that, like, cartoon that that is being a founder and an entrepreneur, sure. But I guess sometimes you just go find a different folder.

So that's what we did.

Aaron

We So let let me give the people the broad strokes. Sure. Sure. You had a very successful company that was a third party checkout for Shopify Yes. That boosted average order value with upsells, downsells, cross sells, all sorts of stuff.

Jordan

Yep. Went

Aaron

went great, ran into platform risk pretty head on, and they were like, you know what? Actually, we wanna own the checkout. Thanks. See you later.

Jordan

Appreciate the innovation

Aaron

that everyone

Jordan

wants, but we'll just inhale that into our system and commodify

Aaron

Exactly. What

Jordan

we're doing. And you can

Aaron

do that. So much you took your ball and went home. It's they took your ball and you went home. Yes. And so so then then you went out and built the same thing, which was, like, a third party checkout, but in, like, this whole headless ecommerce Yes.

Space, and found the market very, very difficult is is my understanding. And so then after that, you're building you you're building this thing. You're spending a bunch of money on salaries and sales, and finally, you're just like, y'all, I don't think this is working. Mhmm. Incredibly, bold and brave move to say, not only is this not working, but we're not pivoting.

We're just starting something brand new.

Jordan

Yes.

Aaron

It's not a pivot. It is like, I'm gonna go I'm gonna go on a journey for three weeks and find out what we're gonna do next. And if you wanna come along when I get back, we'd love to

Jordan

have you.

Aaron

And so you, like, went into the wilderness, talked to a bunch of people, came back, and came back with AI answering, sits above an answering service below a a full human. So Yes. Those are the broad strokes.

Jordan

Yes. That's right. So those are the broad strokes. We we had money in the bank. And just like you said, you know, we took the team down from, like, 20 to six Oh.

And said, if you wanna stick around, this is what we're doing. Here's why I think it's gonna work. I understand if this you're no longer interested in this, version of the experience. So Do

Aaron

you still have Rock? Yes.

Jordan

My co founder. Yeah.

Aaron

Oh, co founder. Okay. Because he was your CTO before with the whole company.

Jordan

And then co founder. Yep. That's right. And then Jessica also, who is like basically a co founder, but not in name. And she's the VP of product, and she's the one that kinda saved Cardhook from going off the rails.

We had so much demand, and we're growing so fast, but we're churning, like it's just it just wasn't gonna work out.

Aaron

Yeah.

Jordan

And she came in to kind of, like, button up the whole process. And so she came over to Rally with us also, and she's like, the the leadership team is myself and Rock and Jessica.

Aaron

Okay. And last last interruption. But Rock is a Rock's a Laravel guy. Right?

Jordan

Rock is a PHP Laravel guy in Hell yeah. In Slovenia. Yep. Yes. So we've yeah.

We've been in the Laravel ecosystem since CardHook. Like, my original cofounder of CardHook, Ben, was also a big Laravel guy, still is. And that I think that was, like, the gateway into that along with the micro con community and everything else.

Aaron

Yep. Alright. Shout out Ben and Rock. Good job. Good choices, guys.

Alright. Early product market fit.

Jordan

Okay. So I my take was this thing's gotta work quickly. So if we don't see it working quickly, I mean, those investor updates were tough, but, yes, we've raised $18,000,000 for a checkout. Oh. Uh-huh.

And we've decided to do this completely different thing. I was I'm not religious on, investor updates. I don't get them out every month on time. I'm not bad about that, but they are always consistent. There's always one on the way.

And people saw that we tried a lot of different things. We tried hard. Yeah. So That's good.

Aaron

They weren't that surprised. And, you know, as

Jordan

long as we had our lead investor who's on the on the board, like, fully engaged and on board, which he is because I talk to him all the time. So we made the pivot. And what I I was desperately on the lookout for product market fit. I was like, how am I going to know? Because we need to know quickly.

Originally, we went in and we said we're gonna build one product every three months and then see if it works, see if it gets product market fit, and move on and move on and move on. That did not work out. It's much harder to do in Yeah. In reality, especially with

Aaron

the Did you go through that loop? Did you build something and then we're like, no, let's trash it? Or did you just stop before you even executed that strategy?

Jordan

Stop before executing. So we looked at a bunch of different ideas, and then we chose this idea and committed it. And then maybe forty five or sixty days in, we were like, We're not doing anything else. This this is it. We've put a lot of time in.

This is our big bet. If we stick with it for the next year, I think we have a good chance of making it. So here is my version. Let me describe my experience with product market fit at CardHook. When I knew that there was something really, really there, early on, before you were able to sign up on your own, you had to sign up for a demo.

And so at CardHook, I would do the demos myself. And over, like, a week or two span, the demos just changed in nature completely. And it went from here's this product, do you want to buy it, to people just losing their minds on a demo. Just, I cannot believe what you built. It was, like, repeated over and over.

Aaron

God, it feels good. Oh my god.

Jordan

It felt so good. I remember one person specifically said, can you hold on? I need I need to call my friend. He he needs to he needs to come to this call right now so he can see this. And I was like, Oh, oh, I think we have something.

Aaron

Oh, we got it, baby. We got it.

Jordan

Yes. We have something that people really, really, really want. So I was on the lookout for a similar type of experience, but Rosie is self serve. So, it's not the same engagement in a demo. But here's what I knew.

We have events piped into Slack. We have this one channel called, like, I don't know, Rosie notifications, whatever it is.

Aaron

It's very creative. Yeah. Very

Jordan

creative. It shows sign ups, and it shows the first call.

Aaron

K.

Jordan

And then it shows credit card.

Aaron

So k. Over the span telephony. They're like, your customers are taking phone calls. Phone calls. So that's what you mean by first call.

Jordan

Yes. Now the first call is always a test call from them. Right? Makes sense. I mean, in our onboarding, we could talk about onboarding.

In our onboarding, a key step in the onboarding is, here's your phone number. Give it a try. And then if you're happy with it, go to this next step. So this will loop back around to the trials and the changes we made there. But after we made the changes, I would see the same pattern repeating.

I would see sign up, 09:04AM.

Aaron

Mhmm.

Jordan

First phone call, 09:08AM. In my mind, I'm like, it took them four minutes, and they have a voice agent up and running. That that that has to be great.

Aaron

Pretty good. Yeah.

Jordan

And then 09:12, another few minutes later, put the credit card on file. So why would you put your credit card on file voluntarily after you called an AI voice agent unless you were like, oh, this is

Aaron

it. Yep.

Jordan

I I found what I'm looking for. And so that little pattern kept repeating, and I basically told the team, we we got it. We're we're we're there. People are putting in their credit cards voluntarily after a test call. This is now just a matter of time before they convert.

Because they're done. In their minds, they have found what they're looking for.

Aaron

Right. And

Jordan

so the promise that we made in the ad on Instagram has just been fulfilled. And they took action themselves. They pulled out their credit card, and they put it on file when they didn't need to. And we told them this is this is optional. You do not need to put your credit card.

Aaron

Because there's a certain amount of usage they can do without putting the card on file.

Jordan

Yes. That's right.

Aaron

And they looked at it, and they said, I don't wanna remember to come back and put my card on file because I don't want this to go away.

Jordan

That's right. Our messaging in the credit card is don't you know, avoid interruptions. Put your credit card on file.

Aaron

Yeah.

Jordan

Yes. And so now

Aaron

Before before you found product market fit, was that loop much longer, or did it never close? Was it just, like, sign up and then maybe a first call, but never, like, a credit card? Or did it just take seven days?

Jordan

Okay. So let's this leads into the time based trial versus usage based trial. K. So I had a conversation with our friend Justin McGill,

Aaron

who

Jordan

was very successful with an AI product called Content at Scale. It now has a different name. And I remember talking to him and he said, Look, I tried everything. The only thing that worked really well and what worked better than everything else is seven day trial with a credit card required. That works best.

And I said, you know what? That's a good starting point. I like the idea of requiring a credit card because it shows real willingness. He's got some data. It's as good of a starting point as any.

What why start with thirty days when you can start with seven? Because, you know, what everyone says. Okay. So when we first launched, we had a seven day trial with a credit card required, and everybody converted. And I was like, we are geniuses.

And product has arrived. Yes.

Aaron

And then

Jordan

and then what do you do? You look under the you know, a little bit under the hood, and you look at the usage, and you go, oh my god. No one's using the product. Right. And we are building our house on sand.

Aaron

Yes. And as we know, that's not a good strategy.

Jordan

Not a good strategy. So even though the very first month, I think September, October, our our revenue just started going straight up. Mhmm.

Aaron

And I knew that that there was a bad idea Right.

Jordan

To grow based on that. So I said, we're gonna do the opposite. We're gonna we that's one extreme. Seven days credit card required. We're gonna do the opposite.

We're gonna do take as much time as you want. No credit card required. We're gonna give you fifty minutes of usage time.

Aaron

K.

Jordan

So the the most passive version of of the free trial. And what that did is it totally screwed up our growth for, like, three weeks. So we had to just kinda, oh, just get through those three weeks of of no growth compared to consistent growth on the seven days.

Aaron

Mhmm. Which was a facade in the first place. But still, the number goes down and you feel real bad. You feel bad.

Jordan

That's right. So our our, like, profit well graphs are, like, up, up flat and then the next month up. So that's when I knew that we had that first inkling of product market fit because we had built it to the point where people were signing up on their own, not talking to us. They don't need to put their credit card on file. And then we built the onboarding in such a way that allowed them to test it very quickly, and then and then they put their card on file, and then three or four weeks later, we didn't know how long it would take.

Aaron

Mhmm.

Jordan

And at some point, we were like, you know what? It's just, like, fifty minutes, twenty five minutes. That's actually the same thing. So make it twenty five minutes. And then all of a sudden, people started converting, like, two, three days later.

But it was their choice. They were putting the card on file. They were using the minutes. And because of that, our churn is, like, super small. And everyone I talked to was like, Oh, the issue with AI apps is the churn.

And our churn is very, very healthy because 100% of our users are fully activated and using the product.

Aaron

And they put their freaking phone number out to the public, and it's powered by y'all, and they're not gonna switch. You know? Yeah. Like, at that point at that point, they're getting it's just very sticky, I would have to imagine. It's like, you know, switching the domain over and point giving someone else all your DNS.

It's like, do I really wanna switch at this point?

Jordan

It's almost that. And I wouldn't be surprised if we end up in that position a year from today because right now, we give them a phone number and they forward their existing phone number.

Aaron

Their public one to an internal one. Got it. Okay.

Jordan

The phone number is printed on their trucks. Sure. They're printed on their business cards, on their websites. Some people switch right away. Most people are forwarding their calls, and that's actually the single biggest friction to our growth is that Yeah.

That call forwarding issue.

Aaron

So what happens you you changed, like, the billing model, but what did you change in the product? Because, you know, at first, people were signing up and paying and not using it. Then they were signing up and using it. And, yes, the billing model at the front door is different. What did you change in the product to get people to actually start using the thing?

Jordan

Okay. So the this is this is the hourglass process. We're just going to plan

Aaron

for this. Yeah, this is awesome. This is professional life. Yeah. Come on.

Jordan

Okay. I'm going to try The reason I call it an hourglass because it helps me visualize, hopefully helps other people visualize. We started off very wide, the top of the hourglass. We looked at the competitors, and we said, here is our guess at the feature set required to compete. And so what that created was a pretty wide set of features.

Aaron

Mhmm.

Jordan

The product was very young. All those features were very thin. Okay. You could say we have this feature, but it didn't have any options. You couldn't really do anything with it.

But we wanted it on the marketing site to say, we do all this stuff because we wanna be competitive. Check mark.

Aaron

Yeah. Yes. Go to check mark next to it. Give give the people an idea, just a handful of what those those features might be.

Jordan

Call transfers. K. Message taking. Right. So if you call and, the AI doesn't provide you with the information you need and you wanna talk to someone in the office, you can call you can transfer.

The AI says, I'll transfer to the office. Right? Think about what that looks like in software. It's a it's a feature.

Aaron

It's got a whole bunch of options

Jordan

and which phone number at what time and this and schedules. Right? So we just had the most basic version of it. And we had the most basic version of all of these things. Very, very wide.

We get people into the product by sending cold email. We Finally. Yes. We fire up cold email. We send three, four hundred, you know, emails a day.

And that is not a good channel for us. But it it is just brute force to just get 20 people who are interested. So we brought those people in. This is, like, August. And what they did is they identified the most important features.

Aaron

Okay.

Jordan

Features that were actually fundamental to getting value.

Aaron

Mhmm.

Jordan

And what we then did, once we understood the actual feature set required to generate value, is we just removed all the other features.

Aaron

Interesting.

Jordan

Just removed them. Like, you you just can't see them in the app. And so now we're shrinking into the more narrow

Aaron

part

Jordan

of the hourglass. Once we nailed those features and we knew people get value from this, they are paying us for this and they are using it, we call that bang, our base plan. Okay. Okay. So if you go on our site right now, the base plan, it's those features.

Then what we started to do is we started to take the features that we hid and we started to slowly reveal them, but in conversation. So when we talk to someone and they would say, I would love call transfers, man. That's what I really need. We would say, we actually have that feature. It's not that fully built out.

Would you like to be a beta user? And then we would literally just give them the URL that we had hidden. Okay. Yes.

Aaron

So then

Jordan

what we started to do is work with users on those features and started to understand, you know what those are? Those are the premium features.

Aaron

Mhmm.

Jordan

That's all. And so we we built and reintroduced those premium features with the help of users so that we knew what is actually necessary beyond the super basic functionality that we have.

Aaron

Okay. So I've got it pulled up right here. Professional, $49 a month. You've got minutes, message taking with custom questions, smart spam detection, and bilingual agent English and Spanish.

Jordan

Very cool. Very smart. If

Aaron

so that is that's the professional. That's the base plan.

Jordan

Base plan. What the base plan is in effect is it is a message taking service.

Aaron

Which is better than an expensive outsourced human nighttime call service that knows nothing about your business and frustrates me as a user to know it.

Jordan

That's right. That is more what we are competing with in the more premium tiers.

Aaron

Mhmm.

Jordan

What we're competing with at the base plan is your voice mail.

Aaron

K.

Jordan

Because your voice mail has a horrible conversion rate. From call to message that's valuable to the business, terrible conversion rate.

Aaron

So then we move up to scale, and we add on appointment links and call transfers for 99 a month and more minutes, of course. Right.

Jordan

But what are those? Those are more human like receptionist features. So what we have learned about this business is effectively that the base plan is a message taker, and the premium plans are more of a receptionist.

Aaron

K. So then we move up to growth. So we've done $49.99 at $1.99, get a bunch more minutes, same stuff. And then you add on live transfers coming soon

Jordan

Yep.

Aaron

Training files and custom agent training.

Jordan

That's right.

Aaron

We add on it. We add on a few specialized things at the $1.99 plan.

Jordan

Right. Where they start to get a little less self-service and a little bit, Hey, we're special, and we have all these PDFs that we would like to add into this agent's context window, and we understand AI. Okay. So the process, right, big up top, then narrow, and then wide, and then the key thing that was so exciting to kind of watch unfold was we had those premium features for about six weeks, but you couldn't see them. And the only way you saw them was if you pinged us and you talked to support, and we would say, yes.

We'll reveal that feature for you. And what we knew along that six weeks is we understood how people use the product, what the base plan was, what the right pricing was, what the premium features, which premium plan a feature should live in, all that. And then somewhere around where are we? March February, we introduced what we called the premium UI. Okay.

So we took the features that were hidden. We revealed them in the admin, but we made sure that the user could tell what a premium feature was and what a base speech was.

Aaron

So there's a little indicator that says, This exists, but you don't have it?

Jordan

There's like color and icons. And so you make the promise in describing the feature. And then if you want to use the feature, we shot away from any like dark patterns on like, you can set the feature fully and then we hit save. That's when you get a credit card model like it's annoying. So we did it very cleanly, white hat, let's call it.

And that has changed our average revenue per user by like 20% over the last four weeks. Wow. Right? So it's like all the features, just the basic features, call that the base plan, expand out into these premium plans, and then reveal all those features so that everyone comes in at the base plan and more and more people are enticed to come up into what looked like a $49 a month product. We now give them the option to get more value if you're willing to pay more with these additional features.

And that has changed the math around our advertising, and now we're now we're in hit the gas mode.

Aaron

So what would you call this hourglass strategy? Because it sounds to me like some sort of discovery. I don't know if it's pricing discovery or product discovery, but it's some way that, like, you went to the market with a bunch of ideas, and the market said these two or these three. Yeah. But then you didn't lose all the other ones.

You just narrowed down scope and focus, and then you brought back the other ones later. So, like, if you had to give your hourglass strategy a subhead, like, what's what's the h two? How how do you describe this strategy?

Jordan

It's like feature set development. Something around that? I mean, remember, these are all these are all lies. These are lessons in hindsight. This is not me being a genius in August and saying this is exactly how things will unfold.

Of course. Yeah. This is well, this

Aaron

makes sense. An emergent property that you have discovered Yes. Which is what makes it so valuable. Right.

Jordan

And I think maybe that is my favorite part

Aaron

of the job.

Jordan

I am a a a shameful ideas guy. But if you if you have good ideas, then, okay, then then it's fine. And so I think that guiding that process from being one step removed from talking to customers every day and creating content every day and kind of sitting back and thinking was the most valuable contribution that I could have made over the last few months by just noticing and just admitting, oh, that's actually not necessary. Only people using this. And this looks great, but it's not good for us to build this way because everyone's converting, but they're not actually using.

Aaron

Mhmm.

Jordan

So I don't know what that is. Maybe being I

Aaron

don't either, but you gotta you gotta write it because this is good. This is a good this is a good framework. We like a framework, especially one that has a name, especially one that has a visual too. So you gotta you gotta write this.

Jordan

If anyone could come up with a better description than hourglass, please let me know. Because I I think I I don't know. I called it barbell. I wasn't sure. Dumb I I didn't know what to call it.

I'm I'm on hourglass. If anyone has a better suggestion, please hit me up. Because we do we need to brand this. You know? It needs to be Yeah.

Aaron

And I've I've had expand and contract, for certain things in my life, but this is a three step. Like, you you start expand, then you contract, but then you go expand again. So it's not quite as I call

Jordan

it accordion for a bit, but that I don't know if anyone knows.

Aaron

Yeah. Yep. Yeah. I don't know. Probably not gonna hit the youth with accordion.

Yeah. I don't I don't think they'll get that one. Yes. I wanna hear so how much time do you have? I have a lot.

Time? Yes. I wanna hear, I wanna hear about this ad strategy. Well, actually, first first, I I feel like you are in the bootstrapper circles, but you're not afflicted with the same, the same problems as bootstrappers, which is, shame around, like, selling. And so I wanna hear, your cold outreach strategy because I think most, you know, bootstrappers are like, oh, I can't send emails to people.

Can you imagine? Mhmm. And then I wanna hear your paid ads strategy because that did you say that's the thing that's, like, really starting to take off? Yes. Okay.

So I wanna hear about both of those both of those strategies from a non mired in the bootstrap person. But before we do that, this podcast is brought to you by Laravel Cloud, the best way to ship and scale Laravel applications. You can find that at cloud.Laravel.com. Thank you to Laravel for sponsoring the show, and this show is sponsored by Stream at gitstream.io. Stream, scalable APIs for chat, video, voice, feeds, and moderation at gitstream.io.

So thank you to Laravel and Stream for sponsoring the show.

Jordan

Okay. I wanna make comments about the sponsors, but we're gonna keep going.

Aaron

We're gonna keep going. We'll keep going. Maybe we can do it at the end. We can do an errata at the end. Let's keep going.

Jordan

So the bootstrap ideology issue

Aaron

Mhmm. Is I've put that in my rear view mirror.

Jordan

I got over it a long time ago. I hope people I mean, they seem to be less ideological now than they were five years ago.

Aaron

That's part of what made y'all show so great, was y'all had different ideologies, which is Yeah. I love listening to that.

Jordan

Yes. I like ideology. I think it's important. Mhmm. But my my guiding ideology is after tax money in my personal bank account.

That that is my actual ideology, and that is the god that I pray to.

Aaron

Okay? And it just that is not the god I pray to, but I do like that ideology, just for the record. I just want the record to be clear. Yes. Directionally correct.

Jordan

How you get there is is less ideological. And so so, yes, I I I think people do should do whatever they need to do, whatever they want to do, in order to increase the after tax money in their personal life. I happen to raise money for rally, and that that's just a different way to go in business. It's just different approach.

Aaron

And so You mentioned earlier 18,000,000. Is that what you raised for Rally? I mean, if you're not able to be public about anything, that's fine. But you said earlier 18,000,000.

Jordan

Stuff is public because it needs to be filed. But, yes, we've raised 18,000,000 to Rally, and Rosie is a pivot out of Rally.

Aaron

Okay. And have you been public slash do you want to be about where you were in your runway when you pivoted to Rosie?

Jordan

No. I've just said several million dollars. Okay. Okay.

Aaron

Alright. Carry on.

Jordan

Right. So we we basically had enough runway for, I don't know, call it eighteen months or something. Okay. So part of a very critical part of my job is to look at a spreadsheet and understand that I am better off spending money on customer acquisition than not. K.

It it is literally mathematically worse off to be very tight on customer acquisition because the majority of the money spent is on people and software.

Aaron

K.

Jordan

And so to add on a little bit of expenses, that makes a big difference in your revenue growth, that makes a big difference in your burn and your runway. It is, like, mathematically better to spend money on on customer acquisition. So I have, like, internalized this. I come from the bootstrap world where it was very, how do I make something with very little?

Aaron

Right.

Jordan

And then I went toward, like, partnerships and and that type of thing that don't cost money. In this case, it was like, well, you need to spend money. So let's just hire a great consultant and fire up the cold email because that is the simplest way to go from where we are today to making 500 people a day aware of our software. Just the most straightforward way. And so that's what we did.

We hired Brian Schackman, who runs a service for he runs his own SaaS, but he also on the side runs a service for cold email. And cold email these days is a bit of a science.

Aaron

The domain and the domain

Jordan

warming and the inbox warming and like, it's intense. At least there's great software to make it work, but that's not enough. You do want someone who knows what they're doing with it. Otherwise, you will just fall into every single possible trap.

Aaron

And burn your domain forever.

Jordan

Yes. Yes. And all those things. So that is what I saw as a, the most straightforward way to make 500 people aware of us every day, and, two, if it worked, a very easy channel to just hit the gas on and double and double and

Aaron

double. Totally.

Jordan

It did not end up working. K. Maybe we'll try again in the future. Maybe it'll work better now. But when we did it, it didn't quite work.

It did the job at getting enough people in our inbox and in our funnel to just learn the product better.

Aaron

But long term, the economics were just not there. Yeah, that's right. The customer growth, it just wasn't there.

Jordan

But it did its job. And so it gave us that first cohort of like 20 ish users, and it just helped

Aaron

them

Jordan

talk to people and understand what they were saying. And I mean, this was a new business. I'm barely learning the lingo around telephony and around phone and all this stuff. I come from a small business universe and like my family business. So, I'm in touch with it.

It's not like I'm completely out of touch with it, but I still didn't know what we were doing. So, the cold email strategy was relatively blunt force. How do we just get people, into our phone? There isn't that much more to say about that other than it worked. We probably spent, I don't know, $25 over the span of, like, two, three months and just got people To

Aaron

get 20 people?

Jordan

Yeah. Yeah. Yeah. To get 20 users. You know, we talked to a lot of people and dozens of people, but the actual value of it was this first cohort of people that actually told us what they needed.

Aaron

And did your guy do all the lead lists? Like, did he find all of that, or is that something you had to do?

Jordan

No. He did everything. Okay.

Aaron

That's cool. It was it was That's great. It was great.

Jordan

And it did exactly what it needed to do, and it accelerated our learning, which makes the 25 k, in retrospect, relatively meaningless if it saved us three months.

Aaron

Yeah. Big time. Three months of salary and

Jordan

And, you know

Aaron

That's right. Infrastructure and all the dollars and everything. Yes. Yeah. Okay.

So that that worked in a way, but wasn't, like, the thing you needed. So then you moved on to ads.

Jordan

Yes. And my my hunch was that we are in b to b, but this should be marketed a little bit like b to c.

Aaron

K.

Jordan

And coming from the Shopify and e commerce universe, I really admire the advertising and marketing of these direct to consumer customers. Yeah. They are they're they're so good at

Aaron

making the art.

Jordan

This is so embarrassing. I don't even know if I want to do this.

Aaron

What is that? Yeah. Of course. It's great content. What is it?

Jordan

I'm I'm so I can't believe I just did it. I'm so embarrassed. These are the squeezy things you put in your cheek to bite down and build up your muscles in your jaw. Okay?

Aaron

Oh, wow. You're going for UltraChad. Yes. Okay.

Jordan

Yes. God damn it. That's so embarrassing.

Aaron

Hell yeah.

Jordan

Good. It's honest. Okay?

Aaron

Yes. It's good content.

Jordan

Here's the thing.

Aaron

These marketers Greco Roman. God.

Jordan

These marketers are so good that they convinced a 45 year old dad, one dad of three, that he needs his jaw more defined. Okay? Goddamn it. Aaron. Okay.

We're gonna move forward. We're gonna just gonna take the lesson out of it. Okay? So what I Fantastic.

Aaron

I I You look great. So it's working. Congrats. Yeah. There we go.

Huge. Huge job. Amazing.

Jordan

Okay. So I found an advertising company that did ads for direct to consumer companies and did ads in

Aaron

such a

Jordan

way that the goal was that the ad looked and felt native to the platform. It looked like user generated content. It looked natural as opposed to a polished perfect advertisement. That's thirty seconds exactly. It was, you know, a guy at his desk saying, I got sick of showing up on Monday and checking my voice mail, and everyone just hung up.

I knew how much money I was losing. So I got Rosie AI, and now she answers my phone and takes my messages. I never miss a call, and then he listened to it. Oh my god. She sounds so human.

I love it. Go to Rosie AI to start your free trial.

Aaron

Okay? And they shot the videos. They they did all of that?

Jordan

They do all of it. They so we do an interview. I explain to them the product and the benefits and the features and all that stuff, and then they come

Aaron

up with scripts, and I make adjustments to the script.

Jordan

And they're very scientific. They are this is our our it's called hook.

Aaron

In the

Jordan

first ten seconds. And we'll try these three. And this is the body, and then this is the conclusion slash offer. And then let's mix and match all three, and let's see which one works. And then let's get a different creator and see if that works better.

And they have just been optimizing this thing for months, and it is working so well. It's awesome.

Aaron

What platforms? Instagram, TikTok?

Jordan

So Meta as an umbrella for Facebook, where a lot of our ICP lives, and Instagram. And then Google, which is YouTube, and then some right. YouTube, like, video, and then also YouTube has some static placement also. Okay.

Aaron

So those two

Jordan

Man. And and And

Aaron

so they found they found one or a few that worked, and then Slack just started popping off. The channel just started blowing up.

Jordan

Started blowing up? Absolutely blowing up. And then we were like, okay. What happens if we spend a hundred bucks a day? Right?

What happens if we spend $300 a day? So, like, 9 or $10 a month. What happens if we spend thousand bucks a day? What does it look like then? What happens if we spend $2,000 a day?

We were, like, just testing, and the ratio just stayed consistent.

Aaron

It held?

Jordan

It just held. And and then a few weeks ago

Aaron

You got a money printer.

Jordan

We got a money printer. That's right. Oh, man. So so one of the guys from the advertising company comes up to me, and this is partly why I love them. First of all, I met this this guy who runs the advertising company.

He's like, I'm gonna be in Chicago for a conference. You wanna have lunch? Do we have lunch? And I'm like, okay. I need to understand.

How old are you? He was like, I am a sophomore at Stanford. Stop. And I'm in between classes right now running this business. I was like, damn, kid.

Damn. What? Yep. Yep. Awesome.

Aaron

The CEOs at a at a conference in Chicago, you go to lunch with them, and Young kids, like, he's a sophomore.

Jordan

He's a sophomore at Stanford. Yeah. His name's Hamza. He runs a company called Newform dot ai. These guys are very smart.

I was track attracted to them by their content.

Aaron

I thought, like, what are we doing? I don't know. I don't know.

Jordan

I don't like it. I need more after tax money in my personal bank account. Okay? That's what that's what I'm doing.

Aaron

Oh, man.

Jordan

So he comes up Say

Aaron

the name of the say the name of the agency again. Newform.

Jordan

Newform dot a y. They're great. They are not cheap, but this is what I should be doing. And one of their one of the the the guy who runs my account comes up to me and is like, Jordan, what do we need to do to get you to 10 k a day?

Aaron

Oh, brilliant. And I'm like, okay.

Jordan

I'm like, that's ridiculous because that's $300,000 a month. And and Yeah. And what are you talking about? And what it did is it challenged me. It just said, why not, dude?

Why not? And so I went to my spreadsheet. And let me be clear. We are not spending $10,000 a day. But it challenged me to explore what the limits are as opposed to thinking like a bootstrapper that maybe we thought five years ago and thought, oh, I can't

Aaron

spend this.

Jordan

I can't spend worth a thousand bucks a day. It's crazy. So now all of a sudden, we find ourselves in this very interesting position where we're like, I guess what we need to do is find where the diminishing line is.

Aaron

Right.

Jordan

And and we're pushing pretty hard this month, so we might find the diminishing line. But while we explore that, it's time to get organic content going, which is why I started investing in organic, you know, in SEO a month ago and then the podcast and everything else because we are gonna find the diminishing line.

Aaron

Sure. We

Jordan

don't wanna be entirely reliant on ads forever. Right? Twelve months from today, I would like ads to be a minority of our lead of our lead flow.

Aaron

Mhmm.

Jordan

But for right now, it's really an interesting challenge of, like, hey. You built a system for self serve software that allows a painting company, a dude in a truck, to onboard and have a voice AI answering their phone in under ten minutes. And so that is the advantage to lean into because our competitors right now are like, you know, sign up for a demo and talk to us. Look at all the models that we have and all this power, and we're like, that's the

Aaron

They don't freaking care about the models.

Jordan

No no one cares. Exactly right. So, you know Oh. I know it's an interesting kind of spot and problem, and we're not on the we're at the promised land yet. We're not profitable.

But we understand, oh, we have an interesting year to go through to figure out where these limits are and how much we should invest in each thing and how do we keep track of cash and how do we lower our

Aaron

Right.

Jordan

Our margin because cost of goods sold in AI voice is a challenge these days. It's still expensive.

Aaron

Actually have some cogs that are hung.

Jordan

You have some cogs. Yeah. It's kind of an interesting problem.

Aaron

Wow.

Jordan

But here we are. So now now right? Like, what what an egotistical animal I am that now that everything's working and humming, I'm like, you know what I should do? I should go talk about

Aaron

it. I should go start a podcast. Oh, dude. This is amazing. This new form, like and the idea of going to a DTC advertising company for your, you know, app is it is b to b, but it's kinda prosumer because I bet a lot of them are, like, solo operators or, like, small shops or something.

Jordan

One to three person companies.

Aaron

Yeah. The idea to go to them yeah. Because all the logos on their on their home page are all Direct to d c. Team. It's all BlueChoo, Kajabi, a Prisma.

It's like all these things that, you know, you've heard of.

Jordan

Yes.

Aaron

This is great. This is this is genius. I love this. And you got a money machine. You put some in at the top and more comes out at the bottom.

That is the dream. It it is I have been pursuing it for years, and I couldn't get it.

Jordan

Rally just didn't work that way. Rally was like, doesn't matter what you spend. You need to go meet these people at conferences Right. And get into their three month sales process and convince them And

Aaron

then their eighteen month migration.

Jordan

Right. Right. So I a lot of a lot of Rosie's attributes are directly an overreaction to the pain from Rally. Like, no enterprise, self serve. Not complicated.

No platform to rely on. So, like, all these things are, like, maybe I'm making a mistake by just overreacting in all these different ways, but maybe it adds up to just being a better type of product to, you know, to sell.

Aaron

Well, it sounds like it's working. Are you getting Steve and I have talked about being able to buy ads. We I don't think we would do, you know, video ads like this, but we've talked about being able to buy ads and, like, the ancillary benefits of it is you're spending a ton of money, so then you get all these credit card. Like, you get either cash back or you can fly first class anywhere you wanna go. And I'm like, I'm flying first class to Boise just to hang out with Steve before, you know, if we're buying ads.

So are you getting like, are you playing that game too with, like, trying to optimize that part of the spend?

Jordan

I am. And that is, like, a dark, corner of the venture capital world that all these founders spend their company money, and and

Aaron

and they they collect the points Personal benefit.

Jordan

Because because it's on your card with your name. Yeah. Because it should be. It shouldn't be on someone else's card at the company. You need to take responsibility.

But the, you know, the result is a tremendous number of credit card points. And if you use Chase, you will get three x when you spend money on online ads.

Aaron

Good lord. Yes.

Jordan

So there's a limit on that. Looks like it's only 450,000 for the year or something.

Aaron

I'm okay with that limit. Yeah. Same. Same. That's fine.

That's fine with me.

Jordan

You you wanna hear a question?

Aaron

You could you could get into a tail wagging the dog situation there pretty easily. Easily. Well well, look. You know, that that's not that's

Jordan

not like the any reason to change behavior in any

Aaron

way. Yeah.

Jordan

But we what we were using the advertising company, they were buying the ads, and then we were reimbursing them. And at some point, I was like, okay.

Aaron

So why don't we just put that card on card on card? Yeah. Totally.

Jordan

That is boy scout compared to someone I used to know who ran a company that bought tickets for, like, Broadway shows. That's what the company did. But the way the company actually worked is is that the company would buy the ticket and then resell it to the person buying it on the marketplace. So this company was very big and very successful, and all of the volume went through the founders' credit cards. Millions and millions of points.

Yep. So whatever I got going doesn't hold a candle to that operation. That was a full fledged that was a hack.

Aaron

Oh, man. Sometime when we're not recording, I wanna hear more about the dark sides of VC that you have seen. I would love to hear that. I'm sure you've seen some stuff.

Jordan

Yeah. Everyone knows the the the dark side of VC. You're using other people's money to benefit yourself, but, it doesn't really work unless you benefit others.

Aaron

It it

Jordan

is it is a capitalist alignment. It's beautiful, actually.

Aaron

It's pure it's pure capitalism.

Jordan

Pure capitalism, there is one problem, and that is your liquidation preference.

Aaron

That's that's

Jordan

your problem.

Aaron

You you got I need

Jordan

to sell for more than $18,000,000 before I see a dollar.

Aaron

Right. That's my that's my problem. $1,818,000,000 is a lot of It's it's a

Jordan

lot of millions.

Aaron

It's a big number. It's a big number.

Jordan

Right. Relatively speaking, a a big a big number. Wow. Tacos.

Aaron

Fascinating. Man, this is great. This is a this is a look into, you know, Ian and I are both I think Ian's more business dad, but I'm still very much in, like, the bootstrapper mentality because Steve and I haven't raised any money. Yeah. And seeing hearing all of these, like, I don't know if it's pejorative to call them proper business, pejorative to myself.

You know? This is like proper business stuff. Yeah. I I pay money to find a channel and then pay more money. Yeah.

That seems obvious.

Jordan

There's a spectrum. You know? And I talk to people who are I'll go to March Capital. That's our lead investor. I'll go to their, conference in in LA a few weeks ago, and then I come across people, and I'm like, oh my god.

I am playing around with toys over here in in the corner compared to what what these other people They pat

Aaron

you on the head and say adorable dresses. Meeting next year,

Jordan

you'll you'll be on stage, then you can talk about what you're doing when that it's actually interesting. So I think it's just a spectrum. It's good to be exposed to all of it. Aaron, what is your business model?

Aaron

You know, Jordan, that's a good question. So let me I I I'm I do want I do want all of your thoughts. You've listened. Okay. You followed.

I do want all of your thoughts. So here here is, here's our current business model. We make educational material, and we sell it. Mhmm. That's it.

That is the current

Jordan

business model. Partnership? You you and Steve?

Aaron

Me and Steve. Yeah. K. So Steve and I Steve and I own the business. We're full fifty fifty partners.

We make educational content and sell it. That's it. Cool. So that is, like you know, we can talk about it for an hour, but that is the business model. Yeah.

Individuals and sometimes companies give us US dollars, and we give them, basically, video courses. Yeah. That's basically it.

Jordan

I remember when you were transitioning out of

Aaron

Uh-huh.

Jordan

A full time role.

Aaron

And I was transitioned. You're kind. But I was transitioned out of a full time role. That's very that was very, deft of you.

Jordan

I don't necessarily see that. I think when people quit their job, it's a a congratulations is in order.

Aaron

Mhmm.

Jordan

I think when people get fired from their job, you just have to hold off on the congratulations for about six months.

Aaron

Or because

Jordan

you can't say congrats right when someone gets fired because that sucks. Right. Of you.

Aaron

You know?

Jordan

But but maybe six months or a year later, you're like, was wasn't that a good thing? It was almost certainly a good thing. Yeah. But I remember I reached out to you

Aaron

Mhmm.

Jordan

And it's almost like my capitalist instincts kicked in. I saw you as undervalued. I was like,

Aaron

oh my god.

Jordan

This guy is gonna make a million dollars a year very very soon because of the quality of both the content, the education, and most importantly, the strength of the relationship with the audience. So it makes sense that that is your business model now. And I Yep. And I still firmly think you're you're gonna do incredibly well with it. Do you wanna expand beyond education?

You know, almost like the way Adam Wathan has gone into product in that way. Brian also toward that. Mhmm. Mhmm. Education feels like a very, several steps up the value ladder in terms of when you love me and you wanna pay a larger amount, that's when you go toward this educational content.

So are you thinking about filling in the other steps in the ladder?

Aaron

Yes. So that's the first of all, thank you. That's very kind of you to to say that. But, yes, that is that is the existing business model is sell, what we believe are extremely high quality courses to people that know, like, and trust us. That has been very good.

I mean, the first year in business, we've made enough money, which is like, you know, that's kinda hard to do.

Jordan

So No joke.

Aaron

Last year. We did it. Yeah. And now I think, so if there is, like, a if there is, like, a a spiritually aligned business, I think you might have heard of this one because it's in the AI space. It's Every.

Have you heard of Dan Shipper and Every? Yeah. So they've got Lex dot page. They've got Sparkle. They've got a couple of products, but then they have, like, their blog, and they've they've got, like, a podcast, their whole thing.

So that is one that is close. And then, I think to some extent, Tailwind is close, but slightly different. And so what they what what I am seeing for our business is we have distribution, which, as you know, is incredibly hard to come by. Yes. Right?

And so we have it. We have distribution. We have people that trust us, and I take that very seriously. And so then the question becomes, like, what else like, where else is the value, and what else can we offer? So I think you're correct to point out that education is pretty far up, up the chain of, like, they really know me, and so they're willing to spend 203 hundred dollars on a course.

Yep. How do we move down? So things that we are exploring actively right now, one is we are redoing, this is still education, but we're redoing Screencasting.com to offer a much broader, spectrum of of courses. So I'm doing the main one. Steve is doing premiere.

We hired a guy to do final cut pro. We hired somebody to do DaVinci, OBS. So, like, we've hired, on a contract basis. We've hired a bunch of people to make a bunch of courses on screencasting. And so part of the play there is can we can we expand to a sort of, like, truly a studio?

We're called TriHard Studios. Can we expand to, like, a studio model where we've got a cast of characters that are all teaching this one specific thing? And I think we can. And that will that's an experiment that we'll see, hopefully, come to fruition this month. I think another question on education, and then there are products.

Another question on education is, I am I am given to wanting to educate people who are intermediates and, like, level them up into being advanced. Like, I want to take people that want to learn and want to know things, and I want to, like, I want to enrich and edify their lives by saying, hey. Here's all the hearts. Keep going. Look how cool this is.

Yes. Yeah. I love that. It's everything is shaped like a pyramid, and the intermediates are way up here in

Jordan

the pyramid.

Aaron

Right? And so there are just fewer of them. Yes. And so our next our next pure database education experiment is what if we did an intro? Like, what if we just taught an intro to SQL course?

Okay. Because there are tons That's right. Of those people. That's right.

Jordan

It's very

Aaron

So can we sell it for less? And, like, then is the is the burden of knowing me also quite quite lower. Right? Okay. Okay.

Mhmm. And then I'll hit I'll hit you with one more. Yep. And then and then we'll get we'll get a a smattering. Yeah.

So outside of pure video education, Steve and I talk a lot about this idea of, pointing many experiments or many projects or many ideas in the same direction. And so, our internal shorthand is are the vectors aligned on that? So, like, if you're imagining thrust vectors, we are a spaceship. Are all the vectors, like, pointing the same way such that we're making progress? Great.

Right? We like Better off. Great. Yeah. And so, that doesn't, of course, mean that we always have to do video courses.

That may mean there are products available in the video space that, like, our videos will help the product, our product will help the videos, our content helps all of it, and that can push us to the right direction. And so I think as we have been running this business for a year now I mean, last week, I guess. As we've been running it for a year, some product ideas are starting to emerge that are directionally appropriate for what we're already doing. It's not just like, hey. Let's burn down all this goodwill we have or just not even burn it.

Just, like, leave it aside. Yeah. And try to build something crazy that doesn't apply to anything. Yep. And so those are kind of you know, we've got the studio, we've got the down market, and we've got the, forthcoming, products in the same space.

So Yeah. Take your pick.

Jordan

Very interesting. I I like what happens, to all of us as we get further into business and and Mhmm.

Aaron

And a

Jordan

lot of these things that you really can't think about too much when you start you you do start start to digest and be thoughtful about your effort. What I heard in there, by far, by far, the most important thing was hiring someone else to do a course because that begins the journey toward making you less necessary

Aaron

Mhmm.

Jordan

And less critical. And I think that's where we wanna go. And you can be you know, Jason Fried is not necessary in his business at all. What he's doing right now is because he wants to. Mhmm.

And I think the answer is not get out of your business so you can go sit on a beach and do absolutely nothing.

Aaron

Don't want to do that. But the

Jordan

goal is do what you want to do. And in order to do that, you do need to make yourself less critical.

Aaron

Mhmm.

Jordan

And so you can rise up toward the things that you love the most. Right? I think it's someone of genius would be the the term. So I I I think it's great. All within a year, you're identifying these vectors and where to put effort and starting to identify, hey, what what does it mean to be a studio to go beyond me doing everything and selling everything?

So it feels like you're on the evolutionary path. You are going exactly where the business needs to go. Yeah. The distribution and making sure that you use that to the fullest extent possible Mhmm. And not start from scratch unless you become really good at building new audiences.

Yeah. So I guess that transition toward, the lower part of the pyramid Right. Tricky. It makes sense. It makes sense.

The the nice thing is that you do have the next step up ready Right. For them.

Aaron

Yeah. And that's something, like, that's something that, like, we we think about a lot is kinda like the portfolio thing. And so, you know, you'll you'll hear Rob, and I think correctly, Rob Walling will correctly say, like, don't do 12 startups in twelve months. And it's like, okay. Yeah.

You know, that that's fine. And then you hear other people say, like, just throw everything against the wall and see what And it's like, I don't know. There's gotta be there's gotta be somewhere in the middle. And I think some of that comes down to personality. Right?

So I think, like, Matt Wintzing, of whom we both know and love, is like, I am going to just keep going on this one idea, and I'm going to make it work. And then Peter levels is like, I made a VR flying game and also, you know, Nomad List. It's like, what's going on?

Jordan

Yes.

Aaron

But I think for Steve and I, we're trying to really think about the cohesiveness of the portfolio. And we want, like, every product to work well with other products. And so having an intro to SQL at 39 or 49 is good because then they can do mastering Postgres after that, Or somebody can stumble on mastering Postgres and say, I'm not I don't even know what Postgres is. Oh, these guys have intro to SQL. Let me do that one.

Yep. And the same idea goes with the screencasting portfolio, which is like, you come, you take the how to screencast course. And then once you're done, you gotta, like, you gotta get better at your editing tool of choice. And turns out, you don't have to go anywhere. We've got courses for that.

We've got six different courses on editors. And so instead of, like, you know, instead of trying 12 different things, we're trying to do portfolios of related things that feed on each other.

Jordan

Right. Even if an individual product inside of that portfolio isn't a standout hit, it contributes.

Aaron

Yes.

Jordan

And then it makes it more likely that when there is a hit, it also contributes to the larger pie in general. Yes. Yeah. We this reminds me of the experience that we are we are having right now since launching the premium UI and understanding how quickly people upgrade. What it's making me actually think is I should probably lower the price in the base plan.

Mhmm. Because the more people that come in at the entry point, the now that we feel confident in upselling them and upgrading, not that different from yours. Right? You can you should not do a AppSumo deal with your core Screencasting.com.

Aaron

Correct.

Jordan

But you can do it with your 39 or $29 Mhmm. Course on on introductory SQL. Right. Because that starts to become a way to kind of grow your leads, which is what I'm identifying as our base plan. It's actually just for selling our leads.

When when our investors challenge me and they say, what about the enterprise? What's going on up there? I say, well, look, there's different forms of enterprise. We don't want it. American Airlines and, like, Wells Fargo Bank, all of those miserable phone systems are all

Aaron

gonna be

Jordan

replaced with AI. Great opportunity. I want nothing to do with it. Yeah. There's a different form of enterprise, which is we're a franchise, and we have 800 locations.

So we need 800 Rosie accounts. Can you help? So I also don't love the idea of going and hiring an AE and doing the sales process in that way. What we're seeing in our introductory base plan is that the individual franchise location signs up for that. Mhmm.

And then we form a relationship with them and we identify as soon as they come in. Oh, That's different potential than the others because it's attached to a network of 800 locations. Right.

Aaron

And you you can't do that. You won't see that opportunity if it's too hard for them to get in. And so I think what you're experiencing right now is you you do have some of

Jordan

the best people, as customers. They they're they're influential. They their word-of-mouth has more strength than the beginners, all that. But if you're missing out on that bottom of the pyramid, you are not only missing out on this revenue that moves up your ladder, you're just missing out on opportunities that you just would not have come across. You just didn't know about.

Aaron

Yep. Yeah. So in in a sense, with your base plan, people are paying you to join the upsell funnel.

Jordan

Yes. Which

Aaron

is pretty crazy. Yes.

Jordan

What what they're really doing mathematically is they're helping us recover our ad spend, our

Aaron

CAC Mhmm.

Jordan

To to provide us with more opportunities that might be, you know, significantly higher than the average revenue per user.

Aaron

Mhmm.

Jordan

So, if we spend, you know, if we spend $50,000 in a month and it brings in 15 ks in MRR, that's great. But in the future, that MRR should be should expand beyond what it looked like in month one or two because of the upgrade path. So your business seems not that dissimilar.

Aaron

Okay. So let me let me let me throw this one at you. We in my in my opinion, my humble opinion, we've done the hard part. We've got we've got distribution. We've got these flagship intermediate courses that are, like, incredibly hard to produce because they it's just a freaking slog.

And so we've done the hard part, and I think, I I think what I am learning now is we need to we need to do some we need to do some business. It's business time. And so what I spent last week doing, in addition to recording videos, what I spent last week doing was exploring checkouts, which I know that I know you're gonna start twitching, but I explored all the checkouts, and they all suck.

Jordan

Okay. Why are you exploring checkouts? How So

Aaron

let me let me tell you. Yeah. So, we are in this process of, editing all these screencasting videos. So we're gonna have a bunch of different SKUs on Screencasting.com. Okay?

Historically, we've had, a SQLite course, single SKU, mastering Postgres, single SKU. We did do a guest course with, an instructor on Ruby on Rails plus SQLite. And at that point, it was like, oh, okay. We gotta get a bundle going, obviously. Yeah.

And so we, like, you know, we kludged together a bundle on our payment provider, and it was like, yeah, it worked. But we noticed or we saw bundle pricing works. We're discovering things from first principles here, but we're getting there. Bundle pricing works. Now we're in this place where it's like, alright.

Screencasting.com is going to have, maybe six, seven different courses. Also, it's going to have digital downloads. It's gonna have assets. So you can, like, hey. I wanna buy a plug in for Final Cut Pro that does this thing.

And so we're at this point where we're gonna have, you know, fifteen, twenty products on Screencasting.com. Yep. And we need to be intelligent about cross sells, upsells, downsells, bundles, the whole thing. Because what I don't wanna do what I don't wanna do is, like, pour a bunch of people into the top of the funnel, and the funnel is just completely leaky and totally Right? And so we're going from click a button and you go to a hosted checkout with one product to click a button, you land on an interstitial.

Hey. You might you might like these products too. And by the way, you know, we're 20% off right now. Right? Get them both.

You'll need them to Yeah. Yep. Get them both. And then, you know, percent off right now. Right.

Jordan

Get them both.

Aaron

You'll need them to Yeah. Yep. Get them both, and then you're redirected onto the checkout. And so, you know, we're trying to figure out the engineering behind getting that to work. And Jordan, is is bleak.

Jordan

It's it's bleak. Still bleak. It's crazy.

Aaron

It's it's still bleak. Awful. Yep. So I I explored headless Shopify. I know that those are two words you don't wanna hear.

I explored I explored Shopify headless. I see. By the way I

Jordan

see that as an oxymoron, but but continue.

Aaron

By the way, whoever's running naming at Shopify, I don't know what hydrogen and oxygen are. You're in your docs, and you're like, well, if you're using oxygen well, if you're using hydrogen, I'm like, give it a name. Like, I don't know what that means. At least

Jordan

make it a hyperlink. You know?

Aaron

Yeah. I know that it's like a play on liquid, but, like, it doesn't mean anything to me. So I explored Shopify headless, sucked. SamCart sucked. Bolt, couldn't even get anywhere with it.

Like, had had to, like, have a call with somebody, and I went in there and there's no product. I can't even, like, add a product. Yeah. Yeah. Sucks.

Yeah. It's Checkout page. I think it's just checkoutpage.com or something like that. Tried that. The very first screen that I got you on checkout page was a video from the founder saying, hey.

You know, here at checkout page, we're not you you don't actually add a product. You we don't have the concept of products. You just build checkout pages. And I'm like, well, that's not gonna work for me. I've got an inventory of products, and I want you to figure out how to upsell them Yeah.

Based on what the customer is buying. Yeah. So it's super bleak. And you know what we did? We went down the stripe.

The just the Yep. Raw stripe. And so we're just gonna build it all ourselves, which sucks.

Jordan

It it's tough. I I wish I I could even put you in the right direction because SamCart comes close.

Aaron

It does. It comes close. It's ugly.

Jordan

It's yeah. It's for marketers. They're actually great marketers to pay attention to.

Aaron

Yeah. They're I I noticed that. I read all the emails. They're very good.

Jordan

Emails, video sales letters, retargeting. They're all they're very, very good at it.

Aaron

And they've got all the in the big info product people Yeah. As testimonials. Right.

Jordan

Because all the big info product people are not technical, and so SamCart was built for them.

Aaron

And all they care about is, like, funnels. And that's where I need to get because I'm on the wrong side of this question right now. Well, depending on judgment. You wanna be calm. I'm on a side.

You wanna be calm. A side.

Jordan

Of your checkout.

Aaron

I I do. And I wanna be, like, I wanna be super proud of the product. Like, I don't wanna just throw together, you know, some product and then do an upsell for $9.97. Like Yeah. And I need to move more towards, you know, pure capitalism.

But

Jordan

Somewhere in between. Sure.

Aaron

Yeah. Exactly.

Jordan

Yeah. I don't think you're gonna do better than Stripe because Shopify is intended for physical products, and all of the logic is for physical products and trying to, you know, fit that square peg into a round hole around digital, and it's just it it rarely works.

Aaron

Yep. Sure didn't work for us. Nope. Yeah.

Jordan

No. Yeah. I

Aaron

Kind of kind of a disaster. So where we're at now is, I'm I'm building it all with Stripe primitives. And, basically, we've got a bunch of Stripe products, but we're not using Stripe checkout. So we've got a bunch of Stripe products in the Stripe dashboard. Okay.

And then on our side, you know, we have a Laravel app. We're syncing them all down. So a user will click buy on a a course or something. They can click add to cart, but let's just go down the buy route. They'll click buy.

They'll go to an interstitial page hosted by us that knows what they already have, what they're buying, and what else is available, and what offers are, like, we've configured on the back end. And it'll say, hey. Do you wanna add this on for this amount? Whatever. Yes.

And then we redirect them basically basically to a hosted checkout, but it's using the Stripe payment links. Okay. Product instead of the hosted checkout.

Jordan

Or using element on your own page?

Aaron

No. No. No. It is, it is, the checkout is actually hosted on buy.stripe.com. Okay.

But it's not

Jordan

it's not the Stripe checkout.

Aaron

It's not the customer portal. It's, like, here's a payment link that I have constructed via API that has these prices and this shipping, and, like, now go and check out on the stripe.com. It's so

Jordan

It's annoying that you have to do that because that's not the business that you're in?

Aaron

Yes. Exactly.

Jordan

I think I think what you're describing is learning what business you're in.

Aaron

Yes.

Jordan

And and the it's amazing that you have so much ready. You have all like you said, you have the hard part done. Yes. So I I do think you're you're right to look at it and say, okay. If we have the hard part done, maybe we should stop building hard parts.

Aaron

Yes. And That is exactly the conversation we had. Great.

Jordan

Great. We we have a different version of the conversation. We just know more about our business now than we did in the beginning. Mhmm. And what I'm understanding in our business is that we are, we're an onboarding company.

Mhmm. We we are a gateway. There is an enormous amount of demand for people to solve this problem, and our job is to solve it for them in a way that they're actually gonna accomplish.

Aaron

Mhmm.

Jordan

So whenever I go to a competitor and I'm like, you know, you get that weird feeling in your stomach, like, is this something to worry about? Are they really good? Are they gonna are they gonna whoop us or whatever? And I go into their product and I see the first thing that says which which LLM do you wanna use, I'm like, not not a problem.

Aaron

Cool. I can log on. Yep. Not my problem. Yeah.

Jordan

Yes. And what we're understanding is that we are in order to do that, what we should focus on is none of the hard parts. We've identified our hard part. It's onboarding nontechnical people into an AI product. And geez, isn't it?

The need. Stop doing the hard part. Don't worry about the LLM. I basically outsource everything. You're an AI rapper.

Embrace it. Give it a big hug. You're an AI rapper. And there is a lot of value to add in the UI layer for non technical people.

Aaron

-Yes.

Jordan

-And and just solve the problem for them. And so in much the same way where I'm like, I don't I'm gonna yes. I understand the risk of us leaning on people for the transcriber and for the synthesizer and for the LOM, and I don't care at all. We're just gonna lean into that risk and get the advantage for it.

Aaron

So tell me this. Does Rock have any problems with that? Because I feel, as a developer, I'm like, there's some misplaced purity inside of me where I'm like, no. I need to teach 120 videos about Postgres because this is what the material demands if you want to be a proper user of this database. Right.

And what the market is probably saying is, I want one hour of a crash course so I could get back to my life, and I'm trying to square that circle.

Jordan

Again, if you let the key ideology guide you, the way Rock with two kids now, since we met, since he's children, he got married.

Aaron

Mhmm.

Jordan

And he has adopted my ideology, which is after tax money in our personal bank accounts.

Aaron

Yep.

Jordan

And the way to do that is make the company successful, and the way to do that is what the strategy dictates. Don't build. Don't build stuff. Make it

Aaron

very stuff.

Jordan

Right. Make it very reliable and good. So our we have a recurring experience, and this is a bit tricky. You get people coming into our product and then saying, I've tried all the others. Yours is so much better.

Thank you. Feels amazing. Now, look, in reality, what we know is that when people go in that direction, you hear about it. When people go the other way and they leave you and they go to someone that they think is better, you don't hear about it. Fine.

I don't care. I'll take the the the positive feedback. And so we are adding things to make it better.

Aaron

Mhmm.

Jordan

It's just that it's less of an engineer hard engineering challenge, and it's more of, like, a clever engineering challenge. How do we add our own prompts and our own rag system? And how do we make it more likely that the agent doesn't hallucinate? And how do we make it so that when she says, is there anything else I can help you with? That she doesn't say that four times in a conversation.

That we have we have different versions to make it more human like. So it's not like there aren't challenges. It's that you do have to relinquish the hard engineering challenge that you might think of yourself as trying to encounter.

Aaron

Mhmm.

Jordan

So you have, like, this bar that you wanna meet around the content you create.

Aaron

Yes.

Jordan

I think part of why people are attracted to your content is because that bar is so high, and people are attracted

Aaron

to I don't wanna I don't wanna lose that. Yeah.

Jordan

I don't think you need to. But maybe you can be one touch more realistic. I'm gonna avoid using the word cynical with you because they they're like magnets. We don't like that. Yeah.

But maybe you can look at it and say, I'm gonna meet my bar.

Aaron

Mhmm. And then

Jordan

I'm gonna strip away lessons one, two, and three, or we're gonna package that up for $19.

Aaron

Mhmm.

Jordan

Because that actually gets people the value that a lot of people need, and beyond that, they don't need. Right. And and we we can use that to subsidize our spend toward customer acquisition. And, no, we're not gonna make any money off that, but it puts them into our ladder. And because our bar is so high, more than usual convert to that higher tier, and so it's worth it.

So what I would do if I were you is I would do what the Excel guys are doing.

Aaron

Tell

Jordan

me. People selling Excel courses are making millions of dollars because they're taking they're taking this little nugget that people need

Aaron

and

Jordan

they're putting it on TikTok and on Instagram and on Facebook deals.

Aaron

You think that's the move? Yeah.

Jordan

Yeah. Not not excel, but take the little nugget from the bottom of the pyramid. Right? The Excel course that the guy is selling is so sophisticated, I will never need it.

Aaron

Sure.

Jordan

But a lot of people need the most basic version, the one step up from I'm an Excel noob

Aaron

Right.

Jordan

To now I'm proficient at something. And and maybe that's what you're selling as an introductory for the bottom of the pyramid. And if you have to spend money, let's say you have to spend $5,000 a month on an agency that takes all of your content, clips it up into shorts and post it. I mean, there's a lot of tools that do this stuff, including

Aaron

Right. Yeah.

Jordan

That you really don't even need an agency. So you can keep the bar really high and use that as your secret weapon. And your secret weapon is actually my bar is so high that more than you would expect convert to that higher tier because of how good the the the quality actually is. You don't have to lower the quality. You might just need to change your assets and put them into a form

Aaron

Package them differently.

Jordan

Yeah. Package them differently and position them differently for more people to consume.

Aaron

This okay. So here's what this is making me think. K. This this is making me think that I would be so what I'm hearing from you and you and Rock is your focus is on building the business. And I think that isn't, like is worth saying because most engineers, their focus is on writing the code, doing cool stuff in the code.

Jordan

Building the product, making it amazing, reducing the number of bugs, nailing the development process.

Aaron

Making the queries faster. Like, we love that crap.

Jordan

Yes.

Aaron

Perhaps perhaps my focus has been on has been on producing content, which I think is good, right, and noble, but my focus needs to shift on that spectrum a little bit to building the business and not lowering the bar for the content, like you said, but changing how we present it, perhaps.

Jordan

Yeah. Yeah. It it's it sounds more like a packaging challenge than than anything else.

Aaron

Mhmm.

Jordan

And you're you're already when you left the job or were were asked to leave the job Mhmm. My assumption was that the journey that you're on right now, that you will go on and that it will end up in the right spot. And I think that's where it's going.

Aaron

That's good. You know? The the That's good. Yeah.

Jordan

The right spot is how do I add value, and then how do I expose a ridiculous number of people to that value.

Aaron

Mhmm. Mhmm.

Jordan

And if anything, that I would challenge you on is to get exposed to other people. Right. Because right now, if you go on Twitter and you sell your thing, those are people that have been exposed to you and your quality of work, and that's why they buy. Mhmm. But if you want to be introduced to other people that are not in your audience that don't understand what it takes to do what you're doing and don't because of that don't have an appreciation for it, let them come in a different way.

Mhmm.

Aaron

Yeah. Yeah. That's good because the audience that I have now has taken me ten years to build, and we gotta we gotta get new people in, and we don't have ten years to do it.

Jordan

It's almost like a top down process. They're coming in and being exposed to your best, to your tweets, to your thinking, to your podcast, to your like, the process of making the course. Right. And then when

Aaron

it's available to buy, they're, like, reaching down to give you a hundred or 203 hundred bucks.

Jordan

Hundred or 2 hundred, 3 hundred bucks.

Aaron

Mhmm. Yeah. I know. You're not wrong.

Jordan

Right. So they, like, love you to such a high extent, and then they're buying what what's made available to them. I'm sure a bunch would buy at the $25,000 level for you to help their company, but that's not the way your business is going. I don't think you wanna do that. Mhmm.

Aaron

So

Jordan

if you want it to go the other way, then you do need to figure out a mechanism for exposing people that don't know you or your content at all, but come from bottom up, from your $10, 20 dollar, 30 dollar offer, and then get exposed to, holy cow, this this studio is as good as I thought it was gonna be, as good as the original bread crumbs that I picked up on Right. On Instagram that showed this kind of basic thing but done in a very good way. When I get exposed to the rest of the content, I'm just gonna eat it all up. I'm just gonna buy the bundle because, you know, I'm impressed.

Aaron

See, I do I I it's hard for me to, like it's hard for me to internalize that, but I do think we have a competitive advantage in that our content is very, very good. I truly believe that as much as it's hard for me to say, like, our stuff is the best. No.

Jordan

I think that.

Aaron

I actually think our stuff is very good. Yeah.

Jordan

You know what I'm curious about? Remember Egghead? Wasn't that what is it?

Aaron

Oh, yeah.

Jordan

Right. That was a big, like, developer education platform?

Aaron

Yeah.

Jordan

How did they get so much traffic? I feel like I feel like they were a bit of a machine around

Aaron

Yeah. Did did they Yeah. I think I think back in their heyday, they had they had very high, you know, editorial quality standards as well pushed by, Joel Sure. Who is great has great taste. And I think they benefited a lot from the studio model, which brought in all these disparate audiences from all the instructors.

Jordan

Right. The instructor, I guess. Would basically sell their egghead course, and they had, like, this web. Yeah. That's that's pretty neat.

Aaron

Exactly. Yep. Yeah. Yeah. So that that is a play for us.

I don't think any of the instructors we have for screencasting have big, you know, stand alone audiences, but that is that is a play for us as well that we could, you know, we could move towards. And the model the model there would be AlaraCasts, which is like, they've got a bunch of guest instructors, and, you know, that is the destination. And I think screencasting could be the destination for video training, that kind of stuff. So Yeah. What do

Jordan

you got going on the rest of the week, my man?

Aaron

Alright. Have we done two hours? This this turning Yeah. We've we've done two hours. Hey.

This is great. Yeah. Here. I gotta I gotta we can we can end on this one. I got one for you.

Yes. You moved to a new city. Where where did you move from? From Portland to somewhere?

Jordan

From Portland to the Chicago Suburbs. There you go.

Aaron

You're an adult. So I'm at dinner. I'm at dinner last night

Jordan

Okay.

Aaron

With, the older set of twins. So two two, three and a half year olds. Just me. Sometimes, you know, we split them up to make everybody more sane. So I take the older ones out to dinner.

And this guy and his wife walk in, and he waves to me. And I wave back. I'm like, hey, man. Local local restaurant. So I'm like, I feel like I know this guy.

After he sits down, I remember that guy's got twins, and I've seen him at this restaurant before.

Jordan

Okay.

Aaron

That's how I know this guy.

Jordan

Perfect.

Aaron

And so I'm like, oh, okay. Good. I've placed him. Like, he didn't have his kids with him, so it kinda threw me off. But I'm like, I remember talking to this guy.

And, you know, thirty minutes later, this guy walks over to me, and he's like, hey, man. You're twin dad. Right? These are your twins. I'm like, yeah.

You were here, you know, a couple months ago. We talked. Right? He's like, yeah. I just wanna come over and see how you're doing.

You know, we talk, exchange pleasantries for a little while. And then he does the bravest thing I think any adult man can do. And he says, hey. We're trying to make friends in the area. Can I get, like, can I get your phone number?

And I said, absolutely. Like, his twin you know, his twins are the same age as our younger twins. And but I just put myself in his position of, like, I'm a grown ass man walking over to this stranger that I met one time four months ago and putting myself out there to say, hey. We're trying to make friends in the area. Can I get your phone number?

Mhmm. And I was like, I can't imagine. I I consider myself a very brave person, but that was, like, next level. Making friends as an adult in a new place. Mhmm.

What what how does how do you do that? Because I watched that, and I was like, good for you, man. Yes. You can have my phone number.

Jordan

Yep. That's impressive and admirable. And I sympathize. It's

Aaron

gotta be tough.

Jordan

Very much. Absolutely. My wife is good at it. Mhmm. She has made a bunch of friends.

One of the reasons we moved here is because we had some friends in the area. Mhmm. We both went to school at Michigan, and a lot of people that go to Michigan are from the Chicago area and come back here afterward. And one of them was my wife's very close friend, her roommate in college, actually. And by insane coincidence, our house is 1116, and their house is 1115.

It is directly across the street right there.

Aaron

No way. Right

Jordan

there. If you walk out my front door and walk along the path of the, street and then just go across the street and continue on the path, it goes to their front door. This

Aaron

Your wife's college roommate lives across the street from you. This is You you you have no answers. You got it easy. You got it easy.

Jordan

Relatively speaking, we have it easy. So, yeah, absurd absurd bit of luck. Like like, she vouched for me when I got set up on a blind date with my wife when we first met. Amazing. You know, amazing coincidences.

Now because of that, she's had an entry point.

Aaron

Mhmm.

Jordan

And I have been left off to the side. And I'm gonna guess that a lot of husbands, dads, single guys listening have this experience. We're just not as good at

Aaron

it

Jordan

as as the ladies are in terms of getting together in book club and going to dinner and all that. Right? So I will go weeks without seeing a friend. And I if I stop to think about it, I care. But in the day to day, I don't feel that this need for it.

Only in hindsight where I'm like, I should expand my life.

Aaron

Mhmm. So I've been thinking about onboarding a lot. I gotta get some friends.

Jordan

What am I doing here? So I I do use modern technology to overcome a lot of that.

Aaron

Tell me.

Jordan

I talk to my brothers all day, every day k. On WhatsApp with with my dad. We're very close. My dad actually just moved here.

Aaron

From the

Jordan

malls are amazing. Right? So now all of a sudden, he's, like, in our day to day lives. It's great. Between my brothers, my dad, my mom, and people online, and my my colleagues,

Aaron

Sure.

Jordan

The Rock is I mean,

Aaron

it's quick. I talk to Steve in both of my times a day. Yes.

Jordan

Yes. Jessica. Like, I know these people. I care about them. I know their kids.

So that does fulfill a lot of this. But there are times when I mean, men need companionship Mhmm. In that way, and I am no exception to it. My problem is I am incapable of being inauthentic for long periods of time. Mhmm.

I just don't have that much in common with a with a lot of men my age.

Aaron

Mhmm.

Jordan

I don't care about sports. I just God. I just don't care.

Aaron

You should move to Dallas. We could hang up. Oh my god. I just don't care. I just don't care.

Jordan

Chicago sports town. Dallas sports town.

Aaron

Sports town.

Jordan

So when a few guys get together and they start talking sports, then they start talking about, like, our kids' sports teams. I'm like, guys, what are we talking about here?

Aaron

Worse is, like, who we're gonna draft next year. Yeah. It's not even, like, what's going on in a league or or even my kids' league, I could probably care about. But, like Yes. Woah, man.

How's the draft lineup looking? And you're like, brother, I have no idea what you're saying. No idea. No idea.

Jordan

Okay. So that we are in a category, like, that's a challenge. Yes. And and it's as much as I admire your new potential friend.

Aaron

Mhmm.

Jordan

If you get together and have lunch, which you should Mhmm. If he's all up in the sports and and works at w two, it's gonna be tough, man.

Aaron

It's gonna be tough. It's tough.

Jordan

Yeah. So I I just sympathize for myself, for you, for a lot of other people listening. If you work from home, you don't have an office, you can find yourself pretty lonely.

Aaron

Mhmm.

Jordan

Even if you don't actually feel lonely, but you have created a kind of a lonely life, So you gotta figure out ways to do something about that. Like, I'm going with my friends from college to see the dead in Vegas at the Sphere. K.

Aaron

Cool.

Jordan

I I probably went multiple years without doing anything like that. And and I'm trying to get better at it. I had a particular version of the disease that said, when you make more money, you're gonna do all this fun stuff. Yep. And I just pushed it off and pushed it off.

No. I'm focused on work. And when I when I make a bunch of money, then I'll do all of that. And then a few years go by, and you're like, this is just what a career is. Like, stop, you know, pushing things off into the future.

Aaron

The the road the road expands before me. What is happening?

Jordan

Yes. Yes. And and then you do the thing where you look back five years, and if you had told yourself that you'd be here now, you'd be like, oh, so now you must be hanging out with all your friends and go to the dead shows and all that stuff. Okay. And then what I do is I'm just a bloodhound for entrepreneurs.

I just I spot them and I find them in in the local area. As soon as I find one, I just gravitate toward are you thinking about the same things I'm thinking about?

Aaron

Mhmm. Like,

Jordan

do you not care about this football game at all? And And you really

Aaron

have to go talk b to b sass over in the corner?

Jordan

Yes. So I found someone here who runs an AI consumer company that Amazing. Builds, like like, books for kids and makes the kid, like, the star of of the book.

Aaron

Love it. Love it. Love it.

Jordan

Let's go let's go get coffee,

Aaron

my man. So where did you find this person?

Jordan

At a party k. That my wife got invited to with and and I just go along and, you know, I'm like, yep. Like, I'm a husband. Mhmm. Let's see if I have anything to say.

Sometimes I do, sometimes I don't.

Aaron

And

Jordan

then as soon as we kind of identified, we're like, oh, you live in this town, which is not an entrepreneurial town, then we should hang up.

Aaron

Mhmm.

Jordan

It's really, really tough. Leaving Portland was hard because when I first got to Portland, I went to a MicroConf meetup. Uh-huh. And then we went to MicroConf, like, a month later, and we realized, oh, there are, like, 25 of us.

Aaron

Lot of port Lot

Jordan

of port MicroConf first. And then we started maybe I have the time to mix up. Then we started going to lunches. And then from that group of, like, 15 people, you know, you shrink it down, and those, like, five or six people, I still talk to in Slack all the time.

Aaron

Mhmm.

Jordan

And some of our families got close, and so Ruben Gammes is there, and Johnny Ewalt is there, and Jared, and, like, you know, so we have this thing. And that turned into real friendship. And I it's been three years here in Chicago. I I don't have it yet. So I I I got work to do.

Aaron

Well, you know, walk up to guys in restaurants and ask for their numbers. I can't see that going wrong at all, but it worked. It worked for Aziz. Aziz got my number, and we're gonna hang out at some point. So I just thought that was, like, incredibly brave.

And I just I I knew that you had moved. How do people do this?

Jordan

Where do you put yourself on the scale of, like, one to 10 on, like, no. I have, like, a friendship life. Not like a social or, you know, you're married all that.

Aaron

I think I'm I'm I'm pretty high up there, but that's because, you know, I in Texas, I live in Dallas, went to Texas a and m, which is three hours away, then a lot of people came back to Dallas. Cool. And so and then we're also very involved in church life. And so we've made a lot of friends through, like both of those things are through, like, structured organizations. You know?

And that's the thing that scares me is, like, once you're out there on your own, you don't go to church, you're not in your college town or a town adjacent to your college. Then what?

Jordan

Well, the I don't know. The office was was that other structure.

Aaron

And there's no office. Yeah. Yeah. Yes. Yeah.

So Yeah. No. I I feel I feel good.

Jordan

We don't belong to a temple because I'm I'm not religious at all. So and I've considered joining a temple more and more partly for that exposure of, oh, other people with

Aaron

structured serendipity. Something you

Jordan

can come in as an empty starting point.

Aaron

Yes. Yes. Exactly. Here's my question

Jordan

to you.

Aaron

Tell me.

Jordan

Do you know that there's a weekend coming up and that you should make plans for it? I I do not know. I'm just like, oh, it's Friday. And unless someone invited me to, like, what are you doing this weekend? I never think, hey, it's the weekend.

I should do something social other than, you know, do whatever driving is required.

Aaron

Absolutely not. Yeah. Okay. That's Absolutely not. I'm I'm I'm I'm I'm I'm I'm I'm I'm I'm I'm I'm

Jordan

get over that problem. Problem.

Aaron

That's No. No. No. No. No.

Never ever ever never ever ever have I thought, oh, shoot. It's Thursday. I wonder I gotta get some stuff to move in for Saturday.

Jordan

At some point in our lives, we were like, what do you

Aaron

do with the weekend? And it was the fear life. It was but it was a fear of, like, oh, shoot. I don't have any weekend plans. Yeah.

What's everybody doing? And you start texting like, hey. Are you doing anything? Yeah. We don't know what you're doing.

No. We gotta do something. Yeah. No. So I have benefited a lot from, like, recurring, like, scheduled hangings.

Jordan

Okay.

Aaron

And so every month, we do a supper club. It's, like, four couples, and we rotate houses. And so every month, there's at least one time I'm gonna see Gonna see friends. Six other people.

Jordan

And a month goes goes super fast.

Aaron

Super fast. And so we're doing a no kids no kids dinner.

Jordan

Same for couples.

Aaron

Same for Different house every time. Different houses. And if you're

Jordan

You get to to cook for people.

Aaron

Yes. And if you're not cooking, you're not expected to bring a goddamn thing. So it's not like every month, it's like, oh, I gotta do a potluck. I gotta bring a salad. I gotta make a pie.

No. Once every four months, you have to do the whole thing, and then you're off. So that's great. Huge. Love that.

Jordan

I like it.

Aaron

I do a guy's breakfast, every three, four weeks. We do that pretty regularly. Once a year, we do a, a guy's college reunion, like, twelve years in a row or thirteen years in a row, whatever now. Just solid. Eight to 10 guys every single time.

Jordan

Good for you. We we fell off. Do you go to the same place every time? Do you go back to college, or do

Aaron

you We go everything. We go to the same area. We go down to the Austin area, but out in the Hill Country, but it's a different Airbnb every time. Always river adjacent. So all we ever do is we get Yetis full of beers, and we go sit in the river and just laugh and throw rocks at sticks and be like, hey.

Do you think you can hit that? And that's all we do for, like, Three days. It's tough. Hell, it's good

Jordan

that is.

Aaron

Oh, it's awesome. Yeah. And then, of course, we have, Sunday morning church is not a place where you'd meet a ton of people because it's like we got four kids in tow regular thing. But it is regular. Yep.

And then we have a Wednesday night bible study, and that's more that's kid free, and so that's more like we Jennifer and I take turns because we're not gonna pay for a babysitter every Wednesday night. But that's still another Interesting. So we have a lot of we we have a lot of scheduled scheduled goods.

Jordan

The the more structure, the better on that front. If it's left up to me, you know,

Aaron

you'll Yes. It it will It goes three years, and you Yes.

Jordan

It will

Aaron

be that you have

Jordan

over here to my right on the floor that will literally stay there for twelve months.

Aaron

Yep. Yep. Yep. Feel that. It's not Yep.

Jordan

Not good. Okay. Alright. I'm motivated. I'm motivated toward my ideology,

Aaron

toward making

Jordan

content, toward making more friends.

Aaron

Aaron, thanks a lot. If if if your ideology combines with your going back to temple, keep the ideology down a little bit. You don't wanna walk into temple and say, I pray to the god of capitalism. No. No.

No. Separately.

Jordan

You know, one one, I'm I'm not religious, at all. I I was raised to not not go to temple, but that side of my life has made itself more of a priority, since October 7 than in the past. Yeah. And and I like it. Good.

I I like it. It's a it's a feeling of more meaning

Aaron

Mhmm.

Jordan

And less isolation. Yeah. So I in in many ways, it's just in my head, because a lot of my actions haven't changed that much.

Aaron

Mhmm.

Jordan

But that doesn't matter.

Aaron

There is, obviously, I think there are very, very good things about religion. But another good thing about it is you're a part of a group of people. You're a part of a group of people, and it there's, like, a sense of belonging, and I think that's very powerful.

Jordan

Yeah. I I I not dismissed. Maybe I avoided or or ignored that because I didn't have it. I moved here as an immigrant. Mhmm.

Not religious. Didn't join a temple. Went to school, and then just kind of you know, Judaism just didn't have much of a role in my life, and I feel isolated as an immigrant. To begin with, all my family's back in Israel. Sure.

And so I I think after the Sabbath, I I was like, oh, I think I actually need, not want. I think I actually need some feeling of belonging. And now it feels more more balanced in that way. It's nice.

Aaron

Yeah. Well, I'm sorry, obviously, about the the circumstances, but I'm glad you feel a little bit of balance there.

Jordan

Thank you very much.

Aaron

Yeah. Alright. Yeah. It's been great. Howdy.

Yeah. Ian, we we did two hours just for you so you can listen to this while you're waiting in line at Disney World or whatever you are.

Jordan

You are you a Disney hater?

Aaron

Come on. I'm a I'm a I'm not a Disney enjoyer. Yeah. I'm a Disney skeptic. Fair.

Yeah. Ian has tried to talk me out of it. It just feels like an expensive way to wait in line, but I could I could be wrong.

Jordan

My my hat is Disneyland in California Okay. Not Disney World. Yes. Yeah. And I was as skeptical as you, and I went with little kids, and it it overcame my skepticism.

Aaron

I am sure that my point of view will change when they hit five, six, seven, eight, and we go. Mhmm. But right now, there's no chance

Jordan

you couldn't get me there.

Aaron

There's no chance. That's

Jordan

when I went also. I think when kids were, like, you know, five, seven, and nine, and even the five year old is a bit young. Aaron.

Aaron

Alright. Where can people find you, Jordan? Oh, yes.

Jordan

Okay. If you are an SMB owner and need an AI voice agent, go to heyrosy.com. If you wanna talk, more directly, I'm on Twitter at jordan gall.

Aaron

Except for next week when he's in Hawaii. But otherwise, he's on Twitter.

Jordan

And keep an eye out for for my threads. And Oh, boy.

Aaron

Oh, boy. For my upcoming podcast. Yes. Oh, I can't wait. Dude, this was to

Jordan

join me for an episode.

Aaron

I would love that. This was a blast. Thanks for giving me two hours of your time. This is so much fun. So thank you all for listening.

You can find everything at mostlytechnical.com. Thank you to the sponsors for making this possible, and we'll see you

Jordan

next week.