Episode 799 | TinySeed Tales s5e6: $500k ARR!

Rob Walling:
It’s the sixth and final episode of TinySeed Tales season five, where we’ve followed Harris Kenny’s journey as he’s had incredible results growing outbound sink. If you’re interested in investing in founders like Harris and diversifying your portfolio away from public markets or wherever you might have that money parked, you can join TinySeed Fund three to invest in early stage bootstrapped B2B SaaS companies. To learn more about our thesis, you can add to TinySeed dot com slash invest, and if you fill out the form on that page, it goes directly to a r, my co-founders inbox. If you want to keep up with everything we’re doing at TinySeed, head to TinySeed dot com and drop your email in the footer. I promise we will not spam you. We only send occasional updates about what’s going on in the world of ambitious, mostly bootstrap founders. Let’s dive into this sixth and final episode of this season.  

Harris Kenny:
There’s a light at the end of the tunnel, which I haven’t felt for a long time. If anything, it felt like the light was getting dimmer. I was on a little train thing, but the train was on a hill and it was rolling backwards, so now I found the hand crank and I’m like kind of cranking towards the light.  

Rob Walling:
Welcome back to TinySeed Tails. This is the final episode of season five, and we’re following Harris Kenney’s journey from agency owner to SaaS founder. When we started this series, Harris was juggling his agency while building outbound sync. Over five episodes, we’ve watched him go all in, navigate the ups and downs of early growth, achieve profitability, and faced the tough decisions that come with success. In our last episode, he was about to take off on a vacation where he was planning to mull over the decision on whether or not he should raise an additional round, so I wanted to check up on him to see how it went. So Harris, it’s been about 12 weeks since we last chatted. Bring us up to speed on where the business is at and whether you took a really nice vacation over the summer or whether you’ve been hitting the gas.  

Harris Kenny:
So yes, took a nice vacation but was not restful vacation in terms of we traveled to Europe with two children under five, did a lot more intense hiking. I liked to hike and I loved being in the mountains, but I don’t think I was fully prepared for the physical amount of effort that was going to go on that trip. So it wasn’t restful, but it was time away and I was able to take the closest to a vacation that I’ve been able to take since I started working myself in 2019. So that was cool. Feeling the difference of having a SaaS company versus having a consultancy or an agency. I just worked 30 minutes or something like that, a day. I used it to kickstart some things, but the good news is that the business is going. And then I’ve also made some personal health changes as well since then. 

So we passed that 500 KARR. We’re actually well past that now at the time that we’re talking right now. So we kind of blew through that pretty quickly, so we hit that big number. And then personally, I’ve also made a huge change for my own health. So I used the trip and the time zone adjustment to, I started exercising early in the mornings, so I’ve been getting up at like four 30 is my alarm time, which is early and it’s required me to go to bed earlier. And I’m not saying everybody should do this, but for me, I’ve been doing that. And so I’ve worked out, this is like 81 days in a row now, no days off now. I will do more relaxed days sometimes, or sometimes I will. I hit snooze a couple of times, but every day I get up and then I’m trying to just eat better. I have really sick kind of simple rules because in the past I’ve yo-yo a little bit over the last years of this journey and I simplified it a lot and I’m not measuring tons of things. I’m not going sort of over the top of it. And anyway, that’s going really, really well. So I’ve lost quite a bit of weight and I’m just a feeling much, much better. So anyway, a lot has changed in the last few months, but it’s more of the same just sinking data, working with agencies and growing the thing.  

Rob Walling:
Well, and more of the same. Is growth really been the theme for this season of TinySeed Tails is that you have grown the out of this business man, and it’s like, Hey, I am super happy for you. In terms of the physical health, I know that’s something you had brought up earlier in this season, having concerns about it and it’s hard balance to do that and requires a lot of discipline to give that some time when you have a spouse and two young kids and a startup that kind of takes a lot of your attention. And B, I’m stoked over the moon for you to have passed 500 KARR. I mean, it’s obviously pretty incredible growth from where we started. How does it feel to you looking back and how does it feel to you today to think? I bet two, three years ago you thought, man, if someday I could ever have a SaaS that did 20 KA month, 30 KA month, you have these numbers in your head and I’m wondering if you’re past all those numbers that you dreamed about at one point.  

Harris Kenny:
Honestly, it feels really good. I mean, I’m really proud of the company right now. I think I got a few big things and have worked really hard and I’ve gotten a little lucky too. But it feels great when I think about our customers and when I think about our agency partners, I really feel like we are building something together and people are changing how they work. And my company and app on sync is part of that. And so it’s cool to be on the winning side of that. I spent years helping other people grow their companies trying to running campaigns, doing these other things, and I think that the thing that I’ve realized the most that it was those big directional things that I got right early, explain a lot of the growth here. I’m not spending time optimizing a landing page. I’m not sweating over the pricing this or that. 

I’m not chasing down if there’s a missed payment, I’m not going and chasing that payment back. I’ll just kind of let a lot of little things slide that I think in the past I’ve thought about, or even when I was working with clients trying to help them like, Hey, okay, well, let’s optimize a little bit here or there. So yeah, it feels good, and I think it’s because of a few big things and a few working hard and a few lucky breaks and stuff like that that it’s kind of come together. But I mean, this is totally my best of all possible worlds, but this is kind of where I think I could have hoped to have landed and where we’re going next, this next chapter, I think I actually think we are going to potentially start growing faster soon because of some of the stuff we’re working on. So yeah, I’m really grateful for where we are today for sure.  

Rob Walling:
As part of that growth, Harris was eyeing conferences as his next marketing channel, but he wasn’t interested in boring hotel, happy hours. He wanted to do something that would get the entire industry talking.  

Harris Kenny:
I’ve been trying to let myself have fun a little bit because everything is very stodgy and everyone takes themselves very seriously, especially in this enterprise sales go to market space. And so I’ve just been kind of posting funny, or at least what I think is funny stuff on LinkedIn, and we had this decision of what do we do with events? Travel is really tough because my family stuff at this point, it’s really tough to leave the house for multiple days at a time, let alone multiple trips a year. And our budget and the company’s budget’s tight. So I was like, I’m going to pick one event this fall, and in sales tech B2B SaaS, it’s like September, October, that’s kind of event season. And in the past I’d gone to Inbound, which is Hotspot’s big conference. I thought about going to Dreamforce, which is obviously Salesforce’s big conference, but Clay, there was a wind of clay having an event. 

And so I started planning months in advance that we were going to do something around Clay’s event, and I was talking with our agency buddies and anyway, kind of landed on this idea of doing laser tag. And people were like, oh my God, that’s awesome. That’s awesome. Is the word that kept coming up, or if you did that, I would totally go. And I was like, oh, okay. So if we really focus on this ICP, and if we focus on we help winners win and we can do things differently. We don’t have to follow the same rules as everybody else. We don’t have to actually do a boring happy hour at a hotel restaurant next to the venue, which is fine that people do that, whatever, but we don’t have to do that. And so I said, let’s do it. So I talked to a few of our partners and I said, listen, we’re doing laser tag, it’s going to be awesome. 

I’m covering the venue and this is a flat fee that we’re going to charge per sponsor. We need buses. And I got two companies to sign up for buses for charter buses, and then Word got out and then another company signed up for lunch. And so then I was like, okay, we’ve got a venue 5,000 square foot venue outside of San Francisco. We’ve got two buses, we’ve got lunch covered. Now I need to start getting some of our top people excited. And so they were like, okay, we’re in. We’re coming. I’ll be. So then I used them to get other people into it. And anyway, it sort of snowballed. Now we’ve got, I think probably 90 people RSVP’d to come to a laser tag venue the day before Clay’s event. More and more sponsors kept kind of wanting to get involved. So we’re going to have a 360 degree photo booth, we’re going to have a professional photographer, videographer, we’re going to have trophies. 

I mean, it has gotten totally out of control. It has made me so much appreciate Sonia at MicroConf and what she does. It has been so much work, but I’ve been happy to do it because everybody is so excited about it. And it’s a very elite group. It’s invite only, we haven’t posted it publicly. Anybody can’t just sign up. And so it’s kind of an if you know thing, and it feels like it’s really consistent with the product we’re trying to build. It’s for experts, it’s for people who know what they’re doing. And this is an event where you can be with other people like that and just having such a blast with it and it’s going to be kind of a hot ticket event. So yeah, I’m jazzed about laser tag. Hopefully nobody tears their ACL or something like that, but I think it’s going to be great. 

And I helped a few people get visas approved. So we’re going to have people coming from the Philippines, from Macedonia, I mean literally from all over the world are coming for the clay event and also for laser tag. So that’s been all in progress the last few months, but when I decided to commit to the strategy of focus on where things are working, this makes more sense than saying, oh, well now I’m going to make a new landing page and try to convert an extra one person a month or whatever. It just, well, I could be doing that or I could be doing this. And so leaning into the parts of the business that are working are allowing me to have way more fun. So I’m in this stage of the business now where I’m starting to have more fun and kind of do silly things, and that’s a huge emotional relief. It’s been pretty heavy at times, to be honest. Yeah, it’s felt like a labor of love. Definitely.  

Rob Walling:
Yeah. Yeah. Well, I mean, you’ve talked about how financially it has been stressful, and I appreciate that you are taking this time to allow yourself to celebrate it in a way. The laser tech feels to me, it’s just something I have the luxury to do right now. And someone might question whether it’s the optimal business move, as you said, I think it’s a great move for your space and for getting your name out there and for all the reasons, especially since you’re doing enterprise and relational sales. If you were product-led growth and it was like we drive traffic with SEO and then we convert it on the website, it still might be okay, but harder to justify. But I think this is going to reap huge rewards for you, and you get to have fun. It’s designing at a certain point, designing swag. Someone people would rag on whoever Malechi or something. 

It’s like, man, they have a lot of T-shirts. And man, they have those hat, those knit hats, and man, they have a lot of swag, and you know what they earned. Ben Chestnut earned the luxury of being able to do whatever the hell he wanted and that was what he wanted to do. And so in a way, while you’re not at MailChimp level yet, you are at a place where you can take a breath and do maybe a little bit more of what you want and a little less of the grind. And there’s still grind, there’s still grind ahead, but you’re not hand to mouth eight KMRR burning money every month anymore. And so this is a really neat way to be able to celebrate that in a way that fits you. It kind of fits your brand. And in a way, outbound sync is going to reflect who you are as a founder, and all companies should not have the same feel to them. And you get to decide that for yourself.  

Harris Kenny:
I definitely think what you said is right. I’m definitely trying to have fun with it. I’m trying to embrace this, do something that wouldn’t get through a committee. People are like, well, it’s far. How are they going to get there? But enough people are excited about it. I’m like, let’s just try it. It’s so different though. Let’s just try it. Founder mode,  

Rob Walling:
You’re in founder mode, which is just, no, I just do shit. This is what I just get stuff done because I don’t have to ask for permission. That’s what I like about being a founder. When we last spoke, Harris was wrestling with a big decision whether to raise additional funding while the business was thriving two and a half months later. I was curious to see how that played out.  

Harris Kenny:
So there were these external opportunities that were coming in where people were like, I was getting on a call with someone and they would a big platform and they would say, Hey, we’re interested in outing, kind of like as an ipa, we as a big company want to use your pipes, which is different than us selling to a company running their own outbound, but at scale they would have tens of thousands of customers that would use outbound sync infrastructure. And so in my head I’m like, well, that’s going to be really capital intensive, but every single one of those opportunities moved slower or didn’t materialize at all than I thought they would. And then in parallel, we have grown faster than I thought we would. And so everything changed the thing that I was anxious about and then I decided this was probably financially, if you did remember a summit, if you did a probabilistic forecasting model of what is the number of times that you ran this simulation where this was a good idea. 

Maybe most of the time this was a bad idea, but I had decided in June to tell our recruiter to start looking for another engineer, even though our runway was getting shorter and shorter. I said, look, in case everything goes right, I think we might need another engineer just start looking. And it took ’em about two months to find somebody, but they found somebody that they were really excited about. So anyway, brought him on. He’s focusing on B2B social, so a hey reach integration, which is for LinkedIn and for LinkedIn outreach. He’s done great. And we’re now moving that into beta. Basically. We finished that in about a month and it was a huge lift, but because we had the extra firepower, we could do it. And so that was like, well, I thought I needed an investor to potentially more capital to build that out. 

But we got it done in a month and our revenue kept growing naturally. And now when this comes out, I think we’re going to get, I think September is going to be the biggest month we’ve ever had by a lot. When this comes out, we could talk about more about that, but that was a risky, as things were getting a little more stable, I put more chips in anyway because of that combination of factors. Now I’m like, well, I can get more money in from this new channel faster than I can get money in from investors, so I should just do this. This is a guaranteed capital in no equity exchange, not a distraction. And then if I works and we get to seven 50 or something, I can go into those investor conversations with way more confidence and comfort level and have a way different conversation with them and now have just run this experiment of when we added a whole new channel, this is what it did to revenue. It’s not like a never thing, but those are the reasons why I decided not to move forward with that at this time.  

Rob Walling:
Not right now. So I mean, as we were talking about it, you grew revenue to where you now have infinite runway. That means your break even are profitable, and in your case, you’re profitable and you’re still growing. So I’m wondering what new problems have shown up always the next problem in a startup, right? It’s not like that fixes, that was your number one thing is cashflow. Cashflow. There’s personal, there is business, you’re trying to get to 30 5K and you’ve made it. So what else is starting to go wrong, I guess, or what problems have arisen?  

Harris Kenny:
Definitely. So our tech stack didn’t really make sense. It was for a company too big. I sort came to grips with we’re essentially an SB. We were like three people, now four, I’m doing all the growth stuff, all the marketing, all the sales. I was clicking all of these fields in, I don’t want to say which CRM we’re using, but it was just like, this is too much work. Who am I doing this for? Who am I filling these fields out for? Who am I enriching this data for? It’s just me. The hell’s the point. So it was like just trim it down, just trim it, trim it, trim it way, way down, and then pick some more purpose-built tools. So part of what’s been driving this growth is we’ve freed up time because we picked a better support tool that better integrates with Slack because that’s where all of our customers are. 

We picked A CRM that requires way less rules for us to automate things. So that is, I always thought like, oh, we have a tech stack that can scale. Scaling will never be a problem. But the tech stack we had was really for companies at scale. It was not for companies that were at our stage. It was like, I can’t afford to hire a fractional rev ops person to get all this stuff to talk to each other. And so it’s not working. And so it’s taking me 10 minutes to send a stripe link, get the payment back, close the deal, create the onboarding plan. This shouldn’t take 10 minutes, it should take one or it should be automated. So that was a thing that we’ve been ripping stuff out to handle that better. Also, kind of dealing with, I don’t want to say haters, but there’s been some negative interactions with some people. 

Then we got to target on our back a little bit. Right now I’ve got someone scraping every one of my LinkedIn posts and then emailing every single one of those people saying, Hey, we built something that’s better than out bouncing for this, which no harm, no foul, no hard feelings. It’s not personal. But a year ago, nobody cared. And even a year ago somebody did try to smother us in the crib when they requested a demo of app on sync, took the recording, sent it to a developer and said, rebuild this for me for 2000 bucks, which I dunno if I ever talked about this on the show, but we talked about a lot in the TinySeed founder Slack. But that was a whole thing. So I had some threats early on, but now I have, it’s a different nature that has escalated as we’ve gotten more traction, which I didn’t, I dunno, I just didn’t anticipate. I sort of always thought I’m toiling an obscurity here, but then you realize all of a sudden like, oh, we kind of have a brand actually, and that’s the market, but it’s weird when that crossover happens. So that’s been a little unexpected and I think that’s going to get a lot worse.  

Rob Walling:
You’ve heard Harris mention the quote end of the beginning a couple of times this season, so it seems fair to ask now what’s next?  

Harris Kenny:
I know what the next chapter is, and that’s adding this new channel of social B2B social. It’s adding hate reach, it’s changing the company. And I know what the next chapter after this is going to be. It’s going to be adding phones. We had all this uncertainty of other CRMs and we could be doing more with the data. And I feel a lot of conviction. We’re a Salesforce and HubSpot app. That’s what we have built. So we’re a HubSpot app, Salesforce app, if you use one of those CRMs work for you, and now we’re adding these new channels. So that’s definitely the next, finishing this current chapter is adding hey reach, which is social, and then going to be adding dialers phone tools. Haven’t decided which ones yet, but examples would be like Orum or Nooks or Sales Affinity or phone burner, these calling tools because it’s the same problem over and over again. 

And when we add a new channel, the feedback I’m getting from people over the last month is like, dude, this is a totally different product than we talked about a few months ago. I had some kind of slow sales that weren’t converting or whatever because it’s like one plus one is three. I can get data from this channel and from this channel and I can get these two channels to work together. And the combined value of that is much more than just the individual value of each individual channel being in my CRM. And so when we add a third one, one plus one and plus one is five.  

Rob Walling:
Harris has been candid about how the financial stress of building outbound sink was affecting his family life. Now that he’s reached profitability. I’ve wanted to know if that pressure had finally lifted.  

Harris Kenny:
Well, I haven’t been able to change my compensation yet, so no, yes and no. I feel less stressed because I feel better. I physically feel better in my body just moving around doing parenting stuff. I am excited by the stuff that we’re shipping, and so I feel challenged by that, but I also feel this edge chip on my shoulder a little bit as I’ve been seeing my little SaaS go out in the world and get bullied at lunch. And so that is a change. So I’m going to have a conversation with my accountant next week to be like, Hey, look, we need to, let’s look at how we’re doing now. We’ve had multiple cashflow positive months. I haven’t changed my compensation. Let’s come up with a roadmap to do that so that I can continue to reinvest money in the business. Because the long term bet is that AUN becomes a bigger company, multimillion dollar a RR business. That is still the goal. It’s not to squeeze every dollar out of it. And we will talk through that next week and kind of see what options are around, what are some milestones, what’s a reasonable way to do this so that I’m reinvesting the business and reinvesting in the team, retaining the team. We’ve got awesome people. So they also have bills and they also have responsibilities, and they also have aspirations for their lives. And so it’s not just me that has these things that I’m thinking about too.  

Rob Walling:
As Harris was looking forward, I wanted to see what he was most excited about next.  

Harris Kenny:
Yeah, so for the next six months, it’s hammer down. I think that I’ve seen what’s happening upmarket. I feel like it’s, we’ve had this, the emperor has no close moment. I think we have a really good thesis on what’s happening, and I look at what’s happening with these bigger companies in the space, and I think there’s totally a lane for us. So I want to double our MRR. I want to hit 1 million ARR by the end of the year. So we have four months basically to double. I think that if adding these new channels accelerates revenue, I think it will. I think it’s a reasonable goal. I mean, our compound annual growth rate, if you just project it out anyway, it’s a reasonable goal to hit. And I think that we’re going to bend that curve up. So I mean, I’m excited to make the changes on the personal side, financial as the business has more resources to relieve a little bit of personal pressure and also distribute some of that to the team too. I want everyone on the team to feel like they’re participating in the success of the company. I want to drive that revenue up by adding new channels and really turning this thing from a connector app into something much more, which we’ve been slowly getting there.  

Rob Walling:
Harris had just outlined some aggressive goals doubling revenue in four months to hit a million in a RR. It struck me that his confidence seemed different now more focused TinySeed markets itself as the accelerator for ambitious Bootstrappers. And I was curious how Harris’s relationship with that ambition evolved since he’d first applied more than a year ago.  

Harris Kenny:
Everything about this is kind of hard. I mean, this is a hard thing. And so I think when I think about ambition and channeling being an ambitious founder and wanting to build something cool, it’s just like you got to choose what’s hard about it. And I think what TinySeed allowed me to do is focus on higher value things that are hard because there’s stuff you just got to get through, and it’s a lot easier to get SOC to when you can just sign up for the platform and just sign the contract with the auditor and just move on to the next thing that is going to grow the business. So I think that anybody that wants to start their own company has plenty of scoops of ambition in there and plenty of stuff they’re trying to do. But I think when I think about the impact of TinySeed, for me, it’s like, okay, but where are you going to channel that energy? 

And it allowed me to get some basic things out of the way so I can focus on the harder things, which have fueled the growth of the business. And it definitely has stoked the ambition and aspiration and hope for what I wanted to build and what I want to build. I definitely don’t see myself being cool lifestyle business check. I’m going to bump up my salary and take off eight weeks a year or whatever. I mean, I still feel like we’ve got a lot of work to do, and so that’s the same, but I just didn’t realize how nice it’d be to get some of that stuff off my plate. And then once it was off my plate, I was like, oh, wow, that was, thank God. That’s over with.  

Rob Walling:
As we wrap up your season of TinySeed Tails, what final thoughts do you have for a founder who’s listening to this and there’s thousands? No, there’s tens of thousands of folks just like you listening to this episode right now, and a lot of ’em are wondering if they can make the leap. What do you think? What thoughts do you have for ’em?  

Harris Kenny:
There’s no cavalry coming. I mean, if you want to do this, you have to sit down with yourself and potentially with other people in your life, what going on? And you just got to decide that you want to do it knowing that statistically it’s probably not going to work, but that if it does work, it would be worth it. I mean, I think that that was a gut check moment that I even just had a few months ago around my own physical health. It’s like, you just got to get up, lace ’em up. I’m like, let’s go. I think that when you make that decision and you continuously re-up that decision, because every day you can quit multiple times a day, you can quit and nobody’s going to make you keep going, but you just have to keep doing it. It’s like you’re exploring a map, but the map is unknown, and so you have to keep going and pushing forward and pushing forward and pushing through the fog to to discover the map, and maybe you run out of map. I don’t know.  

Rob Walling:
I love that map analogy. Business requires risk going off the beaten path and trying new things. Success will never be guaranteed, but when it works out, it’s one hell of a feeling. As we moved into wrapping up our final recording session together, I wanted to thank him for the honesty he’d brought to this entire season, and Harris’s response reminded me exactly why these conversations matter. Thanks so much, man, for taking the time to jump on the mic with me every couple months and the feedback that we get. I know you’ve already received some feedback because most of the season has aired. For folks who don’t know, we’re recording this as I think episode four already aired, and so this is very much up to date as of September of 2025, and you’ve been getting feedback and the feedback we receive about all of the TinySeed tails episodes or that they’re really inspiring and whether you have a great success or you don’t quite make it off the landing pad. Hearing other founder journeys I think can help people help normalize it a bit. It always feels like, am I doing this right? Am I doing this wrong? Am I the only one that feels this? And then you’re like, oh, no, people who are quite successful feel and go through the same shit that I am or that I was. And I think it’s a real gift that you’ve given by giving this much of your time to be willing to record this season. So thank you.  

Harris Kenny:
Yeah, yeah, yeah. Happy to do it. So yeah, it’s been great. And remember, just context for me, technically, I had, you could argue a failed consultancy, a failed agency for failed SaaS ideas. None of those materialized into amazing outcomes. So technically, this is kind of my seventh idea in almost seven years. So you just kind of got to keep going, and it just depends on how you think about it. And I’m happy to share the story, and if it helps one person do something cool, or at least take a chance time more than well spent. So thanks for the opportunity, man.  

Rob Walling:
I 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.