Rob Walling of Drip

Jeroen: Hi Rob, it’s great to have you on Founder Coffee.

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

Jeroen: You’re the former Founder of Drip; now working on Tiny Seed, right?

Rob Walling: That’s correct. And I think former Founder sounds funny. I will always be the Founder, I just don’t work there anymore. I’m the former CEO, you might say.

Jeroen: Former CEO, yep. How long did you work there, after the acquisition?

Rob Walling: Me and my co-founder sold Drip to Leadpages in July of 2016, and I worked for about 20 months for Leadpages. And then I left just about seven months ago.

Jeroen: Cool. So on to new challenges, then?

Rob Walling: Indeed. I thought I was going to be on to early retirement, but of course, that’s never how it works out when you’re a serial entrepreneur. So I knew I would do something next, I just didn’t know what it was. But I’ve since landed on Adam, so I’m sure we’ll talk about that today.

Jeroen: Yeah, let’s first zoom into Drip perhaps. What is Drip doing?

Rob Walling: Drip started as just a little; let’s say it became an ESP, an email service provider like Mailchimp. But it started as just a little add-on widget that almost added on to Mailchimp or AWeber. And then it became a full-fledged ESP where you could send broadcast emails or even manage your list. Then we added automation to it, and so it became like a next level, like a Mailchimp plus. So people would upgrade to Drip from Mailchimp or AWeber. We were more in the area of Infusionsoft or Active Campaign, as a true automation platform.

And as I said, Leadpages acquired us in 2016, and since then there’s just been more doubling down. There’s a whole visual workflow builder, and all types of crazy stuff you can do with it in there. Catering a little more towards eCommerce these days, but I still use it for all of my businesses. I run MicroConf and my personal robwalling.com list on it. And I have a new effort, Tiny Seed, and all that’s in Drip and it works really well for that. So it’s not like it doesn’t work for non-eCommerce, but I do think that’s more of a focus of their marketing these days.

Jeroen: Yep. That’s very interesting that it grew from a very small plugin, to then an email service provider, to then a sort of automation platform. Can you maybe go into the very early stages? Like why did you get started with this plugin?

And what problem was it trying to solve? And how did you guys get started? When was it that you said, “Oh, we have this issue here. We should really make something for that”?

Rob Walling: Yeah, totally. It was in late 2012, and I owned a SaaS app called HitTail. It’s a long tail SEO keyword tool. And I was growing that pretty well. It was kind of just a one person SaaS app, and I had a couple of contractors. It was very profitable and I was enjoying it, but I noticed that it was really hard. I got a lot of traffic to that site, and I noticed it was hard to just capture email. I just wanted to build the list faster.

I noticed that when I built the email list, it converted more trials. And so I went out and I said, “Look, I want just a little JAVA script pop up that could pop up either as a little toaster widget in the bottom right hand, or just pop up.” This is before SumoMe, before OptinMonster. It’s before everything that we have today – that whole ecosystem didn’t exist.

So I had a contractor named Derrick who worked for me, he was a developer. And I said, “Hey, can you grab an open source something or other, library?” And I think he grabbed jQuery and built this little pop-up widget. Then we pumped it into Mailchimp and did an autoresponder sequence, that was really just an email mini-course, educating people on long tail SEO. It took him almost a week to do this because he had to hack a bunch of code and he had to design and do all this stuff. And I was thinking, this is nuts. This is stupid that this isn’t simpler to do.

It bumped our conversion rate way up. We started converting 30% more of our unique visitors to trial. It took them a little longer because they would go through the course and about three or four emails in they would then sign up.

So I was like this should be a SaaS app, basically. So that’s when we said all right, let’s build. I grabbed Derrick and said, “You know Ruby on Rails. Go build what you just built, but build it as a standalone SaaS app in Rails. And what we’ll do is we’ll just have the front end email capture and we’ll pump into Mailchimp or AWeber.”

We also built our own little autoresponder engine that was pretty rudimentary at the time. I started building a list, once we kind of had that idea and I knew where we were headed. And so I built an email launch list of about 3,500 people over the course of 2013. We kind of started launching in mid-2013, really slowly, just to get people in. And by November 2013, that was when I did the big push to the rest of the list.

Jeroen: Yeah. So if I heard it well, you started because it was very difficult to make a sort of Optin pop up for your site, right?

Rob Walling: Yep.

Jeroen: And you made something that pushes that to something like Mailchimp?

Rob Walling: Yeah.

Jeroen: But then very quickly you also figured that you could make your own autoresponder. What was it that drove you to do that?

Rob Walling: Well, to be honest, I’ll say we actually launched with our own autoresponder. That was the initial goal because we wanted to be kind of self-contained from the start. But what we realized is so many people were using Mailchimp and AWeber, and they didn’t want another thing sending email for them. That request came through very early. I did a lot of customer development, a lot of emails and phone calls and demos and stuff. And within the first 10 or 15 people who were kind of willing to pay us, they said, “You know, I really just want to keep everything in one place. Could you, when you capture the email, could you just pump the person into Mailchimp and then do it that way?”

And we said, “Sure, why not.” So we built that integration, and then we built AWeber.

Now, later on, we became an ESP – it was really late 2013 or early 2014. So it was about a year after we worked on our code. Then we undid those integrations because now we were basically competing with them and it didn’t make sense for us to continue offloading our subscribers to a competitor.

Jeroen: Yeah.

Rob Walling: So it was quick. I don’t know if you’d call it a full pivot, or just a development of the product, right?

The early days, when we launched in November of 2013, I emailed the list and we got up to about $8,000 in MRR in basically our first month live. And I was really happy with that. I viewed it as kind of a lifestyle business. The problem was, though, is as I was pumping top of funnel traffic and prospects into the app, it really wasn’t growing. There was just way too much churn.

So over the course of about four, five months, so into early 2014, I got it up to about 10,000 or 11,000 MRR. But I was really spending a lot of time marketing it, and a lot of effort. And it should have been growing a lot faster than that. Churn was 15% or something a month.

Jeroen: Wow.

Rob Walling: And I knew that we did not have a product-market fit and that I was basically making up for the lack of building something people want with just having a lot of top of funnel traffic.

Jeroen: Yep. So actually you could have built this into a full pop up solution or something?

Rob Walling: Could have, at one point.

Jeroen: Something like hooked in.

Rob Walling: Yep. So we evaluated doing that, like completely going away from email altogether and just being a front end pop up, and doing all the, you know, there’s all kinds of stuff you can build with that: split testing, timing, scrolling, exit intent and all that. And in fact, OptinMonster, I believe, came around during that time, late 2013 or early 2014 too. They were first a WordPress plugin and then became a SaaS app. SumoMe, I believe, launched in 2014-2015.

So what’s interesting is we recorded an audio documentary that’s about 90 minutes long. And it’s basically every week, Derrick and I. He was the contractor who built it and later came on retroactively as like a co-founder of Drip because he was such a pivotal person. But he and I would have about a 15 minute chat every week, and we would record it, a voice chat.

We had about nine hours of audio, over the course of the year, of the agony and the confusion of launching this. And I edited that down to about 90 minutes, and you can hear there’s a whole segment in the middle where I’m saying, “What are we building? Who are we building this for? I don’t even know what we’re building anymore.”

It’s just kind of chaos and confusion. So that’s on the Start-Up Stories Podcast. It’s just one 90 minute audio file, but it’s pretty interesting and really goes in depth around that 2013 – early 2014 timeframe.

Jeroen: Yep. But then you made the decision to build an ESP.

Rob Walling: That’s right.

Jeroen: And then you saw that automation was something interesting?

Rob Walling: Yeah, that’s exactly what happened. We started building the ESP features, and some very light automation. And this is before Infusionsoft was around. There really wasn’t a good alternative to them that wasn’t either a lot more expensive or a lot harder to use. So we had a few customers who said, “You know what if you could just make it so that when someone clicks a link an email that I send, that I can add a tag to that subscriber. Or I can move them from one campaign to another,” Just very basic automation stuff, that was very hard to do in Mailchimp or AWeber, or impossible to be honest, unless you use code and APIs and stuff.

We were getting customers saying, “If you could literally do like two or three of these automation things, I would switch from Mailchimp or AWeber.”

And that was a big flag for me of like whoa, I think this is where the space is going. Because at the time, I heard marketing automation, that phrase, for the first time in 2013. I didn’t even know what it was. And it became, it really grew during that time. So we kind of caught that wave.

It was a hard decision to decide to go into automation because it made the product no longer a lifestyle business. It made it very competitive. We were basically diving into red water where you had all these big companies with all this funding, and we were bootstrapped.

It was two guys working out of my home office. And it was like are we really going to do this? We’re going to complicate the product, not from even the front end, the backend’s going to become very complex too. It’s going to become a real SaaS app and we’re going to be going all in with two fists. And so I struggled with that decision for a while and eventually said I think this is the way to go.

Jeroen: Right.

Rob Walling: And so as we started rolling out automation, churn just plummeted. So it went from 15 to 12, to 10, 7 and 5. It just kept going down, down and down. It was funny, our trial count was going down during this time, and our MRR was going up because churn was dropping so fast. Because it was obvious, we hit in my vision. Product market fit, I don’t believe, is not a binary thing. It’s a continuum. And we were just crawling up that ladder over the course of about three or four months as we released new automations.

And so by the time we were in early to mid-2014, we had essentially become what I would call email marketing with automations. We weren’t a full-blown product with visual building and everything, but we were definitely a step above that basic ESP. And people noticed that we were an easier version to use as compared to the other more expensive automation providers. And it was crazy. Growth just kicked in, we were crazy all of a sudden.

Jeroen: So it sounds like you got into the start-up from a lifestyle business perspective, and then you started going into having a “very serious” business. Can you tell us more about what motivated you to get into these kinds of things? What was it that you initially saw as your goal when starting companies?

Rob Walling: Yeah, that’s a good question because I’ve run into a lot of people who want to start up to get rich, or they want to start a start-up for the power and the fame, and to make an impact. There are all these different reasons, and I don’t believe that everyone has the same motivation. So I’ve always been a maker. I love building things. And so from the time I was young, whether I was making stuff with Legos, or when I was eight I learned how to program. I started writing code then, and I loved building games. And I wrote booklets and books and would sell them through classified ads in the newspaper because making the books was interesting to me. Writing books about collecting comics and such.

And so as I got older, got out of college, and I started working for other people I realized I don’t like doing things that I don’t enjoy. So I go into a job, and I worked in construction for a couple of years. And then I switched to programming, and it was fine. I enjoyed it. But I don’t like building things for other people.

I thought to myself, how can I control my own time 24 hours a day, where I can do, and build, and make whatever I want? And that was truly the switch that flipped for me; like I think the only way to do that is to run my own business or to start a business and sell it for enough money that I don’t need to work anymore. And I can then just go and make whatever I want.

And for me, making companies is actually fun. Making software is fun. So I’m lucky in that respect, that stuff I do enjoy doing is profitable and creates value in the world. And so it has come back to me there. But that’s really what’s been my motivation.

I’ve never had the desire to run. If you asked me would you have enjoyed starting Facebook or running Uber or anything, I have no desire to do that. At a certain point, you have enough money that you can do whatever you want. Why would you keep running this big company? All the headaches, and all the stuff that goes along with it. And that’s just my perspective. I know that someone like Zuckerberg enjoys it and that is why he does it. But my motivations are very, very different.

Jeroen: Yep. Do you think he’s not someone who enjoys this building process?

Rob Walling: I don’t know. It’s hard to say. I mean, he certainly was building and launching a lot of things when he was at Harvard. So there was something in him that wanted to create. What I’ve heard on This Week in Startups is that Zuckerberg basically has almost no interest in kind of the operations of the company, and that’s what Sheryl Sandburg does, as his COO. And that he really focuses on the things he enjoys. So there’s something still there that he enjoys, and he’s probably able to make stuff.

You think about Larry and Sergey, too, with Google. They’re not sitting there working on the search algorithm anymore. They moved on to new, interesting problems. They’re makers, and I think they’ve kind of balanced that thing of “hey, we got really rich and we built a really amazing 100 billion whatever dollar company … several hundred billion”. But they have used that to then allow themselves to make other things, on a totally different scale than I’ll ever have the opportunity to do.

Jeroen: Yep. You moved on pretty recently to the world of VC funding, being an investor, right?

Rob Walling: In essence. There’s a path in 2011 where I barely had any money. I got an email from a colleague named Jason Cohen, who was a fellow blogger. We were in the start-up blogosphere. And he said, “Hey, I’m starting a WordPress hosting company, it’s called WP Engine. And we’ve been growing it for about a year, and I’m taking a round of investment. It’s a closed round, it’s oversubscribed. But if you wanted to put some money in, that would be cool.”

So that was my first Angel Investment, and I considered it quite a gift, to be honest, to be part of the first two rounds of WP Engine – which as you probably know, your listeners probably know, is now worth hundreds of millions of dollars, literally. Not my share, but the whole company.

Jeroen: Yeah.

Rob Walling: I’ve never raised funding, but I’ve never been anti-funding. I’m anti raising funding if you don’t know what you’re getting into. Raising funding if you don’t understand that you might be giving up control, or you don’t understand the motivations, or you don’t want a board but you’re going to raise funding and then be pissed off about it later, is a no-no. I see people do that, and I’m like don’t do that. Just don’t raise the funding if it’s going to be a problem.

I’m also anti everyone thinking that the only way to start a SaaS or software company is to raise funding because I don’t think that’s true either. But at the same time, I have plenty of friends who have either raised funding and it’s been a great experience for them, and I’ve done myself about a dozen Angel investments over the course of the last seven years. About half of them are in companies that are on the more Silicon Valley trajectory. And about half of them are with colleagues who are going to grow really solid, probably to a seven-figure SaaS business. And those, the profit margins on SaaS is very nice. I don’t think it’s a bad idea to take, like several of these folks did, take a single round of maybe 200 grand just to get you started faster. Then once you get to profitability, you can cut dividends, or you can buy the investors out, or you can sell the company and everybody makes out. I mean, those are the three options.

I would say I’m less of a venture capitalist because that has a certain connotation, you know what I mean? Especially in my circles, right, my bootstrap circles. I’m much more about building companies rather than building slide decks. But I still believe that you can build a company and raise kind of a small round, to help you move faster in the early days. Then maybe you don’t lose control of your company. You don’t have a board, you’re not taking institutional money, and you don’t have to raise another round if you don’t want to. I think the big turning point, is once you’ve raised money from a venture capitalist, it’s implied that you’re going to raise again every 18 months until you either explode or you’re worth 100 million or a billion dollars.

And that’s not the type of game I’m in at all. The cheques I write are for people to be like, “Hey, let’s build this up into a nice, seven-figure SaaS app.” And we’ll all win, no matter what you do. You can cut dividends. As I said, you can cut dividends, you can buy us out, or you can sell the company – any of those three are cool with me because we’ll all do well with it. And so that’s the model I’ve moved into.

I got to be honest, I’ve been writing cheques, but I don’t have an infinite amount of money. I had a modest exit with Drip in the sense that I don’t have to work again, but I don’t have infinite pockets to be able to fund as many companies as I think are worth funding, and want to go on this path.

And so about four-five months ago, I started talking to a friend of mine, a co-founder who’s in more of the finance space, and we decided to raise some funds. It’s a small fund, but we’re calling it Tiny Seed, tinyseed.com, and that’s to allow me to put even more money where my mouth has been for several years. Just to be able to fund more of these types of companies.

Jeroen: Just before this, we talked about your motivation, which is mostly based on the joy of making things. How do you find this back in what you currently do?

Rob Walling: Oh, that’s a good question. So there’s something about creating something novel and unique that really excites me, as a maker. And if you look at Drip, the first iteration was not that. It was kind of novel and unique, but as we got into it, we were really pushing the boundaries of what people were doing with automation. And that was super fun.

Tiny Seed is a similar thing. It is building a fund or building an accelerator – it’s actually a remote accelerator, that is, frankly, completely new, because there are no year long, remote accelerators that are going to focus on mostly SaaS companies that will be in the seven or low eight figures.

Let’s just say one to twenty, one to thirty million dollar ARR is kind of our goal. And that is cool to me because it’s a gap in the market and it’s a problem that no one else has tried to address to date. And so there’s creativity in it.

So when we look at, okay, so how do we structure these terms? Well we can’t look to venture capital, because they structure things a certain way and that’s not going to work in this model because the returns are totally different. Because we’re never going to have a Dropbox, or an Airbnb, or an Uber, much like Ycombinator, 500 Startups, TechStars, they’re going to have these outliers that go to a billion dollars, multi-billion, and those that are going to return the fund. Well, we’re not going to have those, based on our thesis.

And so then the question becomes how do we creatively address that? That’s the part that excites me – thinking through hard problems and coming up with cool solutions, where there’s no roadmap. I can’t just go read a blog post about how to do this, we just have to think about it, model it out, and then talk to founders and be like, “Does this sound reasonable? Does this sound fair to you? And does this work for the model?”

Jeroen: And what is like your end goal now? How long are you working on this now?

Rob Walling: I’d say like four or five months.

Jeroen: Four or five months, so it’s very early stages.

Rob Walling: We launched about two months ago, so yeah. But we’ve raised enough. The money we raised came faster than I thought it would, to be honest. So we raised enough to run a cohort, like a batch of 10 startups in 2019.

Jeroen: Do I know some of the startups that are a part of it?

Rob Walling: We haven’t selected yet. We’re opening applications in early, in Q1, 2019. So the next month or two we will. I’m doing some early conversations with folks that I know personally and assessing things out. I think we’ll be picking at least a couple pretty soon. But yeah, then the application process will start.

Jeroen: Right. Do you have any idea already of where you see this going, or are you taking it very much step by step and you just want to get this off the ground first?

Rob Walling: No, I think the natural progression of it will be run this first batch with probably 10 companies, maybe 15. As I said, it’s a year long. And as we even get a couple of months into that, I think I’m already starting to think about “do we want to run multiple batches in parallel”? “Do we start another batch six months in”, or “do we just run them back to back”?

I would also love to increase the batch size. I would also love to change geography. Like right now we’re probably going to focus on the western hemisphere, because of the time zone issues, because we’re going to have calls every week. But I’d love to think about could we do one in Europe, could we do one in Asia? I mean, that’s the expansion idea, right?

And so I try not to get ahead of myself in general, I’m pretty pragmatic. So I’m not saying, “Oh, we’re going to next year have 20 different batches of 100 companies,” because that’s just nuts. But I do think ultimately that this expands in all directions – it expands geographically, and it expands in terms of the number of companies we can pull through.

Here’s the difference, most accelerators are three months long and you move to a specific location for them. You need to have a company that can basically be a unicorn, have a billion dollar valuation. Typically that’s what you need to get in. So once we’ve undone all of those assumptions – you don’t need to be a unicorn, you don’t need to move somewhere, and it’s going to be a year long so it allows you a lot more time growing a SaaS app because SaaS apps take so long to grow. Well, the number of companies that fit that description is actually quite large, because as soon as we remove the geographic limitations, it gives us a lot more of a pool to go through.

So I believe that there’s going to be no lack of companies that are going to be qualified and worth helping through this Tiny Seed model.

Jeroen: Yep. It’s mostly a software as a service business that you’re focusing on.

Rob Walling: Yeah, I would say so. Frankly, my expertise is B2B – small to medium sized SaaS businesses. I’m not ruling it out, but I’m guessing it will probably be 80-90% that.

Jeroen: Right.

Rob Walling: It’s just such a predictable model, and it’s repeatable. There are all these pluses about it. Yeah, I think that’s where our sweet spot’s going to be.

Jeroen: Sounds cool. In this whole journey you had with Drip and now Tiny Seed, is there anyone who particularly inspired you or that you’ve always followed?

Rob Walling: Yeah, kind of folks who I look up to, right?

Jeroen: Yes.

Rob Walling: Yeah, kind of model myself after. Sure. I’ve always had a ton of respect for Jason Cohen, the Founder of WP Engine. He blogs at asmartbear.com. He’s spoken at my conference. So I run MicroConf and he’s spoken there several times, and he just always delivers amazing talks. So I respect his thinking a lot. He’s a very pragmatic thinker. He’s also that interesting mix of a theoretical thinker, but also an operator. He’s built amazing companies.

There are very few people that do both. We can think of folks who write books about startups that never actually start one, and they’re the theoretical ones. And you can like some of them and not. Other times it’s like well, you don’t have any credibility with me because you haven’t launched a startup.

And then you have folks who are operators and founders and they can launch stuff, but they can’t get up on stage and tell you why it worked. They just do it, you know what I mean? Whereas he’s that mix of both sides of that, which is pretty impressive.

Jeroen: Mm-hmm.

Rob Walling: I also respect Hiten Shah a lot. I respect his growth mindset of being able to grow companies. I respect how he treats people. He values relationships over results. And his ability to start multiple products and make them all successful is pretty damn impressive.

Jeroen: Talking about how people are both strong on the theoretical and operator side, what is it that you currently do concretely at the operator side, let’s say? What is it that you do to build Tiny Seed’s fund and as an accelerator? What does that entail?

Rob Walling: Yeah, like kind of day to day, like what am I focusing on?

Jeroen: Mm-hmm.

Rob Walling: Yeah, it’s really interesting. I mean, it really is just another startup. Like it’s just the next startup in my inventory. I’ve been starting them since 2000, so that’s what, 18 years I’ve been launching these things. But my first success was really 2005, so you might say it’s 13 years.

But it’s two of us working on this thing. At this point, we have funding committed verbally but we don’t have funding in bank accounts. So we’re totally essentially bootstrapped. It’s very interesting that starting SaaS apps is much more about we have to get in the code, we got to build features, we got to figure out what we’re doing. This is so far different than that, and this is much more of me – I’m doing meetings, I’m doing phone calls, and I’m doing email to a lot of people we need to connect with.

So it’s much more about doing essentially customer development with other founders. It’s finding out who might be interested in becoming a part of Tiny Seed as a founder. It’s talking to investors. I’m not heading that part up, but I’m definitely weighing in on that. It’s sitting down with my Tiny Seed co-founder to figure out “okay, what would the terms look like”? We had a call a couple days ago, we’re trying to nail things down there.

It’s much more about, I don’t know, it’s like my personal network and my audience, and kind of bringing folks. In all honesty, it’s sending a lot of emails, which traditionally I would not have enjoyed. If you look back five years, I would have complained about being in email all the time. But there’s something interesting and exciting about it. And I think it’s just moving the needle forward, you know?

Jeroen: Yeah.

Rob Walling: It’s like pushing this thing forward that if you don’t do it, no one else will. And that’s what I’m doing. So I’m just thinking about all that stuff. Literally yesterday I got in touch with a design agency because we need a logo and a website.

I sat down and I built the site map out for what the site’s going to look like. What are the 12 pages we’re going to have on our website, thetinyseed.com? Because right now it’s just a landing page. And so I scheduled a call with them.

That’s an example; it’s just a start-up. I’d do that if we were a SaaS app too. I would do the exact same thing, we need a logo. So there’s nothing magical there.

The difference is we are talking to investors, and I’m essentially interviewing founders. But it’s kind of like I’m meeting with and interviewing and talking to them, which is something I’ve done for years, but I’m just doing it with more intention now.

Jeroen: You were saying that it’s a bit different than a SaaS company. Do you think that it is so because in a SaaS company we tend to believe that the product is everything and that all the other things are kind of secondary?

Rob Walling: I would agree with that, yeah. Especially for someone who’s a maker. If you’re a developer or a designer, we do tend to think the product’s most important. And when I think back to building Drip, I spent, especially in the early days, it was like 90% of our time, on it. Well, that’s not true. Derrick had 100% of his time focused on the product because he was coding and designing. And for me, it was probably 75% of my time thinking about the product.

I was talking to customers, to be fair. But I was talking to them to figure out what to build next and how to build it, and if they were happy, and all that. Then I spent about 25% of my time doing marketing. Later on that got bigger, as we launched. Marketing became half my time or more of my time.

But definitely, the product dominates when you’re launching a SaaS app or any software product. It is so important to get product right. And if you think about us, what is our product? Well Tiny Seed’s product is our offering to investors and our offering to founders, and how we package that, how we position it and market it.

Even just sitting down and writing an essay or a manifesto type of thing about “hey this is what we’re doing”, and “this is why it’s new and unique” and “why we think it’s going to work”, that itself is the product – you might call it marketing. It’s a way to position the product to whoever I’m writing the manifesto for.

Jeroen: But don’t you think in the case of a SaaS startup this should also be part of the product? The whole experience around it, the manifesto, the website, the connection you build around it? It’s all part of the same thing. Maybe it is because the software is so complex that we see it as a separate thing, and also because it’s done typically by a different group of people within the company, that we start separating it. Or I don’t know.

Rob Walling: Yeah, no, I think you’re onto something. I think that most of us make that mistake, especially early on. It’s something that I think I did a decent job of, with Drip.

As soon as we built a product that I realized was killer and it was growing quickly, I did do these things that were talked about. I did reach out to my network and say, “Hey, we built something that I think is pretty special, you should take a look at it.” I really became an evangelist and worked my network to have people promote it, and did all that stuff.

But I did an okay job of it, I didn’t do a great job. And I feel like I’m finally, with this start-up, with Tiny Seed, that’s finally clicked in such a way. I don’t know if it’s because there is no software to write that it makes it easier for me. Or I don’t know if I’ve just matured and gotten better at it. But I’m definitely much more outward focused. I think that’s the difference. It’s like if you’re inwardly focused and you’re writing code in your basement, or your home office, you’re not going to have nearly as much of a chance of making it work.

Jeroen: Mm-hmm. Cool.

Totally different thing. Are you someone who works long days, or are you more of someone who creates a clear separation between “these are my working hours” and “these is my time”.

Rob Walling: Good question. My actual time of sitting in a chair behind a laptop is relatively small. Even when we were growing Drip, we tended to work about 35 hours a week. And I’ve always wanted that pretty decent lifestyle. With that said, if I was behind a computer 30-35 hours a week, I was thinking about it another 20 hours a week. Do you know what I mean?

Jeroen: Yeah.

Rob Walling: Even if I wasn’t writing something, it was constantly like, “Oh, you know what, I need to email that person. Boom, throw it in my Trello Board.” In the shower, or doing dishes, it’s like, “Oh yeah, that’s a really good idea for a blog post that would be viral. Boom hit up my Trello.” So my background thread and even my foreground thread is almost always about work and family. Those are the two things I think about most.

And so these days I’m similar. I can’t sit behind a computer for 8 or 10 hours a day anymore. I used to do that. Back in the early days when I was consulting full-time, working a day job, I would come home at night. We didn’t have kids, or we had a really young one, and I would then put in another three to four hours every night. I worked really long days, but it was a side hustle, right?

My goal was to get out of the day job. And I was younger, this was again 10-15 years ago. Then at a certain point, once I achieved, I’ll call it freedom, where I was living off my own product income, which was what about 10 years ago now that happened, I backed way off.

And I said all right, I’m going to work as little as possible, just to see if I can. I had about eight months where I worked about 10 hours a week in total. It was pure automation lifestyle businesses. And it was amazing, and then I got bored.

That’s when I said all right, now I’m going to do my next thing. That’s when I did HitTail, which was that SaaS app before Drip, and took on new challenges. So that’s been my evolution. It’s a long way of saying a little of both. But I do feel like I am so much more efficient than I used to be. I can sit down for four hours and get done what used to take me eight hours because I’m just, I don’t know, older, wiser, whatever it is.

Jeroen: Yep. How do you think you do that? Because people are filling the whole internet with productivity tips.

Rob Walling: Yeah. I mean, so I actually recorded an entire 20-minute episode of this podcast called Zen Founder. And it’s called Rob’s Productivity Hacks, or something like that. It went live within the last month.

I just talked through what I do today, and how I manage all of the incoming work. I get probably 150 emails a day, so I have at any given time, 20 emails in my inbox. I process email very fast now. And I use Trello and Gmail, and I’m trying to think of what are my other systems.

But I just, when stuff comes in, you triage it, you delete it, you respond quickly or you Top Pop it in Trello to respond later. I don’t double handle stuff. I capture everything and process it quickly.

So I think that’s been a big thing. To not leave stuff sitting somewhere where I keep coming back to it and thinking about it. And then, oh, I’m going to go check Twitter and Hacker News. And then you come back to it again. That’s been a discipline that I’ve had to teach myself because I don’t think any of us do that naturally.

Jeroen: So you use two apps next to each other, Gmail and the Trello app?

Rob Walling: Yep, and I have them all pinned. I have them pinned in Chrome. I use them right together. So if something comes in that’s any type of length, like hey I’m going to recruit a speaker for MicroConf, I email her, she sends me a video and it’s like I’m not going to do that right now. So I will pop it in Trello, “watch this video”. Boom, links in there.

And I know that at a certain point the next day I will be fried. Because at peak productivity time, I don’t want to be watching a video. At peak productivity time, I should be writing a manifesto, or I should be writing a difficult email, or I should be thinking through something very complicated.

But at a certain point, I’m going to be tired, I’m going to kick on that video then. I have a Chrome plugin that makes it so easy that I can watch videos at an accelerated speed. I watch it at about 1.6, 1.7X. Any embedded video it will do that, YouTube and Vimeo, and even stuff from Dropbox. If it’s HTML5 it will do it. And so then I’ll do that and skim through it. It’s the little things like that, but each of them adds up. I feel like I’m more productive than I used to be in a lot of ways.

Jeroen: Yeah, so if I gathered it well, you basically take the to do’s out of the emails. You put it into Trello.

Rob Walling: If they’re longer, yes. If it’s something I can do in a minute or two, I just do it right there in the email.

Jeroen: Are you using the snoozing functionality in Gmail?

Rob Walling: I do. Well, so I use Boomerang, which was a precursor and that’s another thing. I am like keyboard shortcut obsessed. I try to figure them all out. In Gmail, I almost never touch the mouse, if you watch me. I mean being a programmer, I learned that. It’s like I don’t ever want my hand to leave the keyboard.

So as emails are coming in and I’m going through them or if I’m sending an important email and I know I’m going to email an important person to ask them, “Did you want to invest? Or do you want to potentially be a founder in Tiny Seed? Or do you want to be a speaker at MicroConf?”, I know that I want a response. And I don’t want to have to remember that.

So the shortcut is you hit B and then you hit space in seven days, hit enter, and it will Boomerang it in seven days. If they respond it won’t Boomerang it. And if they do respond, or if they don’t respond then I’ll get it back. And then I can follow up on that.

Boomerang was life-changing for me. Life changing is maybe exaggerating, but it definitely changed my workflow over the last three to four years, from the time it came out.

Jeroen: Yep, but you’re still on Boomerang, not on the snoozing in Gmail?

Rob Walling: Yeah. I do snooze in Gmail when I’m on my phone because I use the Gmail app on IOS and it doesn’t have Boomerang built in. But now that snooze is there, I do. That’s the other thing, I went on vacation a couple weeks ago. I still check email every day when I’m on vacation, multiple times. And certain things I’ll respond, boom, no problem. And other things it’s like huh, I’m not going to do that until I get home. So I snooze it for the Monday or Tuesday after I get back because I just don’t want it cluttering my inbox. And that does mean that I get a bunch of stuff coming back in my inbox on a Monday or Tuesday after vacation. But typically by that time I’m well caffeinated.

I’m at a place on my laptop where I can handle all these things super fast. I don’t try to do long emails on my phone. I don’t try to do a lot on my phone, because it’s just such a hassle. You’re very inefficient typing on a phone.

Jeroen: Mm-hmm, that’s true. Are there any other things you do to stay productive?

Rob Walling: Yeah, I’m really mindful of my body clock. And I know that I have productivity, a nice big productivity spurt, in the morning for about three or four hours. Then I know afternoons are going to be less creative, but I can still get a lot done. I tend to do a lot of email in the afternoons. I tend to do my deep work in the morning. So I actually shut the Gmail tab. I have no notifications on anything. My phone doesn’t buzz. The only time my phone buzzes is if someone texts me, or if Instacart shows up at my door or whatever. It’s important, and not many people have my phone number. So emails don’t make my phone buzz, and neither do Twitter DMs, and neither does LinkedIn DMs or any of this stuff. All that is batched at a separate time.

Jeroen: Right.

Rob Walling: And so I guard the morning. Typically drink a very small amount of caffeine, and I put on headphones and turn on some type of either deeply focused playlist, or often punk music, like really fast, hard-hitting music. And it kind of motivates me. I’ll just crank through a bunch of stuff. And that’s been a fun one too, just to be able to control the times of day that I work and do what kinds of work, and to not book meetings in the morning. This is all luxury of running your own company.

Whereas if you’re working for someone else, it’s not necessarily that you can block out your whole morning every morning and not have to meet with other folks. So I feel like I’m at peak productivity when I’m able to manage my own schedule.

Jeroen: Wow, that’s cool. Slowly starting to wrap up, because we’ve been talking for quite a while already. What is the latest good book you’ve read, and why did you choose to read it?

Rob Walling: That’s a good question. Latest good book, dang that’s a tricky one because I was going to talk about a book that I just like in general.

Jeroen: No, it’s good, good.

Rob Walling: You’re okay with that?

Jeroen: Yeah, whatever you feel strongest about.

Rob Walling: Okay. I really liked the book The Snowball, and it’s the biography of Warren Buffett. And the reason I liked it is that I love the story of someone who is just really good at something for a very, very long time. He came from modest means and he built himself up from nothing into a billionaire. And he didn’t do it in a fancy way. He did it by showing up every day, and by being really pragmatic and just playing long ball. He thinks longer term than pretty much anyone, you know? And over decades his money has just been compounding. So it’s a fascinating story to see someone build an empire like that out of nothing. And he didn’t build a company per se. Obviously, he buys and acquires companies and all that, but he didn’t do a Jeff Bezos. He didn’t start Amazon, he didn’t start GE. And that’s how a lot of people get rich. He did it in such a different way, and the story is amazing. It’s one of my favorite audiobooks of all time, actually.

Jeroen: You don’t read, but list to audiobooks?

Rob Walling: I listen to a lot of audio, yeah. I subscribe to maybe 40 podcasts, and I probably listen to an audiobook a week, maybe two.

Jeroen: Another question, is there anything you wish you had known when you started out?

Rob Walling: Yeah, I mean two things. One, I wish I had known that it’d take a lot longer than I thought it would. I figured that as soon as I had some success. The problem is you read the press. Now it’s TechCrunch, but it used to be Entrepreneur Magazine and Inc Magazine before. I know they’re still around, but the stories are always glorifying this overnight success. And I just don’t believe in overnight success anymore. It was a painful realization that “oh, it’s going to take me years to achieve my goal”. I wish I’d known that at the start. I think that’s a big one.

I think the other one is that the emotional side in being able to manage your own emotions as an entrepreneur is way more important to you than perhaps any other skill.

Jeroen: Yep. That’s indeed a piece of very good advice. What is actually the best piece of advice you’ve ever got? If you can share that with us.

Rob Walling: Hmm. It wasn’t advice given directly to me. It was a blog post that Jason Cohen wrote. And he called it Rich or King, and he basically says, “Look, do you want to be rich, or do you want to be king?” The context is you’ve had an offer from someone to acquire your company. And some people say, “I would never sell my company ever, ever, ever, and I want to be king of this company. I want to run it till the day I die.” And other people say, “I want the liquidity, and I want to have enough money that I can fund all of my kid’s college savings accounts, and that I never have to worry about money for the rest of my life.” There’s rich, and then there’s king.

And in it, he’s defending his decision to sell his startup. He’s sold multiple startups. He basically says it’s easy to say, “Oh, I’d never sell my startup,” until you’re sitting in a restaurant and someone offers you enough money that you never have to work again. That’s when the rubber meets the road. Am I going to do this or not? And he talks through both sides of it, and basically says look, if it’s your first one and you don’t have enough money to live forever, F.U. money some people call it; if you don’t have F.U. money, then it’s probably a decent idea to do that and take some money off the table. I think that certain people get caught up in the dogma, or the pride, of never selling ever. And I don’t know if that’s the right choice. I feel good about the choices I’ve made in terms of moving from one company to the next. And I think that post probably helped me make those decisions.

Jeroen: Awesome. Thank you. Thank you again, Rob, for being on Founder Coffee. It was really great to have you.

Rob Walling: Yeah, man. It was great. It was my pleasure, and I appreciate you inviting me on.