Jeff Robbins is an actual rockstar

[01:46] Where do I even begin to introduce Jeff Robbins? You see, Jeff has had a few different successful careers in a time that most of us get around to one. He worked on the web before there was a web. He started a company that’s built some of the most famous websites, and as if that weren’t enough, he was in a band in the ‘90s that signed with A&M Records, toured the U.S. and Canada and played at some of the coolest events. So where exactly does Jeff’s story begin? In a magical place called the ’80s.

[laughs] Okay, let’s go into the way-back machine, Tim. Man, I mean, I’ve been interested in computers and that kind of stuff for a long time, and I’m old, so it goes way back… In the ‘80s my dad bought a IBM PC Junior, which was like the cheaper one that people could afford for their house, and I started learning basic programming on that, and then I – yeah, I did all kinds of stuff… I had a Hewlett Packard programmable calculator that I’d won in the State Math Fair – or the Science Fair… In my town it was the Math Fair, and then we went to the State Science Fair… And I won this calculator and I programmed it to play Monopoly… So you know, I’m a nerd going waay back to the ’80s.

Then I bought an Atari ST computer that had MIDI ports on it, so I could hook it up to my synthesizers and drum machines, and stuff like that… And I remember I worked all summer to save up the $1,200 or whatever it was that the Atari cost… And then I realized if I got a modem, I could connect to these bulletin board systems, and talk to people, and find out information, and stuff. So I did that with the various bauds of modems over the years, and I eventually realized that I could make some money with my computer skills. [laughter]

I started doing temp work on Macs, and learned desktop publishing, and eventually learned FreeHand, which was kind of a precursor to what we now call Illustrator, and ended up getting a job at O’Reilly, doing technical illustrations for their books… And they were connected to the internet, which was really cool! I could FTP out to things, and there was a thing called Gopher, which was a precursor to the web, and I could connect to these free software - actually free software, not pirated software - open source software boards and download software, and it was so much faster than doing it over my modem…

[04:17] Then the web started, and O’Reilly being kind of at a crossroads of that stuff, writing books about TCP/IP – they had a book about Gopher, and FTP, and all that kind of stuff… The people at CERN, who were developing the HTTP protocol, and HTML - they came to Cambridge, came to the office in Cambridge where I was working, and kind of did this pitch, like “Hey, you all need to get into the web. The web is gonna be the big thing. We want this to be the big thing, and O’Reilly should write books about it.”

Tim O’Reilly and Dale Dougherty being the visionaries that they are, said “Well, we’re gonna do more than that… We’ll create an online magazine and use our publishing skills to do web stuff.” So they started creating the Global Network Navigator, GNN.com, and I was involved in a lot of the brainstorming of that, and the woman who would eventually become my wife was the designer… So my wife is the first commercial web designer, and I got so excited that before GNN even launched I started one of the world’s first web development companies in 1993. It was an uphill battle, because no one had heard of the web. [laughter] No one wanted a website, because they didn’t know what it was.

They would say things like “Oh, I got burned! We’ve spent all this money on a CompuServe page. We invested all this money in Prodigy, and now Prodigy is shutting down! How is the web gonna be better than that?”, so I would have to do sales pitches that were like that.

Then about a year later my band got caught up in a – all record labels were very excited about it, we got caught up in a bidding war, and I said goodbye to web stuff and spent the rest of the ’90s in a van, driving around the country. [laughs]

Wow…

We eventually played Lollapalooza and all sorts of radio festivals, and I got to see most of the places in the United States and Canada, and a few places in Europe, and all that kind of stuff. A lot of my web friends went on to found what are now very big empires, kind of… [laughs] But I was their cool guy who they met through web stuff, who was in a bad, and the band was touring around and playing Lollapalooza, and stuff… And for me, they were like “Oh, I know the guy that started Flickr, and Blogger, and Twitter, and Slack”, and things like that…

So what did you do with your company when you decided to tour with the band?

I handed it over to my business partner.

Was that a difficult decision for you?

I got offered a record deal, Tim! In 1994! It was like “Rock ’n roll!” No, it was not a difficult decision. [laughter]

I figured that’d be the answer, but I wanted to ask, just in case.

You know, I also started doing web stuff for the band; we created the first record label website for the little independent record label that we were running on the side. My band was one of the first bands to have a website… Then we got signed A&M records and I was in there, talking to them about “Oh, what are you guys doing with this whole web thing?” and they kind of looked at me like “Well, if there are any conferences that you wanna go to and you could speak on behalf of A&M…”

So for a couple years, before they kind of got going with it, I was sort of like the de facto web guy for A&M Records while I was in one of the bands on their label, and stuff like that… So I kept my hand in.

What brought you back to the web?

Well, in about 2001 there were a whole bunch of record label mergers. In the ’90s there were nine major record labels, and over the course of about a year and a half, that number went to three. So basically, they just all sort of collapsed in on each other.

And, you know, Our first album had done well, but basically A&M came back to us and said “Hey, we think you’ve got momentum here. Rather than squeezing everything we can out of this album, why don’t you go and do another album?” However, when the accountants came pummeling through, trying to decide which bands to keep and which to leave while these labels were merging, we just hadn’t sold enough records, so we lost our record deal.

We kind of fumbled on for a while, we put out some stuff independently, we went back to that record label that we’d started back in 1991-1992… It was a few years before the label money dried up, but I put out my shingle and started doing freelance stuff. I got a job in an ad agency. Through a series of circumstances and coincidences, my wife and I ran Ringo Starr’s website for about three years, and that sort of led to bigger and other projects for sort of celebrity-type people, and kind of bigger and bigger web projects, which eventually led me to Drupal.

In trying to build a really big and difficult Drupal website I met Matt Westgate, who was just a guy doing work in the Drupal community. I met him on a message board, because he was the most friendly person, answering my questions - all of my really kind of beginnery questions… He was super-friendly and I said, “Can I get on the phone with you? Can I just ask you these questions? I would pay you. I’ve run the math, and if I could pay you to answer these Drupal questions for me, then it would save me time and it would be well worth it for me to pay out of my own pocket.

So I did that, and the whole time I’m saying “This is so great! You really know this stuff. You can’t find this information anywhere!”

As the project was starting to wrap up, I kept saying to him, “We’ve gotta do something. I’ve gotta pay you back more than just the money I’m paying you. Let’s start a company where you can explain to people how to use people, and how to start a company, and how to promote things”, and that’s what became Lullabot. Lullabot started in 2006, and it was still really early days; with Drupal there weren’t any books out about it or anything like that… So the Lullabot people authored some of the first – well, Matt authored some of the first Drupal books, and we started the first Drupal-related podcast, and did the first Drupal trainings, and built a lot of the kind of first Drupal websites that people had heard of.

We launched on January 1st, 2006, mostly to just make it easy to remember… [laughs] and by March I have pictures of us sitting in a pub in London, where we were starting work on the MTV.uk website, which was kind of the first website… Because previous to that, it was like “Oh, the University of Calgary has built this website! It was really cool!”, but it wasn’t, like, MTV… So from there we did all kinds of stuff.

Think back to 2006 - to you, what was the scariest thing of starting a company?

[laughs] I don’t know… So about a year prior to that, maybe a little over a year prior to that. I had a job at an ad agency, and my wife and I were running Ringo Starr’s website, and the people at the ad agency kind of thought that was cool, and a little bit like “Why are you here, at this little Providence ad agency, when you’re doing all these things out there?” But my wife was pregnant, we’d just bought a new house, and I walked into my manager’s office to ask for more time off; I was out of my vacation days, but there was another web conference I wanted to go to, and I thought it was “Fine, just don’t pay me…” He turned to me and said, “What are you doing here? Why are you working here? You could be doing other things, you know that, right?” I said, “Yeah, I know. I guess so.” He said, “Go do other things!” I said, “Uh, okay, alright…”

Okay, alright, and so I left there, I left that job, and as I was driving home, I was thinking, “Wait a minute, did I just quit, or was I fired? I just bought a house, I’ve got a mortgage”, and my son was born three months later… So jumping off into the abyss is kind of my skill. [laughter] So I’m not saying it’s not scary, I’m saying that perhaps my skill is just not being able to estimate how scary it will be. [laughs]

Right.

So was Lullabot scary? No, not at all. It seemed like the next thing to do, and we had a whole lot of success early on. The fact that we got MTV within three months of starting was key; it felt like “Oh, it’s a positive feedback mechanism.” But you know, as we started to hire people, there were definitely fearful points… “Why am I doing this?” And it was the same thing with the band, or anything… It’s like “Why am I doing this?” The answer is “Because at one point I thought it would be really cool!” [laughter] I was like, “Oh, that would be cool!” “Why did I do that?”

The metaphor I always use is like “It would be really cool to swim across this lake”, and about halfway swimming across the lake it’s like “What the F…? Why did I do this?! This is crazy! I have no idea how I’m gonna get across this lake!” Then you get to the other side and all these people come up and go like “Wow, it is so great! Wow, how did you– I don’t know how you did that! That’s so great!” It’s like, “Because I was gonna drown otherwise.” [laughs]

There’s some lessons in there somewhere for somebody, I’m sure… But yeah, that’s how I work.

When and Jeff and Matt Westgate started Lullabot in 2006, they decided that it would be a distributed company from day one.

I’ve always thought it was such a brave decision, but Jeff describes it more as a happy accident.

In itself, it was a little bit of a leap of faith, that missing part of my brain… But it worked really well. And even just sort of because it was an experiment, it allowed everything to be more agile and thoughtful, like “I don’t know, how should we talk to each other? How should we keep in touch? How should we communicate?”

You know, when you have these barriers where you’re not all coming into an office and kind of falling into these legacy systems and processes of like “Oh, of course, I know what it means to work in an office and commute for an hour each direction. I know how that works.” But this - none of us knew how it worked, so it was really great to kind of figure it out as we went… But as we figured it out, it was like “This is great! I wanna share this with other people”, and having worked at O’Reilly Media in the early ‘90s, and being a friend with Tim O’Reilly… Tim has a saying that everyone has a book in them. “What’s your book?”

My wife has written several books about web design, and continues to do that… So I thought like “I wanna share this, but I don’t quite feel like I can speak on behalf of a community of companies that are doing this. I could just talk about Lullabot did, but I don’t know if that will help anyone, because it’s kind of built into the company’s DNA and I kind of wanna get a good cross-section of what’s going on”, and I think that for companies to talk to each other would generally be good… So I had this idea to do a conference, but sort of a discussion – what I call a roundtable discussion conference. We decided to call it Yonder, and we invited people that were running distributed companies, remote teams, company leaders and managers, to just kind of sit around in a room together and ask questions, share ideas, and have a discussion. That’s how Yonder got started.

As I started to make my way out of Lullabot, I took the brand along with me and started doing a podcast, and I eventually hired some people to do content, and we have an active newsletter now… Yonder.io is where people should go to find out more about Yonder, and get on the mailing list and listen to the podcast if you’re a podcast person; if you’re listening to this podcast, you probably are a podcast person.

There’s a fair amount of resources out there that are sort of aimed at remote workers, or digital nomads… But my fear is that that discussion is a little bit of an echo chamber and it doesn’t actually expand the job market. It doesn’t create more jobs for those people. So my focus has been trying to talk to companies, and about companies, and how companies hire and manager and run remote teams.

I think remote workers will find it interesting, this idea of managing up… For the workers to understand what good management looks like; they can kind of nudge their managers in the right direction, like “Hey, have you heard this podcast…?” and ultimately kind of create a better work environment. My mission with Yonder is to really expand that market.

It’s happening slowly… The people, the companies that are doing remote work - there’s so much excitement and elation around how good it is that it’s easy to kind of think that everyone must understand that… But really, in that world of Fortune 500 companies, we’re just not there yet; those companies are not champing at the bit to make remote work work… But I think we’re gonna hit the tipping point in the next few years, and the podcast is going to become very popular. It’s already pretty popular, but…

[20:23] I like the description that remote work is the future of work. I really do think that the companies that have latched onto this idea have only benefitted, because they have this amazing pool of people that they can hire from, that isn’t tied to any particular location.

I think a lot of the times you find people who are really great workers, who are kind of devoid of the, as I like to say, “ass in seat” mentality, where as long as I’m here for eight hours, I did what I was supposed to do, rather than – I feel like the remote work whole idea is to be productive in the moments that you’re in front of your desk.

Yeah. I mean, remote work is autonomy. The idea of autonomy is not an add-on to work when you’re doing remote work. You can work at McDonald’s and you’re not going to have any autonomy. You could work at Starbucks, and like “Oh, there’s a little bit more culture, and they give us a little bit more choice… I have some autonomy, this feels great!” If you’re doing remote work, people can’t look over your shoulder. There are certainly companies that are developing tools for this sort of Big Brother shoulder looking over, but you’re kind of fighting against nature a little bit there.

Then there are some prerequisites for allowing some autonomy, which is trust, respect… You mentioned this, but to sort of expand on it a little bit - one of the reasons that companies who are hiring remote workers can get such great talent is because there are so many people that want to work remotely, and not only are you choosing from a larger talent pool, kind of by definition you’re offering a better job… Because it’s more flexible, and it offers probably autonomy, trust and respect along with it, right?

Hopefully, yeah.

Hopefully. You know, companies have all sorts of different cultures, and even distributed companies have all sorts of different cultures. But this means like – most of the companies I talk to… I was just talking to Addison Berry, who runs Drupalize.Me, which was a spin-off company from Lullabot, that does Drupal training online… And she was saying they were hiring a customer support person. She said that they got – I think it was like 3,000 applications in four or five days. It was an incredible amount… So from that – now you’re just playing numbers. This is just statistics. How many of those people are good? How many of those people are great? How many of those people are better than you could imagine? Just sift through them and find the ones that are better than you can imagine and then hire them. Now you’ve got people working at your company that are better than you could imagine.

So it’s been a few years now that you’ve left Lullabot. What led up to that decision?

Well, I’m a starter, I’m a big thinker… I like solving really difficult problems and I like making things that are kind of indistinct more distinct, things that are confusing more clear… That comes into things like branding, and kind of building culture, and all that kind of stuff…

I also really like working with really great, talented people. Over the years, with Lullabot, there were a lot of big problems to solve… “Who are we? How do we talk about ourselves? What do we do? How do we do what we do? What is health insurance? How do you offer health insurance to employees?” [laughter] You know, things like that, that are these like “Aaargh!”

[24:12] So over time - I’m not saying that I did all of that, but I helped to find really great people to come in and help Lullabot to do that, and we have hired a really great leadership team of really capable people. I don’t tend to carry a whole lot of ego when it comes to that kind of stuff. I’m happy to relinquish control and let other people do things when they’re capable.

So I kind of got to a point where I was surrounded by all these really capable leader people, who were running the company, and we had kind of figured out who we were.

There were a couple years that we were kind of looking for the missing pieces… “What are we not thinking about? What are the pieces that are falling between the cracks?” I’ve found somebody to do sales, and I’ve found someone to do HR… “What are we not thinking about?”

But you know, as even those pieces started to get kind of at least defined, if not fixed, I’ve found myself sort of – I wouldn’t say with nothing to do, but just kind of getting antsy. My business partner, Matt, started to see me kind of in that position, and he said “What do you need?” I said, “I don’t know.” “Well, do you wanna take some time off? Maybe you could take a sabbatical and just sort of find your mojo.” When you’re running a company, it’s like having children; you wouldn’t ever consider not being there for them, right? “This is my life.” You don’t even think of it as a responsibility, because there’s not the option to not do that. You have a responsibility to feed yourself, but it doesn’t feel like a burden, it’s just what you do… And in that same way, I was just running Lullabot. But as I started thinking about kind of stepping away, and kind of catching my breath, it was really more appealing; I really kind of surprised myself.

So I did that for a while, and about six months later Matt came to me and said “Listen, I’ve been thinking… If you wanted Lullabot to buy you out, we could do that. That would be a way that we could go”, and he had been doing a whole lot of research about employee-owned companies and just sort of the financial models around all of that.

He said, “We could do this for you, and then if I, Matt, wanted to do that maybe at some point down the road, you would be paving the way for a model for me to do that, if I ever wanted to do that.”

You know, it’s taken me a good period of time to find my identity. For so long it was “the Lullabot guy”, and people would even say “Oh, do you still play music?” and I’d say “Well, I don’t know how long can you go not playing music and still call yourself a musician…?” [laughter] Because I was so entrenched in the Lullabot… I mean, it was emotionally rewarding, there were great people, we were working on great projects - all of that stuff. I’m not saying that it was – but I definitely had sort of set that part aside.

What has that adjustment period been for you? Because I would assume that when you build a business and it’s so successful as Lullabot has been, and you’re running it for so many years… What is that adjustment like to walk away, and like you said before, trying to figure out what your identity is?”

[27:26] Yeah… It’s weird, but it’s been nice not to carry that weight. It allows me to even relate to the people who continue to work at Lullabot in different ways. I’m not the boss anymore. Also, I started doing business coaching, and talking to other people that lead other companies about what they’re doing, and kind of help them to think about their companies, and that’s been super-rewarding. It’s a lot of the same stuff I was doing as the CEO of Lullabot, but I get to help these other people who have different problems out, and share my experience. That’s been really rewarding.

And then I started a new band last year, and we put out a five-song EP earlier this year, and it’s been getting really good reviews and responses. I just had a show on Saturday, and it was really great. It feels really good to be exercising those muscles again, recording, and the more entrenched, creative side of things.

I think that business is creative, and it ought to be creative, but kind of at scale, when there’s a lot of money involved, and I guess a lot of people involved too, you wanna double-check; you wanna make sure the math adds up… So it’s just really nice to be back where I can just, like, “I’m gonna write a song that has one note. The whole song is just one note. I can do that.” People are gonna say “Oh, that’s weird, I’m curious to listen to it”, not like “Oh my God, you’re gonna drive our company into the ground!” [laughter] You know, like “That’s a crazy idea! Why would you do that?!” So it’s nice to have that outlet, and it’s a nice balance.