Rob Walling

Before we get further, I want to dig into the story of Trotto and how you've been growing it. But can you give us an idea of where the business stands today?

That is, that's the next thing I want to talk about is you have, you know, I talk about on this podcast, five stages of awareness from Eugene Schwartz, and it's unaware, problem aware, solution aware, product aware, and most aware, right? In that order. For most people, they're just unaware. Like I was unaware of this before you interviewed at TinySeed.

But then there is a different subset that is problem aware. And the problem that they have is I used GoLynx at insert name of startups. I'm at the new place of employment and my problem is I really want those, right? But they probably aren't aware that there is a solution to this.

And I imagine they think I need to get engineering to build it because we had a custom one at the other thing and the IT department or whatever maintained it, right? So how do you as a founder who's trying to grow this business understand deal with that of, hey, you're, because in a perfect world, you're at stage one and two, you want to be at four and five, right?

You want to be at like a product, everyone's product aware, because I'm HubSpot or Salesforce, you know, or Shopify, or everybody's most aware, whatever, it never happens, but you're all the way at the other end. So it feels like a headwind. How do you think about that as a founder?

Right, a real customer education challenge, right? Because you're not inventing a new category because the category exists, but it's not a big category yet. It's not DocuSign like electronic signature or scheduling links or marketing automation or something where it's this massive thing with dozens of competitors, if not hundreds.

It's this, and this is a conversation you and I've had, when you interviewed for TinySeed, was like, how big can this get? I mean, I guess over the course of 20 years, as people move to a new job and move to a new job, it'll eventually propagate. But today, how do you think about that as a mostly bootstrap startup?

I'm presuming, since you're in TinySeed, that you want to get to seven or eight figures in ARR. Yeah, and how do you think about that?

There are actually quite a few products in TinySeed that are like hard to get the deal signed, but the retention is through the roof. It's like there's zero, there's net negative churn, frankly. And it feels like Trotto is that kind of product. Would you agree that like-

And so I'd imagine that your marketing or slash go-to-market motion has to all be outbound, right? because I can't imagine there's much search volume or even much conversation in Facebook groups or Quora or Reddit. I have 20 B2B marketing approaches in SaaS Playbook, and I'm guessing 19 of them don't work.

I'm sure in-person event, there are some things that could work, but it seems like you would have to be going out there finding people.

Yeah, that's the stage of a lot of... Most listeners to this show are in that stage of trying to figure out what's the repeatable thing that I can scale up. I remember it was interesting in some of my earlier software slash SaaS companies, I found one or two channels that I could really crank up and really get a lot of volume out of.

When I launched Drip, I remember being like, yeah, I've got to find that one or two thing, one or two, and it never happened. It was just a bunch of things. I don't think there was a single kind of traffic source, so to speak, that was more than 15% of our monthly trials. Oh, wow. I was dealing with Facebook ads. I was paying somebody to run those. We were doing SEO. I was doing podcast tours.

We had an affiliate program. There was all kinds of stuff. That's great for diversification so that no single source can crush you. It also kind of sucks because I had to manage all of that. At the time, we were like a four-person team, five-person team. By the time we sold, we were 10 people. But, oh, and we were doing cold outbound as well.

I mean, we were doing all of it, and it was all kind of working, it was all working well enough, and as a big, like, it got the snowball going, and the growth was really good. I mean, that's one of the reasons we got acquired, was we were picking up market share so fast. But I found it frustrating to be on this small team and be like, I don't want to manage all this crap. Like, I needed...

I needed a marketing team of like six or eight people probably. And it was, it was me halftime and a full-time junior marketer, you know, and then like our customer success person halftime. And it just, it was always frustrating. It is, it's not a myth to be like, Ooh, you're going to find one or two things that work, but it's really hard. Like it takes a lot.

It doesn't just take a lot of trial and error. It just doesn't work in all spaces or with all categories where you're just going to find that single silver bullet, so to speak. Yeah.

Yeah, it's definitely helpful to learn from those who came before you. That's whether if you're in tiny seed, you know how to do that. If you're in the microconf orbit, that's microconf connect or even listening to this podcast and hearing the experience of folks and reading the books and all that.

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