"Justin, I built a SaaS!"
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This podcast is distributed by Transistor.fm. Hello and welcome to Build Your SaaS. This is the behind-the-scenes story of building a web app in 2025. I'm Justin Jackson, co-founder of Transistor.fm. And I'm Harris Kenney, founder of AppOnSync.

Yes. Now, Harris and I have known each other for a while. Longtime listener of Build Your SaaS, right? Oh, yeah. And I wanted to have Harris on because he sent me an email with the subject line, I did it, I built my SaaS. And Harris has been sharing his story with me over the years. I know he's had multiple attempts. And I think what was exciting to me, Harris, is just...

This is hard. Doing this, building a SaaS, building a software-as-a-service product, and getting it to profitability is really tough and usually takes multiple attempts, as we'll hear. So I wanted to have you on because I think your story will be encouraging to folks who are in it. Yeah, for sure. Well, I appreciate being on, man. I mean, yeah, I listened to the...

the show for years. And so, and I had a bunch of attempts and always kind of look up to you from afar. We almost met in person at Podcast Movement when it was in Denver. And we missed. Yeah. How did that, because I was looking at that email too. And I was like, so you had emailed me like, oh, I'm going to go to Podcast Movement in Denver. And then we just never crossed paths. Well, I was only there for a little bit. It was when I was, things were really crazy at that time.

Okay. So I just didn't have a lot of time. So I was like, okay, I want to go. And I'm like, I hope I'll catch Justin. Yeah. Check out the boots, but if I don't catch him... So I just like... It was like what you've talked about for years of just like no margin. Like I've just been living a no margin life for...

a while. And so it was one of those situations where I was late and I had to leave early and I hoped I caught you, but it was just too tight. But there's a future with more margin where you're like, my friend's in town. I'm going to go do this thing. And I have time to do that. And I just haven't had that. Yeah. I mean, I think that's going to resonate with a lot of people. As an aside, this is something I've been thinking about for a while. You're a part of this MegaMaker community that I've been running since 2013. And

I'd like to do some more real-life meetups with Mega Maker folks. And maybe... I have to take my son to university in Toronto this summer. So I was thinking, oh, maybe we could do a meetup in Toronto. Where are you based out of, by the way? I'm based in Denver. You're in Denver. Okay. So yeah, I'm going to try to do some on both sides of the continent. And yeah, hopefully we can still hang out in person. Definitely.

I mean, assuming nothing tragic happens. I mean, I'm here and I would love to. And so I joined Mega Maker, but then left. And I had joined a bunch of things and left kind of like in the early days. Why did you leave? You just felt like it was too much. Not what?

What was the reason? So I left like everything. It's like I got off Twitter. I left microconf. I left mega maker. I quit my job in 2019. Yeah, let's go back to that. Okay, 2019. You quit your job, quit my job. I had had a bunch of bosses and I was my wife and I were thinking about starting a family and having kids and I just like couldn't envision being able to do the things I would want to do as a husband and dad.

in these like work environments I'd had for the previous decade. Just because they were, it was long hours or stress? Just not a lot of flexibility. It's like, you know, and like, well, what if I need to go to an appointment and the boss said I'd,

had at the time was, it's like, well, we don't really want you here. It's like, well, yeah, but like, I can just like do this stuff later on my computer. Like it's not, I don't know. I just didn't feel like I would be able to do it the way I want it to be. You know, I had, I had a great, like when I got into tech in 2008, I had a great boss, but even then I remember there being some things that graded on me that

One was, I didn't like other people looking at my screen while I was working. In truthfulness, like my day now, if you looked at my screen, you might not have any idea of what I'm doing. It could look like I'm wasting my time. It could look like I'm just sitting there thinking. A lot of my time these days is spent thinking.

And I didn't like people looking at my screen. And my joke back then was if I kept Excel open on my screen all day, people would assume that I'm working and productive, but I could be doing absolutely nothing. Right? Yeah. And then the second thing was I just... It felt so... Not humiliating, but...

to ask for time off always felt like this, like I had to prostrate myself in front of, like, can I please have some time off? And it just always felt like, why do I have to ask for permission? I want to be in a position where I don't have to ask for permission to, you know, take some time off or whatever. Well, do you remember Shawshank Redemption? You ever see that movie? Mm-hmm. You know, where like after they leave, after they leave,

And they're out. Sorry, spoiler alert. Yeah, yeah, spoiler alert. It's like 20 years old, but spoiler alert if you haven't seen it yet. They have a hard time going to the bathroom because they're so used to asking for permission. And they're like, oh my God. It just reminds me of that. And yeah, I mean, I felt like... It just felt arbitrary. I mean, I was in a role where I was in that position...

performance-based part. Part of it was like commission or performance kicker based on the team meeting its sales goals, but nobody else was. Yeah. So like I would need things. I would be like, Hey, like could we get this? Could I get, like, I just did a case study with a customer. Can I have, can I put it on the website somewhere? And the web team's like, yeah, we don't have like time for that. I'm like, okay, well,

I need to be able to share it with people. So then I ended up putting it up on GitHub or something. And then they linked the GitHub thing from the support center because the support team was willing to let me put it in there. And it was like, why is this so hard? And it was like, hey, I want data about who we've sold to. And they were like, yeah, our system doesn't really... It's in there, but there's no UI. So I was like,

I had done a little bit of SQL and database stuff in business school. So anyway, so I was just downloaded like dBeaver and I was doing my own SQL queries, doing all of this stuff when it's like... This is definitely the DNA of an entrepreneur. I think there's that feeling of...

It's not truly oppressive, but there's these corporate structures that can just feel like they're gating you in. And if you're a fast horse and you just want to run, this feeling of being gated in is such a frustrating feeling. Like I, and,

So good companies and good teams, I think, will reward that behavior, that kind of taking initiative. And I'm going to make sure this happens or here's a great suggestion or like, let's do this.

And I think old oppressive teams will suffocate or suppress you or make it harder for you to contribute in a meaningful way. That's how I felt. I think that the company was well-run and profitable and doing well. And so I was like, this is probably a me thing. But I was like, look, I've had a few jobs at this point. At some point...

maybe I'm the problem here and maybe I need to do the different thing. Because it's like nothing that they were doing there was obviously on its face. Like, how could you? How dare you? It was just like grating. It just felt like suffocating. But it made sense. Like, yeah, this isn't the web team's problem. It's not that big of a deal. Sorry, it's not a priority. But anyway. Oh, yeah. I think this is the realization is if you're...

a fast horse and you want to run, there's just some structures that aren't going to work for you. And that's fine. If the boss or the team or the culture or the business model or the market just necessitates something else...

If you really want a remote job, but the company is really an on-prem culture and you need to be there, well, you're just not the right fit for that place. Totally. I think what drives a lot of founders is that feeling of, you know what? I'm never going to be really... I mean, we're never really satisfied at all, but I'm never going to really be...

in my zone of genius until I'm able to be doing this on my own. Nothing will satisfy this itch until I'm in charge and I'm calling the shots. It's all reliant on me, but yeah. That's definitely it, right? So I was like, okay. I said, if I can get a project for 50% of my income... So at the time...

We had our first house. Yeah. We had our first mortgage. But that was like... So I didn't need a W-2 to get approved for the mortgage. Yeah, that's a key point. Check, yeah. Always get your mortgage before you quit your job. Definitely. Because you can always drive Uber, but they're not going to approve you if you're driving Uber. But there's a difference between showing you're making money and actually being able to make the money, right? Yeah. I was like, okay, we have the house. My wife was finishing her PhD.

And which was like itself a long journey. And I was supporting throughout, which happy to do like, yeah,

More than happy to do, but just like kind of the financial realities of the situation. And we hadn't had kids yet. So it felt like, okay, this is the window. Yeah. If I can get half of my current pay in contracts or projects, I will quit my job. And I had built up a pretty good network from my previous jobs. I helped scale a 3D printer company from 2017.

14 to 2019, we'd gone from 1.7 to $20 million in revenue as a hardware manufacturer. It was really hard, but I learned a lot and I met a lot of people because it was a really high visibility thing. So anyway, that's a whole other story for another day. But I had this other job in the meantime and

Worked my network. I got my commitments, basically. So I incorporated on April 1, 2019. I got my commitments. I quit my job May 1. And these were commitments for projects? Yeah. Go-to-market, client consulting, like, let me help you with your sales. Okay. So you emailed a bunch of people, said, Hey, I'm looking to make the jump. I need some clients. Will you be my client? Yeah.

And you got commitments from enough of them that you felt like, okay, I could... And what did those commitments look like? Like there was just a pipeline of work? Like you had six months of work or... Let's do it. Like signed, closed, contract signed. We're going to start next week. So I was like, okay, I'll work weird hours. I'll make this work until I can get to 50%. Got it.

So I waited until people were like, okay, we're going, we'll pay you kind of thing. And did you have a goal in mind? Like, I need to get this number of people on retainer or... It was just half of my income. I forget exactly what my income was at the time. Yeah. But it was just half. I figured if I could get to half, then I could get the other half is what my guess was. So I saw one contract. Basically, one contract was enough, but it was only a two-month contract. So I was like, okay, I've got two months of half my income. Yeah. Let's go. So I quit my job. And I figured once I quit...

I would, and I talked to some other kind of mentor type people at the time. And I felt like once I quit, I'm going to unlock 40 hours a week of time. Yeah. And so like, I'll be able to do way, way more with that time. So, and that was right by the end of June or by the end of May, by the time I got to June. So I was, I was back to my old income within a month. Oh, wow. Yeah. So it was like, oh, okay.

Okay. And it was just me in my house with one laptop. So it was like all profit margin with no expenses. And so it was a really good start. Yeah. But that drive, some people quit their job. They have all this extra time.

And they find it's actually the opposite. Without somebody driving them, without somebody pushing them, they don't have that relentlessness you need to go out and find clients. Yeah. And I think that's a good litmus test. It's like once you have the time...

Do you have the drive? After I'd quit my job, there was times where, for example, course sales weren't enough. And I was like, I got to go build some WordPress websites for people. And it's just this dogged...

relentless drive to say, I'm going to do whatever it takes. I'm going to email 100 people until I sell 10 website contracts and I'm going to build them all and then live to see another day. Yeah.

I think the anticipation of like, that we would be starting our family, I mean, like within a year or so, our daughter was born. And so I think that was like, I had this in my head of like, I've got to kind of get this thing off the ground because things are... So that to me was a big motive. I can't like, I can't disentangle that. Yeah. Yeah. Dependence is a huge... That's true, actually. Like before I had kids...

I didn't have that same drive that I did after once I realized, wow, this is expensive. It just keeps going up. Yeah. And expensive in a sense, it's expensive with your time, your energy, but your money, it's just like...

You can't just live in a one-bedroom condo anymore. You've got to get more space. You've got to get a car. You've got to get a car seat. Yeah. Oh, yeah. Totally. Yeah. There's just hard cash flow hits that come with that. Yeah. So 2019, you launched this. You get some clients. Yeah.

COVID hit in 2020. So did that affect you at all? Yeah. Yeah, yeah, yeah. So terrible timing. Just couldn't have, really couldn't have done it worse in a lot of ways. Why? Because it affected it poorly? It was just so stressful. And then we were expecting at the time. Yeah. So every time I got to the... I mean, in the beginning, it was really unknown. And then especially because we were expecting during that time, it was really...

anxiety inducing. Um, and I think the biggest thing I realized was like, what if I get sick? So I had these clients and it's going well, but like, they're just really paying me to talk to them about stuff. Yeah. And like, we're getting some results definitely. But like a lot of this business is just like, I've been doing this and I was working with a lot of hardware companies at the time. And so I just had a lot of like offhand things of like, Oh, well you should talk to this distributor. They would like totally pick that up. And like, I knew that because I had been doing it for seven or six years and

So that was like worth it for them. But I was like, what if I get sick and I can't take that call? Yeah. Like, are you going to keep paying me? Probably not. So it felt very fragile. And so this is when I started discovering...

And I joined... I forget the exact date, but I joined MegaMaker and I started listening to Build Your SaaS and startups for the rest of us. And I joined MicroConf. Were you familiar with software as a service or web apps? You came from a world where you're selling hardware. Yeah. I didn't have software background. I mean, I did ERP consulting in 2013 as an account executive. So no. I mean, I'd never worked for a SaaS company.

at all. I'd never worked for a company that had a dollar in SaaS revenue. How did it even come on your radar? Like, how did you... I found Rob Waller

walling stuff first and that tipped me off in SaaS. And then I found build your SaaS and transistor. Okay. And then it, and then it just kind of like was like, cause, cause what I wanted was like to take care of my family and to build and to build a good business. So then it's like, yeah, what kind of business? And so because of like the pressures of COVID and family and like, I'm in my late thirties right now. And so, and I had like finished business school. I like, I had, I think very compressed learning cycles of like,

very quickly, like, this is a good idea. Let's go. Okay. But it can be better. And just like, I didn't, it's taken a long time to get here, but within this, there's been like really tight learning loops and

And then it was like, oh, this is it. I went out to work on my own because I want my own business because I want to be present as a dad and provide my family. And this is the best way to do it. It is a SaaS. I need to figure out how to have a SaaS somehow. I mean, it doesn't seem that long. If you think about it, it's been six years. Yeah. It's been five or six years since you even realized what the SaaS...

market industry category, how it works. So that's pretty compressed. I mean, I guess in hindsight, yeah. It feels like a long time. It feels like a long time. But I mean, once my actual idea hit, it took off really quickly. So it was a lot of tight, hard learning. But having to maintain cash flow the whole time. There was no like, oh, I'm going to go on the sabbatical and think about it. It was like,

I'm staying up late to try to figure out how to do this thing because during the day I'm on client calls and stuff. I think what's interesting is that poll that you just described, I think is quite common for people investigating, especially this space, because that was always the promise is like, okay, what do I desire? Well, I don't want to work a job.

Then you try consulting and you're like, okay, consulting works, but you have to keep this thing... Every sales cycle, you're starting from zero again. I mean, it's not really zero, but it can feel like that. Oh, no, definitely. Yeah. I mean, basically, unless you start developing IP and...

Yeah, I mean, I guess the reason I say it's not always from zero, because you still have your network. You still have former clients you can go back to and say, hey, let's do another engagement or whatever. But it can feel like you're always starting from zero. Yeah.

And then there's the stress of that and delivering projects on time. And even having to wake up early. I had to wake up early and do calls with people in Sweden. So it was like I had to wake up at 4am or something. I was like, this is tough. So then you search for, okay, what are some other options? And you're like, oh, recurring revenue. If I could just have...

Instead of having to rebuild it every sales cycle, every month or every quarter, just every month, new stuff can come in. And then you go look for solutions. And it's like, oh, I could build a SaaS business. Exactly. So that's how I kind of landed on it. But then I'm like, okay, I got to learn about SaaS. So I joined all these things. And I'm super active on Twitter at the time, just absorbing, absorbing, absorbing. And I feel like I was just in like...

Just constantly downloading little things and thinking about surfing and all these analogies and the stair set method and da-da-da-da-da. But I think in general, what I was feeling was like...

Okay, this is too much learning. I need to be doing now. I need to start testing ideas. I'm like, where is this idea going to come from? How can I turn this consulting business into maybe something that's a little bit more of an engine so I can free up, make more money, or just free up a little bit more time? So it kind of converted into a little bit more of an agency. Because at the time...

Like email deliverability started to become like a little bit of an issue discussed in some of these corners of the web. And most of my clients, they wanted to talk to me, but if they were really hard and clear, they would say, well, I want leads. Yeah. Like, I'm talking to you and I like your advice and there's some really good ideas in here, but like ultimately, what do we need? We need new leads for our business. And like, can you get us leads? And I had never done that before.

The companies I'd work with in hardware, it's different. The go-to-market is really different. And so I just started learning cold email. I bought a cold email course for like $100 on Twitter. And so I started learning cold email and started building an agency around outreach as an extension of this consulting service. And so then I started getting really deep into that world.

And we became a HubSpot solutions partner. We were doing outbound. And then the landscape started to emerge of like, okay, these are the tools I'm using. These are gaps between these tools. This is how they charge. This is what's annoying. And then within that, I had had a few different ideas. So I left the communities and stuff, not because I didn't like them, but because it was like,

what I need next is not here. Yeah. What I need next is out somewhere in the market. And like, nobody here is going to be the one who's going to be my first customer or, and so, and so I only have so many. And at this point, my daughter was born. I was just like, okay, I don't have that much time. So I got to go. And so I like, I literally deleted Twitter. I literally left like everything. And I just started spending like all this time on LinkedIn and, and, and,

So that was kind of that transition period and the beginning of what was like testing ideas. This is so key. You're going to need some foundation of knowledge. But after you've got a reasonable foundation, you need to go out and do stuff. You need to go out and start building things.

And I felt this like I started the Product People podcast in 2012. And, you know, after a year of doing these interviews, I felt like I got to stop doing these interviews and I've got to do something like I got to launch something.

exactly the same as you. Until I start putting this into practice and really feeling it, it's just like anything. I can describe to you the mechanics of snowboarding, but until I get you out on the hill and you start to actually try it out, the head knowledge is fine for you to have the basics, but you need to start

you know, you need to just start going down the hill at some point. Yeah, exactly. You got to land on your butt and be like, okay, yeah, that was fine. So that's, I think that's great that you had that self-knowledge probably driven by the fact that you didn't have very much time. That was it. It was like, oh man. And it was kind of like a little sad because it was like, oh, like this is fun. Like I like talking to these people. Like this is funny. This is my community. I'm home alone. I have no real coworkers. I'm

All my friends have jobs. And then we have a young kid. And so I don't have a lot of time in general. When I'm not working, I'm trying to be a dad as best I can and trying to be a husband. And so it was a little sad, honestly. But I just didn't feel like I had... All of these things, I felt like I didn't have a really good alternative. It just felt like I got to do this. If I want to move forward, I have to make some changes here. And it's going to be...

you know, a little uncomfortable, but it's, I just don't, what's the alternative. Yeah. Okay. So you get this agency going, agency's going and it's working or what, what happened? Like it's working, it's working. I'm acquiring customers. Like I'm starting to like feel what it's like to get on a wave a little bit because with my consulting, like I had this feeling of like, yeah, I've got these relationships, but like, I don't have that many relationships.

Like at some point, this is going to go away. And then what? But now with the agency, it was like, oh, this is a problem. People are landing in spam. They need new leads. Like I can productize around this. There's some tooling around this. Like, and so it was working. I was, I was getting customers, retaining customers. It wasn't taking off because it was me. I had contractors who, some of whom were really wonderful, but like,

I was never able to fully delegate. So it had these ebbs and flows as I tried to balance sales and delivery. But then, and this is like the worst, you're not supposed to do this. This is like the worst advice. I think maybe the lowest paying client I ever had in the history of my agency. I mean, I think I have to go back and check that. I mean, he was paying me almost nothing. Yeah.

Because some months are like, sure, okay. Yeah, yeah, yeah, exactly. You got to hustle. He was like, you know, I really want this cold email data from SmartLead. I really want it in HubSpot. And I was like, oh, yeah, like we're HubSpot partner. Everyone in HubSpot always talks about inbound, inbound, inbound. In fact, everyone in the HubSpot ecosystem is constantly like,

at this time, really posturing against outbound. Like that's the whole positioning of HubSpot is inbound. So they're constantly criticizing it. And I was like, well, that's kind of an interesting thing to be like the outbound person in HubSpot ecosystem. Like nobody's saying that. That would be... And then it made sense to me. Like, well, yeah, of course you would want this there. Yeah. You get a lead and then you need to manage it and they become a deal and then you close the deal and then they become a customer. Like...

Yeah, right. Like, duh. Why isn't anybody doing that? And what I didn't realize at the time, but I now realize is that like, these tools were very like on the edge. They were like growth hacking tools and bigger companies that had those requirements weren't using them. Or they weren't using them like they use the rest of their tools. So it was like a bet basically at the time of like,

if this way of generating new leads takes off, then new tools will be required to coordinate or orchestrate the new tools with the old tools. Yeah. If it takes off. Okay. So a client is paying you to help them manage... When you say outbound, you're talking about sending cold email, trying to get leads. Yeah. And this client says, this is good.

They weren't paying... They weren't a high-value customer, but they said, this is good. I really want this... Once you get me a lead, I want this to move into HubSpot, which I'm using as my CRM. And then as you were looking at HubSpot, you're like, oh, this is weird. Because HubSpot's whole philosophy was all around content. You use content to attract leads. So there are inbound leads. They sign up on your blog posts to get the...

PDF, and then you manage the relationship that way. But not a lot of people using HubSpot were starting with outbound. No, no. Yeah, at least not publicly. But then I realized, actually, quite a few of our HubSpot clients are doing outbound. Yes. And actually, HubSpot themselves has a huge sales team.

With a few hundred salespeople. And they totally do outbound. Yeah. So this seems like a gap. This is an opportunity. Exactly. So what did that translate into? What did you do with that information? Well, so I started to build something. So I started to build it in make.com. Okay. SmartLead had webhooks. And I thought, okay, well, I can take these webhook payloads. As these events occur in SmartLead, an email is sent, a reply is received.

as these happen, I can take those events, map them, and push them to HubSpot. Okay. Like, I remember saying, like, how hard could it be? You know? Yeah, yeah. There's this quote, we do things not because they're easy, but because we thought they would be easy. Yeah.

That's the entrepreneur's mantra. Yeah. That was it. The pinboard guy said that. I think about it all the time. I remember literally being like, oh yeah, like how hard can it be? And I said that to him.

And so, so this is, um, uh, May, 2023. So, um, did we miss a part here? Cause you did try to build intro CRM. Oh yes. So my agency was called intro CRM. Yes. Sorry. I covered some of the, I missed, I skipped some of the SAS stuff cause, cause it was never a SAS. Um, I tried doing intro CRM as a SAS and now my agency just became interest CRM, but we never, I never had a single paying customer. I built something in bubble. Oh man, sorry. I forgot. I haven't thought about that. Um, in like, in like

No, that's okay. Yeah, yeah. So, oh yeah, it was so bad, I don't even remember it. My first I saw, it was a CRM. Yes. So you were doing this agency and then you're like, okay, I'm going to try to build some software. Yes, right. And then you built this tool called InterCRM in Bubble. Yes.

But it didn't really take off? It didn't really work? No, not at all. So it was like, my thought was like, I was using Basecamp. Oh man, sorry. Oh, I totally spaced on this chapter. So I was using Basecamp and I was like, oh, Basecamp, they're discontinuing HiRise. Like there's no CRM like Basecamp and they're not doing HiRise anymore. There should be a simple CRM for everybody that everybody can use. There's an opportunity. And I mean, HiRise was, I think, doing, I don't know, three to five million a year or something like that. Like it was, it was...

on Basecamp scale, it wasn't successful, quote unquote. But for most of us, that would be an amazing business. Exactly. And I thought like, okay. And I really looked up to Jason Fried and David Heinemeyer Hansen. And part of my idea of going from agency to SaaS was exactly what they had done. So they were really influential in my mind at the time. I don't know. It's hard to know. When I'm being self-critical, I would say, well, they were really running a design agency. They were really craftspeople. And what was I doing? But I think I'm probably being a little hard on myself. I think...

I was doing hard stuff. And I think it ultimately has translated into a good product. And so it's like sometimes it's hard when you see these people from afar. You kind of... Yeah. It feels unattainable of like... But they're just normal guys too, working hard and doing great things. But they're just people too. In hindsight, I feel like I...

I created too much distance in my mind between what they were to do and what I would be able to do. How could I ever do that? They're just humans too. I mean, they are very gifted in many ways. But earlier in my career, I applied for a job there and flew to Chicago and spent a day with the team.

And that was my sense after that day was I had like kind of put them up on a pedestal. But then after spending a day with them, I'm like, oh, these are just human beings. Like they're, there's, they are, again, they are good at what they do. They're skilled. It wasn't like magical. It was just like, these are just people doing work.

And they've achieved something. And I think they would probably be like the first ones to say that, right? Yeah. Yeah, I think so too. They would be like, I mean, I don't think, you know, they just have a brand. They did it early. They've done it at an incredible scale. And I think... So, yes. So, Intro CRM was my first SaaS idea. I built it with Bubble myself. I got help from...

So my first idea was an integration. I was like, okay, so there should be a CRM that integrates with Basecamp. Because I thought the first tool that people adopt is project management software. Because you have a couple of clients and you don't need a CRM yet. So you start with a project management software like Trello or Basecamp. And then you start to get more clients. And then you realize, oh, I kind of have to manage these leads. I need a CRM. And so my thought was the first thing that should integrate should be a CRM. But the core system of record is actually the project management tool. And they kind of go back and forth. So that was my first idea.

And so I had Lola, LunchPail Labs. She built the integration for me. We integrated with Trello and Basecamp. And oh gosh, I can't remember it now, but there was, I think, maybe a third...

project management tool that we integrated with because I was working with all these founders and they were in project management tools all day. And I was like, oh yeah, so they would maybe use this and they're not using HubSpot because it's too bloated. Yeah. And there's too much to do. And so you tried to sell it to folks but it just didn't work? I was like, well, so we have this basic CRM and it comes with these services. Okay. And they were like, we just want to work with you. We don't

We don't want your CRM. Got it. So when you pitched people on it, they were like, we just want the services part. Why do you think they didn't want the CRM? What were they using instead? They just didn't check it, didn't log into it. I had an amazing client and she...

She was just very kind. And I felt like if anyone, she would have just logged in just out of curiosity and sympathy or pity. And even she had never logged in. So I was like, okay, nobody cares about this, really. I think what's interesting about this is your hypothesis seems reasonable. And so then there's different questions. Is it the way you're marketing it? Is the way you're positioning it? Is it the actual product isn't solid? Yeah.

So those folks that weren't logging in, what were they doing instead? What were they using instead of your CRM? Were they just using no CRM? There wasn't actually any movement there? Yeah. They would use nothing or they would use a Google Sheet or they would just manage it out of their inbox. I think there's a version of this, but I don't think I have founder market fit to build it. It has to be a product-led thing that...

It would have to be like, you just drop in and like now...

With AI and these AI native tools, I could imagine there being a CRM that connects with Gmail. And it's like, and if your business is small and simple enough, if it connects to your calendar and your inbox, it will maintain their data model for you and create little deals for you. I could actually see that today. Yeah. And that would be good enough for this kind of user. Because the problem is the entry. The like logging in, logging out, updating fields, like nobody, it just wasn't worth their time to do it. Yeah. Yeah.

And then when they got big enough, they hired somebody to do it. And then that person wanted a real tool. Yeah, and then they would... So you were in this kind of in-between... Intro CRM as a software product was in an in-between state. And that was not quite right. Yeah, it just didn't quite land. But I was right that people... The core idea of these things don't talk to each other, that has a thread that has been true for a while. And even back to the 3D printing company...

Even back to the ERP consulting company, partnerships has been the thread of growth through 15 years of my career through the companies that I've grown. That is a continuity thing. My idea of these things don't talk to each other. That is now fundamentally what AppOnSync is built on today. I think that is such a crucial observation. Yeah.

It doesn't mean your hypotheses will always be correct, but that alone is just true. And in an AI world, I feel like that's more true than ever. Everybody's typing into ChatGPT and Cloud

But there's still not a lot of glue between... Claude could tell you to go do something, but then you've got to... There's this chasm that you've got to jump over. You're the one that's got to go do what it just told you to do. Yeah. And there's going to be more and more glue needed between these things. Yes. And I think...

I think there's going to be a lot of opportunity just in that. Even Zapier integrations break all the time or they're not quite right. There's just all of these holes, all of these little opportunities, all of these little friction points where it's like, ah. Another one I've observed is if you go to a retail store and

I would ask owners about what they were doing and they're still entering inventory manually. And you'd think, man, there's a barcode on every product they get in. And you'd think that the supplier or the distributor could just send them

some sort of JSON, some sort of data that would just populate their point-of-sale system. But still, in 2025, and still with modern point-of-sales like Square, they're still entering data in manually. And again, maybe there's not enough money there or friction. The economics of all that, of the opportunity might not be there, but the thread is correct. Yeah. And I think you've identified...

There's still so much manual data entry right now. There's lots of opportunities here if you're looking. I think so, absolutely. And here's the thing. So someone would say, well, yeah, of course you got to enter this thing into Cloud and then you got to go to the other thing. Well, that's where MCP servers come in. And that's why agentic workflows are so exciting. I mean, ask any developer...

Hey, so tomorrow I'm going to publish our database schema. No, nothing will be lost. No security issues. I'm just going to publish it and post it online. And like, do you, would you be proud of that? Do you have any issues maybe with the tables and the labels? Do you feel like our database is well-documented if you were to get hit by a bus tomorrow?

I mean, how many developers would be like, yeah, no problem. Open Kimono. Let's let the world see. And so if that's the case, if the developer who's building and maintaining the code doesn't feel like it's exceptionally well-documented to them, then how the heck is Claude going to know what to do? Yeah.

It's going to stumble. It's going to stumble in the tables and it's going to stumble in the... And you can say, well, they'll figure it out. How? There's all these nuances, especially when you get to the edge cases. And the edge cases are sometimes what matter the most. The edge cases are what's real. This is why every time I look at a demo, like somebody releases some sort of demo, it's like, okay, this is not a real company. This is not a real use case. This is not nothing. This is all fantasy. But, you know, come into my world and it's even like the...

Like right now, when I am trying to level audio, I use this tool called Ulean Audio Meter or whatever. It tells me the loudness in loops. But then I take a screenshot of that, bring it into Clod,

Then give it the, there's these built-in Apple audio filters. I say, here's the audio filter, AU Dynamics. Tell me what to use here, like how much gain, how much release time, all that stuff. That is friction. Right. And you think, you know, there's a modern world, like maybe with Apple shortcuts, I could do something. And the truth is, it's still a lot of friction to get something from one system to

to another. And for most users, that still exists. And there's just a lot of opportunity there. If there was a tool that, in my case, like maybe a web app or something, that automatically gave me a loudness score for my raw audio, and then told me what to do, or just automatically did it for me, I might

I might pay for that, right? Yeah. That's how you discover problems. Yeah. Well, that's where, yeah. And that's where it gets complicated. Yeah. But no, I think that like with it, I mean, with AI, I mean, imagine if you had like a library, you know, like a physical library, but like no card catalog. Yeah. It's like, okay, well, how are you going to find the book? And I mean, at some point you're expending and this is the thing I think people aren't talking about. They say, oh, this is the worst it's ever going to be. It's always going to get better. Like, well, maybe there's also like a lot of money being spent right now. And like,

At some point, there's going to need to be a return on these things. And at some point, they're going to start charging more. And so, I mean, yes, I understand that in theory, things will get better, but like nothing gets better forever. Yeah. I mean, the only thing that grows infinitely is cancer cells, you know, and then you have like system collapse. So it's just like, I like AI. We use it. I tried building a GPT wrapper. So let's talk about those other SaaS ideas. So intro CRM didn't work.

But then I got into this, they wanted the service. So I did the service and then they said, okay, well, I'm giving them lead lists to give me feedback to score them so I can make them better lists, better fits. Yeah. Because I'm using like database tools like Zoom Info and Apollo. And I'm giving them Google Sheets. And so I was like, oh, this is a SaaS. Yeah. Lead Raider. I built it with Glide. I give you like a sample set of leads. You can

swipe through it like a dating app, say which ones you like, say which ones you don't. I'm going to take that feedback and I'm going to go build a better list. That also seems like a good idea. Yeah, it wasn't like the worst, you know? I mean, it's kind of like an LLM concept, right? It's like reinforcement training from the person who knows. It took a lot of work and again, they weren't spending the time on it. I don't know, it just for whatever reason, it didn't quite...

People didn't want to do it. Or they were just getting too lost in the weeds. And I was like, yeah, I understand what you're saying, but we just need to send some email. And if it's not a fit, they just won't get back to us. It's okay. It doesn't have to be perfect. So I don't know. It just didn't work. You know, that's such an interesting thought I just had.

Because you've mentioned this twice now, which is like, they couldn't take the time or make the effort to log in. Or they couldn't take the time or make the effort to log in, in this case, score some leads or whatever. Yeah. I think this happens a lot more than we realize, which is, there's just a certain category of applications that...

where you're not going to get people to log in. And that's difficult. It's like, I'll use this as an example. I actually love this tool and I pay for this tool, but I think it's still a good example is seotesting.com. I love this product. You know, they're friends of mine. I think it's a great product. But my interaction with the product is basically at this point, 95%

just through the emails they send me of, here's this month's top keywords. Here's the winners and losers. Am I setting up a lot of SEO tests? Not really. And that's, I think, because there's just only so many apps I can log into regularly. Right. And even like, oh, I've got these analytics. You're going to log in and get these analytics. It's like, well, the only apps I really do that for...

is revenue analytics because money is important. And then performance-based metrics on content. Yeah. Blog, website analytics, and podcast analytics, and YouTube analytics. I'll look at all of those. Anything outside of that. It's just like, oh, you want me to log in and score a bunch of leads? It's like, that seems like a good idea in...

as a concept like yeah i would like to do that i would like to get better leads and yeah i could see even a fun interface like like uh a dating app like i could see myself doing that but at the end of the day it's another thing to log into exactly i i only have so many spaces in my life for things that i log into hey how come your team doesn't have their own podcast

Head over to Transistor and use my coupon, transistor.fm slash Justin. You'll get 15% off your first year of podcast hosting. Exactly. Yeah. That's interesting. So it just like, it didn't quite click.

So then the third idea that I had was Draft Studio. This was like an early GPT wrapper product. I actually used it internally. So in cold email, there's this thing called Spintax, where you give it a word and then you give it variations of that word. So like, hello, hi, hey, hey there, greetings, good morning, good afternoon, whatever. Yeah.

And so you could take an email or you could take a phrase, drop it into Draft Studio. It would spin up permutations of that and then spit out spin tax that you could just drop into Smart Lead so that your emails would be different from each other, which would help with deliverability. Yeah, actually, I liked it. I used it a lot. It was useful as AI has accelerated. And it's just made some of these things less necessary now. People are making...

fully unique emails every time. I just kind of knew it didn't have a long-term potential. I liked it as an app and I used it a lot. I did have a few people who used it a lot and liked it too. But it was just as a GPT wrapper, it was too...

to really go anywhere. And I kind of always knew that. I was busier with the agency. And that also seems like the kind of thing that eventually, if I could figure out a process for doing that in ChatGPT or Cloud, I would just do that. Totally. Yeah. So...

But it was okay. But it was technically a SaaS. I built it in Glide. I thought about charging for it. And then... So all of those things happened between when Interest CRM... I registered that domain in 2020. Yeah. And then I started building up on Sync in May 2023. Okay. So that was my fourth idea. Yeah.

My fifth idea, which I've almost not really talked about very much, but it was card importer. HubSpot's default card importer is actually really not great. And so it was a really basic, take a picture of your business card, scans it into HubSpot. It's actually a really big thing. There's a lot of HubSpot comments and forum about wanting these features and

I posted a YouTube video. I still get messages on LinkedIn about it. People being like, hey, is Card Importer still available? So I actually think there's something, but it was my fifth idea and App On Sing was taking off, so I just didn't do anything with it. But of the ideas, it was probably my second best idea

but it would need more around it to become something. Yeah. But I guess my point is not all of my ideas were bad. Yeah, I mean, I think that's what's interesting is none of these ideas actually seem bad. They all seem like reasonable bets. And it's kind of like you can follow...

All of the advice for looking for business ideas, like you go into the forums and what are people commenting about? You had consulting clients and you're listening to their pains and their friction. And that's all a part of it. And basically, you're doing all of that work, which by the way, I think like 90% of people don't do that work.

But it's that work that sets you up for some good at-bats. Yeah. And I think the truth is, you look at professional baseball players. These are people who have trained their entire lives to hit baseballs, and they have a hard time hitting baseballs. Totally. Right? So you can do all of the foundational work.

But their chances, their odds of hitting a baseball are much higher than mine are, right? Totally. So all of that foundational work matters. You've got to do all that work to get up to the plate and have a reasonable shot at

at hitting the ball. And then even then, you might hit it, you might foul, you might walk, you might just get a line drive, you might get a home run. Those are all opportunities. Those are all potential outcomes. But

It's still like a lot of players get up to bat and they strike out. Right. And they're good players. Well, what's the number? It's like if you bat 300, you're in the Hall of Fame or whatever. There's something like that. Yeah. I mean, I'm actually not a baseball fan. Yeah. I'm not either. But I know there's some number where it's like not that many. And if you actually hit that many, you're like one of the best of all time. Yeah. I mean, this is the whole point. I think this is why sports is a...

In some ways, sports is a bad metaphor for business because sports really is zero-sum. Right. And business has... There's more opportunities. There can be multiple CRM software providers and you could still win. Totally. But I think what's instructive about your story and my story and really almost everybody I know, almost very few people get up to bat...

and hit a line drive or a home run their first at-bat. And I also see in entrepreneurship, there are a ton of people who have not done the foundational work. They don't have clients that they're observing and seeing where their pain points are, seeing where the gaps are, seeing where the opportunities are. They're not looking at the forums. They're not exploring and evaluating ideas in this way.

They don't have a network. They don't have any skills. And so what is the success rate of any given entrepreneur stepping up to bat? Well, it's nearly zero because there's an infinite number of people who want to do it. But like I said, I think 90-95% of them aren't even doing the basic foundational work to even have a chance of hitting a baseball. Yeah.

Definitely. You do the basic foundational work to give yourself a chance. And then after that, it's like, we'll see what happens. Hit this one. Okay. I barely got on base. Yeah. Well, it's like the harder I work, the luckier I get. I definitely think this was a lot of work. So because of all this, when Outbound synced, when I did that,

And I started talking about it to people. I was like, oh. AboutSync is the idea that you're working on right now. Yeah. This is the one that worked. Yes. I've been doing this for two years. It's profitable. We've got three people on the team. We've been growing 10% to 20% every month, literally since October 2023. But there were things that were happening with it where I was like, this has never happened before. Okay. This is different. Let's explore that. So you went through these other ideas. Yeah.

All of them are like, maybe you get on base, but it's not really... Or maybe you don't even get on base. Yeah. And then... Maybe you buy a domain. Yeah, maybe buy a domain. So what was the genesis of Outbound Sync? What was the observation that you're like, oh...

Yeah. This is worth doing. So I had that client. He said he wanted them to talk to each other. I said, okay, sounds interesting. Built out a basic version of it. And then I started posting about it on LinkedIn because LinkedIn is my only water cooler at this point. Okay. Because I figured the people who, if I'm going to build something based on the space that I'm in, they're going to be there. Yeah. Probably. So I start posting about it there. I push about it in some WhatsApp groups and I get some people biting. So in Outbound, a lot of people are in WhatsApp groups, just by the way. Okay.

I don't know why. It's very international. There are some biases, but in general, it's pretty meritocratic. I've got a lot of people who I talk with who I don't know their name, I don't know their face, I don't know anything about them. But they're in these groups and they're kind of like anonymous, like growth hacker chats. How did you get in those WhatsApp groups?

That's a good question. I don't... Well, when I was running my agency, that's when I got exposure to some of those chats and other agency owners are in some of those groups. Okay. And they'd say, hey, you might want to join this group. Yeah. Oh, yeah, exactly. And one of them, they were promoting it to like, hey, join my group. And there's no caution that I just kind of joined the group, share best practices. There's kind of like a guild. It's kind of like there's honor among thieves. The best outbound people all know each other and they all talk. Yeah.

And they all share notes and they don't consider themselves as really direct competitors in a traditional way. Yeah. Like it's very interesting. It's very unusual. But I really think that, yeah. I do think this is a key action that a lot of founders don't take, which is you said, I'm going to get off everything that's a distraction and I'm going to go where my clients are. So LinkedIn is a natural choice. Yeah.

And then you're also getting in these WhatsApp groups. Yeah. And I think when you're thinking about where to invest your time, I don't think people realize that in a given industry or category,

This is why I think actual participants in a given industry or category have such an advantage over somebody who's just flying in because it looks like a good business opportunity. You have to be simmering in that community. You have to be soaking in it. You have to be in the water every day. And there are just things you can't...

experience and they're, they're really subtle unless you have this constant drip of being in a WhatsApp group every day and seeing what people are talking about and you're building those relationships and you're making these subconscious observations. Yes. Right. Unless you're doing that, like I think it's pretty hard to,

I think it's hard to build a podcast hosting application if you're not a podcaster. There's just something about knowing the pain, about knowing lots of other podcasters that are trying to do it too, of knowing what it's like to conceptualize a show and then record into a shitty mic and then try to publish it and then be listening to it and hearing background noise and cringing and that whole process...

Until you understand it in an organic way, like I could describe it to somebody, but until you've experienced it, until you know the pain of releasing something publicly and having people not respond to it or trying to get distribution for it or trying to get people to notice...

You just don't understand. And it's the same thing with outbound salespeople, outbound leads people. Do I really understand that category as an outsider? No. And so if I try to swoop in and say, I'm going to compete with Harris, Justin Jackson tomorrow. I'm just going to start a new app. You have such an advantage over me.

Even with ChatGPT, I could get all the intellectual information. Tell me about the outbound world. It might be able to even pull in stuff from Reddit and stuff. It's still not the same as being in the water, as surfing that spot every single day, showing up with all the other surfers, looking at those waves, seeing the weather and how it rolls in. Nothing compares to being in it. And I think it's actually almost...

There are some entrepreneurs that have been able to serve an audience or a category that is not their own. I think it's exceedingly rare. And almost always there's some venture funding in it where you have runway to really give yourself a crash course in it. I think it's so tough. I think you got to be in it to really have an advantage, especially as a bootstrapper.

Definitely. And so what's funny about where we are today is that those two places I was spending my time represent the two parts of the business. We'll keep riffing, but the agencies are not our direct customer today.

But they're our peers and they are the channel that we sell through. And I consider them friends. I mean, I've had agency partners who have gone through some personal things and like I've done, it doesn't matter the details, but like I've done personal gestures for them just because like I love them. I just like, I love them. And if they, if they, if so, like truly I consider them like friends.

Yeah. And if they were here, if they were like, if someone needed something, like I would do something for them and I have done something for them, not because it's like a marketing thing, but because it's like, Hey man, like I love you. We've been in this stuff together. Like we've written these ups and downs, like the Google shut down all these things or Microsoft, you know, this happened wherever. And we've kind of been through these experiences together. Yeah. You know, like that's

real. Those are real friendships and there's real trust that gets built there over time. But the funny thing is that they are not our direct customer. We still sell to the people who are on LinkedIn. Ultimately, the bigger companies, that's where the revenue operations and the sales leaders are. But it's because I spent time with them and understood the space. That was like a really... And I'm still in those WhatsApp groups. I mostly just use them like

for joking around. Yeah. Like, I don't, I don't be like, hey, everybody, we have a webinar we're doing next week. And we just like, I just like post memes and like give people a hard time and stuff. Yes. Yeah. Yeah. You know, like, just to be like, that's like my role in those communities. Yeah. You know, it's, we have, we have fun. We're having fun. And again, that hard to replicate that, to have that kind of rapport with people in the industry. Yeah.

So we should really paint a picture. So outbound sync, what does it do? What's the job it's doing for people? Yes. So the job to be done. So we get the data.

So we had this low-code thing. People were interested. I started having big calls with people. I realized this is not going to work. I'm manually OAuth-ing into accounts. Someone just asked me about SOC 2. We have a make scenario. I'm like, SOC 2? I don't know. Here's make security documentation. Yeah. We refactored into full code. We go to market. It takes four months to build it, two months to refactor it. October 2023, we go to market. And the job to be done is...

okay, if you... Well, I started with, if you're using SmartLead and you use HubSpot, we get your data from SmartLead into HubSpot. That was it. It was simple enough if you're using these two tools. But today, it's kind of inverted. I consider us a HubSpot app or a Salesforce app. If you're a team using HubSpot and you're doing outbound...

Well, then if you're using these tools, we can bring your data back into HubSpot. So fundamentally, we're a HubSpot app. We get this data in. And then as a HubSpot app or a Salesforce app, we get the data in. Job one. Job two is make the data useful. So I got a lead. Now I can route that lead to the right salesperson based on their territory or whatever the rules are. I can give them the context of that full thread of a conversation. Got it. I can see all the sent emails before that. So reply routing...

Because growth hackers were doing this in the beginning. So they would be like, to their founder-led customer, here's a Slack message. And the founder would be like, great, I'll jump on a call, done. But now, if it's like, we have mid-market customers with 1,500 employees, they need to route it to the right person. That rep needs context. They need to know what the campaign was. There's so many more rules that

are not possible the way it was being done before. Interesting. So routing the replies, that's like a huge pain point. So there's like a fire hose of leads. Yes. And then your app just says, okay, I've got to get these leads to the right people in the organization with the right context, with the right information. Exactly. Got it. And we empower the internal revenue operations or HubSpot or Salesforce admin to build the rules for that.

routing or the channeling the firehose. We allow them to build it themselves inside of HubSpot and Salesforce. Got it.

So I sort of finally came to grips with like, I'm not going to try to make people log into anything else. Yes. You went to where they already are. You want to be in HubSpot. I'm going to give you this data in HubSpot. You don't need to log in. You log into our application one time and then you're never ready to look at it again. Yeah. We build pipes. Got it. Like just use the sink. Don't worry about where the water's coming from. And does it show up in HubSpot and Salesforce as an official app? Yes. So we're in the marketplace in HubSpot and we're working on Salesforce. Yeah.

AppExchange, that's more of a process. But the biggest surprise learning I had in the beginning was that you actually don't need to be in the marketplace to get distribution through them. So when we talk about building a SaaS or starting a SaaS...

We had dozens and dozens of HubSpot customers before we had a marketplace listing. Okay. So it's because I was able to get HubSpot... I posted on LinkedIn and HubSpot users were like, we're using SmartLead. I want that in HubSpot. And they just reached out to me. Got it. And they would install it as a private connected app. So I was not using HubSpot as a direct distribution channel, if that makes sense. I was riding the HubSpot wave.

but HubSpot wasn't putting me on the board. Yeah. Do you know what I mean? So if you posted on LinkedIn and said, if you have this problem and you use HubSpot, here's a solution. And so people that were using HubSpot, it was enough for them to go, oh, I use HubSpot. And then go, oh, I have that problem. Exactly. Okay, now I'm going to pursue the solution. Exactly. Because they weren't even thinking to search for it in the marketplace because no HubSpot, so few HubSpot teams were even using these tools. Yeah. So there was no like search discovery motion. The place that at this time, like,

Even still, people are learning about these new cutting-edge things in Slack and on LinkedIn. There's no like, hey, we need to go buy a digital salesroom tool or we need to go buy a landing page tool. Go search in the HubSpot marketplace and see what's available. That wasn't a thing. Got it. There is for more established categories. Wow, this is interesting. So you launched this thing.

And you're primarily getting customers through LinkedIn and relationships? Well, initially, because I still have my agency, all the revenue came from my clients. And once again, I forced... I tried to bundle them. But this time it worked. Yeah. I said, listen, I run an agency. Yeah.

we specialize in helping teams that use HubSpot get new leads. And we have this tool to give you those leads. It's called Outbound Sync. And they're like, yeah, sure, we need leads. If you get in HubSpot, great. We want them there. We really want the leads, but we also do want them in HubSpot. And that was my first few customers. That was all my initial MRR, but it was because of that. And then when I started to get people come in and say, hey man, your agency looks great, but I just need the app. That's when I was like, I have a SaaS. Not like a software, I don't have a SaaS company,

But I have a SaaS because someone is paying me only for this Heroku app that I built with the developer. So that was the beginning of that. And so we were only selling direct for a while. So people would find us directly. And then eventually, I wound down my agency.

And then it was like all software revenue after that. Yeah. And you shared your graph with me. Yeah. It's pretty like, it's like 10, 15% a month, you'd say, in terms of growth. Let me see if I can share one. We're not like doing the build in public thing with numbers, but I can share my screen without the numbers. Sure, yeah. There's a little share button down there. You should be able to use that. Yeah. So this is like the transition. I've not talked about this with anybody anywhere yet. Nobody's asked. Yeah.

This is the journey from services revenue to software. So purple is my services or consulting revenue and green is my SaaS. This is gross top line money made. And so if you're just listening, I mean, it's pretty much a crossfade. I mean, you've got... You can describe it probably better than me. But yeah, I mean, this has been the journey. Yeah. On one hand, so starting in 2023, most of your revenue is consulting. And then you see around

around... Well, I guess this would be just at the end of 2023. You start to get software revenue. And then the software revenue just grows every single month. And then gradually, the consulting revenue... Not gradually, actually. It comes off... You can see the transition point where you're just like, Oh, it's time to switch to... Yeah. Yeah. We don't have to share the numbers, but you're doing well. You've done it.

Right? Thanks, man. Yeah, for sure. I feel like we're there. I mean, I'll tell you this transition point, May 2024. So friend of the pod, friend of so many people, Ruben, Gammez, when things were taking off,

I emailed Ruben and I was like, hey man, I think things are going pretty well. Tell me about TinySeed. I've got this agency. I have these expenses. We have childcare costs. I have a mortgage. We have two cars. My wife works in healthcare. She's got a great job and she's making money, but we just have a lot of combined income and I can't not make money. What if this keeps going well?

And then like a month later, I was like, oh my God, I need help. Like I'm having calls with people that are way better prospects than I've ever had before asking questions that I am not at all equipped to answer. And I don't have time to answer. Yeah. And the hardest thing that I don't think people, unless you've been in it, it's really hard to explain is,

If you have a multi-thousand dollar a month retainer client, and then you have a multi-hundred dollar a month SaaS client, how do you balance tasks between those two things? It's different. The math doesn't math. This pays my mortgage, but this one is valued at the top line. My services are valued at bottom line, like EBITDA or whatever, like how much profit they're generating. The software is valued on paper at the top line of how much the MRR is or ARR is. Yeah.

But like, but like, this isn't a lot of money and that is a lot of money. Um, but this is technically worth more. And then like, this is a little fix, but it's just a little bug. And this is like something where if I don't get back to them, they'll fire me right away. Yeah. And, and so like, it's literally, it's impossible to decide what to do at any given moment. Yeah. Um, because the comparison is it's, it's apples and oranges. Yeah. Yeah.

And so that was like the appeal. So I started kind of coming back into like, oh yeah, TinySeed. Oh yeah, there's a thing for this. And so we ended up throwing our hat in and getting into TinySeed. And I made the decision to shut down my agency, even though at the time, my SaaS revenue was 20% of what my services revenue was. I felt like the momentum was just sort of undeniable, but I couldn't

I needed a bridge. Yeah. I just, I couldn't get it to grow fast enough to pay my bills. And I didn't know what I was doing. I had never gotten this level of success before. And so I didn't know how to like,

The learning I had done in the beginning, it got me here. And then all of a sudden, I slammed into a ceiling of like, I don't know what to do. I don't even know who to ask for help. Yeah. I don't know what should I be prioritizing right now. And so for us, that was like a godsend of like, okay, this will allow me to bridge the gap. Yeah. And then hopefully it works. If it doesn't work, that's really stressful because I just shut down this thing that has been paying my bills since 2019. Yeah.

And has been my lifeline. And now I'm committing to this. I switched. I mean, this is like a little detail, but it was an LLC. So I was able to do owner draws and it was very tax advantaged. And now I'm switching to a C Corp where I can't pull money out of the business. And I can't do the... I don't have the flexibility that I had before. So all of a sudden it was like, this business has to work. And so it was a really... But it felt like, again, I didn't have a choice. It felt like this is so obviously a better choice that even though it's a hard one,

It's the right one. And so that turned out to be the case. I've never heard anyone describe using TinySeed as a bridge before. So you've got this clear momentum with the SaaS. It's growing month over month. But in order to transition from consulting to this new thing, you need something to bridge the gap. And it sounds like in your case, that was both...

money, but also just having more people in your court that could help you, could help strategize, could help make decisions. Both, definitely. Yeah. Did you use the money for hiring or was it just as runway for yourself? Yeah, all three. So I use it a little bit runway for myself.

I brought on CSM. I brought our engineer on full-time. What's a CSM? Oh, sorry. Customer Success Manager. Oh, okay. And then engineer on full-time. And then we also got SOC 2. Okay. Which was totally worth it. But just like upfront capital-intense things, capital-intensive things. The other thing that happened is at the tiny seed, when the founders all met up,

I had all of a sudden agencies started texting me and they're like, hey, dude, I heard you're winding down. I've always been curious about App on Sync. I actually have a client that needs this. Hmm.

And it was because I shut down my agency, I think they felt a lot more comfortable working with me. Yeah. And so I set up our partner program May when we joined TinySeed. And now it's like 80% of our business. 80% of like revenue leads? Oh, wow. Yeah. So now, like, so agencies who I've been friends with this whole time, and I've always been like sharing notes with them. Yeah. Now they have clients who come in and they say, listen, we're a 1500 employee company, series D company. We have money. Yeah. We have people.

Not the problem. We just need the best. We need someone who's willing to take chances and do really interesting things. And that's what agencies are for. Even Nike works with that agency, right? Famously. But they say, but we use Salesforce. And so we need this data. We need it in Salesforce. We need to be able to attribute it. And it needs to be compliant. And so that's what we solve. We solve all of those problems and we let these really brilliant...

growth hackers do their thing. And then we connect them to the people who have the willingness to pay and the desire to pay, but have rules that need to be followed. And so that has become this huge flywheel for us. And we're helping them grow. We're helping them move up market because they're getting bigger and better customers because they can tell these stories. I see. So this is not like a standard affiliate program. This is a partner's program where

where you are giving the partners leads? They bring them to us. We refer some. I've referred Anthropic, so that's a pretty good one. But we don't have a ton of leads. They bring them into us generally. But what we bring is we bring the tool and then we bring a lot of support. So we set up a Slack Connect channel with them and with their customer. And our CSM is in there. And so our customer success manager is in there. So if they have CRM questions, if they need to get in the weeds, we say, hey, we will help.

think through this with your customers so that you can do the thing that you're good at. You are not a Salesforce admin. Yes, got it. You understand how to sift through signals and how to get the right people. We'll make sure that it's a lead in Salesforce with the right fields populated, created at the right time, signed to the right person kind of thing. So for your partners, you are enabling a whole new category of business for them. Yes. And giving them a superpower where...

When they have a new client, they're like, oh, wow, I can use Outbound Sync for this. Outbound Sync is going to provide me with all the support

and the tooling to do this job that might be too big for them to do normally or whatever. Yeah, it's just hard. It's just, it is a software requirement. The only way to do this is with software. Yeah. The funny thing is that these people are like, they have their own like dev resources typically. They have tons of really sophisticated internal tooling. It's just like hard enough and enough of a headache

that there's enough of an opportunity for us to build something. Yeah, for them to outsource it to you. And they're happy to, by the way. I've had people tell me, like, dude, I've got a bunch of vendors where I'm spending a bunch of money. AppUnsync is the only one that I don't even feel like negotiating with you because I don't ever want to think about Salesforce. I mean, that's a great signal. I mean, that's the whole beauty about SaaS is you're basically socializing the cost of...

but also support across thousands of customers. Exactly. And so, you know, I'm looking at your pricing right now. It starts at $99 and it goes up from there. $249, $499, and then enterprise.com.

So that's a pretty good deal. For $4.99, you're getting email and Slack support. I think we go over the top with support. Yeah. I think if someone were to come in today, they would be like, you got to dial that back. Yeah. I mean, I think we go over the top with support at Transistor too. I've been a Transistor customer. I agree. And it was awesome. And I loved the experience. I think that's just like, again, it's one of those things where if the whole world is going to...

AI chatbots and support docs or poorly paid customer support people that aren't professionals, then what's one way to stand out? It's having unbelievable customer support. And it takes less people than... To support 36,000 users on Transistor, which is probably, I don't know, 8,000 paying accounts...

That's two full-time people to do that. So it's an investment, but it's less people than you might think to do that work. Well, and people remember, you know, and then you get better feedback. The AI support thing, I've had such negative experiences with that. And the thing is, because we have ears to the ground, we're able to ship better features. And it's, I don't know. Oh, yeah. That's the other thing is that

AI might answer people's questions and it might give you analytics on the most... But it can't see the subtext. It can't observe things. It can't make notes and say, Oh man, I can really dig in here and see what is causing... What's motivating this customer and then also what's causing their problem. And those are opportunities. And if your job as an entrepreneur or a founder...

is to correctly identify opportunities. That's your whole job. And it's like, what are the resources I use to do that? Well, part of it is these back channels, these WhatsApp groups and Slack channels and all that stuff. Part of it is me having an audience on LinkedIn and watching what's going on there. And a big part of it is observing real customers who

And instead of just answering their question and moving on, just taking a break and pause. Hey, let me dig into this with you a bit. Like, can we jump on a call and talk about that? Can I just ask you some more questions? Very few people are willing to ask one follow-up question. I think we need to be asking two or three or four follow-up questions. That's where you kind of really dig into things. And the AI just wants to move on.

Right. Resolved. Anything else? Yep. And our propensity as humans is to want to move on. But the founder's job is to say, let's slow this down.

Hey, tell me more about that. What's going on there? What are you using right now? Okay. And is there... You're paying for that? Okay. Is it working for you? What's working? What's not? That's the magic right there. Yeah. I mean, I totally... I mean, I totally agree. So yeah, I mean, for us, that's super important. And we...

We're in this funny spot where all the time people are like, why can't I just do this with Zapier? I think it's a really good bootstrap business opportunity. I don't think it's a venture-scale business, but TinySoup is willing to take a chance on it. And I needed that bridge.

And there's just no way I could have done otherwise. I mean, that was like a couple months where I was doing both was by far the hardest period of the last six years. By far. I mean, I remember I was on a call with a guy. He was in Poland. We were on a call at 3 a.m. He's like, dude, what time is it? I'm like, oh, it doesn't matter. Like, can you just tell me if this is working yet? Like, it was excruciatingly painful. Yeah.

You know, we went through some family medical stuff in between, which I don't really talk about publicly, but it was extraordinarily difficult. And we've subsequently had a second child. And so it's like life just is happening while all of this is happening too. But yeah, there's a lot of reasons why this is like a weirdly cool opportunity. We're sitting between a few things. A lot of reasons why people think like Zapier could do it or Make could do it or couldn't I just do that with ChatGPT?

But because we're listening to customers and we're finding these weird little problems, like I'm on a demo call and I show someone like, oh, and you can do this in Salesforce. They're like, oh, that's okay. That's it. But you wouldn't know unless we talked to 50 other Salesforce people. We built that one tiny little feature where it's not documented anywhere, but it's just how that part of Salesforce works.

And if you talk to someone who knows, then you know. And if you don't, then you won't build it. And being able to observe their reactions and everything. Yeah. So everything you're telling me, Harris, just reminds me of this article by Rob Snyder called How Loom Found Pole. And the idea is that

But you want, instead of pushing a solution all the time, you want where there's just natural pull. People are naturally being pulled towards your solution. And he has this pull hypothesis that I think is so great. It goes, what are we designing for? And number one criteria, there's a project on their to-do list.

Number two criteria, that is unavoidable right now. So there's a project on their to-do list and it's unavoidable. They need to deal with it. Number three, they consider a list of options to get it done. So, okay, we got a problem. We need to get it done now. Here's our list of options. We're going through this right now with Transistor because we're trying to find an HLS video streaming hosting solution. So we're going through a list of providers.

But they think their options have serious limitations. And I think we've all experienced this, right? Like, here's something. So this is a poll hypothesis. And they go through Loom's whole company story. And their first one was OpenTest.

Didn't work. Great hypothesis. Just like you had, I think, some really good early hypotheses. Didn't work. Then they go to the second one. Here's the second one. Open test is the product version two. That didn't work. Okay, now we're going to create a product called OpenVid. And they're getting closer and closer to

And then finally, they get to Loom, which is this very successful video recording and sharing tool, which was acquired by Jira for $975 million. And what I like about this story and your story, I see it mirrored in both, is that Rob asks the question, was that original hypothesis wrong?

Maybe not, because there's actually some other companies that release products exactly with that hypothesis, and it worked. So there's a mix of success factors, timing, and maybe the skill of the founder, or the connections, or the product approach, or whatever. Any given hypothesis can work, but all you can do as an entrepreneur is keep iterating and keep trying to find...

The thing that's going to work for you, work for your customers, work in your world. And yeah, it just seems like you went through this exact journey. Yeah. I mean, if you scroll up that thing, I mean, this totally mirrors. So like today, like I had like this week, we've been like recently we changed our pricing and since we changed our pricing in February,

We, me. I changed our pricing in late April after I went to MicroConf. Yeah. And I listened to Marcos Rivera. It's called Street Pricing. Yeah. I listened to his MicroConf talk literally five times and then plus all the other random stuff. Okay. And I think since then, conversations have been going even better. So it's like for us, who are we designing for? It's revenue teams using HubSpot and Salesforce. Yeah. So they typically have multiple salespeople,

And they're running this outbound motion. They need to connect. There's a project on their list. Literally, someone said, two people, both people, my sales calls this morning, both said, I have it on my list to figure out how to get these two things to talk to each other. It's unavoidable because they're spending... The agency is the secret sauce for us because when they're really serious, they hire an agency. And so we're spending a lot of money on this really good agency. So we need results and we need to attract...

what's happening. That's the like secret to why I think why it's working so well is because they're committed to the outcome versus internal teams like play around with outbound, but like varying results and it's, there's no urgency. Yeah. So it's like they're shipping campaigns next week. We've got to get everything connected or whatever. Um, they look at Zapier or make or anything or building in themselves or not

not integrating them is like always an option. And then ultimately some of those teams decide that AppOnSync is going to help them get the data the way they need it. Yeah. So, I mean, I don't know. I mean, maybe there's a way to like kind of forcibly shoehorn this into any story, but I do feel like as I go through this, it feels like we have a version of this today. And I think this is the point is that if you can't,

honestly and realistically and reasonably fill out this hypotheses worksheet, already that's a no-go. Now, the hypotheses worksheet does not mean you're automatically going to hit a home run. But

The way you just described it, there's just these key points. It's like, this is a project on their list that's unavoidable right now. How do we know that? They've hired an agency. They have put... They've invested time and money and resources. This is... And this is like everything in a business. Like...

John and I have been struggling with sales tax forever, if you've listened to this podcast. And it's been on our list forever. And then it reaches a boiling point where it's unavoidable. We've got to deal with this right now. We are going to invest real time, real money. How do we know? Well, it's become Justin's number one

priority. It's my number one project for the next two, three months. We are going to get this done. And in our case, we hired somebody, a contractor to help us. I was meeting with them every week. We're strategizing. We're trying to figure out what exactly do we need to do. We're booking meetings. That's how you know it's serious. And again, there's no guarantees. But

The stronger the signal is here, and the less you delude yourself. Like...

When there's real money being invested and you have that key observation like you had, which was, they've hired an agency. This is serious. Now, this has gone from nice to have or, yeah, that sounds good, or to, no, we're pushing. We're doing this. Exactly. Yeah, there's board-level metrics. We have customers who are like, the VP of marketing is like, I have a board meeting next week. I have a question about this up on Sync Data because...

Our internal admin is going to build a report for me for my board meeting kind of thing. And you can, in customer interviews and investigations, you can ask questions that will reveal this, which is, what are you doing about this problem right now? So you say it's on your list. You've got a project that's unavoidable, that you say is unavoidable. You say it's on your list. What are you actually doing to solve that? And...

If they're like, eh, not much. I haven't really looked for anything yet. What have you considered? Eh, not much. It's like, okay. Sure, it's on your list, but I don't see actual motion. The customer has to be in motion in a real serious way for it to work. This is like... I built that project with a college grad called Swagfan. It's like... Yeah. Making swag. Now...

I use it. It's great. But that is not a serious project on most people's list. And so it's, it's never going to have that same pull that something else would. There's, there's something way higher on most founders lists and most marketing people's lists. Then we got to get swag out right now to our fans and influencers and everything. Well, so the urgency thing, I mean, for sure, there's so much to that. Um,

Last thing on this, where I think it's super interesting, is the value goes both ways for the agencies, too. They want to be able to prove results. And so when we get the data into that important system, they can show the customers the value. So for them, it helps with retention, too. And it helps them get credit when there's conversion that they didn't directly drive.

So I email a company. Let's say you're doing the sales tax thing and I end up emailing Helen for some reason. And I'm like with Numeral. Numeral solves sales tax for SaaS companies. I email Helen. Helen's like, this isn't my thing, but I forward it to Justin. Then Justin goes to Numeral. His website signs up. The cold agency that emailed Helen...

And then the next day you signed up for numeral, like that's a conversion that they're normally never getting credit for. Yes. So like there's, we're so in the middle of lots of things, but, and so we're trying, I think we're in the middle of like trying to create win-wins across things and just solve annoying problems so that different people can talk. And like the swag fan thing is a funny example of like, yeah, like who, yeah, who's feeling that? Who's like, God, I really, I really need this swag. Exactly. Yeah. So there's, there's a lot of weird ways where, I don't know, ultimately, like, I'm not sure why this is working right now.

if you add it all up, I don't know. I just, I just, it feels like it's going really well. I don't know what's going to happen next. And I couldn't really, if I had to recreate it, I couldn't because I, because I couldn't really boil it down to like, okay, here's the three things or here's the five things. But this is the important piece. I want people to take away. This is a journey.

It's like you deciding as a founder, I'm going to do this. And at the beginning, you think it's going to be a one or two year project. Like I'm going to quit my job and I'm going to get this done in two years and I'm going to have a great business. And the truth is, this is a lifetime project. And you are on a journey of iterating and trying to get closer to your goal. And again...

Every at-bat you have, you got to be doing something, some fundamentals to give yourself a better shot. But you also have to go up to bat. You have to make some swings like you did. And then eventually, something will hit. And you won't know completely why. You'll have some ideas. As an outsider, I think I can see a lot of characteristics about why outbound sync worked.

It just has a lot of built-in momentum. You're in an existing juggernaut of an ecosystem with HubSpot and Salesforce. There's so much money in motion there. And so for you to capture some of that value or create new value inside that ecosystem, it just makes sense. And I think people need to follow this example and understand that

There's no guarantees. So you could get up to bat 10 times and it might not work out. But what you're doing as a founder is you're basically betting that if I keep at this, if I keep improving, if I keep learning, if I keep iterating, one of these at-bats is going to produce something that

And yeah, dude, I'm just so pleased for you. Congrats on getting it to here. This is such an awesome success story. Thanks, man. Yeah, I learned so much. I feel like I was learning so much for so long from you. So when we connected and talked about coming back on here, it felt like a really full circle thing. I was happy to do it. I feel like it's the end of the beginning now. And so now the work begins, but it feels like we're default alive.

I'm not like really anxious about paying bills or the threat of not being able to pay bills sort of somewhat soon. And so now I'm hoping I can breathe and start even taking some bigger risks than we have before. Because like the last six years, every time I placed a bet, it kind of had to pay off or I had to do or be such a little bet that it could lose. Oh, yeah. I mean, once you get out of that scrappy bets stage where like good investors, good people who make... People who are good at making bets...

Eventually, the whole idea is that they are betting resources that they can lose. Right. So it's like, this is a pretty good bet, but if I lose this bet, it's not the end of the world. Whereas when you're at the beginning and you're bootstrapping and you're scrappy, it's like...

if I lose this bet, yeah, like it could be rough, you know? And it felt like every bet leading up to Transistor was like that for me. It was like, okay, like...

I am betting the farm every time. That's why it's so hard. But yeah, now at this stage, I think you're about to enter a really fun stage. Running a company is always hard. But at this stage, when you have more resources and more breathing room and more calm and more margin, then it just becomes about showing up every day. I just think my job is showing up every day and moving this giant rock...

further down the path. I'm just pushing it a little bit more. And those efforts are kind of multiplied in a way that didn't happen before because there is existing pull. So...

Yeah, I'm excited for you. For folks who want to check out what you're doing, where should they find you? On LinkedIn and at the website? Yeah, outboundsync.com. And then yeah, LinkedIn, Harris Kenney, look me up. As we've been embracing our partners, I post really weird, funny stuff like...

about Pokemon and I've been posting memes and just like we found our ICP and so I'm just having fun like posting for them. Oh, sweet. So yeah. So if you like kind of funny, goofy LinkedIn, go there. If you're looking for inspiration, it's not the place. Sweet, sweet. Well, thanks so much for being here.

I'm going to read out our supporters because we haven't done our Patreon shout outs in a while. So thanks to everyone who's still supporting the show on Patreon. We've got Pascal. We've got Greg Park. We've got Mitchell Davis. We've got Marcel Follet. We've got Bill Kondo. We've got Ward from memberspace.com. Evander Sassy, Austin Loveless, Michael Sitberg, Colin Gray, and Dave Junta. Thanks, everybody. Thanks, Harris. See you soon.

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