XO Ruby is hitting the road

Well, we’re here with a good friend of ours… A good friend of mine, at least, from back, back in the day, back in the Hashrocket days. This is OG, early days Ruby, Obie Fernandez, leading the charge, building apps on weekends… And that’s where I met you, Jim, but you’ve been in the Ruby world for so long, and now you’ve got this roadshow you’re doing, you’ve done conferences before, Madison Ruby… Welcome to the show.

Thanks so much for having me. It’s a pleasure to be here.

What do you think about the past? What do you think about Ruby, where it’s going, where it’s been? Let’s catch up a bit. What are you thinking about Ruby?

We’re still building our business on Ruby, and definitely there is a bit of a renaissance… In fact – so we’ll get to the conferences and whatnot, but one of the bits of feedback that we’ve been getting from people who haven’t been focused on the community is “Oh yeah, that was really cool in 2010.” And it was cool because the promise of being able to deliver a web app and a mobile app, and all in one codebase. And with Hotwire Native, that’s coming back. Speaking with –

Can you give like maybe a deeper detail? Like, it was 3, 2, 1… It was revolutionary. This was groundbreaking, and I think a claim to fame for Hashrocket, to be – one, you had extreme talent. You had a great team to execute, but you had –

What’s Hashrocket?

Okay, there you go. Let’s go back to Hashrocket. There you go. Tell the whole story, Jim.

Yeah. So Hashrocket was the first boutique Rails consultancy. And so we started in – I actually got hired in 2007, before Hashrocket was a thing. There was a client involved, and then they decided to build a consultancy out of the team that they had built to develop that software. So we became Hashrocket… And sort of early startup days, lots of late nights, and lots of alcohol, and things like that. I’ve grown up, but – yeah, it was an incredible time. We had people from various backgrounds all over the US that sort of assembled in Jacksonville beach, Florida, and we were just very excited about the technology. It was also right around the time that GitHub started, and Twitter… So it was early, early and pretty fantastic days.

Yeah. Heroku… Adam, how did you know Hashrocket? How did you know Jim?

Well, I was an up and coming Rubyist. I wanted to work there so desperately. I was like “Y’all are so cool…” The Hashrocket logo was the coolest, still is the coolest. It literally was the Ruby Hashrocket. Just all the right vibes were there. I actually met Obie Fernandez, who is I think a DJ, and now a dad, and growing up like the rest of us, and stuff… And we’ve actually wanted to get him on the pod a couple of times, because I think he’s kind of bullish on like Ruby and AI… And I’ve been meaning to catch up with him, personally, in podcasts, professionally… But I knew of Hashrocket mainly through friends. I met Alan Branch, and Steven Bristol, and others… And I really don’t know how I connected to Hashrocket. I just know that when I went to Future Web Apps, which was Ryan Carson’s conference for web apps, which was a big, big deal then… This is, I think, in 2008, 2009. It was in Florida. And as a podcaster, you get invited places, and so Ryan invited us out there. I think we actually had to pay our own flight and hotel, Jerod, so we’ve grown up a little bit since then… But I was happy to go anywhere I was invited at that time, because I had nobody; I had no network. I was at the ground floor. And even that era was, I think… A lot of the networks and connections I built on - Jim, you’re included in that - since then, really.

And it was kind of funny, because when we were trying to get to the conference, we had a – I think we had a rental car, or Alan had a rental car. And we were kids. When I say “We were kids”, we were just young, and we were stupid. We did whatever we wanted. It was just a whole different world then. And Obie was in the car, and of course, I’m like fanboying, because Obie’s cool. And we were podcasting in the car, and it’s just like – it was nothing like it is now, but it was so raw and so different. It was like “What is a podcast?” It was so weird. We were walking around with like short microphones, wired to this thing, and just like… It was epic.

[08:09] But that’s when I met Obie. We walked the beach in Miami beach, at night, and just talked, we got drunk, we did things we probably shouldn’t do, like when you’re young… And I really wanted to work at Hashrocket, because I was like “You guys are the coolest, you’re doing this cool stuff… And if I come there for a month, or do like an engagement”, they’d call them engagements, “I can get 25 grand for an engagement”, which would seem like a million dollars to me… And I’d get to work with some of the most highest caliber talent out there. I’m like “Even if I’m not as good as they are, I will learn something through this engagement.” I never got hired. It was so close… Obie did want me on the project, but it just didn’t work out… And I think I got another gig and just moved on, or whatever. But that’s how I knew Obie. I think Obie was kind of famous, to some degree, in the early Ruby days…

For sure.

He’s written books, he’s given talks, he’s led the way in a lot of cases… And I think at some point Obie personally kind of like stepped back from the light. I don’t know, really; I’m not sure of his story. You may know, Jim, because you work with him more closely… But that’s how I was connected and how I knew Obie, and how I knew Hashrocket… And it was just such a – these guys were rock stars, Jerod; you know this. They were rock stars, man, back in those days.

Yeah, certainly. Steven Bristol, if you were tied to him, he and I were good friends.

Yeah.

And he was local to Jacksonville. He was on the other side of the city, probably 45 minutes away, but…

And a Rubyist. Everything was built on Ruby.

Famous in his own right, a Rubyist…

Yes.

And he and Alan were just delightful people. I still go down every time I’m in Florida, I try and get over to Panama city and visit Alan, who is now a mayor of Panama City Beach.

I heard that.

Yeah.

So cool. So cool.

Yeah. So the way that I got to Hashrocket was I worked at the state of Wisconsin department of financial institutions, I was in the .NET stack, and I saw this video about building a blog in 15 minutes… And then me and my coworker started diving head deep into Rails on the side. He was a little bit more fluid than I, and so he saw a post from Obie saying that they were looking to hire people, and he literally just flew down and showed up on his doorstep. That was John Larkowski.

That thing rings a bell. Was that like Obie’s right-hand person, and like just in every detail of Hashrocket?

Yup. Yup.

Yeah, okay.

Absolutely. And so he came down there, they were pairing all the time, and they had four people, and then one of them wound up stepping away, and so they needed a fourth. And John was like “I know a guy.” And so I went down and interviewed… I spent a week in Florida interviewing… Again, made some mistakes… But I came back home, told my wife that we’re moving cross country, and went back shortly thereafter. We packed up the house and six months later we were living in Florida.

Wow.

How long were you there? Or are you still there?

I’m not still there. We lived there for four years or so, and then the call of coming back home was a little bit too loud. So now we’re back in Wisconsin. When I came back, I took what I had learned down there and I took part ownership of a consultancy in Madison, and have been basically – I worked with them for two and a half years, and then started my own consultancy soon thereafter.

[11:48] Ruby’s been through some really interesting eras, I think. You know this, Jerod. You’re a Rubyist at your core. I mean, I’m not speaking to the choir. I mean, I am speaking to the choir here, but… I feel like there was this – the video you alluded to was DHH explaining how you could build a blog with his “Whoops” in 15 minutes, which was just groundbreaking… But I feel like that broke the mold for what was expected to get an application built. Now, deploying Ruby in those earliest days was super-challenging, and that’s what open source is about, right?

For sure.

These things all came out of how to actually deploy and run an application in production. And it got easier over time with Heroku, and things like that, and Engine Yard… But this was such an interesting era for, I think, software. It’s either interesting because it’s interesting, or it’s interesting because my personal history is tied to it… Like, the nostalgia I have as a 40-something looking back on my life is just littered with good days of Ruby, and this new framework called Rails, Ruby on Rails, to take us into this new thing… Which was building apps quickly, with CRUD, and scaffolding, and these unheard of ways to do things, easily, more quickly, and with more joy.

What does that bring up to you, Jim, when you think about these olden days? Would you call them the good, old days? Is that how you’d frame them? The good, old days?

I feel like when you say “the good, old days”, that suggests that these days are not good.

Yeah.

Or like it elevates those old days. And not to say that those weren’t good days. These are good days, too.

For sure.

Technology-wise. We’ve got our challenges in front of us, but whatever. I think – yeah, that period of time was a lot of fun… But I think we also kind of put on those rose-colored glasses a little bit. There were things like Merb, and there was a whole “We’re going to fork the codebase, and people are going to go in a different direction for a while”, and then things got resolved… And things got better for everybody. So yeah, there certainly are a lot of moments in there, both at the community at large, through my experiences and whatnot… And most of them were really good.

And you’ve never left. You’re still doing Ruby, still running Ruby-related meetups and events… Has it been consistent for you? Like, from 2010 to 2025?

Yes, it has. I think the thing that changed was events; the pandemic got rid of events, for a period of time there. And so we did Madison Plus Ruby from 2011 to 2018. We actually stopped just before the pandemic. But we had done a Madison Plus Ruby event in Chicago, we had done a Madison Plus Ruby event in Los Angeles… So it was traveling with those back then as well. And then the pandemic just sort of shut everything down.

We moved – I think like a number of people, we moved out of a city center, and we’re sort of out in the middle of nowhere right now… And I don’t have a local community, so I’ve had to sort of seek it out. And that’s a little bit the genesis of the events that we’re looking forward to over the next two months, which is XO Ruby.

The feedback that I constantly get from meetup organizers is that it’s hard to get people to show up every month. And so if they get a good speaker, or if there’s some coincidence with something that’s happening in town, they’ll get spikes… But then attendance is up and down. It’s easier in a place like New York or Chicago or wherever, but for the smaller towns, it’s a little bit more difficult. And it’s so easy to not put on your shoes, it’s so easy to not leave the house. I can go on YouTube and find a thousand talks to watch, or what have you.

[16:08] Right.

And I think the big thing - and Adam, you alluded to this earlier - for me is that in-person connecting with people. It is the ability to sit down… One of my favorite stories from a conference was talking to an attendee from Madison Ruby, and they were so excited to sit down with Tenderlove… And they talked about America’s next top model for like an hour. And it’s like, you would never think, looking at Aaron’s public persona, that that’s the thing that you’re going to wind up in a conversation about.

So I think there’s so many surprises that happen when you talk to people face to face. Or I really want to talk to Adam, but he’s talking to somebody else over there, so I’ll talk to Jerod in the meantime. It turns out Jerod and I have things in common that we didn’t know. And so there’s this serendipity that’s possible in in-person events that just – you cannot replicate it in online events. Or if you can, you have to be extremely intentional about it.

You can’t replicate it, and you also can’t guarantee it either. And so there’s a risk involved, and like you said, it’s so easy just to keep your shoes off… I think that it’s hard for folks to see that value when it’s variable, and when there’s so many barriers to getting there, to sticking your neck out, to shaking a hand that you don’t know… To all the things, when it’s just easier to stay home and watch videos on YouTube, or watch America’s Top Model.

What does a small group look like, and what does a big group look like? What’s the difference? We’re talking like 10 to 50 people, or like 2 to 20? What numbers are you guys talking about?

For meetups today, you mean?

Yeah, you were talking about people struggling maybe with Madison, or…

Yeah, I think on the smaller end you’re talking 5 to 10 people. On the larger end… You know, San Francisco’s an outlier in a lot of ways, but I think they regularly get a hundred people or so. I could be wrong about that number. Chicago’s routinely 40 to 60 people, depending on the speaker… And as I’ve been doing research for XO Ruby, Columbus Ruby Brigade, which was always very strong… You know, it appears to have made it out of the pandemic, and they’re doing pretty well to this day… But I would say that that’s not super-common.

Are speakers always involved? It seems like you could do meetups just for meetups’ sake, like “Let’s just hang.” And that might be less – maybe it’s more intimidating, maybe it’s less intimidating… But does that work or no?

I’m a consultant, and so the answer that I give most often is “It depends.”

Okay.

But you’re right, it does sound easier. The real answer is “What do you do instead?” There are lots of groups that just do social nights, and that’s less intimidating. Not everybody’s – especially men of a certain age, whatever, might not want to go out drinking… So you can do social nights, you’re going to get some people in, you’re going to get some people out… You can do an activity night, where everybody’s downloading software, and running it, or what have you. There’s perhaps more work for their organizer in those rounds.

And in general, it seems like, while speakers can sometimes be hard to find, there is usually somebody that wants to promote something that they’re doing… And so lots of meetups will engage remote speakers at times, because that way they don’t have to pay somebody to travel if they’re from out of the area. But the good ones are mixing it up, and having a local person speak, and then have a remote speaker as well.

[20:12] And so now you’re deciding to do this regional - is it conferences? They’re actually conferences? Or these are meetups? What are these things that you’re going to do this fall?

They’re single day, single track conferences. We’re aiming for about 60 people. And that’s the sort of – that’s the size where you can actually meet everybody in the room. And we’re also able to – we’re not going to be in beige boxes, we’re not going to be in hotel ballrooms… We’re going to be in Chicago, we’ve got a loft, like a warehouse space, with soaring ceilings… In Atlanta it’s a small black box theater, and in new Orleans we’re in a – I should really look up how old this place is, but it’s called the Marigny Opera House. It used to be the Holy Trinity Church, and it is just every bit a new Orleans church, which is… It’s a white brick building, but it looks really gritty and dirty on the outside… You get inside and it’s just fantastic, and I’m super-excited about that venue in particular. In Portland we’ve got an industrial chic warehouse space. And we’re bringing projector PA stage backdrops… Pretty much the entire conference is going to go into the back of the vehicle and drive from city to city. So I’ve got 7,500 miles of driving ahead of me in the next two months, and with the goal of – we could go into any space. If you’ve got power, seats and bathrooms, we’ll be able to put on an event. That was the thought.

What’s the what’s the venue for Austin? That’s your last leg, is Austin. That’s my stomping grounds, you know that, right? I’m in Austin now.

I do know that. And my theater – somebody came in and sniped my venue out from underneath me.

You’re homeless…?

I mean, I am –

Well, you know what I mean.

…I’m venueless in Austin at the moment.

Venueless, yeah. Better word.

I’m experiencing –

Maybe we can help you.

I’m experiencing venuelessness… So I’ve been working with the folks at Alamo Drafthouse, so there’s possibility there… I don’t want to shade anybody, but there’s a well-known incubator space there that I haven’t had any response from; I reached out there… But yeah, I’m unfazed. Our demands on space is not that large that –

And guess who else is going to be there, Jerod? Landon Gray. Does that name ring a bell to you?

No.

Think back to “An aberrant generation of programmers.”

Oh, Landon.

Yeah, Landon. He was the young buck… I don’t know what was the –

Our Gen Z representative.

Yeah.

Yes, with us…

Landon is speaking there, according to the site.

That’s cool.

Sure is. And you know where I’m –

How do you know Landon?

Did you ask how I know him?

Well, I assume he was in Austin, but yeah - how do you know him?

I know him from a conference. I went to [unintelligible 00:23:25.09] Ruby two years ago in Nashville, and met Landon. He was working at Test Double at the time. And then - I forget if it was… It must’ve been last year. I traveled, and we did a traveling meetup in New York city, and he lives in upstate New York. And so he came down and spoke at our event in New York city. Yeah, he and I have been bouncing off with one another ever since.

Is he an Austinite, or…?

No, he’s upstate New York.

Okay, so he’s coming down then for that. Cool.

[24:00] And the point of doing these conferences is to put them in people’s backyards, so that there’s not the expensive – we’ve been working with Ruby Central to do the designs, both digital and in physical space for RailsConf and RubyConf, and the feedback that we constantly get is “This is great, but I’ve got to take an entire week off work. I’ve got to spend a week in a hotel in a major metro, and all those things are expensive.” And what is also true is that you can’t really get that experience without doing it that way, where you bring all the people to – like, you bring a bunch of the community together, you get 800 people together in the same space. That’s hard to do in any other alignment.

But there was a gap that we saw, which was “What if you didn’t have to take a plane, what if you didn’t have to drive eight hours, or whatever? What if there was no hotel involved? And what if the ticket, instead of being 300 per day, was a hundred dollars?” And that was what we were trying to solve for. So we spoke with the folks at Cisco, and they saw what we were trying to do, and so we teamed up with them. They’re our foundational sponsor. They’re sponsoring the entire series of events we’re doing this year. And honestly, I couldn’t have done that without them.

Yeah, for sure. When I first heard about this, if I’m being honest with you, I was like “Gosh, man… Events are so hard. Smaller events have to be even harder. How do the economics work, and how do you get motivated by it?” You don’t have to share the numbers behind the scenes necessarily, but what is it that makes you want to do this? Like, what makes this hard – it seems like a hard journey to me. What makes this hard journey worth it to you?

Events have always been a – I have always had events, going back all the way to 2008. I submitted a talk to Scotland on Rails, and I pitched a talk on geospatial searching in Rails, which was using [unintelligible 00:26:17.18] at the time… And got accepted. I’d never done a talk before… And it bombed. It bombed so hard. Of a 30-minute talk, the first 15 minutes was mostly me on stage, sweating, because we were trying to figure out how to get my computer to work with a WiFi signal… A classic thing that would only happen in an event. You live and learn, and I’ve never gotten caught by that again. But what also happened was I was waiting in the registration line, and I’m watching Ellen Francis, Grant Paul just completely swamped by this rush of people who were trying to get through the registration process. And so I jumped behind the table, and I’m like “I can handle T-shirts. Tell me your size, I’ll get you the shirt size that you need after you get registered, and whatnot.” And so that was – I’ve shared the story a number of times, and also with them, but I was like “Man, if these guys can do it, I could do this as well.”

We’ve done Madison Ruby for about 10 instances, including last year, and at the last one I was just like “This is really risky. Our expenses are significant, and what would make them easier to pull off would be if we can lower the risk profile.” And so through the sponsorship that we got from Cisco, we were able to cover all of our venues, and cover some of our expenses… And then working with our local sponsors, if we are able to reach our sponsorship goals, we have everything covered, and then any of the ticket sales is on top of that.

[28:17] We haven’t hit all of our sponsorship goals yet, but I’m positive that we’ll get pretty close. And if people don’t have to plan a trip, they can buy a ticket the night before, and still make the show. And so we’re going to cities where there are significant Ruby user groups, there is a significant population… And we’ve tried to lower the risk at every stage, so that we’re not left holding the bag.

When we ran our first Madison Ruby, I personally lost $9,000. I’m going to adjust that to say “My wife and I, who’s sitting in the other room right now, lost $9,000.”

[unintelligible 00:29:01.27]

Yeah. We eventually figured that out and got it back… That was also the only time I ever wound up on the front page of Hacker News… Because we cut the ticket price from 495 down to 250, and said “We’re refunding everybody who bought at that 495 price. We’re refunding you down to 250”, and got a bunch of press out of it. And we still lost money, but I think it would have been even worse having not done that.

Was it you reduced the price because you wanted to get more – or because it was selling less, to make it more attractive? And then you felt bad charging some people higher, and then some people lower, kind of thing?

That’s right. It felt like the right thing to do.

Yeah. Because usually it’s early bird, you buy early, you get the better price, not you get the worst price.

Right.

Yeah. You don’t want to take the people who supported you early and say “Sorry, this shaft is for you.”

Yes. Yes. That’s not what Budweiser’s tagline is…

It’s close, but it’s not –

“The shaft’s for you”?

Yeah, the shaft is not for you, okay? Don’t, take it. Well, maybe in an attempt to shed some light on your sponsorship opportunities for XO Ruby, where in the world can people go and find out how to sponsor this thing and learn about it? I know xoruby.com, but is there a sponsor page? I couldn’t find one.

That is an excellent point, Adam…

I’m so sorry…

[laughs]

No, no, no, by the time this airs, there will be – if you go to the footer, there’s a promo kit. If you go to that link, there are some sponsorship information –

Some stuff in there. Okay, I can see that.

And also, if anybody’s just interested, you can go to /sponsor and it will take you there. You know what? I I’m feeling better about myself. If you – in the top nav there is a link to the Firestarter, which is a campaign to support this. It includes sponsorship at the event and city level, but also if you wanted to –

Okay. Oh, I see this now. Yes, yes…

…if you want to buy a ticket, or buy us a tank of gas, or tacos, or however you want to support… Like, if we’re not going to be coming where you are and you still want to support, just go to the Firestarter page on xoruby.com and all the details are there.

That actually is a proper page to send people to. If you scroll a couple of times, listeners, if you’re going there, scroll a little bit past some of the things that are important, but… If you want to go right to the sponsor details, this is actually really cool. You’ve got like one leg sponsor, where somebody can sponsor a leg… Or if you want, like you said, tacos, or whatever… Or one of each. I thought that was kind of cool, where you spend 600 bucks and you get one ticket for each event. Maybe you go on the road with you, or whatever. I don’t know. This is kind of cool, I like this.

Yeah, I think the truth of our work days and the events that we put on is that we can kind of make them look however we want. Like, there’s going to be lines, but you don’t always have to stay within the lines.

Yeah.

[32:11] This is quite literally me putting – somebody suggested I was playing Johnny Appleseed, going around planting a bunch of trees… And if we go to Atlanta, and we’re working with the local organizers in Atlanta, and if they say “Hey, this turned out really well.” “Would you mind if we do this next year?”, they’re like “No, here’s a playbook. You can do this next year.”

So if somebody takes that playbook and runs with their own conference in Atlanta next year, we’ll go somewhere else. We’ve already spoken with folks in Boston, Denver and Kansas City, that are asking “Would you bring an XO Ruby conference here?” And the answer is let’s get the first three out of the way first, and then let’s talk. But there’s nothing stopping us from doing that, and we have a pretty good understanding of how to put these on.

Yeah. Does that mean that – I’m on the Madison Ruby website now… Sorry, if I’m pulling up some more things here, but… I’m noticing that it doesn’t say 2025 on this webpage I’m on now, MadisonRuby.com.

Adam, I’m already putting on six conferences this year. Do you want me to put one out in Madison to you?

I’m not suggesting that you are. What I’m asking is does that mean this is paused, so that you can do this?

Absolutely.

Okay.

This is a heavy lift, and the first year of a conference is always the hardest. Anybody who’s been to a Madison Ruby will recognize bits and pieces of what we’ve done in Madison in each of these, including some of the speakers, including some of the activities and whatnot. So I want to do something in Madison again, but honestly, it will probably be XO Ruby, rather than Madison Plus.

Does the website get a lot of traffic to Madison Ruby? Or is it just kind of like fickle whenever there’s no event really happening?

It seems like it’s fairly fickle, and on Monday, for some reason, we got 400 hits, and I have no idea why.

Yeah. Well, those 400 people did not know about XO Ruby. That was gonna be my next thing, was like “Okay, let’s tell–” I mean, because you’re famous for doing this for ten seasons, as you had said. Was it nine or ten?

Ten.

Ten. I mean, ten’s a lot, right? That’s a decade of producing a conference… So there’s gotta be some sort of brand equity there, where people are coming back to it, or there’s content that people are coming to… Leverage that. Promote XO Ruby on Madison Ruby. It’s all your company, Flagrant, so I would happily like say “We’re paused, but that doesn’t mean we’re not here. We’re elsewhere in the world”, kind of thing.

“We’ll be back…”

Yeah, “We’ll be back.” Thumbs up.

Break: [34:55]

What are some of the challenges that have come up with organizing six in a row, I guess, or… You have to organize them in parallel, but they operate in a row. I assume call for papers is probably harder, and lots of stuff’s probably harder when you have six things going on.

So yes, that is true, which is why we didn’t do a traditional CFP for this.

Okay.

I largely curated the talks for the first couple of events. If you go to the schedule, if there’s a slot where there’s not a speaker, there is a link there to sign up and say that you’d like to join… Because again, the hope is that either we or somebody else will do this again next year. And so we really want to find out where people are… So that’s part of it.

The failures cascade… Thankfully, in the first round, we actually lost our venue in Chicago once, and had to go to a backup. And while I’m extremely happy with the backup - in fact, that’s what happened with Madison Plus Ruby the first year, and we wound up with this amazing venue that we really loved… But that meant that we had to go back through and reschedule both of our events in Atlanta and New Orleans after that venue fell through.

So that is a risk in doing these sort of in series. Typically, you get into a workflow of – you know, there’s a [unintelligible 00:39:00.19] conference, and then you’re done and you get your rest. And it’s just been building for the last couple of months, and in two weeks we’ll get some relief.

So you picked this every Saturday cadence for a group of three, and then it seems like there’s some short break, and then another group of three. Thoughts behind that? Like, what – versus, you could have done it like every other week, and maybe just spread them out and relax a little bit in between… But here you have Saturday, Saturday, Saturday, and then a little break.

I should have done Sundays… Sunday, Sunday, Sunday, you know?

[laughs] Hey, you could have sold more tickets that way. Sounds like a deal.

You buy the entire seat, but you’ll only use the edge. Sorry…

[laughs] That was a good one.

I grew up going to racetracks. My dad drove stock cars… But there is a gap, you’re absolutely right. In fact, I drive from Chicago to Atlanta to New Orleans… And then Austin’s right here, but instead of going to Austin, I drive back to Wisconsin. My wife’s birthday is in that gap, and so I wanted to come home, spend some time at home. And then something that’s not even on the XO Ruby map - I’m actually going to Rocky Mountain Ruby before I start the Western leg. So I’m going to drive out to Denver. Flagrant is sponsoring Rocky Mountain Ruby. And then we’ll start the rest of the second leg after that.

Gotcha. You’re going to take a – do you make a documentary or something, like a road trip… You know, road rules, but RubyConf style, Ruby conferences, XO Ruby road rules.

I do have a little mobile camera rig, like a cage to put around my mobile camera… And I’ve been talking with some filmmakers about getting – like, even just behind the scenes stuff. If I’m driving past the largest ball of twine in the country, we’ll stop and take a picture. We’re also – DNSimple is sponsoring, and one of their mascots is a… Like, in the write-up that they have about their mascot it says that he’s always up for a road trip… And so I’m going to try and get them to send me a plushie to ride shotgun with me. But yeah, we’re going to try and do something.

We’re also working with Confreaks, trying to get them to record all these events… And if nothing else, maybe we’ll do something a little bit DIY to get them recorded if we need to.

Man, I haven’t heard the name Confreaks in a long time.

It has been a long time. So long, I was going to ask you to remind me of the person’s name. And as soon as you say it’s going to be – who runs that…?

You are probably thinking of Kobe.

Yes…

[41:56] [unintelligible 00:41:56.03] He’s at Heroku. He’s got bigger fish to fry. He worked with Cindy Backman, who has been running Confreaks for the last six, seven years, and always brings a really… Like, she sees so much. She goes to so many conferences and so many Ruby events and whatnot… She’s got an interesting perspective on the history of the Ruby community. And actually has found herself on stage at RubyConf, and… Yeah, and then not only does she record the talks, but she goes through and edits all the talks as well.

It’s a lot of work. So much work.

Yeah.

Wow… Actually, the last time I think we saw – is it Kobe? Is that right?

Mm-hm.

Last time we saw Kobe was at Keep Ruby Weird, first edition here in Austin, Jerod. Remember that? 2014.

I remember the event, I don’t remember that being the last time –

Kobe was in the rafters with us, recording.

I remember that part, but didn’t we see Kobe at like OSCON as well later?

Maybe…

Maybe. Who knows?

It may be.

It’s fuzzy back there in the history books…

It’s fuzzy back there… [laughs]

But I do remember Keep Ruby Weird at Austin, because that was the first time that we met, wasn’t it, Adam?

I think so, man. Yeah.

And that was at the Alamo Draft House, Jim. So…

Right on.

That was a good venue. Good venue.

Yeah. I’m talking with – I wanted Caleb to come speak at the Austin event. He’s up in Denver. He’s not going to make it down… He has a conflict. But I’ve also got a call in to Terrence as well, so…

Oh, yeah. Terrence Lee could help out, for sure.

Yeah.

If you mean Terrence Lee. I assume you mean Terrence Lee.

Blue hat, of course.

Yes, the blue hat. Famous for the Blue Hat. Was it Tar Heels? North Carolina Tar Heels? Isn’t that what it is? Or is it just a blue hat?

I think it’s just a blue hat.

Okay. I wasn’t sure. I thought it was the Tar Heels, but… That’s cool.

It could be.

I actually spoke to him earlier this year. We had a sponsorship with Heroku and I got a chance to catch up with him again… And then he gave me this number, and I’ve been too busy to reach out to him since then… So Terrence, you’re on my list, man. I’m going to reach out. Because he’s like “Hey, you’re in Austin, dude. We need to hang out.”

You do. And perhaps you could do that October 25th.

You know, I’m going to come.

You’re going to make it?

I don’t see any reason why I can’t make it. Let’s see, what day of the week is it? We already did – Saturday, right?

Yeah, man. Saturday.

We established the joke already?

Yes, it’s not Sunday.

It’s well established.

There’s nothing –

Saturday. Saturday, Saturday.

Yeah. There’s nothing on my calendar for that day.

That’s not true…

So you have zero excuses.

Let me enable my wife’s calendar now.

Oh, he’s trying to find one…

He’s trying to find any excuse not to –

He is. He’s trying to back out, live on the air here.

We do have a YMCA parents night out on the calendar that day…

Well, you could still go to that later.

Yeah. This is nine to five. That’s later.

Yeah. That’s your evening.

And I think that means that we would have no kids, which is great, because the kids go to YMCA and have fun, and then we can go somewhere else.

Oh, there you go.

So maybe she’s trying to take me on a date.

Go to the after party. Is there an after party or anything?

The thing about after parties is that they cost money. [laughter]

Okay. Nine to five. I see what kind of [unintelligible 00:45:16.04]

Yeah. Add a hundred-dollar ticket… Like, what has happened in the past is – once you get people together, plans form, and people wind up in places together. But we’re not planning an after party, but we do suspect that people are going to gather afterwards.

Yeah, I’ve got some ideas for you. We should talk. At least here in Austin. That’s about it. Some venues, and some thoughts… Just whatever. If I can be helpful, I’ll be helpful. And if I can make it, I will for sure make it, for sure.

This is the thing – and to your point about putting the opportunity to show interest in sponsoring… When you give people an explicit direction as to how they could help, they can see that.

[46:04] So if you want to speak, reach out. Let’s talk. If you want to attend – there is not yet, but by the time this airs, there will be a volunteer link as well. We’re going to overstaff with volunteers. And so if you wanted to come to the event and you want to give up an hour or two at the beginning or end of the conference to volunteer, we’ll let you in for free. We’ve always done that with Madison Ruby, and there are people that came into the community that way, that had that opportunity, that now work at Square, and Coinbase.

That’s cool. Yeah.

And so what people most often need is an in. They need somebody to take a chance.

Break: [46:51]

You made me think about something, since you’ve been running these events so long and you have that thing that you do, so to speak, the way you run it… Is there anything in particular that you do, that you feel like makes an event - whether it’s Madison Plus Ruby, or if it’s XO Ruby, or whatever you’re doing, what are some things that you try to always do as like a DNA thing for your events?

So that’s an excellent question. We always try and get people into conversations with other people at the conference. That sort of naturally happens at a hallway track. If you’re going to your first time conference – this happened to me back in… You know, I got sent to a .NET conference out in Vegas, and I methodically went to talks that I thought could help my company, my career, whatever. And what I understand now is that it’s the people; that’s the benefit, that’s the value. You can get connected to people that are going to help you at work, you can get connected to people who you could potentially hire for your job, you can get connected to people that are going to wind up driving in a car down to Future of Web Apps, and fanboying over somebody else in the car… Like –

I’m telling you… It was Obie . I couldn’t help it. He was the coolest. He still is the coolest.

You mentioned Stephen Bristol in that call, or in that conversation earlier…

Oh my gosh, yeah.

…and that was a lesson that I learned from him, is we would walk around at a conference and he would always find a wallflower or somebody who wasn’t doing anything, and he would just bring them into the fold.

Yes… And he wouldn’t let you go. He grabbed you – not physically. I mean, sometimes physically. But he’s like a tractor beam. “Get over here… Get into this conversation. Don’t you be isolated over there.” He would force you out of your shell. He really would. I know he did it to me.

[50:04] In the best way. I was going to say, then you realize that “Oh, that’s why I’m here.” Like, he did that to me.

Yeah.

And so that is another thing that I – just try to always make sure that if there are people who seem like they’re lost, or seem like they don’t know what to do, make an introduction. I can’t – especially as a host, I can’t sit there and talk with everybody all day long, but I can connect them with somebody who’s going to make sure that they’re seen after, and introduced to people, and have a proper conference experience.

Another thing that I think is inherent in the way that we’ve done things is I will always look for people who have never spoken before. I remember Nell Shamrell gave her first talk at Madison Ruby, I think in 2012. And there was something about Nell that caused me to want to do that. But she had never spoken before, so I didn’t have anything necessarily to base that on, other than she was a great person… And it turns out she had a drama background, and she just absolutely delivered her talk, and probably the best talk of that conference.

And so even at RailsConf this year, the last RailsConf, I had somebody come up to our booth and I was like “Do you want to speak?” And she’s like “You know, you’re not the first person to ask me that.” So that was Tia. She’s going to wind up speaking in Austin as well.

So always just trying to – try to find people that think that there is an explicit rule set that they have to play by, and have to either wait their turn, or wait for permission, or what have you, and say “Hey, can I take you to the front of the line? You don’t actually have to wait for anybody. You can just do it.”

One of those things with getting everybody together is we are not catering the conference. We are strategically getting venues that are surrounded by good restaurants, and we’re giving everybody $25 to go out and grab lunch. So it’s a little bit of an adventure…

So you spend $100 and you get $25 back to go eat lunch?

That is a heck of a deal, if you ask me…

That is an awesome deal. I love that deal.

And that is something that we did for Madison. We had the luxury of being downtown and having really fantastic restaurants around. But the other thing is, it doesn’t matter how good you are, or how good your catering staff is; it’s hard to serve 100 great lunches to people, all at the same time.

It is.

Add on top of that food sensitivities, and concerns of that nature, whether your preference is vegetarian, vegan, whatever… It’s hard for me to serve all those people in that way.

Yeah, one thing that Alan and Stephen did - I keep seeing their names; I miss those guys so much. Obviously, I miss Stephen, but… When they did LessConf, one thing they did… And this is probably why Alan is mayor, because he went out… And if you recall this, Jim, you can share your side of the story, but… They went out to particular local venues and said “Hey, we’re going to have people here for this reason”, and they made a list of where you can go. I don’t recall if it was free or what it was… I think it might have been free, as part of the conference. But it was like, they had already set it up. You go out into that small town, into that little city, an independent [unintelligible 00:53:53.18] and you go where you want to, closest to the venue. You can walk there, you can go with the friend groups that you’ve made, you can make new friends, you can invite yourself somewhere, be invited somewhere… But they had already identified various places you can go, and it was just really easy.

[54:09] And those folks were ready for it, they weren’t bombarded… But you had selection, you got to see the city, and you got to come back to the venue and continue your conference experience like nothing happened. It seemed smooth to me. Maybe as an event planner not very smooth, but as an attendee, I thought it was super-cool, very smooth… And I got the choice of where I wanted to go, and I thought that was the best experience ever.

Yeah. In downtown Madison there is a local business community called Downtown Madison Inc, and they have gift certificates. And so we did gift certificates one year. Just give them a gift certificate and you’re covered. But there were so many people that went someplace where it wasn’t accepted, or… That value wound up getting lost. Or they would give it back – they would just give us the gift certificate back. That’s good for me, but you didn’t get the thing that you paid for as part of your deal.

Yeah.

But that experience of going out, seeing the city, finding some local hole in the wall and… I can feed you high quality salads all day long, or maybe you’d rather have a steak, or whatever… Some people – I would just kill a hot dog. I’m not fancy. And so it’s gotten to the point where people expect variety, and they have preferences that they want to hold up, and so we’d rather leave people to their preferences.

Kind of like that awesome burrito place that we found in – what was that, Adam? Vancouver?

Oh, my God…

Yeah, it led to a burrito place that Adam just… Loved… [laughs]

No… I remember it like it was literally yesterday, and it was not yesterday, obviously…

Oh, hilarious…

Oh, it was bad. It was bad.

Just some random person that we were hanging out with., and –

He was being very kind.

Yeah. “Let’s go to lunch.” And he lives there, and he’s like “Alright, I’ll take you guys to this burrito place. It’s amazing.” Or something, I don’t know. And it wasn’t that bad, but it didn’t jive with Adam at all. And so we were trying to be gracious, you know… But Adam’s not as good at acting like this tastes good. [laughs]

I left hungry, let’s just say. I left hungry.

Yeah. And with a smirk – or not a smirk. What’s the opposite of a smirk on his face?

A total frown.

A total frown. Yeah, basically. You were frowning.

I don’t want to tangent this too much further, but you knocked a hot dog, and I had some friends over a few months back…

Who knocked a hot dog?!

Yeah, who knocked a hot dog?

Well, you said “I can kill a hot dog”, like it was not –

Yeah, kill one.

Okay, okay.

No, like, knock it down, right?

Knock it down. Gotcha, gotcha.

Like just shove it down your throat.

I had hot dogs for lunch yesterday, man…

[laughs]

Well, I discovered these Wagyu hot dogs… And these Wagyu hot dogs - I’d never had Wagyu hot dogs like this ever in my life. We had some friends over for the 4th of July this year, and they brought them. It’s like a tradition for them. Like, “Sure. Sweet. I’ll cook them.” And so they brought their Wagyu hot dogs, and we got the long buns and all that stuff, and I got a Weber kettle, and I got them over a real fire, so they got all the flavor in it… And I promise you - I’ll make it for both of you one day - some of the best hot dogs I’ve ever had in my whole life. In fact, those – when I think about hot dogs that I want to have in my life, if I could eat a hot dog like that every day of my life… Or not – every time I eat a hot dog, if it was like that, that’s my example of a hot dog. It was so good. So good. Are you hungry yet, Jim?

I mean, thankfully – well, you all are… This is afternoon for you two. [unintelligible 00:57:51.22] Yeah, I just bought, probably three months ago, a Weber Smokey Mountain. And so I’ve been smoking up a storm in the backyard.

[58:01] Well, we can we can talk about that in the after show, for sure. I will talk about barbecuing with you all day long… Because it is one of my passions. So xoruby.com… This is like pretty much tomorrow you kick off. Are your bags packed?

Yeah, it’s soon.

Have you got piles of laundry that you’re washing? What is your stress level in this moment?

Stress level is pretty low. It’s gonna unfold, and it will be the thing that it is…

That’s one way to look at it.

You could always sell more tickets, you could always have more sponsors… And it’s not like we’re not still working on it, but… I’ve got backdrops, and a projector… I did a test run at my [unintelligible 00:58:47.21] community on Sunday night, just to bring everything out, put it all together, make sure that I’ve got all the connections that I need…

What was your talk about?

No, no, no, I didn’t actually do a talk. I just got everything put together. But they have a community space that is large enough to put it all together. Because it turns out, it’s like 30 feet of backdrops.

Oh, my gosh.

That’s a big one.

Yeah, don’t dry run that day one, right? Test-run that at a 55+ community where it’s safe.

This was not my first test run either, because I did – I think two weeks before I did one, and it did not go well. I’m like “I’m so glad that I don’t have 100 people sitting behind me saying “Where’s the show?”

Yeah…

You know, the one thing that does have me sweating a little bit is that I ordered the projection screen online, and it was supposed to be here on Saturday, the 23rd. And then they said, “No, it’s delayed. It’ll be there on August the 26th.” Well, it’s now August the 27th and I don’t have a screen to project on yet.

Less than a week? Or do you have more than a week?

More than one week.

Yeah, more than one week. You’ve got a week and a half… Chicago, September 6th.

Well, I mean, if it doesn’t arrive, dropship it to wherever you’re going to be at. Don’t be like “It’s only at home I can take deliveries.” Take delivery wherever you’re at.

Yeah, but you can’t change that that late in the game. It’s going to show up even later.

Nah, you can’. the next venue, though. The next event gets the screen.

You should order a backup and ship it straight to Atlanta right now.

I have found there is a not nearly as good version, but there is a version that I can get, that should be able to get here in time. But I want the good version. I want the best experience for people.

Sure. Well, if you are in and or around Chicago, Atlanta, NawLeans, as they call it down there, Portland, San Diego… And especially Austin, because I hear one Adam Stacoviak will be in attendance…

I will be in attendance. I’ll be there.

…it’s not too late to get in on it, right? You’re selling tickets right up to the day, I suppose, and…

Absolutely. The other thing too is if you’re in between those cities, I’d love to stop and have coffee, or whatever.

Oh, cool.

Part of making the movie or making the documentary is we want to find people along the way. I’ve got one stop already in Nashville, and then I’m talking to Travis Dockter, who’s planning Blastoff Rails for next year in Santa Fe, New Mexico, about stopping there as well.

Put your route up on the website. Put your route so that people can see where you’ll be generally speaking. That’d be cool.

I think, again, in that promo kit, which is in the footer of the xoruby.com, I think there is a link… But we’ll make it more prominent and do a specific call on the blog.

Yeah, that’d be cool. “Here’s where we’ll be, and when.”

[01:01:47.12] I would almost encourage – I’m trying feverishly to see if you’ll correct me, but… If there’s already an Instagram. Because I was gonna say, just start a brand new Instagram just for this, or something like that. Anything to kind of like document as you go… Because that thing will catch steam, you know? Or even LinkedIn, I suppose. Our version of Instagram is probably LinkedIn, right?

Yeah, I was trying to avoid –

[laughs] [unintelligible 01:02:07.01]

As I said it, I was like “Oh, that’s kind of sad…”

“Our version of Instagram is LinkedIn…”

Well, I think less of our community is – they’re probably on Instagram, but not for that kind of content, maybe. I don’t know. I was just thinking it might be better suited for LinkedIn…

The problem with our community, with software developers, is that we’re scattered to the four winds. That’s the problem.

We sure are. There is no home anymore.

There is no home for anybody anymore. Like, there is not one place where you can go and find everybody… And that is absolutely a lesson that I knew going in, but I’m just feeling so hard. I don’t necessarily know how to solve it. We are not creating our own asynchronous communication space. We’re partnered with Ruby Central and we’re using their Slack… So if you buy a ticket to the conference, you get added in Slack. You could always join the Ruby Central Slack from their site, but… We didn’t want to create further – we don’t want to create our own Discord and have yet another walled garden that people can’t get access to.

Or even temporary. Like, I’ve been to so many conferences over the years where you have a temporary place, and all the connection you’re trying to make is stuck in that past. That’s a great choice to use Ruby Central’s Slack, and just double up… Because - like, put them where the community’s at, and not where it’s temporary. That makes a lot of sense.

Yeah. We did that with Madison Ruby, and we will be moving everybody over to that Ruby Central community Slack instead… Giving people the opportunity to move over there. We’re not going to force people if they don’t want to, but…

How in the world do they afford that Slack?

I think it’s free. I think it’s the free version.

Oh man, I’ve got to know who they know. Well, not anymore, because we use Zulip, and it’s so much better, by the way…

I was gonna say, they probably just lose their history like we used to.

Yeah, that’s probably the case. Anyways, Zulip. Hey, Zulip is cool. We love Zulip.

Zulip is cool. Another place you can go… [laughter] It’s one more app. That’s the challenge, is it’s just [unintelligible 01:04:08.23]

That is true.

I did not join after we started talking… But that’s the problem, I’d rather – here’s the thing… Early Twitter days, everybody was in one spot, and there weren’t alternatives, there weren’t other people doing the same thing. Now there are too many. You’ve got BlueSky, Mastodon, Instagram, Threads, LinkedIn, X…

Wow.

How do you find people? And that’s on top of like individual Discords, and Zulips, and Slacks…

Yeah. Well, I did with Discord what you do with Zulip. Anytime somebody says “Join my Discord”, I’m like “Nope.” I’m just not going to do this Discord. I just decided to nope out of all Discords. I’m not going to do it.

I mean, I have an account, and I’m [unintelligible 01:04:57.21] but it’s such – I don’t even understand how to use it. I feel like I’m old, or something. I’m like “How does this work?”

Discord just feels like it’s more about them than me.

Discord, I definitely struggle with. I think I have about 72 Discord accounts that don’t seem connected to any other thing that I know or do… And every time I join, it’s like “Oh, you’re a new person.” I’m like “No, I’m the same person.”

Yeah, their join process is horrible.

It’s like the old days XKCD about the protocols, because right now I’m about to say “What we need is one new place, where we’re all going to go, and then we’ll be happy.”

And that will be the place that no one goes. [laughter]

That’s LinkedIn?

Yeah, that’s what Adam just said. LinkedIn is–

Maybe. Maybe. I mean, I like LinkedIn.

It’s Instagram for olds? Is that what you’re saying, Adam?

[01:05:51.19] No, I think Instagram is for everybody. I just thought that maybe more people would gravitate towards LinkedIn. I know I’m – I probably check LinkedIn several times a week, whereas Instagram, I’m on there maybe, maybe once. And it’s just really just to look at my wife sharing our life to our friends, on Instagram, because I like the way she shares it. I just want to see what she says, and look at the pictures she takes… And I saw them in the moment, and I saw them in the camera, because she’s like “Hey, look at this picture”, but somehow seeing the story version of it later on from the publisher, my wife, is very cool to me. So I pretty much go to Instagram to read DMs from her, because she sends me things that she finds on there…

Same. Same.

And watch what she shares on there about our life. That’s the only reason I go to Instagram.

Right. To look at her pictures. Yeah.

Yeah, that’s it. That’s Instagram for me. So I mean, there you go. But…

I’ve definitely taken the tact of trying to not add another protocol, but just drop them. So I’ve never even wound up on Threads..

Yeah, same. I was like “No, I don’t think so, man… Is this a version of Facebook I want to be involved in?” Threads just never made sense to me.

Right. I’ve given Zuck enough in my life, you know…

It was an also ran. It was an also ran that just didn’t run. I don’t know. There’s a lot of people there…

I was going to say…

There’s people there, but they’re not real people, I don’t think…

A bunch of bots…

No offense to those people, but they’re just like –

Kara Swisher is going to be upset with you, Jerod.

Yes, she might.

Oh, gosh…

But you know, she’s cross posting to everywhere. Come on.

True.

That’s what people with big follower accounts do, is they just – every new thing, they’re on it, because they want to get that follower count up. And then they just cross-post the same crap across all of it.

I feel seen… [laughter] I’ve been cross-posting stuff for X [unintelligible 01:07:31.25] lately, and… Yeah, you’re not lying.

No. I mean, what else are you going to do? You want to go where the people are, and now the people are in seven different places… And so you’re just like “Well, I guess we’ll post to seven different places… But we’re not going to be happy about it.” So no allegiances anymore.

I know I asked you what was your motivation, but I think maybe a different version of that is… What is success of this for you? Like, when you’re done with the roadshow, it’s December, maybe you’re sitting on your couch and you’re getting ready for Christmas and you’re reflecting on your year, and you’re like “Man… his is what happened with XO Ruby”, and you’re recounting in your brain what happened… What is success? What would that be for you?

There’s a dirty secret in all of this, which is I have run out of – we haven’t heard from my wife in the other room this entire thing, but this might be the one thing… I have run out of clients under this roof, that I need to go out and meet people. And so part of this is a sales trip, right? Like, this is me, going out on the road, meeting a bunch of people in new locations, and looking for design and development work for Flagrant… So that is one goal.

But the bigger goal would be for people to – there have been people who’ve had whole careers over the last five years that haven’t had access to local conferences. That don’t understand that you can talk to somebody and get access to opportunities that they didn’t know existed, because they weren’t in the same physical space with one another. So if I’m sitting there and I find out “Hey, I just got a new job from somebody that I met at XO Ruby”, like, that’s a huge win.

I just talked to somebody right before this call, and they said “I’ve been on the market for nine months, and I don’t know what I’m doing wrong… What do you recommend?” And I sent them a ticket to Atlanta. So they’re going to show up in Atlanta, and hopefully they’ll walk away with a connection that leads to work, or some opportunity that is beneficial to them.

[01:09:50.05] That’s really the goal, is to get people on stage that have never spoken before. Get people to understand that there is a unique serendipity that is only available if you show up. I’ve got a friend and mentor, Martin Atkins. He’s a musician. He always says “Awesome stuff happens when you do stuff. Nothing happens when you don’t.” And if you never leave the house, you’re never going to meet new people.

That’s good.

You’re never going to find opportunity. It doesn’t just show up at your door and say “Hey, do you want a job?” That doesn’t happen. There was a time where that happened, in the 2010s… But that is no longer the case. And so you’ve got to go out, you’ve got to meet a lot of people, because not all of them are going to… You’re not going to connect with all of them. But if you meet enough people, you’re going to find enough of your people that something works out. Whatever that is for you. Maybe it’s a job, maybe it’s an opportunity to learn woodworking from somebody that does woodworking. But that ability to connect with other humans is so important.

Can we unpack that? The “Run out of clients under this roof” comment. Can we unpack that a bit more? Can you go [unintelligible 01:11:18.22]

Yeah. I mean, I’ve been doing consulting since 2011. I’ve been either an owner, or part owner, going back to 2007. My wife is one of my clients, and she’s in the other room. I’ve reached the limit of what I can sell her on… And so now I’ve got to go out in the real world and get other clients for us to consult. She runs a software as a service, it’s successful, and she only has a certain amount of needs.

So I’ve got to go out and find people that are looking for the skills that me and my team have. And at this point, we’re largely doing Rails and Hotwire. We’ve got some React and TypeScript folks… But we’re about half and half design and development. That is product design, UX, UI, all the way up to branding and illustration. Yeah, I mean, it’s a tough market for everybody, and there’s not a single consultancy owner that I have talked to that isn’t struggling, or laying people off, or what have you.

Is this a ChatGPT thing of three years ago thing? Like, a decline since then? I know we all went through the pandemic and there’s lots of crazy change up, and then it was a whole different world, and then it was back down to the new old world again kind of thing, where it was back the way it was… Has this been a trend for a decade, or three years, or what’s the trend?

Yeah, I think the – I mean, I don’t think that we have a unique story. We grew during the pandemic, we were up to almost 20 people, we’re down to 10 right now… And we are keeping our nose above water. But part of it is, unless you’re going out and meeting new people, it’s hard to get people to find you, and it’s even harder to get them to trust you. So it’s really - all of the new work that we’ve had this year, the bulk of it were people that we met 10 years ago, that already trust us. The other brand new work that we’ve gotten has been referrals from people who trust us. And so it is really – if you spend any amount of time around me, you will likely hear this comment, but it was something that was shared in 2011 when we started my first consultancy… Somebody shared this with me and they said “It’s not what you know, it’s not who you know, it’s who knows you.” And I’ve come to learn that that means who knows that you are the person that’s going to show up? Who knows that you are capable of solving their problem? Who knows what your values are, and who knows that they can trust you?

[01:14:21.16] That’s the part of meeting a lot of people that – it’s not that I’m out there doing a little jig so that everybody knows that I can do the jig. You just – you’ve got to show up. And after a while, people just know that “That’s Jim. He’s going to show up. If you’ve got a problem with Rails, or if you’re doing Ruby in Madison, you should talk to Jim. If you want some really great design work done, you should talk to Kelly… But talk to Jim. He’ll get you connected.”

That makes sense. And so your world is shrinking because of the – I would say probably… You run the event, but is the lack of getting out there and meeting people outside of the Madison bubble, is kind of what I hear you saying. It’s like, you want to go beyond Madison.

I think that’s fair…

Because you’ve got pretty good touch points in Madison, right? Madison Ruby has got to be giving you something…

For sure. It is also only once a year, and so we wanted to do something that… You know, the original plan was to do 12 of these every year, and it would have been a cycle that just kept going. So it was constantly meeting new people. And we decided to settle for six, and then just focus on the fall. But if these turn out well, we do have plans to do more of them. And ideally, if folks get involved and they’re successful, and they just want to keep running with it, we would be happy to do that, too. Because I would love to just go to events, rather than throw them.

Yeah, putting on an event is tough business. I’ve resisted my entire life… And Jerod, do you want to share? Recently, we did a live show. I mean, Jerod did all that, pretty much. I didn’t do anything besides show up and smile, and upset a few people, really…

What do you want me to share about it? There’s lots of –

Just the fact that we did it.

Yeah, we did.

You know, the fact that we haven’t done anything like that, but we did something… It was the smallest version of what we could do, basically.

Yeah, totally. It’s not like we did six of them in a row, we just did one. We’re mere pikers, Jim.

How many people?

Oh, 50.

That’s good. I mean, that’s a great audience. What sort of venue did you do it in?

We did it at the Oriental Theater in Denver. So we picked the city first, and then we asked around about locations, and then found a location that was affordable and seemed like it was pretty cool… And it was both those things, so we kind of got lucky, I guess, in that way.

Yeah.

They were great to work with, which can always be a variable as well… And we kept it as simple as we could possibly keep it. Even our meetup the night before was completely just like “Here’s where we’re going to be. Come there if you want to.” That kind of thing.

Yeah.

So it was just low stress for that reason. And then obviously, putting the show on is something that we normally do twice a week anyways, just not on stage. So a little bit extra, but not too much.

Right on. Well received? Everything went well?

I think so. There’s obviously places where – as the self-critical people that we are, there’s plenty to improve. But overall, I think everybody was pretty happy about it, and the show turned out pretty well. What do you think, Adam?

I think when we did our consensus recently we said the only thing we would have changed was have onstage monitors. And I think that’s a win, because if all you need is onstage monitors so you can hear yourself better in the mic as you interview somebody… Because we interviewed Nora Jones; she founded Jelly, it was acquired by PagerDuty… We have a podcast about it via this live show, you can go listen to that, but… We were talking into the microphones, but we didn’t have in-ear monitors, and we didn’t have onstage monitors… So she had to hear us for real. The audience could hear us loud, because they heard us through the loudspeaker system… But she couldn’t hear us very well, and we couldn’t hear her as well as you would probably want to. I could still hear her, but it was a struggle in a couple of cases where maybe the venue was louder.

[01:18:28.01] Just something may have happened where it was like you couldn’t hear us as well, and she’d say, “Huh?” or “What did you say?” And that wouldn’t have happened if we had onstage monitors or even in-ear monitors. So I feel like that’s a major win, if all we walk away with is “Oh, onstage monitors.” Everything else went pretty smooth. There was no real hiccups that you couldn’t solve in the moment.

Yeah, that’s a huge victory. So you’re going to do 12 next year?

We did talk about doing several. Yeah, we did talk about more.

Definitely more. Maybe not more than one a year… Maybe more than that. But I think we do want to do it again, I can tell you that much.

We haven’t circled back on it. I’ve kind of walked away bullish, honestly… I don’t think we should do more than four. Maybe two or three in a year would be cool. Definitely not one. One’s not enough. I feel like a couple.

I don’t know, one is special, because it’s only one of the year, so you better get to it. Whereas six in eight weeks, or whatever it is…

Here’s the thing - the plan from the beginning was for me to drive far enough that – somebody from Chicago is not going to drive to Atlanta, let alone the rest of the cities. And so it’s local to Chicago, and there’s enough people there to support that they get one a year.

Right.

And Atlanta gets one a year. And maybe we decide to – rather than do San Diego, we do Denver next year. Who knows?

I like that idea. See?

So now you’re talking about going on tour.

I’m already on tour.

Well, yeah, but you’re talking about us going on tour. Or you’re thinking about yourself and we’re thinking about ourselves… [laughter]

Yeah, that’s true. Yeah, yeah. We’re talking about us now, Jim…!

I just thought maybe we’d go to like somewhere else, and just do another one. But you never know. I can get talked into more…

I’m down for more no matter what, in terms of like doing it again. Does it have to be six or ten a year? Absolutely not. I don’t think I would want to do six. But I kind of want to do more than one, not because I want to do more, but because I think it’s nice to get out a couple – like, I don’t know about you, but in my life I kind of have like times when it makes sense to rejuvenate by traveling somewhere with people I want to be around, and all that kind of stuff. And so I feel like that reconnection is good for everyone… And best case, it’s a regroup of our team; even better case, everyone else gets to enjoy it, too. I feel like that’s what I liked about it.

My favorite moments - and this is totally going TMI, Jim, and I’m sorry, but my favorite moment was really the thing itself, but bringing us together in the same place. Even Fogo de Chão, and like getting to sit down and eat together… To me, that was cool. Two times a year would be perfect. One - not perfect. Three - maybe too much.

[laughs] You talked me into [unintelligible 01:21:30.02]

Maybe. Maybe too much.

Now we’re negotiating here.

Jerod, do you find that travel rejuvenates you?

I guess it depends on the type of travel.

[unintelligible 01:21:40.05] company.

[01:21:47.24] Yes. I like traveling, so I’m not against the travel part. I don’t mind road trips. For me it’s a lot more complication than is necessary. So it’s like “Is it worth it?” So I think once a year it’s really worth it. I think twice maybe it is. But six in eight weeks - Jim, you’re crazy, man… [laughs]

Nah, it’s just two trips.

[laughs] Oh, I’m sure you have all kinds of ways you tell yourself… I appreciate the gumption, the ambition and the drive. I think that there’s people that do that. They’re usually younger than all of us. They go out on tour, and they’re gone for six weeks.

Are you saying that I’m old?

No, I said they’re usually younger than all of us… So we have reached a certain, you know, age…

I mean, I grew up – I came from a large family, didn’t have a lot of money, but we had… My family lived in Florida, and so probably six times in age five to twelve we would drive from Wisconsin down to Florida, straight through. Dad was always the only one that ever drove, and it just built that nostalgia perhaps for the road trip.

Sure.

But again, these are shorter stints, for the most part. We’ve got stops every ten hours or so… And trying to get through that in a week – sorry, you’re just listening to my thought process as to why this makes sense.

[laughs] Like I said, you can tell yourself that kind of things… I think it’s going to be cool, and I think it’s going to be a memory… I think that you should absolutely record as much as you can, and try to make some sort of a memory video or something, so that you have a takeaway at the end, whether or not anybody else wants to watch it but you and your wife or your team… Who cares, you’ll like it. And I hope lots of people come, and there’s great talks, and there’s great food, and there’s great venues… It sounds like you still have some variables up in the air, which for me would be stress… You seem like you’re very chill about it, so I’m –

So chill.

…chill about it as well.

It’s going to work out. It’s going to be what it’s going to be, right?

That’s kind of how I approached this event. And I think Adam probably would have stressed about it more than I did, and this was why I kind of kept him out of the details…

I would have.

…and I’m just like “You just get a place, and then you get a plan together, and you invite people, and then you show up and do the thing… And it’ll work out.” And it pretty much did.

But again, the support from the community has been great. We’ve got Coraline Ada Ehmke, Scott Werner in Chicago, Seth Giddens is probably going to join in New Orleans… Tenderlove is going to come down to Portland… I’ll leave out a few more names, because I haven’t gotten signoff-signoff…

Sure.

But again, Yuri is speaking in Chicago. He’s never spoken at a conference before, but reached out and he’s like “I would really like to. Here’s my talk idea”, and we’re talking through how to best pull it off… And Tia is speaking in Austin… Landon you all know in Austin… Ceci Correa in Austin… So yeah.

Well, if you put Omaha or Kansas City on your map next time around, I will be there. I’m not going to drive to Chicago, it’s eight hours. It seems like a lot. But I would definitely hop over to KC. It’s like a two and a half hour drive from here. For a RubyConf.

Tulsa?

Tulsa is kind of far. [laughs]

That’s fine.

I’m not saying I wouldn’t, but –

“Can I interest you in Tulsa…?”

…that gives me pause. Why? Is that already on your list? It has been sort of the canonical example of - I want people to say “Hey, we’ve got 30 people in Tulsa that want a conference.” The original idea for this was to go to underserved technology cities…

Yeah.

…that still have a population. Back in Hashrocket days we went to Huntsville, Alabama for a conference that Jeremy McNally ran…

I went to that as well.

We wound up playing –

Yup. At the old Grand Ole Opry.

I think we went –

Or that was Tennessee.

Yeah, that was Tennessee.

Okay. Well, it was definitely a Ruby Hoedown, but maybe it was… Did he do it in different places?

He might have. Because he also did a conference in Disney. He did Magic Ruby.

[01:26:18.07] That’s right. Magic Ruby.

So he bounced aound a little bit.

Okay. So I went to the Tennessee one, not the Alabama one.

Are you talking about Jim?

Jeremy McNally.

Jeremy. I was thinking of Jim who did Lone Star Ruby… I can’t remember his last name in this moment.

Jim Freeze.

Yeah, Jim Freeze. That’s who I was thinking. Because he did that in… Yeah, in Florida.

Yeah. One of those fun memories… We actually drove an RV from - I drove the RV - from Jacksonville, Florida. We rented an RV and piled eight of us into it, and drove to Ruby Hoedown in Huntsville. And we had a group of young people that were all sort of eclectically dressed, and we drive up to like a barbecue place… And we were just looking for a bathroom, and pile out of the video. And somebody asks T-Pope, “Are you guys in a band?” He’s like “No…” It’s like, “T-Pope, if anybody asks you if you’re in a band, you say yes.”

Yes…

[laughs]

You get free food.

The answer is always yes.

They might say, “Can you come on stage?” “Oh, dang…”

You don’t want to overplay that one, that’s right.

That’s right. “We’re late. We’ve got a gig. It’s too late, we’re on our way.” Well, that’s cool, man. I want to call one out, because a friend of mine - a friend of ours - is going to New Orleans. And if it was in Austin, I would be much more happier, because that’s where I’m going to go. I’m not going to go to New Orleans. But our friend Robert Ross from FireHydrant, who’s been a friend of mine, founded FireHydrant, and then became a closer friend by being a sponsor, and being a friend… And I just love their journey… And he’s talking about if I did it again. And I think he’s talking about the journey of Ruby with FireHydrant, and the mistakes they made, and the things he would do again, obviously, versus the things he wouldn’t do again… So I like the way Robert shares his stories, especially how it relates back to building a successful company… And so that’s what I’m personally looking forward to. Will these be recorded? I mean, because I won’t be able to see it. If Confreaks will answer your call maybe it will be recorded, right?

No, no. Confreaks has answered the call. It’s just, if we can find a way to get them the paltry sum that they’re looking for to record.

Yeah, that makes sense, too. Well, I got some ideas for you. We’ll talk in post. I’ve got some ideas for you if that doesn’t work out, for sure.

They have been great. I’ve worked with Cindy for most of – I’m trying to think… I’ve known Cindy for most of the decade, most of the past decade. Again, she is one of those people who shows up, and she always delivers, and she’ll always try and make something happen if possible… And we’re going to try and make something happen.

That’s a good deal. Well, everyone, go to xoruby.com. Fall in love, hugs and kisses, Ruby all around… And then go to the same domain /firestarter. And if you’re not going to be there and you love everything Jim has said and you resonate with how he cares about the community, and you care about supporting Flagrant, and their future, and what they’re doing, and all the ways Jim shows up - be a super-fan, buy a six ticket, buy a latte, buy some tacos, a tank of gas, whatever you can do.

I would love to see some folks from our community buy a tank of gas. That’d be kind of cool. 50 bucks. Buy a tank of gas, show some love, help Jim out on this trip here… And maybe he’ll do it again and again and again. Maybe in your city. Who knows? Jim, thanks so much, man. Thanks for having a great heart, and pouring in, and planting seeds, being the Johnny Appleseed we need in our world… And thanks for coming on the podcast. It’s been great.

Again, my pleasure, and thank you so much for helping me get the word out.