The UI Audit: Interview with Rob Walling of Drip

Published April 07, 2016 by Jane Portman

This is the second founder interview from Jane’s new book, The UI Audit. Today Rob Walling, the founder of Drip, shares their story of finding the desired product-market fit. By positioning Drip as an email marketing automation tool they were able to reduce churn, rapidly grow the customer base, and gain a clear vision of new features. If you enjoyed the interview, you’re welcome to get your copy of the book here while the launch discount is still active.

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Show Notes

Full Transcript

Jane: Hello ladies and gentlemen, and today we have another awesome interview for the UI Audio Book, and today Rob Walling is joining us. He’s the founder of Drip software and we just talked to Derrick Reimer, and now we’re going to talk to Rob about marketing, and how marketing affects UI/UX decisions. So, hi Rob – thank you for coming today!

Rob: It’s my pleasure, thanks for having me, Jane.

Jane: Amazing. So we just learned what Drip is actually about, but we would love to hear your version of the story, how Drip got started.

Rob: Sure. You know, I was running an app called HitTail – software service app; this was in 2012. And I decided I really wanted to double down on the email list, so I wanted to build it up and couldn’t find an easy way to add email capture, an email form to every page of the website. And I didn’t want to go in and have to modify HTML, I didn’t want to put it in the header, didn’t want to put it in the footer, and so I worked with Derrick who was a contractor for me at the time and we came up with an idea of having this little Java Script toaster widget pop up. And now, they’re all over the place. You have SumoMe and OptinMonster, there’s a lot of them – and Drip, of course. But at the time, there was no software that did this. There were a couple of open source libraries. And I wound up taking Derrick several days to style this thing and get it up on the site, and get it working and getting all the copy written and all that stuff, and it was kind of a fiasco. A lot of time, and a lot of effort, especially to get it wired up in MailChimp and everything. So I realized there’s probably an opportunity there to build something to make that process easier.

Jane: So it was totally a fertile ground there, and it also was scratching your own itch at that time.

Rob: Yeah, I did go out and validate it beyond that, because I don’t like building things based on one person’s opinion, even if it’s mine. So I went and found 10 people who committed to paying me a monthly fee for it before we started building.

Jane: Did they actually pay you those dollars?

Rob: No, I just got commitments in advance.

Jane: Right, and from there to the point where it’s now, you’ve gone a long way to finding that perfect product market fit, and you shared that quite a lot at your recent MicroConf talk, and I’d love our listeners to know that as well. How did it actually happen? It’s not like a one-day decision, how did you nail down that position for marketing automation?

Rob: Yeah, it was a pretty long road. Derrick spent about – it was about 6 months building. He was first doing it half-time because he was working on HitTail, and then I realized that Drip was just such a bigger opportunity and moved him over to full-time working on it. And Derrick later became my co-founder by the way, and so he started as a contractor and then we changed that relationship up later on. But in essence, Drip launched as really as an email marketing platform that did some basic stuff, kind of akin to MailChimp. And what we found is that if we wanted to charge more money, than MailChimp, the typical email provider, then we had to have more advanced features.

And it makes sense in retrospect, but we thought we had a differentiated product, we had really good UX and UI interactions, and we had an easy to use system that did the job really well, but a lot of people said this is great software, but it’s just not worth what you’re charging. And we were charging $49 a month is what I wanted the minimum plan to be, because I’ve had a lot of apps that are $10, $20, $30 a month and those apps are hard to grow to the level that I wanted to take this one. And so, after getting that feedback, a lot of people said it’s just a little too expensive. I debated – do we drop the price or do we basically build more advanced features. Like what features do I need to build to make this worth $49?

And that’s where we had a ton of user feedback and sifting through that is hard. It’s a challenge to know what to build, but in essence, I noticed that marketing automation was brought up and these automation rules, and being able to move people in and out of sequences based on what they do, and tagging and all that stuff was a prominent thing and it seemed like it was kind of a wave that was just starting to crest, just starting to build up. And so, that was the point where we decided to build an automation engine, and as we started deploying that over the course of several months, it was obvious that our churn was dropping and our trial to paid conversion rate was going up, and that was what was getting us towards product-market fit.

Jane: So these were the obvious vital signs that you made the right decision.

Rob: Yes, because it was not obvious that we had made the right decision. I mean, when you first break ground on this code, I asked folks if this is what they wanted. But you have 200 people, 300 people giving you their opinion and it’s hard to figure out what to build. So it was a good couple of months of kind of agonizing over which direction do we take this, what are we actually building here?

Cause we didn’t just want to build features – that doesn’t help. You have to have some type of vision for where you’re headed. And when we made the decision like we are going to become like a lower-cost, high value marketing automation platform, then you instantly know what to build and what not to build. You’re not going to build shopping cart software on to it, which some people are requesting. You’re not going to build an affiliate management program; you’re not going to build landing pages probably. You’re not going to build that CRM upfront. There’s a bunch of things that you don’t need, and then we can really focus on exactly what we needed to build.

Jane: Yeah, that’s a great approach. And we just talked to Derrick about that integrations can actually replace those requests pretty well, and keep you focused on that key functionality that you set out to build. So, how did those customer interview look like? Did you explore their personas, did you give questionnaires for them, or did you just have free chat?

Rob: I did a lot of free chat, and to be honest it was all via email. I don’t know that I had any – actually, I had a couple in person at MicroConf – at MicroConf Europe a couple of years ago where some people specifically said: have you thought about building something that’s way easier to use than Infusionsoft, maybe a little less expensive but that does 70–80% of what it does? And I got into several conversations in person and I was trying to wrap my head around what that even mean. What parts of Infusionsoft? Why is it hard to use and what don’t you like about it and how expensive? And just getting into that world; I wasn’t in that world yet so there was a lot of education. But that was just me growing someone. Literally taking notes – I’m on break at MicroConf, I’m running the conference, thinking about who’s going to speak next, but I started taking kind of customer development notes at this point, and we’re already live and doing $8–9k in revenue, somewhere between 7k and 9k, I don’t know what it was. And yet, we need to do customer development for this next phase to figure out what folks want. And I did a lot of interviews via email where I reached out to folks that I trust. I mean, I had the luxury of that, of having people who were using Drip who I knew well enough to know that they would give me decent advice, and they were smart and it wasn’t just these unknown people who aren’t going to take the time to give me feedback.

It was not an overwhelming majority, it was not like ‘Boy, 90% of people said you should go into marketing automation’ – it was not like that at all. There was a lot of signals, there was a lot of noise in sifting through it. It was kind of like okay, so the first step is to build some automation stuff. The second part was figuring out what do we call ourselves now. Are we email marketing? Are we something more like Intercom or or Zero or – I’m sorry, not Zero, Vero. There’s all these things you can be in the email space and I didn’t know what we were to be called at that point, and that became a whole other search, to find a label of what position we were in.

Jane: Yes, did you do research to find actual words?

Rob: Absolutely. Yeah, I was all over the email space looking over all the folks I just named, plus 20 or 30 other email marketing companies, just to figure out: were we still email marketing? Had we become customer-centric email marketing, had we become marketing automation? I didn’t really know what marketing automation was, but as I dove into it, I realized email is at the center of marketing automation and so, although we hadn’t…

Marketing automation typically includes this email marketing piece, the CRM, there’s lead scoring, there’s – trying to think, there’s a couple of other pieces to it, but we had built 3 of the 6 or 4 of the 6, and so that’s when I realized we’re actually pretty close to marketing automation, even though I don’t want Drip to be that, or I didn’t want Drip to be that because it just feels really enterprise-y. It felt like a market we didn’t want to be in, kind of wanted to stay nimble and be a startup and do all that fun stuff and be able to call ourselves something fund, whereas marketing automation feels stagy and enterprise-y. But I realized that that is actually what we were becoming and that market was ripe for someone to kind of come in with good UX and UI and a slightly lower price point. There was nobody in this space, there was this big gap, and it’s kind of being above MailChimp and AWeber, in terms of constant contact and all the basic email marketing platform, being above them in terms of price and in terms of power, automatability and all this crazy stuff you can do.

And then, in terms of price and UX being – in terms of price being below Infusionsoft, but tried to be better UX because that was the main complaint I kept hearing, Derrick and I kept hearing that these big enterprise tools are so cumbersome, are so hard to use, they’re so hard to get started. So that was something from the start, it’s like this is our differentiator, it’s that we want to be in this space, but we are the lightweight version and we’re easier to use than the other tools you’ve tried.

Jane: And you had great success with that, congratulations!

Rob: Thank you! That was absolutely the turning point for the app. Then things shot up, revenue started growing very quickly at that point and now we’re at – we’ll be at 6 employees here in the next month or so.

Jane: That’s great, congratulations again!

Rob: Thank you!

Jane: So as of today, does it feel like you have a truly mature product, or do you have like big plan on expansion, future growth?

Rob: I’d say both, to be honest. I mean, Drip is very mature in terms of how much it can do, and the core value proposition of being able to manage your email and handle all automations you need, moving people in and out of lists, based on clicks – very advanced stuff. We basically spent multiple man years, several man years cause we had 3 people working on it full time for quite a long time, 3 developers. So we’ve cranked out a ton of features. At the same time, there are things on the periphery that I think we’re still in discussion about adding on whole new areas like a visual builder. We always have this discussion – should we build CRM into this or not? And that would be a whole new kind of piece to add unto it.

Jane: What is your long-term plan? Let’s say 5 years of Drip, how do you see that?

Rob: You know, it’s funny, I don’t make long-term plans because I mean the long-term plan is growth, it’s to get big. Not in terms of headcount, but just to keep revenue growing. But in terms of like feature roadmap and that kind of stuff, we plan maybe 3 months out. I think I have a loose game plan on what the next 6 months might look like, but things just change too frequently in this space, especially – we’re in a pretty crowded space, it’s very competitive and so, we’re keeping our eye out on what other folks are doing and what our customers are asking and we will – we have priorities certainly in our issue tracker, but I can’t even imagine what would we building in 12 months, much less 5 years down the road.

Jane: Alright. Do you plan to build like a suite of applications, or just focusing on Drip?

Rob: Focused on Drip. Let’s say we were to add CRM or add something that is not necessarily core to email marketing. It would still be within Drip, but it would be probably separate price module that you’d add on, and it would be so that if you didn’t need CRM, it wouldn’t bother you in the UI. We’re not going to add it, we’re not going to embed it into the app so that everyone wants to do email also has to look at CRM. So it would be under the same umbrella and under the same code base, but we would separate it out enough that folks who don’t need that functionality wouldn’t be bothered by it.

Jane: By the way, I’m really impressed by the actual brand name you picked for your product. How did you nail that down so easily that it’s called Drip?

Rob: We agonized over it. I have a list of potential names, like 50 different names, including like such bad stuff, like Velvet Mail. Courier, I think was available at the time. And Courier is a cool name cause it’s delivering email and delivering stuff, but it’s hard to spell, I think is the biggest issue. And we were debating it and I was discussing it with Jason Roberts from the TechZing podcast, and he and I were hanging out in Pasadena. And he went to – we were actually eating lunch and he went to the bathroom and he came back and he said ‘I have the name of your app, it should be called Drip’. And I was like ‘That’s genius!’ and he said ‘Name the generic’ is what he said.

Because drip marketing, it’s funny how common it is and how much we hear people talking about it now. But that phrase it was just kind of coming to the forefront. People were not talking about it nearly as much as they are today, and so it was a really cool name, I knew it right away when he said it. And then he went on and searched and found that – a 7 letter domain name was available via registrar. So it was a big win.

I actually was punching, was on my phone downloading the GoDaddy app cause we were at a playground with our kids and I downloaded the GoDaddy app and then I couldn’t remember my password, had to reset my password and I was really furious because he had searched for it and I knew that that meant, once you search for it there’s a potential that someone within the company would go buy it, like sometimes you’ll get domains swiped from you, and so I really wanted to buy this thing now. And so I was in a big hurry and I registered it, within an hour of him doing his initial search I bought it from my iPhone in the middle of a playground.

Jane: Yeah, that’s a real success story. Congratulations!

Rob: Thank you!

Jane: So, these days, now that the product is more stable, how often do you do customer interview and how do you plan on features and how do you sift through those requests daily?

Rob: Yeah, I only do customer interviews as needed when we have questions about features that we’re building. Because the number of features that are in our queue, there are probably a couple hundred that are in the feature request – the tracking, it’s called Codetree. And it sits over GitHub issues. And when we come to an issue that we feel like we need customer input on, I will either call someone or email them cause I know our customers well enough at this point that I know someone who will really want to use it. And either someone has requested it, or I’ll know someone who will think it’s a great feature and then I’ll go and ask them.

But the nice part is that we are such avid users of our own software that just within the office, we have a decent idea about how features should work. Because if you think about it, not only are we using Drip for Drip, we use it for HitTail. I use it for Software by Rob, my blog, so I have that use case of kind of the blogger, I’m an author as well, I have a book. So that use case is there. I run MicroConf, so we have the conference use case. I have a podcast, called Startups for the Rest of Us, so we have the podcast use case. I have a myriad of different use cases and it’s only if I need to go – we have some folks who are like brick and mortars, who are coaches and consultants, it’s if we go outside of our areas that in 10 days I get on the phone and interview someone.

Jane: By the way, how focused are you on a certain persona for your marketing, or do you target those niches that you just mentioned, which are much wider?

Rob: We tend to target verticals. There’s really good use cases for any type of SaaS or software sellers, companies to use Drip. SaaS and software is a big one, info marketers/authors/professional bloggers – kind of that market folks who are selling digital products online in essence is another big one. And then consultants and agencies is the third, and then WordPress developers. That’s as persona as we get, because to be honest, if you were to ask me for a persona to each of those, I would probably name a real person cause we have – you know what I’m saying? Because I know our customers so well, because I see them twice a year at MicroConf, and we’re hanging out on Twitter together, we’re on podcasts together. We don’t have like the traditional, have a piece of paper and generic name and kind of description of who they are. And maybe, as I bring new people on we will need that, because they don’t know the folks like Derrick and I and the rest of the team do.

Jane: Right. By the way, it’s great that you mentioned using Drip by yourself because I’m quite sure that plenty of founders don’t actually boil down to – they don’t sit down and use it daily, which really brings a wall between the user and the builder.

Rob: I agree. I know that I’ve had products that I don’t use daily, I owned several of them, and the usability is definitely not as good as Drip. I mean, the fact that I’m Drip every day, I notice little, tiny things that may not bother other people and we get those fixed and it keeps the product really operating kind of at a high – at an optimum rate, I think. Keeps the UX and UI up. And then, it also gives you the mindset of what your customers are hopefully thinking and what is interesting is we’ll get feature requests that we’d never thought of internally, and the biggest thing when we do get these feature requests is to come back to the customer and say ‘Thanks for this, what is your use case?’

Asking them for their use case and how they’re going to use it is probably the no.1 piece of advice I would give to someone trying to decide what to build. Because your customers don’t tend to know software as well as you do, and so if they suggest features, odds are that it’s not actually the feature you should build. What you really want to do is get at the problem that they are trying to solve by asking for that feature, and then you decide what you should actually build into the product, and that’s how you’re going to keep that level of UX.

Jane: Right, so do you consider Drip being an opinionated piece of software?

Rob: Oh, absolutely. Well it’s because Derrick and I are quite opinionated about the software we use, and when we use crummy software, it’s frustrating. So we definitely have high standards for anything we use and how it looks, how it feels and we have a lot of opinions. And we do get feature requests that we just say outright no, we will absolutely not build that, that is not on the roadmap. And if you need that you need to go find an app that does it and we typically recommend someone.

Jane: You’re just so lucky to be so confident about that, because I’m sure plenty of founders are just so hesitant about these directions to go.

Rob: Yeah, I think it helps, we’re now almost 3 years in from the day we broke ground on the code, and so, you gain confidence in this over time, especially as hundreds and then thousands of people start paying you to use the app and rave about how good it is, then you’re like okay, we built something that people want at this point and so, our vision is coming to fruition here and we can trust our instincts because we just have 3 years of that knowledge. You have it in your head, of the vision and the direction it should go, and you know that what you’ve done so far is working, and so you gain confidence that the decisions you’re making are working out.

I think at the start, or I know at the start we had a lot – there’s a lot more discussion and agonizing over what should we build, what are we building, what’s the best direction to take it. In fact, we documented all this in an audio documentary. It’s about 90 minutes long, maybe 2 hours. It’s at and it basically, it was recorded over the course of 9 months and then I edited it way down, but it’s just these weekly phone calls that Derrick and I were having discussing Drip and there are multiple times during those two hours that were pretty agonizing for me to hear because we were just so indecisive and kind of not knowing which way to go.

Jane: Is there any quantity and not quality way of telling which features are good and which are not? Like any objective filter you can apply?

Rob: That’s a good question. I don’t know of like a numeric way to do it. I think as the product gets more mature you can have your team – I’ve heard of folks doing kind of a market place idea where let’s say you have a team of 4 or 5 people, you come to the whiteboard and you write ‘We’re trying to plan the next few months, here are 20 features’ and everyone gets a certain amount of votes, almost like a user voice thing, where it’s like you get 8 votes total and you can put a maximum of 3 on any one thing. I’ve heard of folks doing that, and that would be a fairly quantitative way to get, at least within your team, a ranking of what you should build.

We’ve never done that because we don’t do a 3-month block. We really build, we deploy multiple times per day. We’re rolling multiple, many, many features per week. Some are really small, some are larger, so it’s kind of a really fluid ongoing process, so we use less of a numeric way and we use more of a – it’s more of a filter where the first question is does this fit with our vision of the product? As founders, does this fit with what we want to build? The second one is: do we think at least 90% – I’m sorry, not 90 – do we think at least 20% of the people who are currently using Drip, do we think that they would use this feature? And at that point it’s just a best guess, because if it’s less than 20, if we’re gonna get 5% of people, we really – we don’t like to clutter the product and so sometimes we’ll actually gate it behind like a checkbox in the admin area. We have a couple of features that are in Drip, but no one can see them unless you request them.

Jane: I know about it, I just heard that from Derrick. This is spectacular!

Rob: Yeah, and it’s to keep the product simpler. Some features people can easily hurt themselves with cause they’re fairly advanced, and other ones just clutter the UI to the point where we didn’t want that to happen. So we’ve used multiple – there’s a lot of filters and a lot of questions that we ask and it is based on, there’s a little bit of intuition, a little bit of gut feeling, which is a bummer. I wish it could be more numeric, but that’s kind of how we do it when we’re moving this fast, I think that’s the best way we found.

Jane: Right – these are some really good questions to filter that out, actually. This should be put on a big board, your head in the office or something like that. So in your product portfolio, Drip is certainly not the first and how was your product line? How did it look like before Drip and how has your experience affect the way that you built things these days, as opposed to your early products?

Rob: Yeah. I kind of had two sides to the stuff that I own, the products. There’s the personal brand side which is my blog, podcast, conference, the book and The Micropreneur Academy which is an online membership website. And then there’s the software side, and I’ve owned things ranging from e-commerce websites to product and consulting services. Most recently, I think as of 3 years ago when we started Drip, I owned HitTail, which is a SaaS app, a long tail keyword tool. I owned DotNetInvoice which is one-time sale downloadable invoicing software, it’s web-based software you download. I owned Wedding Toolbox which allowed people to build wedding websites and there’s one other, Apprentice Lineman Jobs which is a nice job for electricians. I have since sold or shut down or given away all of them. The only thing I own today is Hit Tail and Drip in terms of software. And the reason I’ve done that is because Drip, it’s just a bigger – when you start growing in one month more revenue than all of your other products are making or any individual product is making and you’re growing that fast, it’s like it doesn’t make sense to hold unto that thing. So DotNetInvoice was a partnership and I just gave it to the other partner and the other ones I sold or shut down, as I said.

None of those other — and to get to the second part of your question, which was how do I build software today compared to what I used to do – I think the stakes are higher with Drip because A – Drip is a much larger, more ambitious effort than anything I’ve done. I liked, tended to want to 10x my previous, 5 or 10x my previous efforts, so early on something was making $1,000 a month, and I said what can I do to make $5,000 a month, and then actually my next step was up to about $25,000 a month. So that was I guess more of a 5x thing. And then the question after HitTail was to say what’s 5 or 10x this size? And certainly going into marketing automation space, there’s room to do that, and given the growth we’re on trajectory. So since the stakes are higher, this is the most complex piece of software, the most complex app I’ve owned, and it’s also I think the one I’m focusing on now. In the past, I’ve had multiple apps at once and balanced everything and that’s really going away these days. When you’re building something this big in a space this competitive it should be all you’re focused on. And that’s how it’s different, you know is that basically, I’m all in on this, aside from still running the MicroConfs and doing a podcast, this is really all that I’m working on. I’m not spending time on HitTail and I don’t have any other apps anymore.

Jane: Right, so staying focused is one more important thing that we should keep in mind.

Rob: I agree. I think that entrepreneurs, it’s a very common mistake to make, to try to do too many things at once and to start two things at once is a terrible idea. I see folks trying to launch two apps, it’s just way, way too time-intensive.

Jane: So with Drip you’ve been lucky enough to have Derrick who’s a jack of all trades, who’s hauling the whole cycle, but had you had experience with a different, separately designers, developers in the past? So some input on that?

Rob: Yeah. I mean, you just have to become a project manager and you have to fill in the gaps. Luckily, I would have a designer design something and then I’d have someone slice it and put it in HTML/CSS and since I’m not a designer for sure, but I know enough about HTML/CSS that if there’s something jacked up I can help with it or fix it, then I would have a developer put the code behind it and luckily, if that got screwed up, or that needed maintenance or anything like that, I can fix that. I know and Pearl and a bunch of other stuff – so I think that becoming a project manager and allowing and just keeping folks motivated and being able to curate their work I think is really important.

I think the more you know about what your contractors or employees – that’s the case, maybe – the more you know about what they’re doing in terms of technically, I think by far the better off you are. You don’t need to become a production developer or a production-ready designer or a production-ready frontend developer, but being able to sanity-check things and dig into it a little bit, and even make some changes here and there I think is important, especially if you’re working with several contractors who are not necessarily affiliated and you’re passing stuff between them, there are going to be things that fall through the cracks. So you either need to fix those, tweak them yourself last-minute or have someone that you can call on and help you on short notice.

Jane: Yes, once again, technical background can be incredibly great. This is a weird place to ask, but can you share some biography facts of yours, like what life have you gone through to become such an effective product owner?

Rob: Well, I mean I’m a software developer by trade. I started writing code when I was 8 years-old on my Apple 2E, learned the BASIC and the built text-based games back when Zork was big. And I became – I graduated from college in the late 90’s and was during the dot-com boom and I lived in the Bay Area, so anybody with a pulse could get a job coding. So I worked for a consulting firm who was building dot-com websites, and so within the course of 2 years I had to learn I think 6 different programming, web programming languages just because whatever the client needed, that’s what I did. So I did PHP and Pearl, ASP Cold Fusion, Java and then landed on .Net.

Jane: Oh my! This is impressive!

Rob: Isn’t that crazy? I mean, I’m not an expert in all of them, but I built production websites with each of those languages, built or modified for sure. So that was it. And then was the big dot-com crash, so I did a lot of consulting over the next 6–7 years, both in kind of high-level technology stuff, but I did a lot of coding, a lot of C#,, some PHP and slowly tried to improve my front end skills and then started launching products really in the early 2000’s and had my first moderate success that did a couple thousand dollars a month in 2005 with DotNetInvoice and since then launched or acquired a bunch of different small web properties and I quit consulting altogether around, I think it was 2007–2008 where I had enough income from products that I was done for life, you know, in terms of doing the consulting stuff. And now I’m, like I said, from there I then tried to level up each time. Build something a little more ambitious, not just for ambition’s sake, but really because it keeps me interested. I think a lot of us are life-long learners and perpetual learners, and that’s what we thrive on, and that’s what success it to me, is to be able to work on what I want and to be able to learn however much that I can feed my brain, cause that’s when I’m happiest.

Jane: Absolutely! That’s one of my credos as well; it’s great to keep learning in different areas. So, business and marketing skills are self-taught? Is that right?

Rob: That’s correct, yeah. I didn’t go to school. Just by a lot of trial and error, a lot of reading, obviously. I mean I was learning online marketing probably starting in 2004, so there were really no podcasts on it. I was actually taking – there was no startup marketing space. Right now there’s like people who are building courses for startups and don’t have marketing and software products.

There really wasn’t so much then, so I read lot of Joel Spolsky, I read Eric Sink which had some of that, but I also borrowed a lot from kind of the info, the direct marketers and the information marketers like, let’s say Dan Kennedy or Frank Kern and those guys. But I took what I liked out of it – I don’t agree with a lot of the stuff, I feel like they go a little over the top and it feels a little ethically dubious at times, and so I try to take the lessons that they were teaching and then put my own spin on them and make them feel more comfortable with my personality and my approach, the approach I want to have to business.

Jane: Right, so having seen so many things come and go, do you have some kind of sense for those emerging opportunities, emerging new markets or new trends? Is there any verbal criteria you can define?

Rob: Do you mean like marketing approaches that are working better?

Jane: Like, in general. For example, with Drip it was clear that the marketing niche was empty at that point, and you just nailed that entry point into that niche. And how can other people stop those emerging markets right now, for example?

Rob: Oh, boy – that’s a tough question because we didn’t even see it until we launched, and had our app in product, people paying us and then saying ‘I really want it to do that’. So it’s almost like, I think it comes back to something I said for years, which is do things in public. And by that, I mean publish a blog, write a book, do a podcast, throw a conference and even a meet up. Launch an app – even if it’s open source, get stuff out there because as soon as you start doing that, that’s when people will start to comment on it, they’ll say ‘Oh, that’s great – but could it do this?’ or they’ll say ‘Oh, this is a great opportunity – can I hire you to help me with that?’

As soon as you start doing things in public, A: you start getting over the fear of doing things in public, which is a really big deterrent for all of us, and B: that’s when things start to happen and that’s when the opportunities arise. And I think that standing on the sidelines and reading Tech Crunch and Venture Beat and Inc. Magazine, you’re not going to see anything that other people aren’t about as well. And that’s not where the opportunities are. The opportunities are when your feet are stuck in the quicksand, and you’re the only one there and you’re the one trying to figure out where to go from there, but you’re getting this proprietary input.

Because if you launch an open-source project or you started a software app, people giving you feedback and suggestions on that, they can be invaluable, right? They can be gold, which obviously was the case in our situation because helped us move into marketing automation, but no one else was hearing those. Because it wasn’t written in some Venture Beat article. It was sent directly to us because we were the ones that had taken the risk to launch the product. So I think that would probably be my piece of advice, is to do things in public and that’ll get you on your way.

Jane: This is great. I was going to ask for some piece of advice, but this is just it! Any other piece of advice in regards of building things? Like how to make it as painless as possible?

Rob: I think that – I think learning to outsource is a big one that a lot of us don’t want to do, especially if you are a full stack developer or someone who can do multiple things, who can design and do front end work and do back service-side work, and write copy and all that stuff. I think learning to let some of that go is a piece of advice I would give to people.

Every entrepreneur or developer or designer I’ve spoken to who’s launched a product and needed to support it long-term, everyone I’ve talked to who I eventually convinced to outsource some part of it, whether it’s support or whether it’s some of the front end work, or some of the back end work, I’ve never heard them regret it in the long term. Maybe in the short term there’s some stumbling in trying to find that person to help you and say ‘They can never do it as well as I can’ or ‘Well, I only spend one or two hours a week on it, it’s not worth to outsource’ – these are all the typical things that go through our head. But as soon as you are able to let that go, you are able to focus on the things that really matter to your business and your business is going to grow faster.

Jane: This is amazing, thank you! Do you consider yourself a perfectionist or not?

Rob: In general, yes. I’ve had to let some of that go. I think it’s funny, being a perfectionist – I’m just a very detail-oriented person so I see when there’s things that are not right. Especially when you’re a software developer, especially like you are looking for things that are wrong because that helps you debug your code, and it helps you have code that doesn’t crash with edge cases. So I’ve always been that very meticulous kind of find all the things that are wrong with things. With that said, I realize that if I have someone on my team to do something, I may be a perfectionist in the fact that I want it done a certain way, but they might do it in a way that doesn’t match up with that, but it doesn’t mean that it’s not as good.

If there’s a glaring area, there’s copy that’s cumbersome, or there’s a more elegant way to do it, we’ll talk about it. But I found that people will come up with ideas, especially if you have good people, they’ll come up with ideas and ways to do things that are different than what you expected. But they’re often as good, or better. Even though in the early days of doing this, when I was just getting started, if it was in any way different than what I had envisioned, then it was ‘wrong’. You know? And I think getting over that is probably a big win.

Jane: Right. So, Rob, I think it’s all I have for you today. And your advice has been amazing, I’m sure. Our listeners will take away so much.

Rob: Thank you.

Jane: And try to apply it. So tell us a few links where people can find you online?

Rob: Sure. If you like consuming audio content, I put out a 30-minute podcast every week, and we’ve done it for 5 years straight and it’s talking about all this kind of stuff: it’s about marketing, it’s about launching products. It’s called Startups for the Rest of Us and you can search for us in iTunes or go to And then on Twitter I’m @robwalling.

Jane: Thank you so much for coming today. I’m sure it was great, and I hope you just conquer all the best heights with Drip further on.

Rob: Thank you, I appreciate it. I also wanted to give folks a special, like a coupon code for Drip.

Jane: Great, let’s do that.

Rob: At the end of the show, I basically want to give folks, normally we have a 21-day trial, but if anyone’s interested in upping their email marketing game, and checking out the UI that we’ve been talking about here for 40 minutes, we’ll include that in the show notes and we’ll double their trial so we’ll give folks a full 6 weeks to check it out.

Jane: Yeah, that will be a special document for each interview and it’s going to be there.

Rob: Sounds great!

Jane: Awesome! Thank you, Rob.

Rob: Thanks, Jane.

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