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Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between.
In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make.
Topics we cover:
- (2:25) – From agency owner to TinySeed-backed SaaS
- (6:38) – Walking away from consistent agency revenue to go all-in on SaaS
- (13:51) – Going all-in vs. splitting focus
- (16:13) – Why most agencies fail at SaaS
- (28:15) – What’s working, what’s not, and what’s next
Links from the Show:
- Join the TinySeed Mailing List – Applications reopen in September 2025
- Apply for TinySeed
- Coaching Call Bonus
- MicroConf Connect
- OutboundSync
- The SaaS Playbook
- Harris Kenny | LinkedIn
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify
Rob Walling:
Is this really an episode of Startups For the Rest Of Us on a Thursday? That’s right. For the next six weeks, you’ll find new episodes of TinySeed Tales Season five in this feed every Thursday morning. If you’re not familiar with TinySeed Tales, it’s a narrative style season based show where I follow a founder. As they navigate the ups and downs of building a SaaS, we dive into their journey to find product-market fit, optimize the product, scale their business, and hopefully reach escape velocity. These episodes were recorded over the past year, so you’re going to get an inside look at a founder’s journey. The goal is to give you honest insights into the challenges, setbacks, and hard won victories that come with growing a real SaaS company. If you’re new to TinySeed, it’s the startup accelerator I run for ambitious bootstrapped SaaS founders, and it’s the first accelerator of its kind Twice a year, we fund B2B SaaS founders who want just the right amount of capital, a community of like-minded, ambitious founders and access to mentorship advice and everything else you’d expect from a world-class accelerator applications for our fall 2025 batch open on September 1st.
This time around, we’ve shortened the application window a bit and we’ve tightened up the process, so we’ll get you a definitive answer much quicker. Avoiding the drawn out uncertainty common in other investment processes. The application is intentionally short and focused, and if you know your core metrics, it usually takes about 10 to 15 minutes to complete for all the details and to get notified when applications open, go to tiny c.com/apply and get on our mailing list. Let’s dive into this first episode of season five.
Harris Kenny:
My name is Harris Kenny, I’m the founder of Outbound Sync, and it’s an integration product between sales engagement platforms and CRMs.
Rob Walling:
Welcome back to Tiny Sea Tales, a series where I follow a founder through the rollercoaster of building their startup. I’m your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the first startup accelerator designed for Bootstrappers. This will be our first episode of season five where we follow Harris Kenny, founder of Outbound Sync. Harris has made the hard transition from agency owner to SaaS founder, and in just over a year has built his monthly recurring revenue to $10,000 a month. In my first conversation with Harris, I asked him why he applied to TinySeed in the first place.
Harris Kenny:
My SaaS product is built out of my agency, and it was the fourth iteration of a SaaS that I tried over a total of five years working myself. What really pushed me was that it felt like it was starting to really take off. I was feeling that the rocket is entering the atmosphere and it’s shaking and the bolts are moving. I was getting more deals coming in and bigger and bigger prospects and very mature companies saying, Hey, yeah, we’re interested in this. Here’s a security questionnaire and these things. It just started compounding and actually someone reached out to me who’s a TinySeed portfolio company, and he was like, Hey, you should think about applying to TinySeed, and I was like, oh, actually, it’s funny. It’s a long story. I’ve been following TinySeed for years and I kind of forgot about it to go into building mode, but now that I’m here and this is working, maybe I should throw my hat in, and so reached out to a couple of TinySeed founders. But yeah, it was that feeling of like, Hey, what if this works actually, and that was exciting, but also I don’t know that I want to do this alone basically.
Rob Walling:
That’s a good way to think about
Harris Kenny:
It. Not fear of success, but oh, this seems like it could actually work, so it’s like I should not get in my own way being alone. Yeah. If I’m alone, I feel like my odds of success are higher with TinySeed, basically. That was why I should try, but if it didn’t work, I was going to do it anyway.
Rob Walling:
Some of the challenges of being a solopreneur are obvious, the loneliness, the isolation, no one to spitball ideas with, but then there’s also this very practical human need to succeed if for no other reason than to support your family.
Harris Kenny:
I started my own company five years ago before my wife and I had kids because I wanted to have the flexibility and I was always able to in services, it’s very flexible. I was always able to pull a rabbit out of a hat and make it work, and we have great house, we’re very fortunate, but with SaaS, it was kind of like, okay, it is time for me to take this more seriously. When we got this new house, the process of getting a mortgage was so frustrating of how I paid myself through my own company and it’s like, okay, it’s time for me to grow up a little bit, and if I’m going to run that kind of company, I’ve known how to make it work kind of like a street rat, like Aladdin or whatever, but it’s like, okay, now I’m kind of entering a different world where there’s due diligence and process and uptime and you can’t just make up for it with a smile and working extra on a Saturday. It’s like if that thing is down, it’s down and you messed up and it’s a huge problem. So it was all of that, but also the upside of it’s like the best business model ever, and if I could be the one running that kind of business, the reward is pretty substantial and it’s really leveraged work. I solve a problem once and I sell it X times versus one and over one over,
Rob Walling:
And also it’s recurring.
Harris Kenny:
Yes.
Rob Walling:
Let’s say you went and raised friends and family or you raised an angel round and you hustled and you got money that wouldn’t replace the community, the mentorship, the connection, but there are other programs certainly out there. There are funds that have communities or there are accelerator regional accelerators. There are other options, and I’m curious if you evaluated those or for you, why TinySeed over the alternatives?
Harris Kenny:
Yeah, I think that TinySeed, it was definitely an end of one when I got to this point because MicroConf community, this is going back to 2020, kind of started me down this road and start small, say small, and the stair stepping method, those ideas were very early on. It was small dominoes that started, but it took a while for the dominoes to get bigger basically. And so it kind of shaped in my mind how I was thinking about what I wanted a business to do for me, for my life, for my family, and then I went through this circuitous route. So I think that’s part of it. It was very early influence in terms of setting what’s possible. In my mind, it’s like it doesn’t have to be a billion dollar company to be successful. There’s actually many, in fact, hundreds of millions of different little price points between zero and a billion that would be really successful.
So I think that’s part of it. And then it was sort of wandering through the desert, trying a lot of ideas, trying to run the agency slowly getting better. I mean, we had some good months. I mean, I had some agency months where we were over 30 K in build services. Good. It was a good agency, but as the SaaS part started growing and that MRR kept growing relative to the agency side, it was like, no, I really wanted to build a B2B SaaS company. I don’t want to build a productized service. I don’t want to have some goofy combination of things like multiple bets, a little app here, a little app there. I want to build a single B2B SaaS company that solves a really specific problem and that moves up market and that can solve enterprise level, really highly complex issues of what we do are on block lists and syncing data.
It actually gets pretty thorny, and we’re in a really, really small area, and so it’s just like, I’m going to need more power firepower like my team and I want to build a B2B SaaS company. That was it. And the other ones I talked to that I looked at over the years were like, well, we’ll invest in this, but also this. And also their thesis was so scattered that it was kind of like, I don’t really want that and I want somebody who’s going to be like, Hey, let’s talk about churn for two hours and we want to talk about it, and you want to talk about it. And by the way, you have 12 friends who are all similar spot who also want to talk about it. That was what I wanted, not just a general panel about how do you keep your customers happy. It’s like, no, no, I very specifically want to solve this churn problem.
Rob Walling:
Yeah, no, and that makes a lot of sense, and that is how my career as a professional has evolved because if you go back to MicroConf in 2011, it was the conference for self-funded startups. It was not SaaS, and it wasn’t until really 20 15, 14, somewhere in there where I was like, oh, SaaS is where I want to be, and the deeper I go, the more value that I can provide, and by deeper I go, I meant startup For the Rest Of Us went all SaaS at that point, and I just told people I’m not answering questions about info products anymore. It’s not that I don’t like info products. It’s not that I don’t make info products. I have courses, I have books. Everything I do on the MicroConf side is kind a course information product. It’s not that I don’t like those, it’s that I can’t help you as much if I’m not focused.
It’s why my books now, I have wrote a book called The SaaS Playbook. It’s not the Startup Playbook because for exactly what you’re saying is the moment that you rise up one layer of abstraction, you lose granularity and two hours on churn makes no sense. If there’s a biotech company next to you and a hardware company on the other side and a two-sided marketplace on the other side and a B2C company on the other side of you, you don’t share that same depth. And I was concerned early on about pigeonholing, and frankly when we launched TinySeed a and r, my co-founder, for folks who were listening Cog, he was like, it’s b2, B Cs, that’s what we’re doing. I was like, but maybe what if I’m the person who was like, but we could and I think it’s the best decision we made
Harris Kenny:
Looking at our batch. It’s like these companies are structurally similar in the important ways, but so different. And it’s amazing how much you can learn when real estate titles is one of our batch companies and Go links, but then you hear ’em talking and you’re like, oh, actually no, this is totally relevant. Even though if you talk to a normal person, they would be like, those are three different companies,
Rob Walling:
But a lot of commonality,
Harris Kenny:
So I can see how, and you learn from that. So yeah, it’s just a very specific way to operate. But within that, I think there’s a lot of variety.
Rob Walling:
Well, and it speaks to secretly slash not so secretly, what do any of us want to do? We want to operate a company that is probably best in class, and I want my companies to always be the gold standard. So I want Drip to be the best at what it did, and I want people to think highly of it, and I want MicroComp to be the gold standard for bootstrapped entrepreneurs, and I want TinySeed to be the gold standard for B2B SaaS accelerators, period. I want to be the best in the world, otherwise why am I doing it? And it speaks to that’s a long road. You have to build a brand, you have to do all this stuff, but it speaks to that it was a factor for you of, oh, well, I’m B2B SaaS and therefore I want the best that I know. I dunno, I guess that means a lot. I normally on tiny sea tails, I’m not the one kind of having a realization, but every time I hear that kind of thing of why did you apply? And it’s like, well, your B2B SaaS and so am I. It’s like we made the right decision. You know what I mean? Going narrow is often often the right decision.
Harris Kenny:
Yeah, well, I mean especially at that point, because at that point our MRR was, I mean this is April, it was like 7,000 or something like that. And I still had mean in May, this was my last full month of the agency, we did $30,000 in revenue, but then almost a third of that was the SaaS. So I was getting basically my time. I was really busy then, and then I had these big customers who were paying me big amounts and the SaaS was getting close. I was like, I don’t probably don’t need to do this. But when I talked about it with my wife, she was really encouraging of, this is the thing that you’ve been wanting, you should go for it. Don’t go halfway. And I will say two months out from that decision, just speaking about the point about focus, these two months of the SaaS now really taking off and then the agency petering out and slowly winding down.
It has been so much work running both. And during the process, I remember Tracy was like, look, you run your company, but just so you know, if you’re working on it, we want it to be the thing that you’re working on. We don’t want you to have seven other things going on. Which I was like, okay, I get it. Okay, no problem. But two months of having both is like I literally, I don’t know if I could do this for another month or two because, and so I’ve seen this relief, but also I’m having much better ideas and I’m having, we can talk about the go-to-market stuff, but that is starting to really, really accelerate. And I’m also seeing with my team, our developer, he was part-time before and then once joining TinySeed, I could say, Hey, you’re 40 hours now. And oh my gosh, he’s just ripping and I’ve got a funny story from the kickoff about that, but he’s just ripping through tickets.
And this is kind of goofy, but personal example. We have a nanny who he hired and we’ve had this mix mishmash of daycare in the past, but having a full-time nanny who she’s really good and she’s like, this is what I do. I take care of kids and I help you help your family. She’s helping her in the house and she’s doing laundry and she’s cleaning and she’s so playful with the kids and she’s coming up with these activities and it’s so different than when we had a part-time nanny and then a grandma here and then spend time with a neighbor there. So there’s this whole deeper thing that I’m kind of processing about focus energy and what are you doing, whether it’s our developer or a nanny or me having one company, and it seems so obvious, but it’s just slowly permeating my whole brain.
Rob Walling:
I’ve learned through personal experience that when you try to run multiple companies at once, all of them suffer and so does your personal life. That’s why we require any founder we invest in to fully commit to their idea. That’s what I told Harris when he applied to be part of TinySeed, and he was skeptical at first, but ultimately he came around
Harris Kenny:
When I said, okay. I thought it was like, okay, this is kind of not a concession, but a little bit of a concession. But of what I’ve come to realize is that it has actually, I think benefited me disproportionately because I own most of my company, almost all of it still. And so my company’s doing better, so I benefit way more. And my personal life, my whole thinking on that has flipped. I mean, I wasn’t salty about it before, but I was kind of like, okay, this is a choice. I’m giving something up here, but I feel like I’ve just been freed to just build this thing that after spending all this time years trying ideas and posting and getting feedback, I finally have this idea that really smart people are like, Hey, I want a, so it’s like just do that thing. This is it. Just do it a lot. You
Rob Walling:
Have caught a tiger by the tail, lightning in a bottle, whatever analogy we can use for it. And it’s like, don’t that up by half-assing it because someone will eat your lunch. This is what would happen if you worked on this and three other things is it would grow slow. You wouldn’t give a full attention. You’d be distracted when you’re doing dishes, when you’re walking around, when you’re in the shower, whatever. All your thoughts are scattered between three and four things. It doesn’t get the attention it deserves. It’s not even the hours, as you said, you have best ideas when you’re focused and your best ideas are what’s going to 10 x this business? It’s not the split
Harris Kenny:
Focus. There are two agencies who had been working on a similar thing, and I’m seeing us separate. I’m seeing us getting mentioned organically in other places, and I’m seeing us getting referrals like, oh, that’s Harris’s thing that, oh, outbound sync. That’s all they do. Even though those other agency owners, by the way, are super smart and I know that they’ve built really good integrations that are working for their individual customers, but they’re also doing their thought leadership posts and they’re also trying to get known for other things. And so I’m seeing that play out right now. What could be a direct competitor versus a Zapier make or something?
Rob Walling:
I want to touch on something you’ve already brought up, which is you had an agency doing outbound for paid clients, and as you said, you built it to 30 grand a month and you launched a successful SaaS out of that agency. The thing with building a SaaS out of an agency is every agency wants to do it. Some agencies try and almost none succeed. It’s very, very hard to be running agency or consultancy managing clients. You have freelancers or full-time people doing day-to-day work. It’s like, I got to give 40 hours of work in just for the clients that I’m trying to do the SaaS on the side. Is it nights and weekends or am I not taking paying work to do this thing that is not paying me or may never pay me? And that’s the balance, right, is if I can bill a hundred dollars, $200 an hour, whatever it is, thousands of dollars a month, why wouldn’t I just do that? Then actually focus on the thing that might bring me thousands of dollars a month, a year or two down the line? My question for you is how did you do it? When most fail, why have you succeeded?
Harris Kenny:
I think the first thing I would say that I feel is that where I am right now is that this is kind of the getting into TinySeed, winding down, the agency starting this ass is kind of the end of the beginning. And so I see the early development of the project is kind of prologue, and obviously there’s a lot of work to be done from here, but how did I get from prologue to here? I think I just really, really, really wanted it. I really wanted to have this kind of company seeing other SaaS founders who kind of got to later stages and what their life looked like. And it was just like, I want that. I want to be around. It’s really important to me to spend as much time as I can with my kids, but also have resources so that they can do cool things and travel.
My wife and I love to travel, so I think that I really wanted the outcome and this idea I stumbled on by accident. I had a customer who basically wanted this product. They were right for the wrong reasons, they were too small to need it versus what I’m seeing who actually needs it these days. But I built it just because I felt like I could, and frankly, I wouldn’t be here if I didn’t have Chad GPT because I built the first version of this with Chad, GPT, and I thought it was like, I saw there’s this funny quote of we do hard things, not because they’re hard, but because we thought they would be easy. And that’s how I ended up here. I was like, oh, I can do that a make.com scenario, no problem. And then I use chat GPT, I just need one API call and I can do everything else in make.
And then I posted on LinkedIn and more people were interested. And so I started bundling with my campaigns and I started saying, Hey, if you want to do outbound with us, you have to be using HubSpot and we use our integration. And so it was kind of forced coupling of the two products. And then if the product was falling short, I could always make up for it on the services side. And then slowly I started to have people say, well, we don’t want to do campaigns with you, but that sync thing sounds cool. Can we just have that? And so then I sold a couple of those and that was the first time I felt like, oh, I have actual SaaS revenue here. They’re just paying me for a product and I haven’t talked to them in a month. And I checked in with them.
Service anxiety was like, Hey, how’s everything going? And they’re like, yeah, man, great. What’s up? Why are you emailing me? I was like, oh, have a good day. Alright, see you. Good to hear. Let know if you need anything. So that was how I think stepped into it. I did a trade with a development shop, running campaigns for them, and then they refactored the code from low-code to code. So it took four months of low code, two months of refactoring to real code, and then that’s when things really started. So I kind of count our MRR in October when it was running through the real platform and I wasn’t manually connecting make scenarios and stuff like that. The product was just so bad then that it really didn’t count. So yeah, that’s kind of technically how I do it, but it was nights and weekends and it was weird hours.
There’s one story that I just like, I’ll remember this for my entire life. So we had also had some really intense family medical stuff. That’s a conversation with our day. And then my health also, it’s been hard to be healthy. I’ve not had the best lifestyle, losing a lot, not a lot of sleep, not great food, not great exercise. So it’s been very difficult. It’s required a lot of different sacrifices that I’m trying to correct a little bit now. It was three 30 in the morning in Denver, one of these early customers who said they wanted it. I connected it through make this guy’s in Warsaw, he’s in Poland, and I’m messaging him on Slack. I’m like, Hey, I fixed that bug. He’s like, okay, great. I was like, do you want to talk about it? I just want to make sure that it’s working.
He was like, now, right now, aren’t you in Denver? I was like, yeah, I’m awake. Are you free? Let’s talk. And so we hopped on a slide huddle and we talked for 10 minutes and he was like three 30 in the morning and he was like, are you okay? I’m like, yeah, yeah, I’ve just been working on this for five hours. I’m not doing any kind of drugs or anything. I’m just working on this for five hours and I need to hear from you that it’s working so I can go to bed head. And he was like, you’re a zombie. I was like, I dunno, I just really want to solve this right now and then I’m going to go to sleep. And so not being a developer, there were times where things were probably way harder. Like GPT isn’t actually that good at writing code, but it was like sacrifices like that, being lucky, having good support, a lot of other things. But yeah, that’s my reflection on that stage.
Rob Walling:
I like that and I want to tease it out. I often say success is three components of varying degrees. It depends on the story. The components are hard work, luck and skill. And the hard work is you doing what it takes and staying up till three 30 morning than doing it. I’m not saying that neither you or I agreeing you should do that every night, nor is it healthy. But sometimes there are points where you have to do this, you have to do the work, you have to schlep, you have to be the janitor or you have to pull an all-nighter to do a thing or work a 60 hour week here and there, not for the rest of your life to make it work. So the hard work is obvious, the luck, I think there’s a bit of luck that you stumbled upon an idea that was an obvious need from the start.
And this is where it’s like, is it luck or did you make your own luck by starting an agency, by developing the skillset that you have as someone who can sell, as someone who found clients, and as someone who put in the work to build an agency to 30 K to then create opportunity for yourself. So I say doing things in public creates opportunity and by in public sometimes that’s a blog. Sometimes that’s starting a company and then realizing, oh, there’s actually a deeper need here. So all of these factors are at play in your story. And there’s an element too of, I guess we could put it in the skill bucket, but it’s like you were smart enough to realize, oh, this need for this customer is something that I should build in no code, or I should build a code, frankly. But you didn’t have the skill at the time. And so it’s like there’s a scrappiness to this story of just kind figured it out, went, did G PT and wired it together with make, I know some founders or aspiring founders who just wouldn’t, they wouldn’t take action. They wouldn’t do, is it too risky? Am I wasting the time? What if this doesn’t work? What if it breaks and the client gets mad at me? What? And it sounds like you took a lot of action very quickly because all of it doesn’t have to work just 70 or 80% of it does, right?
Harris Kenny:
Yeah. Yep. Yeah. I mean, my threshold was can I get this working well enough that I can with a straight face talk about it on LinkedIn and I mean WhatsApp groups and Slack groups with some outbound folks too, and share it and see if people are interested enough for me to keep working on it. So that was my threshold. I never misrepresented where the product was, but I would literally finish something and then be recording a video of three minutes later being like, look at what Aon sync can do Now. There was no one month leadup. If we’re releasing something new, it’s like literally, I just finished this. It’s worked one time. I’m going to talk about it.
Rob Walling:
And that we see this with the most successful TinySeed founders. I have a list of all the seven figure TinySeed companies in a simple note doc on my phone. And if you go down that list and you look at the founders, guess what all of them do? They all move very quickly. They ship things very quickly, and they generally work on the right things. They’re not right all the time, but they’re right enough at the time. You don’t need to be right a hundred percent if you’re right, 60, 70, 80%, but you’re just shipping a lot of things quickly. You hit it. It all doesn’t have to work at this point. It’s cliche to refer to the entrepreneurial journey as a roller rollercoaster, but it’s not inaccurate because there are challenges, fear and times when nothing’s working. But there’s also optimism, things that excite you, moments where everything comes together. I was curious to find out what was keeping Harris up at night? What kind of headwinds was he facing?
Harris Kenny:
It is definitely myself still. There’s the mindset shift that I’ve been trying to undergo in the last month has been pretty big. I have some pretty hard coded things around money and how I spend my time that I’m trying to rewire now to grow into someone who apparently has a company that was backed by an investor, and not just an investor, but TinySeed, who I really admire and respect. And so it’s like, oh, I kind of need to become this thing that I am on paper, and that’s how I spend my time during the day. It’s like hiring more help, hiring a landscaper, for example, to help mow the lawn. I take pride in, yeah, I’m mow my lawn, I’m happy to do things and work on things. I don’t have everything done for me. But it’s like, yeah, okay, if you can find someone to do that for 40 bucks, should you be doing it?
Does it make sense for you to be doing it? And I mean, when I started my career, I mean, I remember in the very, very early days, my first job was an unpaid internship, cold calling 2009 in the recession. And my first job, I would skip lunch just to save money. And so I have certain things with money where I need to kind of think bigger and pursue the bigger opportunity. And it is pretty intense. It’s really rewiring stuff that’s pretty deep seated. And so I feel like if I can’t do that, if this doesn’t work, it’ll be because I couldn’t figure those things out. I couldn’t get past my own stuff. I think that the market opportunity is there. I keep having better and better calls. I’m having very interesting opportunities. Our MRR keeps growing. We passed 10 k and MRR in nine months, and really smart people are liking it, what we’re doing.
And so that is the thing that I, and so it’s exciting in a way. I feel like I’m progressing and growing and getting better as a person and more well-rounded. And if I can have more capacity to do these things, it’ll benefit everything I’m trying to do in my life. But yeah, it’s like, yeah, but I have to do it faster than it’s a real forcing function of, Hey, it’s time now to do that, to make these changes, to become this version of this company and this version of myself. So yeah, that’s the hardest thing. And this feeling of pressure of if I can’t figure it out, that’s what I’m feeling right now. It’s like now there will be a stage at which something will happen where I’m like, Hey, I couldn’t control that. That was because of external forces or whatever. But yeah, right now it’s that pressure.
Overall, it’s good. I want to be there. Pressure’s a good thing. Pressure’s a privilege. It’s good to be in the seat that I’m in. I would trade it, but it’s different than before when it was always like a side bet and well, if it doesn’t work, I can always do something different. And there’s comfort in the way I was doing things, but it wasn’t compounding. I wasn’t building assets. I wasn’t building wealth. I wasn’t really moving forward. It was just like, I’m flexible and I’m kg and I’m making it work, but if I want to be build something, then I have to make these changes. So yeah, it’s definitely that. Not to turn this into a therapy session, but that’s definitely the thing right now for sure, for me.
Rob Walling:
And on the flip side, what is going well? What is working? What are you excited about? What gets you up in the morning?
Harris Kenny:
It’s definitely the things that we’re enabling customers to do. I feel like we’re actually very far ahead of our users and our users are very far ahead of the market. So because the way our product works is very different than the way that most of these native integrations work in the market and the way that most teams are doing things these days. So I’m excited because we’re working on stuff that’s really on the edge. And I’ll have a conversation once a week with somebody who sees that and they’re like, okay, well, here’s how I want to apply this to doing cold calling, or here’s how I want to do a data enrichment workflow based on what you just showed me that outbounding can do. So that’s exciting. I feel like if I can enable those kind of people, that the one to three year horizon for the company is really exciting.
Because right now we’re in a niche of a niche of a niche. I mean, it’s a really small part of the market who gets what we do? And then even within that, there’s only certain people where I get on calls and they’re like, oh my God, yes, this is it. So those conversations are super motivating. So we’ve got some features that we’re working on that I think are going to pay off in that way that I’m excited about. And then some bigger companies, for sure that are talking to us, I mean, there’s partnerships that we’re doing with agencies that are going very well. There’s this broader conversation of what other integration work? Could we do other platforms? That’s kind of interesting. But yeah, I think in general it’s like I feel like we’re ahead and people who are ahead are finding us and getting excited. And that makes me think that there’s a solid future here, because I’ve seen the stuff that I was doing on my agency a few years ago that are now mainstream two or three years later, and the companies that are supporting that are literally growing 10 x. And so I think that if I’m ahead, I think we’re ahead then the future is really exciting. And even now the growth is good, but I think it could be a lot better. And so that’s exciting. I think
Rob Walling:
Harris seems to have caught a bit of lightning in a bottle as he moves forward. He’ll have some big decisions to make. Should he add support for additional platforms, double down on a narrower ICP, or widen the aperture and go for a broader market or go after something else entirely. That’s next time on tiny Seat Tails. Hope you enjoyed this episode. If you’ve ever wondered what it’s really like inside TinySeed and want to hear a raw candid coaching conversation between Harris and I, we put together something special for you at TinySeed dot com slash bonus. You should check it out. I’ve never released anything like this before. I hope you enjoy it. It’s at TinySeed dot com slash bonus.
Is this really an episode of Startups For the Rest Of Us on a Thursday? That’s right. For the next six weeks, you’ll find new episodes of TinySeed Tales Season five in this feed every Thursday morning. If you’re not familiar with TinySeed Tales, it’s a narrative style season based show where I follow a founder. As they navigate the ups and downs of building a SaaS, we dive into their journey to find product-market fit, optimize the product, scale their business, and hopefully reach escape velocity. These episodes were recorded over the past year, so you’re going to get an inside look at a founder’s journey. The goal is to give you honest insights into the challenges, setbacks, and hard won victories that come with growing a real SaaS company. If you’re new to TinySeed, it’s the startup accelerator I run for ambitious bootstrapped SaaS founders, and it’s the first accelerator of its kind Twice a year, we fund B2B SaaS founders who want just the right amount of capital, a community of like-minded, ambitious founders and access to mentorship advice and everything else you’d expect from a world-class accelerator applications for our fall 2025 batch open on September 1st.
This time around, we’ve shortened the application window a bit and we’ve tightened up the process, so we’ll get you a definitive answer much quicker. Avoiding the drawn out uncertainty common in other investment processes. The application is intentionally short and focused, and if you know your core metrics, it usually takes about 10 to 15 minutes to complete for all the details and to get notified when applications open, go to tiny c.com/apply and get on our mailing list. Let’s dive into this first episode of season five.
Harris Kenny:
My name is Harris Kenny, I’m the founder of Outbound Sync, and it’s an integration product between sales engagement platforms and CRMs.
Rob Walling:
Welcome back to Tiny Sea Tales, a series where I follow a founder through the rollercoaster of building their startup. I’m your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the first startup accelerator designed for Bootstrappers. This will be our first episode of season five where we follow Harris Kenny, founder of Outbound Sync. Harris has made the hard transition from agency owner to SaaS founder, and in just over a year has built his monthly recurring revenue to $10,000 a month. In my first conversation with Harris, I asked him why he applied to TinySeed in the first place.
Harris Kenny:
My SaaS product is built out of my agency, and it was the fourth iteration of a SaaS that I tried over a total of five years working myself. What really pushed me was that it felt like it was starting to really take off. I was feeling that the rocket is entering the atmosphere and it’s shaking and the bolts are moving. I was getting more deals coming in and bigger and bigger prospects and very mature companies saying, Hey, yeah, we’re interested in this. Here’s a security questionnaire and these things. It just started compounding and actually someone reached out to me who’s a TinySeed portfolio company, and he was like, Hey, you should think about applying to TinySeed, and I was like, oh, actually, it’s funny. It’s a long story. I’ve been following TinySeed for years and I kind of forgot about it to go into building mode, but now that I’m here and this is working, maybe I should throw my hat in, and so reached out to a couple of TinySeed founders. But yeah, it was that feeling of like, Hey, what if this works actually, and that was exciting, but also I don’t know that I want to do this alone basically.
Rob Walling:
That’s a good way to think about
Harris Kenny:
It. Not fear of success, but oh, this seems like it could actually work, so it’s like I should not get in my own way being alone. Yeah. If I’m alone, I feel like my odds of success are higher with TinySeed, basically. That was why I should try, but if it didn’t work, I was going to do it anyway.
Rob Walling:
Some of the challenges of being a solopreneur are obvious, the loneliness, the isolation, no one to spitball ideas with, but then there’s also this very practical human need to succeed if for no other reason than to support your family.
Harris Kenny:
I started my own company five years ago before my wife and I had kids because I wanted to have the flexibility and I was always able to in services, it’s very flexible. I was always able to pull a rabbit out of a hat and make it work, and we have great house, we’re very fortunate, but with SaaS, it was kind of like, okay, it is time for me to take this more seriously. When we got this new house, the process of getting a mortgage was so frustrating of how I paid myself through my own company and it’s like, okay, it’s time for me to grow up a little bit, and if I’m going to run that kind of company, I’ve known how to make it work kind of like a street rat, like Aladdin or whatever, but it’s like, okay, now I’m kind of entering a different world where there’s due diligence and process and uptime and you can’t just make up for it with a smile and working extra on a Saturday. It’s like if that thing is down, it’s down and you messed up and it’s a huge problem. So it was all of that, but also the upside of it’s like the best business model ever, and if I could be the one running that kind of business, the reward is pretty substantial and it’s really leveraged work. I solve a problem once and I sell it X times versus one and over one over,
Rob Walling:
And also it’s recurring.
Harris Kenny:
Yes.
Rob Walling:
Let’s say you went and raised friends and family or you raised an angel round and you hustled and you got money that wouldn’t replace the community, the mentorship, the connection, but there are other programs certainly out there. There are funds that have communities or there are accelerator regional accelerators. There are other options, and I’m curious if you evaluated those or for you, why TinySeed over the alternatives?
Harris Kenny:
Yeah, I think that TinySeed, it was definitely an end of one when I got to this point because MicroConf community, this is going back to 2020, kind of started me down this road and start small, say small, and the stair stepping method, those ideas were very early on. It was small dominoes that started, but it took a while for the dominoes to get bigger basically. And so it kind of shaped in my mind how I was thinking about what I wanted a business to do for me, for my life, for my family, and then I went through this circuitous route. So I think that’s part of it. It was very early influence in terms of setting what’s possible. In my mind, it’s like it doesn’t have to be a billion dollar company to be successful. There’s actually many, in fact, hundreds of millions of different little price points between zero and a billion that would be really successful.
So I think that’s part of it. And then it was sort of wandering through the desert, trying a lot of ideas, trying to run the agency slowly getting better. I mean, we had some good months. I mean, I had some agency months where we were over 30 K in build services. Good. It was a good agency, but as the SaaS part started growing and that MRR kept growing relative to the agency side, it was like, no, I really wanted to build a B2B SaaS company. I don’t want to build a productized service. I don’t want to have some goofy combination of things like multiple bets, a little app here, a little app there. I want to build a single B2B SaaS company that solves a really specific problem and that moves up market and that can solve enterprise level, really highly complex issues of what we do are on block lists and syncing data.
It actually gets pretty thorny, and we’re in a really, really small area, and so it’s just like, I’m going to need more power firepower like my team and I want to build a B2B SaaS company. That was it. And the other ones I talked to that I looked at over the years were like, well, we’ll invest in this, but also this. And also their thesis was so scattered that it was kind of like, I don’t really want that and I want somebody who’s going to be like, Hey, let’s talk about churn for two hours and we want to talk about it, and you want to talk about it. And by the way, you have 12 friends who are all similar spot who also want to talk about it. That was what I wanted, not just a general panel about how do you keep your customers happy. It’s like, no, no, I very specifically want to solve this churn problem.
Rob Walling:
Yeah, no, and that makes a lot of sense, and that is how my career as a professional has evolved because if you go back to MicroConf in 2011, it was the conference for self-funded startups. It was not SaaS, and it wasn’t until really 20 15, 14, somewhere in there where I was like, oh, SaaS is where I want to be, and the deeper I go, the more value that I can provide, and by deeper I go, I meant startup For the Rest Of Us went all SaaS at that point, and I just told people I’m not answering questions about info products anymore. It’s not that I don’t like info products. It’s not that I don’t make info products. I have courses, I have books. Everything I do on the MicroConf side is kind a course information product. It’s not that I don’t like those, it’s that I can’t help you as much if I’m not focused.
It’s why my books now, I have wrote a book called The SaaS Playbook. It’s not the Startup Playbook because for exactly what you’re saying is the moment that you rise up one layer of abstraction, you lose granularity and two hours on churn makes no sense. If there’s a biotech company next to you and a hardware company on the other side and a two-sided marketplace on the other side and a B2C company on the other side of you, you don’t share that same depth. And I was concerned early on about pigeonholing, and frankly when we launched TinySeed a and r, my co-founder, for folks who were listening Cog, he was like, it’s b2, B Cs, that’s what we’re doing. I was like, but maybe what if I’m the person who was like, but we could and I think it’s the best decision we made
Harris Kenny:
Looking at our batch. It’s like these companies are structurally similar in the important ways, but so different. And it’s amazing how much you can learn when real estate titles is one of our batch companies and Go links, but then you hear ’em talking and you’re like, oh, actually no, this is totally relevant. Even though if you talk to a normal person, they would be like, those are three different companies,
Rob Walling:
But a lot of commonality,
Harris Kenny:
So I can see how, and you learn from that. So yeah, it’s just a very specific way to operate. But within that, I think there’s a lot of variety.
Rob Walling:
Well, and it speaks to secretly slash not so secretly, what do any of us want to do? We want to operate a company that is probably best in class, and I want my companies to always be the gold standard. So I want Drip to be the best at what it did, and I want people to think highly of it, and I want MicroComp to be the gold standard for bootstrapped entrepreneurs, and I want TinySeed to be the gold standard for B2B SaaS accelerators, period. I want to be the best in the world, otherwise why am I doing it? And it speaks to that’s a long road. You have to build a brand, you have to do all this stuff, but it speaks to that it was a factor for you of, oh, well, I’m B2B SaaS and therefore I want the best that I know. I dunno, I guess that means a lot. I normally on tiny sea tails, I’m not the one kind of having a realization, but every time I hear that kind of thing of why did you apply? And it’s like, well, your B2B SaaS and so am I. It’s like we made the right decision. You know what I mean? Going narrow is often often the right decision.
Harris Kenny:
Yeah, well, I mean especially at that point, because at that point our MRR was, I mean this is April, it was like 7,000 or something like that. And I still had mean in May, this was my last full month of the agency, we did $30,000 in revenue, but then almost a third of that was the SaaS. So I was getting basically my time. I was really busy then, and then I had these big customers who were paying me big amounts and the SaaS was getting close. I was like, I don’t probably don’t need to do this. But when I talked about it with my wife, she was really encouraging of, this is the thing that you’ve been wanting, you should go for it. Don’t go halfway. And I will say two months out from that decision, just speaking about the point about focus, these two months of the SaaS now really taking off and then the agency petering out and slowly winding down.
It has been so much work running both. And during the process, I remember Tracy was like, look, you run your company, but just so you know, if you’re working on it, we want it to be the thing that you’re working on. We don’t want you to have seven other things going on. Which I was like, okay, I get it. Okay, no problem. But two months of having both is like I literally, I don’t know if I could do this for another month or two because, and so I’ve seen this relief, but also I’m having much better ideas and I’m having, we can talk about the go-to-market stuff, but that is starting to really, really accelerate. And I’m also seeing with my team, our developer, he was part-time before and then once joining TinySeed, I could say, Hey, you’re 40 hours now. And oh my gosh, he’s just ripping and I’ve got a funny story from the kickoff about that, but he’s just ripping through tickets.
And this is kind of goofy, but personal example. We have a nanny who he hired and we’ve had this mix mishmash of daycare in the past, but having a full-time nanny who she’s really good and she’s like, this is what I do. I take care of kids and I help you help your family. She’s helping her in the house and she’s doing laundry and she’s cleaning and she’s so playful with the kids and she’s coming up with these activities and it’s so different than when we had a part-time nanny and then a grandma here and then spend time with a neighbor there. So there’s this whole deeper thing that I’m kind of processing about focus energy and what are you doing, whether it’s our developer or a nanny or me having one company, and it seems so obvious, but it’s just slowly permeating my whole brain.
Rob Walling:
I’ve learned through personal experience that when you try to run multiple companies at once, all of them suffer and so does your personal life. That’s why we require any founder we invest in to fully commit to their idea. That’s what I told Harris when he applied to be part of TinySeed, and he was skeptical at first, but ultimately he came around
Harris Kenny:
When I said, okay. I thought it was like, okay, this is kind of not a concession, but a little bit of a concession. But of what I’ve come to realize is that it has actually, I think benefited me disproportionately because I own most of my company, almost all of it still. And so my company’s doing better, so I benefit way more. And my personal life, my whole thinking on that has flipped. I mean, I wasn’t salty about it before, but I was kind of like, okay, this is a choice. I’m giving something up here, but I feel like I’ve just been freed to just build this thing that after spending all this time years trying ideas and posting and getting feedback, I finally have this idea that really smart people are like, Hey, I want a, so it’s like just do that thing. This is it. Just do it a lot. You
Rob Walling:
Have caught a tiger by the tail, lightning in a bottle, whatever analogy we can use for it. And it’s like, don’t that up by half-assing it because someone will eat your lunch. This is what would happen if you worked on this and three other things is it would grow slow. You wouldn’t give a full attention. You’d be distracted when you’re doing dishes, when you’re walking around, when you’re in the shower, whatever. All your thoughts are scattered between three and four things. It doesn’t get the attention it deserves. It’s not even the hours, as you said, you have best ideas when you’re focused and your best ideas are what’s going to 10 x this business? It’s not the split
Harris Kenny:
Focus. There are two agencies who had been working on a similar thing, and I’m seeing us separate. I’m seeing us getting mentioned organically in other places, and I’m seeing us getting referrals like, oh, that’s Harris’s thing that, oh, outbound sync. That’s all they do. Even though those other agency owners, by the way, are super smart and I know that they’ve built really good integrations that are working for their individual customers, but they’re also doing their thought leadership posts and they’re also trying to get known for other things. And so I’m seeing that play out right now. What could be a direct competitor versus a Zapier make or something?
Rob Walling:
I want to touch on something you’ve already brought up, which is you had an agency doing outbound for paid clients, and as you said, you built it to 30 grand a month and you launched a successful SaaS out of that agency. The thing with building a SaaS out of an agency is every agency wants to do it. Some agencies try and almost none succeed. It’s very, very hard to be running agency or consultancy managing clients. You have freelancers or full-time people doing day-to-day work. It’s like, I got to give 40 hours of work in just for the clients that I’m trying to do the SaaS on the side. Is it nights and weekends or am I not taking paying work to do this thing that is not paying me or may never pay me? And that’s the balance, right, is if I can bill a hundred dollars, $200 an hour, whatever it is, thousands of dollars a month, why wouldn’t I just do that? Then actually focus on the thing that might bring me thousands of dollars a month, a year or two down the line? My question for you is how did you do it? When most fail, why have you succeeded?
Harris Kenny:
I think the first thing I would say that I feel is that where I am right now is that this is kind of the getting into TinySeed, winding down, the agency starting this ass is kind of the end of the beginning. And so I see the early development of the project is kind of prologue, and obviously there’s a lot of work to be done from here, but how did I get from prologue to here? I think I just really, really, really wanted it. I really wanted to have this kind of company seeing other SaaS founders who kind of got to later stages and what their life looked like. And it was just like, I want that. I want to be around. It’s really important to me to spend as much time as I can with my kids, but also have resources so that they can do cool things and travel.
My wife and I love to travel, so I think that I really wanted the outcome and this idea I stumbled on by accident. I had a customer who basically wanted this product. They were right for the wrong reasons, they were too small to need it versus what I’m seeing who actually needs it these days. But I built it just because I felt like I could, and frankly, I wouldn’t be here if I didn’t have Chad GPT because I built the first version of this with Chad, GPT, and I thought it was like, I saw there’s this funny quote of we do hard things, not because they’re hard, but because we thought they would be easy. And that’s how I ended up here. I was like, oh, I can do that a make.com scenario, no problem. And then I use chat GPT, I just need one API call and I can do everything else in make.
And then I posted on LinkedIn and more people were interested. And so I started bundling with my campaigns and I started saying, Hey, if you want to do outbound with us, you have to be using HubSpot and we use our integration. And so it was kind of forced coupling of the two products. And then if the product was falling short, I could always make up for it on the services side. And then slowly I started to have people say, well, we don’t want to do campaigns with you, but that sync thing sounds cool. Can we just have that? And so then I sold a couple of those and that was the first time I felt like, oh, I have actual SaaS revenue here. They’re just paying me for a product and I haven’t talked to them in a month. And I checked in with them.
Service anxiety was like, Hey, how’s everything going? And they’re like, yeah, man, great. What’s up? Why are you emailing me? I was like, oh, have a good day. Alright, see you. Good to hear. Let know if you need anything. So that was how I think stepped into it. I did a trade with a development shop, running campaigns for them, and then they refactored the code from low-code to code. So it took four months of low code, two months of refactoring to real code, and then that’s when things really started. So I kind of count our MRR in October when it was running through the real platform and I wasn’t manually connecting make scenarios and stuff like that. The product was just so bad then that it really didn’t count. So yeah, that’s kind of technically how I do it, but it was nights and weekends and it was weird hours.
There’s one story that I just like, I’ll remember this for my entire life. So we had also had some really intense family medical stuff. That’s a conversation with our day. And then my health also, it’s been hard to be healthy. I’ve not had the best lifestyle, losing a lot, not a lot of sleep, not great food, not great exercise. So it’s been very difficult. It’s required a lot of different sacrifices that I’m trying to correct a little bit now. It was three 30 in the morning in Denver, one of these early customers who said they wanted it. I connected it through make this guy’s in Warsaw, he’s in Poland, and I’m messaging him on Slack. I’m like, Hey, I fixed that bug. He’s like, okay, great. I was like, do you want to talk about it? I just want to make sure that it’s working.
He was like, now, right now, aren’t you in Denver? I was like, yeah, I’m awake. Are you free? Let’s talk. And so we hopped on a slide huddle and we talked for 10 minutes and he was like three 30 in the morning and he was like, are you okay? I’m like, yeah, yeah, I’ve just been working on this for five hours. I’m not doing any kind of drugs or anything. I’m just working on this for five hours and I need to hear from you that it’s working so I can go to bed head. And he was like, you’re a zombie. I was like, I dunno, I just really want to solve this right now and then I’m going to go to sleep. And so not being a developer, there were times where things were probably way harder. Like GPT isn’t actually that good at writing code, but it was like sacrifices like that, being lucky, having good support, a lot of other things. But yeah, that’s my reflection on that stage.
Rob Walling:
I like that and I want to tease it out. I often say success is three components of varying degrees. It depends on the story. The components are hard work, luck and skill. And the hard work is you doing what it takes and staying up till three 30 morning than doing it. I’m not saying that neither you or I agreeing you should do that every night, nor is it healthy. But sometimes there are points where you have to do this, you have to do the work, you have to schlep, you have to be the janitor or you have to pull an all-nighter to do a thing or work a 60 hour week here and there, not for the rest of your life to make it work. So the hard work is obvious, the luck, I think there’s a bit of luck that you stumbled upon an idea that was an obvious need from the start.
And this is where it’s like, is it luck or did you make your own luck by starting an agency, by developing the skillset that you have as someone who can sell, as someone who found clients, and as someone who put in the work to build an agency to 30 K to then create opportunity for yourself. So I say doing things in public creates opportunity and by in public sometimes that’s a blog. Sometimes that’s starting a company and then realizing, oh, there’s actually a deeper need here. So all of these factors are at play in your story. And there’s an element too of, I guess we could put it in the skill bucket, but it’s like you were smart enough to realize, oh, this need for this customer is something that I should build in no code, or I should build a code, frankly. But you didn’t have the skill at the time. And so it’s like there’s a scrappiness to this story of just kind figured it out, went, did G PT and wired it together with make, I know some founders or aspiring founders who just wouldn’t, they wouldn’t take action. They wouldn’t do, is it too risky? Am I wasting the time? What if this doesn’t work? What if it breaks and the client gets mad at me? What? And it sounds like you took a lot of action very quickly because all of it doesn’t have to work just 70 or 80% of it does, right?
Harris Kenny:
Yeah. Yep. Yeah. I mean, my threshold was can I get this working well enough that I can with a straight face talk about it on LinkedIn and I mean WhatsApp groups and Slack groups with some outbound folks too, and share it and see if people are interested enough for me to keep working on it. So that was my threshold. I never misrepresented where the product was, but I would literally finish something and then be recording a video of three minutes later being like, look at what Aon sync can do Now. There was no one month leadup. If we’re releasing something new, it’s like literally, I just finished this. It’s worked one time. I’m going to talk about it.
Rob Walling:
And that we see this with the most successful TinySeed founders. I have a list of all the seven figure TinySeed companies in a simple note doc on my phone. And if you go down that list and you look at the founders, guess what all of them do? They all move very quickly. They ship things very quickly, and they generally work on the right things. They’re not right all the time, but they’re right enough at the time. You don’t need to be right a hundred percent if you’re right, 60, 70, 80%, but you’re just shipping a lot of things quickly. You hit it. It all doesn’t have to work at this point. It’s cliche to refer to the entrepreneurial journey as a roller rollercoaster, but it’s not inaccurate because there are challenges, fear and times when nothing’s working. But there’s also optimism, things that excite you, moments where everything comes together. I was curious to find out what was keeping Harris up at night? What kind of headwinds was he facing?
Harris Kenny:
It is definitely myself still. There’s the mindset shift that I’ve been trying to undergo in the last month has been pretty big. I have some pretty hard coded things around money and how I spend my time that I’m trying to rewire now to grow into someone who apparently has a company that was backed by an investor, and not just an investor, but TinySeed, who I really admire and respect. And so it’s like, oh, I kind of need to become this thing that I am on paper, and that’s how I spend my time during the day. It’s like hiring more help, hiring a landscaper, for example, to help mow the lawn. I take pride in, yeah, I’m mow my lawn, I’m happy to do things and work on things. I don’t have everything done for me. But it’s like, yeah, okay, if you can find someone to do that for 40 bucks, should you be doing it?
Does it make sense for you to be doing it? And I mean, when I started my career, I mean, I remember in the very, very early days, my first job was an unpaid internship, cold calling 2009 in the recession. And my first job, I would skip lunch just to save money. And so I have certain things with money where I need to kind of think bigger and pursue the bigger opportunity. And it is pretty intense. It’s really rewiring stuff that’s pretty deep seated. And so I feel like if I can’t do that, if this doesn’t work, it’ll be because I couldn’t figure those things out. I couldn’t get past my own stuff. I think that the market opportunity is there. I keep having better and better calls. I’m having very interesting opportunities. Our MRR keeps growing. We passed 10 k and MRR in nine months, and really smart people are liking it, what we’re doing.
And so that is the thing that I, and so it’s exciting in a way. I feel like I’m progressing and growing and getting better as a person and more well-rounded. And if I can have more capacity to do these things, it’ll benefit everything I’m trying to do in my life. But yeah, it’s like, yeah, but I have to do it faster than it’s a real forcing function of, Hey, it’s time now to do that, to make these changes, to become this version of this company and this version of myself. So yeah, that’s the hardest thing. And this feeling of pressure of if I can’t figure it out, that’s what I’m feeling right now. It’s like now there will be a stage at which something will happen where I’m like, Hey, I couldn’t control that. That was because of external forces or whatever. But yeah, right now it’s that pressure.
Overall, it’s good. I want to be there. Pressure’s a good thing. Pressure’s a privilege. It’s good to be in the seat that I’m in. I would trade it, but it’s different than before when it was always like a side bet and well, if it doesn’t work, I can always do something different. And there’s comfort in the way I was doing things, but it wasn’t compounding. I wasn’t building assets. I wasn’t building wealth. I wasn’t really moving forward. It was just like, I’m flexible and I’m kg and I’m making it work, but if I want to be build something, then I have to make these changes. So yeah, it’s definitely that. Not to turn this into a therapy session, but that’s definitely the thing right now for sure, for me.
Rob Walling:
And on the flip side, what is going well? What is working? What are you excited about? What gets you up in the morning?
Harris Kenny:
It’s definitely the things that we’re enabling customers to do. I feel like we’re actually very far ahead of our users and our users are very far ahead of the market. So because the way our product works is very different than the way that most of these native integrations work in the market and the way that most teams are doing things these days. So I’m excited because we’re working on stuff that’s really on the edge. And I’ll have a conversation once a week with somebody who sees that and they’re like, okay, well, here’s how I want to apply this to doing cold calling, or here’s how I want to do a data enrichment workflow based on what you just showed me that outbounding can do. So that’s exciting. I feel like if I can enable those kind of people, that the one to three year horizon for the company is really exciting.
Because right now we’re in a niche of a niche of a niche. I mean, it’s a really small part of the market who gets what we do? And then even within that, there’s only certain people where I get on calls and they’re like, oh my God, yes, this is it. So those conversations are super motivating. So we’ve got some features that we’re working on that I think are going to pay off in that way that I’m excited about. And then some bigger companies, for sure that are talking to us, I mean, there’s partnerships that we’re doing with agencies that are going very well. There’s this broader conversation of what other integration work? Could we do other platforms? That’s kind of interesting. But yeah, I think in general it’s like I feel like we’re ahead and people who are ahead are finding us and getting excited. And that makes me think that there’s a solid future here, because I’ve seen the stuff that I was doing on my agency a few years ago that are now mainstream two or three years later, and the companies that are supporting that are literally growing 10 x. And so I think that if I’m ahead, I think we’re ahead then the future is really exciting. And even now the growth is good, but I think it could be a lot better. And so that’s exciting. I think
Rob Walling:
Harris seems to have caught a bit of lightning in a bottle as he moves forward. He’ll have some big decisions to make. Should he add support for additional platforms, double down on a narrower ICP, or widen the aperture and go for a broader market or go after something else entirely. That’s next time on tiny Seat Tails. Hope you enjoyed this episode. If you’ve ever wondered what it’s really like inside TinySeed and want to hear a raw candid coaching conversation between Harris and I, we put together something special for you at TinySeed dot com slash bonus. You should check it out. I’ve never released anything like this before. I hope you enjoy it. It’s at TinySeed dot com slash bonus.
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