What's your backstory?

I grew up in Nashville, Tennessee. My dad was a songwriter. I like to say that he is my biggest inspiration as a creator. There's a lot of overlap in the way he lived and worked and the way that I live and work, being very family-oriented and being around for the kids and present, but also just kind of working all the time, in a sense, coming up with song ideas in his head or while he's driving or whatever he's doing. It's sort of similar to me, that I’m always thinking about ideas and how to do my next task.

I ended up going to college in Oregon. It was a very last-minute decision, but I ended up there. I was an environmental studies major, which I never did anything with, but I just loved the outdoors and camping and that sort of thing.

When I was a senior in college in 1999, I first had access to a computer in my college apartment. My roommate owned it and was working on some website design. I found myself peering over his shoulder and thought it was cool. That's how my interest in computers really started. I began with small design projects, and building websites. Soon, my interest shifted towards making websites more interactive, and that led me to delve into Macromedia Flash, which Adobe eventually acquired.

That was my introduction to coding. I taught myself ActionScript, which was the Flash coding language. And then after college, I ended up getting a job at Adobe. I started in October 2000, the end of the dot-com boom, so in a sense, I got lucky because they were hiring anybody and everybody. That’s how it started, and everything went from there.

What does Castanet do and how did you come up with the idea?

Castanet was a LinkedIn outreach automation tool. You'd go on LinkedIn and put in lists of people that you want to contact. This tool was often used by sales teams, agencies, or even founders -- really, anyone looking for customers, clients, or leads. They would put in a list of people they want to reach out to and then could create a sequence that would automatically connect with these people or request to connect with them on LinkedIn, with or without a message. Users could use variables and templated messaging, and the tool could follow up or just send a message, or follow up if they do reply, and automatically view profiles.

It's a way to create a sequence of any of these steps of reaching out and connecting with people, sending messages, and viewing profiles. You could do it in any order and have the sequence stop if someone replies, so you can manually take over.

The idea came from talking to a bunch of sales teams, but it ended up being used by lead generation agencies a lot, as well as individual freelancers and consultants reaching out to people. I got the idea by starting to reach out to anyone in my network who had a high-level position at any company or owned a company, business, or agency. This was after a long period of trying to scratch my own itch and build things that fit with my personal hobbies. I decided to change things up. I reached out to five or 10 people that I knew or knew of, and it all started out with people who knew me in one way or another - either friends or just people I knew. I would reach out to them and ask if I could take them for coffee. These were all in-person and having coffee locally. I would just reach out and ask if I could pick their brain about something, and they pretty much all said yes. People like to talk about themselves and the issues they're having, so that wasn't very difficult. Also, starting with people who knew who I was made it a lot easier.

I just started meeting up with people and asking questions like what’s the worst part of their day, and what's the most time-consuming part of their day. I quickly went from just anyone that I was reaching out to down to sales teams. I could tell that sales teams had a couple of things going for them. They had money that they weren't afraid to spend. 

Lead generation quickly became a focus because people need leads and there's a lot of money in leads. I went from anybody, to sales teams, to lead generation. Then there were a few ideas that kept popping up, common themes I got from talking to people. I was experimenting with these over time, and I would often go and have some meetings, go home and think about what was said, figure out the common threads, and then reach out to more people.

I would often ask the people I did meet for introductions to other people that might be interested in talking to me. The easiest way to get people to talk to you is people that already know you, and then the next step is to get other people who don't know you to have some sort of trust in you to be willing to talk to you. Getting an introduction expedited that process. It was really easy to just get a lot of people to talk to me that way, and I just kept narrowing it down. At some point, I was sitting across from somebody, and they said, you know, I think you're getting close to something, and if you did it this way, right now I would give you my credit card and have you swipe it for 800 bucks a month. That was the final comment I got when I went home and started writing the first line of code. It turned out that that was it, that worked. Then four weeks from that day, I had a working version, launched it, and reached out to a bunch of the people I had already talked to who knew what I was working on. People started paying for it. So I believe on that first day about four weeks after writing the first line of code I was swiping cards.

How did you get your first 10 customers?

The first 10 customers came from people I had been talking to in the process of coming up with the idea for the product itself. In that process of trying to hone in on the idea, I talked to dozens of people. By the time I launched, I had a number of those people who I knew might be interested in what I had discussed with them and built. I looked at this list not that long ago, and the first 10 or so people who paid were either people I had reached out to initially, people I had already had in my network, or people that I was introduced to along the way.

If I rewind back to before I even started reaching out to anybody, they would have been very much cold leads, a number of these people. By the end of the process, they had become warm leads because I had gained a bit of trust from them through getting an introduction from a mutual friend, and then also having met them in person after getting that introduction. By this time, we were considered friends.

What steps did you take to understand and confirm that your product was a good match for the needs and wants of your target customers?

The idea came from talking to people in the first place with no expectation of what I would get out of it. I had no bias as to what the product would end up being. By talking directly to prospective customers, I gained confidence that in the end I would build something people wanted. Of course, you never really do know until you swipe your credit card, but you can still get a pretty good amount of confidence.

It was a smooth process overall. There was a point where in talking to people I had gotten an idea from talking to somebody and they seemed really excited about it. I went home and built a quick prototype in a day or so. I went back and I showed it to them and it turned out their response was like, oh yeah, that's cool. That's what I was talking about. That's exactly what I meant. I was basically asking if they would pay for it and they said, oh no, I don't think I need to pay for it, but it's cool.

That was sort of a big lesson that people don't pay for “cool.” I don't need cool ideas. I've got a million cool ideas, but it's the valuable ideas that I’m going to pursue.

How did you grow Castanet from $0 to $58K MRR?

The first sale was around August 2018. I was handling the growth on my own, and then around February, a customer reached out to ask if they could white-label the application. Initially I said no. I told them I didn't have the time or the capacity for it. 

But as time went on, I gave it more thought. By that point, I was hitting somewhere between 7 or 8K MRR, things were going well, and I had a pretty solid sales process in place. I understood how to bring people in, knew the right messaging, and had identified my target audience. A lot of my success was coming from the demos I was doing, which were really driving in better clients and customers.

So, at that point, I reconsidered the whole white-label idea. This customer wanted to resell the application, essentially branding it as their own and taking a cut from the sales. I was already maxed out with handling the sales and product development. So, I called them back and agreed to the white label. That’s how I got my first reseller.

That decision marked a significant change. By the end, I had about four resellers, each with their own brand, selling the application. It was the same application on the same server, but each had a different URL, logo, and color scheme. This approach allowed me to scale without needing to hire additional staff. The resellers sold to their own customers and handled the first level of support, while I managed the product and continued working with my own customers and agency clients. This model became a pivotal point in scaling the business. The resellers brought in people through their websites and took a percentage of each sale.

And to expand a little bit on how the reseller thing worked, by this time I had good product market fit. I knew who to target, who would pay, and I knew the messaging and the words they used. And I also had basically a repeatable sales process with using the tool itself to do the outreach on LinkedIn to generate traffic and leads for the tool. So it all worked really well, and it's the same way that the resellers for the most part generated their leads. And over time there was word of mouth and things like that. But a big majority of all the leads across the platform came from using the tool itself to generate the leads.

What distribution channels did you try that didn’t work?

I built plenty of apps and tried marketing strategies and channels that did not work. Luckily with this one, really from right out of the gate, using the tool itself to generate the leads worked really well. And I actually don't recall ever trying anything else. So I just stuck with it because that's what worked. So in this case, I didn't try cold email or SEO or even social aside from LinkedIn.

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What specific tools, software, or resources have been most helpful in growing your business?

Mainly LinkedIn for generating leads, and First Promoter was used a bit for affiliates, so that affiliates could track affiliate sales. And then GitHub and Slack, and that's pretty much it.

Why and how did you end up selling the business?

I hadn't really planned on selling the business, and in fact, I hadn't thought much about it at all. Then I got to a point where things were great with it. I wasn't really in a feature race, and I was quite cautious about adding features to the application. I knew that many requested features never really got used, so I'd have to be really convinced, or hear it from a lot of people, that a new feature was worth adding. This meant I had some quiet periods when there wasn’t much I needed to do.

But the business also grew so big that when things went wrong, the pressure was immense. With a lot of customers depending on the app, and its nature being very sensitive – sending messages and requests – any issues, especially being dependent on a third-party platform like LinkedIn, could be really bad. Issues like sending multiple messages to someone, the wrong messages, or anything like that, just became very high stress. I was the only one who knew the code base well enough to fix these things. It meant that any time of day or night, I had to drop everything and fix it.

I realized I needed to either hire people or sell the business. So, I made a call to a broker I had heard about at MicroConf. That was my first call. I loosely told them what I was making from it and what the business looked like. They gave me a ballpark figure over the phone, and I decided to follow through with it. It was a process, took a while to figure out that I could actually sell it and that it would go through, and all these things. But ultimately I decided to sell it and try something new.

What motivated you do do it all over again and start Aware?

I had actually started Aware a while before I ever even thought about selling Castanet. I started it with a friend and I just started it because they called me one day with an idea that they were really excited about, and I thought it'd be fun to try something else on the side. So it was going sort of in the background for a while, even while I was running Castanet and it was just fun to do different things. I like to try new things and especially have a clean code base and try something new.

Who are some recommended experts or entrepreneurs to follow for learning how to grow a business?

One of my all-time favorite humans is Derek Sivers: sivers.org/

I just love his approach to business and life. His website is a joy to read, as are all his books.

I'm really geeking out on all the Alex Hormozi content right now.

Any quotes you live by?

Live now.

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