Bootstrapped Web

Welcome back, everybody, to another episode of Bootstrap Web. Mister Brian Castle, how are doing?

Doing good today, Jordan. Yeah. Good to be back on the on the mics here. Good to of squeeze one in because I'll probably be out next week. I'm heading out to Founders Summit in Asheville, North Carolina.

Pretty excited.

Please tell more. What what is Founders Summit?

Yeah, it's a conference. It'll be my first time attending it. It's put on by the folks over at Com Fund, Com Company Fund. So yeah, I mean, it's this thing where I guess it's like a 100 or so attendees and this one is gonna be in like the mountain areas, like the Blue Ridge Mountains of Asheville, North Carolina. They sort of rented out a whole campsite.

So there's like all sorts of like activities like hiking and campfires and chefs on a lake and doing all sorts of fun stuff with with other founders. So it should be cool.

First, that sounds fantastic. Second, I imagine the environment there will be really good because Comfund and Tyler, sitting pretty right now. They're looking pretty smart right now. When it's a bull market and VC valuations are nuts and money's everywhere, the com version of business can look quaint. And now it looks smart.

Yeah. I mean, you know, it's like, who knew? Like running a a small profitable business can actually, can actually work out well. I do think that their whole portfolio looks looks real solid right now from what I can tell. Like, I'm not that closely connected to many of these folks.

That's one of the reasons why I'm I'm excited to go. I I would like to just get to know more more people in that community. I I do know some and I'm excited to connect with them, but yeah, think it'll be a good opportunity. It's also, like, probably the perfect date in the calendar to be going on a trip like this. I mean, like, the leaves right now around the mountains and on the East side of the country is just unbelievable.

So pretty excited.

Well, I'm going camping this weekend also, but to a a daddy daughter camp. So I'll bring the three girls, just me and then a a friend of ours and his daughter. And it's just one night in a cabin, which is exactly how I like camping. We're gonna have a good time. And, you know, unfortunately, here in Chicago last weekend was like 65 and sunny.

We were at the beach. It was amazing. And this morning was 40 degrees. So I I'm ready for some cold.

Yeah. We're my family, we're we are all about the glamping thing.

Yes.

Go go on Airbnb, you get a feel like a tent, but it has a bed. You

know? Exactly. Cool. Well, what what else is going on? You wanna start?

Want me

to start? Actually, I think since the last episode, I I just came back from Colorado on our no snow tiny comp trip, which was a good, you know, small retreat with a couple of founder friends. That was, that's always a good time. Coming back from that, I still have a lot of energy, you know, heading into this Q4 on the business. So lots to get done.

And you know, like we're really close. It's this like mastermind group of friends that get together a couple times a year. And I think we all, in a healthy way, like really push each other to make progress. You know, a lot of it is centered around like between now and the next time we get together, and we're gonna be getting together in January and February. So I really frame my work around like, what am I shipping?

What milestones am I gonna be achieving that I can report back on when I see these guys again in February?

Do you still have the same strategy? What have you changed? And so this one, how'd you feel when you got back? Because I know you all are pretty straightforward with one another. That's the beauty of getting close to people that you can be very honest, transparent.

How was the general vibe there?

Well, the trip was great. Dave wrote him by really organizes a fantastic trip. In terms of, like, everyone else, it's always kinda fun to to see, especially folks who are sort of in transition. A few of us have been in transition, between businesses over the last year or two, so that's that's kinda fun to to keep track of. In terms of my stuff, actually coming out of this same trip last year, September 2021, it was actually the, coming out of that trip, made the decision to go freemium with, with Zip Message.

Okay.

And we're still freemium today. No like major strategy changes came out of it this this time around for me. It was more about, like, going in, I I already knew what our direction is for the rest of the year. And and again, a lot of that is, like, focusing in on coaches as our primary customer, you know, all the research that I've been doing. I did some like digging back into the history of ZipMessage and I found like more instances of of how I was thinking and talking to coaches early on in the business, but it wasn't until more recently that we're really actually focusing the product on them.

And that's that's where we're headed. And I think the big takeaway is, you know, you know what one challenge that I've had, I guess I still have it, is that I start to feel uncomfortable when I'm not working on marketing.

Okay. If you're too focused, too insular?

Yeah. I mean, my strength and where I feel like I like my job really should be is the product side. So designing and building features and talking to customers and making sure that we're building the right things and and all that. Like, that's where I really love spending all my hours and and I feel like I add the most value to the business. Marketing work in general is not my strong suit, but I do have that I've had this mentality for a long time where it's like, if I go for too long only working on product, I I get uncomfortable.

Like, why are we not doing anything on marketing? Right? So that pendulum over, I'd say, the 2022 swung much further on the marketing side. I hired a bunch of marketing people. I I spent a lot of my hours working on marketing strategies, new marketing systems and processes, putting people in place, putting engines in place that can run.

So I spent a lot of my energy on that side and and naturally, we sort of slowed down on shipping new features on the product side. But and and I also did a lot of research with coaches, a lot of interviews, all that. I've I've talked about that. So now heading into q four, like, what the business actually needs is a big push on the product side. Like, we we need to to move the the goalpost in terms of what our roadmap is and we need to ship.

And, like, shipping a lot of these new features will will bring us to a whole new position in the market in terms of the capabilities, in terms of who we're serving, in terms of pricing. It's going to, like, unlock a whole new shift in I actually believe that this is going to unlock a big growth swing for for Zip Message,

But the only way to get

there is to ship these features. And and it's actually a lot of stuff to build. So what the business actually needs is me working on product for, like, an extended period of time. Yeah. And that's an uncomfortable thing.

I mean, we have marketing people in place, we've got processes that we're doing, but I need to focus on product. So that's where I'm at.

That set of difficult decisions feels very common when I speak to other founders. It feels like everyone is dealing with a difficult set of decisions to make. That nothing's easy, nothing just works because it's been working. Things just aren't going up into the right because they have been. It's all like a whole landscape of trade offs and discomfort.

There's no sitting pretty, there's no everything's going up, there's no my house is worth so much more, my business is worth so much more. You know, it's there's no feeling of inevitability towards success. It's feels like a hard time.

I've always felt that, like, whatever happens in the larger economy, even the startup economy always feels, like, distant and it doesn't really impact my business and my customers. Do

you still feel like that?

I don't I don't know. Like, it's I always have a hard time because, like, you know, like, in the last last couple of weeks when when the market takes a turn, like, all of a sudden, I did see a bunch of churns. And I did see reasons like, oh, I'm cutting costs. Like, oh, interesting. I haven't seen that reason come up as much in previous churns, you know.

So, you know, you never really know. But then but then we also had a week where we we signed up, like, four or five new new customers in a day or two. So it was like, it does go in and out. But at the end of the day, I tend to sort of ignore the market and just focus on my customers and what I'm hearing and and how our product is performing. And that's that's where I'm focused every day.

That's probably healthier, right? It's dangerous to use macro as an excuse because it won't work the other way. When things are going really well, it's definitely you and your product and how great you are communicating it and so on. But when it's bad to then say it's macro and the economy and so on feels like a dangerous place to get to in terms of excuses, it's definitely true that when reliant on venture funding, macro all of a sudden plays a larger role and it's much less of an excuse and much more of a reality that you kind of have to deal with because one set of your customers, maybe that's not a perfect analogy, but it's a type of customer.

Yeah. Yeah, sure. When like the financing is a key metric that impacts your business, right? Then it's like, what's the state of things there?

That's right. It matters a lot what's happening in the market with their LPs and their ratios and and how tight the market is and the metrics that are now required that are much higher. And in truth, they are customers, they just happen to be buying your equity and not your product. Well, don't I talk a little bit about what's happening on our side and then I really want to get to your coaching community part of it.

Yeah, we launched that. I'll get into that in minute. So yeah, what do you got?

So generally I'm feeling a bit like war weary. I'm tired. I think it goes along with just nothing really being easy right now. The fundraising process was exhausting. It feels amazing to be able to focus on the company now.

But in doing so, like there's a lot of friction in the market to getting people onto demos for them to buy, to onboard. People are cautious. It just feels generally difficult. There are some weird things in our market that a certain set of expectations were established by companies that were very well funded in the most frothiest time, right? So Bolt and Fast were these classic cases of raising enormous amounts of money and there's some residue there to deal with.

So for example, fast, the way they arrange their payment processing was that everyone used their Stripe account. It was like a custom connect type of a thing. Then you went out and you connected. Even if you had a Stripe account, you still needed to go off and create an account with them.

That seems so dangerous to structure your business that way.

There were some pros and cons to it. One of the pros that they had going was that because they did that, they linked up with a fraud partner and then could tell the merchants not they don't have to worry about fraud. Don't worry, there's zero cases of fraud that you'll have to pay for because it's on us. And that was definitely a money loser, but it became established as an expectation. And now when people look at our product, they're like, okay, so it's with fraud, right?

And it's not. So look at something like that and we say, oh, now we got to go. Yeah. We're doing their payments.

Yeah. So so, like, I'm just trying to think about, like, the value prop of of Rally. Right? Like, what's the main problem that it solves? Like, my understanding of it was, like, it's it's for headless e commerce.

It's it's a streamlined checkout. Yep. Better conversion. You can you can yeah. Increase conversion.

Yep.

Increase conversion.

Upsells and all that. Customize the the structure of your site and the and and how it's built and and the different tools you're using that like, the whole headless ethos. Right? But the fraud thing seems like a different, benefit, a different product solution sort of thing.

That's that's right. It's one of these things where we just didn't expect to need that as part of the pitch and part but but that's what the market wants. So there there's just things like that where it's like you bumping into something and saying, oh, I got over this hill. I thought I was done. Turns out there's another hill behind it.

It almost so correct me if I'm wrong just to simplify it. So like this market that that Rally is headed into, it's sort of like a cutting edge version of of e commerce. Like, the the the play is like your the whole, like, headless ecosystem will flourish over time and Rally should be should be one of the early big players in it. But this sort of new category was first defined by Bolt and Fast.

Yeah. Yeah. In in some ways, that's right.

You know, like, yeah, you wanna push this category forward, but you're also sort of like dealing with some of the fallout from what happened with Bolton Fast.

Yes. And and right now, when people think of headless, they think of complicated, expensive. And so we don't want to go there yet. Right now we're really, we're a checkout for existing merchants to upgrade from their old checkout. So it's actually doesn't really have anything to do with headless, even if it works in a headless way.

So what that has really led to is just an enormous amount of effort on all fronts. And I read this tweet by Naval that really stuck in my head. The tweet goes, big companies and repeat entrepreneurs struggle to go from zero to one because they refuse to restart at zero. And that one bothered me.

I really think that any multi time entrepreneur resonates with that, to be honest.

Right. You are smarter on certain things. You're not the same person that just whatever definition of restarting at zero is for you. You don't actually wanna

Isn't it such a weird paradox how years in business across multiple businesses does help. Building up that experience, it's almost like building up your gut and building up, like, just, like, core strength.

Competence. Competence. Yep.

Speed and all that stuff. But it still doesn't make it easier to launch a business. Like, every business is going to be challenging and like, no matter what and it doesn't matter how many you've built before. Yes. I I absolutely see that with Zip Message, you know?

Look, it's it's fun to go back to zero. I often think about what that was, and that was just zero excuses, just doing whatever needed to happen next. I just did it. It's not actually that fun to do that. No.

So so this

means It's it's so weird, right? Like there like I definitely miss the feeling of, like, the comfort level that I was in, let's say, three years ago in in, like, the I'd say, like, the the middle section of me owning Audience Ops. Because it was just a nicely profitable business with cash flow, good team, good system, good customers, like, weren't weren't the the biggest agency on the Internet or anything like that, but it afforded a nice lifestyle for me. And now it's like back to startup grind mode and and for for an extended period of time, years.

In a much worse economy where everything's harder and competition is through the roof and it's like, oh shit, I gotta refine my fire.

Yeah, that fire, right?

Yeah. At Cardhook, it was two years of grind, another two years of fighting. And then we got to a place where I was sitting at the top of an organization that could handle itself without me. And it was making more money than ever. And I was real comfortable.

In that area, I was at my happiest because I could go take an hour long walk and come up with a few ideas on connecting an agency with this other person and doing a case study and then publishing it. And that would have a great impact on growth. And that would be like the best way for me to add value to the company. And it sounds great to operate Rally in that way, but it is not going to work. This week felt like that came home in a very specific way where we had to let go two people on the same day in the go to market team that's just kind of forming.

And what that meant was the next day I did the demo.

And what are you able to share here? Like, so what happened around those two people?

Sure. I can

And don't go into anything.

Yes, yes. So you keep everything in terms of privacy, obviously. And probably the right caveat to start off is if I'm firing two people, like maybe two months after they start, probably my fault, at least to some degree. It was a mismatch of sales

approach and our You know what? Just on the timeframe piece, like all the people that I ended up letting go over the years, it usually happens within that two to three month timeframe. Right? I feel like that is when a firing is probably supposed to happen.

Right, you shouldn't do it two weeks in. That's kind of like, hey, you're being rash. Let's

You're not giving them a chance. Yes. But at like six to twelve months in, it's like something bad must have really happened.

Right, and you waited too long. And if there's anything in the experience of previous companies that you learn is there's a tendency to wait too long and you always regret it. And so I don't have that issue anymore. So there was a mismatch. I'm going to try to talk about this while maintaining privacy, but in a way that is actually valuable to talk about.

The single most important element, right? If there's another founder listening to this, it's record your demos, Record your demos. Because the assumption of I interviewed this person, they are good at sales, they did the mock interview with me, they did it well, the whole deal, the confidence is there. You kind of have to make sure. And I don't like making sure.

And if I'm being entirely honest, I would have ignored it for longer unless someone else on the team was like, you, we got a problem with the demos. And that's, I mean, that's when I saw a recording and I said, Oh, we got a problem. And I saw other recordings and I saw other So it was kind of like, okay, there's a mismatch in how we need to sell our product with how this person does a good job at sales, but for a different type of a product. Ours has to be more consultative. It's not like challenger sale.

Ours needs to be relationship trust and love to some degree because it's around payments and checkout. And you have to go slow. You can't pressure into moving forward too quickly. And a lot of that was also around my mistake on compensation structure and incentive structure. If the company needs customers that are all in on the solution and all in on the effort it takes to get it live, that does not match well with the incentive and compensation for a salesperson being based on the number of deals you're closing this month.

Yep. They can be opposed to one another in some ways.

Yeah. Yeah. I I definitely ran into that some of that with audience apps when I had a salesperson take over from from me and but actually just going back to, the way that this bubbled up in your case, like some somebody else on the team brought it up, which is which is, I think that's such a really good sign that somebody is willing to do that on your team because

It's a tough position.

And I think it also speaks to like, you know, there are problems like that, that arise, but then they have to become real bad for someone else to get to a point like, oh, I think I need to bring this to Jordan. Mhmm. You know? Like like, it's gotta be bad enough. Like Right.

It has to rise to the level of, oh, it's an awkward position for someone to be in. And I say it out loud regularly. I tell people, It is a bad reality that I'm the last person to know about bad things, but that is the nature of organizations. And please help me not be the fool and be so late to the party that it hurts everyone. It's not good.

You have to be able to come to me with the bad stuff or it ends up in a position where I'm disconnected and I'm the last to know and it's bad everyone.

Like it definitely took a long time in audience ops, you know, for like my relationship with the manager of the team to get to a point where she was real comfortable with like actually bringing like these kind of thorny team issues to me without You know, because it's also a thing where, like, sometimes when there's something frustrating happening with the team, like, a lot of team members, you know, they feel like it's a reflection on them. It's like, oh, like, I'm not able to work with this person or I'm not able to to deal with like, it's It's

just playing fire. Yeah. Yeah. It's rolling a stick of dynamite into the boss's office and hoping that, you know, it comes out okay. It's it's but it but it has to happen.

Anyway, it was necessary. And then the next step that was obvious was, okay, let's not just point fingers. There was a mismatch in the type of sale and the person and whatever else with our specific company. A, I have no doubt that they'll be successful elsewhere, but B, it didn't need to happen. It was right for us.

And then it also has to go along with, well, let's not pretend that it's all their fault. Let's admit it's also the company's fault, my fault, the training, the education, all this other stuff, including the hiring process. And so let's get to work. And that is like what my week has been defined like, oh, a whole bunch of work that I didn't really have planned, but is now absolutely necessary. And so, all right, that's how it is right now.

Roll up the sleeves. The next day I took the demo, did a thirty minute demo with the other people on the go to market team watching me and smashed it and basically showed the company, all right, here's how it's done. This is how we do demos. Let's start to document what happens before the research, the preparation, what happens during and what happens after. And we're all going to get there.

We're all going to get trained up and I'll do it along with the other person that knows how to do demos right now for six months. I don't care what it takes until we get everyone trained up. It doesn't matter. There's no excuses. We have enough people to do what we need to do.

Everyone get trained up. Let's document it, support each other.

Go. I think it's a a really good move to just It's back

to zero.

To just get back in there. Like, there's gonna be so much to be learned. Just from, like, seeing what the patterns are, seeing what the what questions come up. Yeah. I like it.

And like you said, like, you in there creates all this internal material that your team members and future team members can leverage when they're learning how to do this role well.

In the past, over the last year, I have thought many times, I shouldn't do that. I shouldn't just say, hey, watch me. I should let people get trained up and let them build up their competencies. But now I think this general market sentiment, shit's hard and there's no room for any bullshit. And if me doing the demos for the next six months gives us the best chance to grow the way we need to, then that's just what we'll do.

There's no niceties. There's no stepping on toes. The only thing that matters is doing well enough to survive and raise more money and keep going. That's it. There's no room for anything else.

I just lean towards anything that gets the founder closer to talking to customers, especially in the earlier days. To me, regardless of the way the company's built, the funding situation, like, the closer the founder can be to talking and hearing from customers, the more wisdom comes into the strategic direction. Like, yes, you ultimately wanna have other people in those seats to to do the the job, but the from the research element and and actually experiencing it firsthand, like again, like getting back to, like, when I'm when I'm too much in the code and in design and in Figma and all this, it physically gets me away from talking to customers. And that's when I start to feel uncomfortable, you know, because I'm like, it's been two weeks since I had a call with a customer. Good for you.

It's a good instinct. It's weird. I was saying this to my wife. I think I've said it on the podcast too. Like the emotional roller coaster and the irrational roller coaster.

Right? Like, okay, last week or two weeks ago, we went like, I think almost seven days without getting a new customer signed up. And at this point, that's a long that's a pretty long period of time. And by by day four of that stretch, I'm like, it's all over. This fair.

This this is it. Like like whatever whatever run that got us here is over. Like They just found me out. They figure it out. Like the whole thing is just not working.

And then like on day eight, we get like four new customers and then like two more. And it's like, oh, it's like irrational, but it's there. It's like, know, what's happening, you know?

Yeah, I'm a bit tired from that roller coaster. And this last week I had some very big swings that on the personal side, I had some reason to cry and some reason to celebrate. And I feel like keeping an even head over the next year is going to be a challenge and not be thrown around by the emotions of it. It's a challenge. Takes strength and friends and having fun on the weekends.

And whiskey.

And some whiskey. All right, Brian, talk to us about what you launched.

All right, so like still on the marketing side, but this is now something that that Claire, our our marketing coordinator, is is running with. I'm not really involved in the day to day, although I was involved in the initial creation and launch of this thing that we're calling Coach Club. It's it's actually on its own domain, coachclub.co. And the basic concept is that it's a small community for coaches, but it has a twist in that it's all centered around small mastermind groups. So so if you are a professional coach in any capacity, even if you just do coaching part time or if you're a full time coach, you can apply for Coach Club and we will match you up with only four other coaches into your own private mastermind group.

And we actually run it using Zip Message. So so your mastermind group mostly happens asynchronously where you're where you and your your other coaches are just posting into your into your group. And you get access to the larger community where all members from all groups can connect. So it has that element of like a more traditional online community, but it's all centered around like every member of Coach Club gets into their own mastermind group. That's like first and foremost.

Right? And I think it's really good. So I guess going back to September, we did it privately in prelaunch, like before it ever went public. You know, we have a bunch of coaches in our in our list and in our database. So we invited about 20 coaches privately to be like the first members to to form about four or five of these early groups.

And so they all signed up in in September, created the first groups. And then here in October, we're we're sort of going public with it and we're promoting it to to get more sign ups. And then every month or two, we'll do like a new round of like matching people up into into mastermind groups. So we like created it, launched it. Now, Claire is basically taking the lead on taking in applications, matching people up.

She also does things around, like, you know, engaging with every group, doing, like, the internal member led workshops and things. And so it's so this is basically the start. So Coach Club, in general, like, that name and that brand is is basically the start of what I'm thinking about as like our brand or like a a sub brand strategy. Right? So if I think about our marketing strategy for for Zip Message as a product, it's it's kinda has two sides.

Like, one side happens on zipmessage.com and that's mostly focused on the product and some direct SEO. So we are developing, like, content and articles that we're publishing on ZipMessage. Everyone strategically produced to rank and and bring some traffic. And we have product pages and product value. All that happens on zipmessage.com.

But we want to actually create value for who we know is our best customer, and that's coaches. So launching a thing called Coach Club, and to go along with that, now we have a weekly newsletter called Coach Club Digest, which is it's a which is like a related property, if you will, but it's part of Coach Club. Basically, like that, that's like a curated email newsletter that Claire is writing every week with like, you know, resources, guides, links, strategies, things like that. And and, like, highlighting coaches in the newsletter, stuff like that. But the whole idea here is, like, I just really enjoy marketing projects where it's how do I explain it?

Like Not traditional?

Well, approaching marketing like a product in itself.

Okay.

Like coachclub.co could be a standalone product.

Yeah. Okay. I found it. So coachclub.co and I see it's almost like a sales page. It's like a landing page that describes like the benefits of this product effectively.

Yeah. Yeah. And like it has an actual operation. It has a team supporting it and administering it. And the whole idea is like, if we wanna create something awesome for coaches that we genuinely think they will find benefit from, from connecting with other coaches.

And we've already had quite a few applications, you know, other coaches are really interested in it. So it's just something that's like valuable to them and and it it it it checks so many different boxes at the same time. Right? Like, it's just a valuable thing that coaches can can sign up for. It gets into our orbit, but it also exposes them to ZipMessage.

They're seeing ZipMessage when they're when they're using and and they're involved in Coach Club.

Gathering and you're learning from the market. Yes.

Yeah. These are our go to people that we can present new features to. We can present our we can help spread our own content to to them. And so it's it's just a I think a valuable thing if we can execute it well. It's definitely a a very slow investment, like a very slow thing.

But if but it it's the kind of thing that, like, if we start it now and just continue this over the long term, it's a valuable asset, a defensible asset that we will have. This is the thing that that gets very, difficult about marketing in general. Like, we all would love to have these marketing tactics that we can just test in two weeks and know by the third or fourth week, like, yes, this is converting and we now we can triple down on it and now now it's working.

The landing page lead magnet, email follow-up sequence, that doesn't exist anymore. Not the same way.

I do see a funnel in this. Like I definitely see a path to us being able to run ads and run referral programs and things to get people onto the newsletter and into Coach Club. And then from there, you know, present them with a a deal to come into Zip Message. Like, there are definitely paths and funnels that we can build around this thing. But, you know, there's really no way to know that this is actually going to, you know, be like a a high converting funnel.

Just less It's

sort it's sort of just like an obvious valuable asset to have. Because we already know that that who our best customers are. There's a ton of research and actual financials to support that and interviews and all that. We already know that's the direction we're going in. So I'm now q four, I'm focused on the product.

We're shipping a ton of new features. But I need the marketing engines, the the brand, the content, the community, the newsletter list. I need all of that to sort of meet us where the product will end up in early twenty twenty three. I don't wanna be starting this community strategy or our content SEO strategy or any other strategies later. I want I wanna be starting that now.

I have people in place running it so that six months from now, once all these features have been shipped out, we sort of like meet together in the end at the end of this road. And then it's kind of off to the races from there.

So at some point, honestly, I think it might've been the NFT thing. The ability to gather a community of people who are interested in buying your thing. NFTs were weird because it was so financially driven, right? It was like, I wanna get into this NFT thing. So I get the airdrop and I find out first and then I flip and I make money.

It did flex a little bit the power of online communities these days where you can gather a lot of people and they become very interested in the same thing together. And then they go off and talk. And I think out of that and out of other things like this new science around community is forming and there aren't that many people that really know how to do it. It feels like a bit of magic right now on like, I don't know how to start a community or manage one or get people interested in.

That's the thing. I What are you starting to learn? Well, one one sort of thing that that that came to me pretty quickly, but it took me, like, years to finally realize this, is that alright. Because we we see a lot of companies just sort of spin up a a community. Usually a a Slack that's for customers of this product.

It's it's basically the the product sponsored community for customers of this product. Right? And we see that a lot. And that that could be valuable. But I think in general, that sort of just turns into like a support channel for the product, you know.

And it's so tied to the product itself that it's obviously just a marketing play. It's not an actual valuable community. Right? So the other thing that you see a lot with online communities, especially if the community itself is not the business, it's supported by another product, is that it's probably gonna be a ghost town. So there are actually two big problems with online communities, think.

One is it's either not active enough, so it's a ghost town, meaning it's not valuable to even spend time there. Or there's just way too many people, way too much noise. And what that results in is just very surface level, like, the discussions don't go very deep. It's always just scratching the surface. Mhmm.

Yeah. You can't be open and honest in that environment.

You can't be open and honest.

All those human stuff forms. Like a few people turn into the leaders and then they're like the popular ones and they start to control the culture of it. It's kind of

like, yeah. And for me, I've always gotten the most value from communities when they are small. I go to these trips in Colorado and Vermont. It's only ten, twelve of us. I'm in private mastermind groups.

And so that's where the the most value is. The most honest and open and transparent sharing and support and critical feedback and and comfort level happens. Sorta just clicked for me, like, two months ago. Was like, wait, what if we make our whole community around that idea of, like, it's small? You know, the smaller, the better.

Four four or five people per group. And then we can bring them all together in a larger community, but they they still get that small experience that's totally private to just them. And so that that's sort of like the like the unique value add of of or the unique, like, reason to even do this. Right? Like, we didn't wanna just sort of go through the motions of everyone's doing a community, so let's just start a Slack group.

You know, we didn't wanna do that. And then the other thing that that took me a little a little while to gain some comfort with it is the idea of using a separate domain, like coachclub.co. You know, because so many of these sites are just doing it like product name slash community. Like, it's all part of the thing. Right?

So I decided to put it on its own domain and then and then that brought additional questions like, well, if we're if we have our own domain name for this, shouldn't we send the emails about Coach Club from an at Coach Club email address instead of an at zip message email address? So I just I I spun up a a special email just for that. And like, now we have like a Coach Club Digest email newsletter, which is separate from our Zip Message emails. Yes. So it's like, it's a whole

That's a lot of faith to have in investment being made into

it. Yeah.

I I hope I hope you get re repaid for it.

At the end of the day, yes, I see funnels in this. Yes, it I see it as a list builder. I see it as, an audience builder. But at the end of the day, like, it's still just a good thing to bring our best customers together to talk to each other and meet each other. Like that's just generally a good thing for our small world here.

Yeah. You don't even need to be ROI minded or cynical in any way. You just be part of it and help facilitate it. And there will be plenty of benefit that comes out of it. It's even interesting to hear that you can email a list of people and say, do you want this?

And people just start to volunteer. Yes, that smaller group thing and help from one another, I want I want that. Right? That's

Yeah. And and they're enthusiastic about it. Like they're Mhmm. They they all immediately say like, I'd say 90% plus have like accepted the invite to to privately join this. And then they actually fill out a lengthy application form and write paragraphs about themselves.

Just, you know, so it's That's the other thing. They're not just like entering their email in one thing and then they'll forget about it. They're actually pretty engaged. Like they're all posting ZMs in their private groups and it's pretty active. So it's pretty cool.

Cool. I like it. Well, we're looking forward to hearing more about that. We have looked at that. I love the idea of it and we don't feel like we could do it.

You can't just spin it up and then not continue to put effort on consistent basis. It's just not gonna work out that way. It'll turn into a support channel ghost town.

Totally. I mean, I think that's one of the big benefits of bringing Claire on onto the team. Like, you know, she's she's now been on the team for, I think, going on three months. So, like, is not the only thing that she's doing at ZipMessage, but it's it's a piece of what she does every every week in terms of, like, running and administrating this community. It wouldn't have been possible if I didn't have that person on the team.

Like, I I do think it's a good idea for us to do, but I I wouldn't have done it if if it required any ongoing effort for for me, you know? I I just So I don't know how much time you have left. I wanted to touch on this thing about team updates. Yeah.

What do got, Connor? What do what do mean what do you mean by team update?

So I'm actually curious to hear how how you guys do it. I think we've talked about a bit about it. So, like, we started doing our version of stand up meetings with the whole team. And for us, we're a 100% asynchronous. So so starting from about two months ago or so, we so once a week, every person on the team is expected to post a five minute or so message.

And we have a single zip message running thread, you know, what did you work on last week? What are you working on next week? Any blockers? That sort of thing. And again, this is sort of like new for me.

Like in my previous companies, I we never did stand ups. Mhmm. You you were okay without it? I was okay without it. Like I always, especially in audience ops, I felt like it was like the update is like we just worked on our client projects and we produced articles the same way we always produced articles.

We was We ran all the processes.

Yeah. We ran all the processes. So there was really nothing. In SaaS, it is different and more exciting because we're constantly building new things, whether it's new features, new marketing. So as any other SaaS founder knows, like every week and month is different from the next, right?

We're always building new things. So that's what makes it exciting. I also wanted to do it as a way for the whole team to see what each other are working on, especially marketing and product. They can be in their own silos. So I wanted them to be aware of what's happening on on both sides.

But what I found, and and this speaks to one of my one of the reasons why I never really liked stand ups before is I just found them to be redundant and and, like, not actually adding a lot of value. So, like, it it would be a recap of, like, all the things that you that you worked on this past week, but we're so small that, like, we know what we what we all worked on this week. Like, we have separate threads happening in ZipMessage, in GitHub issues, in Notion, or whatever else we're using. Like, you don't need to report back on the things that we actually already talked about yesterday morning because we were working on it. So Okay.

So

so so there's that, but I didn't wanna kill the meetings altogether. Instead, I wanted to start to use them as more of a tool to push not only accountability, just to push our momentum forward. I I think that what we were doing wrong was they were too backward looking. We were we were looking at the past week and just recapping it when really the bulk of these updates should be focused on what's coming what's the upcoming week look like? And I wanted to make sure that everyone is pushing towards some goal, even if it's just four or five, six days in the future.

So now it's much more built around like, what do you commit to working on in the next seven days? And give us the update on where we ended up on your commitments from last week. So,

and and,

you know, I made it clear, like, I I don't expect you to be a 100%, like, shipped on everything that you commit to. I if that's the case, then then maybe we're not pushing hard enough. Right? Like, there there should be you should run into hitches. You should find new learnings as you go through the week and you will change.

But now it's like everyone is sort of like planning their week. And I think that that's also helpful for me to give input to everyone to help them prioritize. Like, okay, of those four things that you said you wanna work on, like, these two are the most important. Like And and a lot of that, like because I noticed that the team was always asking me, like, there are four or five things I could be working on. What should, which one should I be working on next?

And that to me like that to me is like the most important and probably the hardest thing that I'm always faced with. Like what is most important right now? It's no longer just the work that I'm doing. I have to make sure that, like, every one of my small team, every one of their plates is prioritized in a way that's optimal, you know, without without just working on things that are like spinning spinning wheels that's not making a big impact.

Mhmm. Is it a live call or is also async?

No. It's all all async. It roughly happens every Friday. Like, I'm gonna record mine. And I do it, of course, as well.

Like, I'm gonna make commitments for the week. Fridays, but we're all async in different time zones. So, like, sometimes, you know, it happens on Monday. Like, it it's just some sometime once a week, you know.

Yeah. We do I don't think it serves the same purpose in terms of accountability. That happens at the smaller grouping level between a back end lead and the back end engineers type of thing. That's where their regular daily, weekly standups hold accountability and use it as a public forum to share what they're working on, prioritization adjustments and so on. The challenge we had was just not coming in contact with each other often enough, and therefore just not maintaining that cohesion and a constant understanding of what's happening throughout the company.

And so we do monthly all hands for an hour. And those are great. It syncs everyone up. It talks about what's happening on the teams. It shows where we are on our growth expectations.

Are we ahead? Are we behind? Then it talks When

you say all hands, like that's literally every employee.

Every employee synchronous all at the same time, once a month.

Does everyone talk?

No, just the leads talk. And so that's right. That's part of it. You kind of have to do a good job or it's awkward or it's 28 people just looking at the screen, listening to me talk that sucks. No one wants that.

So we do think about what it feels like to sit for an hour and be someone on the team that doesn't talk at all. And how to make that, I don't know if entertaining is the right word, but like valuable so that it makes sense to pay attention and to take an hour of your day and some people are in Europe. It's 7PM, you kind of have to make it worth it. Otherwise it's not fair to use that time. So that was ongoing once a month.

And that feels good as a sync up, but we just felt like it wasn't often enough. And we don't like piling on more meetings. We're always careful of it. But we have now moved to doing weekly quick all hands with everyone. And it's like less serious in terms of attendance.

Like if you can't make it, it's not nearly as big of a deal. It's not like it's that big of a deal, but all hands you're expected to be there. And this standard thing, you've got a doctor appointment, you don't need to schedule your doctor appointment around it, you can just miss it type.

So do you record it?

We record all.

Okay. So there's always that, if you miss Yes,

it gives us a real standup. It's like twenty minutes and it's just like, okay, here's what BizDev is working on this week. We've a call with this person, we've a call with this. This is progressing. This feels like it's not going to work out.

Any questions? Next. And each kind of department does that quickly. And it's felt better. Right now we're in a situation where there has been so much product and development work.

And it's almost like I really want them to see and feel what's happening on the go to market to show them that all their efforts are being treated the way they deserve to be treated, with a lot of effort and getting benefit from all that work.

Yeah, man. Yeah. I mean, that's a big one for me. Like in doing these weekly updates, I wanna show the folks working on marketing what we are currently building and planning on the product side. And same thing with the product people to see what we're doing on marketing, you know?

Yeah, it matters. They are an audience that you need to keep very interested or they'll go elsewhere. That's a large portion of my stress is like performance anxiety for employees and investors Because everyone's got expectations and you want to drive things forward. And when I send that monthly update to investors, man, I do not feel good if I don't have good things to say there. The same way for employees, if we're not like growing fast enough and interesting and exciting things happening, I'm self conscious.

I get worried because people wanna be part of something that's exciting and feels like it's going in the right direction.

Yeah. You know, with the product side, I recorded a video, you know, again, we are planning a whole long roadmap of new features, especially aimed at coaches, a lot of stuff coming out. But, you know, to make sure that we're getting it right, I want to to design all the features, the the new UI, the new interface, and record a I think it's like a ten minute video of, like, walking you through what Zip Message will look like after we ship all these features. Not just like look, but like new capabilities that you'll be able to unlock. And, and this is all based on like these jobs to be done interviews that I did over the summer.

I recorded that and I shared it with the team to give them sort of like, I think to, to build some excitement. I think they were generally excited about like, like, wow, like this is gonna become a much different, bigger product in in a in a few months. But I also shared it with about 20 coaches who are who are customers. Some of them are former customers. And it's been an interesting process because I'm not usually this transparent with, like, actual UI designs and how functionality is going to work before we actually build it.

But I was this time because I wanna really make sure like, I'm not asking for their input on how how we should design and and build certain features. But I'm I laid out about seven or eight big new features that we're gonna be building over the next four or five months. And it's been really interesting to see the feedback come in in usually in long detailed zip message recordings from these coaches. Like, I would use this in this way and that in that way. My questions are, would it be able to do this or that?

I didn't see a button to be able to do this capability. Is that gonna be included? You know, like, getting that sort of feedback, it's almost like, man, I I should have been doing this more in some of the earlier features. Because there there was some details that I I didn't really include that we are going to include, thanks to this feedback. And seeing patterns like, you know, 10 different coaches all sort of resonated with the same thing.

It's another data point that helps confirm this this big bet that we're that we're making in in q four.

That that trickle into the team, including yourself is is very healthy. Did you say that was public public, like Twitter public or, like, to you

Not Twitter public. No. I only shared it with about 15 or 20 customers, and we have, like, private zip message back and forth off off of that video. Yeah. And I shared it with, like, you know, advisers and investors and stuff like that.

Very nice. Well, I think we gotta call it, my friend. Yeah, man. Alright. Good episode.

Thanks everyone for listening. Alright. Later, bro.