IndieRails

Andy: 00:02

For me, I've never ever, ever regretted going to a conference ever. I've always valued the relationships that I've built with these things. It's always about the human beings who inspire you or become your friends or 3 years down the line move to your town and they go, hey, I've got an idea for a business. I need a software person.

Jeremy: 00:23

Hey, everybody. I'm Jeremy.

Jess: 00:25

And I'm Jess.

Jeremy: 00:26

And we are 2 Internet friends exploring the intersection of independent business and rails. Welcome back to another episode of IndiRailz. Today, we have a special guest, Andy Croll. Andy is a Rubyist, an author, a speaker. He's the CTO of Coverage Book.

Jeremy: 00:43

He's the creator of 1st Ruby Friend Mentorship Program, organizer, Bright and Ruby. And this year, he's the cochair of RailsConf. He's also one of the most encouraging people that I've met in the Ruby world in our community that's saying something. Welcome to the show, Andy.

Andy: 00:57

Well, thank you very much. It makes it sound like a lot. It is a lot. When you list out all the things, it makes me wonder what the hell I'm doing. Thanks very much.

Andy: 01:05

It's very kind of you to say so.

Jeremy: 01:06

I think you've said in the past that you just have lots of elaborate hobbies, it seems like.

Andy: 01:12

Basically, I have a problem with saying yes to work adjacent hobbies. Yes. Like, the bright and ruby I've been doing for 10 years. That was a follow-up to a conference I ran in Singapore called Red Dot Ruby back in 2012, 2011, where I was having a beer at our local Ruby meetup. And I was really jealous at the time of all the local conferences that were happening in the US.

Andy: 01:32

And I was like, why don't we have one? Matts is in Japan. That's, inverted commas, not that far from Singapore. It's actually quite a long way from Singapore. It's in Asia though, so I thought, well, I'll just email Matts and see if he'll come.

Andy: 01:44

And he emailed me back, like, 2 days later saying, yes, he would. So I was like, okay. I guess I have to do this now. So, yeah, that's how I ended up on this sort of conference organizing side hobby that I have.

Jeremy: 01:54

Yeah. Have you used a similar pattern with the other ventures you've had? What draws you into these side ventures?

Andy: 02:01

I think frustration driven development, I think, is probably the way to think about it. I just take it further than other people would. I'm just gonna code a thing up or I'm just gonna launch a website and see what happens. That tends to be the way I do it. Also, I'm not very good at giving things up.

Andy: 02:17

I persist. Hence, 10 years of bright and ruby, hence the first Ruby friend thing still being a spreadsheet that I manage and matched all the people manually for now. It's all kind of manageable. It's all about systems, and you guys know being sort of independent contractors. It's that freelancer mindset.

Andy: 02:33

I do have a proper job at Coveragebook. Even that was a freelance gig to start with that sort of expanded. That freelancer able to chop and change and, like, keep a lot of context in my head with, like, various systems of notes and to dos and scrabbles and bits of paper and Post it notes and all that stuff. Just trying to keep it all just about surviving whilst not drowning in it. That's the life.

Andy: 02:53

Right?

Jess: 02:54

I've been thinking about this a lot lately about keeping a focus and somebody who has usually an entrepreneurial mindset, they're going to just go in all different directions. And sometimes that's good, but a lot of times you just spread yourself too thin. You got too many irons in the fire. How do you control saying no or keeping your focus on just a certain number of projects at a time?

Andy: 03:18

I sort of wish I knew. Like, I feel like I occasionally take, I'm feeling it right now. So the RailsConf thing is an additional thing I hadn't planned for. And when I mentioned it to my better half, the eye roll was audible.

Jess: 03:32

I've seen those eye rolls.

Andy: 03:33

Yeah. That what are you doing? You said you were gonna take it easier this year. But it's an opportunity, and it's also, I think, a duty to sort of give back to the community. And so, like, when I get the feedback from individual people that they like stuff, that's generally what keeps my interest going, really.

Andy: 03:51

And that's kind of how I do it. I actually don't start that many things. I just get quite good at maintaining things with low effort. You're probably finding this a bit this year, Jeremy, with Blue Ridge. Right?

Andy: 04:01

Like, it's easier this year. Right? It's both easier and harder.

Jeremy: 04:05

I am actually not involved with

Jess: 04:07

Oh, you're not involved. This year.

Jeremy: 04:09

This is one of those things I have to have this conversation with a lot of people. Long story short was in November of last year, I was trying to decide if I could pull it off again this year

Andy: 04:18

Yeah.

Jeremy: 04:19

And realized that I didn't have the time, energy, finances to make it work this year. So I told the team, can't do it in 2024. Let's plan on doing every other year. I'll just come back. I'll be ready in 2025.

Jeremy: 04:31

And they were like, okay. And they went away and they came back and they said, well, what if we did it without you? Would you be okay with that? And I was like, oh, would I be okay with that? I ultimately said, yeah.

Andy: 04:41

This is my thing. You're gonna need me out.

Jeremy: 04:44

Right. Right. Yeah. But at the same time, I was so thankful and excited, and then they were ready to just carry forward. They had enough energy and excitement for it.

Jeremy: 04:54

And this year, I'm just gonna show up.

Andy: 04:57

That's awesome. I wish I could do that.

Jeremy: 04:59

All the hard steps will be done. Just

Andy: 05:01

show up.

Jess: 05:02

That's what I told him. I said, that's something to be proud of. Yeah. Plant something, and it can continue without you.

Andy: 05:07

That, in many ways, is part of my own issue, which is I'm not very good at playing with other children on my side hobbies. So Brighton Ruby is great venue in Brighton. Like, it's an amazing venue, and they do everything. Like, they do concerts and they do dance shows and they do everything. 300 to 400 nerds showing up in the middle of the day is the least scary thing for them in the history of the world.

Andy: 05:27

And knowing the venue and knowing the day and knowing exactly what I want, we discussed it when you were painting the Blue Ridge. Like, knowing what the event is means that it takes little effort for a long time for me for Brian Ruby. And a lot of the things that I do are like that. There's not much for me that is lots of intensity. It's just sort of a gradual increase.

Andy: 05:46

It would be great if I could hand it off and have it happen to me, but probably more of it sounds like I'm more of a control freak.

Jeremy: 05:52

I think you could talk to the volunteer team, and they would tell you.

Jess: 05:55

I'm like a triple threat.

Jeremy: 05:57

It was a challenge in that sense because you put so much of yourself into something that was really hard. But on the other hand, my wife reminded me that I really like starting things. That tends to be my pattern. I really do get most of my energy out of saying something, get off the ground. And once it's going, I want it to keep going, but I have less excitement or energy around that.

Jeremy: 06:20

So it was definitely hard, but also very glad

Andy: 06:25

Yeah.

Jeremy: 06:25

Yeah. Yeah. That's awesome. And relieved.

Andy: 06:27

Yeah. Yeah. There's a definite relief. I'd say I've slightly inherited my dad's stoicism. He was quite a stoic man.

Andy: 06:32

I think I have that. I'm not so enamored with the starting. It feels like there's a build and I can resist and I can resist. And then eventually, I just go, oh, for god's sake. Someone's gonna do this.

Andy: 06:43

Yeah. And then I do it, and then I keep doing it. Even as I'm building things, I'm trying to make them easy for myself because I'm so lazy that my laziness comes out as an incredibly optimized series of an enormous amount of stuff, which means I'm doing lazy wrong, but that's my pattern.

Jeremy: 07:00

I like that. And I probably need to work on that because I'm not good at the good side of lazy optimization. I end up doing lots of repetitive things in my life that I'm not always good at optimizing for. So maybe I would scale better if I did that. Took your approach.

Andy: 07:17

There's systems as well. Right? Like, it's bring checklists, and I do this at work all the time as base cam reminds me that I need to do a thing, and base cam reminds me on a Monday morning. What did you say you were gonna do last week? Did you do it?

Andy: 07:27

Did you? Did you actually do it? Really? Yeah. Yeah.

Andy: 07:31

Yeah. Exactly.

Jess: 07:32

I was just thinking about the same concept when you're talking about conferences and being able to let other people work on them. I think as software developers, we have the same problem with software projects, or at least I do and being able to turn them over or let other developers work on them. Do y'all struggle with that?

Andy: 07:51

I both do and don't, but I've been doing it long enough. I've sort of been in Rails apps long enough that I'm so aware of how different my taste is even than like 3 or 4 years ago in the code that I'm producing. So I don't hold tight to, like, this is the way you must do something. I'm always adjusting my taste in the Rails apps that I'm putting together and the Rails apps I maintain. I can do something.

Andy: 08:12

So we rebuilt our software at work coming up to 3 years ago now. It was quite a difficult process. There's a talk I put together about that. But the things that we decided at the time were overreactions to how we'd done it before, and now we're pulling it back. We're refactoring out some of those patterns and some of those decisions and technical architecture decisions that we made thinking we were gonna go in a certain direction when in reality, the software and the users have taken us in a different one.

Andy: 08:36

So I'm quite am I good at whole I don't know. You have to ask the team, really. I I don't. Yeah. I am a terrible person to ask that question really.

Andy: 08:44

Yeah. I get that. What about you? Do you find it Jeremy, do you find the difficulty handing software over?

Jeremy: 08:50

I used to. I learned Rails on a code base that I spent 10 years building, and I stayed probably longer than I needed to on that project and in that company because of the level of ownership that I took over that code base. And when we finally hit a point where we needed more people, it was growing very slowly. And it was not the product of the organization, but it was central to the org. When I finally needed to bring more people in, it was very difficult to sort of seed control and let other people make decisions that weren't mine.

Jeremy: 09:26

And that was a really good teaching moment for me to realize how much of my identity I'd put into my own code, which is this thing that doesn't live that long. Over the course of many, many commits, what's left of the lines that I wrote is less and less and less, and the importance I assigned to that was outsized. And it was also limited by me. I probably created limitations because of the way I approach that project and trying to maintain control. I do like doing things solo.

Jeremy: 09:57

I've spent a lot of my career doing that, but I've also come to realize that's not optimal. That's not optimal in of itself. So there's a place where starting projects can make sense. But if you want somebody to grow, you need to bring other people along. Other people need to come in as well.

Jeremy: 10:13

That was a huge teaching moment, and it let me take a breaking out of that, sort of leaving that code base, let me take a step away so that I can approach other clients and other projects with less of my identity wrapped up in that code base.

Andy: 10:27

One of the key things that I found to break any sense that I had of that was I did a couple of venture backed startups earlier in my career, including one that I cofounded. There is nothing that sort of removes your ownership of the code like, this doesn't make any money. We're shutting down. Well, you can keep working on it if you want, but we are not gonna pay you because there's gonna be nobody here. That really helps break that particular ownership.

Andy: 10:50

I own this thing that doesn't do anything and doesn't make any money. And I think, actually, that's one of the healthier things about there's not that many healthy things about the VC model, but certainly there's an engineer working inside it. But that's one of the things. If it doesn't make money, then you can't persuade yourself it will eventually because they've literally thrown money on a bonfire of engineers to make those things. And if the market doesn't want it, it's apparently clear.

Andy: 11:14

Not an efficient way of doing it, but it does very much take away that sense of, I've got this Rails app I've been working on, and I just know in 4 years, I can definitely grow this thing into a SaaS. I'm just like, no. What you've done there is you've taken a personality defect and turned it into software.

Jeremy: 11:28

We kinda jumped right in to a lot of different topics. I'd love to hear about how you got started with Coveragebook and what Coveragebook is. I get a little confused. You have a beautiful landing page, but I don't understand it, what the product is. So I'd love to hear where this product came from and then

Jess: 11:44

what problem it solved.

Jeremy: 11:46

Yeah. And then how your team's grown over the years and what your experience is now as CTO?

Andy: 11:51

So CoverageBook was started before I arrived. So it's a 10 year old piece of software. I've been there for 7 or 8 years now. It basically is spun out of an agency. Like so many things, so many software projects like so many failed software projects, it span out of an agency trying to scratch its own agent and do product.

Andy: 12:08

Product. Right? Because agencies have a very different model to a product business in terms of the cash flow in and out. But Gary, who is the still the founder of CoverageBook and still there and sort of my partner in crime in the day to day, he basically was done with agency work. He worked in a PR agency in Brighton in the UK or Propellanet.

Andy: 12:25

And the founders of PropellrNet, they'd grown the agency to 10, 20, 30 people at that point just doing public relations and what they call SEO PR or digital public relations. So sort of PR, but with sort of some idea of measurable outputs and sort of driving traffic and a bit more measurement around it. And so Gary wanted to start a product business, and so he sort of read Getting Real by 37 signals. And they found a colleague of mine, someone who I'd done a conference with, John Markwell, who ran a co working space in Brighton. He's a consultant for sort of early stage businesses, and he sort of ran a boot camp inside the agency for a couple of teams.

Andy: 13:03

And, of course, the first project they built was a CRM because every agency Yeah. In a niche believes they need their own CRM.

Jeremy: 13:10

I've been tempted by the CRM as well.

Andy: 13:12

For sort of influencer management type stuff. And it turns out that one of the features actually could have been successful, but it needed, like, an enterprise sales team. Were on the brink of selling it to a big supermarket in the UK, and then they sort of stopped themselves and went, wait. Wait. Wait.

Andy: 13:26

Wait. What the hell are we doing? We don't want a sales team. We want some signals model or they wanna sell by credit cards to lots of customers rather than multi 1,000 pound or dollar deals to a big enterprise. But there was one feature of that, which is a thing in the PR industry, which is when you get all of your coverage in, you then tell your clients, both internal and external, that you've done a good job, and you do that by showing them the coverage you got.

Andy: 13:45

In the old We are the digital equivalent of that. So it's, did you get TV coverage? Did you get radio coverage? Did you get We are the digital equivalent of that. So it's did you get TV coverage?

Andy: 13:57

Did you get radio coverage? Did you get online coverage? Did you get social coverage? And we basically pull all that together in a beautiful report and then let the people providing the PR services do a job of explaining their value to people. And it turns out there are thousands of PR companies in the world because the Internet and the world is more massive than I can possibly imagine.

Andy: 14:17

I didn't know this was a thing. So when I joined, we had about 500 customers. We have about 3000 now, about 12,000, 13, 14, 15,000 active users. We've done a full rebuild of the app. We also launched a second SaaS business by accident.

Andy: 14:36

One of the things the team was good at and still is good at is engineering is marketing. So we built ThinkGrid on to the public, which was like a free tool that would point people back at coverage book. It's sort of adjacent. It was kinda like SEO stuff. And then we slapped a credit card form on that at some point, and it took off like a rocket.

Andy: 14:53

And, eventually, that had, like, the other half of 1,000 and something users, and we sold that business separately. So the founders of the agency who plowed all that money into the business boot camp in the beginning and had stepped away from the agency as well, they did brilliantly out of that of out their long and expensive decision to get into product. They eventually have done fairly alright, and they're not involved in the day to day. They both live in the Alps. It's very nice.

Andy: 15:17

They're lovely chaps, and their families are out in the Alps in in France. So so now Coveragebook is just an ongoing software business.

Jess: 15:24

Does payment get calculated based on the amount of coverage? I guess it does indirectly, but are there any, like, direct like, if we get you this amount of video coverage or if we get you published in 10 magazines, does that calculate into extra bonus payment, or is it not related to payments?

Andy: 15:45

So we charge our customers on the amount of coverage they put through. That's our major sort of value metric, if you are familiar with that term. That's the one that scales with the amount you pay us. Mhmm. Also, to a certain extent, the number of people on your team does does as well, like, on the $99 plan, like, you're only allowed 5 people and you get, like, a 100 bits of coverage wherever they're from.

Andy: 16:04

So we don't discriminate against Uber niche blogger who is very influential versus getting stuff on the BBC website or in the New York Times. So, yeah, it's a great little business that sort of serves an industry niche, and it's quite fun to work on. And we operate in a very calm and considered way. Like, we all work 4 days a week. There's only 13 of us in the company.

Jeremy: 16:23

How many developers? About half of

Andy: 16:25

that is the product team. So there's me, 1, 2, 3, 4, taken on 3 juniors in the last 12 months or so. So 3 of those are very junior. So, yeah, it's about half the 2 thirds product team, couple of support folks, and some marketing effort. So, yeah, it's very lean.

Jeremy: 16:43

How close do you work with the owner in terms of the vision of the product? It sounds like you're working very closely.

Andy: 16:50

Gary and I kinda set the agenda. Every couple of months, we get together. We pull together the things we should be working on the next couple of months. Like, we did this for the year. This is our plan for the year.

Andy: 16:58

This is our focus. This is where we think we can do things to the business. I like the idea of being able to focus on a part of the business and try and make the numbers go up. We operate very profitably, very calmly. Like, we leave ourselves plenty of margin.

Andy: 17:09

Like, we don't hire because we're trying to grow faster because also I'm not totally convinced that works in most businesses. So we sort of set an agenda for the year in terms of we wanna do this, we'd like to grow this much. Every year, we sort of grow around 20% and a bit less than that, some years a bit more than that, some other years. And I like to think that maybe this year we can really impact that line by working on the right stuff, but we'll see. When you get to our era of business, lots of people in the industry know who we are.

Andy: 17:37

So things that worked in the early days. So I know for a fact, like, Twitter ads worked super well for us when they were just getting known in the early days of CoverageBook. And now we've turned off all paid advertising, and our numbers haven't really changed. So it's just like there's a different eras of business. Doing the thing that got you here is the the classic doing the thing that got you here isn't gonna get you there.

Andy: 17:56

Right? So it's very easy to spend money on social ads, LinkedIn ads, Twitter ads, whatever. You just have to be sure that they're working. And they definitely did used to work because when we turned Twitter off for a month, we'd notice it wasn't working. But now we turn it off and it doesn't make any difference.

Andy: 18:10

So, like, is that word-of-mouth? Is that attribution is hard? Virtually impossible. So, yeah, that's one of the things we wanna get better at this year is, like, where where our customers hear about us from. All of that feeds into the product.

Andy: 18:21

It's a very small team. Everyone's got visibility of the numbers. Everyone's got visibility of everything. And we discuss it as a group, and Gary and I kind of pull together the projects we're working on for the next 8 weeks, and then we do that all again. Just because it's 2 months, isn't it?

Andy: 18:33

I'm not religious about the number. It's just you could call it a shape up. I read that book, and it's fine. The idea that you don't work on something for too long or take on too much for too long is good advice. Yeah.

Andy: 18:43

I know a couple of folks who work at 37 signals. The thing that the chap I used to work with who works there now says, the thing that you really have to understand about that model is that they really do take the hammer to the scope, and that's the key thing that most folks don't do. And, like, we've been all praying sort of this way for a couple of years. Yeah. Give or take.

Andy: 19:00

Is it 6 weeks? Was it 2 months? Was it 3 months? Was it whatever? Was it a month?

Andy: 19:04

But the key thing, where it's gone wrong is when we haven't gone, no. You shipped something at the end of 8 weeks or the end of 2 months. When projects drag on, it's like, oh, just a little bit more, just a little bit more, just a little bit more. So, no. No.

Andy: 19:17

The point is stopping. There's 2 points to it. One of them is you stop and you reassess, and the other point is you squeeze all your decisions into a small period so that the people who are making those decisions don't have the opportunity to change their mind a month later. Because, like, it's very easy when you're just like, oh, no. Like, user numbers are down this week, and you're just totally overoptimizing on the short term panic.

Andy: 19:39

So it forces me and Gary to have a bit more of a cadence, and it also squeezes all of that thinking into a smaller amount of time and then lets everybody then just get on with the work for the next however long.

Jeremy: 19:50

So it seems, from my perspective, you have this great setup where you have an amazing partner in Gary, a small team that you have just a lot of responsibility over insight into the operations and product in the market. Do you have any advice on how to find a partner like Gary?

Andy: 20:08

Gary was doing this before. And, like, John, who helped them set up, was there before, and he was great for that early stage. And I was brought in on contract because they had a fairly inexperienced product team at that point. There's a couple of folks who are still around from the product side, like our designer and one of our devs has been there the whole way through, but they were much earlier in their careers at that point. Right?

Andy: 20:27

So I was brought in to do some performance work and help them architect things in a way that John was a brilliant prototyper, but that meant that 18 months in, like, the systems were creaking. Like, someone would put in a load of coverage, and it would just pause the whole app for everybody, which is terrible, and you get lots of people paying you money. That doesn't work. So I was brought in on a couple of days a week to do some performance work and advisory. And then gradually, after only 18 months on contract, they eventually said, would you like to join us permanently?

Andy: 20:55

Which I don't know if that's flattery or not. It certainly took him long enough. Yeah. So, yeah, so at that point, I joined up, and then John stepped away soon after that. It's luck, honestly.

Andy: 21:06

For me, this is the best gig I ever had. Before that, I was a company called Housestrip, which was a VC funded Airbnb competitor in Europe, which crashed and burned hard. And was eventually sold off and white labeled to a booking.com or whoever. I can't even remember who bought it now. But one of the big travel companies white labeled Hellstrip and took their platform away.

Andy: 21:25

And in between, I had an absolutely disastrous engagement with a company I mentioned where they hired me as VP engineering to help them grow, and I was completely rejected by the organization as I landed in it within 6 weeks. And I was just contracting. I was just doing bits and pieces for people. I literally went from almost my worst work experience. Powerstrip was great, actually.

Andy: 21:46

It was a dreadful business. It wasn't run well as a VC business, and also it's travel and travels really hard. But, yeah, I went from this 6 week engagement where I was basically the organism of the product team rejected this new entrant asking questions and trying to understand things and almost immediately fell on my feet into this coverage book, 1 or 2 days a week gig, which then expanded into my real job. And it's a case of finding something that suits you. Right?

Andy: 22:11

Like, small companies suit me. Engagement in both the business and the technology side suit me. Like, it fits my entrepreneurial thing. Like, it's not my thing, so I still have that inkling, which I'm sure you folks have, which is like, I want a thing for me. Yeah.

Andy: 22:24

I wanna prove myself in whatever, like, failing I has as a child. I wanna prove that I can do a thing. Yeah. And I still have that, but I don't really fundamentally understand the PR industry. I rely on Gary for that understanding of PR and the marketing world, and I rely on his marketing skills in that world.

Andy: 22:44

It's not something that I could do. So I need that, and I don't understand the PR industry particularly. Particularly. Well, I mean, I have worked in it long enough that I sort of get it. I had to learn, but, like, I don't fundamentally know it in my being.

Andy: 22:54

Like, I know developers or maybe other things. Parts of my life I would know. But so that's a really good match and Gary's good product instincts, but I think of myself as crush his dreams with my scope and my nose. But, like, there's a healthy respect between us. I will say things like, oh, I've let Gary get away with this project.

Andy: 23:13

He wants to build this thing. I said no. We talked about it, and, eventually, we said yes. It's give and take. Right?

Andy: 23:18

So I think it really works well as a partnership, sort of healthy respect for each other's skill sets. And, actually, in many ways, they talk about, like, business partnerships as being a marriage, and there is a certain amount of that. There's a healthy respect, and you hopefully fill each other's gaps. But you have to have the same values. As much as my wife and I argue, we have the same values for what we'd like the kids to be like and what values we have in the world.

Andy: 23:43

And I think Gary and I have, on a business perspective, have a very similar thing for how we want to run an organization, how we want for ourselves to be in that organization. So I think that's a key thing that we've really worked out. It makes me happy. That's the point. One of the one of the things I discussed with my wife is that she doesn't really understand that I like my job because she's never really had a job she's liked.

Andy: 24:01

I mean, I like coding. I like making things. I like the mechanics of my career, but I also particularly like this job because it really suits me. And she's unfortunately never had that in any of her big jobs anyway.

Jeremy: 24:13

Yeah. I've definitely noticed that with friends or family members as well. Yeah. I probably have enjoyed my work far more than most.

Andy: 24:21

Yeah. Why are you still working is the question you'll forget. It's like, on some level, it's a fun puzzle. Yeah. That's one of the great joys of software engineering.

Andy: 24:30

It's lots of fun puzzles that never finish.

Jess: 24:32

Early on in my career, I was one of those fire people who wanted to save up a bunch of money and try to retire early. And the longer I work, I'm like, what am I gonna do if I retire?

Andy: 24:43

Like,

Jess: 24:43

this is kind of fun. What am I gonna fill my time with? And I've changed my way of thinking, and now I feel like I probably will work much longer than I had originally planned.

Andy: 24:53

If I made a bunch of money, if I owned more of Coveragebook and we sold it and I made a bunch of money, what would I do? I'd go and make more stuff for the world that I thought needed to be in the world. I'm not attaching any moral greatness to that. I just see things that could be better, and I want to fix them. That's how I end up doing conferences and co chairing RailsConf and starting little mentorship programs by accident.

Andy: 25:16

It's frustration with things could be better, and I can do it. I can do it from the comfort of my own house with my keyboard.

Jeremy: 25:23

Yeah. Right.

Andy: 25:24

So, yeah, yeah, that's part of what drives me. Yeah. I I agree. You know, I may slow down. One of the other benefits to this job, which I said 4 days a week, and that's designed so that I can make sure Gary and I are both spending time with our kids and everyone who works this at home.

Andy: 25:38

We actually are sort of remote friendly, but sort of geographically close. So, like, we all go into the office. So, like, we value in person time as well as the flexibility of remote. So, like, everyone is south coast ish, so we all try and get in on a Friday and go for lunch together. So we don't have that full remote, okay.

Andy: 25:56

I'm lonely. I haven't seen a human face, not in a 20 square box for a long time. So, yeah, we try and make it maintainable for ourselves. So, like, I'm home for the kids or I can do a pickup or someone's boiler is broken. All of these things that are just life, we try and focus on that as well as to keep it maintainable to sort of

Jess: 26:14

And those are all the great things you can get with lifestyle business or a small company. You can be very profitable, but also you can use the company to fit around all your goals and outside of your business life as

Andy: 26:28

well. Yeah. That thing we were talking about earlier. No one's identity is wrapped up in the success of coverage, but, like, the selling of Answer the Public kind of did that for us, I think. The fact that we've done it twice is kinda like, oh, okay.

Andy: 26:39

Maybe we're alright at this. Like, I don't think everything we would ever create will definitely be a business success. I'm not arrogant enough to suggest that. But, like, there is a sense of if there's an inkling that this could work, we could make it work. That's kind of how I feel about any future projects we might work, Conan.

Jeremy: 26:54

That probably gives you a certain level of calm, confidence that means you don't have to live or work frantically to achieve some kind of payoff or just grind it out in hopes that you'll succeed or something?

Andy: 27:06

No. You gotta enjoy it on the way. Yeah. Otherwise, what the hell are you doing?

Jeremy: 27:09

So one of the things you said a second ago, you were talking about how you'll see a thing in the world that's not quite right and you wanna go fix it. And there are several things that you've done that way in beside ventures. What are some things that you have seen that get you upset or, like, this needs to be fixed, but I don't think I have the bandwidth. Are there any things like that?

Andy: 27:28

Yeah. The genius thing is massive. Right? I'm trying to do my bit. I go and talk a couple of boot camps in London where they teach Rails because Rails and Ruby are a terrific teaching languages, and they let you go from, I don't know what this black box is that I can type words into to, I put words on the Internet.

Andy: 27:46

That's amazing. Gonna get people there in, like, 12 weeks. Those things were amazing. Like, some of the best devs I know have been through boot camps. And this was in the better times of hiring in the US, right, whereas clearly everyone's hiring, but everyone's hiring seniors.

Andy: 27:58

You see talks and the best ones I've seen are just like, yeah. I hire senior developers. I just hire them 5 years before you do. Mhmm. And I can make them.

Jeremy: 28:05

Right.

Andy: 28:05

I was just like, well, if there are so many impressive juniors, impressive post boot camp folks around, what can I do to and we're so friendly in the Ruby community, but the rank and file dev is not being given the chance to hire these people and contribute to their careers at work? What can I do? So I just weaponized the Ruby community's friendliness and just matched people on a spreadsheet. Like, it literally is that simple. Like, it's a thoughtfully put together questionnaire, a 4 page website, and a spreadsheet and multiple hours of my month to put together.

Andy: 28:37

I am trying to get away from that. And then the follow-up to that was then hiring juniors into coverage book. There was some resistance to hiring post boot camp folks. Are we the best environment? Like, I don't think it comes from a bad place necessarily, certainly in smaller companies.

Andy: 28:51

In bigger companies, I feel like it's just laziness. In smaller companies, there's a sense of, I don't want this to be a bad place for someone to have their first work experience in our industry. And I think as soon as you're asking that question, you're already good to go because you care. So if you care and someone comes to you with, I can't solve this PR, do you ignore them, or do you put your tools down, jump on a screen share with them, and help them solve the problem? Well, you obviously do the second one.

Andy: 29:19

Right? And from a pure economic perspective, they are a lot cheaper than a senior dev. I've seen senior dev salaries in the US. You guys could really do it. The bigger teams could really do it Stratifying their teams a bit and, like, getting some junior folks in, and it's incredibly satisfying.

Andy: 29:35

The feedback I get from the first Ruby Friend mentors, this was really valuable to me. I really helped someone. And then I hear every now and then, oh, I got a job off the back of this. That's great. I hear from the devs in my team, at least to my face, say that they really like working at Coveragebook, and they're learning a lot.

Andy: 29:50

And, like, that's the key thing. Right? And I've said openly to them, when you're ready to move or if you want try a different kind of organization and coverage, but, like, we're not gonna grow like crazy. We're not gonna expand to a team of 20. There isn't gonna be huge amounts of opportunity to run teams or work on new technology because we're deliberately boring Railshot Mhmm.

Andy: 30:09

Or as boring as we can and trying to get more boring. Yeah. And I've said to them, like, if you wanna go, tell me well ahead of time, and we will set you up to move on to that next job because I also don't believe that I need to keep people. That's a weird thing when people leave jobs, particularly big organizations where the turnover of software engineers must be, like, 18 months to 24 months, maybe not right now given the slight downturn. Things that I've heard people say to me, people who've left jobs and their manager has gone, you'll never find a job as good as here.

Andy: 30:38

The very fact your manager is saying that means that this is a terrible job and you were right to lose because that person is an idiot. Yeah. It's a way of getting back. We're getting huge value from these genius. Like, we are getting through bugs that we would not have got to in a small team.

Andy: 30:52

Secret of hiring post boot camp devs, They love bugs. They love them in a way that I'm just like, oh my god. I wrote another bug. I'll put that in a tracker somewhere and maybe get to it eventually because that's kind of not. Everything's a little they're so spongy.

Andy: 31:06

They're just getting across the whole product. It's like it's a relatively complex couple of Rails apps that we run, getting in and understanding the problem. And every little solution is a new piece of knowledge. So they're getting that dopamine here. I understand that thing of the days where you spend 4 hours, like, smashing your face against the keyboard and it's really awful.

Andy: 31:23

And they get that every time they fix a bug. Every time they fix one, they just yes. And they get to deploy it to production, and then customers are happy. They're getting the whole cycle over and over again. So, yeah, that's the secret is hire more juniors because, actually, they're both great for your business, great for your ego, and they like it.

Andy: 31:43

I'm really passionate about that, and I really think that's something that lots of industries are bad out. I don't think this is unique to software engineering. I think we give ourselves a bit of a hard time because Mhmm. We like to think we're all amazing and we should be doing better and we're working these quite pleasurable white collar jobs. And we're just like, why are we so bad at hiring juniors?

Andy: 31:59

I'm just like, every industry is terrible at hiring new people and putting the work in to train them and fulfill their needs as much as you can. But someone who's put themselves through a 12 week boot camp and probably had to pay, they have already prequalified themselves, as far as I'm concerned, to being gritty enough to push on their own knowledge. That bothers me clearly because I just ranted for 5 minutes.

Jeremy: 32:20

Yeah. No. I wanted to talk about that. As a follow on to that, are there any words of advice that you have for smaller teams that wanna hire juniors? Things to do and things not to do.

Andy: 32:31

I think you just have to commit to making space in your day to help them. If you're used to having a senior team, which I was used to having a senior team, I didn't have to do one to ones with folks much. We would just catch up, and I didn't have to be so rigorous. And I'm not rigorous about this. Like, I'd basically have a reminder in my to do list thing to have a one to one with everyone who works for me every month.

Andy: 32:53

That's enough. Have a one to one every month, and then every 2 weeks have some sort of retro. And I had a retro specifically with the junior folks to go over what they learned, what was going well, what was going bad. Just you have to overcommunicate is the only thing. The hiring process was fairly easy.

Andy: 33:09

I just had to pitch it lower than most people pitch their junior hiring. You'll find that junior hiring stuff is just, oh, we give them a mid level test, and then it's way too long. You're not trying to hire someone for the code because that's your job is to teach them how to code how you do it. That's the major failing I see in the hiring process. But, yeah, it's getting the right level at some level of technical exercise just to prove that they can think coding e way, but give them all of the rails on that task so that they're not having to configure their machine to do it.

Andy: 33:36

That's the stuff that takes days. Right? And that can sometimes take me days. But it's pitching that at the right level and then making sure they are a good communicator and they are confident in their lack of knowledge. That's what we sort of screened for.

Andy: 33:48

Also, we hired 2 at a time. I know you spoke to

Jeremy: 33:51

Dave Paola.

Andy: 33:52

Dave at the Agents of Learning Tire. When I was hiring my first two juniors, I spoke to him, and his thing was just hire to, hire to, hire to. And I was cool. I'm in. That sounds good.

Andy: 34:03

Contracted with Pivotal Labs way back in the day, and they only used to pair. And so I was familiar with pairing as sort of a training exercise. The thing where you hire 2 people and they unblock each other before they even get to anyone senior in the team is huge. So we did that too. We've just hired one junior this year, and she is working with them.

Andy: 34:23

And it's great because they can see the progress that they've made in a year. Right? So it's a really brilliant self reinforcing marvelousness of humanity. It really, really works. And nobody has worked this out, and I'm sort of baffled as to why nobody has worked this out.

Jeremy: 34:39

You mentioned, Andy, just a little bit ago for career progression for your team members that the ladder coverage book is kinda short. And so when they're ready to go somewhere else, you're ready to help them. And so I really like that. And I've also wondered for you, how do you think about your own career progression and where you're trying to head? To me, it seems like there's this typical approach that developers take moving from smaller organizations to larger and moving up several rungs of a career ladder, maybe to end up VP of engineering or things like that.

Jeremy: 35:12

You're growing in responsibility inside of a larger organization as you grow in influence and skill. When you stay working in small companies and that's what you want and that's what fits you well, how do you think about career progression?

Andy: 35:25

It's an interesting question because I think about this in terms of I try and grow the small company that I'm in. So I'm trying all the time to get better at running the company. I'm not running the company like someone else does the books. But I keep an eye on profitability. I keep an eye on costs.

Andy: 35:39

I keep an eye on team. But also, I am still coding. Yeah. And that's one of the benefits of that 2 month cycle is that I compress a lot of that stuff into a week of decision making about what we're gonna do. And then there's conversations over lunch, and there's conversations just generally happening to sort of maintain that stuff.

Andy: 35:56

For me, it's about, can I keep doing this and make it feel like I'm cheating? I want to keep the business growing, and I want to keep the business earning more money. Not because I'm particularly driven by more money, but because that is a signifier that more people are finding the thing that we're building useful. And then Gary and I both wanna share that benefit with everyone on the team. And I also don't necessarily want to grow the team.

Andy: 36:21

I have 5 or 6 people I have one to ones with every month, and so I am not looking to increase that number or even start necessarily managing managers. Can we keep doing this with the same number of people? Like, coverage book has been around 10 to 12 people for almost the whole of its lifetime, and we use external contractors of things. We use software. That's the bit.

Andy: 36:45

It's like, what can I do to keep this human sized? So I that's my personal driver for my career. And, like, I also have the weird work adjacent side hobbies that give me some of that, am I learning? Am I growing? Am I getting better at what I'm doing?

Andy: 37:00

Yeah. It's just a real mixture of keeping my head down coding, but also keeping my head up to see what are other companies doing, what techniques am I learning, what bits of rails weren't we using because they weren't quite fully baked for our use case that we can now do? So what can we now bring back in? I'm quite good at reading. I'm quite good at taking training for myself as well, like, trying to squeeze that into my life.

Andy: 37:23

And, like, constantly reassessing, is what I'm doing, a, useful, and, b, does it make me happy? And, like, that's all I really consider because what else is there, really?

Jess: 37:32

What is your official position in RailsConf?

Andy: 37:34

I am cochair. Cochair. Cochair.

Jess: 37:37

You've come into this position. You have experience with running conferences, and you've written a blog article about why you should attend a conference. And I think a lot of our listeners are independent people or small businesses. And I'd like to look at it from the perspective of that, which I think you've addressed a lot in your article. But it's a very costly thing to go to a conference, not just the tickets, the hotels, the flights, but just being out of work for a lot of contractors you're losing 1,000 probably double or triple that amount that you paid to go to the conference.

Jess: 38:11

So how do we make this worth our while to go to a conference?

Andy: 38:14

So I look at it in 2 ways. So, like, when I started Brighton Ruby, the key consideration for that was the cost of the ticket should not be a decision point. It should be, do you wanna take the day off? Because I was coming at it as a freelancer. That's my sense for that conference.

Andy: 38:29

RailsConf is a different beast. It's a different beast to organize. It's a much bigger endeavor. Big hotel, big conferences. Some of it's already set up when I came on.

Andy: 38:38

I only came on about a month ago, and I'm not part of Ruby Central. I'm the 1st person who's not part of Ruby Central to help co organize one of these things. For me, I've never ever ever regretted going to a conference ever, any conference. So I've been to business conferences. I ran a conference called LTV Conf in Brighton.

Andy: 38:58

I mean, it's basically the key audience for this podcast. Right? It's indie businesses and software businesses. So we ran that for a couple of years, and no one regretted going. Some people didn't get as much out of the content depending on the stage of their business, like, whether they were way too early for it or whether they were one of the speakers and they felt like they didn't get any content that was aimed at them.

Andy: 39:16

They were already running a 15 person business, and they didn't feel like there was much for them. It was more the early stage entrepreneurs. But I've always valued the relationships that I've built at these things. It's always about the human beings who inspire you or become your friends or 3 years down the line move to your town and they go, hey. I've got an idea for a business.

Andy: 39:36

I need a software person. This person. Or I need someone to send to check my Rails thing, or I have a project I don't wanna do anymore and I wanna hand off. Like, I've got a Rails app I'm supporting. I don't wanna do this Rails app anymore.

Andy: 39:46

I feel like I've burned my bridges with the client or whatever it is. I like but you can hand it off to another person safe in the knowledge that you're doing a good job of providing value to that person. So for me, it's all about relationships. And I quite like speaking on a stage. Some people don't.

Andy: 40:01

Some people really love the talks. Some people prefer the workshops. RailsConf, I'm not gonna lie. It's not cheap, but I think the value you get over time and the sort of endorphin bump you get from the bigger events is really quite something. I do find after those events, I want to go and hide in the cave because although I can present fairly extrovert at these events, don't mind being on stage and talking to people.

Andy: 40:24

Afterwards, I'm completely shattered because I've been, like, jazz hands off Oh,

Jess: 40:28

me too.

Andy: 40:28

For for days days. Right? And we're all like that. Right? And some people need to take time off in the middle of it.

Andy: 40:33

But you just have that nice general low level endorphin bump after one of these things that make it worth it. And the connections that you build I think about it in terms of coverage, Brooke. So the only reason I ended up at coverage was because I put on Brian Ruby. But, equally, there's so many people who you hear the stories, oh, I met that person at that conference, and then 2 years down the line, I got a job with them, or 2 years down the line, they brought me in as a consultant, or 2 years down the line, something else happened. Right?

Andy: 40:59

If you don't go to these things, you're not increasing your luck surface area at all. The idea of increasing your luck surface is a huge thing in a career. Right? Because you can throw out all these bets, and, like, maybe they don't pay off, but one of them will. Although, you know, we don't like to talk about the VC track.

Andy: 41:14

Track. That sort of like throwing out a bunch of bets that fail and then having one outsized impact from one thing. And if you enjoy it and if you go there and you amongst your people, that's incredibly elevating for your soul, I think. I think you should go because secretly, they're fun. And for RailsConf, I'm really concentrating on putting together a program that is technically useful for people.

Andy: 41:35

So I want this year to be really strong in terms of I can take some stuff away and take it back to my team or take it back to the projects I'm working on and actually apply it. That's what I'm looking for from the program.

Jess: 41:46

I really like the quote that you think I pulled from the article. It says, If you don't attend the event, there's no chance of serendipity and unexpected insight from a talk you might have avoided or a conversation in the hallway where a new approach to a long approach to a long running problem presents itself. And I think you can tie that back to the question that Jeremy asked earlier, do you have any advice for finding cofounder that you can work with or lifelong partnership?

Andy: 42:11

You gotta put yourself out there. Right? Like, it's been a while since I was dating. Yeah. And, thankfully, podcasts are an audio medium, so you can believe I'm very beautiful.

Andy: 42:20

But if you don't put yourself out there, you're never gonna get those things. It's it's totally about getting out there and finding people, finding your people, finding people you get on with, or finding people through people. Right? Like, it doesn't even have to be people who attend the event. I just think there's so much in a big conference.

Andy: 42:37

And the big conference is different from the little conferences. Right? Like, Blue Ridge and Brighton are different beasts to a RailsConf, but they have similar but different benefits. You end up in a place you wouldn't necessarily go otherwise. You end up in a break from the day from your regular coding schedule is just as important as doing 3 more days of consulting.

Andy: 42:56

And you can do half days at a conference. So you don't have to take all of your hours off. You can do a couple of hours so you can keep things ticking along. You can do some simple PRs on the flight. You can do some bits and pieces.

Andy: 43:07

Flying's actually really good if you have to fly to a conference or you have to get a long train to a conference. Like, I got a train to Amsterdam for Rails World, just like the most civilized experience. I was able to sit next to my friend, Taekin, and we caught up about his career and my career, and we both did a bit of work. It was a very productive 5 hours that we wouldn't have had otherwise. There's all these things of reasons to go.

Jeremy: 43:28

If I could go back to me in my twenties and give myself advice, back then, I was not going to conferences. They just felt too expensive. But if I could go back and say, go to conferences at least 1 a year as much as you can afford to. And on top of that, know that you belong there. Mhmm.

Jeremy: 43:44

It took me a long time to believe that I actually belonged, that I would fit. Even having done development for many years, it just still felt like, no. Those are the cool kids or those are the really serious people, the really, really smart people or whatever. You belong. If you're in this, if you've done rails new, even if you haven't, you belong.

Jeremy: 44:02

You fit, and you don't have to be embarrassed about that.

Andy: 44:04

If I prove nothing else, it's that the people at conferences are not the cool or clever kids. Like, I definitely approve of that. It's just like, I have no idea what I'm doing, but I have a half decent guess. And, like, if I'm getting it wrong, someone will tell me because there's people there.

Jeremy: 44:19

Yeah. And the other thing would be like that. Sometimes you can go to a conference desperately in need of something, in need of a job, or in need of a connection, and that can make it harder to just enjoy it and be yourself. And the best connections come I've found, personally, the best connections at conferences have come when I've been the most relaxed and just been present in the moment to really enjoy it and enjoy the people I'm with and not assigning this one has to be the one that I get the certain value out of. That makes it really difficult to connect with people and to be present and really enjoy the experience, which is really essential.

Jeremy: 44:58

But just trusting that you are planting these seeds, going to these conferences, you are increasing your look surface area, and it will pay off somehow. And that's kind of the conclusion I've come to now.

Andy: 45:08

They're also tax deductible breaks from work, so that's also valuable.

Jeremy: 45:12

Yeah. Absolutely.

Jess: 45:16

Andy, thank you so much for coming on today and sharing with us about your experiences in so many different areas from conference building to business building to friendship building. And before we go today, where do you want us to send people? Where do you want us to plug and help you out?

Andy: 45:33

Oh, there's a couple of things. It would be amazing if you have the capability, if you're sort of your side of the pond. Please come to RailsConf. I think it's gonna be a really, really strong event this year. We've got a cool second day of workshops and hack day where you'll get a chance to take the inspiration from the 1st day and turn it into real code.

Andy: 45:51

If you're on my side of the pond, then Brian Ruby is happening in June. And if you're at all interested in hearing any more from me, which I imagine after an hour of this, you probably aren't, I run a newsletter called 1 Ruby thing where I tempt every fortnight ish to send out a Ruby tip or something. And if you want to help mentor the next generation of Rubyists, then first Ruby friend is the other one. I assume all of the links will be in the show notes.

Jeremy: 46:17

Absolutely.

Jess: 46:18

Of course. For us US people, what is a fortnight?

Andy: 46:21

It's 2 weeks. Got it. Or 3 or 4 depending on how my weekends are going.

Jeremy: 46:30

Thanks, Andy. I'm definitely gonna be there in Detroit for RailsConf. I'm excited for that. I can't make Brighton this year. I'm gonna be in Maine at that time, but it's on my list.

Jeremy: 46:39

I'm getting to Brighton one of these days, hopefully next year.

Andy: 46:42

That'd be great. I'd love to come to you. Please. Please.

Jeremy: 46:44

Thanks so much, Andy.

Andy: 46:45

Alright. Cheers. Thanks very much, chaps.