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[00:00:00.160 --> 00:00:04.960] We're back with episode three of season five of Tiny Seed Tales.
[00:00:04.960 --> 00:00:07.200] I hope you're enjoying the season so far.
[00:00:07.200 --> 00:00:13.840] Before we dive into the episode, I wanted to let you know that TinySeed applications are open for our fall 2025 batch.
[00:00:13.840 --> 00:00:25.360] 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.
[00:00:25.360 --> 00:00:29.600] If you know your metrics, the application only takes about 10 to 15 minutes to fill out.
[00:00:29.600 --> 00:00:31.920] Applications close on September 9th.
[00:00:31.920 --> 00:00:35.600] Get all the details at tinyseed.com/slash apply.
[00:00:35.600 --> 00:00:44.000] And even if you miss the application deadline, enter your email at tinyseed.com slash apply and you'll be notified next time we open applications.
[00:00:44.000 --> 00:00:45.280] Let's dive in.
[00:00:45.280 --> 00:00:48.000] I believe really firmly that we are ahead of the market.
[00:00:48.000 --> 00:00:58.560] I think that the users that we're signing up and the prospects we're talking to today represent like the very beginning of a big chunk of a bell curve of the market that's going to be changing its process.
[00:01:01.440 --> 00:01:07.440] Welcome back to Tiny Seed Tales, a series where I follow a founder through the roller coaster of building their startup.
[00:01:07.440 --> 00:01:15.600] I'm your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the startup accelerator for ambitious SaaS bootstrappers.
[00:01:15.600 --> 00:01:20.560] Here in season five, I've been talking to Harris Kenney, founder of Outbound Sync.
[00:01:20.880 --> 00:01:29.120] In our last episode, Harris moved on from a broad market approach to zeroing in on agencies helping clients with cold outreach.
[00:01:29.120 --> 00:01:34.080] Time will tell if the move paid off, but early indications are that it's working out.
[00:01:34.080 --> 00:01:40.240] Soon after closing the biggest contract in the history of his company, Harris sent me this audio message.
[00:01:40.560 --> 00:01:42.800] We just closed our first enterprise deal.
[00:01:42.800 --> 00:01:44.560] It was really nerve-wracking.
[00:01:44.560 --> 00:01:55.200] 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 Outbound Sync.
[00:01:55.520 --> 00:02:01.160] And then we've got like two other mid-market deals in pipeline that are going to be for our Salesforce integration.
[00:01:59.840 --> 00:02:03.000] Then another couple of Salesforce ones pending.
[00:02:03.160 --> 00:02:07.880] So we're going to go from one to five paying Salesforce customers probably over the course of a month.
[00:02:07.880 --> 00:02:10.440] And MRR is just hopping up.
[00:02:10.440 --> 00:02:13.320] We've got a couple agencies now that are really growing.
[00:02:13.320 --> 00:02:15.800] And so we've got some nice expansion revenue with them.
[00:02:15.800 --> 00:02:18.200] And this feels like the beginning of a big jump.
[00:02:18.200 --> 00:02:24.680] So it was like three months of pretty flat bouncing around, like just hovering around an under 10K month.
[00:02:24.680 --> 00:02:27.240] And then all of a sudden it has just popped.
[00:02:27.240 --> 00:02:29.080] And I feel like this is going to be another good month.
[00:02:29.080 --> 00:02:30.680] And then if this continues through to December.
[00:02:30.680 --> 00:02:33.080] So anyway, feeling really excited.
[00:02:33.080 --> 00:02:41.720] And it's funny, like I was after those three months of flat revenue, I was genuinely wondering if I was making the right decisions because I was just spending money and spending money and spending money.
[00:02:41.720 --> 00:02:46.040] But right now, it feels like those bets are paying off.
[00:02:46.040 --> 00:02:51.400] I feel more confident than I ever have that this might work.
[00:02:52.360 --> 00:03:02.440] So it sounds like things have, I don't know, turned a corner may not be the right way to put it, but were you, you weren't, were you flat, relatively flat for three months?
[00:03:02.440 --> 00:03:09.800] 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?
[00:03:09.800 --> 00:03:10.840] Yeah, definitely.
[00:03:11.400 --> 00:03:15.960] We, I mean, there were a few things that happened at once when we got into Tiny Seed.
[00:03:15.960 --> 00:03:22.200] And, you know, I was spending a lot of time shutting down my old agency, which now I can say officially, we have no clients left.
[00:03:22.200 --> 00:03:23.800] And I talked to my accountant.
[00:03:23.800 --> 00:03:27.160] We like, here's the roadmap for dissolution of the entity, all that.
[00:03:27.160 --> 00:03:28.200] Like, so that's really happening.
[00:03:28.200 --> 00:03:29.400] So that was a little bit of a distraction.
[00:03:29.400 --> 00:03:32.200] I was also a little nervous to spend the money.
[00:03:32.200 --> 00:03:35.400] It was like the most money I'd ever seen in a bank account before.
[00:03:35.400 --> 00:03:38.920] And so, you know, this kind of evolutionary instinct of like hoard.
[00:03:39.080 --> 00:03:40.440] And then also like how to spend it.
[00:03:40.440 --> 00:03:42.200] And so it took time to spend some of it.
[00:03:42.200 --> 00:03:44.960] So while all that was happening for a few months, revenue was flat.
[00:03:44.960 --> 00:03:47.360] We had a little bit of new customers, but a little bit of churn.
[00:03:44.840 --> 00:03:49.120] And so then I was starting to get anxious about that.
[00:03:49.280 --> 00:03:51.280] And I was questioning, like, do I know how to do this?
[00:03:51.280 --> 00:03:54.320] Like, actually, or did I only build like a pretty good idea?
[00:03:54.320 --> 00:03:58.960] And then I don't actually know how to run a software company because I technically don't know how to run a software company.
[00:03:58.960 --> 00:04:00.160] I'm learning right now how to do it.
[00:04:00.160 --> 00:04:03.680] But then September was our highest month ever, followed by October, followed by November.
[00:04:03.680 --> 00:04:06.480] And now it's December again, higher month ever.
[00:04:06.480 --> 00:04:10.320] And the anchor for that is an annual $20,000 contract.
[00:04:10.320 --> 00:04:13.760] I've never signed an annual contract worth this much before.
[00:04:13.760 --> 00:04:17.120] We had one earlier annual contract a couple months ago, but it was just for $5,000.
[00:04:17.120 --> 00:04:18.880] So this is like, we went through the process.
[00:04:18.880 --> 00:04:19.680] We went through procurement.
[00:04:19.680 --> 00:04:20.640] We went through legal.
[00:04:20.640 --> 00:04:23.680] I had the privilege of paying our attorneys to review the documents.
[00:04:23.680 --> 00:04:31.600] And a lot of things that I had just invested in around security and stuff when I was doing the questionnaires, I was actually like checking the boxes of like, yes, we literally are doing these practices.
[00:04:31.600 --> 00:04:36.880] Whereas before I spun out App on Sync, I had gotten a security questionnaire and like I didn't even know.
[00:04:36.880 --> 00:04:41.200] I looked back at that old spreadsheet and I didn't even really understand what they were asking me.
[00:04:41.520 --> 00:04:48.400] Like there were things where they asked and I was like, I literally just didn't understand it.
[00:04:48.400 --> 00:04:53.760] And now like a much, much, much longer, more complex procurement form.
[00:04:53.760 --> 00:04:55.360] I not only knew it, but we were doing it.
[00:04:55.360 --> 00:04:58.000] And so that just felt like, oh, okay, we're playing a different game.
[00:04:58.000 --> 00:05:03.120] It felt like I could one day have a salesperson doing this and not me.
[00:05:03.120 --> 00:05:11.840] And so that just felt like really big progress, even though they still haven't, they haven't paid us yet, but it's net 30 and hopefully they're going to pay the invoice.
[00:05:11.840 --> 00:05:12.640] And yeah.
[00:05:12.640 --> 00:05:15.680] So that felt like the beginning of like, this is more of a software company.
[00:05:15.680 --> 00:05:16.080] We're growing.
[00:05:16.080 --> 00:05:17.520] We've got these big contracts.
[00:05:17.520 --> 00:05:21.280] And we can like, I can have that conversation with the procurement team.
[00:05:21.280 --> 00:05:26.400] I understand now a little bit of when they're pushing back and what they're pushing back on and what we can say yes to and no to.
[00:05:26.400 --> 00:05:30.000] And all that was just like, I had no idea a year ago at all.
[00:05:30.440 --> 00:05:35.240] For a long time, I've been saying, you know, if you have to go through procurement, $25,000 minimum ACV.
[00:05:35.240 --> 00:05:40.120] And now I think I'm up to about given inflation, literally, and just how many years it's been.
[00:05:40.120 --> 00:05:42.920] It's like, I think it might be 30 or 35 is kind of my number.
[00:05:42.920 --> 00:05:44.200] It's almost three grand a month.
[00:05:44.200 --> 00:05:46.040] That makes it $2,500, you know, and there.
[00:05:46.040 --> 00:05:47.880] So I got to raise my prices.
[00:05:48.200 --> 00:05:48.840] I think so.
[00:05:48.840 --> 00:06:01.480] 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, you know, all that happens, it's expensive when you pay your own lawyers to deal with this.
[00:06:04.040 --> 00:06:07.320] Harris started the SOC2 process about three months ago.
[00:06:07.320 --> 00:06:13.240] It can be tedious and expensive, and many early stage founders want to avoid it as long as possible.
[00:06:13.240 --> 00:06:17.240] But it can also be a big unlock for closing bigger deals.
[00:06:20.120 --> 00:06:24.120] So we're basically at the finish line and ready to start the audit.
[00:06:24.120 --> 00:06:29.160] We implemented a lot of changes and actually they've been really beneficial.
[00:06:29.160 --> 00:06:31.320] So I'm a non-technical founder.
[00:06:31.320 --> 00:06:46.120] There were a lot of things that maybe an engineer founder would have set up from the get-go that, I mean, I've just always said, do our, 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 like give you extra stuff to do.
[00:06:46.120 --> 00:06:49.240] And so he was just, you know, pushing to production, basically.
[00:06:49.240 --> 00:06:55.880] And there were practices that SOC2 requires that in hindsight, we've implemented them and it's been really good.
[00:06:55.880 --> 00:07:01.240] So like one of them is we have a staging server and so we test every feature before it goes to production.
[00:07:01.240 --> 00:07:04.600] And I know that we probably should have been doing that the whole time, but you know, whatever.
[00:07:04.600 --> 00:07:06.520] It wasn't, we didn't even have customers in the beginning, right?
[00:07:06.520 --> 00:07:08.440] So it kind of like wasn't worth it.
[00:07:08.440 --> 00:07:11.640] Another thing was security, which has actually already benefited us.
[00:07:11.640 --> 00:07:23.120] We have now like 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 like a cross-scripting attack.
[00:07:23.120 --> 00:07:27.840] And so we caught that because we have this add-on and engineer caught it.
[00:07:27.840 --> 00:07:31.040] We troubleshot it and came up with a fix.
[00:07:31.040 --> 00:07:33.920] It turns out there was no like malicious issue, but there could have been.
[00:07:33.920 --> 00:07:39.680] And so basically our infrastructure was doing its job and none of that was in place prior to starting SOC2.
[00:07:39.680 --> 00:07:42.720] And so then we were able to tell our customers like, hey, we've identified this issue.
[00:07:42.720 --> 00:07:44.400] Here's how we're now solving it.
[00:07:44.400 --> 00:07:47.200] It's actually not something we can control because we're just getting this data.
[00:07:47.200 --> 00:07:50.560] We're getting these webhook payloads and then we got to figure out how to deal with them.
[00:07:50.560 --> 00:08:00.800] And we want to make sure because we have right access to yours or your customers' CRM, like Salesforce and HubSpot, we need to make sure that we're being diligent about what we're passing along, basically.
[00:08:00.800 --> 00:08:01.760] And so it made us look really good.
[00:08:01.760 --> 00:08:05.440] And like we have a status page, which we didn't before, but we have that because of SOC2.
[00:08:05.440 --> 00:08:10.480] And so I said, you know, here's the write-up of the incident and here's the updates and here's how we resolved it.
[00:08:10.480 --> 00:08:15.200] And all of those things just felt like as we were doing it, it just felt really good.
[00:08:15.200 --> 00:08:22.000] And I feel like it established credibility with customers because, you know, we're between these big platforms.
[00:08:22.000 --> 00:08:26.480] And so we kind of have to prove ourselves of like, how do I know you're not messing up on this?
[00:08:26.480 --> 00:08:29.360] Like, who, who, you know, who, who are you really?
[00:08:29.600 --> 00:08:30.400] You know, to me.
[00:08:30.400 --> 00:08:33.200] And we've closed quite a bit of business because of it.
[00:08:33.200 --> 00:08:37.760] Like we have gone through this big enterprise deal we just talked about, but also quite a few others.
[00:08:37.760 --> 00:08:41.040] I've just sent them a link to our trust center and they're like, okay, great.
[00:08:41.040 --> 00:08:42.800] Yep, we can see you've got a lot of stuff in place.
[00:08:42.800 --> 00:08:49.600] And so, I mean, it has investing in that has improved our product, improved our customer support, and increased our sales.
[00:08:49.600 --> 00:08:54.400] It just like forced us to grow up a little bit in ways where I want to take the company.
[00:08:54.400 --> 00:08:58.720] Like I wanted to be doing multiple millions in ARR.
[00:08:58.720 --> 00:09:02.520] And so it's like, okay, we're going to have to grow up in these areas.
[00:08:59.840 --> 00:09:06.920] And so it kind of forced that to happen in a structured way where I don't know.
[00:09:07.000 --> 00:09:07.800] I'm really glad about it.
[00:09:07.800 --> 00:09:17.560] People, 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 being having been a really important decision at the time.
[00:09:17.560 --> 00:09:20.360] Yeah, I would gripe about it because I hate that kind of stuff.
[00:09:20.600 --> 00:09:21.320] I don't.
[00:09:21.640 --> 00:09:24.680] You're building a business and you come from the sales side.
[00:09:24.680 --> 00:09:27.880] And you know that to make sales and to get big fast, you're going to have to close big deals.
[00:09:27.880 --> 00:09:30.920] And to close big deals, you're going to need SOC 2 in this space.
[00:09:31.080 --> 00:09:32.280] It's just inevitable.
[00:09:32.280 --> 00:09:35.720] And so you have just accepted it like a mature adult.
[00:09:35.720 --> 00:09:49.000] 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, you know, and I'm like, I want to do product and like design stuff and make sure this is all elegant.
[00:09:49.000 --> 00:09:51.400] And so I'd be like, ah, this SOC 2, why do I need this?
[00:09:51.400 --> 00:09:52.440] This is just a headache.
[00:09:52.440 --> 00:09:56.920] But you have just on this particular instance, you know, I'm sure there are other ones where you take the opposite tack.
[00:09:56.920 --> 00:09:58.760] But that's, and that's what we see within Tiny Seed.
[00:09:58.760 --> 00:10:04.040] There are certain founders who are more like me, who are like, God, kicking in, screaming, just scratching and clawing.
[00:10:04.040 --> 00:10:07.640] You have to pull, you know, for my cold dead hands than not, not going to SOC 2.
[00:10:07.640 --> 00:10:10.840] And then there are those who are just like, nah, it's not fun.
[00:10:10.840 --> 00:10:20.200] But I also know that I'll probably close, you know, literally hundreds of thousands of dollars in ACV next year if I have this, that I will not if I don't.
[00:10:20.200 --> 00:10:24.760] And so that becomes the question that a lot of founders have to ask themselves.
[00:10:24.760 --> 00:10:25.640] Yeah, for sure.
[00:10:25.640 --> 00:10:28.360] And it's given me a better lens to understand what's happening with our product.
[00:10:28.360 --> 00:10:32.680] Like I understand technically much better how our product is working because of it.
[00:10:34.600 --> 00:10:42.800] We've been talking about getting SOC 2 certified, a process that doesn't come cheap, but that's just one piece of Harris's growing expenses.
[00:10:42.800 --> 00:10:48.960] With a young family at home and a business that's scaling up, every financial decision carries extra weight.
[00:10:44.840 --> 00:10:52.080] I wanted to understand how he's navigating these waters.
[00:10:53.360 --> 00:10:56.720] Before, I'd ran an agency for five years.
[00:10:56.720 --> 00:11:01.520] It was profitable because it had to be, but it was never like a breakout success.
[00:11:01.840 --> 00:11:03.680] You know, I was never able to fully hand things off.
[00:11:03.680 --> 00:11:05.920] I was never really able to take a vacation.
[00:11:05.920 --> 00:11:09.280] It was always hard still, even though it was financially successful.
[00:11:09.280 --> 00:11:12.400] But also, I had an LLC that had a sub-ass selection.
[00:11:12.400 --> 00:11:14.080] So I was able to pay myself in a different way.
[00:11:14.080 --> 00:11:14.880] I had distributions.
[00:11:14.880 --> 00:11:16.880] I had a lot more flexibility.
[00:11:17.200 --> 00:11:20.720] Starting up on Sync, I wanted it to be a proper software company.
[00:11:20.720 --> 00:11:22.720] And this wasn't like a tiny seed requirement.
[00:11:22.720 --> 00:11:32.960] I 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.
[00:11:32.960 --> 00:11:35.840] And it's like, I just want this to be a fresh, solid start.
[00:11:35.840 --> 00:11:42.720] And so that change, I did not fully realize how much that shift of like, okay, now I'm only getting paid a salary because Up on Sync is a C corporation.
[00:11:42.720 --> 00:11:44.560] And so now we have payroll through ADP.
[00:11:44.560 --> 00:11:45.600] And that's it.
[00:11:45.600 --> 00:11:47.920] That money that I get paid, that is my money.
[00:11:47.920 --> 00:11:56.080] And I was just used to before being like, well, you know, I can take a distribution out of here and make sure I can cover this or that unexpected expense.
[00:11:56.080 --> 00:12:07.680] So that introduced like a pressure that I didn't, I think, think through fully at the time because I had five years of not having that kind of constraint that I sort of forgot what it was like.
[00:12:08.480 --> 00:12:10.000] I could always figure it out, basically.
[00:12:10.000 --> 00:12:10.640] I always found a way.
[00:12:11.120 --> 00:12:12.880] I landed a bigger client or this or that.
[00:12:12.880 --> 00:12:16.000] I started spending the tiny seed money more to get the growth going.
[00:12:16.000 --> 00:12:18.800] And I would say, like, both of those investments have been worthwhile.
[00:12:18.960 --> 00:12:20.720] Developer is very productive.
[00:12:20.720 --> 00:12:22.000] He's doing great.
[00:12:22.000 --> 00:12:22.960] We talk very little.
[00:12:22.960 --> 00:12:24.160] He just cranks on stuff.
[00:12:24.160 --> 00:12:24.800] We check in.
[00:12:24.800 --> 00:12:26.880] It's a really great relationship.
[00:12:26.680 --> 00:12:29.960] Um, and I can tell the difference, him going to 40 hours a week.
[00:12:29.960 --> 00:12:34.120] The productivity is like way, way outstripping the like percentage increase of time that he's working.
[00:12:29.760 --> 00:12:36.120] And then the CSM has been good because it's freed me up.
[00:12:36.200 --> 00:12:38.840] So, he's focusing on onboarding, getting new users.
[00:12:38.840 --> 00:12:41.560] That hire has worked out so far really, really well.
[00:12:41.560 --> 00:12:47.720] We went through Dynamite Jobs recruiting board, remote first recruiting, and they found a very good candidate.
[00:12:47.720 --> 00:12:52.280] I think he's really taking ownership of things, he's just like running with it more.
[00:12:52.600 --> 00:12:54.440] And that's freed me up to focus more on sales.
[00:12:54.440 --> 00:12:58.360] I think that's why these last couple months have been getting better in terms of sales.
[00:12:58.360 --> 00:13:09.320] I think that with these three people, me and CSM, an engineer, my goal is that we get to 30K MRR, and that would give us plenty of headroom at this point to be default alive.
[00:13:09.480 --> 00:13:13.560] I'm just like kind of trying to run as hard and as fast as I can to get to that.
[00:13:13.560 --> 00:13:17.880] I could lower that number though if I reduce my own drag on the business.
[00:13:17.880 --> 00:13:22.760] So, in like on the home front, I've been implementing a budgeting app called YNAB.
[00:13:22.920 --> 00:13:24.120] You need a budget.
[00:13:24.120 --> 00:13:31.880] And we now have four months of my wife and I have four months of budgeting data of our own spending, like down to the scent.
[00:13:31.880 --> 00:13:35.000] I did my own books for a while and I took like accounting classes in business school.
[00:13:35.000 --> 00:13:37.480] So, like, fortunately, that's actually been pretty easy to do.
[00:13:37.480 --> 00:13:39.480] It just has to sit down and do it.
[00:13:39.480 --> 00:13:47.560] So, I'm trying to figure out how do we tighten up spending on the personal side so that I can reduce my salary so that I can extend that runway a little bit more.
[00:13:47.560 --> 00:13:51.480] But, yeah, right now, I'm thinking about this like a lot right now.
[00:13:51.480 --> 00:13:54.440] And we're good now, but I like projecting out six months.
[00:13:54.440 --> 00:13:57.960] I'm kind of like, okay, well, would I do a revenue-based financing?
[00:13:57.960 --> 00:13:59.880] Would I pull some money out of retirement?
[00:13:59.880 --> 00:14:01.000] We're not running out of money yet.
[00:14:01.000 --> 00:14:10.440] We've got money in the bank, but because I have this salary, like 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.
[00:14:10.440 --> 00:14:13.720] It's totally like connected.
[00:14:13.880 --> 00:14:20.720] And, you know, we had a little bit of churn, and it's really hard to not be like, get too down about that because it feels like, oh, everything's in jeopardy.
[00:14:20.720 --> 00:14:22.480] You know, like, I was close and now I'm further.
[00:14:22.480 --> 00:14:26.320] And so there's that, like, yeah, it just feels like everything is all in one basket.
[00:14:26.320 --> 00:14:33.440] Man, it's tenuous because you grow another five or 10K MRR and you're like, well, finally, we're break even or we have a profit.
[00:14:33.440 --> 00:14:36.800] Oh, now I'm going, but I need to hire an engineer to keep up with XYZ.
[00:14:36.800 --> 00:14:45.920] So, you know, I'm not saying it never goes away, but it really is, even when you're doing a million, two million, three million a year, it's always this balancing act.
[00:14:45.920 --> 00:14:54.320] 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, you know, out of the bank account into your personal one.
[00:14:54.320 --> 00:14:56.240] Like, you know, there's still a stress.
[00:14:56.240 --> 00:15:05.120] But the thing that as a founder, you have to keep in mind is like, don't sacrifice your own personal finances or your families in order to get the company going.
[00:15:05.520 --> 00:15:06.960] But yes, there is risk.
[00:15:06.960 --> 00:15:08.320] So how do you, you know, how do you balance that?
[00:15:08.320 --> 00:15:09.120] That's the hard part.
[00:15:09.120 --> 00:15:15.760] That's why founders, as a rule, tend to have more anxiety and stress in their lives than employees of big companies.
[00:15:15.760 --> 00:15:20.640] But employees of big companies tend to have a lot more depression than founders do.
[00:15:20.640 --> 00:15:23.760] And this is, there's a, there's multiple studies that have verified that.
[00:15:23.760 --> 00:15:26.960] Sherry, my wife, has talked about this in a few talks.
[00:15:26.960 --> 00:15:28.080] It is more stressful.
[00:15:28.080 --> 00:15:34.560] The upside is significantly higher, but that does not come without some risk and some uncertainty.
[00:15:34.560 --> 00:15:36.560] And those two things are tough.
[00:15:36.560 --> 00:15:41.760] And they're tough on you and they're tough on your, you know, your partner or significant other.
[00:15:41.760 --> 00:15:48.880] 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.
[00:15:48.880 --> 00:15:54.160] And you know, if you sell this company or shut it down for years from now, you never want to do it again.
[00:15:54.160 --> 00:15:56.160] Or you can not worry at all about it.
[00:15:56.160 --> 00:16:00.760] And you can be like some people and they take out $50,000, $60,000, $70,000 of credit card debt to start their company.
[00:15:59.840 --> 00:16:04.680] And they're not nearly risk averse enough, you know.
[00:16:04.840 --> 00:16:18.280] And it's like there's some balance in between of like, 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?
[00:16:18.280 --> 00:16:19.320] Oh, totally.
[00:16:19.320 --> 00:16:23.640] I mean, I think fortunately, I've got like some levers I can pull.
[00:16:23.640 --> 00:16:30.200] Like, I mean, to go into my personal finances a little bit, like I've got like a universal life insurance policy that I had set up like when we first got married.
[00:16:30.200 --> 00:16:32.120] It's like, okay, well, let's cash that out.
[00:16:32.120 --> 00:16:35.480] Let's set up a term policy that'll actually pay out way more.
[00:16:35.480 --> 00:16:38.200] And then, okay, I've got that little bit to pay off some debt.
[00:16:38.200 --> 00:16:45.000] So now I'm reducing my month-to-month debt servicing that I've got in this area, better insurance than I had before.
[00:16:45.000 --> 00:16:51.720] So it's like little like levers like that that I'm pulling in a few different areas to kind of, and then I mean, there's hope on the horizon currently.
[00:16:51.720 --> 00:16:57.800] I know for a fact that 35% of our income goes to childcare, but we won't have young children forever.
[00:16:57.800 --> 00:16:59.720] School is on the horizon.
[00:16:59.720 --> 00:17:18.440] And so it's like, okay, it's possible that, you know, in three years, we're at MicroConf and I'm like, Rob, drinks are on me because, you know, the company's ripping and we just freed up multiple, multiple thousands of dollars a month in free cash flow that aren't going towards childcare.
[00:17:18.440 --> 00:17:23.800] So like, I do, I have that on the horizon that I think is like a reasonable thing to look forward to.
[00:17:23.800 --> 00:17:28.440] It's not like I'm going to, maybe I'll be on a boat, but it's not like I'm going to be a hundred millionaire, whatever.
[00:17:28.440 --> 00:17:31.560] Like that feels like a reasonable thing to, if I could just get there.
[00:17:31.560 --> 00:17:33.880] So that's kind of my mindset right now.
[00:17:33.880 --> 00:17:36.920] Like we've gotten really far in a short amount of time.
[00:17:36.920 --> 00:17:38.520] So I think that we can, I think I can get there.
[00:17:38.520 --> 00:17:39.080] I just have to.
[00:17:39.720 --> 00:17:40.920] It should get easier.
[00:17:40.920 --> 00:17:46.960] I mean, you are still very early in this business and the early days, everything's fragile.
[00:17:44.040 --> 00:17:53.920] Like even your knowledge and confidence that the business is going to work is pretty fragile.
[00:17:53.920 --> 00:17:56.320] Your product market fit is really fragile.
[00:17:56.320 --> 00:17:58.080] Your sales process is fragile.
[00:17:58.080 --> 00:18:00.560] You're thinking of like, who is this revenue going to stick around?
[00:18:00.560 --> 00:18:01.680] Is it going to continue to grow?
[00:18:01.680 --> 00:18:03.120] All of that's fragile still.
[00:18:03.120 --> 00:18:06.640] And that does solidify as the company matures.
[00:18:10.480 --> 00:18:15.280] Harris has talked before about expanding to other CRMs outside of HubSpot.
[00:18:15.280 --> 00:18:18.320] One of his newest missions was to integrate Salesforce.
[00:18:18.320 --> 00:18:20.720] And I wanted to see how that was going.
[00:18:23.280 --> 00:18:34.640] Well, so, okay, I didn't cheat, but I did maybe bend the rules of what like maybe you are thinking a Salesforce integration is because there's two ways to integrate with Salesforce.
[00:18:34.640 --> 00:18:38.720] And we did a connected app, which is essentially like a private unlisted app.
[00:18:38.720 --> 00:18:41.360] And so that allowed us, and this is what we did with HubSpot too.
[00:18:41.360 --> 00:18:43.680] It allows us to sell to Salesforce customers.
[00:18:43.680 --> 00:18:51.840] They just basically create their own like authorization for our web server to like hit their Salesforce account.
[00:18:51.840 --> 00:18:53.040] So that was how we moved so fast.
[00:18:53.040 --> 00:18:59.120] And then the other thing we did is we started with a tiny, tiny, tiny footprint of what it does.
[00:18:59.120 --> 00:19:04.800] And so we just solved like a very basic problem of like, we log emails as activities.
[00:19:04.800 --> 00:19:05.600] Do you want that?
[00:19:05.600 --> 00:19:07.920] And enough people were saying, yeah, that they've like started paying.
[00:19:07.920 --> 00:19:09.680] So we have multiple paying customers.
[00:19:09.680 --> 00:19:15.760] We've got like a mid-market company that we're in procurement process with now who wants that.
[00:19:15.760 --> 00:19:20.160] And then another one who has said, like, hey, I'm going to sign up for this probably in the next week.
[00:19:20.160 --> 00:19:32.360] So I think that we'll go from zero dollars in Salesforce revenue to probably like $2K MRR probably by the time we hit January, all of that closing basically over the course of like a month.
[00:19:32.440 --> 00:19:42.120] And then if we do that, you know, if all of our other numbers stay the same, I'm just doing quick calculator math here, you know, that'll end up being like 15% of our revenue.
[00:19:42.120 --> 00:19:43.640] So that's pretty cool.
[00:19:43.640 --> 00:19:48.120] But we're using Salesforce like brand as distribution, but not the app exchange.
[00:19:48.120 --> 00:19:49.320] The same thing we did with HubSpot.
[00:19:49.320 --> 00:19:53.800] Like I talk about on LinkedIn and I talk about other agencies and I say, if you use HubSpot, we can support you.
[00:19:53.800 --> 00:19:57.480] But the HubSpot thing, I was really, really, really, really proud of getting that.
[00:19:57.480 --> 00:19:59.000] And that was cool.
[00:19:59.000 --> 00:20:03.800] But we were selling the HubSpot app for over a year before we were in the marketplace.
[00:20:03.800 --> 00:20:06.680] And I think we're going to do the same thing with Salesforce agency.
[00:20:06.920 --> 00:20:08.680] That's moving fast and getting a V1 out there.
[00:20:08.680 --> 00:20:12.200] And then you built thousands and thousands of MRR.
[00:20:12.200 --> 00:20:19.240] I mean, you could have supported yourself almost full time on the business and you didn't have to wait for any of that, right?
[00:20:19.240 --> 00:20:20.840] And this is what the best entrepreneurs do.
[00:20:21.400 --> 00:20:24.360] They get it done real fast and then they turn around and say, all right, well, what's a V2?
[00:20:24.360 --> 00:20:27.560] Well, V2 is getting in the app marketplace because then we get promotion and all that.
[00:20:27.560 --> 00:20:32.360] I mean, you got into the app market, even the HubSpot app marketplace, it felt fast to me.
[00:20:32.360 --> 00:20:33.560] I don't know what the timeline was.
[00:20:33.880 --> 00:20:35.560] Oh, yeah, it only took like two weeks.
[00:20:35.560 --> 00:20:36.600] Because we were so ready.
[00:20:36.600 --> 00:20:41.560] They were like blew past their paying customers on it.
[00:20:41.560 --> 00:20:45.960] Normally you go in the app marketplace with no customers and then they're like, nope, testing for months, right?
[00:20:45.960 --> 00:20:48.680] And you need to have this many beta users and you already used it through it.
[00:20:48.680 --> 00:20:50.120] That's another exactly.
[00:20:50.120 --> 00:20:55.720] And you said, and I quote, we're the first smart lead integration in the HubSpot app marketplace.
[00:20:55.720 --> 00:20:58.360] And you sounded really proud of that, you know?
[00:20:58.360 --> 00:20:58.680] Yeah.
[00:20:58.680 --> 00:21:00.680] Yeah, before even SmartLead themselves.
[00:21:00.680 --> 00:21:00.920] Yeah.
[00:21:01.160 --> 00:21:04.600] Before their own integration, you beat SmartLead.
[00:21:04.600 --> 00:21:07.720] So that's got to be a pretty big point of pride for you.
[00:21:07.720 --> 00:21:08.360] Oh, for sure.
[00:21:08.360 --> 00:21:08.760] Yeah, yeah.
[00:21:08.760 --> 00:21:10.280] I mean, I think we're shipping really fast.
[00:21:10.280 --> 00:21:16.160] And I was in a chat with the founder of SmartLead, and he was like, you ship, which they have a great engineering team.
[00:21:14.600 --> 00:21:21.120] So I know he really means that as a compliment, you know, I mean, in their world, they really value engineering.
[00:21:21.200 --> 00:21:22.720] So yeah, we move fast.
[00:21:22.720 --> 00:21:26.880] And we've got two other sales engagement platforms that I think are going to potentially open up market for us.
[00:21:26.880 --> 00:21:31.040] Like it's the same core product, but competitors to SmartLead.
[00:21:31.280 --> 00:21:34.400] And I think, again, we will be the first integrations listed for those tools.
[00:21:34.400 --> 00:21:43.840] And I think that when we move, like our positioning is going to change to be like, hey, if you're using one of any of these app on tools, we'll be the one that gets it in your CRM the right way.
[00:21:43.840 --> 00:21:45.280] I think we'll be able to charge more.
[00:21:45.280 --> 00:21:46.880] That's kind of like what's on the horizon.
[00:21:46.880 --> 00:21:53.040] But I think that like this play that we just ran SmartLead, I think we're going to run twice again for two other tools.
[00:21:53.040 --> 00:21:56.160] And now I've got people being like, do you support Lemlist?
[00:21:56.160 --> 00:21:56.800] Do you support this?
[00:21:56.800 --> 00:21:57.440] Do you support that?
[00:21:57.440 --> 00:22:03.040] And so we're starting to get a waitlist forming for other tools.
[00:22:03.040 --> 00:22:12.960] And that, yeah, that just like kind of feels like to me, again, like we're in these like more advanced stages of becoming a real company.
[00:22:13.120 --> 00:22:22.400] Call that market pull, where it's like, and you're getting data because you're like, ooh, we have three requests for limb list and we have two for this other tool.
[00:22:22.400 --> 00:22:25.760] I don't know the space well enough to know we know what other tools are, but two for this other tool.
[00:22:25.760 --> 00:22:31.440] 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, you know?
[00:22:31.440 --> 00:22:36.400] And so now you have all the CRMs on one side and you have all the wet, cold email tools, I guess, on the other side, right?
[00:22:36.400 --> 00:22:37.280] That's what you're thinking.
[00:22:37.680 --> 00:22:40.000] But could be LinkedIn, could also be phones.
[00:22:40.000 --> 00:22:40.480] Yep.
[00:22:40.480 --> 00:22:41.680] So there's a lot.
[00:22:42.000 --> 00:22:43.600] There's a lot to be done here.
[00:22:43.600 --> 00:22:53.600] 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?
[00:22:53.600 --> 00:22:54.800] Because you were early, right?
[00:22:54.800 --> 00:22:56.480] We don't know if the business is going to work.
[00:22:56.480 --> 00:22:58.160] Do we think that Harris can do this?
[00:22:58.160 --> 00:23:00.760] And the answer was, yeah, I think he can do it.
[00:23:00.760 --> 00:23:02.360] And then why did we invest in the business?
[00:22:59.840 --> 00:23:04.680] Because it had traction, it had people that wanted to pay you.
[00:23:05.000 --> 00:23:10.520] And we see, I see the potential of this to be a seven or eight-figure ARR company.
[00:23:10.520 --> 00:23:13.160] Not with the initial product you had.
[00:23:13.160 --> 00:23:14.280] You know, it was what?
[00:23:14.280 --> 00:23:16.200] Smart leads to HubSpot, and it was very simple.
[00:23:16.200 --> 00:23:18.040] And it was first zaps, and then you had someone write code.
[00:23:18.040 --> 00:23:20.120] You know, I mean, that's not an eight-figure business.
[00:23:20.120 --> 00:23:28.760] But all that the vision that you're starting to paint here and the request, the market pull you're starting to get, that absolutely could do, could do 10 million or more in ARR.
[00:23:28.760 --> 00:23:30.040] Yeah, I believe so.
[00:23:30.040 --> 00:23:33.000] And I will say, I think this to me, this is why, like, well, Tiny Seed is different.
[00:23:33.000 --> 00:23:36.120] It is still fundamentally a venture endeavor.
[00:23:36.120 --> 00:23:41.240] Like, the risk of investing at the time, I mean, it reminds me of like when my wife decided to marry me.
[00:23:41.240 --> 00:23:42.440] It was like, rest of your life?
[00:23:42.520 --> 00:23:43.240] Are you like, are you sure?
[00:23:43.640 --> 00:23:44.200] Potential.
[00:23:44.200 --> 00:23:45.560] You saw potential.
[00:23:45.560 --> 00:23:48.520] Yeah, I'm not sure that I would marry me at this point.
[00:23:48.760 --> 00:23:51.720] We got married, not super young, but you know, it was a while ago.
[00:23:51.880 --> 00:23:53.080] We've been married for a long time.
[00:23:53.080 --> 00:23:55.560] But yeah, so it's fundamentally, there was a risk there, you know?
[00:23:55.560 --> 00:24:00.040] And so, yeah, I feel like y'all took a chance on me, and it's been, it's been cool.
[00:24:00.040 --> 00:24:01.400] You're making good progress, man.
[00:24:01.640 --> 00:24:07.400] Looking ahead over the next one to three months, because you know, it will record in the next one to three months.
[00:24:07.400 --> 00:24:09.800] What are you most excited about?
[00:24:10.440 --> 00:24:13.640] I believe really firmly that we are ahead of the market.
[00:24:13.640 --> 00:24:25.800] I think that the users that we're signing up and the prospects we're talking to today represent like the very beginning of a big chunk of a bell curve of the market that's going to be changing its process.
[00:24:25.800 --> 00:24:35.640] Like, 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.
[00:24:35.640 --> 00:24:37.640] And they have said, like, okay, great.
[00:24:37.640 --> 00:24:39.880] What email tool should we use?
[00:24:39.880 --> 00:24:41.160] Like, I don't even care.
[00:24:41.160 --> 00:24:43.960] I just need the data that you're giving me.
[00:24:44.280 --> 00:24:57.840] And so, to have, to be taking customers from outreach, which is like a unicorn, arguably created the sales engagement platform category, to be taking users from them as a like connector app, which I think we're doing more than that or solving different problems than that.
[00:24:57.840 --> 00:24:59.120] To me, that's like a really big deal.
[00:24:59.120 --> 00:25:03.760] And we have got two customers, like one we just closed and another one that's about to close that were like this.
[00:25:03.760 --> 00:25:05.840] And they're like, whatever, however, we need to send the emails.
[00:25:05.840 --> 00:25:08.000] I just want the way that you're putting it in that system.
[00:25:08.000 --> 00:25:10.560] So, I think we just keep moving down that path.
[00:25:10.560 --> 00:25:13.840] I think there's going to be, I think there's a lot more people to come, basically.
[00:25:13.840 --> 00:25:15.840] And I think the people we're helping right now are early adopters.
[00:25:15.840 --> 00:25:18.560] And so, if that's true, then I think we're going to have really good mojo.
[00:25:18.560 --> 00:25:20.480] I think we've got some really good agency partners.
[00:25:20.480 --> 00:25:28.960] And I think that when we add, like, build out Salesforce and that 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'll start unlocking more pieces.
[00:25:28.960 --> 00:25:31.680] So, I'm really confident in that potential.
[00:25:31.680 --> 00:25:37.520] 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.
[00:25:37.520 --> 00:25:48.880] And so, I need to figure out like how to become a more mature product marketer to capture that because I talk to customers who get it, but I can't trust, I can't wait for everyone to get it.
[00:25:48.880 --> 00:25:53.360] I need to like, you know, so that, but that's where, I think that's where the opportunity is.
[00:25:53.360 --> 00:25:58.480] And I think that when I look at like where we're taking business from, it's not just people who are using Zapier right now.
[00:25:58.480 --> 00:26:03.920] It's, 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.
[00:26:03.920 --> 00:26:05.120] And you are.
[00:26:05.120 --> 00:26:08.160] That is like, okay, cool.
[00:26:08.480 --> 00:26:09.840] It's super motivating.
[00:26:10.160 --> 00:26:10.880] Outreach is fine.
[00:26:10.880 --> 00:26:11.840] Maybe we'll integrate with outreach.
[00:26:12.160 --> 00:26:16.640] I have no beef with them, like, whatever, you know, it's just, it's just B2B SaaS software, yeah, who cares?
[00:26:16.640 --> 00:26:19.920] But the competitive side of me is like, okay, yeah, like we're doing something.
[00:26:19.920 --> 00:26:20.720] We're making a mark.
[00:26:20.720 --> 00:26:23.760] We're getting people to switch, which is, which is cool.
[00:26:27.280 --> 00:26:32.120] What started as a simple connector app has evolved into something much more ambitious.
[00:26:32.440 --> 00:26:39.400] Harris is finding his product isn't just competing with simple automation tools, it's pulling customers away from industry giants.
[00:26:39.400 --> 00:26:46.760] And in today's market, where companies are scrutinizing every dollar spent on their tech stack, Outbound Sync seems to be resonating.
[00:26:46.760 --> 00:26:51.240] The question is, how far can this unexpected momentum take him?
[00:26:51.240 --> 00:26:54.200] Find out next time on Tiny Seed Tales.
[00:26:58.360 --> 00:27:00.360] I hope you enjoyed this episode.
[00:27:00.360 --> 00:27:12.040] 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've put together something special for you at tinyseed.com/slash bonus.
[00:27:12.040 --> 00:27:13.000] You should check it out.
[00:27:13.000 --> 00:27:15.400] I've never released anything like this before.
[00:27:15.400 --> 00:27:16.280] I hope you enjoy it.
[00:27:16.280 --> 00:27:19.080] It's at tinyseed.com/slash bonus.

Prompt 2: Key Takeaways

Now please extract the key takeaways from the transcript content I provided.

Extract the most important key takeaways from this part of the conversation. Use a single sentence statement (the key takeaway) rather than milquetoast descriptions like "the hosts discuss...". 

Limit the key takeaways to a maximum of 3. The key takeaways should be insightful and knowledge-additive. 

IMPORTANT: Return ONLY valid JSON, no explanations or markdown. Ensure:
- All strings are properly quoted and escaped
- No trailing commas
- All braces and brackets are balanced
Format: {"key_takeaways": ["takeaway 1", "takeaway 2"]}

Prompt 3: Segments

Now identify 2-4 distinct topical segments from this part of the conversation.

For each segment, identify:
- Descriptive title (3-6 words)  
- START timestamp when this topic begins (HH:MM:SS format)
- Double check that the timestamp is accurate - a timestamp will NEVER be greater than the total length of the audio
- Most important Key takeaway from that segment. Key takeaway must be specific and knowledge-additive.
- Brief summary of the discussion

IMPORTANT: The timestamp should mark when the topic/segment STARTS, not a range. Look for topic transitions and conversation shifts.

Return ONLY valid JSON. Ensure all strings are properly quoted, no trailing commas:
{
  "segments": [
    {
      "segment_title": "Topic Discussion", 
      "timestamp": "01:15:30",
      "key_takeaway": "main point from this segment",
      "segment_summary": "brief description of what was discussed"
    }
  ]
}

Timestamp format: HH:MM:SS (e.g., 00:05:30, 01:22:45) marking the START of each segment.

Prompt 4: Media Mentions

Now scan the transcript content I provided for ACTUAL mentions of specific media titles:

Find explicit mentions of:
- Books (with specific titles)
- Movies (with specific titles)  
- TV Shows (with specific titles)
- Music/Songs (with specific titles)

DO NOT include:
- Websites, URLs, or web services
- Other podcasts or podcast names

IMPORTANT: 
- Only include items explicitly mentioned by name. Do not invent titles.
- Valid categories are: "Book", "Movie", "TV Show", "Music"
- Include the exact phrase where each item was mentioned
- Find the nearest proximate timestamp where it appears in the conversation
- THE TIMESTAMP OF THE MEDIA MENTION IS IMPORTANT - DO NOT INVENT TIMESTAMPS AND DO NOT MISATTRIBUTE TIMESTAMPS
- Double check that the timestamp is accurate - a timestamp will NEVER be greater than the total length of the audio
- Timestamps are given as ranges, e.g. 01:13:42.520 --> 01:13:46.720. Use the EARLIER of the 2 timestamps in the range.

Return ONLY valid JSON. Ensure all strings are properly quoted and escaped, no trailing commas:
{
  "media_mentions": [
    {
      "title": "Exact Title as Mentioned",
      "category": "Book",
      "author_artist": "N/A",
      "context": "Brief context of why it was mentioned",
      "context_phrase": "The exact sentence or phrase where it was mentioned",
      "timestamp": "estimated time like 01:15:30"
    }
  ]
}

If no media is mentioned, return: {"media_mentions": []}

Full Transcript

[00:00:00.160 --> 00:00:04.960] We're back with episode three of season five of Tiny Seed Tales.
[00:00:04.960 --> 00:00:07.200] I hope you're enjoying the season so far.
[00:00:07.200 --> 00:00:13.840] Before we dive into the episode, I wanted to let you know that TinySeed applications are open for our fall 2025 batch.
[00:00:13.840 --> 00:00:25.360] 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.
[00:00:25.360 --> 00:00:29.600] If you know your metrics, the application only takes about 10 to 15 minutes to fill out.
[00:00:29.600 --> 00:00:31.920] Applications close on September 9th.
[00:00:31.920 --> 00:00:35.600] Get all the details at tinyseed.com/slash apply.
[00:00:35.600 --> 00:00:44.000] And even if you miss the application deadline, enter your email at tinyseed.com slash apply and you'll be notified next time we open applications.
[00:00:44.000 --> 00:00:45.280] Let's dive in.
[00:00:45.280 --> 00:00:48.000] I believe really firmly that we are ahead of the market.
[00:00:48.000 --> 00:00:58.560] I think that the users that we're signing up and the prospects we're talking to today represent like the very beginning of a big chunk of a bell curve of the market that's going to be changing its process.
[00:01:01.440 --> 00:01:07.440] Welcome back to Tiny Seed Tales, a series where I follow a founder through the roller coaster of building their startup.
[00:01:07.440 --> 00:01:15.600] I'm your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the startup accelerator for ambitious SaaS bootstrappers.
[00:01:15.600 --> 00:01:20.560] Here in season five, I've been talking to Harris Kenney, founder of Outbound Sync.
[00:01:20.880 --> 00:01:29.120] In our last episode, Harris moved on from a broad market approach to zeroing in on agencies helping clients with cold outreach.
[00:01:29.120 --> 00:01:34.080] Time will tell if the move paid off, but early indications are that it's working out.
[00:01:34.080 --> 00:01:40.240] Soon after closing the biggest contract in the history of his company, Harris sent me this audio message.
[00:01:40.560 --> 00:01:42.800] We just closed our first enterprise deal.
[00:01:42.800 --> 00:01:44.560] It was really nerve-wracking.
[00:01:44.560 --> 00:01:55.200] 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 Outbound Sync.
[00:01:55.520 --> 00:02:01.160] And then we've got like two other mid-market deals in pipeline that are going to be for our Salesforce integration.
[00:01:59.840 --> 00:02:03.000] Then another couple of Salesforce ones pending.
[00:02:03.160 --> 00:02:07.880] So we're going to go from one to five paying Salesforce customers probably over the course of a month.
[00:02:07.880 --> 00:02:10.440] And MRR is just hopping up.
[00:02:10.440 --> 00:02:13.320] We've got a couple agencies now that are really growing.
[00:02:13.320 --> 00:02:15.800] And so we've got some nice expansion revenue with them.
[00:02:15.800 --> 00:02:18.200] And this feels like the beginning of a big jump.
[00:02:18.200 --> 00:02:24.680] So it was like three months of pretty flat bouncing around, like just hovering around an under 10K month.
[00:02:24.680 --> 00:02:27.240] And then all of a sudden it has just popped.
[00:02:27.240 --> 00:02:29.080] And I feel like this is going to be another good month.
[00:02:29.080 --> 00:02:30.680] And then if this continues through to December.
[00:02:30.680 --> 00:02:33.080] So anyway, feeling really excited.
[00:02:33.080 --> 00:02:41.720] And it's funny, like I was after those three months of flat revenue, I was genuinely wondering if I was making the right decisions because I was just spending money and spending money and spending money.
[00:02:41.720 --> 00:02:46.040] But right now, it feels like those bets are paying off.
[00:02:46.040 --> 00:02:51.400] I feel more confident than I ever have that this might work.
[00:02:52.360 --> 00:03:02.440] So it sounds like things have, I don't know, turned a corner may not be the right way to put it, but were you, you weren't, were you flat, relatively flat for three months?
[00:03:02.440 --> 00:03:09.800] 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?
[00:03:09.800 --> 00:03:10.840] Yeah, definitely.
[00:03:11.400 --> 00:03:15.960] We, I mean, there were a few things that happened at once when we got into Tiny Seed.
[00:03:15.960 --> 00:03:22.200] And, you know, I was spending a lot of time shutting down my old agency, which now I can say officially, we have no clients left.
[00:03:22.200 --> 00:03:23.800] And I talked to my accountant.
[00:03:23.800 --> 00:03:27.160] We like, here's the roadmap for dissolution of the entity, all that.
[00:03:27.160 --> 00:03:28.200] Like, so that's really happening.
[00:03:28.200 --> 00:03:29.400] So that was a little bit of a distraction.
[00:03:29.400 --> 00:03:32.200] I was also a little nervous to spend the money.
[00:03:32.200 --> 00:03:35.400] It was like the most money I'd ever seen in a bank account before.
[00:03:35.400 --> 00:03:38.920] And so, you know, this kind of evolutionary instinct of like hoard.
[00:03:39.080 --> 00:03:40.440] And then also like how to spend it.
[00:03:40.440 --> 00:03:42.200] And so it took time to spend some of it.
[00:03:42.200 --> 00:03:44.960] So while all that was happening for a few months, revenue was flat.
[00:03:44.960 --> 00:03:47.360] We had a little bit of new customers, but a little bit of churn.
[00:03:44.840 --> 00:03:49.120] And so then I was starting to get anxious about that.
[00:03:49.280 --> 00:03:51.280] And I was questioning, like, do I know how to do this?
[00:03:51.280 --> 00:03:54.320] Like, actually, or did I only build like a pretty good idea?
[00:03:54.320 --> 00:03:58.960] And then I don't actually know how to run a software company because I technically don't know how to run a software company.
[00:03:58.960 --> 00:04:00.160] I'm learning right now how to do it.
[00:04:00.160 --> 00:04:03.680] But then September was our highest month ever, followed by October, followed by November.
[00:04:03.680 --> 00:04:06.480] And now it's December again, higher month ever.
[00:04:06.480 --> 00:04:10.320] And the anchor for that is an annual $20,000 contract.
[00:04:10.320 --> 00:04:13.760] I've never signed an annual contract worth this much before.
[00:04:13.760 --> 00:04:17.120] We had one earlier annual contract a couple months ago, but it was just for $5,000.
[00:04:17.120 --> 00:04:18.880] So this is like, we went through the process.
[00:04:18.880 --> 00:04:19.680] We went through procurement.
[00:04:19.680 --> 00:04:20.640] We went through legal.
[00:04:20.640 --> 00:04:23.680] I had the privilege of paying our attorneys to review the documents.
[00:04:23.680 --> 00:04:31.600] And a lot of things that I had just invested in around security and stuff when I was doing the questionnaires, I was actually like checking the boxes of like, yes, we literally are doing these practices.
[00:04:31.600 --> 00:04:36.880] Whereas before I spun out App on Sync, I had gotten a security questionnaire and like I didn't even know.
[00:04:36.880 --> 00:04:41.200] I looked back at that old spreadsheet and I didn't even really understand what they were asking me.
[00:04:41.520 --> 00:04:48.400] Like there were things where they asked and I was like, I literally just didn't understand it.
[00:04:48.400 --> 00:04:53.760] And now like a much, much, much longer, more complex procurement form.
[00:04:53.760 --> 00:04:55.360] I not only knew it, but we were doing it.
[00:04:55.360 --> 00:04:58.000] And so that just felt like, oh, okay, we're playing a different game.
[00:04:58.000 --> 00:05:03.120] It felt like I could one day have a salesperson doing this and not me.
[00:05:03.120 --> 00:05:11.840] And so that just felt like really big progress, even though they still haven't, they haven't paid us yet, but it's net 30 and hopefully they're going to pay the invoice.
[00:05:11.840 --> 00:05:12.640] And yeah.
[00:05:12.640 --> 00:05:15.680] So that felt like the beginning of like, this is more of a software company.
[00:05:15.680 --> 00:05:16.080] We're growing.
[00:05:16.080 --> 00:05:17.520] We've got these big contracts.
[00:05:17.520 --> 00:05:21.280] And we can like, I can have that conversation with the procurement team.
[00:05:21.280 --> 00:05:26.400] I understand now a little bit of when they're pushing back and what they're pushing back on and what we can say yes to and no to.
[00:05:26.400 --> 00:05:30.000] And all that was just like, I had no idea a year ago at all.
[00:05:30.440 --> 00:05:35.240] For a long time, I've been saying, you know, if you have to go through procurement, $25,000 minimum ACV.
[00:05:35.240 --> 00:05:40.120] And now I think I'm up to about given inflation, literally, and just how many years it's been.
[00:05:40.120 --> 00:05:42.920] It's like, I think it might be 30 or 35 is kind of my number.
[00:05:42.920 --> 00:05:44.200] It's almost three grand a month.
[00:05:44.200 --> 00:05:46.040] That makes it $2,500, you know, and there.
[00:05:46.040 --> 00:05:47.880] So I got to raise my prices.
[00:05:48.200 --> 00:05:48.840] I think so.
[00:05:48.840 --> 00:06:01.480] 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, you know, all that happens, it's expensive when you pay your own lawyers to deal with this.
[00:06:04.040 --> 00:06:07.320] Harris started the SOC2 process about three months ago.
[00:06:07.320 --> 00:06:13.240] It can be tedious and expensive, and many early stage founders want to avoid it as long as possible.
[00:06:13.240 --> 00:06:17.240] But it can also be a big unlock for closing bigger deals.
[00:06:20.120 --> 00:06:24.120] So we're basically at the finish line and ready to start the audit.
[00:06:24.120 --> 00:06:29.160] We implemented a lot of changes and actually they've been really beneficial.
[00:06:29.160 --> 00:06:31.320] So I'm a non-technical founder.
[00:06:31.320 --> 00:06:46.120] There were a lot of things that maybe an engineer founder would have set up from the get-go that, I mean, I've just always said, do our, 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 like give you extra stuff to do.
[00:06:46.120 --> 00:06:49.240] And so he was just, you know, pushing to production, basically.
[00:06:49.240 --> 00:06:55.880] And there were practices that SOC2 requires that in hindsight, we've implemented them and it's been really good.
[00:06:55.880 --> 00:07:01.240] So like one of them is we have a staging server and so we test every feature before it goes to production.
[00:07:01.240 --> 00:07:04.600] And I know that we probably should have been doing that the whole time, but you know, whatever.
[00:07:04.600 --> 00:07:06.520] It wasn't, we didn't even have customers in the beginning, right?
[00:07:06.520 --> 00:07:08.440] So it kind of like wasn't worth it.
[00:07:08.440 --> 00:07:11.640] Another thing was security, which has actually already benefited us.
[00:07:11.640 --> 00:07:23.120] We have now like 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 like a cross-scripting attack.
[00:07:23.120 --> 00:07:27.840] And so we caught that because we have this add-on and engineer caught it.
[00:07:27.840 --> 00:07:31.040] We troubleshot it and came up with a fix.
[00:07:31.040 --> 00:07:33.920] It turns out there was no like malicious issue, but there could have been.
[00:07:33.920 --> 00:07:39.680] And so basically our infrastructure was doing its job and none of that was in place prior to starting SOC2.
[00:07:39.680 --> 00:07:42.720] And so then we were able to tell our customers like, hey, we've identified this issue.
[00:07:42.720 --> 00:07:44.400] Here's how we're now solving it.
[00:07:44.400 --> 00:07:47.200] It's actually not something we can control because we're just getting this data.
[00:07:47.200 --> 00:07:50.560] We're getting these webhook payloads and then we got to figure out how to deal with them.
[00:07:50.560 --> 00:08:00.800] And we want to make sure because we have right access to yours or your customers' CRM, like Salesforce and HubSpot, we need to make sure that we're being diligent about what we're passing along, basically.
[00:08:00.800 --> 00:08:01.760] And so it made us look really good.
[00:08:01.760 --> 00:08:05.440] And like we have a status page, which we didn't before, but we have that because of SOC2.
[00:08:05.440 --> 00:08:10.480] And so I said, you know, here's the write-up of the incident and here's the updates and here's how we resolved it.
[00:08:10.480 --> 00:08:15.200] And all of those things just felt like as we were doing it, it just felt really good.
[00:08:15.200 --> 00:08:22.000] And I feel like it established credibility with customers because, you know, we're between these big platforms.
[00:08:22.000 --> 00:08:26.480] And so we kind of have to prove ourselves of like, how do I know you're not messing up on this?
[00:08:26.480 --> 00:08:29.360] Like, who, who, you know, who, who are you really?
[00:08:29.600 --> 00:08:30.400] You know, to me.
[00:08:30.400 --> 00:08:33.200] And we've closed quite a bit of business because of it.
[00:08:33.200 --> 00:08:37.760] Like we have gone through this big enterprise deal we just talked about, but also quite a few others.
[00:08:37.760 --> 00:08:41.040] I've just sent them a link to our trust center and they're like, okay, great.
[00:08:41.040 --> 00:08:42.800] Yep, we can see you've got a lot of stuff in place.
[00:08:42.800 --> 00:08:49.600] And so, I mean, it has investing in that has improved our product, improved our customer support, and increased our sales.
[00:08:49.600 --> 00:08:54.400] It just like forced us to grow up a little bit in ways where I want to take the company.
[00:08:54.400 --> 00:08:58.720] Like I wanted to be doing multiple millions in ARR.
[00:08:58.720 --> 00:09:02.520] And so it's like, okay, we're going to have to grow up in these areas.
[00:08:59.840 --> 00:09:06.920] And so it kind of forced that to happen in a structured way where I don't know.
[00:09:07.000 --> 00:09:07.800] I'm really glad about it.
[00:09:07.800 --> 00:09:17.560] People, 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 being having been a really important decision at the time.
[00:09:17.560 --> 00:09:20.360] Yeah, I would gripe about it because I hate that kind of stuff.
[00:09:20.600 --> 00:09:21.320] I don't.
[00:09:21.640 --> 00:09:24.680] You're building a business and you come from the sales side.
[00:09:24.680 --> 00:09:27.880] And you know that to make sales and to get big fast, you're going to have to close big deals.
[00:09:27.880 --> 00:09:30.920] And to close big deals, you're going to need SOC 2 in this space.
[00:09:31.080 --> 00:09:32.280] It's just inevitable.
[00:09:32.280 --> 00:09:35.720] And so you have just accepted it like a mature adult.
[00:09:35.720 --> 00:09:49.000] 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, you know, and I'm like, I want to do product and like design stuff and make sure this is all elegant.
[00:09:49.000 --> 00:09:51.400] And so I'd be like, ah, this SOC 2, why do I need this?
[00:09:51.400 --> 00:09:52.440] This is just a headache.
[00:09:52.440 --> 00:09:56.920] But you have just on this particular instance, you know, I'm sure there are other ones where you take the opposite tack.
[00:09:56.920 --> 00:09:58.760] But that's, and that's what we see within Tiny Seed.
[00:09:58.760 --> 00:10:04.040] There are certain founders who are more like me, who are like, God, kicking in, screaming, just scratching and clawing.
[00:10:04.040 --> 00:10:07.640] You have to pull, you know, for my cold dead hands than not, not going to SOC 2.
[00:10:07.640 --> 00:10:10.840] And then there are those who are just like, nah, it's not fun.
[00:10:10.840 --> 00:10:20.200] But I also know that I'll probably close, you know, literally hundreds of thousands of dollars in ACV next year if I have this, that I will not if I don't.
[00:10:20.200 --> 00:10:24.760] And so that becomes the question that a lot of founders have to ask themselves.
[00:10:24.760 --> 00:10:25.640] Yeah, for sure.
[00:10:25.640 --> 00:10:28.360] And it's given me a better lens to understand what's happening with our product.
[00:10:28.360 --> 00:10:32.680] Like I understand technically much better how our product is working because of it.
[00:10:34.600 --> 00:10:42.800] We've been talking about getting SOC 2 certified, a process that doesn't come cheap, but that's just one piece of Harris's growing expenses.
[00:10:42.800 --> 00:10:48.960] With a young family at home and a business that's scaling up, every financial decision carries extra weight.
[00:10:44.840 --> 00:10:52.080] I wanted to understand how he's navigating these waters.
[00:10:53.360 --> 00:10:56.720] Before, I'd ran an agency for five years.
[00:10:56.720 --> 00:11:01.520] It was profitable because it had to be, but it was never like a breakout success.
[00:11:01.840 --> 00:11:03.680] You know, I was never able to fully hand things off.
[00:11:03.680 --> 00:11:05.920] I was never really able to take a vacation.
[00:11:05.920 --> 00:11:09.280] It was always hard still, even though it was financially successful.
[00:11:09.280 --> 00:11:12.400] But also, I had an LLC that had a sub-ass selection.
[00:11:12.400 --> 00:11:14.080] So I was able to pay myself in a different way.
[00:11:14.080 --> 00:11:14.880] I had distributions.
[00:11:14.880 --> 00:11:16.880] I had a lot more flexibility.
[00:11:17.200 --> 00:11:20.720] Starting up on Sync, I wanted it to be a proper software company.
[00:11:20.720 --> 00:11:22.720] And this wasn't like a tiny seed requirement.
[00:11:22.720 --> 00:11:32.960] I 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.
[00:11:32.960 --> 00:11:35.840] And it's like, I just want this to be a fresh, solid start.
[00:11:35.840 --> 00:11:42.720] And so that change, I did not fully realize how much that shift of like, okay, now I'm only getting paid a salary because Up on Sync is a C corporation.
[00:11:42.720 --> 00:11:44.560] And so now we have payroll through ADP.
[00:11:44.560 --> 00:11:45.600] And that's it.
[00:11:45.600 --> 00:11:47.920] That money that I get paid, that is my money.
[00:11:47.920 --> 00:11:56.080] And I was just used to before being like, well, you know, I can take a distribution out of here and make sure I can cover this or that unexpected expense.
[00:11:56.080 --> 00:12:07.680] So that introduced like a pressure that I didn't, I think, think through fully at the time because I had five years of not having that kind of constraint that I sort of forgot what it was like.
[00:12:08.480 --> 00:12:10.000] I could always figure it out, basically.
[00:12:10.000 --> 00:12:10.640] I always found a way.
[00:12:11.120 --> 00:12:12.880] I landed a bigger client or this or that.
[00:12:12.880 --> 00:12:16.000] I started spending the tiny seed money more to get the growth going.
[00:12:16.000 --> 00:12:18.800] And I would say, like, both of those investments have been worthwhile.
[00:12:18.960 --> 00:12:20.720] Developer is very productive.
[00:12:20.720 --> 00:12:22.000] He's doing great.
[00:12:22.000 --> 00:12:22.960] We talk very little.
[00:12:22.960 --> 00:12:24.160] He just cranks on stuff.
[00:12:24.160 --> 00:12:24.800] We check in.
[00:12:24.800 --> 00:12:26.880] It's a really great relationship.
[00:12:26.680 --> 00:12:29.960] Um, and I can tell the difference, him going to 40 hours a week.
[00:12:29.960 --> 00:12:34.120] The productivity is like way, way outstripping the like percentage increase of time that he's working.
[00:12:29.760 --> 00:12:36.120] And then the CSM has been good because it's freed me up.
[00:12:36.200 --> 00:12:38.840] So, he's focusing on onboarding, getting new users.
[00:12:38.840 --> 00:12:41.560] That hire has worked out so far really, really well.
[00:12:41.560 --> 00:12:47.720] We went through Dynamite Jobs recruiting board, remote first recruiting, and they found a very good candidate.
[00:12:47.720 --> 00:12:52.280] I think he's really taking ownership of things, he's just like running with it more.
[00:12:52.600 --> 00:12:54.440] And that's freed me up to focus more on sales.
[00:12:54.440 --> 00:12:58.360] I think that's why these last couple months have been getting better in terms of sales.
[00:12:58.360 --> 00:13:09.320] I think that with these three people, me and CSM, an engineer, my goal is that we get to 30K MRR, and that would give us plenty of headroom at this point to be default alive.
[00:13:09.480 --> 00:13:13.560] I'm just like kind of trying to run as hard and as fast as I can to get to that.
[00:13:13.560 --> 00:13:17.880] I could lower that number though if I reduce my own drag on the business.
[00:13:17.880 --> 00:13:22.760] So, in like on the home front, I've been implementing a budgeting app called YNAB.
[00:13:22.920 --> 00:13:24.120] You need a budget.
[00:13:24.120 --> 00:13:31.880] And we now have four months of my wife and I have four months of budgeting data of our own spending, like down to the scent.
[00:13:31.880 --> 00:13:35.000] I did my own books for a while and I took like accounting classes in business school.
[00:13:35.000 --> 00:13:37.480] So, like, fortunately, that's actually been pretty easy to do.
[00:13:37.480 --> 00:13:39.480] It just has to sit down and do it.
[00:13:39.480 --> 00:13:47.560] So, I'm trying to figure out how do we tighten up spending on the personal side so that I can reduce my salary so that I can extend that runway a little bit more.
[00:13:47.560 --> 00:13:51.480] But, yeah, right now, I'm thinking about this like a lot right now.
[00:13:51.480 --> 00:13:54.440] And we're good now, but I like projecting out six months.
[00:13:54.440 --> 00:13:57.960] I'm kind of like, okay, well, would I do a revenue-based financing?
[00:13:57.960 --> 00:13:59.880] Would I pull some money out of retirement?
[00:13:59.880 --> 00:14:01.000] We're not running out of money yet.
[00:14:01.000 --> 00:14:10.440] We've got money in the bank, but because I have this salary, like 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.
[00:14:10.440 --> 00:14:13.720] It's totally like connected.
[00:14:13.880 --> 00:14:20.720] And, you know, we had a little bit of churn, and it's really hard to not be like, get too down about that because it feels like, oh, everything's in jeopardy.
[00:14:20.720 --> 00:14:22.480] You know, like, I was close and now I'm further.
[00:14:22.480 --> 00:14:26.320] And so there's that, like, yeah, it just feels like everything is all in one basket.
[00:14:26.320 --> 00:14:33.440] Man, it's tenuous because you grow another five or 10K MRR and you're like, well, finally, we're break even or we have a profit.
[00:14:33.440 --> 00:14:36.800] Oh, now I'm going, but I need to hire an engineer to keep up with XYZ.
[00:14:36.800 --> 00:14:45.920] So, you know, I'm not saying it never goes away, but it really is, even when you're doing a million, two million, three million a year, it's always this balancing act.
[00:14:45.920 --> 00:14:54.320] 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, you know, out of the bank account into your personal one.
[00:14:54.320 --> 00:14:56.240] Like, you know, there's still a stress.
[00:14:56.240 --> 00:15:05.120] But the thing that as a founder, you have to keep in mind is like, don't sacrifice your own personal finances or your families in order to get the company going.
[00:15:05.520 --> 00:15:06.960] But yes, there is risk.
[00:15:06.960 --> 00:15:08.320] So how do you, you know, how do you balance that?
[00:15:08.320 --> 00:15:09.120] That's the hard part.
[00:15:09.120 --> 00:15:15.760] That's why founders, as a rule, tend to have more anxiety and stress in their lives than employees of big companies.
[00:15:15.760 --> 00:15:20.640] But employees of big companies tend to have a lot more depression than founders do.
[00:15:20.640 --> 00:15:23.760] And this is, there's a, there's multiple studies that have verified that.
[00:15:23.760 --> 00:15:26.960] Sherry, my wife, has talked about this in a few talks.
[00:15:26.960 --> 00:15:28.080] It is more stressful.
[00:15:28.080 --> 00:15:34.560] The upside is significantly higher, but that does not come without some risk and some uncertainty.
[00:15:34.560 --> 00:15:36.560] And those two things are tough.
[00:15:36.560 --> 00:15:41.760] And they're tough on you and they're tough on your, you know, your partner or significant other.
[00:15:41.760 --> 00:15:48.880] 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.
[00:15:48.880 --> 00:15:54.160] And you know, if you sell this company or shut it down for years from now, you never want to do it again.
[00:15:54.160 --> 00:15:56.160] Or you can not worry at all about it.
[00:15:56.160 --> 00:16:00.760] And you can be like some people and they take out $50,000, $60,000, $70,000 of credit card debt to start their company.
[00:15:59.840 --> 00:16:04.680] And they're not nearly risk averse enough, you know.
[00:16:04.840 --> 00:16:18.280] And it's like there's some balance in between of like, 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?
[00:16:18.280 --> 00:16:19.320] Oh, totally.
[00:16:19.320 --> 00:16:23.640] I mean, I think fortunately, I've got like some levers I can pull.
[00:16:23.640 --> 00:16:30.200] Like, I mean, to go into my personal finances a little bit, like I've got like a universal life insurance policy that I had set up like when we first got married.
[00:16:30.200 --> 00:16:32.120] It's like, okay, well, let's cash that out.
[00:16:32.120 --> 00:16:35.480] Let's set up a term policy that'll actually pay out way more.
[00:16:35.480 --> 00:16:38.200] And then, okay, I've got that little bit to pay off some debt.
[00:16:38.200 --> 00:16:45.000] So now I'm reducing my month-to-month debt servicing that I've got in this area, better insurance than I had before.
[00:16:45.000 --> 00:16:51.720] So it's like little like levers like that that I'm pulling in a few different areas to kind of, and then I mean, there's hope on the horizon currently.
[00:16:51.720 --> 00:16:57.800] I know for a fact that 35% of our income goes to childcare, but we won't have young children forever.
[00:16:57.800 --> 00:16:59.720] School is on the horizon.
[00:16:59.720 --> 00:17:18.440] And so it's like, okay, it's possible that, you know, in three years, we're at MicroConf and I'm like, Rob, drinks are on me because, you know, the company's ripping and we just freed up multiple, multiple thousands of dollars a month in free cash flow that aren't going towards childcare.
[00:17:18.440 --> 00:17:23.800] So like, I do, I have that on the horizon that I think is like a reasonable thing to look forward to.
[00:17:23.800 --> 00:17:28.440] It's not like I'm going to, maybe I'll be on a boat, but it's not like I'm going to be a hundred millionaire, whatever.
[00:17:28.440 --> 00:17:31.560] Like that feels like a reasonable thing to, if I could just get there.
[00:17:31.560 --> 00:17:33.880] So that's kind of my mindset right now.
[00:17:33.880 --> 00:17:36.920] Like we've gotten really far in a short amount of time.
[00:17:36.920 --> 00:17:38.520] So I think that we can, I think I can get there.
[00:17:38.520 --> 00:17:39.080] I just have to.
[00:17:39.720 --> 00:17:40.920] It should get easier.
[00:17:40.920 --> 00:17:46.960] I mean, you are still very early in this business and the early days, everything's fragile.
[00:17:44.040 --> 00:17:53.920] Like even your knowledge and confidence that the business is going to work is pretty fragile.
[00:17:53.920 --> 00:17:56.320] Your product market fit is really fragile.
[00:17:56.320 --> 00:17:58.080] Your sales process is fragile.
[00:17:58.080 --> 00:18:00.560] You're thinking of like, who is this revenue going to stick around?
[00:18:00.560 --> 00:18:01.680] Is it going to continue to grow?
[00:18:01.680 --> 00:18:03.120] All of that's fragile still.
[00:18:03.120 --> 00:18:06.640] And that does solidify as the company matures.
[00:18:10.480 --> 00:18:15.280] Harris has talked before about expanding to other CRMs outside of HubSpot.
[00:18:15.280 --> 00:18:18.320] One of his newest missions was to integrate Salesforce.
[00:18:18.320 --> 00:18:20.720] And I wanted to see how that was going.
[00:18:23.280 --> 00:18:34.640] Well, so, okay, I didn't cheat, but I did maybe bend the rules of what like maybe you are thinking a Salesforce integration is because there's two ways to integrate with Salesforce.
[00:18:34.640 --> 00:18:38.720] And we did a connected app, which is essentially like a private unlisted app.
[00:18:38.720 --> 00:18:41.360] And so that allowed us, and this is what we did with HubSpot too.
[00:18:41.360 --> 00:18:43.680] It allows us to sell to Salesforce customers.
[00:18:43.680 --> 00:18:51.840] They just basically create their own like authorization for our web server to like hit their Salesforce account.
[00:18:51.840 --> 00:18:53.040] So that was how we moved so fast.
[00:18:53.040 --> 00:18:59.120] And then the other thing we did is we started with a tiny, tiny, tiny footprint of what it does.
[00:18:59.120 --> 00:19:04.800] And so we just solved like a very basic problem of like, we log emails as activities.
[00:19:04.800 --> 00:19:05.600] Do you want that?
[00:19:05.600 --> 00:19:07.920] And enough people were saying, yeah, that they've like started paying.
[00:19:07.920 --> 00:19:09.680] So we have multiple paying customers.
[00:19:09.680 --> 00:19:15.760] We've got like a mid-market company that we're in procurement process with now who wants that.
[00:19:15.760 --> 00:19:20.160] And then another one who has said, like, hey, I'm going to sign up for this probably in the next week.
[00:19:20.160 --> 00:19:32.360] So I think that we'll go from zero dollars in Salesforce revenue to probably like $2K MRR probably by the time we hit January, all of that closing basically over the course of like a month.
[00:19:32.440 --> 00:19:42.120] And then if we do that, you know, if all of our other numbers stay the same, I'm just doing quick calculator math here, you know, that'll end up being like 15% of our revenue.
[00:19:42.120 --> 00:19:43.640] So that's pretty cool.
[00:19:43.640 --> 00:19:48.120] But we're using Salesforce like brand as distribution, but not the app exchange.
[00:19:48.120 --> 00:19:49.320] The same thing we did with HubSpot.
[00:19:49.320 --> 00:19:53.800] Like I talk about on LinkedIn and I talk about other agencies and I say, if you use HubSpot, we can support you.
[00:19:53.800 --> 00:19:57.480] But the HubSpot thing, I was really, really, really, really proud of getting that.
[00:19:57.480 --> 00:19:59.000] And that was cool.
[00:19:59.000 --> 00:20:03.800] But we were selling the HubSpot app for over a year before we were in the marketplace.
[00:20:03.800 --> 00:20:06.680] And I think we're going to do the same thing with Salesforce agency.
[00:20:06.920 --> 00:20:08.680] That's moving fast and getting a V1 out there.
[00:20:08.680 --> 00:20:12.200] And then you built thousands and thousands of MRR.
[00:20:12.200 --> 00:20:19.240] I mean, you could have supported yourself almost full time on the business and you didn't have to wait for any of that, right?
[00:20:19.240 --> 00:20:20.840] And this is what the best entrepreneurs do.
[00:20:21.400 --> 00:20:24.360] They get it done real fast and then they turn around and say, all right, well, what's a V2?
[00:20:24.360 --> 00:20:27.560] Well, V2 is getting in the app marketplace because then we get promotion and all that.
[00:20:27.560 --> 00:20:32.360] I mean, you got into the app market, even the HubSpot app marketplace, it felt fast to me.
[00:20:32.360 --> 00:20:33.560] I don't know what the timeline was.
[00:20:33.880 --> 00:20:35.560] Oh, yeah, it only took like two weeks.
[00:20:35.560 --> 00:20:36.600] Because we were so ready.
[00:20:36.600 --> 00:20:41.560] They were like blew past their paying customers on it.
[00:20:41.560 --> 00:20:45.960] Normally you go in the app marketplace with no customers and then they're like, nope, testing for months, right?
[00:20:45.960 --> 00:20:48.680] And you need to have this many beta users and you already used it through it.
[00:20:48.680 --> 00:20:50.120] That's another exactly.
[00:20:50.120 --> 00:20:55.720] And you said, and I quote, we're the first smart lead integration in the HubSpot app marketplace.
[00:20:55.720 --> 00:20:58.360] And you sounded really proud of that, you know?
[00:20:58.360 --> 00:20:58.680] Yeah.
[00:20:58.680 --> 00:21:00.680] Yeah, before even SmartLead themselves.
[00:21:00.680 --> 00:21:00.920] Yeah.
[00:21:01.160 --> 00:21:04.600] Before their own integration, you beat SmartLead.
[00:21:04.600 --> 00:21:07.720] So that's got to be a pretty big point of pride for you.
[00:21:07.720 --> 00:21:08.360] Oh, for sure.
[00:21:08.360 --> 00:21:08.760] Yeah, yeah.
[00:21:08.760 --> 00:21:10.280] I mean, I think we're shipping really fast.
[00:21:10.280 --> 00:21:16.160] And I was in a chat with the founder of SmartLead, and he was like, you ship, which they have a great engineering team.
[00:21:14.600 --> 00:21:21.120] So I know he really means that as a compliment, you know, I mean, in their world, they really value engineering.
[00:21:21.200 --> 00:21:22.720] So yeah, we move fast.
[00:21:22.720 --> 00:21:26.880] And we've got two other sales engagement platforms that I think are going to potentially open up market for us.
[00:21:26.880 --> 00:21:31.040] Like it's the same core product, but competitors to SmartLead.
[00:21:31.280 --> 00:21:34.400] And I think, again, we will be the first integrations listed for those tools.
[00:21:34.400 --> 00:21:43.840] And I think that when we move, like our positioning is going to change to be like, hey, if you're using one of any of these app on tools, we'll be the one that gets it in your CRM the right way.
[00:21:43.840 --> 00:21:45.280] I think we'll be able to charge more.
[00:21:45.280 --> 00:21:46.880] That's kind of like what's on the horizon.
[00:21:46.880 --> 00:21:53.040] But I think that like this play that we just ran SmartLead, I think we're going to run twice again for two other tools.
[00:21:53.040 --> 00:21:56.160] And now I've got people being like, do you support Lemlist?
[00:21:56.160 --> 00:21:56.800] Do you support this?
[00:21:56.800 --> 00:21:57.440] Do you support that?
[00:21:57.440 --> 00:22:03.040] And so we're starting to get a waitlist forming for other tools.
[00:22:03.040 --> 00:22:12.960] And that, yeah, that just like kind of feels like to me, again, like we're in these like more advanced stages of becoming a real company.
[00:22:13.120 --> 00:22:22.400] Call that market pull, where it's like, and you're getting data because you're like, ooh, we have three requests for limb list and we have two for this other tool.
[00:22:22.400 --> 00:22:25.760] I don't know the space well enough to know we know what other tools are, but two for this other tool.
[00:22:25.760 --> 00:22:31.440] 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, you know?
[00:22:31.440 --> 00:22:36.400] And so now you have all the CRMs on one side and you have all the wet, cold email tools, I guess, on the other side, right?
[00:22:36.400 --> 00:22:37.280] That's what you're thinking.
[00:22:37.680 --> 00:22:40.000] But could be LinkedIn, could also be phones.
[00:22:40.000 --> 00:22:40.480] Yep.
[00:22:40.480 --> 00:22:41.680] So there's a lot.
[00:22:42.000 --> 00:22:43.600] There's a lot to be done here.
[00:22:43.600 --> 00:22:53.600] 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?
[00:22:53.600 --> 00:22:54.800] Because you were early, right?
[00:22:54.800 --> 00:22:56.480] We don't know if the business is going to work.
[00:22:56.480 --> 00:22:58.160] Do we think that Harris can do this?
[00:22:58.160 --> 00:23:00.760] And the answer was, yeah, I think he can do it.
[00:23:00.760 --> 00:23:02.360] And then why did we invest in the business?
[00:22:59.840 --> 00:23:04.680] Because it had traction, it had people that wanted to pay you.
[00:23:05.000 --> 00:23:10.520] And we see, I see the potential of this to be a seven or eight-figure ARR company.
[00:23:10.520 --> 00:23:13.160] Not with the initial product you had.
[00:23:13.160 --> 00:23:14.280] You know, it was what?
[00:23:14.280 --> 00:23:16.200] Smart leads to HubSpot, and it was very simple.
[00:23:16.200 --> 00:23:18.040] And it was first zaps, and then you had someone write code.
[00:23:18.040 --> 00:23:20.120] You know, I mean, that's not an eight-figure business.
[00:23:20.120 --> 00:23:28.760] But all that the vision that you're starting to paint here and the request, the market pull you're starting to get, that absolutely could do, could do 10 million or more in ARR.
[00:23:28.760 --> 00:23:30.040] Yeah, I believe so.
[00:23:30.040 --> 00:23:33.000] And I will say, I think this to me, this is why, like, well, Tiny Seed is different.
[00:23:33.000 --> 00:23:36.120] It is still fundamentally a venture endeavor.
[00:23:36.120 --> 00:23:41.240] Like, the risk of investing at the time, I mean, it reminds me of like when my wife decided to marry me.
[00:23:41.240 --> 00:23:42.440] It was like, rest of your life?
[00:23:42.520 --> 00:23:43.240] Are you like, are you sure?
[00:23:43.640 --> 00:23:44.200] Potential.
[00:23:44.200 --> 00:23:45.560] You saw potential.
[00:23:45.560 --> 00:23:48.520] Yeah, I'm not sure that I would marry me at this point.
[00:23:48.760 --> 00:23:51.720] We got married, not super young, but you know, it was a while ago.
[00:23:51.880 --> 00:23:53.080] We've been married for a long time.
[00:23:53.080 --> 00:23:55.560] But yeah, so it's fundamentally, there was a risk there, you know?
[00:23:55.560 --> 00:24:00.040] And so, yeah, I feel like y'all took a chance on me, and it's been, it's been cool.
[00:24:00.040 --> 00:24:01.400] You're making good progress, man.
[00:24:01.640 --> 00:24:07.400] Looking ahead over the next one to three months, because you know, it will record in the next one to three months.
[00:24:07.400 --> 00:24:09.800] What are you most excited about?
[00:24:10.440 --> 00:24:13.640] I believe really firmly that we are ahead of the market.
[00:24:13.640 --> 00:24:25.800] I think that the users that we're signing up and the prospects we're talking to today represent like the very beginning of a big chunk of a bell curve of the market that's going to be changing its process.
[00:24:25.800 --> 00:24:35.640] Like, 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.
[00:24:35.640 --> 00:24:37.640] And they have said, like, okay, great.
[00:24:37.640 --> 00:24:39.880] What email tool should we use?
[00:24:39.880 --> 00:24:41.160] Like, I don't even care.
[00:24:41.160 --> 00:24:43.960] I just need the data that you're giving me.
[00:24:44.280 --> 00:24:57.840] And so, to have, to be taking customers from outreach, which is like a unicorn, arguably created the sales engagement platform category, to be taking users from them as a like connector app, which I think we're doing more than that or solving different problems than that.
[00:24:57.840 --> 00:24:59.120] To me, that's like a really big deal.
[00:24:59.120 --> 00:25:03.760] And we have got two customers, like one we just closed and another one that's about to close that were like this.
[00:25:03.760 --> 00:25:05.840] And they're like, whatever, however, we need to send the emails.
[00:25:05.840 --> 00:25:08.000] I just want the way that you're putting it in that system.
[00:25:08.000 --> 00:25:10.560] So, I think we just keep moving down that path.
[00:25:10.560 --> 00:25:13.840] I think there's going to be, I think there's a lot more people to come, basically.
[00:25:13.840 --> 00:25:15.840] And I think the people we're helping right now are early adopters.
[00:25:15.840 --> 00:25:18.560] And so, if that's true, then I think we're going to have really good mojo.
[00:25:18.560 --> 00:25:20.480] I think we've got some really good agency partners.
[00:25:20.480 --> 00:25:28.960] And I think that when we add, like, build out Salesforce and that 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'll start unlocking more pieces.
[00:25:28.960 --> 00:25:31.680] So, I'm really confident in that potential.
[00:25:31.680 --> 00:25:37.520] 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.
[00:25:37.520 --> 00:25:48.880] And so, I need to figure out like how to become a more mature product marketer to capture that because I talk to customers who get it, but I can't trust, I can't wait for everyone to get it.
[00:25:48.880 --> 00:25:53.360] I need to like, you know, so that, but that's where, I think that's where the opportunity is.
[00:25:53.360 --> 00:25:58.480] And I think that when I look at like where we're taking business from, it's not just people who are using Zapier right now.
[00:25:58.480 --> 00:26:03.920] It's, 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.
[00:26:03.920 --> 00:26:05.120] And you are.
[00:26:05.120 --> 00:26:08.160] That is like, okay, cool.
[00:26:08.480 --> 00:26:09.840] It's super motivating.
[00:26:10.160 --> 00:26:10.880] Outreach is fine.
[00:26:10.880 --> 00:26:11.840] Maybe we'll integrate with outreach.
[00:26:12.160 --> 00:26:16.640] I have no beef with them, like, whatever, you know, it's just, it's just B2B SaaS software, yeah, who cares?
[00:26:16.640 --> 00:26:19.920] But the competitive side of me is like, okay, yeah, like we're doing something.
[00:26:19.920 --> 00:26:20.720] We're making a mark.
[00:26:20.720 --> 00:26:23.760] We're getting people to switch, which is, which is cool.
[00:26:27.280 --> 00:26:32.120] What started as a simple connector app has evolved into something much more ambitious.
[00:26:32.440 --> 00:26:39.400] Harris is finding his product isn't just competing with simple automation tools, it's pulling customers away from industry giants.
[00:26:39.400 --> 00:26:46.760] And in today's market, where companies are scrutinizing every dollar spent on their tech stack, Outbound Sync seems to be resonating.
[00:26:46.760 --> 00:26:51.240] The question is, how far can this unexpected momentum take him?
[00:26:51.240 --> 00:26:54.200] Find out next time on Tiny Seed Tales.
[00:26:58.360 --> 00:27:00.360] I hope you enjoyed this episode.
[00:27:00.360 --> 00:27:12.040] 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've put together something special for you at tinyseed.com/slash bonus.
[00:27:12.040 --> 00:27:13.000] You should check it out.
[00:27:13.000 --> 00:27:15.400] I've never released anything like this before.
[00:27:15.400 --> 00:27:16.280] I hope you enjoy it.
[00:27:16.280 --> 00:27:19.080] It's at tinyseed.com/slash bonus.