Why Your Product Has Too Many Features (Ex-Atlassian Engineer Explains)
This is a speaker-led interview (Rich with an interviewer) that explores how AI could act as a lifelong personal assistant by mining journal entries and photos to surface memories and pattern-based insights. Rich emphasizes simple, focused product design and time-to-value (example: Arcade, an image/video-first demo tool for non-technical marketers with very fast onboarding). He recounts product-architecture lessons from Hipchat (acquisition by Atlassian, rewrite from Adobe AIR to web/React, XMPP backend limitations, reconnection storms, tech debt and rapid hiring), and narrates his career arc from PeopleSoft/Oracle through Atlassian to co-founding Arcade, alongside personal context (family, wife's illness, grief, photography and coffee side-hustles).
For me, it's more of a. I think the promise of AI is about truly being your assistant over your life. She could make use of that somehow.
Like a living autobiography.
Here's how I would use it. I would use it just like a journal. If I interact with it and then I mention something like, hey, you know, I write my journal. And I said, I had a really tough day with so and so today for X, Y, and Z reasons. An insight with that may be like, this happened before, or maybe, like, if it can suss out, like, some pattern, it's not giving you. It's not throwing a dashboard at you.
It's basically kind of your digital twin that you could be like, hey, what.
Happened a year ago around this relationship?
Hey, there's a job to be done there. Which is, I want to know what I don't know about myself.
Slack, in this case, their first release basically hit most of those. And so it was. All of a sudden, we were in the lead. All of a sudden that was threatened really fast. I love what you're doing with clarity. I just.
Metrics versus not metrics.
Yeah. So for me, what I was. When you and I were talking about last time, the thing that appealed to me when you were talking about is like, it's really like a personal performance management app. Right. I mean, I hate to say that, like, you. And that's probably terrible marketing for it, but it really is about, like, making use of, like, the things that. Like, if you write it in a journal. The thing that. The only time a journal is really useful is if you're deliberate about it. Like, you have discipline in writing in it regularly, and then your mind will clarify. And, like, you work things out. Just like when you go into therapy or something and you do it regularly. Right. Your mind tends to work those things out kind of in the background.
Because it's internal.
Yeah. As you're doing it, as your finger is. Your fingers are writing in the journal. However, like, it doesn't necessarily. Like, all the years and months of the journal entries that you put in aren't necessarily. It's just all in the history. Right. Like, it's not. It's not. It's not valuable. Yeah. Or it's like it's in. What's nice about a journal is it's a. It's a permanent history.
Yeah.
That, you know, I mean, there's no permanence in our memory. Our memories are always fleeting, especially as you get older. Right. Like, and so, like, the journal is, like, the factual history of your. What was in your mind at that time, in your experience. And so. But there's nothing. A lot of that is just like written and put away and never to be seen again.
Exactly.
And that's what, you know, when you told me about clarity, I thought, oh, wow, that is. That's brilliant. Because I was thinking of, like, we're talking about it. I was thinking of granola. And I thought, like, granola's brilliant. Like, I remember I used to use granola for all my meetings. But even, like, the, the best part of it was, like, I would use it for interviews. Yeah. I'd interview someone and I wouldn't even take notes. And we have our rubrics. Like, you know, like, here's like, you know, your rubrics that, you know, how you measure people during an interview. And after the interview, it would summarize the call. But then I could chat with it. I could say, hey, you know, I can say, hey, based on these rubrics, what'd you think of this guy? You know, and it would summarize based on that. And then I can ask him more questions and I can ask it to give me, like, exact examples. And I can look at the, you know, like, where this person said this, and I would highlight that and put that in my actual summary of how that interview went. So things like that are really cool. But it's also going back in time. Like, say I interviewed someone a year ago and I was using granola and I noticed this guy popped back up. But I don't remember that interview. But I have it. I have it because it's noted, it's in history. Right.
That was like a magical moment.
That was a magical moment. And so I imagine, what if you could do the same thing with your thoughts? Like five years ago, your journal. Yeah, yeah. Not even five years, but just like, let's say a year ago in your personal relationships, you're working something out with your partner or something, and I don't know, you just a lot of things you forget about. Or like, you know, just be able.
To get the content.
Yeah. Really cool to be able to do that. Or things like have it remind you. What if it could pull out events that happen? Yeah, you know.
Oh, I love that.
Right. Like, you pull out events that happen and then you have an integration with a calendar. And like, you can actually have those in your calendar. Right.
Like, oh, that's cool.
And I don't know, just little things and little reminders like, hey, you know, so and so's birthday's, you know, in.
Oh, like a memory February sort of thing.
Yeah. You could do so much with that.
Yeah.
Aside from the insights of whether or not you're accomplishing your goals or you're living up to your beliefs, I think those are important too. But there's so much more you can do with it.
What would you call the. In Teresa Torres language, it would be opportunity. And then in Bob Moes's language, it would be job to be done. What would that job to be done be?
Oh, God, I don't know.
Like, what is that feeling? Like, what does that solve?
I don't know. I mean, for me, it's more of a. I think the promise of AI is about truly being your assistant over your life. Right. It's just like the biology. Things fail. Our memories are going to fail, our, you know, things that we forget, things over time. We're not perfect. I mean, whereas, like, if you have some history of everything that you've done or things that you've talked about or things that at least you're sharing on paper, and if you could make use of that somehow, like a living autobiography. Yeah. It's just like, is this all preservation? Here's how I would use it. Right. Like, I would use it just like a journal. Like I would, you know, whether you.
Just want to journal.
I always want to journal. Right. Like you. Whether on. On whatever device I have, and I journal, and every once in a while it would give me some insight or it would give me. It wouldn't even. Maybe not even insight, but, like, at the end of it, maybe, you know, later, next day or whatever it says, hey, you know, based on your journal entry from last night, I found this. This event that you talked about or I found. Yeah, I found a pattern I found or something. Some sort of insight that has something to do with helping you work out or remember certain things that are important. Right. Because sometimes it's not about like. Like a therapy thing. Right. Sometimes it's just about like, oh, here's what happened this day. Like, I had this great.
About a relationship thing.
Yeah.
So let's use that as a use case and then we'll get into the interview. But finishing out this interview.
Yeah. Yeah.
So, yeah, give me a use case of, like, you know, you journal for a month and then 30 days later, it gives you something about relationship stuff. Like, what do you imagine might help you towards that?
Yeah, I mean, I don't think it should give you stuff just to give it to you. Right. Like, it should be smarter than that. It should be about, like, it's like today when you talk to ChatGPT, for example, it doesn't preemptively start up conversations saying, hey, Rich, I was thinking about this. Right. It doesn't do that. Right. It's an interaction based. It's triggered by an interaction. Right. So like if I interact with it and then I mention something like, hey, you know, I write my journal and, and I said I had a really tough day with so and so today for X, Y and Z reasons or whatever. And you know, an insight with that may be like, you know, this happened before, you know, like, you know, or maybe like if it can suss out like some pattern or something. I don't know, I don't know all that. There's probably, you know, millions of different things that it can pull out. But like, I don't know what would be interesting? I think right now for me, what would be interesting are the memory type related things helping you remember things.
Right.
That, that can apply to anyone.
I love. Like what do you think of the, you know, Apple Photos, Google Photos memories, like last year.
Yeah, yeah, yeah, yeah. I think those are great. I think they're wonderful. I think if you can marry that with journal entries, that would be great as well. Like iOS does that with their journaling app a little bit. Like they don't preemptively feed you, they give you the opportunity. Like if you took pictures that day when you write your journal, you're prompted with the ability to use that photo as your journal prompt. Right. Like if, you know, but like that it's not feeding you anything but like, I don't know. I mean, I think those memory things are cool. But more, more than anything too. It's like, I don't know, this would be interesting to see. Like what, what people, what do people write about in their journals? Yeah, right. Like a lot of times it's like therapeutic type stuff. Like so sometimes I'm like kind of.
Just venting in my journal.
Yeah. Oftentimes it is. Right. Like it's like I'm frustrated by this or my son frustrated me today because like, whatever. Right. And so, yeah, maybe there is no particular insight. Maybe it's more like granola where it's like I want to mine that data.
Yeah.
Right. And then I can chat with it and then it's got all the context about it.
Yeah.
Which would make it a little bit more simpler. Right. It's not giving you, it's not throwing a dashboard at you.
No. It's basically like kind of your digital twin that you could be like, hey, what happened a year ago around this relationship thing.
Yeah. Or tell me something I may not already know about my relationship with so and so.
Yeah. Based on everything I.
Based on everything I've told you.
Oh, I love that. Oh, so like a granola experience like that where you could talk to Clarity and it basically acts. Accesses all the contacts.
Yeah. Have you ever asked Chat GPT that?
Yeah, like, I've asked it to create a viz of, like, what do you think my life looks like based on everything I've asked you? Yeah, and it's created it, and it had, like, dogs and stuff. And I was like, not bad.
Yeah. Yeah, yeah.
It's kind of interesting.
No, it is fascinating when you use ChatGPT in a way where it's like, you know, I'm just gonna. I don't have any thresholds for what I tell you. I. You know, if you tell it a lot of things, if you ask it to tell you something about you that you may not already know, it's fascinating. It's just. It's really fascinating.
Yeah, totally. So you imagine, like, something similar. Like, there. It sounds like there's a job to be done there, which is. I want to know what I don't know about myself.
Yeah. Or your relationships or, like, how you think this through or how you, you know, I don't know. I mean. I mean, you want. You want to be careful about, like, this therapy.
You don't want it to bias you.
Yeah. And I don't want it. You don't want it to become a therapist. Right. Like, you have to be careful with that. But, like, I think insights on, like, hey, you know, this is how I perceive you. Or this is how. This is just more of, like, my perspective of, like, you know, from my angle, like, what you've told me, I'm reflecting back at you.
Like, okay, this is super valuable, man. Thank you.
That was really.
I really admire your work. So it's valuable for me to even get you to use my thing and give me feedback.
Well, I would use it more. I think that I got overwhelmed because, like, there are metrics in their snippets, which I think are useful.
Yeah.
I think if I really, like, we're really picking. Picking out different things. I get what you're trying to do. Like, I mean, like, you know, reinforce belief system. Right. That's important. I think what I'm thinking of, like, for myself, what I would want is more of a kind of a generic.
Yeah.
Like, you know, something that records my memories, my Journals, my thoughts.
What do you think of like the daily check in thing? Like do you like that like, or.
Do you want to just go to. I think prompts are important. I think prompts are good because you need some way to get people to come back and do it regularly because it is a habit that you need to form. I mean I even that like I, I'm not religious about like writing in a journal, but when I was traveling like I was, I did a solo trip to Japan February and I was journaling every day, maybe multiple times a day just because for one, like I, you know, traveling in a country where you don't know the language solo, it's kind of isolating. So like being able to write it down and, and have those kind of discussions with yourself over a journal is actually kind of nice.
Very valuable.
And it's, and you, you discover a lot about yourself.
You're connecting yourself.
Yeah, yeah. So, but yeah, I mean I think prompts are good somehow some sort of prompts. I think prompts based on AI is even greater. Like so you know, AI can ask you like, hey, how are things going with this? You know, you told me about this like 30 days ago. Yeah, yeah, you know, how are things, how are things going? Right?
Yeah, like something with your son two weeks later.
Yeah, yeah, let me check in on you. That. So I mean, I don't know, super valuable insight. Yeah. So like, you know, Clarity is a great name for the app.
Feel free to house it. Like feel free to fucking go in and like critique it because that's what I'm looking for. Yeah, I have a whole UX overhaul. Like upcoming.
Yeah.
Because I think it is too much right now. There's too much.
I think it's fine. I mean you're exploring and you're trying to figure out what sticks. Right. But it's important to explore that way. But to me, when it comes down to product, it's always about trying to remove move shit, you know, like just get rid of as much stuff as you can. To simplify that, tell me about your.
Product design philosophy because you've had a rich history of that and then we'll get to intros and stuff. But since we're on the topic of.
Yeah, I guess, you know, if I work backwards, like my most recent like so at Arcade we had a very simple product and it's deliberately simple. Like we wanted to create demos, we wanted to allow people to create demos, self serve on their own without requiring a technical person. And most of our customers are marketing people. They're not technical at all. And so we needed a way for them to be able to use our product without a lot of hand holding, no documentation, nothing. Like within five minutes they should be able to use it and get something out. And so when that defines your user, you design a product much differently. Right. Like, I mean, I've been on both sides. I've worked on enterprise products that are very complicated where like, you know. Yeah, or even before atlassian, you know, PeopleSoft, Oracle, you know, I hated those products because it's like I'm writing all the software for someone, like a small group of people within large ish companies. There's only a few people in the back office that use those products. And so there's no focus on usability, the experience. It's just a bunch of pages with form fields and really boring. It's not you have to use it, but like you don't enjoy using it. And yeah, so my history over 30 years in tech has been moving from that slowly over to products that were easier and easier. You had to be. I remember like maybe 10 years into my career I had this big desire to like work on a product that millions of people used and touched every day. And I got that opportunity a few times. First time was with Hipchat.
Yeah, tell me about that. What's Hipchat?
So Hipchat was Slack before Slack. It's how people communicated. And before Hipchat there was jabber.
Oh yeah, right. Oh, those days.
Yeah, yeah. What was it? Yeah, and there was like others. What was, what were the other ones? People are using like Google Chat or. Oh, Google Chat, Yammer or Yammer also. But. Yeah, yeah, but, but Hipchat came on the scene and it was founded by two, three guys. These guys from, they went to school together and they're kind of like serial entrepreneurs and they built another product called Hipcal. They sold that off and then they pivoted over to Hipchat, which is like almost exactly like. Well, Slack was modeled after Hipchat. Hipchat was a fast growing application, SAS product. Three people, three founders, four. Four people that were the company. Yeah, yeah, yeah. It was really cool. It was 2012. I was, I was the first Atlassian they met and we were in already talks with them to, to acquire them. Okay. And, and yeah, I remember, I think it's like my first two weeks at Atlassian. I, you know, I was told like, hey, you know, go visit them because they're like down the street from us. So I went over there, visited them, hacked on their product for a little bit. Did a little JIRA integration with them and cool guys. We eventually acquired them and Atlassian ran hipchat for a couple years. I don't know, three, four years until kind of slack ate or lunch. And there's a lot of learnings from that. But that was the first product that.
You really got into the design.
I got into design. I ended up leading the team that rewrote the web client.
Okay. Rewriting is hard. Rewriting is hard.
Yeah, yeah, yeah, yeah, yeah.
You rewrote it into something.
Yeah. Because it used to be this Adobe Air app. That was the original app it was created in. And when we, when we acquired them, a lot of the customers were asking for mobile apps and native apps. And so, you know, the team grew from that four people person team to like, you know, Atlassian just threw bodies at it. Eventually we got to like about 20 people and we had native developers pretty much, much on every platform building like basically just parody with what was there. So there was no, like for like a year, a little over a year. There was really no innovation. It was just like rewriting, a lot of rewriting. And so I was on the web client side, we were rewriting this app, which is like a, like a 20,000 line jQuery app. It was crazy.
That's crazy. Oh my gosh.
Yeah.
So what were the. So you talked about how at Arcade you had a particular ICP or Indigo customer profile and Persona and that informed the design constraints. So what are the design constraints around hip chat?
So Hipchat, I mean, the design, like.
How do you think about that with the rewrite?
Well, yeah, so it was inherently already a simple app. Right. Like it's a chat app. Right. Like you have rooms. You know, in Slack we all know them as channels. Channels, Right. But in Hipchat there are rooms. You create rooms and you can do DMs, you know, one on one chats as well. And so it was already a simple paradigm. It's a pretty well known paradigm. I don't think hipchat even knew that.
Was the first time you worked on.
Something I worked on. Yeah, it's the first time I worked on it. We were dealing with a lot of new technologies. React, we were the first users of React. Atlassian, this is 2014. 2014 was at the time, 2014. That was the first React has came out like maybe a year or six months before that. Netflix was the first big application on it aside from Instagram. And we came out. Hipchat came out like the third or fourth big app on React, it was very early.
What were the biggest learnings from like all of them?
Yeah, that's a separate podcast, honestly. But like I learned so much in the sense that you know how to not fuck up a product.
Tell me, how do you not fuck up a product?
Well, in this case, there's a lot to it. There's various. Like the perfect storm with hipchat, right there was. There's a hot competitor in the market. It was a viable market for sure. As ripe. There were no competitors. Hipchat was just growing and growing and growing. And Atlassian kind of just sat around letting the hipchat team do what it needed to do, which is build native clients. And so we didn't focus on things that our users were really asking for, aside from the native clients. And in the Slack, meanwhile had taken. So we had a public tracker that people would submit their requested features and we would rank those. I forget what the software was, but you could easily get the top 20 to 50 ideas that people wanted and that people voted for. And that was very active. And so it was a great list of requirements for anyone. Slack, in this case their first release basically hit most of those. And so it was like all of a sudden we were in the lead. All of a sudden that was threatened really fast. And the adoption curve was very. Started leveling out. Yeah, started changing. Like people who had used people who had already used hipchat. We're staying with hipchat. And it was slower for those people to move off, but the ones who are considering moving onto a collaboration platform were quick to go with Slack because they had all those features and more. And so we quickly found ourselves in catch up mode. And at last 2013, 2014 threw all its resources at it. We had a year, just a whole year where the founders said, you know what, we're going to throw everything we have to fight this. And so we grew that team of 25 people to about 200 people, like in like less than six months.
Wow.
And they.
How do you even like mobilize people to be effective in that time period? That's like.
Well, that's the thing. It's really, it's really challenging. We had never done it before. You know, Atlassian wasn't that big of a company yet then.
So wait, how far into your career are you at this point when you're faced with this threat of Slack eating all the market share? For Atlassian, where you're early there I.
Was like, midway through my career. Yeah, yeah, that's midway. So like yeah, it was 2013 around there, 2014.
Zooming out a little bit. So this is a really rich like we dove into this rabbit hole of like okay, design and how to not fuck up a product. And it seems like the learning there is that, hey, there are competitors eating our lunch money. Okay. The founders just threw a bunch of resources. But that didn't win.
Yeah, and that didn't win because execution was really challenging. We were challenged by the technology that we chose. Originally the founders chose to run hipchat. Well, Adobe AIR is on the client side but like on the back end side we were using xmpp, which is like the channel chat protocol that Google had invented is open source, is great. But like it was not great for web based chat. It was very heavy. It was made clients, it made it difficult to create clients.
That was the bottleneck.
Yeah. Yes and no. I mean we also an engineering team growing from a small engineering team to this large engineering team where he had many deploys a day, many people and like it was modern deployment. Like we were shipping directly to prod, right? We would go, we would run our tests and then after anything pass, it goes straight out. It's really hard to do that when you have millions of people accessing your app real time, chatting away, all of that.
That's hard.
And clients have to reconnect when you do that. And like you get these. We used to have these issues where like we would have a reconnection storm where like, you know, you get millions of clients that disconnect and all of a sudden they're reconnecting. They're just like slamming us and they're, you know, there's a lot of like really interesting engineering problems that are easily solved.
Now were you in the cloud?
Yeah, we were in aws. Yeah, yeah, yeah, we were in AWS then, you know. But yeah, we just like a lot of things like our clients didn't all work the same way. Some clients worked a little bit better than the others. There was no unified code. We would have. We were just shooting ourselves the foot because we were just like in this catch up mode and it was like the stress level was really high. Meanwhile, everyone's new on the team. Engineering management was really new and it was a flat organization. So everyone was like encouraged to go for it. Yeah, to commit and push out as soon as they can. Even like the first day engineers, there's always this like thing on your first day. You should try and commit to production on your first day. That's a Cool culture. It is. I mean, I think Atlassian had always had culture, culture like that on most of its product teams. And you know, we were very much experimental on a lot of things and you can get away with it with a lot of products. Hip Chat's one of those products you don't want to screw with too much because it was very brittle at the time. You could, you know, if you had architected it in a way that was scalable and better. Yeah, you'd have a lot of safety built into it. We didn't have a lot of safety built into it.
Okay. So it was catch up and you were dealing with basically product tech debt from this.
A lot of tech debt. Brittleness.
That's interesting. And I want to dig into that more at some point, which is design at the intersection of architecture and planning, which like if you don't do the architecture well and the learnings from your customer discovery and experiments don't make it to that level of technical planning. It's kind of like remodeling a house.
Right.
Like whoever architected the thing and then if you're remodeling a house, it's generally always 3 to 5x to class in time. But then if the architect did a good job and they had great requirements and they understood kind of like the vision of like how this household or this customer base might grow or the product might grow, then you might make better decisions. That is hard though. That's really hard because like, you know, you're also trying to get a product aftermarket. There's trade offs with speed versus clean architecture. So. But let's put a pin in that because I actually want to go back to like what makes you who you are.
Yeah.
And you've shared with me your kind of come up through Oracle to this crazy story that we gotta get into, which is how you got to Atlassian. I want to dive into that. And then what brought you fast forward. You were at Launchdarkly and then Arcade and then you've had many life experiences. And you're also. You do a lot. You mountain bike, you do photography and you're very excellent with photography and videography, which is also. This setup is due to Rich. Shout out Rich.
Thank you.
If anybody needs help with photography and videography, hit up Rich. Like if you like this, this is all hit me up. And future pod guests like you could think Rich, but you have a very strong creative drive. You're a builder at heart and you also have an eye for design and you have a lot of Creativity that I see that comes out in the products you build and the products like you ship in terms of photography and cinema. So where did that all start? Like, what makes you who you are?
I don't know. I mean, I've always enjoyed art and design from an early age. I wanted to be an architect, you know, when I was in high school. I grew up in Southern Cal. Yeah, yeah, yeah, Louisiana area. And then I, I went to Cal Poly San Luis Obispo and I, I studied math. I applied as a math major because I, I didn't go to a great high school. And I was like hedging my bets because like, I didn't think I would get in as an architecture major. As architecture at Cal Poly is very competitive. It's pretty well known back, even back back then. And so I decided, you know what, I'm not going to take the chance. I will apply as a math major. I really love math and that's, that's a versatile major. And then my, my plan was to change majors.
Okay.
And after my second year, that, that was kind of thwarted because like, it's so difficult to change majors at Cal Poly. You'd have to. Plus the fact that like most architecture majors, it's a five year plan. For most people it's not a four. It's like by default, it's a committing.
To another five years.
Yeah, it's like by default, it's a five year plan. And I would add it would be a six year plan if I change majors. And so I decided, you know what, Screw it, I'm going to stick with math. A lot of computer science courses is part of my curriculum. I had been playing with computers since probably when I was 12 years old.
What'd that look like?
Oh, God. My brother had a Timex Sinclair 1000. It's like a little tiny computer you hook up to your tv. It's black and white. You have to have the game controller in the back and put it on channel three. And there's no, you got to turn the volume all the way down and it launches with basic and you type in your program. I had a book with all the bunch of games and you just have to type them in. And at one point we got a cassette recorder. You can hook into it and you can record, you can record your, your program onto a cassette tape. Oh, and so what that would be, a cassette tape would act as your hard drive. And then whenever you, you know, you come back to it later, you would have to, you turn the machine back on and Then you turn the cassette tape on and you play the cassette tape to the input to the computer and it read your program. Sometimes it works, sometimes it failed.
Cassette tape programming.
Yeah, yeah, yeah. So that was in the keyboard on this thing.
It's like, easy nowadays.
Yeah, the keyboard was like this big. It was like 6 to 9 inches. And it's a puffy pad. It doesn't have, like actual keys. It's like the puffy pad thing. And so that was my first computer interaction. And I think it's like most of my friends had like Commodore 64s or Atari 800s. Yeah. So got to play around with computers pretty early on. It wasn't like, you know, getting into high school. It wasn't like something like there's. I had friends who were like, really into it. Like. Yeah, they probably became computer science people. And I was into it, but I was. I liked it. I loved the challenge. I loved the logic, the math part. But I was. I don't know, I was into art and design and so. But when I was a math major, I took a lot of computer classes. Programming. I almost got a movie. I should have gotten a minor in it, but I didn't want to.
Turns out you don't need it.
Yeah, exactly.
Wait, so what happened after. So you were interested in computers early, you had a creative mind, you were interested in architecture, but you went in for math. And then.
Yeah, and then my last year and senior year. I mean, it was kind of like the start of the gold rush, the tech boom. Yeah. And let's see. Jobs were plenty. Like, we. There were a lot of, like, people recruiting on campus, but they were like. They weren't like big tech companies. They're like, you know, management consulting firms looking for tech people. I happened to get into one of those. I worked for a company called Hewitt Associates. And it was like insurance and benefits and actuary. So it's like a mix of math and computer science. I hated it for a year and a half. I mean, I was like their. So I tend to, like, my personality is. I tend to. When I get into something, I tend to like, really rabbit hole into something.
Obsessed.
Yeah. And so back then when I was working, you know, and a whole bunch of us fresh college grads started working at this place. So it was great. It was like. It was like college all over again.
Right. You had people at your point in your journey.
We were working like crazy. And it was one of those places where they fed you morning, day and night. Right. He had a kitchen, is always stocked and it was great. It was, you know, the start of, like, that whole, like, you know, the whole era. And so, yeah, we're always at work, and I just found these little problems. Like, there's a problem with, like, defined benefits, 401k, defined benefits, retirement plans, and, like, modeling these things. And, like, I had a friend in another department who wanted some help modeling this stuff out in a spreadsheet. And back then, Excel wasn't even a thing. We use OS2 as our operating system at work. And it was the whole Lotus suite. We used the Lotus one two, three. So I learned Lotus one two, three built a bunch of programs on Lotus one two, three, Help people model out different things. That was, like, start of, like, a little bit of programming. And then, I don't know, like a year and a half in a whole bunch of people started migrating over to a lot. A bunch of my coworkers started migrating over to PeopleSoft.
Okay, so you liked the, like, people you were working with because it was like college again.
It was. Yeah.
Hated the actual.
I didn't. I wouldn't say hate's a strong word, but, like, I knew that that wasn't.
This is not my forever.
Yeah. The other part was like, this is weird. Like, have to wear a suit every day.
Like, you wear a suit every day.
Yeah, we have to wear. This isn't tech. I mean, this is like. Like management consulting. I have to wear a tie every day. And it's like, just like my first job, I had my. My own office, a window office. Wow. Like, everyone did, which is weird at this company, but I said it was weird. We all had her. We had to set. We shared the secretary. It was weird. It was really interesting. Really weird.
Management consultancy.
Hiram Member. I remember there was. The CTO of that company had sent out a memo. And back then, the memos were paper. You actually literally have an inbox, a physical inbox where this paper would get dropped into. And I remember it was about the Internet because browsers were becoming a thing. Netscape was something that people are starting to install in their computers.
And what year was this?
This was 1995. 96.
Got it.
Got it. Yeah. And then, so this memo was interesting, and it was like. I don't know, it makes me always wonder, like, I wonder what the CTO ended up doing because he. He sent this memo out saying basically that the Internet was a fad. Just ignore it. Interesting. Yeah, interesting.
Look at that in retrospect.
Yeah, exactly.
What a horrible take.
Yeah, exactly.
Retrospect.
Yeah. Yeah, it's like saying AI is a fad.
Such a fad.
Yeah, it's going away. Yeah, exactly.
Okay.
Yeah. Anyway, so. Yeah, PeopleSoft. So I went to PeopleSoft. PeopleSoft. I was a consultant. Oh, I was. What's that?
Implementing the product.
Yeah, implementing the product. So I was part of what was called Professionals, the professional services group. And I got a cool job. The Thursday before I was supposed to start, I started on a Monday when I got, you know, after I got hired, my manager called me Thursday before and she said, hey, Rich, we've got an opportunity in Melbourne, Australia for six months. Yeah, are you interested? And I had to think about it because at the time I was thinking about it, it's like I don't even have my passport because I hadn't traveled out of the country, you know, and so. And I was like. And I was, I was telling her this and. And I said I had all these, like, little concerns, you know, trying to stop me from doing it. Yeah. But she was like, no worries, we'll get, we'll get a passport out to you. Like, we'll fast track that.
Yeah.
So that was Thursday afternoon.
Thursday afternoon. And you were going to start Monday.
Yeah.
Three days later.
Yeah, yeah. In Australia. So passport got fast tracked. On Friday, I had it in my hands. By Saturday, I was on a plane. On Sunday. What? I was at work.
Life changed immediately.
Yeah. I was at work on Monday.
What?
Yeah.
Wow.
It was wild. That's wild. And it was like, how'd that first day go? It was amazing. It was great. And it was wild. It was really wild. I worked for the Department of Education for Victoria in Melbourne and I was writing COBOL code for their payroll product. Payroll? Yeah. Basically I was basically. Because PeopleSoft at the time was not an international product, so whenever we needed to support new GEOs, they would send a whole bunch of consultants and basically implement those rules into the product. So that was part of what I was doing is I was implementing all the payroll rules, benefits rules for Australia. Yeah. That were region specific and on top of that, government specific, because this was for the Department of Education. So. Yeah. But that was a great time. I mean, six months as an expat with a bunch of Americans. That's so cool, dude. That was like. Honestly, I think that was probably like the highlight of my career in terms of like the soft parts of the career, the fun parts. Every weekend we were traveling all over Australia, just seeing different parts of Australia every weekend. Like the group. Oh, God. All. I mean, all of it there. The whole, like every weekend that those six months I felt like. Or every few weekends we would travel, we would go diving, we would go, you know, like it was a bunch of. Yeah, we were all from America, we were all expats and there are a few from like six Singapore and a few other places. But like, yeah, we had a Asia PAC consulting kind of off site. And you know, I'll tell you, back then in the late 90s, this is when like budgets were going crazy. Like everyone just. There was just so much money flowing. So the guy who's running this part of the business said, hey, we're gonna, we're gonna do an off site. It's a three day work off site. Everyone planned on being there. So we flew out to Brisbane and then we hopped on a boat and this boat, like everyone had little cabins, like a small little cruise ship for like 20 people. And that boat was headed towards the Whitsundays. The Whitsundays is this really beautiful, like Hawaii, like a nice version of Hawaii in Australia. And we had a whole weekend, the Whitsundays, we ran two x Americas cup boats and we did it. We had a regatta on the, you know, another day. And like it was just like this, like all expenses paid. And we had like a 20 minute meeting on a beach. That way they can call it a company thing. Yeah, yeah. So that was like the first. And that was like, you know, my early 20s. This is the first time I've ever. Yeah, exactly. I was like, oh, shit. I mean, what comes after like with like a lot of the tech companies later?
This is like foreshadowing.
Yeah, foreshadowing, all that. Yeah. So I spent many years at PeopleSoft doing. This is.
So you were two years out of college, started at PeopleSoft, moved to Australia and then how many years?
Six. I was in Australia for six months.
Yeah, and then you spent. Okay, six months.
And then how long at PeopleSoft and then. Yeah, so PeopleSoft, Oracle throughout the combined thing from 97 to 2011. So 14 years all in total. And in hindsight, I think, yeah, that's like way too long. Right. I could have done a lot more with my life career that I definitely, I knew now. In hindsight now I should have gone the entrepreneur route. I could have started companies back then. But yeah, Fast forward from PeopleSoft on for that, like.
So why did you stay? Why were you staying?
So I stuck around like in 2005, so PeopleSoft had undergone this like hostile takeover from Oracle. Right. 2004 or 5. It finally got resolved in 2005. I believe 2006, we'd lost a lot of people from PeopleSoft. And then it was just, everyone was just questioning whether or not they're gonna stay or they're gonna leave. I stayed specifically because I just had a family. So like I had twins. My twins were born. Yeah, my twins were born. Yeah. Married? Single. Single income, family. And so you're about 32. And I'm pretty risk averse. Right. Like I'm not the risky guy. And. Yeah. And I just, I was in my. Yeah. 30, 32. And so I stuck around, but I had this very different attitude about work at that point because I was on that edge. Was like, you know, I'm close to leaving, but I'm not ready to leave. I'm not ready to throw it away. Right. And I was a little afraid of what's on the other side. Yeah. So. And there, I think there are a few of us. And that's where I met Paul. I met Jake.
Jake Carmoto.
Yeah, yeah. And, yeah. And Anthony. I don't know if you knew Anthony. Yeah. But we started the Apps lab and that was like purely.
So it's just like an R and D lab.
Yeah, yeah, yeah. So Paul Pedrazzi I'd worked with, he was a product manager at PeopleSoft. He was working on this product called the Enterprise Portal, which I had spent a lot of time on building. I wasn't an engineer on that team, but I was like an outside engineer. This was like my story of my early career. I was never really part of an engineering team. I was like user that was like very technical and also coded. Right. And so I would oftentimes like use the product like crazy, like the best. I'd be like the best user, the super power user. And I would tell them what's wrong with it. I would patch things up, I would help fix. And I did that for a number of years. Paul was one of the product managers on that team and he and I got to know each other really well. And this is the time around 37 signals, Jason Fried and DHH was like, they created Basecamp and all that. And they were very prolific about their methodology for building a company and building product. Back in that day, this 20 2005, 2006 or something. Yeah. So we had just left and the teams that we were on were kind of like in limbo and Paul and I had spent a lot of time, I think this is like there are all kinds of really interesting new products that are coming on board and they're like one or two people Companies. A lot of it was in the productivity side. Productivity apps were a big thing, and they're really fascinating. Of course, 37 signal stuff was the big thing back then. I think part of it. The product was fine. It was a cool product at the time, but I think the two founders were really what made that company. Yeah. And they were very prolific about just everything. They'd written a book on how to.
Run a company, by the way. No bullshit.
Oh, yeah. So, yeah. I think that whole period after PeopleSoft was acquired by Oracle, I had this different mentality. You know, when you.
Good work.
Yeah. With work, it's like, you know, I had this. I don't know what it was. It's like some people check out, like, you know, and they're like, demotivated.
Yeah.
Or they can, you know, they'll go out and look for the next thing. I was. It's quite the opposite. It was like. I knew that, like, having the job at Oracle, like, you know, the. The pay was good, everything was good. It's like. And I'd been there for a long time. Like, the seniority was good, but also I realized it's a whole new kind of world. The company's changing. There are a lot of people like me who are kind of demotivated, and I turned that around. A few of us turned that around. I mean, like Paul Pedrazzi and Jake and I. And Jake was on the Oracle side. He wasn't at PeopleSoft. But same thing. We're like, you know what? There's all this stuff going on the Internet. This is like, you know, Web 2.0, like, the bubble blown or was about to blow. But, like, there's all this stuff that was going on. A lot of really cool companies. I saw the effects of one of these companies when I was at PeopleSoft. LinkedIn.
Okay.
I swear, like, I. We probably put LinkedIn on the map, honestly, that year or six months before, before the acquisition happened, before the hostile takeover happened, because all of a sudden, everyone was like, connecting on LinkedIn. And that was such a foreign thing because there was no social network. Like Facebook, Twitter weren't even available. Right. They weren't out. So the first social network that a lot of us had ever touched was LinkedIn. And it was professional. Right. Like, people were leaving their jobs, but they wanted to stay connected.
Yes.
And so it was fascinating to me how fast that grew. So that was always in the back of my mind. It's like, wow, that was really cool.
How fast did it grow?
It was growing fast. I mean, I don't know, I don't know what the numbers were, numbers.
But like just timing wise, like some events. I know you kind of told me this story before about how I even started like Jake doing some market stuff and then that some of this eventually led to you meeting Atlassian founders, right?
Yeah, yeah, yeah, yeah. So fast forward to that. So LinkedIn was kind of like the motivation for exploring social more. Because the interesting part about social was the adoption curve that we hadn't seen. And for me, for someone who has always been like, I want to work on a product that a lot of people touch, a lot of people use. And so that was a perfect opportunity for that. So when Paul, Jake and I, we're talking about this and we're thinking, you know what, what if we could convince some higher ups to let us start up a lab, let us work on some skunk works projects.
Yeah.
So Paul, Paul's really well connected. He's great at working the executives. And so we got executive buy in. We had a senior VP sponsor us and we started coding, we started building this thing and we thought, okay, let's just explore what we can do. It was three of us at the beginning. And then we got Anthony, he was the fourth, he was an engineer. And by the time, by the way around this time, there's no cloud. Like at least we didn't have access to one. Amazon wasn't starting, but it wasn't all self hosted. We didn't have access. We were our own little tiny department department. We didn't have space in the data center, we didn't have anything. We were running these things on our machines. And then we got to a point where, and then this is where Jake really comes in. Jake's really great at, he knew a lot of people at Oracle and had connected with a bunch of people. Eventually we found someone in the data center who was giving away or not giving away, but they're decommissioning machines because after three years that was like the normal process. They decommissioned these machines and so before they retired then they would just sit there and so they let us use them. Cool. So like, okay, we're going to run all our products on there. Yeah, yeah. So, yeah. So we started working on servers. We had server, yeah. And the first thing we wanted to work on was we knew that the people component was important. And at the time Oracle, Oracle had. Of course, Oracle's a database company, right. So everything that they had at the time were just like database focus. Like meaning that there's no focus On UI or usability. Like they had their company directory was literally probably a table or two inside Oracle database and they put a really, really crappy HTML basic HTML UI to it with like a bunch of search forms. It was like, literally if you wanted to look for someone, you have to type in, you know, this form, this big form.
Definitely not elegant design.
No, no. And then eventually you get a table or just a list of people's names. You have no idea where they worked, what they did. You might get their phone number because back then we still had phones in the office. So we thought, oh, that's an opportunity. Can we get that data somewhere? Can we scrape it off of the system or, or like, could we, like. So we eventually ended up getting a dump from hr. So the HR again, Jake, Jake with the connections, he talked to someone and somehow we were getting nightly dumps. We were getting employee data. Nightly dumps. Nightly dumps of employee data. It would just show up. Yeah, and so we used that, we built our first directory and we enriched that. Yeah, so we enriched that. It was, it started off as just a directory. Like now it's like a beautiful directory with faces, all the relevant information. And then the big thing was like the hierarchy, right. Like who report? Because I mean, with an 80,000 employee company at the time when we joined, 80,000 people, that's a lot of people. And so you needed to see like who, what department, like who do they report up to, how far are they from Larry, that sort of stuff. So that was the big first like UI UX thing that I was pretty proud of is like how you traverse, like. So we invented this, this kind of like drop down way. I mean, it's not how you thought.
About that because we were speaking about design and I love picking your brain on design.
Yeah.
How do you think about solving that problem? Because that, you know, like you didn't see anything like that before, right?
Yeah, but a lot of times I think you, you know, when you use something enough, you use other products, products enough, you start to make connections. And I think honestly a lot of the craft is about spending a lot of time, you know, and yeah, you could tell how it's how. I mean, experience does matter. I think in this particular case, for that particular problem, you use the product enough and you start to see patterns like, oh, I could do this better. Right. What if we did this right? Like, and so you start to form that and it turns out what you end up with is actually better than what was there before. So it's a lot of iteration. I can't say we come up with it right away. And it's the first time. It's perfect. It takes a long time. We built this directory to start and then we started adding because we have the users, that's the center pointer, the users that the users or the employees. And we started adding social elements to it. The first social element we added to it was Kudos. We wanted, you know, there was this common thing where people like we were seeing it within our department where like people will help us, like with compute. Right. Like someone in the data center donated some decommissioned machines to our project. People in HR started giving us. We wanted to thank them. And so we created this like, kudo system. And back back then for likes. Well, back back then you had in LinkedIn the big thing where was it testimonials or something like that where, like people can add comments. And that was big. That was huge. Like, if you look at my LinkedIn profile, you'll see like a bunch of like, I think they're testimonials about you.
Yes.
And like they're like kudos, basically. Like, you know, Rich is awesome. He did this or whatever, right? Yeah, yeah. If you look at all those, all the testimonies I have are all from like PeopleSoft, my time at PeopleSoft. Because that's when it was used, that's when it was released. And so, yeah, so we modeled Kudos after that and we added the social element we added to it was that it would email people. Right. And within the first three weeks of having turning that on, we had like a third of Oracle using our product.
Connect just a few weeks, and then a third of Oracle. So that's thousands of people.
Yeah.
And also just to contextualize for anybody that doesn't understand getting anybody to adopt anything internally at a big tech company. Fucking hard.
Yeah.
Change management, hell of a thing. Culture change, hell of a thing. And so like going viral within a company.
Well, but that's also the golden period of social. This was before Facebook and Twitter. Actually Facebook and Twitter were just around that time getting released out to the public. Right. Facebook had been around for a while in the colleges, but like it wasn't public. And so there was an itch. There was an itch. Yeah. So a lot of those tactics of like emailing and viral sports spread. Yeah. Today they wouldn't be as successful because people are trained not to just ignore that. Right. But like back then, it's like someone got an email saying, oh, so and so wrote a. Gave you a kudos yeah. You know, and then you can click on a link and it would take you to. Yeah, to our app, it was called Connect. And they would go in there, you're immediately in there because we had single sign on. And they can go in there and they can see. Oh, it's like, like, oh, that's cool. And they, they, they could compare that. What is this? This looks like a directory compared to their crappy like form based database field list. Right. And they're like, wow, who did this? What is this? So like we got people using that and then we kept on adding features to it. We're just experimenting, adding more and more features to it. We added a forum like, like a community asset. Yeah. Where people can go in, add content. Right. Like blog, they can blog. These blogs are big back then so we thought people could blog within their departments and we would, we created an activity feed. So like that was the first, first time we'd had to deal with like you know, fanning out, you know, architecture design so that you don't like get everyone clobbering the database.
Yeah.
So a lot of really cool things happened then. A lot of really cool technology type things. Design stuff. There's a lot of stuff. Stuff we got noticed we were doing. Part of the reason why I got noticed is because again Jake, Jake was amazing. He was really good with the connections. But aside from that, he was a really good blogger. Like he would write about everything we did. He was always writing content. Like he was, he's the equivalent of like the best content producers these days. Right. Like he was like always blogging and always out there trying to get our knees out. And we got noticed, we had several books written. Like we were in chapters of these books about like the whole enterprise social thing. We got invited by Google to speak on a panel and that's actually, that's where I met Mike Cannon Brooks. He's, he was one of the founders.
Of Tell Me this Story. This is a cool story. And then for the audience we'll, we'll link some of the books in the show notes.
Yeah. And so, yeah, so we did all like, you know, we were in this enterprise social media space for a while at Oracle and we got invited to a few things and then there were a lot of movement at this point. Facebook has been out. Google was kind of panicking about what they were going to do when it came to social. Google's always at the end, tail end of things. So they're always catching up. They decided this is open, open, open source is huge. Back then, like, and so they want to build out in the public. And so they created this project called OpenSocial, which was like their answer to Facebook. Like, they wanted to create this, like, set of technologies and specifications that would allow any company to create a social network. And so you got all kinds of crappy social networks out there, or cut high five. There's a dozen of these and every country had one. Right. But opensocial was a thing and we at the time were looking at like, maybe we should use this, maybe we should use this to create our product. By the time, at this point, we were still trying to sell our product internally to Larry to basically like, hey, we want to.
Oh, yeah. Even though it got virality in.
Yeah, he didn't care about that. I think he cares about is whether competitors are doing it. And so he didn't actually treat it seriously until like years later towards. When we were on our way out. Basically. Yeah, Salesforce got into it. Salesforce created a product called Chatter and then Microsoft bought Yammer. All the big guys are starting to get into that space. And so Larry decided, you know what? We're going to build this. All the stuff that we had written just kind of like. Yeah, it wasn't even. They used the name, but they like recreated the product from scratch. So like, okay, whatever. And they package it up as part of their CRM suite, which is really weird. Anyway, so I don't think that product ever survived. But yeah, so we were kind of on our way out. But at this point point we had.
But you got noticed and you met the Atlassian founders at this panel. Tell me more about that.
Yeah, so actually, actually what happened was.
This ties into later how you even got to Atlassian early.
Right? Yeah, so I, I don't want to hear that story. No, we. So we're participating in OpenSocial. You know, we get invited to these meetings because we were Oracle. Yeah, we represented Oracle, you know, Google folk. Our friends at Google would. Would invite us to these meetings and stuff. And we went to an event at. Oh, God, what was the early social network space? What is it called? Oh, man, I forget. A lot of bands would post on there. It was MySpace. MySpace? Oh, yeah, MySpace. I had MySpace. So MySpace had a open social meetup and I went and one of our friends from Google invited us and I don't know, I was just sitting down next to Mike Cannon Brooks. I didn't know who he was. He was one of the founders, Atlassian. And later our friend from Google kind of introduced us and like, oh, that's cool. I didn't even really know Atlassian. I've heard of the name. I'd heard of Jira and Confluence, because we use Confluence in Oracle, but they're maybe less than 10 years old at that time. And I think they were successful at the time already, but not anything huge. So I met Mike, and that was my first meeting with Mike, and then we got invited to participate in the panel at Google, I o. I think that same year. So I met Mike, I met Jay, and Jay was eventually president Atlassian, but I knew him a little bit through a company called Plumtree, which PeopleSoft was almost bought, like, a while ago. But anyway, he was there in the Enterprise Portal space. So I. Yeah, so I connected with these people and it was really cool. And then that was like 2008, 2009 maybe. And then eventually I was like, by 2010, 2011, I was just like, I'm tired of being at Oracle. I need something new. Yeah. I mean, that's like 14 years of a career combined. Right. That's a long time. And so I was kind of checked out.
Kids at this time. You had two kids, you had twins.
They were five, six, maybe.
Okay.
Yeah, around there. Yeah. Wait, is that right? Yeah, yeah. So, yeah, I was just checked out.
You were going through a lot, too, at the time?
I was going through a lot. My wife was diagnosed with breast cancer, metastatic breast cancer, in. Yeah, 2008. She lived with it for seven and a half, almost eight years. So, yeah, it was. That was. That whole period was really challenging, I think. I mean, honestly, the one thing that really helped was having a job and the job, honestly, as you know, I mean, it sounds like it was a tough time, but there was a lot going on with the job that it kind of took my mind off of. A lot of it.
Yeah.
So it's. You know, people react in different ways to adversity. And for me, it wasn't that I was ignoring it. It was more like. I don't know, it was a way to cope. And also, I had this kind of extreme focus on a lot of these things and a lot of these projects. When I was making my choice to leave Oracle, that was really tough because, one, I didn't want to be there anymore. I mean, I'd spent this career just kind of languishing in this company when in the back of my mind, like, after everything that we'd done at Oracle, realized that if I had spent that time elsewhere trying or trying to start my own company, it would have been really easy to start. We had all the ideas, we had all the makings of a great thing. Yeah. It was like, it was a little bittersweet because it was like, yeah, we did all this great stuff and we were able to accomplish all these things and we got recognized for it, but it didn't really amount to anything in terms like, you know, like financially or anything like, you know. No, no. Yeah. And like, I mean, as I've told you, that was never really in my budget bucket list. I've never. I have never ever really first found.
Her story in a sec. But yeah.
Yeah, yeah. So with Cindy getting sick, it was really tough. And the kids were really young. Yeah. And it was a lot of single income house. Yeah, single income house. And you know, and the kids were, you know, it was a challenge. Challenging ages, you know, and. And schools and like living in Oakland and like, just like all of it. Right. And it was tough. And so when I. When I finally had decided, I. I did a lot of like between 2008 to like 2000 up to 2011, I did a lot of what I call window shopping where I would like, literally, like go search, looking for jobs, interviewing, and then for some reason or another, talk myself out of it.
Right.
I get a job or an offer, and like, not really. And in 2011, I was just like, so fed up. I was like talking to a bunch of different companies. And then for some reason I never. I knew, like, you know, my connections, Mike and Jay, I could have easily reached out to them, but I didn't know what was going through my mind. I must have been really messed up because, like, I just cold called Outlasting. I went on their website and I applied for a job.
You didn't even think to call the people you knew?
No. Well, the other thing. The other thing was, like, it wasn't even top of mind because, like, at the time, most of the interesting jobs, like all the engineering jobs or product jobs were in. Were in Australia. I'm not going to move. That's like, we can't move. Right. Like, and. And they had an office here in San Francisco, but it was mainly support. They had just acquired BitBucket. So that was an engineering team that was out here. But I just like decided, you know, I'm just gonna apply. No job. I'm just gonna send an email cold on their website. Within like a half an hour, I get a call from Jay.
Wow.
Yeah. He was obviously monitoring that email.
Half an hour?
Yeah. Like within. Yeah, within an hour of submitting, it says, hey, Rich, got your submission. What's going on? Yeah, let's send talk. I think that same night he had organized a meeting, an interview with me and Mike. And so Mike and I hopped on Skype pre zoom, right? So we were on Skype and we chatted for like an hour. And it was weird because like I didn't even, it didn't even dawn on me to contact those guys directly. I don't know why. But luckily it worked out right. Like I. Within like less than 24 hours. I talked to Jay, who was at the time, I think he was VP of marketing. He ended up becoming president of the company. And then Mike, you know, at the time, the CEO and co founder and worked out great. And you know, the next day I talked with Daniel Freeman. He was running product marketing at the time and they needed. And I was telling him it's like, I don't know what I want. I mean I'm a technical person, I like to build stuff. But I also used to be a sales engineer and like I could, I could do a lot of things and like I can't move to Australia. But like, you know, and they thought about it. This is, you know, I was talking to Mike and I was telling him this and they thought about it overnight and they said, you know, we're going to craft a little position for you and make you our first developer advocate.
Wow.
So I had, so I worked under marketing. I was a developer, the first developer advocate. But I reported up to marketing, which is a little weird. But that was cool. I worked.
So like you, you had your family situation. How did that, like, because that's like a whole decision.
Yeah, that was a huge decision. Like it was a huge decision.
And then you had a whole bunch of other window shopping moments when that didn't convert. Like, why this? And then how did they make it happen?
Well, it came to a lot of things because I mean with the other jobs I just kind of talk myself out of it. Like I don't want it. Like I don't know something either. One of the interviews just didn't go well or like it did go well. It made me an offer, but I just didn't like the people or whatever. Well, after talking to the three, Mike, Jay and Daniel, a week later, I actually talked to Jay. I emailed Jay, I said, hey dude, this sounds great and all, but like I'm really concerned about insurance. I'm really, you know, I mean pre existing conditions weren't covered back then. Like this is before Obamacare. And like there was A thing where, like, insurance companies can deny you coverage if you have a preexisting condition. And so, like, if that's the case, then I'm, like, stuck. Right. I can't move, I can't do anything. And Oracle had really great insurance. And so. But Jay did the legwork. He, like, researched it all for me and made sure, ensured that I had, that everything was going to be fine. And it worked out and I ended up accepting it, and it was great. It was probably the best career decision of my life.
So you called. Just to summarize what I hear, you had this very difficult family situation. You were window shopping for a while, you were languishing at Oracle, and in reflection, you were like, I should have just went and done entrepreneurship. We'll get to that in a sec. And then you cold apply death lasso. You didn't see anything in the area within half an hour. An hour, Jay hits you up that connection.
Yep.
And then move mountains to make sure the health stuff was good for your family.
Yeah.
And then you made this best career decision of your life.
Yeah, it was great. It was great.
What did that teach you?
Like, what it taught me was like, you know, as a. It taught me that if you treat people well, like, if you're the hiring manager or you're the person in charge and you treat people that way, you're going to get kind of outsized returns. Because the next few years were probably the most productive years of my career.
Wow.
Yeah. I mean, it was crazy what I was doing at Atlassian.
Well, it's also interesting to me that, like, Jay saw your name hit you up and then move mountains for you based on the previous connection you had in your work history.
Yeah.
That's so interesting.
Yeah, right? Yeah.
Like, that your reputation proceeded clearly.
Yeah, I didn't know that. I don't know why, honestly, because it's not like, you know, I. I don't know. I don't know what impression I made to someone. Yeah, that's always been. Always kind of surprised me sometimes, like, people, like, say something about you and they'll remember something, and I was surprised by that. I only had a few interactions with Mike and Jay. Meanwhile, I did know he did mention, like. Yeah, he read our blog. That wasn't my blog. It was Jake's. Jake wrote that, but he wrote about us. He wrote about what we did and how we were pushing things at Oracle, how we were trying to steer that ship, even just one degree over, you know, and I guess that was pretty admirable from Mike's perspective. So.
Yeah.
Yeah. So I mean, I think I learned a lot. I think, you know. Yeah. My first. Most of my career at Atlassian was very productive. Yeah.
Tell me about you said it was like the most productive three years.
I would even say like the first, the first few months. Honestly, like first three months was mind blowing to me. It was the first time I'd ever coming from Oracle, which is very closed wall. Larry's pretty well known for having multiple. Lots of silos, but having multiple silos departments building essentially the same product, having them compete against each other and it was just like crazy. Whereas at Atlassian, everything was out in the open. One of the values are open company. No bullshit. And what that meant was like, literally like everything's out in the open. You know, having we. That company ran off of Confluence. Everything was in this open wiki. You could find out who you sold the product to and like you can see the sales calls, you could. All of it, all the history of everything was there, which I thought was fascinating for someone coming in new. It was treasure trove of like information.
Yeah.
To like mine for like just stuff like decisions on product or like if I needed to find why they built it this way, I could do that. Right. Like, it was, it was way different. It was way different. Yeah. And I'd never experienced that before and it was, it was mind blowing. But not only that, there's like so many other values of the company that were just like spot on. Like, you know, like being the change you seek. Where it's like at PeopleSoft, I'd always heard that as like, apologize later, do it anyway sort of thing. And at Atlassian, it's like being the change you seek, it's like basically like just do it, like do it yourself. Don't ask for permission. Right. Yeah. And there are just values like that that were just amazing. And what I learned I took away from my time there was really just like. I just really wanted to recreate that somewhere else. Right. I think if you ask any Atlassian that spent any time during those early years there, that's probably what they'll say. And a lot of them have gone on to create their own companies to try and do the same thing, you know, and build that same culture. To me, the products were cool, the products were fine, they're great. But my time at Atlassian was really about like the culture, how it felt to work there. And I always wanted to recreate that. And so like when I was at Arcade, you know, when I ended up co Founding my own company, that was like the big thing for me. It's like I wanted to build the company, not just the product. So.
Yeah. So, yeah. What did that look like? Creating company, not just a product. And then also like, what made you then go to be like, yeah, I want to start a company versus before. You never even had that.
Yeah, I was an accidental.
Also, if you could share, if you don't mind, you mentioned Cindy was battling breast cancer. And so somewhere along the way, you're just single dad mode, right?
Yeah. Yeah.
How do you like, honestly, it's like the level of resilience and ability to make progress and the self determination. Like, I admire that. And so I'm curious for others, like, what carried you?
Yeah. So she passed away in December of 2013. You know, she had been fighting cancer for seven and a half years, almost eight years. I don't know. I mean, honestly, if I think when I thought about this a lot, the hardest part was really the first few years after diagnosis because you don't know when, you don't know how. Most of the time the treatment was what was making her sick. And you just. I didn't know, like, you know, within two, like every year, it's like a yo yo effect where like she'd lose her hair and then grow back and lose her hair. And then not only that, like, she would be like weak beyond belief and like, you don't know how. How long she had. Right. She was strong, she lasted. She lived like almost eight years. And so I'll say, like, literally in that situation, the hardest part were those first few years. So like 28,008 to 2010. Yes. There, you know, after a while it starts to feel like a chronic disease. Like she was. She's doing all right sometimes, and then all of a sudden something happens, but then she'll bounce back. And so, like, it felt like very much like, oh, it's kind of a chronic disease at this point. And I think a lot of people who have metastatic breast cancer at the time, there are a lot of new therapies that were experimental and, you know, and it worked a lot. A lot of it was working. And I think people are living longer and longer lives with it. So it was easy to treat it as a chronic disease and not be as like, you know, you know, when she did pass away, the kids and I joined a grief group and we were amongst like, others who had kind of similar story where like, you know, a family with kids lose a spouse and mother or father, and some of them Were sudden loss. Some of them were like, you know me. Some of them were like, had like a year amongst that group of people. Honestly, in many ways, I feel like I was the luckiest because I can't. I can't. It's so much harder, I think, to experience sudden loss than to experience, you know, kind of like this prolonged battle kind of.
I suppose.
I don't know. For me, I was able to deal with it much more. I remember the point when I realized, like, I mean, all of our time, we all have expiration dates. Right. And that I never really thought about it before then that much. You know, it's like. It's like this fuzzy thing. You know, people, you just expect that, you know, we're going to grow old. Yeah. And until I realized and started treating life as like, you know what, I could have died before Cindy. Right. Yeah. Doesn't really. And, you know, I could. Tomorrow I can be hit by a bus or whatever. Like, I know people talk about that and say that and. But once you think about it that way, you kind of tend to treat. Do things a little differently, prioritize different a little bit. I mean, some of it's unconscious. Right. Like, it's not. Like every day of my life, I'm thinking, like, you know what, tomorrow might be my last day. But, like, subconsciously, like, you don't. You change your priorities in some ways, like, you know, when you're faced to decide on, like, should I spend more time working on this or should I hang out with my kid or whatever, you know, I don't know. I mean, I'm guilty. I'm just as guilty, though, of, like, making the wrong choice in those moments. But we're all human. Yeah.
So you mentioned you joined a grief group. How did you even know to do that? I'm kind of curious.
Cindy, in her last few weeks, she was at home. We had a hospice nurse come in. And, you know, these people, they're just great.
They kind of.
They take care of you. And I think they suggested it and they even told us, like, who to go to and see. Yeah. And I still talk to some of my friends from that group. And yeah, we've become lifelong friends, you know, but, yeah, it's. Yeah. The whole process of grief, like, in the years, you know, it's just. It marks you. It's like it's part of your life, you know, in many ways, I'm better for it. I think having had that experience younger, knowing, experiencing loss has made it easier for me. It's given me Clarity and like, you know what's important. And so yeah, after she died, you know, I think things, there were some rough spots for sure. Like, you know, raising kids on your own is no easy thing. But we made it through and kids are doing great. They're adults now.
It's tough. Tell me what the kids were leaving.
One's in college, be third year in college and computer science.
Okay. Okay.
Yeah. The other one is, yeah, I have mixed feelings about that sometimes because of the market. But the other one is working full time job. He's a car mechanic. And sometimes I think of myself like when I say that like, you know, there's that part of you as a parent like, oh, he, you know, he didn't go to college or whatever. But you know, I'm really proud of him. He's just, he's one of those kids I don't really worry about because he just, he's working his passion. That's what he loves. He's, you know, that's another key. Learning is like when you're doing something that you love, you know, it's, the possibilities are limitless. Right. So, yeah, so he's doing great. He's got, you know, good social group and loves. I'm just not worried as a parent. Yeah. Yeah.
Not that I have kids, but I imagine, yeah, that's what you want.
Yeah. It's huge. Yeah. So it turned out all right.
It sounds like you found the right support and with your resilience and self determinism, we're able to get through that. And thanks for sharing by the way. I know that's extremely personal, but I really appreciate you sharing. It gives way more color context to like just how much you were going through from Oracle, inventing things like building new things, like creating new paradigms for social media before it was a thing. And then here where you're now going to Atlassian, helping them come up and scale and then you went off a couple hops later, went off to start your own thing.
Yeah, that was a weird one. That was, you know, kind of one of those things where, you know, you, you find yourself, you're just kind of like blowing in the wind. I mean, I, I, that was never on my bucket list of things to do. I never had this desire, you know, entrepreneurs out there, people who founded companies, most of them have always wanted to do that. Most of them were like, from the day they were born, they're like, yeah, this is what I want to do. Right. I was always afraid of it. I was like, I don't want to do that. That's not. Sounds really hard. It wasn't until the pandemic. During the pandemic, after, after Atlassian, I went over to LaunchDarkly Lunch Darkly. I I LaunchDarkly was a, was co founder of one of ex Atlassians. So there are a bunch of Atlassians there. I was in Oakland. I thought when I left Atlassian it was like a. I'm. I'm gonna slow down a little bit. Right. I want to ride my bike to work. I wanna just like whatever, like just. I still want to do fun, cool, hard stuff, but I just don't want to be hardcore about it. Yeah. So I was a developer advocate also at Launchdarkly. Anyway, it was great. Good group of people there. I'd really gotten into coffee a lot there. I've always been into coffee. But there's a lot of, I don't know, the engineering team there is pretty interesting and there's a few of us and I'm sure there's a lot of engineering teams who are like this, just like. But they're like a lot of coffee nerds.
Coffee culture shops.
Yeah, yeah. And we had a bunch of good coffee shops nearby in Oakland and we would go every afternoon and grab some good coffee. And then the pandemic hit and I was like, oh man, it's sucks, like getting the good coffee. Like, I can't do that. So I bought myself a espresso machine, got the whole setup and I as with anything, you know, these things are really expensive. And I'm like, you know, I'm going to nerd out on this stuff. I'm going to learn everything I can. And so I, you know, I bought the grinder, I bought the espresso machine and then I just like again, design principles in mind here, like thinking through like, if I only drink a cup or two a day, why would I want to put my $20 pound of beans into the grinder where it's exposed to air and light and within a week those beans are stale and they're not as good anymore. And then at the time people were talking about single dosing a lot. And so this grinder I was just looking at, it's like, this is a home grinder. This should be like a single dosing grinder, except it had this big hopper on it where you can put the whole bag of beans in there. So I thought like, huh, you know, and I, at the time I was really into Reddit. I'm an old Reddit user. I think I'm like 18 years now or something like that. And there's an espresso subreddit that's really popular. And I started posting in there and it was like during the holidays, I was. I took two, actually. I don't know if we closed down or something. I don't know. I took a few weeks off and I was like tinkering around and thinking, oh, I should get a 3D printer. I realized the 3D printers are really cheap now. Like, 200 bucks, you can get a 3D printer. And so I got a 3D printer, taught myself how to use Fusion 360 CAD design, and designed single dosing hopper. And I started sharing the designs on Reddit. And that in that espresso subreddit, people were like, that looks really cool. You should. You should print. Yeah, you should print that out and sell it on Etsy. I'd buy it. And I thought, huh, that's cool. Like, maybe I should do that. And so I posted it, I created a listing on Etsy, decided, you know what, I'll put it. I was thinking, originally, 20 bucks. But then I looked at other coffee type gadgets that people are creating on Etsy and people are pricing that are really high. Like, so I thought, okay, I'll sell for 40 bucks. Yeah, 40 bucks. And I did all the math, calculated, like, my cost of goods and everything. My cost of goods, around $1.25. Okay, so it's a huge profit margin. So, yeah, that first year I started putting it out there. I think within that first year, I sold, I don't know how many. I think like 2500 that year.
That's amazing.
Yeah, it was great.
Boom, entrepreneur.
Yeah. And it was like, literally printing money. I mean, like, you know, I didn't have to design each one. I had one design. I would print them four at a time. I actually ended up getting two printers going simultaneously. At, like, high point. I would have like 20, 25 orders a day. And to a point where, like, over the summer, I hired my own kids. I said, this will be your summer job. Yes.
You know, that's great.
That was a mistake though, because, like, I told them, okay, you know, because the profit was so high, I was like, okay, I'll split the profits. So for each unit, I told him, I'll give you $14 for each unit that you print and package and send out. Right? It takes like, yeah, it doesn't take that long. Like, each day they maybe spend like 40 minutes.
Oh, so you were paying them like, they were.
They Made. They made a lot of money that summer, intern. Yeah, they made a lot of money that summer. And meanwhile, because they're my employees now, I actually had to pay taxes, employer taxes, because I wanted to do it legit so that they can actually like put it on the resume or whatever. You know, I thought like, okay, that was a bad choice. I should have paid them under the table. Yeah, yeah. But anyway, that was a really. So that whole Etsy business ended up like, you know, a six figure business in like a year. So I was like, wow, this is really easy. This is the first time I've done a side gig or like a side hustle. And it really was a side hustle where it's like, you know, kind of there's a little bit of work, but not. And I thought this is really easy because I mean, this really comes down to three things, right? You listen to your customers, treat them well, you ship on time, all the time, and you create a good product and iterate and make it better over time. Those three things, those three things are the secret to every successful company. I mean like literally, that's the, that's the ingredients. Those are the three ingredients, right? If you're starting a company, those are the three things you need, right? And so I had a lot of confidence in running that company. And I get a call like, I don't know, towards the end of the pandemic I had a call from Eric Whitman who also worked at Atlassian. He was a general manager for the like the BitBucket side and all that. And he had left and eventually I think he's the CEO at VSCO now. And anyway he called me up and said, and I'd known Eric, but we weren't like great friends or anything. I think he just, he knew about me and we'd had a few conversations, but he called me and said, hey Rich, are you interested in being a co founder? Caroline Clark, who also worked at, at Atlassian, is starting a company and she needs a cto, a co founder to help her run it. And I was asking, well, what is the product? What's the idea? And it was around demos, like creating demos, like product demos. And she was approaching it from the VC side, but she had seen a lot of bad demos, a lot of people like doing demos using PowerPoints. And she just thought like, you know, there's way better tools or way better ideas of how to do a demo. And so all my experience, like early days at PeopleSoft when I worked with sales engineers, I was crafting demo servers basically at PeopleSoft. But I'd worked on this product called Enterprise Portal, which allowed us to skin the demos to look like the custom. Like it was like we put a logo, we changed the color scheme, all that software underneath that to tailor all that was stuff like I'd helped write, but that was like real life software. I thought about demos in general and I look at the thread across my entire career of what demos meant and to me that was the one thing that tied everything I'd done in my entire tech career was demos telling the story of software. Because I had worked, yes, I had done all these things. Like I was a implementation consultant at PeopleSoft, I was a systems engineer at Hewitt, I was dev advocate. I had all these things that were like interesting jobs. But what I always found myself doing was crafting some sort of story and crafting a demo either for someone to present or for me to present or for something for like a conference talk or whatever. And at the end of the day when you software is just like bits and bytes and pixels on a screen, it's meaningless to people unless you can tell people what it does, what problem you're trying to solve. And so Arcade was a natural problem for me to work on next and to figure out how could we take that problem of how to tell the story of your product and prioritize that and make it easy for someone to do so. Yeah, there's again, perfect storm. After launchdarkly, I went to a company called Mural Mural.
Merrill versus Miro.
Yeah, exactly like, oh, and then need to collaborate.
Online wars. Right.
And then figjam came on board. Yeah. And then. Yeah, it was like great product. It was the pandemic effect where these companies just like this blew up.
Yeah.
Like they went from like, I think like less than 100 employees or. No, actually less. Smarter than that. Maybe 50 employees. And then all of a sudden the next year they grew up to like 400 employees, 50 people. And they were Argentinian based company, but most of that growth because their investors were in the US they decided to hire in the US and majority of those people are getting paid more and stock options and everything. And so set up a really bad culture. And in the meanwhile, the Argentinians were still running the, the thing. Right. So like engineering and all that. So it was like just. It was, it was, it was rough. It was, it was the. It's the only place I'd worked for such a short time. I worked there for four months. I couldn't stand it. I was there to kind of help them bring up an ecosystem for integrations and third parties. It was, it was a shit show. And so I was in that and so I wasn't really looking to get out necessarily. But like, you know, Eric called me and then that landed in my lap. And like, now you think about it, you know, I know that was not my. One of the things I wanted to do, but like that my experience at Mural plus coupled with my experience with Etsy, like, kind of combined into like making me want to be an entrepreneur and want to be a co founder. And Caroline was the perfect partner to do it with.
Her skill sets complemented very much.
Yeah, yeah, yeah. She's, you know, I was a technical kind of product person and she was brought in the business and the VC experience, which was super important since we were VC funded or are VC funded. Yeah. And then just built and built and grew and built and grew.
Yeah. Tell me that the timeline against that story of growth.
Well, the nice thing is, like we had our problem and our product was very clear. We didn't really have that many competitors. And there were some competitors already. There's a few, like there's Novatic that had been there maybe a year before us. They were like the only notable one, but their approach is very different than ours. We wanted to start. So the big question in the beginning was like, what kind of demos you want to create? Like product demos. Right. There's the sandbox way, which is like build the sandbox of the product. It's a real product. Kind of like what we were doing at PeopleSoft and Oracle. That's really hard. Don't want to do that. And that's too deep anyway. Most of the time, especially from a marketing standpoint, you want a glimpse into how the product works, but you don't need to do a deep dive. I had this gut feeling that images and video was the way to go. It was the most portable format that we can use on any device. It's pretty well known how to work with images and video. It's not like rocket science. We had competitors like Novadic, for instance. They were doing something pretty novel as well. They were scraping the applications, the HTML, JavaScript and the CSS and basically building kind of like a hollow product experience of the app. Of the app. And I thought like, God, that's gotta be really hard because, like, just think.
That sounds really hard.
Think of the permutations. I mean, like, you worked at workday.
Work.
Workdays. Workday's product is pretty crazy, right? Like underneath, like the, the how do you. You could. Yeah, you can obfuscate it.
So yeah, like there's a lot of problems.
You could. It either goes really bad or it works. Right. Like you can't. I've. I've been around long enough to know that not all products are built the same way. Right. And. And some things could be really brittle if you do it that way.
Okay.
You know, even just things like experiences like one page apps, single page apps, that was the big thing. Right. Like a few years back, like I worked on Trello and Hipchat. Yeah. Single, traditional single page apps where like. Yeah, this one big fat client that had a lot of HTML, JavaScript, CSS on it and things changed dynamically and like that is going to be really hard to recreate as a hollow static app. Right. And so. Yeah, sure.
Were you looking at that and then you decided, okay, we're gonna.
No, I kind of knew. I was like, I knew like that would be really hard and I don't want to. You know, and you're. As a startup, you have to move fast and you don't have time and so you go with what you know best. Right. And our bet was on images and video. That turned out to be a great bet. Yeah. And it's much easier to work with and it was more fun to work with, honestly.
Yeah, it would imagine.
Because now like it's integration kind of bs. Well, you could also. Not only are you just. You're not stuck on like demoing applications, you could demo anything you want.
Different market categories.
Yeah, exactly.
Wait, sorry, go ahead.
Yeah, so like, you know, we ended up being kind of like a multimedia sort of compilation app. And our ux, our onboarding, our onboarding experience like from zero to one was super fast. It was pretty novel.
Less than five minutes or something.
Yeah, about less than five minutes. You can get a demo going pretty quickly.
So that's really cool because time to value is everything in software and especially nowadays because it's an attention depending on.
Who your ICP is too. Right. You know? Yeah. I've seen how hard that whole onboarding thing can be depending on your product and your company. Like at LaunchDarkly, their biggest issue is like how do we get someone to put a piece of JavaScript onto their application? Right. Like no one wants to do that.
Nobody wants to do that.
Yeah. And that's really hard. Like, you know, you have to have. It's kind of a leap of faith. Yeah. Yeah.
Time to value. LaunchDarkly. Getting somebody to put JavaScript, you know.
I'm familiar with the challenges, a lot of challenges with onboarding and product complexity. After all the products I'd worked on in the past and the audiences that I to support and then for this go around with Arcade we had a very clear ICP and that was the marketer. And you know, knowing what you know about marketers, like they're not technical, they would be very frustrated with a product that was tech that required technical know how they would easily just jump to jump ship or pass it over to their engineering department. And that was exactly what we were trying to avoid because at the time like so our, our initial product, what we wanted to do, our goal was like we wanted to end up on people's landing pages on their homepage and their landing pages.
Oh yeah, that makes sense. So there's a variety loop for acquisition.
Yeah. So the demo would land on their homepage or the landing page or both. And the way they're the ones who did accomplish doing that like putting together a demo, it's usually a collaboration with their engineering department. Slack had a great interactive demo of their product product on their website that really early on which was really great. Like you can click on the channels and it looks like it's, you know, it would be the real thing or at least approximation of the real thing. And so people got it. And so that was kind of like what we were modeling. But we knew that, you know, not everyone has an engineering department they can work with and oftentimes that's like a month, two month, three month project. Right. Just to accomplish. And so we knew that that was our bar to hit. We needed to beat that. And so luckily the good thing was like the technologies were all easily accessible in place to build a product that was going to be easy to onboard onto, easy to use, easy to put together something. Can't guarantee, guarantee that what you record and put together is going to be stellar. I mean a lot of times this subject is really going to define how good the demo is.
You can only put so much lipstick on a pic.
Yeah, exactly, exactly. But the value was like people could create these things easily without the help of anyone. So people love it. And then new use cases start started to emerge. It wasn't just about demos. People were like thinking, you know what, we're going to redo our documentation with this. Like you know, what was it? Gitbook. Gitbook is this. I don't know if you're familiar with Gitbook. So Gitbook discovered us just randomly and we were a customer of theirs but like, they discovered us, I think it was during our product, second product launch. And they. Yeah, so Gitbook had discovered us after our second product hunt launch. And I think after, during that day that, when we launched, we launched on Thursday, I think they signed up for a subscription. Their lead designer recorded a demo and posted it on their website like that same night. And then he went on vacation on Friday. So I didn't even get to call him because I tried to reach him because I was going to tell him, like, hey, you're subscribed to our product. We have an arcade logo on the, on the bottom right corner. And I don't know why we made it an option to turn on for variety reasons. Right. So like, you know, even though he paid for it, he didn't turn it off. And so I thought like, maybe he wanted to turn it off because he paid for it. Yeah. But he was gone for a couple weeks and so I ended up getting a hold of, of one of the founders, the founder of Gitbook, and he said, he says Scott was gone or he's on vacation. And so anyway, no big deal. They left the logo there.
Wait, that's great.
Yeah, it was great.
That must have got you. Wait, tell me what happened.
It was great. So they were a great partnership and a few months later they were launching a new thing. They were launching an ecosystem for their integrations. They were creating an integration point for third parties to be able to build additions to Gitbook. Right. And they told us, they notified us and said, hey, yeah, we created one for arcade. We didn't have to create it. They created it and it was wonderful. It's like, yeah, so like, it was great. Things like that would happen. And then we realized, like, the way Gitbook uses it isn't for like homepages, product landing pages.
It's.
It was so that people could show how to's. Of how to do something. Instead of writing about or showing a bunch of screenshots and documentation, people would record an arcade of how to do something and they can interactively do it on the documentation page. Yeah. So today if you look at Gitbook, you look at actually not so much gitbook, but if you look at like retool.
Oh yeah.
Retool is a huge arcade user. If you look at Retool, most of their pages have arcades on them. They replaced all areas where they have screenshots with arcades because it's easier to replace one arcade than replacing 10 screenshots on a page. I could Just re record that arcade. Even if you did a reskin of that product, it would be a pain in the butt to rerecord all of them. But it's pretty easy to re record so. Yeah. So you know, I don't know those.
First few years, timing like. So you came on board.
I came on board in June.
This happened.
We came on board in June. Our first customer was Carta. Yeah. And then they put their first arcade, which the first arcade was, was like basically hand woven by us.
It was, you got to put something out there.
Yeah, they put that out on their, their product landing pages and they, their in their blog posts in like August, September. Pretty quick.
Okay, pretty quick. A couple months.
Yeah, a couple months. And then we had our, our first product hunt launch in September I think.
Wow.
Yeah. And. Oh yeah, yeah, yeah, yeah. We knew like and then I mean the product was easy. Like there wasn't the iterations, we had the things. I don't think we pivoted on anything. Everything is just like building iterations, building things better and better. The first engineering hire or founding engineer that we hired, we hired him in August, September and he and I were building, but he was building the analytics part of the product which we knew that was going to be huge because people need, you know, you're selling to marketers. Marketers need to know the metrics, they need the data, they need to be able to measure the effectiveness of these campaigns. And I was continuing to build on the arcade like the demo side and then we just grew from there and like year after year after year. It's just how many years? I was there for a little over three and a half years.
Okay, so you saw rapid growth then?
Yeah, yeah, yeah, yeah, we saw rapid growth during that time. We, we raised a pre seed, a seed. And then our series A was just before I left. Yeah, we talked about revenue.
I don't know if that's public but.
Like I think I can talk about revenue. But end users, I don't even know. We never really counted users as much like we didn't measure ourselves by users, we measured ourselves by arcades, number of arcades and just the metrics of like how quickly people would put them out, publish rates, I don't know what else. But yeah, there's, yeah, it was fun, it was a good ride.
So that's really cool because that's the through line through your whole career back to hey, we're creating this way for non technical people to make beautiful demos and tell stories of software. That's what you were saying. Yeah, that's really cool that you were able to leverage all your experience and the creative juices of like even setting up this podcast and all that. Right. Like, so I'm kind of curious, what is your philosophy of storytelling in software? Because that's a really interesting topic.
Yeah.
That's basically what you baked into this product.
Yeah. I mean, a lot of it is just like in this tool. Arcade was an enabler for that. It wasn't the thing that was going to. It wasn't like your story, your product is going to tell itself. Right. We try as much as we can to help you with that, for sure. Like, the introduction of AI, for example, was clearly a way to. Oftentimes you record an arcade, it's a blank page still. Right. You record all the screens and the video and the interaction. But what is your story?
Right.
So with AI integration, we actually pre fill that story, whether it's for a marketing use case or for like a sales use case or tutorial or whatever. Right. And you kind of helps, you kind of fill in the blanks a little bit. Yeah. You know, we saw lots of different patterns. And I won't say, like, I was completely. I completely consider Arcade done by the time I left. I mean, the product was good. It is good. Still, I think where, you know, I think what would be great is if it, if it could. You know, I always think like, you know, like, creating YouTube videos. I've created a number of YouTube videos and they're really hard.
It's hard.
It's really hard. Right. Like, content creation is super, super hard. The creativity aspect, the. The content. I was just like, the mechanics are difficult.
Yeah. Getting all the equipment, like.
Or the story, like. Yeah, like, I mean, I oftentimes like, want to tell this great story, but like, like, how do I start? You know, and music that I put in, what are the cut scenes and the B rolls?
Lots of decisions.
So, yeah, I think, you know, an arcade is just a part of that story. So, yeah, it's a product demo. But like, if you want to tell a full story, like full demo. Yeah, it's. It's more than that. It's like, it's. It could be. I go back to like, I used to love these. I think there's this company. I think I forget the name of the marketing company or the ad agency that did these. I think it's called Sandwich. You know, Descript.
Yeah.
They used to have a really great ad. Yeah. So Descript, they had this ad on their website for a long Time after they come out and they were a success and it was just a story about what Descript is all about. But they didn't show much of the product they were talking about. Basically just showing all these different characters, different colors, different. It was really cool. It was very creative.
I'll put it on the YouTube.
Yeah. And I think, I love that. I love when the story of your product extends beyond your product. Right. And it could show the humans behind it. It could show what you're actually trying to do, you know, how you're trying to whatever, improve your world or you know, your customer's world somehow. I love that. And I know not everyone's products speaks that way. I think, you know, Arcade is such a versatile tool. It's never going to be able to tackle that sort of problem. But like, I don't know, I have this hope that like it would be great to be able to produce something like that. Right. Like where you could, you know, because I want to be able to create YouTube videos without recording and having experiences that you're, you know, that you want to tell the story of that. That's one thing. But like that whole editing experience, oh my God. Yeah, it sucks. It's like it makes you not want to do it. Yeah.
And I think what it is is there's so much cognitive load of the decision you have to make what B roll. And then if you have a high bar of excellence, what B roll becomes maybe a one hour search music for especially for the hook too. Like there's lots of decisions.
I'm sure there's a lot of pre planning and process that will. That helps with it. Like having a shot list and knowing a lot of that ahead of time. But like how often like for, I don't know, I'm not even a content creator but like I, I'm not even aspiring YouTuber. I just like creating videos once in a while and yeah, but like, oh my God, it's just so hard to create something good.
Might be your next product idea.
I saw a friend of mine introduce me to, to a YouTube channel just today and, and he was telling me about like how great the videos are. They're all AI generated. I was like, okay. And they're like, you know, AI generated scenes and the music, everything and. But there's a voiceover and the voiceover is a human and this person's. The videos are all stories, like engaging stories. Like I watch this thing about aging and it was just like mesmerizing. Okay, so maybe AI will do it. But Like I don't want that. I still want some reality in my.
So that helps me understand more and contextualize the breadth and depth of your career leading up to Arcade and building this fast growing application that has helped lots of different teams tell the story of software and their own software. And I love hearing that philosophy. Thanks for sharing it. So you left. Why did you leave and what are you doing now?
I left and that was recent. Yeah, I left in February and I made that decision to leave six months ago. Yeah, last fall. I made that decision leave last fall. Just, I know a number of things. I realized the journey of Arcade was super great. It was fun, but it's also humbling. Right. Like there you learn really fast what you're good at, what you're not good at.
Absolutely right.
And you have to be good with that. Right. And I mean I, it's not a surprise to me what I'm not good at because honestly those weren't things I ever focused on in my career. Like, I think this next stage of Arcade, you know, post series A requires just a different type of leader. Right. Like to grow the company, to scale the company. I'm a builder, I like to tinker and build and in many ways I think I'd be, I, I don't think I would be great for the company at this stage. And that like that takes a level of self awareness. Yeah. But also it was easy too because I already been kind of thinking about like at some point I kind of want to just either slow down or get out of tech on. It's a little bit of a dream, a pipe dream. Right. Like, I mean, not that I'm tired of tech. I love tech. I mean I was just coding right before this.
Yeah.
For fun. But 30 years in, doing one thing is a lot. And I'm at that stage where I'm ready to do other things and so wherever that takes me. So right now, the past, since February I've been kind of in exploration mode. I've been a part time barista a couple days a week.
What'd you call that by the way? When you were just doing the barista thing? You called it some kind of job when it's like a retirement barista job or something.
Oh, what was that word you used? I forget, I don't know, I don't remember. But I'm a. Yeah, I say a two day a week barista. And much of it is just like I went to Japan after I retired and I kind of geeked out on the coffee scene. Over there. And I got back, I decided, you know what? I should just be a barista for a little bit. So I work at local specialty co. Coffee place.
Yep.
Yeah, yeah, yeah.
That's where we met actually. Jake intro us and me and you met there.
Oh, yeah, yeah, yeah, yeah. And so. So yeah, that's. That's. That's been fun. I've been trying to ride my bike more. Yeah. It's not going well. I took on climbing, so.
We gotta climb together, dude. It'll be fun.
Yeah. I think you're. I'm way out. You're way out of my league. I like I'm climbing.
It's just fun.
Yeah. It doesn't.
I don't care about, like, it. When. When you just climb with people, you don't. At least for me, I don't care about what difficulty you climb.
Yeah.
About what kind of energy you bring. It's just a good person.
Yeah. Yeah. So I'm enjoying that. I do that like once a week. Not. Not enough, but like just once a week right now.
Photography, right?
Photography. Is that recently? Yeah, that's just more like. I've always been a photographer. I've always looked at cameras. I've had a camera since I was in high school and always taking photos. And I got rid of all my gear. Like, I don't know when iPhone cameras became really good. I'm like, what do I need these for? And then now I know why I needed those. It's just so different taking photo with a real camera with a viewfinder, looking behind a lens, through a lens. Anyway. Yeah, it just goes back to my, you know, artistic kind of design fetish, I guess.
And it really is just like storytelling through a different medium.
Yeah. Yeah. And honestly, that's the thing I'm trying to balance right now is it's a hobby. But I think, as with a lot of things, I feel like. And I'm not alone in this. I know I'm not alone in this, is that oftentimes a lot of people take a hobby and try and figure out what they can do with it either, you know, have a goal of, like, making money with it. Another side hustle or growing a YouTube channel or your followership on social media or whatever. I just don't want to fall into that trap. And I. I feel like my. Sometimes I feel that way. Right. Like, I. I just. I think I'm just wired that way where, like, I need to see some sort of progress. Progress. Validation.
Okay. Yeah.
Recognition for the things that you do.
Yeah.
I Don't know.
I, yeah, that's actually totally human.
Yeah. Oh, I know.
Every human wants to feel confident.
Yeah.
They want to feel like they belong. And so there's, there's, there's always this sense of self. And you're, you're the hero in your own story. Right. Everybody is. But you also have a social self. Like, who are you in relation to everybody else?
Yeah.
Like, you can't exist without everybody else. So I actually think that's quite normal. But it's also interesting that you, like, you're like, well, I don't want to fall into that. Like, I know that, but I also.
Yes and no. It's kind of weird, like, now having been out of it. It's like sports, right? Like, the minute you're taken out of the game and you're sitting at the sidelines, first thing you want to do is get back into it. Try and find your way to get back into it. Right. I mean, I'm not itching to get back into a job or take tech or anything, but, like, I can't help myself. Like, creative drive. Well, yeah, it's creative. And also all my experience from, from tech and especially running, you know, helping run a company, I can't help myself lean into those opportunities. You know, I'm helping out another friend with his startup, and I spent two hours with him on a Friday just ideating and talking about. It's like, what am I doing this for? Like, why?
But was it enjoyable at the time?
Yeah. But then, you know, you think about it, it's like, oh, man, is that the, Is that what I wanted to do? Maybe. Yeah, maybe. I don't know. I, I, I, I go back and forth. I mean, you have to scratch your own itch sometimes, but at the same time, it's like, I don't know.
Yeah, yeah, yeah, yeah. Are there other itches that I'm not feeling as much?
Yeah, that's interesting.
Okay, so wait. I know this has been a lot. I think this is a good point to maybe, like, summarize and end it. But, Richard, you've had, like, a very inspiring career. And I'll say it for myself. When we met, you inspired me, actually. Like, even Claire, you gave me some feedback on this. I was listening, and I have tape now of your feedback. I'm gonna go back to that and look at that 10 times, and you inspired me to get into the details. And when I first met you, I was like, man, I want to be rich at some point. Like, I want to be able to Build things and you know, in 20 years, still be building things. Like, I just love the thought of that. And so, yeah, I just wanted to say, like, when Jake introduced us, it was very timely because I was thinking about the next problems I wanted to solve. And then every entrepreneur has a certain set of skills, right? And I was just like, I think I'll probably always need a technical co founder because I'm much more on the product side. I love, I could get into code and stuff like that, but my code's shit for sure. I'm never going to be a performance engineer for sure. I could prototype shit and get things working, but like getting into production, different.
Story, people say that's different. AI makes it different. Yeah, people say that about me all the time anyway, so.
No, but like, I just wanted to say like, your story super inspired me. Just like how you handled the hardship, your self determinism, your resilience to get through all that and then go make a dent in the world, like that's, I feel like that's what I want to do. So I really appreciate you sharing the story with me and with everybody else who could also learn from getting the details. So thank you. And then also another shout out because Rich probably won't talk himself up. Rich is dope as fuck. Like he's set up this pod, so anything like this whole set, great. And now I have something to work with for the future. He's helping me with photo shoots. He's given me another lens on how I might look at a scene and that in itself is so valuable. So if you need photography stuff, videography stuff, if by the time you watch this and Rich is still offering any of that and he's still trying to scratch that itch and he hasn't got back in the game of tech or whatever, hit him up. I'll throw his Instagram and his website on, the YouTube links in the show, notes and stuff like that. But Rich, is there anything you want to wrap up with and like, let people know where to find you? Like anything you're doing, whatever.
Yeah, no, I. Yeah, come visit me at highwire Coffee. I guess I'll make a good coffee. No, I don't have anything other than just like live your life, life as best as possible, you know, like, what.
If there was a 22 year old rich coming out of college watching this? What would you dumb.
Ooh, good one. Don't waste the opportunities, you know, don't spend 14 years at a job, you know, that you could have been doing on your own. And, yeah, I think that's. I don't have any regrets. I wouldn't say that's a regret. Like, working at Oracle and PeopleSoft, I think that led me to the next steps, honestly. So, yeah, I mean, I tended to be looking at my career like I tended to be in the backseat most of the time. And luckily it was good. I would probably suggest to move up to the front, you know, and maybe even get towards the driver's seat and figure out how to control, like, and how to. How to do something more meaningful maybe with your career. I don't know. I was lucky. It was all meaningful to me. But, yeah, in hindsight, I think about it, it's like, oh, yeah, I could have done that. I could have done this. But in the end, I'm pretty happy where I am. So, yeah, no regrets.
It sounds like the lesson there is learn from what you've done, but also don't ruminate in the past.
Yeah.
And try to live with no regrets.
Yeah. Yeah, exactly.
That's awesome, man.
Yeah.
Well, thank you for coming on the pod. Yeah, this is great.
Sure thing.
And yeah, everybody, you could all catch Rich on all the links. I'll add to the show notes. And I hope you all got a lot out of this. I have. And to my future self, hopefully. I'm still getting the details like Rich taught me. Clarity is going to blow up at some point.
Yeah, I hope so.
And I'm going to get this feedback, integrate it, grind on the UX as we really clear.
Yeah, I hope so.
Thank you.
All right, take care of.
