Episode 793 | TinySeed Tales s5e3: Building Momentum

Rob Walling:
We’re back with episode three of Season five of TinySeed Tales. I hope you’re enjoying the season so far. Before we dive into the episode, I wanted to let you know that TinySeed applications are open for our Fall 2025 batch. If you’re a B2B SaaS founder with at least $1,000 of MRR and you’re looking for the perfect amount of funding, a community of ambitious like-minded founders and a network of world-class mentors, you should apply. If you know your metrics, the application only takes about 10 to 15 minutes to fill out applications close on September 9th. Get all the details at TinySeed dot com slash apply, and even if you miss the application deadline, enter your email@tinyc.com slash apply and you’ll be notified next time we open applications. Let’s dive in.  

Harris Kenny:
I believe really firmly that we are ahead of the market. I think that the users that we’re signing up and the prospects we’re talking to today represent the very beginning of a big chunk of a bell curve of the market that’s going to be changing its process.  

Rob Walling:
Welcome back to TinySeed 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 startup accelerator for ambitious SaaS Bootstrappers here in season five. I’ve been talking to Harris Kenny, founder of Outbound Sync. In our last episode, Harris moved on from a broad market approach to zeroing in on agencies helping clients with cold outreach. Time will tell if the move paid off, but early indications are that it’s working out soon after closing the biggest contract in the history of his company, Harris sent me this audio message.  

Harris Kenny:
We just closed our first enterprise deal. It was really nerve wracking. Ended up spending a bit of money with attorneys going through the contracts and things like that, but we closed an annual contract for $20,000, the largest we’ve ever closed by far for rep on sync. And then we’ve got two other mid-market deals in pipeline that are going to be for our Salesforce integration. Then another couple of Salesforce ones pending, so we’re going to go from one to five paying Salesforce customers probably over the course of a month, and MRR is just, it’s hopping up. We’ve got a couple agencies now that are really growing and so we’ve got some nice expansion revenue with them and this feels like the beginning of a big jump. So it was like three months of pretty flat bouncing around, just hovering around an under 10 KA month and then all of a sudden it has just popped and I feel like this is going to be another good month. And then if this continues through to December. So anyway, feeling really excited and it’s funny, after those three months of flat revenue, I was genuinely wondering if I was making the right decisions. I was just spending money and spending money and spending money, but right now it feels like those bets are paying off. I feel more confident than I ever have that this might work.  

Rob Walling:
So it sounds like things have, I dunno, turned a corner, may not be the right way to put it, but where were you flat, relatively flat for three months and now it’s like things are really accelerating based on all the investment of time and money that you’ve been doing over the past few months?  

Harris Kenny:
Yeah, definitely. I mean, there was a few things that happened at once when we got into a TinySeed and I was spending a lot of time shutting down my old agency, which now I can say officially we have no clients left, and I talked to my accountant, we like, here’s the roadmap for dissolution of the entity, all that. So that’s really happening. So that was a little bit of a distraction. I was also a little nervous to spend the money. It was the most money I’d ever seen in a bank account before, and so this kind of evolutionary instinct of hoard and then also how to spend it and so it took time to spend some of it. So while all that was happening for a few months, revenue was flat. We had a little bit of new customers, but a little bit of churn. 

And so then I was starting to get anxious about that and I was questioning do I know how to do this actually or did I only build a pretty good idea? And then I don’t know actually how to run a software company. I technically don’t know how to run a software company. I’m learning right now how to do it. But then September was our highest month ever followed by October, followed by November, and now it’s December. Again, highest month ever. And the anchor for that is an annual $20,000 contract. I’ve never signed an annual contract worth this much before. We had one earlier annual contract a couple months ago, but it was just for 5,000. So this is like we went through the process, we went through procurement, we went through legal, I had the privilege of paying our attorneys to review the documents and a lot of things that I had just invested in around security and stuff. 

When I was doing the questionnaires, I was actually checking the boxes of like, yes, we literally are doing these practices. Whereas before I spun out Aon sync, I had gotten the security questionnaire and I didn’t even know I looked back at that old spreadsheet and I didn’t even really understand what they were asking me. There were things where they asked and I was like, I literally just didn’t understand it and now much, much, much longer more complex procurement form. I not only knew it, but we were doing it. And so that just felt like, oh, okay, we’re playing a different game. It felt like I could one day have a salesperson doing this and not me. And so that just felt like really big progress even though they still haven’t paid us yet, but it’s net 30 and hopefully they’re going to pay the pay invoice. Yeah, so that felt like in the beginning of this is more of a software company, we’re growing, we’ve got these big contracts and I can have that conversation with the procurement team. I understand now a little bit of when they’re pushing back on what they’re pushing back on and what we can say yes to and no to, and all of that was just like I had no idea a year ago at all.  

Rob Walling:
For a long time I’ve been saying if you have to go through procurement $25,000 minimum a cv, and now I think I’m up to about given inflation literally and just how many years it spent. It’s like I think it might be 30 or 35 is my number. It’s almost 30 grand a month that makes it 2,500 in there. So I got to raise my prices, I think. So I mean if you truly do have to go through a full procurement process with security questionnaires and all that and potentially redlining your terms of service, whatever, all that happens, it’s expensive. When you pay your own lawyers to deal with this. Harris started the SOC two process about three months ago. It can be tedious and expensive and many early stage founders want to avoid it as long as possible, but it can also be a big unlock for closing bigger deals.  

Harris Kenny:
So we’re basically at the finish line and ready to start the audit. We implemented a lot of changes and actually they’ve been really beneficial. So I’m a non-technical founder. There were a lot of things that maybe a engineer founder would’ve set up from the get go that I mean, I’ve just always said to, we have one engineer and it’s just been like, Hey, let’s just focus on what customers need and whatever you need to do your job, but I’m not going to give you extra stuff to do. And so he was just pushing to production basically. And there were practices that SOC two requires that in hindsight we’ve implemented them and it’s been really good. So one of them is we have a staging server, and so we test every feature before it goes to production. And I know that we probably should have been doing that the whole time, but whatever. 

We didn’t even have customers in the beginning, so it kind of like wasn’t worth it. Another thing was security, which is actually already benefited us. We have now a web application firewall installed in Heroku, and we caught a potential issue that one of our integrations was sending over payload that could have been a cross scripting attack. And so we caught that because we had this add-on and engineer caught it, we troubleshot it and came up with a fix. It turns out there was no malicious issue, but there could have been. So basically our infrastructure was doing its job and none of that was in place prior to starting SOC two. So then we were able to tell our customers like, Hey, we’ve identified this issue. Here’s how we are now solving it. It’s actually not something we can control just getting this data, we’re getting these webhook payloads, and then we got to figure out how to deal with them and we want to make sure because we have right access to yours or your customer’s CRM, like your Salesforce, HubSpot, we need to make sure that we’re being diligent about what we’re passing along basically. 

And so it made us look really good and we have a status page, which we didn’t before, but we have that because of SOC two. And so I said, here’s the writeup of the incident and here’s the updates and here’s how we resolved it. And all of those things just felt like as we were doing it, it just felt really good and I feel like it established credibility with customers because we’re between these big platforms and so we have to prove ourselves of how do I know you’re not messing up on this? 

Who are you really? To me, and we’ve closed quite a bit of business because of it. We have gone through this big enterprise deal we just talked about, but also quite a few others. I’ve just sent them a link to our trust center and they’re like, okay, great. Yep, we can see you’ve got a lot of stuff in place. So I mean it has investing in that has improved our product, improved our customer support and increased our sales. It just forced us to grow up a little bit in ways where I want to take the company. I want it to be doing multiple millions in a RR, and so it’s like, okay, we were going to have to grow up in these areas. And so it kind of forced that to happen in a structured way where, I don’t know, I’m really glad about it. People gripe about it and I sort of get why, but in hindsight, I think if this thing works out, I think that’ll end up having been a really important decision at the time.  

Rob Walling:
Yeah, I would gripe about it. I hate that kind of stuff. You’re building a business and you come from the sales side and you know that to make sales and to get big fast, you’re going to have to close big deals and to close big deals, you’re going to need SOC two in this space, you just inevitable. And so you have just accepted it like a mature adult. I would tantrum and be pissed off the whole time and I would complain about it like a baby because I’m here to make great software and I’m like the crafts person and I’m like, oh, I want to do product and design stuff and make sure this is all elegant. And so I’d be like, ah, this sucked too. Why do I need this? This is just a headache. But you have just on this particular instance, I’m sure there are other ones where you take the opposite attack and that’s what we see within TinySeed. There are certain founders who are more like me who are like God kicking in screaming, just scratching and clawing. You have to pull from my cold dead hands. The knot not going to SOC two. And then there are those who are just like, nah, it’s not fun. But I also know that I’ll probably close literally hundreds of thousands of dollars in a CV next year if I have this that I will not if I don’t. And so that becomes the question that a lot of founders have to ask themselves  

Harris Kenny:
For sure. And it’s given me a better lens to understand what’s happening with our product. I understand technically much better how our product is working because of it.  

Rob Walling:
We’ve been talking about getting SOC two certified, a process that doesn’t come cheap, but that’s just one piece of Harris’s growing expenses with a young family at home and a business that’s scaling up. Every financial decision carries extra weight. I wanted to understand how he’s navigating these waters.  

Harris Kenny:
Before I ran an agency for five years, it was profitable. It had to be, but it was never like a breakout success. I was never able to fully hand things off. I was never really able to take a vacation. It was always hard still, even though I was financially successful. But also I had an LLC that had a sub S selection, so I was able to pay myself in a different way. I had distributions. I had a lot more flexibility starting up on sync. I wanted it to be proper software company, and this wasn’t a TinySeed requirement just in my head. I was like, I want to set this up from the beginning clean and not have it be muddied with my five year LLC with three different accountants and two different lawyers. And it’s like, I just want this to be a fresh solid start. 

And so that change, I did not fully realize how much that shift of, okay, now I’m only getting paid a salary because Zon zinc is a C corporation. And so now we have payroll through a DP and that’s it. That money that I get paid, that is my money. And I was just used to before being like, well, I can take a distribution out of here and make sure I can cover this or that unexpected expense. So that introduced a pressure that I didn’t think through fully at the time. I had five years of not having that kind of constraint that I sort of forgot what it was like I could always figure it out. Basically. I always found a way I landed bigger client or this or that. I started spending the TinySeed money more to get the growth going. And I would say both of those investments have been worthwhile. 

Developer is very productive. He’s doing great. We talk very little. He just cranks on stuff we check in. It’s a really great relationship and I can tell the difference him going to 40 hours a week, the productivity is way outstripping the percentage increase of time that he’s working. And then the CSM has been good because it’s freed me up. So he’s focusing on onboarding, getting new users. That hire has worked out so far really, really well. We went through dynamite jobs, recruiting board, remote first recruiting, and they found a very good candidate. I think he’s really taking ownership of things, he’s just running with it more, and that’s freed me up to focus more on sales. I think that’s why these last couple months have been getting better in terms of sales. I think that with these three people, me and CSM and engineer, my goal is that we get to 30 KMRR and that would give us plenty of head room at this point to be default alive. 

I’m just kind of trying to run as hard and as fast as I can to get to that. I could lower that number though if I reduce my own drag on the business. So in the home front, I’ve been implementing a budgeting app called yap, you need a budget. And we now have four months of my wife and I have four months of budgeting data of our own spending down to the cent. I did my own books for a while and I took accounting classes in business school. So fortunately that’s actually been pretty easy to do it just as you sit down and do it. So I’m trying to figure out how do we tighten up spending on the personal side so that I can reduce my salary, that I can extend that runway a little bit more. But yeah, right now I’m thinking about this a lot right now and we’re good now, but projecting out six months, I’m kind of like, okay, well, would I do a revenue-based financing? 

Would I pull some money out of retirement? We’re not running out of money yet. We’ve got money in the bank, but because I have this salary, I have these hard edges that I have to operate within. I kind of have to plan out further than I’ve ever had to plan before. It’s totally connected. And we had a little bit of churn, and it’s really hard to not be get too down about that. It feels like, oh, everything’s jeopardy. I was close and now I’m further. So there’s that. Yeah, it just feels like everything is all in one  

Rob Walling:
Basket, man. It’s tenuous because you grow another five or 10 KMRR and you’re like, well, finally we’re breakeven or we have a profit. Oh, now, but I need to hire an engineer to keep up with X, Y, Z. So I’m not saying it never goes away, but it really is, even when you’re doing a million, 2 million, 3 million a year, it’s always this balancing act and you do get more margin, but it’s not like at 3 million a year you have a million or 2 million just pouring out out of the bank account into your personal one. There’s still a stress, but the thing that as a founder you have to keep in mind is don’t sacrifice your own personal finances or your families in order to get the company going. But yes, there is risk. So how do you balance that? That’s the hard part. That’s why founders as a rule tend to have more anxiety and stress in their lives than employees of big companies, but employees of big companies tend to have a lot more depression than founders do. 

And there’s multiple studies that have verified that. Sherry, my wife has talked about this in a few talks. It is more stressful. The upside is significantly higher, but that does not come without some risk and some uncertainty. And those two things are tough and they’re tough on you and they’re tough on your partner or significant other so far, I think you’re thinking about them in the right way because you can be so stressed about them that they keep you up at night and that you hate being a founder. And if you sell this company or shut it down for years from now, you never want to do it again. Or you can not worry at all about it. And you can be like some people and they take out 50, 60, $70,000 of credit card debt to start their company and they’re not nearly risk averse enough. And it’s like there’s some balance in between of how do I be mindful of this risk but not let it destroy the journey and not let it be on my mind every minute of every day?  

Harris Kenny:
Oh, totally. I mean, I think fortunately, I’ve got some levers I can pull. I mean to go into my personal finances a little bit, I’ve got a universal life insurance policy that I had set up when we first got married. It’s like, okay, well let’s cash that out. Let’s set up a term policy that’ll actually pay out way more. And then, okay, I’ve got that little bit to pay off some debt, so now I’m reducing my month to month debt servicing that I’ve got in this area, better insurance than I had before. So there’s little levers like that that I’m pulling in a few different areas to. And then I mean, there’s hope on the horizon. Currently. I know for a fact that 35% of our income goes to childcare, but we won’t have young children forever. School is on the horizon. And so it’s like, okay, it’s possible that in three years we’re at MicroConf and I’m like, Rob, drinks are on me because the company’s ripping and we just freed up multiple, multiple thousands of dollars a month and free cash flow that aren’t going towards childcare. I do. I have that on the horizon that I think is a reasonable thing to look forward to. It’s not like maybe I’ll be on a boat, but it’s not like I’m going to be a hundred millionaire or whatever. That feels like a reasonable thing if I could just get there. That’s my mindset right now. We’ve gotten really far in a short amount of time. I think I can get there. I just have,  

Rob Walling:
It should get easier. I mean, you are still very early in this business and the early days, everything’s fragile. Even your knowledge and confidence that business is going to work is pretty fragile. Your product-market fit is really fragile. Your sales process is fragile. You are thinking of who is this revenue going to stick around? Is it going to continue to grow? All of that’s fragile still. And that does solidify as the company matures. Harris has talked before about expanding to other CRMs outside of HubSpot. One of his newest missions was to integrate Salesforce, and I wanted to see how that was going  

Harris Kenny:
Well, so okay, I didn’t cheat, but I did maybe bend the rules of what maybe you were thinking a Salesforce integration is because there’s two ways to integrate with Salesforce. And we did a connected app, which is essentially a private unlisted app. And so that allowed us, and this is what we did with HubSpot too. It allows us to sell to Salesforce customers. They just basically create their own authorization for our web server to hit their Salesforce account. So that was how we moved so fast. And then the other thing we did was we started with a tiny, tiny, tiny footprint of what it does. And so we just solved a very basic problem of we log emails as activities. Do you want that? And enough people were saying, yeah, that they’ve started paying. So we have multiple paying customers. We’ve got a mid-market company that we’re in procurement process with now who wants that, and then another one who has said, Hey, I’m going to sign up for this probably in the next week. 

So I think that we’ll go from $0 in Salesforce revenue to probably like 2K MRR probably by the time we hit January, all of that closing basically over the course of a month. And then if we do that, if all of our other numbers stay the same, I’m just doing quick calculator math here, that’ll end up being like 15% of our revenue. So that’s pretty cool. But we’re using Salesforce brand as distribution, but not the app exchange. The same thing we did with HubSpot. I talk about it on LinkedIn and I talk about other agencies and I say, if you use HubSpot, we can support you. But the HubSpot thing, I was really, really, really, really proud of getting that, and that was cool. But we were selling a HubSpot app for over a year before we were in the marketplace, and I think we’re going to do the same thing with Salesforce. It literally fast could be a year, and that’s moving  

Rob Walling:
Fast. That’s moving fast and getting a V one out there, and then you built thousands and thousands of MRR. I mean, you could have supported yourself almost full time on the business and didn’t have to wait for any of that. And this is what the best entrepreneurs do. They get it done real fast and then they turn around and say, all right, well what’s V two? Well, V two is getting in the app marketplace. Then we get promotion and all that. You got into even the HubSpot app marketplace, it felt fast to me. I don’t know what the timeline was,  

Harris Kenny:
But yeah, I had only took two weeks. Crazy. We were so ready. We blew past their request.  

Rob Walling:
You already had paying customers on it. Normally you go in the app marketplace with no customers and then they’re like, Nope. Testing for months and you need to have this many beta users and you already use it through it. That’s another  

Harris Kenny:
Example. Exactly.  

Rob Walling:
And you said, and I quote, we are the first smart lead integration in the HubSpot app marketplace, and you sounded really proud of that  

Harris Kenny:
Before even Smart lead themselves.  

Rob Walling:
Yeah, before their own integration, you beat smart Lead. So that’s got to be a pretty big point of pride for you.  

Harris Kenny:
Oh, for sure. Yeah. I think we’re shipping really fast. I was in the chat with the founder of Smart Lead and he was like, you Ship, which they have a great engineering team, so I know he really means that as a compliment in their world, they really value engineering. We move fast and we’ve got two other sales engagement platforms that I think are going to potentially open up market for us. It’s the same core product, but competitors to Smart Lead. And I think again, we will be the first integrations listed for those tools. And I think that when we move, our positioning is going to change to be like, Hey, if you’re using one of these outbound tools, we’ll be the one that gets it in your CRM the right way. I think we’ll be able to charge more. That’s kind of what’s on the horizon. But I think that this play that we just ran Smart Lead, I think we’re going to run twice again for two other tools. And now I’ve got people being like, do you support list? Do you support this? Do you support that? And so we’re starting to get a wait list forming for other tools, and that just kind of feels like to me, again, we’re in these more advanced stages of becoming a real company call that market  

Rob Walling:
Poll where it’s like, and you’re getting data because you’re like, oh, we have three requests for limbless and we have two for this other tool. I don’t know the baseball enough to know, we know what the tools are, but two for this other tool. And then it’s not necessarily you build the one that has three and not two, but it’s a signal that you didn’t have two months ago. And so now you have all the CRMs on one side and you have all the what? Cold email tools I guess on the other side, right? That’s what you’re thinking.  

Harris Kenny:
But could be LinkedIn, could also be phones.  

Rob Walling:
Yep. So there’s a lot to be done here. And this is one of the reasons we invested in you and invested in this business is because in you, we asked ourselves, do we think he will figure this out? You were early, right? We don’t know if the business is going to work. Do we think that Harris can do this? And the answer was, yeah, I think he can do it. And then why did we invest in the business? Because it had traction, it had people that wanted to pay you, and I see the potential of this to be a seven or eight figure error or a company not with the initial product you had. It was what smart leads to HubSpot and it was very simple and it was first Zaps and then you had someone write, I mean that’s not an eight fit your business, but all the division that you’re starting to paint here and the request, the market pull, you’re starting to get that absolutely could do 10 million or more in a RR.  

Harris Kenny:
Yeah, I believe so. And I will say I think this, to me, this is why TinySeed is different. It is still fundamentally a venture endeavor. The risk of investing at the time. I mean, it reminds me of when my wife decided to marry me. It was like the rest of your life are you, are you sure potential? You see potential? Yeah. I’m not sure that I would marry me at this point. We got married, not super young, but it was a while ago. We’ve been married for a long time. But yeah, so it’s fundamentally there was a risk there. And so yeah, I feel like you all took a chance on me and it’s been cool.  

Rob Walling:
You’re making good progress, man. Looking ahead over the next one to three months, we will record in the next one to three months. What are you most excited about?  

Harris Kenny:
I believe really firmly that we are ahead of the market. I think that the users that we’re signing up and the prospects we’re talking to today represent the very beginning of a big chunk of a bell curve of the market that’s going to be changing its process. We have taken customers away from outreach and they’ll do a demo with me and I show them the reports and how we put the data in their CRM and they have said, okay, great. What email tool should we use? I don’t even care. I just need the data that you are giving me. And so to be taking customers from outreach, which is a unicorn, arguably created the sales engagement platform category to be taking users from them as a connector app, which I think we’re doing more than that or solving deeper problems than that. To me that’s a really big deal. 

And we, we’ve got two customers, one we just closed and another one that’s about to close that were like this and they’re like, whatever, however we need to send the emails. I just want the way that you are putting it in that system. So I think we just keep moving down that path. I think there’s a lot more people to come basically. And I think the people we’re helping right now, early adopters. And so if that’s true, then I think we’re going to have really good mojo. I think we’ve got some really good agency partners, and I think that when we add build out Salesforce, and when I start talking about Salesforce more and posting about it more, and when we add some of these other engagement platforms, I think that we will start unlocking more pieces. So I’m really confident in that potential, and I think people are spending a lot of money on their tech stacks, not able to answer the questions that we’re helping them answer. And so I need to figure out how to become a more mature product marketer to capture that, because I talk to customers who get it, but can’t trust. I can’t wait for everyone to get it. 

But I think that’s where the opportunity is. And I think that when I look at where we’re taking business from, it’s not just people who are using Zapier right now. It’s people who are spending a lot more money on much more sophisticated tools being like, yeah, but this still isn’t really solving my problem. And you are. That is like, okay, cool. It’s super motivating. Outreach is fine. Maybe we’ll integrate with Outreach. I have no beef with ’em. Like whatever. It’s just a B2B SaaS software, who cares? But the competitive side of me is like, okay, yeah, we’re doing something. We’re making a mark, we’re getting people to switch, which is cool.  

Rob Walling:
What started as a simple connector app has evolved into something much more ambitious. Harris Harris’ finding his product isn’t just competing with simple automation tools. It’s pulling customers away from industry giants. And in today’s market where companies are scrutinizing, every dollar spent, their tech stack outbound sink seems to be resonating. The question is, how far can this unexpected momentum take him? Find out next time on TinySeed Tails. 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.