How TinySeed Helped Me Grow My SaaS to $500k ARR (in 1 Year)

0:00When I first started working myself, I wanted the independence that comes with that. And then I realized that some business models are better than others. And so I tried a few times to crack a software product. It felt like I finally got it. When our SAS was getting feedback, we were getting good prospects coming in. We were running into tricky problems. Felt like I was finally solving a problem that people actually wanted solved. I joined Tiny Seed to help pursue that. And you know, here I am a year later up on Syncs at half a million dollars in annual recurring revenue. We've got a great team. Because

0:29we joined Tiny Seed, I really believe that it put us on a trajectory to be where we are now. And I'm feeling really optimistic about where we're going next. Today, I'm talking with Harris Kenny, founder of Outbound Sync, about how he used seed funding from Tiny Seed, the B2B SAS accelerator I run to turn a low code MVP, into a full-fledged SAS business doing over half a million a year in annual recurring revenue in just about 12 months. We're going behind the scenes of what really happens after you join a startup accelerator. We'll talk about what the Tiny Seed program looks like through a founders's eyes, how

1:03Harris decided where to invest the funding and the thinking behind those moves, the unexpected benefits of being part of an accelerator, and make sure you stick around till the end to hear the surprising advice he has for other founders like him. Let's get into it. So, Harris, before we get into what happened after you joined, take us back. Where was your business right before joining Tiny Seed? I was running an outbound agency and we were a HubSpot solutions partner. Basically just realized these tools didn't talk to each other. And after a few years of testing a few different SAS ideas, it felt like this might be a good one and I pieced

1:34something together with low code, refactored into full code and that's when we started building momentum and I felt like I was getting in over my head. That's what prompted me to apply to Chinese Seed. Do you recall what your MR was? Yeah, we were around like 7,500 MR at the time. And now a number of those were bundled with clients. So it was pure software subscription, but there were a lot of things that we were doing that weren't like a a normal SAS would be. I just knew there was a lot there was a big gap between how I was running the business and how and and where it could get to,

2:04but where it was at the time. And right from the start of the program, you were making a lot of moves to grow your business. Let's talk a bit about how you spent the money that we invested and how you decided what to spend it on. Well, one of the indications that we were on to something is that I started getting prospects asking about SOCK 2 and vendor compliance. And I didn't know what they were asking for. And so I just basically lost a couple deals. And as I as it came up more and more, I came to feel like this is going to be an

2:37important part of our business. Like we should probably get sock 2 type two. So that was one I got pretty quickly. Um, and I mean it's funny, but it was, let's just say, rounded around $20,000. And we closed a $20,000 enterprise deal like literally within a month of getting it. And we flew through that procurement process because we had the documentation. And we have subsequently closed, I mean, a bunch of deals. I mean, every couple of weeks, one will request access to our trust center. They see the docs, they're happy with the report, we close the deal. So, that was one that was just really obvious um, and

3:10like a really clear ROI that you can't even really dispute. But I think that I mean for me personally it was like shutting down the agency and going all in on one thing. Um I definitely used the proceeds from Tiny Seed to get myself fully committed to the business. And I think that that focus was a huge deal. I I just like I couldn't keep doing multiple things. Being a solo founder of a software company or even a co-founder software company like that's a full-time job and I was juggling just too much before. I just couldn't keep it up. So that was another huge one for us

3:38and for the company for me was just hiring myself, buying out my time so I could focus on building and and then other hiring decisions were big. Um we also saved money in some areas because of the tiny seed perks. So like there were areas where we needed to upgrade our tech stack but it actually didn't cost anything because Tiny Seed has all these perks and benefits for portfolio companies. So um yeah, there were actually things that on paper should have cost us money but we but ended up being free that I was expecting we would have to spend the money on. So it was

4:04kind of funny how that worked out. Definitely the tiny seed mentor sessions and community helped me with allocating that capital for sure. I mean broadly it was like hire people, invest in some of these compliance things for sure. Um but then there's also smaller things. I think what's tricky about being a bootstrap founder is that there's actually not a lot of great advice for you out there. I mean, sure, there's microcom and there are some different places online where you can find some things, but just in general, most of the advice is indie hackers where, you know, they're just trying to like piece together a bunch of apps or build things

4:39that are like five bucks a month or you've got these ventureback companies that have raised a ton of money. So, there is this weird gap of knowledge, but unless you're listening to startups, the rest of us and micro, like you're just not going to get a lot of it. And as great as those things are and I consume them both religiously like sometimes it's helpful to just talk to a panel of you know a couple hundred people who are doing it and just get like a bunch of other ideas um because just people are going through it right now and they're in that same company size. So definitely the community helped

5:06me with spending money but I would say more so um spending time of like dude don't worry about that or yeah yeah yeah you should be focused on that. What are you doing with pricing there? That's weird the way you just said you're doing pricing. should think about that. Um, you know, so I I think that that was maybe more of the like even more valuable was just like attention and time and yo yeah, think about this or

5:28don't think about this. You joined our spring 2024 cohort and from a founders's perspective, what did the first few weeks of the program look like? Well, the first week was huge because we met up with our cohort. Everyone got together. when I decided to go all in on my SAS and shut down my actual agency, quite a few friends who ran agencies reached out to me and said that they had been curious about what I've been building and now that I wasn't a direct competitor with them anymore, they wanted to try it out for some clients of theirs. And so, I mean, I'll always remember Andy Kim from Trotto and my

5:58cohort, he helped me flesh out the idea for what would become our partner program. And that became that's the majority of our business right now, and it's a huge part of our growth. So, I mean that that one 30 minute conversation before breakfast was like worth the price of admission, but that alone I think really changed the trajectory of the business. But it was just learning the basics of how's this thing supposed to operate. I'm making the money in a SAS way. I'm using Stripe. I've got customers that are signing up for a software product, but there's so many other things about running a software company that I just

6:25had never done before. And so, it was just figuring out what those things are and and just being okay with some parts of the business were really just not there yet. and that that was okay and just sort of getting a license to just say leave that alone for a second. You can worry about it later when you have

6:41enough money to pay to fix that. And so it sounds like you got a lot from the Inerson retreat. And then once you were back home from that, you started joining our Tiny Seed playbook calls and our mentor sessions. Does that extra structure actually help or did it feel like extra work? the value of the structured program with Tiny Seed. I think it was just looking at every part of the business. You know, it's like you're cleaning the house and it just makes you go into every room and one room is fine and you don't need to do a lot of work there and it's no big deal,

7:12but it's just like worth just double-checking and making sure that you cleaned it in the first place kind of thing. You're like, "Oh, I forgot to make the bed, make the bed, and then I move on." So, that's what it felt like. It felt like the structure of the program just took me through the different parts of the business. Some areas needed a lot of work, others we were in a pretty good spot. But I feel like sometimes you kind of have to have that like forcing function to look across the whole company. And then other areas I haven't even really still haven't applied the playbook yet because

7:37we're growing into that, you know, and some of these things I'm still doing myself that hopefully one day I won't be. And to give listeners an idea, we have eight playbooks that cover mindset, marketing funnels, pricing, sales, marketing, team and hiring, M&A and fundraising, and burn rate. Were there any specific playbooks that you felt

8:01were especially useful for you? Hiring, no question. I needed help. And I it wasn't really clear to me at the time, but we needed more engineering hours and we needed customer success and and those weren't things that I was thinking about necessarily going into it. Frankly, I had not been very successful hiring people in the past running my agency. I had had some good people who I like really enjoyed working

8:24with, but I also had a lot of misses. So, being able to just see how, you know, 200 companies have done it before, it's like, look, work with this recruiter. here's like five example job descriptions that other tiny C companies have done for customer success. Read them. Do your own twist on it. And you know that person has been incredibly effective contributor to the team. And then you know other conversations I remember we were at a table and you know we're talking about developer productivity and output and it was just like man they're not working anywhere near enough hours. They are split still split between other projects. Like this

8:56is a no-brainer. Bump them up to full-time. like get this thing, you know, get people fully focused on what you're doing. And there was just things that were really obvious to people in the room and to you and obvious in the playbooks that I just didn't um you know, I just had total blind spots on. So, yeah, the hiring one was a no-brainer and that I feel like set things in motion that had that basically made every has made everything else work

9:16since we joined. Was there anything you didn't get from the Tiny Seed program that you thought you would? I mean, honestly, this is kind of cheesy, but tiny seed is literally what it says on the tin. Like if you read the website and you read the FAQ, that is what it is. I don't I I can't think of like a higher higher praise to give about like someone's marketing than it is entirely truthful. But my expectations were now I've been listening to, you know, reading your work for a long time. So I felt like I had a sense of what I was getting into. But still, Tiny Seed is a

9:52a specific implementation or it's a specific idea. And it has totally been my experience. There has not been this pressure to grow at all costs. There has not been really, you know, invasive needling and questioning and challenging our strategy and, you know, pushing to do these wild things. But I will say one thing that has been maybe demonstrated more than I would have guessed or has come up more than I would have guessed is the optionality concept. Like I really think that is like infused into how tiny seed operates as an accelerator but how the team operates and all that. You really do hear people talking about ideas around

10:30raising more money or you know exit options for them. You know it really feels like everyone is trying to build businesses and businesses can have many outcomes and businesses can have many transformative events. It does not feel like everyone is trying to pursue the same exact goal of hitting the same exact MR in the same exact way. And so that has surprised me a little bit. The like variety of decisions that founders are making and um and how agnostic tiny seed itself is about that is I didn't expect differently but the number of different situations that come up. You sort of can't anticipate that because when you're so early and you're just

11:06trying to build something and hoping like anybody cares, these different things don't come up at that time. Yeah. Yeah, but then you grow and then you know somebody gets a nasty gram from an attorney or somebody's something happens with an employee or a contractor or an exciting growth thing comes up and just like there's just so much that can happen and I think that the the flexibility and the sort of steady hand from Tiny Seed through all those things is has been interesting and I didn't know to expect it. I guess I didn't even think about all the like things that could go right or could go

11:34wrong because I was just literally just trying to like pay my bills and get anybody to care about what I'm making building. Yeah. Well, I I appreciate that because my co-founder and I put a lot of thought into that this word optionality that you said. And so, if someone's watching this and they're thinking like, "What does that even mean?" I want to let people know like there are a lot of tiny seed companies that never raise another dime of funding after tiny seed. There are a bunch of tiny seed companies that raise 100 to 500,000 from angels and from our syndicate and from other places. And

12:05then we have tiny seed companies raising series A's that that have raised six 101 13 million right so that's that's what optionality is right once you take venture you leave some options on the table and uh once you go down certain paths you can you know they're often oneway doors and we've tried to make tiny seed not that right we've tried to make tiny seed give you uh a lot of flexibility into what you can do because you hinted at it but when you're first building a company you kind you often don't know how big it can get. You may think it's a bootstrapped business and

12:36then you may suddenly realize, oh my gosh, we hit 2 million ARR in 18 months. Didn't think that was going to happen. Now suddenly, do you sell it for life-changing money, never have to work again? Or at that point, do you raise more to to take another bite? And we never wanted our terms to interfere with

12:52any of those options. I mean, one thing I'll say too is like perception matters. So, like when I told our customers and our partners that we were joining, people were like, "Cool, it's awesome." But I've seen other companies in our space do like other financing things, really aggressive financing things. And I've like seen people in different group chats, things

13:11like that be like, "Oh gosh, here we go. What's this going to do out going to raise prices?" Yeah. So, I feel like, you know, it it's it's just enough funding to open up doors or extend runway, but it also doesn't it it doesn't have like negative ramifications externally to the company. It's like, oh, that's like a really modest amount of money and it looks get some great advice and oh, I actually recognize a

13:34few of those companies I've invested in. Cool. Like, so there was really no harm from that perspective where I have seen companies make financing decisions that there is harm. There is like brand reputational like concern. people say, "Oh, h okay. Well, like like I'm I'm where's that going to leave me? Am I the

13:50right customer that for them anymore?" Um, so anyway, that's like a really nuanced subtle thing, but like I really care about what we're building and you know, actually really love our customers and consider them friends, personal friends. And so I do think those little things on the margin matter. And I I do think the tiny seat is beneficial in that way, which, you know, if someone's thinking about this and they're really on the fence, that that would be maybe something to think about. In a minute, we'll get to the advice Harris wishes he would have heard before he applied to Tiny Seed. But first, I wanted to let

14:19you know that applications for Tiny Seed are now open. If you're an ambitious early stage founder with B2B SAS doing at least $1,000 in MR, you should consider applying to Tiny Seed. As you've hopefully heard in this interview with Harris, you'll get the right amount of funding, join an incredible network of like-minded founders like Harris, and get access to worldclass mentors to help you grow your SAS into a life-changing business. To get all the details, head

14:43to tiny seed.com/apply. Applications are open until September 9th of 2025. But if you're watching this video after then, sign up for our email list to get notified when applications open next time. All right, let's get to the advice Harris has for other founders. Do you have any advice that you'd give someone who's applying now that maybe you wished you'd heard back

15:03then? Something that I read from Tiny Seed, documents, things like that, but I I probably didn't take seriously enough was the encouragement to just apply. If you're not sure, if you're on the fence, there's not it's not going to be held against you. If you if you think you're building the kind of business Tiny Seed might be interested in, you should apply. Now, fortunately, I had some additional people who encouraged me to apply that didn't work for Tiny Seed itself who were like, "No, they they actually really mean that. You really

15:28should apply." Um, but I would say that is not just window dressing. Like, they really mean it. Like, send the application in. It's there's not there's no harm. It shouldn't take that long to fill out. And if it does, then pause and reflect on that because it's a pretty straightforward application. And yeah, I would say I benefited. I was lucky that people told me that. I didn't believe it the first time. So, I was lucky that extra people told me and so that I did choose to apply anyway. Um, so maybe I will be that extra person for you. You should apply and uh a bunch of people

15:57apply multiple times and then get in later. You know, there's there's nothing there's no harm from it basically. And it it might only just open doors for you. If you want the full story of Harris's journey, you have to check out this season of Tiny Seed Tales, rolling out right now on the Startups for the Rest of Us podcast feed. For the past year, I've been catching up with Harris every couple of months, following his progress in real time. And what you've

16:19seen in this video is just a snapshot. Harris has been incredibly candid, sharing his numbers, his challenges, and the unfiltered realities of running an early stage SAS. So, make sure you subscribe to Startups for the Rest of Us in your favorite podcast player, or hit the link in the description to start listening. After investing in more than 200 B2B SAS companies, we've spotted clear patterns in what sets the standout founders and businesses apart. In this next video, I'll walk you through those lessons. And in lesson number two, you'll hear why Harris wasn't exactly a guaranteed pick for the program. Thanks

16:51for watching. We'll see you next time.