
Rob Walling is the Founder of Drip, an email automation platform.
A serial entrepreneur who has published
Claire: Hey everyone, Iām Claire Lew, and Iām 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 donāt know if you know this, Rob, we actually use Drip, your company. We love it.
Rob: You know, I didnāt. Awesome. Thatās great to hear.
Claire: Yeah, and itās actually, itās 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 youāve built. And I know recently youāve and your wife Sherryactually just published a book-
Rob: Thatās right.
Claire: ⦠which I highly recommend for people to check out. Just by the title. I believe itās The Entrepreneurās Guide to Keeping Your Shit Together. So I think-
Rob: Thatās 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, Iāve been asking all sorts of folks this past year this one question about leadership, and what it is, is āWhatās something you wish you would have learned earlier as a leader?ā

Rob: Yeah, itās a great question. Iāll have to go back and listen to all the prior answers. I did not on purpose so that I wouldnāt accidentally say someone elseās.
I wish that I had learned that I didnāt need all the answers. I donāt 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 āI donāt know. What do you think?ā
You know, and itās not always that. Itās 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 āI 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 āWell this is what we should do.āā And over time realized āNo, I work with really smart people,ā especially if Iām hiring well, and my most recent experience with that is at Drip, and itās the best team Iāve ever assembled, itās the best team Iāve ever worked with. And now when problems come up, it is always a look around the room and saying āSomeone here knows this answer. It may be me, but itās most likely going to be one of you.ā And thatās ⦠I wished I had known that a lot sooner.
Claire: Wow. Yeah. I can totally relate. Oh my goodness. I think thereās something almost inherent in how our culture even thinks about leadership, right? That leaders know the answers. Thatās 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 youāre coaching people? Why is it different? And in what was is this idea that you donāt have to be the one knowing all the answers? What role did that play in so that ⦠you know, thatās a bold statement. āThe best team to date Iāve ever assembled.ā So I want to hear more about that.
Rob: Yeah. Yeah sure. I mean, thereās a couple reasons that I say that, or that I was able to build that team. I say it because itās true, and I enjoy my work so much more working with these folks, and theyāre 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 Iāve worked with great people. Iāve been coding, essentially, for 20 years, almostāāācoding 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, itās 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, thereās four things. Iām going to keep going.
Claire: Keep going. Keep going.
Rob: The third was my network was the biggest itās 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 Iāve 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 donāt hire as fast as I would have liked, and as a result sometimes the road map isnāt moving as fast as I would have liked, but it was a long term view. You know, Iāve 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. āWell, no, just say yes to this person,ā and then youāre a year down the line like āOh my God, Iāve built a toxic culture,ā or āNow I have to fire two people because theyāre not working out.ā
Claire: Absolutely. I think thatās 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 canāt move as fast if you donāt 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 āIām going to slow down this hiring process and weāre going to wait it out.ā How do you make that call? How do you decide when that? Especially as you start off as a self funded company, right? You donāt 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 didnāt 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 itās 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, Iām suspicious, like we didnāt get their true self. Because if I was in an interview, you would pick up on things, and itās like āYeah, Robās really good at this, and Robās going to kind of be a pain in the ass about that. Robās not going to be great at this.ā Youāre just going to know. No one is infallible, and so if I donāt pick up on at least a couple, a yellow flag or two, we actually dig further. And then you just start seeing patterns.
Iāve 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. Itās not āOh, do they know the right words?ā Itās like āHow are they to sit next to for one hour and code with? How does that feel?ā I think we really upped our game there.
And as usual, itās, āIf in doubt itās probably a no.ā
Claire: Hmm. Yeah. I think thatās 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 āOh gosh, the whole point of having a team I guess is for me to not know everything,ā or ⦠Iām 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 managerās point of view or a CEO point of view where youāre kind of at 10,000 feet and then someone comes with something, and itās like āAlright, I need to dig in and actually look at this code and make a decision,ā right? And itās like āHuh, this is taxing mentally,ā 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 āWait a minute, this is very interesting.ā
At a certain point heās really good, fully remote, and Iād never met him in person. Weāve worked together for eight years or whatever. He started saying āHey, I think Iām just going to make some decisions about some stuff that Iām checking in with you.ā And I was like āFine. Do it.ā 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 didnāt live up to what I would have done. The cost of that one decision compared to the 19 I didnāt have to make was just so over. It was such an offset that I was like, āThis is a no brainer. I need to find more people like him, and I need to do this again.ā 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 āAll right, you let me know when you have something to show me.ā 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 āSend me weekly updates with this, and the screenshot and then I can tweak the this and then copy it,ā you know. And he came back after six or eight weeks and I was like āDamn, thatās really good. Letās tweak these two things.ā And it was like āHuh.ā 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 youāre 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 donāt know if Iām going to see the caliber of the work thatās there. I mean, what advice would you have for folks in that situation who feel like theyāre not sure if theyāre ready to give that space? What would you say to that?

Rob: Yeah. I think that ātrust but verifyā 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 theyāre doing well, and if theyāre not, then theyāre probably not right for the role. I think thatās a big thing, right? Itās 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, thatās probably the one thing ⦠you didnāt ask this.
But if I were to think, what is the one thing as a leader that is my job to do, and itās instill trust in both directions. Thatās what I strive for. And that ultimately leads to loyalty. I used to say itās instill loyalty, but I realize trust comes first.
Claire: Talk to me about the difference. Iām so curious. Iām with you. I want to hear more.
Rob: Trust is just a matter of like, from my perspective as a leader, itās like āIām going to give you stuff or Iām going to help you figure out what to do, and Iām going to trust that youāre going to do the best you can and youāre going to come to me when you have questions, and youāre going to deliver a good product.ā 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 Iāve 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 donāt just push the developer or the DBA to do it, that Iām actually sitting there as well trying to figure stuff out. That doesnāt scale when youāre at 50 people, but when youāre 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 āI know youāre going to be there,ā and more of āI want to have your back as well,ā if that makes sense.
Itās a mutual feeling of āIām willing to take a ā¦ā either of us are willing to take a figurative bullet in business to be able to support you. And that may mean āBoy, Iām going to work this weekend even though you didnāt ask,ā or āIām going to work this weekend and not resent it because you did ask and I know that you donāt do this often, and I know that you need this,ā or whatever it is. You know, we didnāt work a lot of weekends, but those are examples, right? Itās like āIām willing to go the extra mile for you both as the founder and as the person, the developer or the customer success person.ā
Claire: Absolutely. Yeah, no, I love that you emphasize that. Itās one of the main roles of the leader to instill trust, because I couldnāt agree more in many ways. Trust, itās the oil of the machine, right? Nothing functions without that sense of trust, and youāve got my back, Iāve got yours. And that when you argue we have our best intentions in mind. Iām not trying to screw you over, Iām not trying to take credit for something, and I think as a leader, again, our mental models around what leadership is, is about decisions, itās about vision, itās about charisma. Trust doesnāt 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. Itās been a blast to get to talk to you.
Rob: Absolutely. I enjoyed it.
