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Episode 20: Interview with Rob Walling, Founder of Drip + MicroConf

Rob Walling is the Founder of Drip, an email automation platform.

A serial entrepreneur who has published books, runs MicroConf, and hosts a podcast, Rob shares the importance of deliberate hiring, and focusing on trust instead of loyalty in teams.

Claire: Hey everyone, I’m Claire Lew, and I’m the CEO of Know Your Company, and today I have a really special guest. I have Rob Walling, who is the co-founder of Drip, an email marketing automation software. Actually, I don’t know if you know this, Rob, we actually use Drip, your company. We love it.

Rob: You know, I didn’t. Awesome. That’s great to hear.

Claire: Yeah, and it’s actually, it’s only one of many things, or ways, that Rob and I are connected. Rob is a serial entrepreneur. He started multiple companies in the past, he speaks at a ton of conferences, he runs a conference called MicroConfwhich I actually happen to speak at, so just been a big admirer of your work over the years Rob. Everything you’ve built. And I know recently you’ve and your wife Sherryactually just published a book-

Rob: That’s right.

Claire: … which I highly recommend for people to check out. Just by the title. I believe it’s The Entrepreneur’s Guide to Keeping Your Shit Together. So I think-

Rob: That’s exactly right.

Claire: I think we could all probably read a page or two out of that just based off the title. But yeah, an honor to have you here today Rob. Thanks for joining us.

Rob: It is my pleasure. Thank you.

Claire: Cool. Well, so Rob, I’ve been asking all sorts of folks this past year this one question about leadership, and what it is, is “What’s something you wish you would have learned earlier as a leader?”

Rob: Yeah, it’s a great question. I’ll have to go back and listen to all the prior answers. I did not on purpose so that I wouldn’t accidentally say someone else’s.

I wish that I had learned that I didn’t need all the answers. I don’t need all the answers as a leader, and that hiring people that are better than I am at something, and then when a problem comes up looking around the room and saying “I don’t know. What do you think?”

You know, and it’s not always that. It’s not always putting it back on everybody else, but for me leading 15 years ago when I first started in my 20s, I was all nervous like “I have to be the boss and I have to know the answers and when people come to me I have to be able to say ‘Well this is what we should do.’” And over time realized “No, I work with really smart people,” especially if I’m hiring well, and my most recent experience with that is at Drip, and it’s the best team I’ve ever assembled, it’s the best team I’ve ever worked with. And now when problems come up, it is always a look around the room and saying “Someone here knows this answer. It may be me, but it’s most likely going to be one of you.” And that’s … I wished I had known that a lot sooner.

Claire: Wow. Yeah. I can totally relate. Oh my goodness. I think there’s something almost inherent in how our culture even thinks about leadership, right? That leaders know the answers. That’s the whole point. And so I love that realization. I also think something really interesting that you just talked about is how you feel like Drip, the current company that you founded, is your best team assembled to date, right? So tell me about, was it something different you then did in the hiring process or in thinking through as you’re coaching people? Why is it different? And in what was is this idea that you don’t have to be the one knowing all the answers? What role did that play in so that … you know, that’s a bold statement. “The best team to date I’ve ever assembled.” So I want to hear more about that.

Rob: Yeah. Yeah sure. I mean, there’s a couple reasons that I say that, or that I was able to build that team. I say it because it’s true, and I enjoy my work so much more working with these folks, and they’re the … whatever scale, if you were to say one to ten as developers, one to ten as co-workers, one to ten as whatever, just across the board the folks I work with now are better. And I’ve worked with great people. I’ve been coding, essentially, for 20 years, almost — coding and founding software companies for almost 20 years.

The reason I was able to do it differently this time was a couple things. One, I had full control. Like, I built it from square one. I was employee number one. Derek my co-founder. Number two, there was no one kind of foisted on me. The other thing is, since Drip did grow very quickly, I had budget to hire at a level that I used to not be able to. I used to hire a lot of contractors. I needed cheap talent because if one of my apps was making 20 grand a month, it’s like you can only hire someone so good and still pay the bills, you know? But Drip had the growth and the revenue to cover it. And the third thing is, I had the luxury. Well, there’s four things. I’m going to keep going.

Claire: Keep going. Keep going.

Rob: The third was my network was the biggest it’s every been. You know, as you said I have a conference now and I have all this history, and the blog, and the podcast and just all this stuff that I’ve done, that it enabled me to kind of have a reputation to draw people.

But the fourth reason that I think is perhaps of all those, one of the most important, is we hired slowly and we were very picky. We turned down dozens of candidates for every person that we have wound up bringing on.

And so it has meant at times we don’t hire as fast as I would have liked, and as a result sometimes the road map isn’t moving as fast as I would have liked, but it was a long term view. You know, I’ve been working on Drip for five years now. It is a long term view of, in the end five years from now this team will be phenomenal if we just slow it down a little bit, versus making that snap decision. “Well, no, just say yes to this person,” and then you’re a year down the line like “Oh my God, I’ve built a toxic culture,” or “Now I have to fire two people because they’re not working out.”

Claire: Absolutely. I think that’s tremendous advice. Almost so much more difficult to practice, than it is talking about. Because I know the temptation, especially for folks who are funded or who have the luxury of being able to spend cash up front pretty easily to hire folks. Yeah, you can’t move as fast if you don’t have the right people, so that temptation is definitely there.

What sort of checks or questions or processes did you put in place, or how did you think about consciously? It sounds like a very conscious decision of “I’m going to slow down this hiring process and we’re going to wait it out.” How do you make that call? How do you decide when that? Especially as you start off as a self funded company, right? You don’t have that luxury. You have competitors who are funded. I mean, how do you grapple with that as a founder, as a leader?

Rob: You know, I didn’t make the deliberate decision to slow it down as much as I made the deliberate decision to hire very carefully, which by its nature the result is that it does slow down. So I wish we could hire faster, but the checks as you were saying, is we have a few layers of interviews, and that first interview is all about personality, and it’s all about probing into things and catching: What are the yellow flags and what are the red flags?

If we talk to someone with no yellow flags, I’m suspicious, like we didn’t get their true self. Because if I was in an interview, you would pick up on things, and it’s like “Yeah, Rob’s really good at this, and Rob’s going to kind of be a pain in the ass about that. Rob’s not going to be great at this.” You’re just going to know. No one is infallible, and so if I don’t pick up on at least a couple, a yellow flag or two, we actually dig further. And then you just start seeing patterns.

I’ve done hundreds, literally hundreds and hundreds of interviews over the course of the 20 years of hiring developers and product people. And so I think at a certain point its trusting gut. But also we have four or five different people who talk to the candidate over the course of a couple weeks, and we do pair programming now which has been a real game changer for us. A one hour pair programming interview to look at not just the technical. It’s not “Oh, do they know the right words?” It’s like “How are they to sit next to for one hour and code with? How does that feel?” I think we really upped our game there.

And as usual, it’s, “If in doubt it’s probably a no.”

Claire: Hmm. Yeah. I think that’s so wise.

I want to go back, Rob, to the original statement you made as the answer to the question about letting go of having to be the person with the answers. Talk to me about the time prior to that revelation when you felt like you needed to know the answers. I mean, what was the cost of that? Was there some event or something that happened or a conversation that you had where it caused you to realize “Oh gosh, the whole point of having a team I guess is for me to not know everything,” or … I’m very curious about that.

Rob: What caused that mindset shift.

Claire: Right. What caused it, or if there were any … if you got burned because of it at any moment.

Rob: The cost of it was that it was a mental cost, right? It was having the burden of constantly having to go from a manager’s point of view or a CEO point of view where you’re kind of at 10,000 feet and then someone comes with something, and it’s like “Alright, I need to dig in and actually look at this code and make a decision,” right? And it’s like “Huh, this is taxing mentally,” because you only have so much good glucose in a day that you can use for interesting things or decision fatigue sets in.

So that was probably the biggest cost for me, is I just could only make so many decisions, and I was making too many I should not have.

And the tipping point was two things. One, it was eventually realizing that was just stupid, and then two it was starting to work with better people. And Derek was … was Derek the first? There was a support guy before that named Andy who took everything off my plate and I started realizing “Wait a minute, this is very interesting.”

At a certain point he’s really good, fully remote, and I’d never met him in person. We’ve worked together for eight years or whatever. He started saying “Hey, I think I’m just going to make some decisions about some stuff that I’m checking in with you.” And I was like “Fine. Do it.” And I would look back and be like, he made 20 decisions last month that prior I would have asked him to run by me, and one of them was wrong in my book, or it didn’t live up to what I would have done. The cost of that one decision compared to the 19 I didn’t have to make was just so over. It was such an offset that I was like, “This is a no brainer. I need to find more people like him, and I need to do this again.” You know?

And then finding my co-founder Derek, co-founder of Drip, pretty quickly we talked through what the original incarnation of Drip would be on my kitchen table, and then I said “All right, you let me know when you have something to show me.” It was like six or eight weeks later, he comes back, which is … I never did with developers, right? He was a contractor at the time and eventually became my co-founder. I would never do that because it was always like “Send me weekly updates with this, and the screenshot and then I can tweak the this and then copy it,” you know. And he came back after six or eight weeks and I was like “Damn, that’s really good. Let’s tweak these two things.” And it was like “Huh.” Working with someone of his caliber really makes this a lot easier, and during that time I was able to focus on marketing and all this other stuff, and so those were kind of the events that led me to that.

Claire: Absolutely. I think something that what you’re talking about, one thought that it evokes is, I talk with so many emerging managers, right? So, new managers, first time managers, who find and struggle with that decision point of, how much do I trust? How much do I let go? I don’t know if I’m going to see the caliber of the work that’s there. I mean, what advice would you have for folks in that situation who feel like they’re not sure if they’re ready to give that space? What would you say to that?

Rob: Yeah. I think that “trust but verify” is kind of what I start with, with people. So basically trust them to make the right call and see if they did, and over time you will learn to trust them more, and if they’re doing well, and if they’re not, then they’re probably not right for the role. I think that’s a big thing, right? It’s the kind of fire fast type thing, and in our world of start ups, when every person counts and you have a team of five or a team of seven, everyone needs to be high achieving.

And so I think when a new person would start, it was a slow, kind of a slow trust building in both directions to be honest, and coming back to your original question about leadership, that’s probably the one thing … you didn’t ask this.

But if I were to think, what is the one thing as a leader that is my job to do, and it’s instill trust in both directions. That’s what I strive for. And that ultimately leads to loyalty. I used to say it’s instill loyalty, but I realize trust comes first.

Claire: Talk to me about the difference. I’m so curious. I’m with you. I want to hear more.

Rob: Trust is just a matter of like, from my perspective as a leader, it’s like “I’m going to give you stuff or I’m going to help you figure out what to do, and I’m going to trust that you’re going to do the best you can and you’re going to come to me when you have questions, and you’re going to deliver a good product.” Trust in the other direction, to me, from my colleague, I believe is that I have your back in every situation. That when a customer screams at you on the phone, that that customer … I either have a conversation or I fire the customer, that I do not let my people get abused. And I’ve done that many times. Email and all that kind of stuff.

That I have your back when the database goes down on a weekday, I don’t just push the developer or the DBA to do it, that I’m actually sitting there as well trying to figure stuff out. That doesn’t scale when you’re at 50 people, but when you’re at five, yes. You trust that I essentially have your back, and over time. So trust is something that you can develop by showing up and by doing what I was talking about. And then I think loyalty develops with trust over time, and loyalty becomes less of “I know you’re going to be there,” and more of “I want to have your back as well,” if that makes sense.

It’s a mutual feeling of “I’m willing to take a …” either of us are willing to take a figurative bullet in business to be able to support you. And that may mean “Boy, I’m going to work this weekend even though you didn’t ask,” or “I’m going to work this weekend and not resent it because you did ask and I know that you don’t do this often, and I know that you need this,” or whatever it is. You know, we didn’t work a lot of weekends, but those are examples, right? It’s like “I’m willing to go the extra mile for you both as the founder and as the person, the developer or the customer success person.”

Claire: Absolutely. Yeah, no, I love that you emphasize that. It’s one of the main roles of the leader to instill trust, because I couldn’t agree more in many ways. Trust, it’s the oil of the machine, right? Nothing functions without that sense of trust, and you’ve got my back, I’ve got yours. And that when you argue we have our best intentions in mind. I’m not trying to screw you over, I’m not trying to take credit for something, and I think as a leader, again, our mental models around what leadership is, is about decisions, it’s about vision, it’s about charisma. Trust doesn’t get brought up very often, so I really appreciate you sharing that.

Rob: Yup. For sure.

Claire: Well hey Rob, thank you so much again for your time today. It’s been a blast to get to talk to you.

Rob: Absolutely. I enjoyed it.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.