Giant Robots Smashing Into Other Giant Robots

498: RubyConf San Diego with Chelsea Kaufman and Allison McMillan

November 2nd, 2023

In this episode, the focus is on RubyConf, the upcoming conference dedicated to the Ruby programming language. They start by talking about the origin and evolution of RubyConf, highlighting its growth in attendance and its impact on the Ruby community. Chelsea details how the conference has adapted to the digital format due to the COVID-19 pandemic but points out the value of in-person connections. They are looking forward to the Community Day event, which will feature various activities to encourage community interaction and an acknowledgment of scholarships that would help more people attend.

The event will offer various programming options, workshops, and talks to cater to newcomers and seasoned professionals. There will also be some level of hands-on learning through hacking activities. The conference aims to be inclusive, offering opportunities for mentorship and growth, regardless of one's career stage.

Towards the end, the discussion shifts to Ruby Central, the organizing body behind RubyConf and RailsConf. Chelsea and Allison describe multiple avenues for community engagement, ranging from board membership to open-source contributions. They also encourage donations and corporate sponsorships. Don't miss your chance to register for RubyConf and engage with the fantastic Ruby community!

Become a Sponsor of Giant Robots!


VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Allison McMillan and Chelsea Kaufman, Board Directors, and RubyConf '23 Co-chairs. Thank you for joining me.

ALLISON: Hi, thanks for having us.

CHELSEA: Thanks for having us.

VICTORIA: Yes, I'm glad that you were able to make time to come on the show today. I understand, Allison, that you've been having very full weeks with family over the last month. Do you want to tell us a little bit more about that?

ALLISON: Yeah, it's...we have just ended what I call the gauntlet of Jewish holidays. But, basically, there are four Jewish holidays starting with Rosh Hashanah, which many folks know that's the Jewish New Year. But what a lot of folks don't know is that there are actually four holidays that are all in a row, each about a week apart. And you do different celebratory things for each of them.

And so, it's been really amazing and fun, and lots of, like, sharing our home with others and meals and seeing lots of people. But it is also exhausting. And they basically all fell on weekends this year, which was nice from sort of a scheduling perspective but was exhausting in the fact that I basically have not had a weekend in over a month. So, it was wonderful and tiring. And I am, I guess, both happy and sad that they're over now.

VICTORIA: Yeah, that does sound like a lot of quality family time, which has its pros and cons [laughs], right? So, after going through that, do you feel more rested? Or what do you feel like you need to do in order to recuperate and return to your normal energy levels after having every weekend full after that?

ALLISON: Oh, that's a great question. I've been looking at my calendar to be like, I should take a day off. I should take a break. I'm working for myself and [inaudible 02:02] entrepreneur consultant. So, I do have the flexibility to do so, but it is hard to look at my calendar and be like, yes, I will take this day off because I deserve it. But, ideally, I would take a day or multiple days off.

VICTORIA: Yes. And some of us are lucky enough to have a reason to travel for work purposes and to sneak in a little vacation and be productive [laughs] in our companies. So, I'm curious, Chelsea, if you can tell me a little bit about the option for people to come to San Diego in November and take a restful vacation by the beach and learn a little bit more about Ruby.

CHELSEA: Yeah, so RubyConf will be in San Diego this year. As a native San-dieagan, I am a bit biased, but November is a beautiful time to be in San Diego. And we're going to be at the Town and Country, which feels a little bit like we're going to be in a, like, Palm Springs resort. They just went through a major renovation.

And there's these really awesome, like, lounge areas with fire pits and just places for people to gather, which really kind of aligns itself with some of the stuff that we're planning because we're really trying to focus in on just connecting Rubyists together. So, to me, it feels like the perfect place because I think San Diego is, one, we're a little bit more low key, a little chill. And it's a great place to just gather and connect and share with people that have, you know, similar interests.

VICTORIA: Yes, I live in San Diego now, but I was from Washington, D.C., And I would come and visit my family in San Diego once a year. And they would always go on about how great it is and how beautiful, and everyone is so happy and chill. And I was like, sure, whatever. And then we [chuckles] had the opportunity to move here, and now I'm one of those people who says that [laughs]. Like, it's great, especially in November. Everywhere else is getting a little cold and fall. And San Diego has a little bit of fall, but it's still 75 degrees out. I forget what that is in Celsius. But yes, I'm also super excited.

CHELSEA: We have, like, fake fall activities that you can go do. Like, Allison, when you're talking about doing all the family activities and things like that, you know, this is when we start thinking about, oh, we need to go to, like, the pumpkin patch and apple picking and do all these things, but it's not cold or, like, fall weather at all. So, you want to get all, like, bundled up in your cute fall clothes or, like, put my kids and bundle them up in cute things. But then they're, like, sweating and trying to do [laughs] all these funny activities.

But I think that there's so many beautiful things to do here that we, like, try and do these, like, fall activities. But then we just end up at the beach and play in the sand [laughs].

VICTORIA: Yeah, I will go out in, like, shorts and a T-shirt because it's that kind of weather. And my neighbors will be wearing full puffy jackets and [laughs], like, long pants and a hat. And they're like, "You're not from around here, are you?" [laughs]. It's like, you guys are silly. But it's fun. Yeah, there's seasons, I think, you know, in November...I made a list of suggested activities for my team members since thoughtbot is sponsoring RubyConf this year. And we're going to have a couple of speakers at the event. And we'll have other thoughtboters available at our booth for people to come up and chat with us. So, I'm really thrilled to be hosting everyone.

And I made a list of, like, activities, and most of them were about where to see cool animals [laughs]. I was like, of course, there's the zoo, which is the obvious one, but then there's baby leopard sharks, and there's a season for them. I think they will still be around in November; I'm curious if you know, Chelsea, actually. And then there's, like, the safari parks, and whale watching, and the sea lions at La Jolla and, like, just a bunch of cool animals to see that I think it makes San Diego really special.

CHELSEA: I agree. The zoo, the safari park are great places to just hang out and see some really cool exhibits. Balboa Park, the museums there are amazing. Liberty Station is one of my favorite places to go; that it's an old historic naval training center that's been converted into an arts and culture area. So, they have, like, little shops. They have...there's museums. There's brew pubs. There's coffee shops. And then there's beautiful, like, grassy areas, and right by the water, it's one of my favorite places to just go and hang out.

ALLISON: This is great. I've done zero research on San Diego so far. So, just, like, I'm writing notes of what things to do and see while I'm there.

CHELSEA: Yeah, I know the San Diego Ruby group is trying to put together some, like, local events and things that people can gather and do together. I know that there was a talk about doing a taco crawl. I think if I say that on the podcast, it might actually push them to do it because there are some amazing tacos in San Diego to be had.

VICTORIA: Yes, I love that taco crawl. I'll reach out to them because I'll help put something like that together. I'm writing a blog post right now about all of these things and about all the other kind of events that are coming up in San Diego this fall. Great location, great time of year to be here. Tell me a little bit more about RubyConf specifically. And what are you all trying to do different this year than in past events?

ALLISON: There are a bunch of things that we're doing differently. Our goal this year with this RubyConf is really to sort of focus on more ways to bring the community together. I think in the last little bit so much excitement around Ruby and Ruby Central and just sort of the community in general. It's a hard time in tech. I think people need to be sort of choosier about sort of what they attend and why they're attending something. And so, we really wanted to help folks connect with each other, help folks get to know other people, help folks sort of reconnect to ways that they love Ruby and the Ruby community and being a Ruby programmer.

So, one of the things that we're doing differently is we have a three-day conference. And the way that that sort of broken down is the first day is a Community Day. And the first day is comprised of the workshops, as well as sort of this Hack Day, where people can bring their own projects.

We're going to have people there that folks can hack with, sort of open-source projects that folks can work on, all sorts of different stuff. So that people can really sort of get to know one another, work with one another, work with people that they might, you know, admire or have followed in the community for a while, and have that sort of really special experience that doesn't feel as conference-y, right? It feels a little bit more sort of organic in terms of the way that the day will flow and, the options that people have, and sort of what that day looks like.

And then following that, we have two days of sort of RubConf with talks and speakers, et cetera. And I'll let Chelsea add anything to Community Day and then also jump into some of the sort of new and different things we're doing at RubyConf.

CHELSEA: I agree with Allison in that we've really wanted to focus in on the connection side of things. But I think coming out of the last few years, out of even the last year that's been tough in the industry, just finding ways for people to connect, support, lift up each other, I think that that was something we really wanted to do. And we didn't want it to just be about going and seeing speakers. We wanted to find more ways for people to learn from each other, to connect. And so we added in quite a few of these community connection points.

So, on that first day, there's a lot of community aspects to it. We have a lot of learning happening with our workshops and also working on projects, hacking together, showing off what you're working on, connecting with people in the community. It's going to be really focused in on everyone's own skills and talents and coming together and supporting each other in where we're at in our careers, in our learning.

And then, the next couple of days will look a little bit familiar in the way that it is structured with some new aspects kind of woven in. We'll have our Community Room, where we're bringing different community groups together so that people can learn more about what is going on in the community, how they can support, how they can connect.

And in addition to seeing and learning about some of the new things happening in the Ruby community, we'll also have our Career Pathways room again, which will be a place for people to support their own careers. And that room was really set up so that it wasn't just about early career, but also about folks in their mid and senior careers, and finding the advice, finding the resources, finding the mentorship that they might need in whatever stage of their career that they're at, and figuring out how we can together as a community grow as a whole.

VICTORIA: I really appreciate the focus on community. And, for me, as managing director at thoughtbot, in deciding to invest in which conferences we want to attend and sponsor, we find more value in groups that are trying to bring people together around a common passion and purpose versus a particular product.

But I'd like to hear from each of you if you can tell me, what does the community mean to you? And I'm looking for, like, a personal story on how you've benefited or how you've engaged with the Ruby community in the past. And what makes you motivated as CEOs and founders of your own companies [laughs] to spend all this time organizing a conference?

ALLISON: Many, many, many years ago, I did a Rails Girls workshop. It was actually my first introduction into the tech community, into programming in general. And, for me, really, I did Rails Girls. I did not actually expect to like programming. But I was sort of launching a startup, and I wanted to learn more about tech and blah, blah, blah. And at the end of the day, I was, like, so energized and so excited about what I had built and what I had done.

The Ruby community in D.C., who I always think is just a group of really special individuals, was so supportive, was so wonderful, was so, like, "Here's where we co-work on Wednesdays. Come to this coffee shop. Here's how you can keep learning," just was so encouraging. You know, I went to the local Ruby meetup sort of really not knowing anything. And they were excited about, you know, newbies being there and asking questions and, you know, really sort of getting to know folks who are just starting out in their programming journey.

And really, through that, I mean, I went to my first RubyConf as a scholar. Was strongly encouraged to do a lightning talk, did a lightning talk. That's how I, you know, sort of ended up having a whole bunch of informational interviews and having conversations with folks. And really, that's how I got my first real job in tech. And so, you know, I want people that are coming into the industry now to have that same support, to have those same opportunities, to have that same encouragement.

And, for me, sort of planning RubyConf, planning these conferences, being a part of Ruby Central is really me giving back to the community that has gotten me to where I am today, right? And it's amazing, also, to just...I'm still in touch with the people that were at my table, sort of guiding and mentoring at that first Rails Girls session or the people who I met at the first-ever Ruby meetup that I went to.

I still talk to them. I'm still in touch with them. We still get together. I still ask them for, you know, advice and guidance sometimes. And sometimes, they ask me, at this point, for advice and guidance, which is fun. But yeah, it just means so much to me that I have really been able to get to where I'm at because of the support and encouragement of the community.

CHELSEA: I have a similar story. I guess over, gosh, over a decade ago, I also went to my first RailsBridge and got introduced to the community there at RailsBridge. And, you know, at the time, I wasn't in tech. I was in the theater. I come from the performing arts. I had spent a very long time executive leadership in the theater. And I got introduced to this community that was so warm and welcoming to people wanting to learn and grow. And I was so interested in how communities are built and how people connect together that I started getting more and more involved in the Ruby community here in San Diego.

And just like Allison was saying about the welcoming and warmth that she felt from the D.C. community, I felt the same way here in San Diego. Before that, you know, I had spent so many years being the only woman in a room. I had been in an industry that made me feel like my voice was not always heard. And when I walked into this room, I felt like I mattered. I felt like people wanted to hear what I had to say. And they wanted to learn from my experiences.

And in 2014, San Diego hosted RubyConf here. And at that point, my business partner and I launched our business, LEARN Academy, and it's still running strong today. But it was about creating that on-ramp for people and a launchpad into this industry where they could make a difference and they could have their voice heard. And they could be a part of a conversation, even if they hadn't been a part of that community for many, many years, that their background mattered, that their growth mattered.

And helping people find their voice at a table is something that is so important to me that I love being able to bring that into the planning of this conference, into a lot of the work that I've done with Ruby Central, with LEARN academy. And really just helping people understand that just because you don't have the traditional background, maybe you didn't start programming at the age of two, you can have a different background and a different path and still provide so much value.

And I think that that is the thing that I wanted to continue to be a part of and to make sure was a part of the conversation, that we need so many different types of people at the table. And I want to make sure that our community is responsive to that, that it's inclusive to that, that it's equitable as best we can, and just allows people to share their own experiences. And so, you know, I feel like, for me, we're, you know, almost at our 10-year mark at LEARN academy and that we were launching the company at RubyConf in 2014. To have it here again this year is so special to me.

I remember being at the conference many years ago; you know, we spend a lot of time helping companies figure out how to work with early-career developers and to create those pipelines for them so that there's career growth for them. And, you know, I remember sitting around the table and just saying, "Hey, who wants an internship? Who wants to, you know, help these early-career developers?" And everyone raised their hand, and we found some of our very first partners at that conference. And it's always been such a warm and welcoming community that has allowed me to feel like I have a voice and then allows me to help other people find theirs.

VICTORIA: Wow, thank you both for sharing that. I totally relate to that feeling of a welcoming community and just getting the sense that, like, wow, everyone who does Ruby is really nice [laughs]. And I think that you know, for me, same as Allison, starting in D.C., there were quite a few people who were involved in Women Who Code who were running Ruby meetups. And that's where I met Valerie Woolard, who I think is also coming to San Diego for RubyConf. I'm excited to see her again.

And it's interesting for me coming from that perspective and hearing that from both of you because I've also heard a viewpoint on Ruby community as being highly opinionated and causing certain amounts of consternation. So, I'm curious if you have any comments on that. If not, otherwise, I'm grateful that there are people working to bring that better community in the community that I'm more familiar with more to the forefront and making it more inclusive and open for everyone.

So, to, like, bring the question all the way back, it's like [chuckles], do you have any comments on, like, if there's a tendency for Rubyists to be really highly opinionated? Or what else can we do to make it more open and inclusive for people to join the community?

CHELSEA: I mean, I think that people are going to be opinionated about something that they care a lot about. And I think that the thing that I've noticed in the Ruby community is people love this language. They love programming in this language, and I think that there's something very powerful about that. And it does, you know, lend itself to people [laughs] having very strong opinions about what they think needs to be out there.

And, to me, it's not a matter of, like, whether we have strong opinions or not. It has more to do with whether we're listening or not. But I think it's really important for those of us who are leading to be the listeners, and that we should be there to make sure that there is space for people to be heard, whether their opinion is loud or not. And I think that there are people that are going to be louder than others; that is going to be true no matter where we go.

But I think that as long as there is intention around making sure that we are listening to even the quietest voices and that we are creating space for the quietest voices, that's where we're going to find more collaboration. But if we're only going out there and saying, "This is the way it needs to be," and we're not willing to listen to anything else, then I think that growth will stop happening because we need to listen to everyone. We need to be able to create some kind of place for people to come together and share ideas; you know, you don't get the perspectives of all these amazing people in the industry.

So, that's why I feel like, you know, I've been on the board at Ruby Central for about a year now, and the biggest thing that I feel like I can contribute is to simply listen. If I can help in any way of filtering ideas or creating connections with people because I've been putting my ear to the ground and saying, "Okay, these people are talking about this, and we're expanding here." And we just want to make sure that we're doing the best we can at being open to all different kinds of ideas and not closing anyone off.

Maybe your opinion is really strong. It doesn't mean that we should shut you down. It just means that we need to make sure that there's space for other people, too. And I think that that's the part that, you know, as someone who has always been a bit of an introvert, a bit of a wallflower, I understand how hard it is to get my voice out there. And so, I often fight for the quiet people. I think in every language and any space where it's a craft, it's something that we're creating, people get really passionate about it. And that's going to happen. And I think there's something powerful in that because there's going to be change that happens from that.

But if we're not doing our part in the listening and making sure that there isn't just one voice, that there's a collective voice, that's the part that I felt so powerful when I joined the community so many years ago was that, even though I had, you know, months of experience, my questions mattered. And as long as we hold on to that, the community will continue to grow.

But those of us at Ruby Central and some of the other organizations, if we're creating space to allow people to question, allow people to speak their opinions and listen, then I think that the industry, the community will just continue to thrive because of that. But we have to be open, and we have to be compassionate when we're doing our listening.

ALLISON: Yeah, I agree with all of that. And I would just add in safe places, in a way that we're creating sort of safe structures and safe places for folks to communicate.


Are your engineers spending too much time on DevOps and maintenance issues when you need them on new features?

We know maintaining your own servers can be costly and that it’s easy for spending creep to sneak in when your team isn’t looking.

By delegating server management, maintenance, and security to thoughtbot and our network of service partners, you can get 24x7 support from our team of experts, all for less than the cost of one in-house engineer.

Save time and money with our DevOps and Maintenance service. Find out more at:

VICTORIA: What, if you could tell me, what does Ruby really have going for it? Like what makes Ruby a good choice for tech founders or for new companies would make someone decide they want to build with Ruby?

ALLISON: First, it's a little bit about just sort of the ease of the language to jump into and to understand, right? There's a lot that you can get done very quickly with Ruby and Rails. And in addition to sort of individuals being able to work in it, there's a whole community of resources, and support, and podcasts, and tutorials, and all sorts of stuff.

I know that as an engineering leader at any company, when engineers are coming to me with, like, the desire to use a new language or try something new, part of what I look at is, if I'm going to hire, like, what would hiring look like? What does it look like for engineers to have to ramp up in this area? How long does that take? What resources are available? What sort of community am I pulling from and looking at? And that's both community in terms of sort of technical experience, expertise, years, et cetera, but also non-technical skills, right? What does the community look like in terms of some of those ideals around communication, collaboration, just sort of general pieces like that?

And so, I think that, given sort of the strength of open source, strength of community, community contributions, ways to contribute, etcetera, I think that's one of the reasons that it still makes Ruby a really strong choice for folks to build in and to work with.

VICTORIA: What type of people, what personas do you think will be the most interested in attending RubyConf? Is it all just going to be, like, senior or super Ruby developers, or what?

CHELSEA: Oh, I don't think so. I mean, this RubyConf, in particular, is great for anyone on a learning journey. We've worked really hard to make sure there's a good breadth of programming for different folks in different stages of their careers. I think that, you know, those of you that are maybe earlier on there, this is a great opportunity to meet people who are maybe even a step or two ahead of you. I think that the best mentorship that you can find is someone who is only maybe a year ahead of you because they're going to recognize where you're at and help you along the way. And I think that there's a lot of opportunities here for that.

I think that with our Community Day, the hacking that's going to be involved, like, maybe, as a new developer, you wouldn't be able to come in and, like, get your hands really dirty. But you'll get to sit next to somebody who has been through all the different stages and get to watch, and explore, and learn. I think that making those connections could be really great for anyone's career. I think that our mid-level developers, folks that are our management, there's great resources for them to connect with other developers in similar stages. There's great workshops.

Because of our focus on the community, I think that it's going to be a place where you can really connect with other Rubyists. And so, if you are at a stage in your career that you want to figure out what that next spring is, where that next ladder step is, this is a good place to see all the different options because you're going to be surrounded by people in all different stages of their careers.

And what we've, I think, said now quite a few times is so many people there are just so excited to help people continue that growth. And so, I think that no matter what stage you're in, you're going to find people there that are excited to help you along the way.

That being said, I think for our more senior, more advanced, our executive leadership, this is going to be a great place to, one, meet some really great talent, and, two, I think, learn from other folks in the industry of, like, where people are at, what we're struggling with, and how we're changing and doing things differently.

So, I really do think there's going to be a little bit of everything for people. And what I love about that is really that it gets to the core and heart of the Ruby community because we're so excited about new folks coming in that that growth continues, that you have folks like Allison who started out as a scholar and want to give back.

And then because we have folks at all those different stages, you can find people that are, you know, maybe a step or two ahead of you that are going to be able to help bring you up to that next level. So, I think it's an exciting opportunity for people to really meet new people, learn some new things, maybe find a little bit of encouragement, empowerment on where you're going to go next on your career.

VICTORIA: Yeah, absolutely. And it reminds me of an article I read while I was at RailsConf earlier this year about why we do conferences and what's the whole point. And, you know, for me, all of those things are true, like, all those values. As an executive, I'm going to meet a lot of great talent. I'm going to connect with other companies. I'm just going to get to show up and say hi to people and ask them questions in a way that's very informal. And that's so valuable to have that.

I think where I was going to go next with this was with Ruby Central, which I believe organizes both RailsConf and RubyConf. (And you can correct me if I'm wrong on that.) I'm curious if there are anything else you want to talk about with, like how the community can engage in support and how other companies could get involved with the community and show their support.

CHELSEA: I think that there's quite a few different ways for folks to get involved. We are currently recruiting board members. We just finished a round just now. But I know that in our planning, that we're likely going to bring on at least one, maybe two more, in the next six months. So, I definitely...for folks in the community that want to get involved, that is a really great place to really get involved with Ruby Central.

We also have a really strong open-source community. And we're working, oh gosh, with quite a few different companies now that are really helping to support our open-source efforts. And those are also good ways to get involved. You know, we do plan both RailsConf and RubyConf. RailsConf will be in the spring again. And, you know, it takes a village to put on a conference like this and that, you know, we also look for programming committee members to help us shape the program of the conferences. So, if you are interested in any of that, that's also another great way to get involved in the community.

We have an amazing programming committee that's helped us with RubyConf. And I'm excited to see what we do next with RailsConf. And I think that you know if you're one that's going to the conference and are saying, "Man, I wish that they would do this," or "I wish I could see that," come and talk to us because that's the best way for us to learn, that we want to hear all of those pieces. But don't be surprised if we then send you an email and say, "Hey, you want to be on our programming committee with us?"

ALLISON: I'll add that we also, through our website, we take donations. So, if you want to help monetarily, there's the option to do that on the website. And if you're a company, I mean, we're always looking for conference sponsorships. But if your company also is interested in getting involved in sort of more of a corporate sense of sponsoring or supporting Ruby Central, we are always open to those conversations. You can send an email to

VICTORIA: That's great. I have a fun question about the conference because I'm leading the event with thoughtbot since I live here. And I'm thinking about some fun swag to give away. Rank your preferences on what kind of swag you'd like to see at the thoughtbot sponsor booth: a thoughtbot-branded surfboard or, a boogie board, a bucket hat, or a pickleball paddle. Any of those interesting for you?

ALLISON: Wait, when you say surfboard, like, how am I going to get a surfboard back to D.C.?


VICTORIA: Okay. I think it's, like, kind of funny because if you win it, it's like, well, what do you do? [laughter] You got to shake it back. That sounds like maybe a boogie board.

CHELSEA: Yeah, I'm down for a boogie board.

VICTORIA: Thank you so [laughs] much for entertaining me on that one. Is there anything else that you would like to promote today?

ALLISON: We would love to see everybody at RubyConf. You can register. Check out the program speakers, et cetera, at You can learn more about Ruby Central at Those are, I think, the two things that we'd love to make sure everybody knows about.

CHELSEA: And if you're here in San Diego, come say hello.

VICTORIA: Yes, I have met up with a few random people from the internet [laughs] who have said like, "I'm in San Diego. Who should I say hi [inaudible 34:02]?" I was like, "Me, me, me," [laughter]. So, yes, I'm very happy to meet up for drinks. Chelsea, you and I will have to get together sometime soon before the conference. And I'm super excited for RubyConf. And thank you both so much for being here today.

ALLISON: Thanks for having us.

CHELSEA: Thank you.

VICTORIA: You can subscribe to the show and find notes along with a complete transcript for this episode at If you have questions or comments, email us at And you can find me on Twitter @victori_ousg.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

Thanks for listening. See you next time.


Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us.

More info on our website at Or you can email us at with any questions.

Support Giant Robots Smashing Into Other Giant Robots