Why George Hartley Built Nitrosend Without a Dashboard

TRANSCRIPT SUMMARY:

00:00 The Hundred Billion Agent Market
01:29 Building a Game With AI
05:15 The Drive to Keep Creating
08:05 Turning Rejection Into Opportunity
12:46 Building Australia’s Largest Art Marketplace
16:55 Launching SmarterMail
19:01 Selling the SaaS Company
25:07 The Birth of NitroSend
29:58 Finding the Ideal Customers
32:51 Lessons From Previous Startups
44:13 Preparing for an Agentic Future
53:22 Practical Advice for Founders

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FULL TRANSCRIPT

George Hartley (00:00)

Actually the TAM isn't half the internet, it's it's a hundred billion agents. And they're doing NitroSend, which is agent first. Actually, it can hurt when an opportunity comes to spend and grow. I'm still striking out two-thirds of the time, right? I can build whatever I want. This is the world's my oyster.

Jeff Holman (00:16)

Welcome back, everybody, to the Breakout CEO podcast. I'm your host, Jeff Holman, with Intellectual Strategies. We're a law firm that works with a bunch of startups and CEOs building things, and we don't get to tell their confidential information to you. So we bring cool guests onto the show who've also built their own startups and are often building second and third startups along the way and they're sharing their experiences so that other peer CEOs can can hear some of the insights and experiences that they've had and maybe.

learn some things to do in their own journeys. So today we've got George Hartley with us. George, welcome to the show.

George Hartley (00:50)

Thanks, Jeff. Good to be here.

Jeff Holman (00:52)

Yeah, it's great to have you. we just did our icebreaker segment and you're telling me that you you built a Tamagotchi Tam is it Tamagotchi or Tamaguchi? I I don't know.

George Hartley (01:02)

Yeah.

Jeff Holman (01:03)

Okay, Tamagotchi. You're building a Tamagotchi thing with Raspberry Pi and I'm like, I have an engineering background but but I shifted pretty pretty early on into law and got a business degree at some other stuff. And I I'm always jealous of people who have those hard engineering skills.

Which I don't know if that I don't know if that's hard skills to you, but to it's like I don't I either don't have the skills or the patience to sit down and do that stuff, I think.

George Hartley (01:29)

It's funny, it's it's like I was saying, it's I I I didn't I didn't look at a line of code. I I threw it to Codex. I said, I've got this new Raspberry Pi with a screen and I wanna build a little game for my two kids. give me some ideas and so, you know, went through a few things that would work and said, you know, a Tamagotchi style thing would be, you know, with some chores

chore type games in there and you earn coins and then as you do your little chores and you know, you can s swap that for prizes. And I'm like, Yeah, let's do that. And so it was that was it. And then I'm like, give me a spec. So I got the spec. I throw it at Claude. plugged it in and it built overnight. And the only direction I had to give it was this morning the graphics sucks. So I said, okay, let's

I just threw at a couple of examples of like nineties Playboy Pixel art and said, you know, just make it nineties Playboy Pixel art and a picture or two of my kids and make sure it looks like them and you did one one loop through and the whole thing works and is built. They were playing it this morning. It was great.

Jeff Holman (02:34)

That's so awesome. I I love it. I I I I I wonder how, you know, 'cause I'm talking with CEOs who are building stuff and we've seen this this evolution from, you know, building the hard way, you know, building the long way, building the expensive way to building with AI. And and now as we talk about even the next generation, you know, your your it was a Hugo and Stella, I think were your kids. you know, what are they gonna be building in twenty years from now? Like I'm just I I can't I can't even imagine.

how interesting it's gonna be when they get to that point. So what a what a benefit they've got.

George Hartley (03:07)

Something happened on the weekend and like this is you know, this is a podcast, so this will be old news. But it's still blowing my mind. I like I can't stop thinking about it. The the new GPT model, GPT six Astra, which is, you know, in in not not for wider release yet, they threw that at a bunch of quantum physics and maths problems that have never been solved, and it's solved ten on the weekend.

And these are problems that would like they're saying would win, you know, a Fields Medal or, you know, a almost no b Nobel Prize level sort of discovery or or or or kind of solve. It did tend. And and the the switch from the these models are really smart people to okay, these are way smarter than human beings. Yeah it feels like that could actually that could happen.

you know, in weeks in when this is released. And it's like, okay, then what happens? So are they are they doing maths? Are they building are they building things that we can't even understand, that they just work? Yeah, it's it's really like it it's it's so hard to know what the future looks like when you're like things can can be built that we don't understand the physics behind.

So yeah, it's it's a crazy time. It's it's awesome time to be building stuff, but it's also like I'm I what is what is twenty thirty one gonna look like, you know?

Jeff Holman (04:44)

Yeah, five years from now, that's totally different world. Ha with with that in mind, how fast stuff is moving, yeah, what is it that that drives you 'cause you've had you've had I think you said Blue Thumb and and then Smarter Mail and now you're building Nitrosen. Like as you build these and you and you kind of put it in the context of how fast technology is moving, what do you think it is that drives you personally to

To want to build the next thing.

George Hartley (05:15)

I just my favorite thing to do is to kind of create something from scratch in the world that I think is cool. Like that that is and it's probably a pretty n like I I think that's pr pretty universal, but f for me my whole life I've done stuff like that. Like I I think about I actually I played music.

my whole childhood and then throughout university I was still playing in bands and then I got a job and I didn't like that and I actually went and was a musician like just for years doing well that's all I did produce music and played in bands and stuff because it felt like I was creating something interesting that I thought you know should be in the world and it you know, it was a real putting putting putting something out that that was I was proud of that I thought was good. Like

from from zero and that's actually what drives me. and I had this point in my mid twenties where my music career was just wasn't going that well and I was you know I I was alright Yeah.

Jeff Holman (06:29)

Yeah.

George Hartley (06:31)

It may it may have been a talent problem too, but like I was okay at producing music and but it just it just wasn't yeah, I just I wasn't quite you know, I wasn't a rock star or I wasn't quite where I wanted and and I I was just

you know, I was sort of in this place and I'm like, what else? What I I didn't know what else I wanted to do that I was good at that I could give back to the world and and then I actually I I'd gotten an iPhone and I think the book's behind me and I was at the time I was also reading the jobs biography

Jeff Holman (07:03)

Okay.

George Hartley (07:04)

and I was like, hang on, like I used to like making websites and like I used to make it for friends and and bands and stuff and I I like that stuff. Like I I like to

you know, building technology stuff just as a hobby. And I'm like, shit, maybe, maybe I would like doing that as well. And that was I was about 25 or six. So I'm like, So I went back and I I sort of quit everything and I went back to study computer science. And I actually I found my rejection letter from RMIT.

Jeff Holman (07:33)

yeah.

George Hartley (07:34)

I because I I have a terrible memory. I've got a memory like a goldfish. I can't remember anything that happens to me unless I write it down. And I found it the other day when I'm moving house

I was I was rejected for my for my computer science thing and I then I remembered I actually went in and I'd sort of just convinced the the you know, the assistant dean that I would be able to you know, it was a master's, so you meant to be able program and I I would be able to do it, don't you know, like I I've done the

Jeff Holman (08:00)

Wait,

so you got rejected first but this is the same place where you ended up going 'cause you just talked your way into it?

George Hartley (08:05)

Yeah, yeah. And I talk about Masters. I got a Masters with Distinction the end. I actually got it did all right. And Blue Thumb, I built the first version of the app in in the Masters and that was, you know, featured by Apple and it set us off on this path. And but I yeah, but I I guess that's the other part of me is I sort of I I I am persistent. I think I sort of I tend to yeah, I do tend to work at things even when there's slog.

But yeah, like it was, you know, it was it was a big turning point in my life going to s to to do to switch into into building software. and I was really inspired by, you know, I loved Apple as a brand, but I was just inspired by that story and like the iPhone I fell in love with. And I'm like, I want to make apps, I wanna I wanna make great software. And, you know, I I started doing it and I I absolutely adored it. And I'm like, well, I want to do this forever, you know. I wanna do this till I die. So and I still feel that way. I like I get up every morning.

Even you know, it's it's hard. It's hard doing start ups and sure you always have problems, but I still feel like the day after leaving high school when I woke up and I knew I could do anything I bloody wanted. I have that feeling still because I wake up and I'm like, I can build whatever I want. This is the world's my oyster. So yeah. I love it. Yeah. I lo I love that about about what I do.

Jeff Holman (09:27)

I love that. Do you think your band experience that played into kind of your ability your your thought process to say, hey, a rejection letter is not a rejection. That's just like an invitation to go talk to the people and go like where did that come from? Because when I was in when I was in engineering school, I took a few business classes, you know, on the other end of the campus, right? And in engineering, it's, you know, prove the theor, you know, prove the theorems or write down the derivations and come to there's an answer and and you get partial credit for.

the work you do that's correct towards the answer. When I went over to the business the the the business side of campus and I was at some classes, it was I I couldn't believe they like students were arguing with the teacher about why they should get points for questions that from my perspective, they clearly got wrong. And the teacher eventually would be like, well, yeah, I think you're right. Here's some points. And I'm like, wait a second. This like blew my mind. And I I like, so if I got a rejection letter at that point in time in my life, I would have said,

Well, it's a rejection. Like that's the answer. Like an engineer, like an engineer got an answer. But I but the business side of me would say, a rejection. That's that's not an answer. That's just part of the conversation. Did music influence this or how did this just a quick note about our guests. I host the Breakout CEO podcast to share behind the scenes insights from scaling businesses. As an attorney, I see the real challenges leaders face long before success becomes public. But

Client stories have to stay confidential. So we invite guest CEOs to share their own moments of struggle and success. I'm so grateful to our guests and my team at Intellectual Strategies for making this show possible. Now, let's get back to the show.

George Hartley (11:10)

I've never thought about it that deeply, but absolutely like trying to hustle a you know, a indie electronic band, yeah, is is all no's. Yeah. And you know, gigs and and and and you know, putting out releases and getting signed and all that stuff. Yeah, it's it's it's very good grounding for enterprise sales or or even just growing a startup, go to market, like yeah, having a band is is

You know, I th I actually think the two most formative things for for what I'm doing is probably tr training in a in a rowing eight. You know, we had a a good rowing eight and being in bands because they're both like horrible to do mostly in the grind of perfection and hard work and it's just nothing feels good about

Jeff Holman (12:05)

Practice practice.

George Hartley (12:07)

And yeah, and and then and then and also with with trying to grow an indie band, you know, all the the hustle stuff, but but then in retrospect they're fantastic 'cause you get somewhere and you feel like you've you've done something so good. And so yeah, that's sort of it's actually I think about that as like where, you know, if where I learnt the kind of the persistence stuff for

not stopping with building startups. It it actually is is those sort of experiences, I think.

Jeff Holman (12:38)

And so you went to school, the place where you weren't supposed to go, but you talked your way into it. And you and you ended up building Blue Thumb. Tell tell tell me a little bit about Blue Thumb. Yeah.

George Hartley (12:46)

Yeah,

Blue Thumb is an online art marketplace. So it's Australia's biggest online art marketplace. artists sell their original art, you can see a bunch behind me. Yeah. and it's it was we we started in twenty twelve, my brother, co founder, and another guy, Phil, and we were all working n

jobs at the time. You know, I was making apps at an app maker after uni. Actually I think I was finishing uni I was finishing uni. I'd got a job at this app maker. And again I'd sort of I wanted to work there 'cause they made great apps and I I went and and I just knocked on the door. They weren't hiring for roles apart from devs and I'm like, can I do anything but that 'cause I wasn't a very good dev. Okay. And they're like, no.

Jeff Holman (13:37)

You're a dab if you want

George Hartley (13:39)

And yeah, I sort of look, I'll do anything. I work for a hundred bucks a day, you know, design, marking, whatever, and admin and and eventually they kind of said, All right, we'll try it for two days a week. And that like I managed to be useful enough. And then I became I was studying, I I did some design, I became the UX designer, even though I was I was doing this dev course. And I loved that job. Like it was the first job I'd ever liked, actually loved and

Yeah, we're making these gro these great apps. And was exactly what I had hoped. You know, these these these apps were were super cool and everyone I worked with was just so good and passionate. And like very deep nerd tech. Every conversation was about something technical or some new new thing. And it just felt amazing. And so that job, like I I adored that job and did that for a couple of years. And then but we we

We had an entrepreneurial st streak, my brother and I. We'd always we always sort of wanted to do this stuff and we we bought a little email company on the side from flipper dot com that we're running for money, like a little side hustle while we're doing this. Literally just

Jeff Holman (14:49)

Is Flipper is that a was that just a like a buy a buy a small business type of

George Hartley (14:53)

It's it's l literally F L I Yeah, yeah, no, it's it's yeah, it's it's a marketplace for for buying little online businesses. So we bought this little thing and we're sort of running it and growing it just for literally for money is interesting. And then you know, Blue Thumb came along and we were like, Okay, we're running, you know, we're at these jobs, we're like, let's do a little online arts mu marketplace

Marketplace, you know, we liked marketplaces and we talked about doing a wine one and I'd talked about doing a music one, but SoundCloud was really good. I couldn't see how we could not, you know, what what need that wasn't filling. But art didn't have anything and and dad was a painter and I, you know, was good friends with some painters from school. And why don't we just kind of do, you know, SoundCloud for art? And so we started doing that as a side hustle.

And it got to this point where it yeah, it it sort of needed us to go full time. but we all had these other jobs and I loved the job. And yeah, it was it was a really hard decision to leave yeah, this this app agency and and and go into the startup full time because I wasn't as much worried about the money and I kinda thought maybe if things all went wrong they'd probably have me back. But it was more about

only it's the only job I had ever l loved and anyway. It turns out I I love growing startups. So yeah, that was the start of it. And we grew that, we raised some money. and that is still going, you know, it's it's still selling art. it's sort of, yeah, you know, it's got thirty thousand Australian artists. It's I'm really proud of kind of what yeah, what it's done. It's done a hundred over a hundred million in sort of art sales and most of that goes to the artists. so yeah, it's it's it's yeah, it's great. It's what it what it's sort of

What it's done there is is awesome. and then when you that's

Jeff Holman (16:53)

Exited or is that something that you still

George Hartley (16:55)

that's still going. So yes, still still kind of an owner and and and a director, but I stepped back from running that to do a SaaS company in the email space called Smarter Mail in twenty sixteen. That's no, there's another one. So yeah, it's like it was it was similar to the one we'd bought, but this was purely for e commerce.

And so it was sort of around the insight of, well, you know, Shopify and big commerce stores, often they're run by small teams who may not have experts in email marketing, but they have all the data. And so can we build a kind of email tool that sort of lets them use all of that data that's coming through from their customers and products and everything else and to do kind of to do better email marketing than just

than just kind of spray and pray, even if they're not an expert to set it up. So it's trying to be

Jeff Holman (17:55)

So

this wasn't an agency where you provided services. This was a tool that the e commerce companies themselves would then subscribe to and it would help them do it do in house email marketing better.

George Hartley (18:07)

Correct. Yeah. Exactly right. Smarter

Jeff Holman (18:09)

Smarter.

George Hartley (18:11)

mail. Yeah, yeah. didn't help that probably, you know, Phil and I were doing I'd say we're both maybe slightly dyslexic and so we're like, we'll do smart email without the E because the domain is free. And then from that point on for the next seven years, people, when you're on an onboarding call, would look at it and go like smart mail, smart smart mail.

Jeff Holman (18:29)

Yeah, this is easy, it's smarter. Come on.

George Hartley (18:31)

I

know. You learn these lessons. so yeah, no, that that was that was a good journey. has it had its ups and downs, but we raised seed on that and grew it and we were acquired at the towards the end of twenty twenty two by a fund in the USA called Relay Commerce, who sort of roll up e commerce software companies.

Jeff Holman (18:58)

Still

a pretty good time for evaluations for those types of businesses.

George Hartley (19:01)

Yeah, yeah. In retrospect, the timing was good. 'cause you never know, but it did feel like when we started, 'cause we had someone approach us early twenty two to buy it. and so we thought, let's run a proper process here. You know, w we we actually had a a SAS sort of broker type small kind of consultancy help run it from the USA that I think really helped us.

selling a company is one of those things you you probab you don't do mu you might do once or twice or something. It's like buying a house or I don't know. And so you're not gonna be an expert gen like unless you're unless you're in the game. So yeah, I was I was very glad we we went with those guys. and yeah, they they did a great job because it it was a hard long process and the first guys, you know, we we they we s do signed a an exclusive

L O Y or whatever. So basically got to the end. Yes. Locked you in locked for the D D and I think they got maybe sixty days, I can't remember now, but they, you know, locked us in once that and then it was like we don't quite have the money. It was an excuse at the end, you know. The the numbers w hadn't changed, but it was they sort of were a no and they're allowed to be, but that really, you know, that was like

Jeff Holman (20:25)

Why are we so locked in then if you're not gonna

George Hartley (20:28)

Well yeah. So so it ended up being a longer, harder process, but the outcome was good. yeah. But at the end of that, man, yeah, I was pretty burnt out.

Jeff Holman (20:38)

Were you? Do were you able to take some time off before you jumped into your next venture?

George Hartley (20:45)

yeah. I well, I I I went I went back and joined Blue Thumb. to sort of I'd I'd been helping on product the whole time. I went back to to sort of head up product and then stepped in with as sort of co CEO alongside my brother for a year or two. so I I probably didn't take a big enough break, I would say, that I should have, you know, in retrospect. but yeah, it

You know, you sort of it's it's hard to know at the time how much time off, whatever you need. I did go and do a a vipassana meditation, you know, one of those silent ones for ten days. Yeah. yeah.

Jeff Holman (21:24)

When the is that when you started because you you mentioned in our icebreaker that you that you do meditation on a daily basis. Is that when you started doing it or were you already doing meditation before that?

George Hartley (21:34)

no, I I I'd sort of s I started meditating maybe a decade ago. It was actually I think it was a Tim Ferris. I like his podcast. Yeah. Yeah. He he's one of those kind of turbo guys who's a mile a minute and I remember him saying meditation really helps him kind of focus on his priorities and I'm like, I should try that, yeah.

Jeff Holman (21:57)

Well and you also had a you also had a your first I think you said your your oldest is four. So you would have had your first kid sometime around that same period, right? So that you you were busy selling a business, having a ba a baby and being like, I I imagine there was some stress there where you're like, Well, do I take time off or what happens?

George Hartley (22:14)

Yeah, yeah, that's right. I think I had a a one year old and Okay. Yeah. So yeah, I I I went in I went and did a Vipassana silent meditation for yeah, the ten day one and yeah it yeah, it it was it was good. You know, that was that was that was hard, but I came out feeling pretty refreshed, I'd say.

Jeff Holman (22:36)

Yeah. So at least a little bit of a break, before jumping back into to Blue Thumb and and you were there you said you're there for a f a few years at Blue Thumb to helping out, co CEO type thing.

George Hartley (22:49)

Yeah, we're probably another two years were there running it and it it sort of it it had a massive run up throughout COVID. Obviously a lot of a lot of, you know, companies that were selling stuff for homes or whatever, you know, it really yeah I think it five X'd. which was good for, you know, in a startup that'd been going for, you know, six or seven years. so that was that was awesome and then then suddenly the growth was so much harder to get after that.

Jeff Holman (23:19)

Really.

George Hartley (23:20)

yeah. And because it was like an Australian art startup, the you know, the the market itself has has a bit of a kind of a cap on it without expanding into other categories or or other countries. And so, you know, that next big leg up of growth, you know, we we were sort of pushing at

for those two years and we never really cracked, I'd say. And so I I think after, you know, two years of that, you you sort of start losing just momentum yourself. So my brother and I stepped back from Blue Thumb end of last year. Okay. And that was when I properly had some time off for the first time since twenty twelve, I'd say. Wow. and

That was it was a magical time to have to do whatever I wanted because, you know, December last year was when AI really turned a corner to, okay, this this is this is as good as a dev, you know, this is it was this like there was this point and I was just starting to get into kind of poking around and clawed properly and I had all this time.

So yeah, it was it was pretty awesome. and what actually happened

Jeff Holman (24:53)

Yeah. I was just go ahead and go ahead and finish that statement, so

George Hartley (24:57)

Well, yeah, I I was I was just gonna sort of talk about so we we've now, you know, the sort of we've got the band back together, the smartmail guys. Yeah.

Jeff Holman (25:07)

Yeah.

George Hartley (25:07)

And we're doing NitroSend, which is like agent first full stack email marketing. Yeah. And it came about because it was during summer, I have a book website that I like. I you know, I actually bought it many years ago. It's a bit like Blue Thumb, but it's it's kind of

ebooks authors can put up and readers can download free and I build a little e-reader over summer as well. So kind of like Kindle Unlimited, but basically all free. So pe you know, authors who just want distribution and a big reading audience and audience and as Culdo Buco. And I was like, well I'll I'll tinker on this, I'll grow this, you know, it makes a bit of money, I'll I'll add some features and do this for now.

Jeff Holman (25:52)

And what w well sorry, what was it called? E Booker? Is that what you said?

George Hartley (25:55)

Bookco.com.

Jeff Holman (25:57)

book O. Okay.

George Hartley (25:58)

Yeah. it's it's it's got it's got 850,000 readers signed up. It's got a big reader base yeah and a few thousand authors. And I was sort of tinkering on and I'm like, this is gonna be a one-man thing. And I'm like, sweet, I'm gonna I'm gonna automate the whole thing with Claude. So I was automating my content, my SEO, my outbound to authors,

my admin and email. I you know, I'm like I'm building skills and and running everything for my agent. Mm-hmm. And email is a a vital channel because it's got almost a million members and it's like the the easiest sort of way to really communicate and grow with them. And automating the email was was clunky. I'm like, God damn it. So I'm you know, I'm using these these tools that I know about, you know, that that's kind of, you know, the normal ESP tools and

And most of them didn't even have MCP connectors and the ones that did, you couldn't do the right stuff. And I'm like, why? Why is every channel but email like like up to date with with with AI? Why can't I do this from my agent? And I spent all January like, you know, I it'd be so annoying because I'd I'd get so much done in every other channel and then I'd have to go to email and like have to make all these changes for an hour or two.

Jeff Holman (27:12)

It's the big blocker there. Why why do you think that was? Is it the email service providers like they know the value of it and they kinda wanna hold on to it or?

George Hartley (27:21)

The bigger incumbent ones have a it's it's a kind of old school established channel. So the bigger incumbent ones, the ones I was trying, I tried three of them. They have a massive feature set. So, you know, you have have so many different features, and you might have a million users using them as well. Yeah. And so to kind of re-engineer that whole thing to be completely

Agent first, like that runs from MCP, so that someone can sit and not even really look at their UI and say, I want to set up, I want to set up flow, you know, nice design flows for my my you know four different types of users. I want to do weekly newsletters, I want to do 30 different transactional emails, and I want to also look on brand and be in my voice. To to kind of rebuild that is is kind of almost an impossible task. So that's

kind of where I got to with why the incumbents sucked. And then I'm like, I don't know. So I called up Cam, who was the CTO from SmarterMail last time. Like, mate, what do you know, you got a solution here? What do you think? And then I was like, no, but it sounds like something doing because he had some side projects. And I called up my brother and I'm like, Ed, maybe we should kind of do SmarterMail but completely from an agent, you know, like because when we sold we actually weren't allowed to build.

in the space for for a while. So we we wouldn't even be able to do this before. And it's like, yeah, yeah. And so Cam was like, I reckon I can get an MVP up in two weeks. And they're

Jeff Holman (28:58)

really?

George Hartley (28:59)

like, okay. a little longer than that. But yeah, we basically just kicked it off in February from that because we all had side projects to do. And we got to dog food it throughout March, like with our stuff.

and then in April we opened it up to friends who are game enough to like try kind of fairly buggy software. and yeah, it it works. It's like it for anyone who's done content marketing, it's like there's there's a lot of grind to it. You know, there's a there's a lot of just rote work, there's a lot of pushing pixels and yeah, it it feels like you're wasting your life, especially if you're a content marketer.

So yeah, we're kind of relieving people we're setting them free from that, which is a nice feeling. So

Jeff Holman (29:46)

people that so so you use this for your book your book company. Who who are the people that that really are the ideal user for this type of this type of agent first email marketing system?

George Hartley (29:58)

The the ones who are who are kind of locking on it quickly right now and the ones who are sort of upgrading to paid accounts and etc. all that stuff are mostly startups. and mostly they're kind of folks who are building a lot w with AI. so yeah, it's it's sort of it's fairly broad in that it's it's you know, if if you're a startup kind of scaling in

kind of any space that generally you're using you're sitting in Claude or Codex like VS Code with with these plugins running and you you want to like a solution to like do this well from that. so all of them, you know, we ever everyone who's sort of tried it from anything like that has has kind of started using it. We and we haven't had any churn yet at all.

Jeff Holman (30:49)

really?

George Hartley (30:50)

Yeah. Well we're only you know, we only took the covers off properly in June, but you know, gone zero to twelve hundred kind of

customers you know, very quickly and and the sending volumes growing very quickly. so yeah, that that's that's our current kind of ICP, I would say. we have some people do who sort of do content and newsletters, but we, you know, we there's there's a lot of good options there as well, you know, and and folks like Beehive and whatever, you know, they they really do that newsletter thing very well. So we're sort of zooming in more on, you know, people, people building startups.

and the funny thing that's happened has been we've had all these requests we never had in thirteen, you know, in ten years of doing email, we've had requests for like constant requests for AI outbound. And we it never really came through much and the others and but you know, they all because AI can kind of personalize a bit better.

But outbound where you're finding leads, you know, it's that horrible spray and prey. You know, it's like, it reflects badly on your brand, even if you're spamming people, that stuff. Like the these people are trying to build a great brand as well as their startup. And it's like, Can I I want to do this better? Can you do it? And so we weren't expecting to build that. And so we're we're we're building it right now. We're gonna ship it because it it

It's email and it's something we can do better. So yeah, like we let's do it.

Jeff Holman (32:23)

What what kind of lessons did you guys take away having you know, having the same team that had already built and and you know, successfully traversed the the journey with with Smarter Mail? What did you take from Smarter Mail? Not literally, but what what kind of lessons and takeaways did you did you glean from your experience there? And that helped you do Nitro Send as a as a company better?

George Hartley (32:51)

Yeah, there's there's quite a few. and I put it in a little set of values actually. it's blue thumb as well, like and like to to l list them off, like number one is deep pockets well capitalized. Like we always were proud of of running lean and you know, Austr that Australian mindset of like raise a small amount, get profitable. Yeah. But

Actually it can hurt when an opportunity comes to spend and grow, you you don't want to risk it. So it can it can mean you don't take enough risk and miss those opportunities. You know, you'll fail more but but you you can have more shots at goal quicker to to to get the big growth. So be better capitalized number one. so yeah, we we would raise the pre pre seed round on a on a pitch deck sort of like which I wouldn't have had the gumption to do the last two times. So

And we you know, we'll probably do a seed round sooner because the numbers are good, why not? Yeah. the other one is kind of high integrity team partners and investors only. You know, if if a customer is just gonna be too hard or whatever, you know, we're just gonna be a bit harder on that and fire them or whatever. Same with same with investors and everyone else, you know, just just set a higher bar on that, you know.

even if it means saying no to to some people. and the the the the the last one is kind of it's our first value and it's like you know patiently improve the core and and also invent the future. And like I was trying to sort of succinctly say, you know, we want to build something great by

Constantly improving the the main critical path, but also we want to work on on bigger moonshots that may not work concurrently. and it's Yeah,

Jeff Holman (35:00)

Yeah.

George Hartley (35:02)

and and and being okay with with that, like you're inventing the future, some stuff will will fall over. That's fine. Like it it can just building a SAS, you can get so stuck in the

I have to kind of I have to fix all these small bugs and I have to have feature parity across other competitors and all this stuff, you can get really dragged completely onto that first channel and not have enough moonshots. And so this time we we sort of having a very like a very thought through balance of of stuff that is building for what

may not be getting asked for right now by customers, but we think is is going to be super cool in a few months, plus improving the

Jeff Holman (35:52)

Yeah, and if you've got a stable base or stable enough, you know, then then why not why not add some of those moonshots to it? But what are what are some of the things that you that you thought you would be able to accomplish with your team going into NitroSend that have maybe not worked out the way that you anticipated? Maybe weren't as easy as you thought they would be coming into it.

George Hartley (36:14)

Honestly the hardest thing or the thing that hasn't panned out yet that I thought would have so f by f by now is is getting it's getting into the main partner app stores. and you know, if you look at our pre seed deck and growth plan, you know, it's probably three or four channels and and one very important one was while we must be a kind of an official listed

app in in, you know, some of in in these partner stores.

Jeff Holman (36:49)

Yeah. I mean we're talking we're talking we're talking Apple's App Store and

George Hartley (36:54)

Well, yeah. So th that's that's the equivalent, but you know, the the sort of the AI providers got it. because that's, you know, that people are using their AI agent and they have official kind of plugins and and these things and and getting officially listed, you know, you you suddenly have all this visibility and and a big funnel. And so my assumption was it would just be a you know, a linear process you apply and everything's checked and and you're approved, but that a actually hasn't panned out.

and so yeah, that you know, it it's just gonna take more work. so yeah, that that that's been that's been the biggest kind of thing that hasn't gone to plan, I'd say.

Jeff Holman (37:37)

Is it is it changing what you design or is it just a a matter of, hey, we're keep keep designing the to the plan and and we'll you know, we'll eventually, you know, add this piece to the to the business? Or do you actually have to do do you actually look at your roadmap and say, well, if this isn't gonna happen yet or for, you know, some time, like we're actually gonna build differently or make different decisions because of that?

George Hartley (38:01)

Yeah, we we had to adjust. because the assumption was, you know, for non-technical users, we'd get in and be a one click. hasn't, you know, we're not approved yet. So we basically have built an agent onboarding skill itself. So if you are in whatever agent, you're in GPT or Claude or Codex and and you say, I want to use Nitris and it can

Your agent can find the onboarding skill that is kind of listed and we've listed that on other directories and whatnot, and it can self onboard it by reading that skill and kind of connect. So that is the workaround, which works really nicely. We had to ship that and then SEO that.

not rejected, we're just not approved. but y that discovery, you know, we'll ho I was kind of assuming we'd we'd be in there now and that'd be a funnel. So yeah, just still waiting on that. but yeah, we we did have to work around it. We had to make make sure that that an agent can kinda yeah, self on board. I guess the other thing working in our favor has been the agents have gotten so much smarter that they they they can kind of just work it out now. Like they

Back when we first shipped in in March or whatever, you know, they weren't working it out and now now it's just like worked out, done.

Jeff Holman (39:34)

And it makes me think, 'cause I I think I read something about your and I'm gonna get this wrong, but on your on your website for NitroSend, something about almost like an interfaceless email, right? So that y you're not relying on the conventional interface to do the email. And it makes me wonder as you talk about this, the you know, the the AI platform, you know, app stores or whatever whatever they're called. I'm not sure they're called. As you talk about those, I'm like, that's really funny because

it seems like it shouldn't we we shouldn't need an app store for these. Like they you oughta just be able to type into you know Claude or Chad or something and be like, hey, I I want this and it should just pull up anything and everything, whether it's actually in the store or not. I don't know if I don't know if these these platforms have, you know, just backlogs of things that they've got to approve and review and and so I

the number must be astronomical of of everybody who's trying to get in at this point in time. But yeah. But it begs the question, you know, at what point will the the app store interface itself just go away? Kind of like, you know, the the email interface might be going away at some point.

George Hartley (40:48)

I I think exactly that and that's is probably part of their thinking as well. Like they you know, they've built app stores but it's probably a temporary thing, you know, like yeah it it it'll be they'll just be appearing as as widgets within within the chat interface w if they're not already, you know, I'm sure any day. So yeah, it it feels like a a a temporary mid step anyway. but yeah, it was it's just, you know, we'd sort of banked on getting in there and having that kind of funnel of discoverability, but

it the the actual connection and working and onboarding, you know, is is it's all solved by AI anyway, so yeah.

Jeff Holman (41:26)

Creativity loves constraints. We've been talking about a lot of creativity here. So this is a an opportunity to to, you know, look at what you're doing. And maybe there's a maybe there's a better way. I don't know. App stores are probably the easy way to go, but maybe there's a maybe this probably causes your team to sit and say, Hey, how do we do the SEO? How do we go out and get more customers? How do we build the base without waiting on you know, waiting on or relying on the app store itself to to be there? So have you guys found some some s some surprising

you know, channels or successes doing it the the unconventional way.

George Hartley (42:00)

Yeah, well it's nice having email and outbound to dog food. So we're we're using that, which is good and working. yeah. And we're onboarding we're actually onboarding affiliates at the moment. So folks who are who might who who're sort of in the AI space with an audience, so so on YouTube or even or even on X. and yeah, we just set up a sort of an affiliate program where if they want a referral link, they can kind of

refer us to their audience because they're a good they're actually a a good user of our product too. They they you know if they're collecting emails, you know, it's it's a great product for them to use versus whatever else they're using. So it kind of it's a nice, yeah. So so that's good with we've

Jeff Holman (42:45)

Or

George Hartley (42:45)

signed up for all these affiliates. Yeah. so we're starting to get that. And agencies has been another one. we got a couple of agencies discover us off X and

like the ability to set up a client and admin and kind of optimize clients and flick between them as well. You know, we we built early the ability to switch between your other brands and do it all from your agent. Okay. That's like just a massive time saver for, you know, marketing, email type even web dev agencies. So

Jeff Holman (43:22)

Yeah.

George Hartley (43:23)

that's been a really great early channel.

And then, you know, long term we are yeah, we are building for sort of SEO and GEO discovery and ranking and a little bit of a black box I I believe on the GEO, but we're doing the the stuff, you know, the right stuff we can to make sure we're doing okay with SEO and long term we believe that'll be an important channel.

Jeff Holman (43:47)

W when your when your team sits down and and talks about where you're headed, you know, without going into of course any confidential information, what w what are the highlights that your team looks forward to in the next two or three or four years?

George Hartley (44:04)

yes.

Jeff Holman (44:06)

Might is that too long? What what what do they expect by let's see, it's August. What do they expect by mid September or October?

George Hartley (44:13)

So yeah, we I think we we should have yeah, we should have an office here, hopefully, and a few more hires by September. October we should have a US presence. so the plan is to open a little, you know, w w one person office, hopefully, October. and

You know, that you know, the the USA is the focus for for where our customers are and also, you know, for for when we're raising money. So yeah, growing growing a bigger presence over there quickly. and like we just kind of you know, what was it? Microsoft riding the bear. It's like back in the early days, it's like just kind of trying to hang on and ship the right stuff.

For you know what I talked about with the the this it it it feels like the world is shifting on its axis right now. And very soon, you know, what you our original framing was, okay, cool. I reckon half the internet needs email. And I think everyone at some point will switch to running whatever they're doing from an agent. It's just so

So much such a better way to administer and grow a company and a website. Yeah. So we think our TAM is kind of half the internet, maybe.

Jeff Holman (45:44)

Okay.

George Hartley (45:45)

And then we started building agentic inboxes. So agents can first they could onboard and create agents can now create an account, start sending without a human in the loop. Then actually they need an inbox as well, you know, agent one at at at Nitrisend.com. And then they they're gonna do one to one on outbounds like.

Okay, but then what happens when agents are creating their own agents to build stuff and instead of eight billion people, there's a hundred billion agents running companies? Yeah. They all need this. So I'm like, actually the TAM isn't half the internet, it's it's a hundred billion agents and half of that who need email until something better's invented. So okay, if that is happening, how do we make sure we're a useful tool for that and and kind of ride that wave? So

That you know, that's why I was sort of laughing about next few years, because I really I don't know what the world looks like. So I just know that you know, I don't know, but myself is that that yeah, this sort of this this agentic kind of explosion is about to happen. I don't know how or what it looks like. And okay, let's let's build some let's build the best smart pipes for them to kind of communicate.

Jeff Holman (47:03)

Yeah.

George Hartley (47:03)

So yeah, it's kind of exciting and daunting.

Jeff Holman (47:06)

Yeah, I have I hadn't thought of it that way before. And you you mentioned earlier, I think when we were talking the icebreaker about getting together with friends and you know, other people and talking to them about what's going on and, you know, issues or solutions or whatever. I d I haven't heard this concept of it's a a TAM expansion, you know, effect here where y it's not it's not you know, whatever how many billion it's not three billion people, it's a hundred billion

Agents plus three billion people now that that is your market. Are are other CEOs talking about it like that? I mean, this is the first time I've heard of somebody say that and say, Whoa, our Tan you have to you have to rethink TAM now. It's it's not what not what you thought it was.

George Hartley (47:52)

No, I don't hear that much from other CEOs 'cause most of them are in the weeds a bit. We we we get to do more thinking 'cause we're real we're fresher to it.

Jeff Holman (48:03)

Yeah. Yeah.

George Hartley (48:04)

But no, but it it you know, it's it's the like I said, that Astra kind of discovery on the weekend, it's it is happening. This is like these the the next set of AI is going to be smarter than people.

And if you tell it, hey, I want to grow my business, I want to do this, it's going to say, right, well then to do that, we'll probably need some different agents that are gonna do outbound, blah, blah, blah, blah, blah, spin them up, how they're gonna communicate it's like it it just makes complete sense. And and so and I'm talking like a ten X TAM expansion in like, I don't know, eighteen months, two years or something. It's not it's not twenty years away, it is right like

It is it seems imminent. And so yeah, it's like, you know, what what do we build? What's the most important thing to build now? But also like for a few months ahead to to like if if we genuinely think agentic inboxes are are needed for agents to do this stuff, we're we're not really getting much user pool right now. There's there's no one who's building a a ten person startup saying, Hey, I need ten agent inboxes. No one's asking us for that, but

We've just shipped it because I kinda think that it will be useful. but maybe it won't and maybe it's something slightly different and yeah. So but I do I genuinely believe it's you know, there's this there's a big explosion about to happen in in the opportunities for this stuff and yeah, it's it's exciting.

Jeff Holman (49:37)

Yeah. No, you're you're making the I mean a lot of people are doing the same not the same. They're doing the they're they're thinking about it kind of similarly with, you know, it's we don't hire people as much. We hire smart people, but then we then we spin up agents to do a a lot of the tasks in the business. And eventually there'll be well there'll be some we'll call it a an agent recruiting business, right? That where you just say, Hey, I'm gonna start a company and and instead of hiring six people, it's gonna

It's gonna spin up twenty five agents and you've now got a fully staffed business with agents that I mean, I don't know.

George Hartley (50:14)

I I I was thinking that earlier this year, but my my thing has changed a little bit on that. 'cause I we're you know, w we've actually high

Jeff Holman (50:25)

As you don't want to try to hire the details here.

George Hartley (50:28)

And it's like I actually think it's more like when I don't know, computer spreadsheets came about, it didn't it didn't mean there were less analysts and accountants

Jeff Holman (50:41)

Yeah.

George Hartley (50:42)

and finance people actually kind of enabled a way bigger economy there and there's probably a lot more. And it's like, you know, z zero accounting, you get out of the written ledger into into QuickBooks and zero is probably

There's actually more white collar people doing this stuff than there were before, you know, p less agr agrarian stuff and actually way more. And I kind of think businesses won't have less employees. They'll just be doing like turbo amount of stuff.

Jeff Holman (51:11)

Yeah. Well maybe I sh maybe I present it the wrong way.

George Hartley (51:14)

You know, but it's it's mo it was my thinking too. I'm like, sh we can do so much. We're gonna be a five person start up and get to like a billion bucks revenue. I'm like, No, that's actu I I don't I've I've yeah, I've changed my thought on just recently. I'm thinking actually no, it's probably yeah, it probably means actually hiring more people for where it works and and an abundant opportunity. I just

Jeff Holman (51:35)

Be maybe it's be better, maybe it's move faster, you know, maybe it's one of those as opposed to replacing

George Hartley (51:41)

And invent more stuff like, you know, the internet was someone's invention or like Berners Lee Bernalese or whatever it is, I forget.

Jeff Holman (51:48)

I mean.

George Hartley (51:50)

Yeah,

yeah. Mo just more s stuff will be like everywhere.

Jeff Holman (51:53)

Yeah. Wow, this is this is this is cool. I you know, just like kinda how we started out talk talking about the Tamagotchi you know, over the overnight Tamagotchi build for your kids. it's cool hearing about all the stuff you're you're doing and how how you're thinking about things. When I asked about years, you're like years. We're we c we're talking weeks and months, maybe hours, days. stuff is just moving so fast.

with people that you I and you've and you've seen this, you know, across different companies, you know, from the agency you started at to Blue Thumb to Smarter Mail, or Smart R Mail, whatever we want to call it, right? To Smarter Mail to to NitroSend. Like you've you've been through the rounds here. you've had the benefit of working with a a team a couple of times. for somebody else who is on this journey,

And and they're looking at the maybe they're listening to this episode and they're saying, Man, I really like I really like listening to what George has done. How do I like what's a good takeaway for them to to to add to their, you know, to their skill set that they can maybe start thinking the way you're thinking or, you know, building something i in a little bit different way? How how what would you what advice would you give to somebody who's trying to go the same path?

as you are.

George Hartley (53:22)

It's it's really is it's kinda easy to say and hard to do, but like the the three things I kinda think you know, if I'm speaking to someone who hasn't you know, who has an idea and hasn't started yet or whatever, generally I just say start. Just start, do it. Yeah,

Jeff Holman (53:38)

Take action. Yeah.

George Hartley (53:39)

you you'll you'll learn and you know, the the best thing you can do is start. sometimes people are sort of in the early stages, you know, a chat with and whatever and they ask, should I quit my job and

you know, launch this thing and I I my experience was better it was better to do it concurrently for a little while and maybe go a little slower just 'cause you have less pressure on the thing you're trying to get going. so yeah, just I don't know. In general it'd be like whatever you're doing, start the other thing and and try. And like I said earlier, I I I like I like talking to people who are doing things.

It's just I find it inspiring and helpful and like often often some of those the growth wins, you know, trying different tr strategies and channels and that stuff, often you learn stuff that's worked that way. So yeah, talk to people, anyone who who's doing something interesting.

Jeff Holman (54:37)

for somebody who's further along the path and they're like working with a team, they're they're they're they're running in you know, they they're they've had some of that success, building traction, la you know, releasing the product, whatever it might be, who who runs into a wall. A little bit different scenario than the you know, founder trying to start up. What what would you say to that person at at that kind of breaking stage, if you will?

George Hartley (55:01)

hit hit those plateaus and problem stuff plenty of times. And I'm not sure I can generalize a way that's worked out of it. certainly it's important, like I said, to don't don't run out of money. So especially for startups like you know, the two big killers of startups generally are founders breaking up and pissing each other off so bad or just running out of money. And so

Definitely keeping an eye on that and doing everything you can, you know, assuming that you're one of these people that won't just kind of eventually stop when it gets hard, like you gotta you do have to keep an eye on cash flow and optimise and, you know, like think about even thinking about things like pricing and and margins if you're doing physical stuff or whatever. otherwise how how have we got out of

Jeff Holman (55:54)

I was just saying while you're while you're thinking about g how to get a growth route to what you're saying, I I really like it. It brings us back to what you were saying before about kind of that balance between you gotta have kind of a stable stable business, you know, keep it going, but but but think about the moonshots, you know, along the way and and being able to balance the two of those w I think was maybe you expressed it differently as one of your core values, being able to do that. But you know, don't run out of money. Get that g get that stable base built so you can take some big swings, right?

George Hartley (56:24)

Absolutely.

Like sometimes, you know, y you you hear these founder stories of like, you know, we we launched and and we had exponential growth and it was great. And the reality is that that doesn't exist really. Like and it's, you know, you you need to give yourself enough time to find the wins or work you know, work work out the tweaks. you know, that said, like

I haven't seen that many full pivots work either. It's sort of like generally you need to be in the right ballpark of building something pretty good for customers, have some vag you know, w be smart enough to work out, you know, an angle and and an improvement on something that exists, whatever. Like y you you need yeah, you you need to have enough runway and cash and whatever to be able to have some some stuff not work for you. You can't

Bet the farm on like something unproven as a moonshot, in my opinion. Like maybe you can, but I I would just, you know, you you don't wanna you don't want to get rid of your full margin of safety there. because like I have a million bright ideas. I wake up and I'm like, I'm in the shower, I'm like, yes, I'm a genius. Like I know, I know what's going to give us the next kind of kick up. And I go in, I tell the team, like, guys, you know, I saw this in a different category. It's

like listen to this and some of them go, okay, yeah, cool, we could try it. No, you know, and I reckon of all my like strokes of genius, my hit rate of probably one in four to even move the needle.

Jeff Holman (58:05)

Okay.

George Hartley (58:06)

You know, maybe one in three of these, you know, you you ship something or you try a channel or whatever, you know, maybe thirty three percent success rate that you can see you can see a change in in the metric. And so even though I'm

For thirteen years I'm like, I'm a hundred percent sure this is great and gonna work and I know what I'm doing. I'm still striking out two thirds of the time, right? Yeah. So you you wanna be able to kind of like ship those things quickly and learn learn how to sh learn how to test the smallest amount on this idea to break out. You know, you you just gotta learn how to do it as quick as you can, get real, you know, real evidence that it works.

Yeah, rubber hits the road when someone gives you some money on something new or whatever, so

Jeff Holman (58:56)

I wonder if that doesn't answer the the the question that we were that we paused on there with how to how to tackle you know a a a growth blockage, right? find find a meaningful pivot, make small changes, test fast, and find the way around or through that through that thing. Is that does that work? Does that summarize where kind of where we were going where we're going?

George Hartley (59:21)

What

generally works is, you know, one percent improvement on something that that is working for you, basically. You know. That I saw the the founder of Instagram say, you know, what w how they build a really good product was they actually just would talk to users or look at users and say, What's the best thing about Instagram? And whatever the best thing was, that's what they would try and improve. I'd just focus on like focus on that strength and and one percent better that 'cause it's so easy to try and build everything else and fill in your your weak points. And so yeah.

you know, for us generally, we've grown these things through patience on small improvements and my genius moonshots, you know, don't work often and very occasionally do.

Jeff Holman (1:00:04)

Occasionally. That's all you need. Well, George, it's been it's been fantastic having you on the show. getting hearing your story, getting your insights and I've got a few takeaways myself that I've gotta go re listen and write these down for for my own for my own benefit. But I'm sure the audience has taken away some of the some some insights too from from your story. So it's really a pleasure to have you on here and be able to to talk with you about your business and your your own story.

George Hartley (1:00:31)

Thanks, Jeff. Thanks for having me on.

Jeff Holman (1:00:33)

Yeah, and for for those of you in our audience who joined us today, thanks again for coming and listening to the Breakout CEO Podcast. Be sure to follow or subscribe on your favorite podcast platform. And if you enjoy the show, a rating or a review goes a long way. Our mission is to promote the stories of breakout CEOs in scaling SaaS, e-commerce, and tech companies to equip peer CEOs with valuable perspectives and confidence.

Thanks again for joining us on this episode of the Breakout CEO. I'm Jeff Holman, and I'll see you next time.

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