¶ I did it! I build my saas!

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, cofounder of transistor.fm.

And I'm Harris Kenny, founder of OutboundSync.

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.
Like 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 I listened to the the show for years. And so and, yeah, I hadn't 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 we asked 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.

And so I just didn't have a lot of time. So I was like, hey. I wanna go, and I'm like, I hope I'll catch Justin. Take out the boots, but if I don't catch him so I just like it was like, well, 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 like, I was late and I had to leave early and I I hope I caught you, but it just didn't it was just too tight. But, like, there's a future with more margin where you're like, my friend's in town. I'm gonna go do this thing, and, like, I have time to do that. And I just, like, haven't haven't had that.

Yeah. I mean, I I think that's gonna resonate with a lot of people. As an aside, this is something I've been thinking about for a while is you're a part of this Mega Maker community that I've been running since 02/2013. 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 gonna try to do some, like, on both sides of the continent. And, yeah, hopefully, we can still hang out Yes. In person.

Definitely. I mean, assuming nothing tragic happens, but I mean, I mean, I'm here, and I would love to. And I so I joined Mega Maker, but then left. And I I had joined a bunch of things and left kind of, like, in the early days.
¶ Why did Harris quit his job?

Why'd you why did you leave? You just felt like it was too much. Not what was the reason?

So I left, like, everything. It's like I got off Twitter. I left MicroConf. I left Mega Maker. So 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 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 stressed or-

Just not like a lot of flexibility. It's like, you know, and like, well, what if I, like, need to go to an appointment? And the the boss said I'd had at the time was he'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

Yeah. 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 02/2008, I had a great boss. But even then, I remember there being some things that graded on me. 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. You know what?
Like, 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 so 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 wanna be in a position where I don't have to ask for permission to, you know, take some time off or whatever. Yeah. Well, do

you remember Shawshank Redemption? You ever see that movie? Mhmm. You just, like, reminds me of that. And, yeah, I mean, I I felt like it just felt arbitrary. I mean, I was in a role where I was at that in that 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 like I ended up putting it up like on GitHub or something. And then linked the GitHub thing from the support center because the support team wasn't willing to let me put it there. And it was like, why is this so hard? Yeah.
And it was like, hey, I want data about who we've sold to. And they were like, yeah, our system doesn't really like, it's in there, but there's no UI. So I, 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 a entrepreneur. I I think like 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, and 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 kind of old oppressive teams will they they they just kind of suffocate or suppress you or make it harder for you to contribute in a meaningful way.

That's how I felt. Yeah. Like, I think that, like, 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 like a few jobs at this point. Like, at at some point, maybe I'm the problem here, and, like, maybe I need to do the different thing. Because it's like nothing that they were doing there was, like, obviously on its face. Like, how could you? How dare you? You know? It it was just, like, it like, grading.
It just felt like suffocating. But it's like but it made sense. Like, yeah, this isn't the web team's problem. It's not that big of a deal. Like, sorry, it's not a priority. But anyway

Oh, yeah. I think this is the I think this is the realization is it's if you're a fast horse and you want to run, there's just some structures that aren't going to be work for you. And that's fine. Like, if if the boss or the team or the culture or the business model or the market just necessitates something else, like if you really want a remote job, but the company is really a on prem culture and, you know, you need to be there. Well, you're just not the right fit for that place.
And 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 like really be kind of in my zone of genius until I'm able to be doing this on my own. Like Yeah. Nothing will satisfy this itch until I'm in charge and I'm calling the shots and I'm it's all reliant on me,

but That's what I was that's 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 we had, like, had our first house. Yeah. We had our first mortgage, but that was like so I didn't need a a w two to get approved for the mortgage.

Yeah. A check. Yeah. Always get your get your mortgage before you quit your job.

Definitely. Because you can always drive Uber, but they're not gonna approve you if you're driving Uber. But, you know, there's like a difference between showing you make money and actually being able to make the money. Right? Yeah.
I was like, okay. We we had 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, more than happy to do, but 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. Mhmm. And I had built up a pretty good network from my previous jobs.
We I helped scale a three d printer company from 2014 to 2019. We'd gone from 1.7 to $20,000,000 in revenue as like a hardware It was really hard. But I learned a lot and I met a lot of people because it's a really high visibility thing. Mhmm. 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 I got I got my commitments basically. I incorporated on 04/01/2019. I got my commitments. I quit my job May 1.

And these were commitments for projects? Like, these were clients?

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?
¶ When you don't have a boss, do you have the drive to go get work?
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, had six months of work? Or

Let's do it. Like, signed, closed, contract signed. We're gonna start next week. So I was like, okay. I'll I'll work weird hours. I'll make this work until I can get to 50%. Got it. So So I waited till people, like, 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 is what my guess was. So I saw one contract. Basically, one contract was enough, but there 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 gonna unlock forty 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 June or by the 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 and 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? Like after I'd quit my job, there was times where, for example, course sales were like enough. And I was like, I got to go build some WordPress websites for people. And it's just this like dogged, relentless drive to say, I'm gonna do whatever it takes. I'm gonna email 100 people until I sell, you know, 10 website contracts and I'm going to build them all and then, you know, 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 gotta I gotta kinda 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 this is expensive.

This is just like Just keeps going up.

Yeah. And expensive in a sense, like, 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 gotta you've gotta get more space. You gotta get a car. You gotta get a car seat.

Yeah. Oh, yeah. Totally. Yeah. There's just hard hard cash flow hits that come with that.

Yeah. So so 2019, you you launched this, you get some clients. COVID hit in 2020. So Yeah. What what did that affect you at all or

what Yeah. Yeah. Yeah. Yeah. So terrible timing. Just couldn't have really couldn't have done it worse in a lot of ways.

What? Because it it affected it poorly? Was just so stressful

and that we were expecting at the time. So every time I got to the mean, in the beginning it was really unknown. Then especially because we were expecting during that time, it was really anxiety inducing. 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. Mhmm. 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. So that was like worth it for them. But I was like, what if I get sick and I can't take that call? Like, are you going 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 like I joined MegaMaker and I started listening to Build Your SaaS and Startups for the Rest of Us, I joined MicroConf.
¶ How did you hear about saas businesses?

Were you familiar with software as a service or web apps? Like, was that you came from like a a world where you're selling hardware?

Yeah. I was I didn't have software background. I mean, I had done like ERP consulting in 2013 as a as an account executive. I mean, so no. I mean, I mean, I'd never worked for a SaaS company at all. I 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 Walling's stuff first and that tipped me off in SaaS and then I found Build Your SaaS and Transistor.

Okay.

And then it just kind of like, was like, because what I wanted was like to take care of my family and to build good business. So then it's like, 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'd 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. Just like, I didn't it it's taken a long time to get here, but within this, there's been, like, really tight learning loops. And then it was like, oh, like, this is it. Like, I went out to work on my own because I want my own business because I wanna be present as a dad and brought my family. And, like, this is the best way to do it. It is a SaaS. I need to figure out how to have a SaaS somehow.

Mean, doesn't seem that long in my if you think about it, it's been six years.

So Yeah.

It it's been six five or six years since you even kind of realized what the SaaS market industry category, how it works. So that's pretty compressed.

Yeah. I mean, I guess in hindsight, yeah. Yeah. It feels like a long time. It feels like a long time.
But, I mean, once we once when once once the my actual idea hit, it was like it it took off really quickly. So it was a lot of tight, hard learning and then but but like having to maintain cash flow the whole time. There was no like, oh, I'm gonna 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 pull 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. I then you try consulting and you're like, okay, consulting works, but you have to keep this thing every sales cycle is you're starting from zero again. I mean, it's not really zero, but it's like it can feel like that.

Oh, no. Definitely. Yeah. Yeah. I mean, basically is. Unless you start developing IP and, you know.

Yeah. I mean, I guess the the reason I say it's not always from zero because you still have your network. Like, 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. And then there's the stress of that and like delivering projects on time and, you know, and like even like 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. And so then you search for, okay, what are some of other options? And you're like, oh, recurring revenue. Like, if I could just have, you know, instead of having to rebuild it every sales cycle every month or every quarter, I just every month, new stuff can come in. Mhmm. And then you go look for solutions, and it's like, oh, I I could build a SaaS business.

Mhmm. Exactly. So that's that's how I kinda land on it. But then I'm like, okay. I gotta learn about SaaS.
So I join all these things. And I'm, like, super active on Twitter at the time just, like, absorbing, absorbing, absorbing. Mhmm. And I feel like I was just in, like, just downloading, just constantly downloading little things and thinking about thinking about surfing and, you know, all these all these analogies and the stair step method and dah dah dah dah. But I think, like, in general, what I was feeling was like, Okay, this is like too much learning.
I need to be like doing now. I need to like start like 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 like a little bit more of an engine so I can free up, make more money or just free up a little bit more time? Mhmm.
So it kind of converted into a little bit more of an agency. Because at the time, like email deliverability started to started to become like a little bit of an issue discussed in some of these corners of the web. Most of my clients, they didn't they wanted to talk to me, but if they were really hard, like, and clear, they would say, well, I want leads. Yeah. Like, 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 a $100 on Twitter. And so I started learning cold email and started building an agency around outreach Yeah. As, an extension of this consulting service. And so then I started getting really deep in that into that world, and we became a HubSpot solutions partner.
We were doing outbound. And then then I like, the the landscape started to, like, sort of emerge of, okay. These are the tools I'm using. These are gaps between these tools. This is how they charge. Mhmm. This is, like, what's annoying. And then within that, I had had like a few different ideas. But 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 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 gotta go. And so I, like, I literally deleted Twitter. I literally left, like, everything.
I just started spending, like, all this time on LinkedIn and and and to to kind of like so that was kind of that, like, that, like, transition period in the beginning of what was, testing ideas.

This is so key. Like, there's a you're gonna 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 02/2012.
And, you know, after a year of doing these interviews, I felt like I gotta stop doing these interviews, and I've gotta do something. Like, I gotta launch something exactly the same as you. Like, this is until I start putting this into practice and really feeling it, it's just like anything. It's like 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, it the head knowledge is fine, like, 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. Exactly. You gotta land on your butt and be like, okay.

Yeah.

That was fine.

So that's I 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 it was kind of like a little sad because it was like, oh, like, is fun. Like, I like talking to these people. Like, this is funny. This is my community. I'm home alone. Yeah. I have no real coworkers. I like, all my friends have jobs, and then we have a young kid, and so I don't have a lot of time in general.
Like Mhmm. When I'm not working, I'm trying to be a dad as best I can and trying to be a husband. And so so it was like a little sad, honestly, but it but I just didn't feel like I had a like all of these things, 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. Mhmm. 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, like, is gonna 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. Mhmm. Mhmm. 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, but 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 Smart Lead. 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 as inbound. So they're constantly criticizing it. 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 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 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 generating new leads takes off, then new tools will be required to like coordinate or orchestrate the new tools with the old tools

Yeah.

If it if it takes off.

Okay. So let let a client is paying you to help them manage when you say outbound, you're talking about sending cold email

Yep.

Trying to get leads. Yep. And this client says, this is good. They weren't paying they weren't a high value customer, but they just said, this is good. I really want this like, 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. Like, you use content to attract leads. So there are inbound leads. They sign up on your blog posts because to get the PDF. Yeah. And then you manage the relationship that way. But not a lot of people using HubSpot were starting with outbound.
¶ Recognizing a need and building something for it

Mm-mm. No. No. Yeah. At least not publicly. But then I realized like, actually quite a few of our HubSpot clients are doing outbound. Yes. And actually HubSpot themselves has a huge sales team with like a few 100 salespeople and they totally do outbound.

Yeah. So this seems like a gap. Like, this is a opportunity.

Exactly.

So what did that translate into? What what did you do with that information?

Well, 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. Like, 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. I I I remember saying, like, how hard 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.

That's that's the entrepreneur's Yeah. Mantra. Yeah.

So that was it. The the the pinboard the pinboard guy said that, and I it's I think about it all. It's on LinkedIn. Think about it all the time. I remember literally being like, oh, yeah. Like, how are gonna be? And I said that to him. And so so this is May 2023. So Okay. Did we

miss a part here? Because you did try to build IntroCRM.

Oh, yes. So my agency was called IntroCRM. Yes. Sorry. I covered some of the I missed I skipped some of the SaaS stuff because because it was never a SaaS. Okay. I tried doing IntroCRM as a SaaS, and now and my agency just became IntroCRM, but we never I never had a single paying customer. I built something in Bubble. Oh, man. Sorry. I forgot about I haven't thought about that in, like, in, like, a while. No.

That's that's okay.

Yeah. Yeah. So oh, yeah. It was so bad. Don't even remember it. My first necessity was a CRM.

Yes. So you were doing this agency, and then you're like, okay. I'm gonna try to build some software.

Yes. Right.

And then you built this tool called InterCRM in Bubble, 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, man. Totally spaced on this chapter. Mm-mm. That's fine. I was using Basecamp, and I was like, oh, Basecamp, they're discontinuing Highrise. Like, there's no CRM like Basecamp, and they're not doing Highrise anymore. There should be a simple CRM for everybody that everybody can use.

Opportunity. And and, mean, Highrise 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 success 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 Heinemeier Hansen. And part of my idea of, like, going from agency to SaaS was, like, 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, like, self critical, I would say, well, they were really they were really running a design agency. They were really crafts people and, know Mhmm. What was I doing?
But I think I'm probably being a little hard on myself. I think like, I I was doing hard stuff, and it and it 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. You're it feels like unattainable of like but they're just normal guys too working hard and doing great things, but they're, you know, just people too.
In hindsight now, I feel like I created too much distance in my mind between what they were to do and what I what I would be able to do, you know, of like, oh, how could I ever

do that? They're just humans too. I mean, they're they are very gifted in 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 Yeah. 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. 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, they you know, I don't think you know, they just had to have a brand, they did it early, they've done it at an incredible scale. I think so so IntraCRM 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 we integrated with Trello and Basecamp and, oh gosh, I can't remember it now, but there was, like, 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. Mhmm. And I was like, oh, yeah. Like, 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, like, we have this basic CRM and it comes with these services. Okay. And they were like, we just we just wanna work with you. We don't we don't want your CRM.

Got it. So the so when you pitched people on it, they were like, like, we just want the services part. Why why do you think they didn't want the CRM? Like, what were they using instead?

They just, like, didn't check it, didn't log into it. I had, like, an amazing client, and she was just very kind. And I felt like if anyone, she would have just, like, logged in just out of, like, curiosity and sympathy

Yeah. Or pity.

And even she had never logged in. So I was like, okay. This is like, nobody cares about this, really.

I think what's interesting about this is your hypothesis seems reasonable.

Mhmm.

And so then, you know, there's different questions. Is it is it the way you're marketing it? Is the way you're positioning it? Is it the actual product isn't solid? So those folks that weren't logging in, what were they doing instead? Like, what were they using instead of your CRM? Were they just using no CRM? Like, they Yeah. There wasn't actually any movement there?

Yeah. They would like use nothing or they would use a Google Sheet or they would just kind of manage it out of their inbox. I think there's like a version of this, but I don't think I have founder market fit to build it. It has to be like a product led thing. 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, 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. Then when they got big enough, they hired somebody to do it. And then that person wanted a real tool, right?

Yeah, and then they would so you were in this kind of in between IntroCRM as a software product was like in an in between state and that was like not quite right.

Yeah. It just didn't quite land. But but I was right that people like, the the core idea of, like, these things don't talk to each other, that has, like, a thread that has been true for a while. And, like, even back to the three d printing company and even back to the ERP consulting company, like, partnerships has been, like, the thread of growth through, like, fifteen years of my career through the companies that I've grown. That is like a that is like a continuity thing.
Like, my idea of, like, these things don't talk to each other. That is now fundamentally what AppOnSync is built on today.
¶ So many opportunities in inventory software

I think that is such a crucial observation. 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. Like everybody's typing into ChatGPT and Claude, but there's still not a lot of glue between like, Claude could tell you to go do something, but then you've gotta there's this chasm that 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 there's going to be a lot of opportunity just in that. Even, you know, like Zapier integrations break all the time, or they're not quite right, or 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, I would ask owners about what they were doing and they're still entering inventory manually. Mhmm. And you'd think, oh, man, like there's a barcode on every product they get in And you'd think that or you'd think that the 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.
Like, the economics of all that of the opportunity might not be there, but the thread is correct. Yeah. And I think you've identified like, there's gonna still there's still so much manual data entry right now. There's there's lots of opportunities here if you're, like, looking.

I think so. Absolutely. And here's the thing. So someone would say, well, yeah, of course, you gotta enter this thing into Claude, then you gotta go to the other thing. Well, that's where MCP servers come in, and that's why agentic workflows are so exciting. Yeah. I mean, any developer, Hey, so tomorrow I'm going to publish our database schema. Nothing will be lost, no security issues. I'm just going to publish it and post it online. 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, no problem. Open Kimono. Let the world see.
And so if that's the case, if the developer who's building and maintaining a 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 like 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 Mhmm. I use this tool called Eulene audio meter or whatever. It it tells me the loudness in Loofs. But then I take a screenshot of that, bring it into Claude, 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 or may and the truth is, is it's still a lot of friction to get something from one system to another.
And for most users, that still exists and there's just a lot of opportunity there. Yes. Like, if there was a tool that, in my case, like maybe a web app or something, that, you know, automatically gave me a loudness score for my raw audio and then told me what, you know, what to do or just automatically did it for me, I might 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 I think that like with I mean, with AI, I mean, imagine if you had like a library, you know, like a physical library. Mhmm. But like no card catalog.
Yeah. It's like, okay, well, are you gonna find the book? And I mean, and at some point you're expending and this is the thing I think people aren't talking about. They say, this is the worst it's ever gonna be. It's always gonna get better.
Like, well, maybe. There's also like a lot of money being spent right now. And like, at some point, there's gonna need to be a return on these things. And at some point, they're gonna 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. Yeah. You know? And then you have like system collapse.
So it's just like, I like AI. We use it. I've I tried building a a GPT wrapper. So Yeah. Let's talk those other SaaS ideas. So Yeah. 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 ZoomInfo and Apollo. And so I'm giving them Google Sheets. And so I was like, oh, this is a SaaS. It's a lead rater. Built it with Glide. I give you like a sample set of leads. You can swipe through it like a dating app. Yeah. 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 it wasn't, like, wasn't, like, the worst. You know? I mean, it I mean, it's it's kinda like an LLM concept. Right? It's like reinforcement training

from

the person who knows. It took a lot of work, and, again, like, they they weren't spending the time on it. I I don't know. It just for whatever reason, it didn't quite click. People didn't wanna do it or or they were just getting too lost in the weeds. Mhmm. And I was like, yeah. Like, I understand what you're saying, but we just need to send some email. And if if it's not a fit, they just won't get back to us. It's okay.
¶ The difficulty of getting people to just log in
Yeah. Doesn't have to be perfect. So I don't know. It just, didn't work.

You know that oh, that's such an interesting the 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. I think this happens a lot more than we realize, which is there's just a certain category of applications where you're not gonna get people to log in, and that's difficult. It's like it's like I'll I'll 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.

Mhmm.

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 that because there's just only so many apps I can log into regularly. Right. And even like like, oh, I've got these analytics. Like, you're gonna log in and get these analytics. It's like, well, the only apps I really do that for is like revenue analytics because money is important. And then kind of performance based metrics on content. Like Yeah. You know, blog, you know, website analytics and podcast analytics and YouTube analytics. I'll look at all of those.
But 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 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. That I I only have so many spaces in my life for things that I log into.

Exactly.

Yeah. That's interesting.

So it just, like, it didn't it didn't quite click. It was so then the the third idea that I had was draft studio. This was like an early g GPT wrapper product. I actually use 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 like 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 it's just like made some of these things less necessary now, people are making fully unique emails every time. Mhmm. So it's just like I just kinda 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 it was just a as a GBC rapper, it was too simple to really go anywhere, and I kinda 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 Claude, I would just do that. Totally.

Yeah. Yeah. So like that but it was okay. But it was technically a SaaS. I built it in Glide. I thought about charging for it. And then and then so so that all of those things happened between, like, 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 I think it was my fourth idea. My fifth idea, which I've, like, almost not really talked about very much, but it was card importer. There was, like, the HubSpot's default card importer is actually really not great.

Okay.

And so it was, like, a really basic take a picture of your business card, scans it in HubSpot. It's actually a really big like, it's a thing. There's a lot of HubSpot comments and a forum about wanting these features. I posted a YouTube video. I still get messages on LinkedIn about it.
People being like, hey. Is Cardimporter, like, still available? Yeah. So I actually think it like, there's something, but it's not a it was my fifth idea. Nap on Sing was taken off, so I just didn't do anything with it. Mhmm. But of of the ideas, it was probably my second best idea, but it would need more around it to, like, become something. Yeah. But I guess my point is, like, 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 talking 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 is like, 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 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 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. Like, those are all opportunities. Those are all sorry. You know, potential outcomes.

Mhmm.

But it's still it's like a lot of players get up to bat and they strike out.

Right.

And they're good players.

But what's the number? It's like if you bat 300, you're in the hall of fame or what you know, there's something like that.

Yeah. I mean, I I'm actually not a baseball fan.

Yeah. I'm not 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 kind of thing.

I mean, this is the 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. Business has there's more opportunities. Like, there can be multiple CRM software providers, and, you know, you could still win.
Totally. So I 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 there's 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 getting, like 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, you know, 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. Definitely. You do the basic find the basic foundational work to give yourself a chance. And then that's after that, it's like, we'll see what happens. You know? Yeah. Hit this one. Okay. It was, you know, I barely got on base.
¶ The saas that worked

Yeah. Well, it's like the harder I work, the luckier I get. Right? It's like, I definitely think this was like a lot of a lot of work. But but so because of all this, when outbound synced, like, when I did that and I started talking about it to people, I was

like Sync is your is the idea that you're working on right now.

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 we since October 2023. Like it like and but there were there were things that were happening with it where I was like, this has never happened before.

Okay. Okay. What's different. Let let's explore that. So you you went through these other ideas. 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 by

domain. Yeah. Maybe by domain. Yeah. Maybe by domain. So what was the genesis of outbound sync? What like, what was the observation that you're like, oh, some this is worth doing?

So, you know, 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 like the people who if I'm gonna build something based on the space that I'm in, they're gonna be there. Yeah. Probably. So I start posting about it there. I post 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. I don't

know why.

It's very international. Like, very there are some biases, but in general, it's pretty meritocratic. I've got a lot of people who I talk with who are like, 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 anonymous like hacker chat kind of 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, like, other agency owners are in some of those groups.

Okay. And they'd say, hey. You might wanna join this group.

Yeah. Hey. Oh, yeah. Exactly. And, like, one of them, like, they had, like, a just, like, they were promoting it to, like, hey. Join my group. And there's no caution in it that I just kind of joined the group. Share best practices. There's kind of like a guild. You know, there's, like it's kind of like there's honor among thieves.
Mhmm. The, like, the best outbound people, like, all know each other, and they all talk. And they all share notes and and they don't consider themselves as really direct competitors in a in a traditional way. Yeah. Like, it's 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 gonna go where my clients are. So LinkedIn is a natural choice. 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, is 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. You're doing that, like, I think it's pretty hard. 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 to conceptualize a show, and then record into a shitty mic, and then, you know, try to publish it and then be listening to it and hearing background noise and like cringing. 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. Like, do I really understand that category as an outsider? No. And so if I try to swoop in and and say, I'm gonna compete with Harris, Justin Jackson tomorrow. I'm just gonna start a new app.
I you have such an advantage over me. Even with ChatGPT, I could get all the like intellectual information. Like, tell me about the outbound world and it might be able to, you know, even pull in stuff from Reddit and stuff and get 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. Like, nothing compares to being in it. And I 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 gotta 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, like, the two parts of the business. Mhmm. I'll I'll we we can cut we'll keep we'll keep riffing, but, like, 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 with the details, but, like, I've done personal gestures for them just because, like Mhmm. I love them. I just like I love them. And if they if they if some like, truly, I consider them, like, comrades. Like 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, whatever. 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. Like, I mean, I mostly I just use them, like, for joking around. Yeah. Like, I don't be like, hey, everybody, we have a webinar we're doing next week. 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. We have fun. We're having fun.

And again, hard to replicate that, to have that kind of rapport with people in the industry. So we should really paint a picture. So outbound sync, what does it do? Like, what was what's the 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 are interested. I started having big calls with people. I realized this is not gonna work. Like, I'm manually OAuth ing into accounts. People someone just asked me about SOC two. We have a make scenario. I'm like, SOC two? I don't know. Here's makes security documentation. Yeah. We refactored into full code.
We go to market. Takes four months to build it, two months to refactor it. October 2023, we go to market. And the like, the job to be done is, okay, if you well, I started with if you're using SmartLead Yeah. And you use HubSpot, we get your data from SmartLead into HubSpot. Okay. That was like that was it. It was like simple enough if you're using these two tools. But today, if you it's kind of inverted. I would I consider us a HubSpot app or a Salesforce app.
If you're a 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. Like 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 like I got a lead. Now I can route that lead to the right salesperson based on their territory or whatever the rules are.

Okay.

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 like reply routing. Because like 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 like so many more rules that are not possible the way it was being done before. Interesting. Routing the replies, that's like a huge pain point for the sales So this is 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 Yep. With the right context, with the right information.

Exactly.

Got it.

And we empower the internal revenue op revenue operations or HubSpot or Salesforce admin to build the rules for that routing or the like channeling the Firehose. We allow them to build it themselves inside of HubSpot and Salesforce.

Got it.

So I, like, sort of finally came to grips with, I'm gonna not gonna try to make people log in to anything

Yes. You went to where they already are.

Yeah. You wanna be in HubSpot. I'm gonna give you this data in HubSpot. You don't need to log in. You would log in to our application one time, and then you're never able to look at it again. Yeah. We 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 we're in the marketplace in HubSpot and we're working on Salesforce app exchange. That's like 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 Smart Lead, I want that in HubSpot. And they just reach 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. Do you know what I mean?

So if you posted on LinkedIn and said, you know, 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 gonna 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 sales room tool or we need to go buy a landing page tool, go search in the HubSpot marketplace and see what's available. Like that wasn't a thing.

Got it.

You know?

Got it.

For more like there is for more established categories.
¶ Where are you getting new customers from?

So wow. This is interesting. So so you launched this thing and you're primarily getting customers through LinkedIn and relationships? Is that

Well, initially, because I still have my agency, all the revenue came from my clients. And once again, I I forced tried to bundle them, but this time it worked. Yeah. I said, listen. I run an agency. We specialize in helping teams that use HubSpot get new leads, and we have this tool to get give you those leads. It's called outbound sync. And they're like, yeah, sure. We need leads. If you get in HubSpot, great.
That's 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 because of that. And then when I started to get people come in and say, hey, man, your agent looks great, but like, I just see the app.
That's when I was like, I have a SaaS. Like, 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 we built, you know, that I built with the developer. So that was like the beginning of of 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 it it's pretty like it's like 15% a month, you'd say, in terms of growth. Let me

see if I can 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, 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. 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, you know, money made. And so if you're just listening, I mean, it's pretty much a cross fade. I mean, you've got you can describe it probably better than me, but, yeah, I mean, this is kind of this has been the journey.

Yeah. On one hand, so starting in 2023, most of your revenue is consulting. And then you see 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 well, not gradually, actually, it comes off, you know, you can see the transition point where you're just like, oh, it's time to switch to yeah.
We don't have to share the numbers, but, like, you're doing well. Like, this is you've done it. Right?

Thanks, man. Yeah. For sure. I I feel like we're 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 Mhmm. Gomes. When things were taking off, I I emailed Ruben and I was like, hey, I think things are going pretty well. Like, tell me about TinySeed. Like, I've got this agency. I have these expenses. Like, we have childcare costs. I have a mortgage. We have two cars. Like, my I mean, my wife works in health care.
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. Yeah. 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.
And the hardest thing that I don't think people, unless you've been in it, it's really hard to explain, is that, like, if you have a multi thousand dollar a month retainer client, and then you have, like, a multi $100 a month SaaS client

Mhmm.

How do you balance tasks between those two things? Like, it's different. The math does math. Like Mhmm. One, this this pays my mortgage, but this one is is valued at the top line. The other know, my services are valued at bottom line, like, EBITDA or whatever, like, how much profit they're generating. The software is 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, that is a lot of money, 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 Mhmm. At any given moment. Yeah. Because the comparison is it's it's apples and oranges. Yeah. And so that was like the appeal.
So so I kinda so I kinda started kinda coming back into like, oh, yeah. TinySeed. Oh yeah, like 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.

Yeah. I

felt like the momentum was just like 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 like 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 I don't know, like, what should I be prioritizing right now? And so for us, like, that was like a godsend of like, okay, this will allow me to bridge the gap. Yeah. And and then hopefully it works. If it doesn't work, that's really stressful because I just shut down this thing that that has been paying my bills since 2019 and has been my, like, 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, 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, like, I I can't do the I don't have the flexibility that I had before.
So all of a sudden, was like, this business has to work. And so it was a really but it felt like, again, like I didn't have a choice. Like, it felt like this is so obviously a better choice that even though it's a hard one, it's the right one. And and so that turned out to be the case,
¶ Using Tinyseed as a bridge

think. I've never heard anyone describe using TinySeed as a bridge before. So you've got this, like, 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 in 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? Like or was it just as runway for yourself?

Yeah. All all three. So I use it a little bit runway for myself. I brought on CSM. I brought brought our engineer on full time.

What's a CSM?

Oh, sorry. Customer Success Success Manager.

Oh, okay.

And then engineer on full time. And then we also got SOC two. Which was totally worth it. But just like upfront 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, heard you're winding down. I've always been curious about outbound sync.
I actually have a client that needs this. 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 Tiny Seed, 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 1,500 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 like that's what agencies are for.
Yeah. Even like Nike works at agencies, right? Famously. So they 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 a a standard, like, affiliate program. This is Mm-mm. A program a partner's program where you are giving the partner's leads.

They bring them to us. We refer some. I've inferred I I I referred Anthropic, so that's a pretty good one.

Oh,

yeah. 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 customer so that you can do the thing that you're good at. You are not a Salesforce admin.

Yes. Got it.

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 Yeah. Assigned 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 when they have a new client, they can they're like, oh, wow. I can use outbound sync for this. Outbound sync is gonna provide me with all the support and the tooling to do this job that might be too big for them to do normally or or whatever.

Yeah. It's just hard. It's just it's just it is a software required. The only way to do this is 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 that I that there's enough of an opportunity for us to build

Yeah. To to for you to for them to outsource it to you.

And they're happy to, by the way. Like, I've had people tell me, like, dude, I'm spending I've got a bunch of vendors who are spending a bunch money. App on Sync is the only one that I'm not even I don't even feel like negotiating with you because I don't ever wanna think about Salesforce.

I mean, that's a great signal. Yeah. I mean, that's the whole beauty about SaaS is you're basically socializing the cost of software, but also support across thousands of customers. Exactly. And so, you know, I'm looking at your pricing right now.
¶ Going over the top on support is a key
It starts at $99 and it goes up from there. $2.49, $4.99, and then enterprise. 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 if I you know, if someone were to come in today, they would be like, you gotta dial that back.

Yeah. I I I mean, I think we go over the top with support at Transistor too.

I been a Transistor customer. I agree. And it was awesome. And I, like, 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 and or, you know, poorly paid customer support people that aren't professionals, then what's one way to stand out? It's it's having unbelievable customer support. And it takes less people than, you know, 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, like, because we have ears to the ground, like, we're able to ship better features. Mhmm. And it's I don't know.

Oh, To me, it's That's the other thing is that, you know, AI might answer people's questions, and then it might give you analytics on the most you know? But it can't see the subtext. It can't observe things. It can't make notes and say, oh, man. Like, 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, like that's your whole job. And it's like, what are the resources I used 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. 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, you know, AI just wants to move on.

Right. Resolved. Anything else?

Yep. And our propensity as humans is to wanna move on. But the founder's job is to say, let's slow this down. Hey. Tell me more about that. Like, what's going on there? What are you using right now? Okay. And is there like, 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 yeah. We're we're in this funny spot where, like, all the time people are like, why can't I just do this with Zapier? I think it's like a really good bootstrap business opportunity.
I don't I don't think it's a venture scale business, but it's like TinySteep is willing to take a chance on it. And like, we I needed that bridge and there's just no way I could have done otherwise. I mean, that those like, couple months where I was doing both was by far the hardest period of the last six years. Yeah. By far. I I remember I was on a call with a guy, he was in Poland. We were on a call at three a. M.

Yeah.

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?

Yeah.

Like, it was was excruciatingly painful. 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 like 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 lot of reasons why this is a weirdly cool opportunity. We're sitting between a few things. There's lot of reasons why people think Zapr 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, I'm on a demo call and I show someone like, oh, you can do this in Salesforce. They're like, oh, that's 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 like 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'll then you

won't build it. And being able to observe those 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 Pull. And the idea is that you want instead of like 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're 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 Yeah. 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 talk 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 hypothesis hypotheses. Didn't work. Then they go to the second one. Here's the second one. OpenTest is the product version two. That didn't work. Okay. Now we're gonna create a product called OpenVid, and they're getting closer and closer. And then finally, they get to Loom, which is, you know, this very successful video recording and sharing tool, which was acquired by Jira for 975,000,000.
And what I like about this story and your story, I see it mirrored in both, is that Rob asks the question, like, 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, you know, timing, and maybe the skill of the founder or these connections or the product approach or whatever. Any given hypotheses 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. Multiple If

you if you scroll up that thing, I mean, this totally mirrors. So like today, like I had a like, this week, we've been like, recently, we changed our pricing and since we changed our pricing in we me. I changed our pricing in, like, late April after I went to MicroConf. Yeah. And I listened to Marcos Rivera. It's called like street pricing. Yeah. I I listened to his microconf talk literally five times and then plus all the other random stuff.

Okay.

And we and I think we've really since since then, conversations have been going even even better. So it's like for us, like who are we designing for? It's revenue teams using HubSpot and Salesforce. Yeah. So they typically have multiple salespeople, and and they're running this, like, outbound motion.
They need to connect. There's a project on their list. Literally, someone said two people both people my 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. Yeah. 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 there's like, 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.
They look at Zapier or Make or any of that or building it themselves or not not integrating them is, like, always an option. And then ultimately, some of those teams decide that outbound sync is gonna help them get the data the way they need it. Yeah. So, I mean, I 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, I can 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 gonna get this done. And in our case, we hired somebody, a contractor to help us just like 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. Like, 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. Like, now this has gone from nice to have or yeah, that sounds good or to no, we we're pushing. We're doing this.

Exactly. Yeah. There's board level metrics. Like, have customers who are like the VP of marketing is like, I have a board meeting next week. Mhmm. I have a question about this app on sync data because our internal admin is gonna 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, not much. I haven't really looked for anything yet. Like, what have you considered? Not much. It's like, okay. This isn't yes. Sure. It's on your list, but

Yeah.

I don't see actual motion. Like, the customer has to be in motion in a real serious way for it to work. This is like, I built that that project with a college grad called Swag Fan. It's like Yeah. 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 gonna 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 than we gotta get swag out right now to our fans and influencers and everything.
¶ Showing results helps agencies show value

Well, so the urgency thing, I mean, for sure. There's so much to that. Last thing on this where I think it's super interesting is like the value goes both ways for the agencies too. They want to be able to prove results. Yeah. And so when we get the data into that important system, they can show the customers the value. Mhmm. So for them, it helps with retention too. Yeah. And it helps them get credit when there's conversion that they didn't directly drive.
So I email a company. I let's say let's say you're doing the sales tax thing and I end up emailing, like, Helen for some reason, and I'm, with Numeral. Numeral solves sales tax for SaaS companies. I email Helen. Helen's like, oh, this isn't my thing, but I forward it to Justin.
Then Justin goes to Numeral's website, signs up. The cold agency email that the cold agency that email Helen that and then the next day, you signed up for Numeral, like, that's a conversion that they're normally not never getting credit for. Yes. So, like, there's we're so in the middle of lots of things, but and so we're I think we're 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 it feels like it's going really well. I don't know what's gonna happen next.
And I couldn't really if I had to recreate it, I couldn't. Mhmm. 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 gonna be a one or two year project. Like, I'm gonna I'm gonna quit my job, and I'm gonna get this done in two years, and I'm gonna have a great business.
And the truth is 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 get 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 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 gonna produce something.
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 I mean, yeah, I learned so much. I I mean, I feel like I was learning so much for so long from you. So when we connected and talking about coming back on here, felt like a really yeah. Like a full circle thing. I was happy to do it. You know? We like, yeah. Like, feel like it's the end of the beginning now.
And so now, like, the work begins, but it feels like we're default alive. I'm not, like, really anxious about paying bills or the 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 in the last six years, every time I place a bet, it kinda had to pay off or I had to do or 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?

Yeah.

And it felt like every bet leading up to Transistor was like that for me. It was like Yeah. Okay. Like, this is I am kinda betting the farm every time. That's why it's so hard.
But, yeah, now at this stage, I think you're 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. Like, 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 wanna 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 Kenny. 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 so yeah. So if you if you like kind of funny goofy LinkedIn, go there. If you're looking for inspiration, it's you're it's not the place.

Sweet. Sweet. Well, thanks so much for being here. I'm gonna 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 Folle. We've got Bill Condo. We've got Ward from memberspace.com. Evander Sassy, Austin Loveless, Michael Sidberg, Colin Gray, and Dave Junta. Thanks, everybody. Thanks, Harris. See you soon.