Aaron Harris: The Origin Story

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Welcome back everybody. The most official unofficial stage and tag podcast in the world. In the world. In the world. I think we need to get that on a shirt. Like that's the only way to make it like I want to make it longer though. Where are your shirt? It's in my bag. Yeah. Although to be fair, today we have little cue cards. We do have cue cards. Which are very rare.

Very rare. And lots of stuff written on them. I'm excited to see what's on them myself, honestly. I really am. So this is this is gonna be a a fun one here for me. well I like I most of it. It's pictures. I can get most of it. It's like and then I can kind of infer what the what it's trying to say after I get a couple of the words. You know. Aaron's already regretting being I'm regretting this decision. Yeah, you you can just leave actually. Yeah, you can just get out of here. Aaron Harris, CTO, Sage, the man, the myth, the legend.

I don't know. What do you what do you like to go by? just Aaron's fine. Just Aaron? Just Aaron. Not the whole My kids call me El Guapo. Really? No, but I wish they would. I like this. And then yeah and then it just got squashed. we can we just the whole podcast to be the story. Yeah. We'll do I would love to tell the story of El Guapo, but I'm I'm sure that's not what the listeners came here for. No, next time.

Next time. Yeah, next time. You you you laid the bait, so now we have to come back and see on the next and we can do a whole three hours on it. Of course. Yeah, yeah. Of course. Of course. You're gonna have so much fun, you're going to want to come back. Okay, all right. He's not. That's that's a challenge. Well yeah, well the podcast isn't over yet. That's right, and there is an open bar just off screen that no one can see here. we're actually in in your personal living room, are we not, Aaron?

But you're in a room that I spend a lot of time in. Yeah. You can kinda see it. It does look like kinda like a living room here, but beside the point. So we want to take this a little different route, if it's all right with you. Minimal prep, by the way, across the board here for everybody. Everyone always loves to hear your take on the technology, AI, you know, the the more technical components. Which is great by the way. Which is phenomenal. Which is great. We didn't want that. We don't want that. I think that people really want to know who you are as a person, how you got to where you are.

We'll call it what you want to call this? Maybe like an origin story? Origin. We can go with the origin story. Aren't origin stories normally about the bad guy? sometimes, but not always. Okay. Sometimes it's about the good guy. Alright. Sometimes. Maybe. I don't know. Don't don't quote me up. Now that you said this, if you were a superhero, who would you be? A wasp. I I don't know. That's the weirdest question I've ever thought of asked. Perfect. If I were a superhero

Kinda like Superman. You like Superman? Because they're like he's invincible. And he can fly. see. And he has got laser eyes. That is all true. So I always put myself like, who could a actually be a human? So I thought Iron Man, Batman. Iron Man's pretty cool. Iron Man. He doesn't actually have any unnatural powers. He's just very smart. And very technologically savvy. Yeah. Mm hmm. Who would you be? Iron Man is. Iron Man. Doug, how about you? Boy, I don't want to repeat, but

If I had to f Superman is kind of You can't copy Air That's why I I don't want to repeat. It's like ordering the same thing. Ten million. Like literally. Well that's that's that's a bit much. That's a bit much. I don't know if we're gonna do it. I would also be Superman. but I would I would pay to see a Superman or Superman movie. Now that. That would be a good movie. Are you listening out there? Are you listening DC?

They're they're they're Abbott fans of this podcast, so yeah, executives that we're T C. But getting to know you little more, Aaron. So a couple rapid fire questions just to kinda warm it up, right? Get you get the get the blood flowing, if you will. Morning person or night owl? I used to be a night owl. the older I get, the less true that is. And it's sort of transitioning to being a morning person. I would say that I'm neither at this moment. so

Y don't catch me at either end of the day. You're not gonna get You're just not gonna start the fist these days. Yeah. Yeah, kids will do that to you. I I get it. I get it. Coffee tea, neither? Black coffee. Black coffee. No no messing around, hot, cold. No just both well, hot. Hot black coffee. I actually I do like iced coffee black in it when it's hot out, yeah. Doug, pull us back in. Well then you might have to I've you might have to ask Holmes about this one, but

You know, I if I'm not mistaken, Aaron, you weren't just born to be the CTO of Sage. You you got there. That's what everyone knows you as. It's can you kind of take us through the steps from, you know, early career, what pathway kinda led you to where you are today? Because maybe you always have been, the kind of tech guru, I don't know. but I think that's a really interesting pathway for people who are looking at, you know

How do I further my career? What should I be aiming for? How do I take some steps, some risks? You know, it's kind of give us the pathway of where you got. Yeah, I I I think I I would preface this by saying that I have a an unusual path. I I often joke that I have a very short resume. when I was working on my master's degree, I started a little software company doing accounting for home builders, right? So like construction accounting.

It's called Contractor's Companion. It was really, really cool. I I my plan was to to crush Timberline. Timberline at the time was was purely DOS based. Timberline wasn't owned by Sage at that point. I don't I can't I don't I don't know exactly when Sage acquired Timberline, but I don't think it was owned by Sage at that point. and I I built a Windows based accounting package for home builders, right? DOS based? Mine was Windows based. Your Timberline was DOS based.

Okay. and my killer feature was I automated the loan draw process. Right. So depending on which construction lender you worked with, I actually like got their forms and automated the way to fill in the forms for them to get their construction draws. Anyway, big deal. I'm probably spending too much time on this this part of it. the f fundamentally I got offers by investors to fund it and I was too chicken.

And instead I took a job, like a really secure job, like with a with a with a path for the future that was well laid out with Arthur Anderson. Okay. Some of the audience will be chuckling right now. this was this was nineteen ninety seven. Do you know the story of Arthur Anderson? I do know the story of Arthur Anderson. We we had a discussion last night that we can't talk anything like pre two thousand seven.

With me. No, I was born in ninety nine, but I at least want to be cognizant of like when these events are taking place. All right, long story short, I I went to work for Arthur Anderson. I I'm not responsible for its downfall. I left before before Enron happened, before WorldCom happened. fundamentally, like i it was a f great place to work, but it just wasn't for me. I I you know, I really was at the time, you know what No, I w I worked

For the CIO. And we w my particular team kind of we did best practices on new technology. So, you know, if if some new technology emerged, we would do a little research, we'd build prototypes, and we'd, you know, we'd we'd go and lecture to consultants on, you know, here's this new technology, here's how how you can use it. So it was a very academic job. and it was fun, but there was

It was just it was slow and there wasn't room for me to be creative. So so I think what some people would think is like you I know you have an accounting background, but you've always really been technology focused from the from from I never in a million years thought that I would build accounting software. I I've I've always been into computers, I've been coding since I was a kid. I I always thought I would have a career in technology.

now in hindsight it all makes sense. somebody convinced me when I was in college to do a bachelor's degree in accounting. I was I was I was a CS major at the time. And the con the the convincing was essentially, hey, d do a bachelor's in accounting and then do a master's degree in information technology, and that'll give you just a great foundation for a great career. So so I I I

It was kind of a weird moment where I decided, okay. I'd never even considered it before that. But I had always wanted to be in technology. Whoever gave you that advice obviously you owe a lot to at this point. Yeah, yeah. so I was working for the maintenance department at the university, and the conversation probably happened while we were unclogging toilets.

That was gonna be the first guess. That was the most common, that was the most common maintenance call that we had to deal with. It was unclogging toilets. So probably happened during that. No, let's get into the toilets a little bit. Okay, let's get back on track here. So I I I worked for Arthur Anderson for two for two years. One of my colleagues at Arthur Anderson was a young man named Glenn Thomas. His uncle was David Thomas. David was a serial entrepreneur. David had this idea to do accounting software on the web.

Right, so this was late ninety nine. I was just I just didn't see a career at Arthur Anderson at that point. So I flew out to California to meet David. he kind of took me through what he was building, I got super excited about it, and I agreed to join as the first full time developer. How old were you at this point? I was twenty seven. Okay. Twenty seven? You're you're twenty twenty seven. You're twenty seven. Yeah, I was twenty seven. Yeah. Or twenty eight.

Twenty seven, twenty eight. Okay. Yeah. So I I I need to sort of dispel the myth that I'm some big risk taking entrepreneur. Like I was I was a young kid, sorry. I was a young kid, right, who just didn't like my corporate job. I I had tried to be an entrepreneur in the past and didn't have the guts to to take anybody's money to do it. When I met somebody who did have the guts, right, who had already lined up investors, you know, who offered me a salary to be a full time developer, I'm like, yeah, I'm in.

Right. And I moved my cal my family to to California and we got going on intact. It wasn't intact at the time. No, it was intact. yeah, yeah. It was in intact. for those of you who don't know, it was like born in the cloud from day one, the first line of code. Everything about it was was, you know, internet based, multi-tenant, cloud only. what what happened was we started the company, me just as a programmer, right

Before the dot-com crash. Right. So, and actually the day we took our first round of funding, the NASDAQ dropped something like 30%. So we were watching the NASDAQ crash while we were watching the wires come in from the investors. And you know, we managed to kind of get by still as kind of a hyped-up Silicon Valley startup for about 18 months.

But eventually we had to lay off most of the company. Those of us who were left took pay cuts. our our our our proper founders, David and and a guy named Odysseus, they left for for various reasons. And what happened was I was kind of the only I was the the string, if you will, to to that founding team. We kept things going, things started to actually work, took time.

We attracted new investors. and I was I was their sort of missing link, if you will, to to the the start of the company. And so that's how I sort of took on the mantle of of the founder. So I've always I've always felt more as a custodian of something. Still to this day. I st I do, yeah. I still feel I still feel kind of a custodial responsibility. obviously I you know I ran product and technology, so I built the product.

but it I I it was hard for me to accept this founder or co founder title because I I really wasn't. It's just they left early and I was the only thing left. And and the investors needed somebody that they could point to and say, Hey, here's the guy that was there at the beginning. You know, ballpark. I was number seven. Seventh. Yeah. I just wanted wanna ask. So

18 months you got up to a certain what was that employee count that then dropped down. You were eighty-five or ninety employees. Drop down to twenty-two. Well. That's a huge, huge impact for a business. And I'm I'm sure like how old were you at that point? I mean, I know you started twenty seven or twenty eight. I was thirty. And that that has to the confidence, like you you you you you have to be sitting there like at night going like, boy.

Like what what does the future look like? Yeah. Yeah, I mean if if you know the hype, there was you know, around dot coms at the time, you know, we we raised a lot of money on no product or revenue, right? we we launched the product three months after we closed our first round of funding, right? So we had no revenue, no product. But at the time there was so much belief and energy and excitement around the internet.

And applications built on the internet that as a 28-year-old, I figured I'd be doing this job for five years, make lots of money, and you know, go on and do something else. So on on the one hand, there is there is a real sense of you know your your hopes it's sort of dashed. but at the same time it forces a change in your mindset, right? This is this this n this has gone from something where, hey, we're gonna have some overnight success.

To something like, crap, right? We've got people who need to be paid. we actually have some customers now. Like this is a this is a real business that requires some real serious, a really serious mindset. So, you know, we we really hobbled along for a few years. around the time the Salesforce started to really take off, we attracted new investors, we we brought in some new executives, and that sort of started.

the the real growth of the business around 2007, 2008. Well, I mean I I I see I think I'm putting words in people's mouths, but I think that people see you on stage today and they just see this person that's that's there, that's done it, but don't know that there's been this whole path, whole challenge, whole like ups and downs and all arounds. And I think that's so important for people to understand, especially

people that thrive to be entrepreneurs or people that work for entrepreneurs, that's such a different mentality. And I'm I'm sure that even today you go home and have your moments of like, can I move forward, you know, in this? I'm I don't want to put words in your fa in your mouth, but Yeah, I it's cr it's different it's different moments of crisis, right? You know, the the crisis right now is the SAS pocalypse. you know, what what what is going to be the AI impact on companies

Like Sage, and we've had different, you know, different crises in the past. We we did go on a really nice long run of just steady, high pat you know high-paced, fast growth from around 2008. I mean, so that growth continues, just so we're clear. So getting kind of getting back to your question, we grew the business to about a hundred million in revenue. in 2017, we had a choice to either take the company public.

Or sell it to Sage, right, who was very eager to acquire us. I'd had lots of conversations with Sage over the years, who was a competitor to me. I didn't like any other leadership teams before that, no offense. the leadership team that How do feel about the current leadership team? Well he is part of that. So so so the leadership team in 2017 was completely different in their approach to the conversation. The arrogance was gone.

they showed real interest in the product. they there was sort of this this humble and curious mindset about what does it take to build and run a cloud business. And there was genuine interest in the technology, which which I hadn't seen before. And they were kind of open about you know how critical this was to the future of the company. And so, you know, we had already prepped for the IPO. You know, we had a we had a staff meeting one day where we had to decide, are we gonna file?

Or are we going going to accept this offer, right? the history is is written, we accepted the offer. and that for Sage was sort of the big down payment on Sage's transformation to becoming a a cloud company. You didn't want to lose software companies. Yeah, the portfolio was almost entirely off the And so this was their first cloud based acquisition? they'd done one prior, but it was much smaller.

Than intact. Yeah. Am I able to ask who was in that meeting to make that decision? yeah, it was it was Rob Reed, who was the CEO at the time. It was it was me, Harris Hajwanu, Mark Linden. It was it was, you know, the s Rob's equivalent of the ELT at Sage, right? So our head of sales and marketing. There's there was ten of us, or around ten of us that that you know, the senior leaders at intact that made the decision. Was it unanimous or

asking too much. Well no, it it it was it was not a terribly contentious debate. Okay. Because we we knew that going through the IPO process and then running a public company would be really challenging. And we also knew that to really scale intact as big as we wanted to scale it.

would be hard to do with without the the the resources of a company like Sage. Right. So a a lot of people know this. In tech's about 10x the size it was when when we sold the business. And there's no way that would have happened without without the Sage acquisition. We wouldn't be, you know, have we wouldn't have this flourishing business outside the US that we have now. We wouldn't have the the channel and the distribution that we have now

And and frankly, we were able to make some investments that as an independent company would have been hard for us to make. So, I mean, you know, the right decision all around. you know it it obviously has been huge for for Sage. Intact is like a third of the the revenue now and half the growth, right? So it's been huge for Sage. You know, what what I find interesting about this is like a lot of times, whether you consider yourself a custodian or not, founders

Don't

don't have the longevity into it. And you've you've navigated a path of being continue to be, a very integral part of what Sage is, not just what Sage Intact is, but what SAGES. Can you talk a little bit about sort of that path from 2017 to today? And just for everybody that's listening, 10X in under 10 years is extremely challenging to do for any company. So

when Steve Hare took the CEO job in 2019, he asked me to to to be the global CTO. so take on more than just the intact product, the whole portfolio. and I I was sort of energized by that opportunity, the way I was energized, you know, as a co-founder of of Intact, because we were driving a massive transformation for Sage. But

But for me, I suddenly had so many tools to work with. I had so many resources. I had so many markets that we could look at, so many products that that we had the opportunity to work with. So it was really, really energizing for me to take the CTO job. And we told the market at the time that we were gonna grow slower and we were going to start spending a lot more, right? So we were gonna take our margins down.

And we reinvested that into starting an AI team, really investing in in sort of core technology teams to build the Sage platform. So what year did you start investing in AI? So we formed the team in I think it was November or December 2018. Okay. And I was running that team within Intact. and and then

We we made it a global team in in April of two thousand nineteen. Eighteen? I c I'm losing track. Nineteen when I took the global CTO role. So And we've sorry, we put out our first real product about two years later. And that was the GL L GL GLR detection. No. So at my previous firm they were one of the a resellers of NTAC before it became Sage and they've told me stories where you came into the offices and you were selling

Intact and you got into some of the sales deals your clients. I still do. I I've heard that he's still. I know, I've heard that yeah, you still do. Do you enjoy that piece of it? I i yes, so very much. I I guess the first thing that I would say is I actually love hanging out with a sales team. to and and I've been doing this long enough that some of my closest friends, you know, in my life, like going to the personal, are Sage partners, right? because

When when you're when you're sort of at you know in the trenches with them, try to close a deal or trying to make a customer happy, you know, th those are bonding moments. so I I really enjoy it. and and I enjoy hanging out with salespeople. I've got mad respect for for salespeople, which unfortunately isn't true enough in the world of of engineering. but like somebody who

decides they're gonna take on the risk of selling your product as their livelihood, like that's commitment. and you've got to be willing to help them. So I've always I've I've always been pretty close to the sales team and to our and to our partners because yeah there there's there's sort of a genuine I wanna be out there with them element to it. It it makes it real.

Right. And and so all of those experiences make their way back into the roadmap, right? They they end up informing some of the creativity around what we can do with the product to solve problems differently. So there's a there's a real benefit to it beyond just my desire to hang out with salespeople. Well, I also hear that you're pretty close on the PS team. So we were lucky enough to have Greg Ecker on the podcast early on, if you're if you remember that. And

You hired Greg. I I was one of the interviewers, yes. You voted against it. Greg was great. So yeah, I I the the partnership there is they're implementing the product and Greg and I developed a relationship.

where he was unafraid to tell me what was wrong with the product. Right. you know, unafraid to give me the the the feedback on on what's needed with the product. And so, you know, when you can get you know implementers or or you know people on the front lines, you know, who are out there trying to make it work for customers and prospects, right? When you can get feedback from them, it's just, it's just gold. So I invested in that relationship as well.

It's harder now, right? We've got an army of of professional service and and I I unfortunately I can't build relationships with all of our partners the way that I'd like to. But as as much of my time as I can, I I do devote to that. So you you like kind of mixing up with the sales staff and you know, really understanding hearing feedback, all that fun stuff. Do you still find any time in what I imagine is just a horrible calendar of every single day for you to kind of get in the trenches and get involved in a sales process?

yeah, I mean we are as we speak trying to find some time today with a prospect that a sale a sales sales rep reached out and said, Hey, can you help? and the dirty little secret, and I I'm hoping you guys only have like five or ten listeners, because I'm gonna I'm gonna tell a dirty dirty little secret. It was thirteen. Okay, so the so to the thirteen listeners out there, the dirty little secret is once you get past I would say VP level.

In seniority, you gain more control over your calendar. And it would probably shock you how little email I get. Because if if they have to email me, there's something wrong. Right? So if the team can't handle it, if others can't handle it, right, it it it really shouldn't make it to me. and my calendar is under my control. So I can I can choose to prioritize these things and

But you know, the team that I that I have working with me, they they know that I want to prioritize being with customers and being with c partners, and it means a lot to me to help sales. I just wanna I just wanna take a moment to say that means that he actually agreed to do this. Somebody didn't force him to. This is absolutely true. Yeah. But you were vetted.

Whoa. Let's talk about that or off with that. So you Well they want they want me to be a scarce resource, right? Yeah, yeah. There's got to be some so something sort of untouchable and unreachable about me for it to actually have an impact when I when I do these podcasts. So yeah, there was some betting. You realize you just opened the floodgates though. Yeah, somehow they overlooked that.

We cut that. We can cut that part. With a thirteen. Hey, can you jump on the code? I I will tell you that I get a lot of requests to to do podcasts. I can imagine to do to do webinars. I you there was a stretch at the end of twenty four, where I did seventy five public appearances in three months.

Between speaking, between podcasts, between media. I think the Royal Family does less. Yeah. And but that's one of the best things I can do to help the company is is to be out there telling the story. So I I do try to say yes as much as I possibly can. Well I think I mean you do a I mean I've I've seen you speak now for years, and I think you do a a wonderful job of communicating what the vision, what the what the

the the North Star is for Sage, Sage Intact or Intact for that and and so forth. All right, Aaron. Couple quick ones. Because these let's just say these are user user submitted questions just for the sake of arguing here. Okay. Gotta gotta get some thoughts. Gotta get to know how that brain works so people can try to replicate you, even though there's only one Aaron Heroes. Are you more routine driven? Or you like kind of flexible, fly by seat? How do you make your decisions?

yeah, I'm definitely lie by the seat. yeah. I I have a couple of routines, but they're very minor. I I don't have a job or a life that lends itself to routine. I and I wish I had more routine, but no, I'm very much every day's different. go with the flow. Yeah. And do you kind of find yourself 'cause I know some people are, keep a keep a pen next to the bed.

Morning, afternoon, evening, middle of the night, when do you kinda or is it just totally random when your brain just starts firing and like, I can do that. Yeah, my brain works the best when I'm on a bicycle or I'm hiking. Doing something physical is is when a lot of things have come together in my head. I also get a lot out of brainstorming with with with colleagues.

When it comes to the the the speeches that I give, there it's it's very unfortunate and nobody should work this way. But things rattle around in my head until there's so much pressure that like

Aaron, you don't have anything and you've got to be on stage in a week. Right? You know, the pressure f sort of forces it all to come out. And then I I just like I vomit out all my ideas and and and they they they organize themselves. And so I do I do have I would say moments of intense productivity that unfortunately only arrive when there's pressure. Got it, which could be there's no like please don't be that way. Nobody should be that way. I wish I could change.

But unfortunately that's the way my my brain works. So how much pressure moments are there in a week for you? Not a lot, actually. Okay. there are pressure there are pressure moments in the year. Right? There's there's the big conference, there's analyst days, you know, there's more of those than there than there used to be. you know, there's important internal meetings where you know I need to to convince

a group of people, you know, in a direction that we need to go. So it's not it's not really a a weekly or a daily thing. It's it's you know, there's there's you know, ten or twelve events in a year where I need to really produce something very high quality that unfortunately doesn't happen until I feel enough pressure. Makes sense. It's terrible. It it's just I mean I wish I was different. Probably works w pretty well for you.

I mean, I think results speak for the process works. Yeah. You got it down, Pat? So Yeah, some days are busier than others, right? We've all been there. And after this big word vomit, you know, when that pressure point buildup, you get it all out and start organizing everything. How do you just kinda reset yourself after that? 'Cause it's I mean intense, you know, thoughts are just coming out like crazy, you're trying to figure out what to do with everything.

You know, moments of genius probably a lot of garbage thrown in there too. But moments of genius, how do you just kinda like, okay, I need to take a step back? What calms you down? How do you reset it? What calms me down? My favorite leisure activity for the last couple of years has been listening to vinyl. Really? And it's it's expanded a little bit. You know, I I started collecting CDs as well, believe it or not. Really? Yeah. I I

You know, I've I've got massive attention deficit disorder. And and there's something about deliberately sitting down and only listening to an album the way it was meant, you know, to be heard that is it's pretty calming to me. Favorite band? that's a tough question. I go through phases. So

I and I like a wide variety of music, right? So if you think classic rock, Led Zeppelin and Pink Floyd. but I also go into like trip hop, down tempo, so you know, Massive Attack, Everything But the Girl, Underworld's one of my favorite. I love punk, I love Joy Division. I love New Wave, from from from the eighties. lately I'm obsessed with Leon Bridges, who's just a brilliant musician who travels with a great band. I've been to a couple of his concerts.

it's it's it's really kind of a wide spectrum. If anybody wants to discover some world beats stuff, Gotan Project is great. Hermanos Kateris is great. It is a very, very wide selection, so it's hard to say what is your your favorite band, but I didn't expect that wide, but I forgot. I forgot. I'm a huge fan of of of sort of R and B influenced hip hop. So Kendrick Lamar, Anderson Packs, one of my favorites.

I will listen to Mac Miller all day long. Logic, who's less well known, I guess. but but that I I get into a mood where I where I want to listen to Patronalana. Shouldn't TI be on that list? sorry, Outcast is very much on that list. There you go. Okay. I I'm just trying to process like the wide spectrum that you just threw out there of different, you know, totally different type of s it's really interesting. What's crazy is when you see me coding with AI while I've got a record on the turntable.

Well that is a that that is a you know qu quite a quite a variety of of eras of I bet you have a lot of records. It probably takes up like a whole wall. it's not as much as you would think. I guess. Well, I mean I've only started collecting four years ago. So let's pick let's pick a moment in time. So let's let's say twenty years ago. What would the Aaron of today tell Aaron of twenty years ago?

yeah. So I I I think the first one would would be just, you know, be patient. i intact was a slow story to to evolve. it it took it took a lot of time to to build it into something that it is today. I I I like to to joke that overnight success doesn't last, right? you know and and I mean that, you know, for for companies as well as as as individuals.

you've you gotta work at it for a long time. I think the other thing that I would tell myself, I I'm I'm actually really proud of the way I've led teams, which has essentially been you all are great at what you do, and I trust you. Here's the direction we're going. Go do brilliant work. There have been times when I've

you know, had my own, you know, creative ideas that I've sort of pushed on the team. But there there were times when I felt strongly about a direction we need to go that I didn't push hard enough. And and you've you've gotta sometimes have conviction in in the things, you know, as a leader that you you know, that you you just really want to have happen. And and I think there were too many times

Over my my career, especially as I was leading the intact team, there were too many times when I I I felt really convicted about what we should do with something or how we should design something, what the architecture should be, that I didn't actually exert enough of an influence on the team. So on balance, I think it's i it's it's it's obvious it's been the right decision to allow the team to be sort of free, right? And and do what they want to do. But but there were a few times where I'm like, I should have I should have had more conviction.

I I think every good, great leader feels that way. I've I've seen it in different aspects in which you're going like, you wanna give people autonomy. You wanna make it theirs because when it's theirs, they own it more. But there's also your own conviction as you put it. And it's not it's it's that balance. As you say, it's like how how do I give them autonomy and push my own vision? And I think

You admin flowed to that. And so I think that's that's probably advice you give your current self, not just your Yeah, that is that I'm constantly telling myself, why why didn't you push that harder? You know it was the right you know it was the right answer. Why didn't you push it harder? part of it comes from, frankly, pushing things that were wrong. I mean this is this is one of the the big lessons is you know, with that conviction comes

things that don't work. So, you know, you've got to be willing to accept, you know, if you if you if you take on sort of leadership courage and act on your conviction, like risk and accountability lands with you. And if if you make this the way you work, there are going to be cases where where it's not, you know, it's not gonna work the way the way you thought it would. But but on balance, when I look back over my career, the things I had

a lot of conviction on wow this sounds really arrogant. I I don't I don't mean it that way. I really don't mean it that way. But you know, the big things and the architecture of intact, a lot of that just came from conviction. Right? It it in it it it came from a space where I was given a lot of freedom, right, to t to to make decisions on on how to build a product and to do it differently than the way it was done before. There were there were

More cases where I had conviction that I didn't push and I wish I had. I have to ask this. I I don't know this is part of our question or not. Give me a couple of your biggest failures. Well, we're to really bring down the big god I believe that failures drive success far more than success drives success. That's just a personal belief that I have. And what No, it's I I get it. It's good you know, for for those listening trying to build things, work their way up the ladder, do whatever they're doing, finding their own path.

It is important to know that it's not all just, you know, it's not all roses. It's there's some tough points. anything coming to mind that's kind of a I don't say use failure. Anything that was a learning moment for you. Well, so there are some that I'm not ready to write the book on yet because there's they're still they're still unfolding. I I think my biggest failures have to do with

So so I'm I'm gonna be generic and I I apologize for being generic. But but you know, there are times as a leader where you have to make difficult decisions, right? And in those difficult decisions, you know, people can be adversely affected. I've I've never regretted those difficult decisions. I've always waited too long to make those difficult decisions. And so that's I think that's that's that's one thing that I you know I still I think I'm I'm much better at now.

And it it does kind of come back to having conviction. But but making the difficult decisions sooner is is is absolutely a lesson to make. When it comes to the product, there's a bunch of things we tried that didn't work. And you know, you just have to be willing to learn from those and and move on. And and when I look back at the way you know, the way I managed the team building the product.

What's really interesting is is when you're in it, when you're doing it, you think you have less freedom than you do. Right? You know, everything feels like an imperative, right? You've got your teams allocated to do things. And, you know, when there's something that needs to be done that's different, when you're in it, it's it's it's hard to feel like you've got the ability to do that. In hindsight, there's no reason why I shouldn't have done.

Some of the things that, you know, if we had done them, right? Business needed them to be done. And I'm not talking about the things that were controversial, just things that needed to be done. I I think I had way more freedom than I felt that I had.

So I I think it may be a good way to kinda wrap this. You know, what's one kind of takeaway that you want people to remember about the let's call it w we're really sticking with the origin story of Aaron Harris? Like you want people that I want them to remember about me? Yes. Or one th jeez. Maybe maybe like just in general, like one thing to remember about your success, maybe like your failures about you? What's your like

It could be your f your favorite album right now, just something. So so there's there's a guy named Ray Dalio, who's you know a famous billionaire, who wrote a book called Principles that really guided the way he ran his businesses. one one of his principles was ride the wave you're on. And I I think I sort of on the poster child of riding the wave that I'm on, I've I've had the same job for twenty six years. twenty six yeah, twenty six years.

I I've been on the same wave for for for twenty-six years and it's worked out for me. And and trust me, there have been lots of opportunities to get off this wave and get onto another wave. But I've I've I've always decided that this is where I want to be, this is what I want to do. And I I know not everybody has that luxury. Like I know that I'm very privileged in the career that I've had and continue to have, by the way, I'm still young. but but

You know, I I think the one thing about my career is is you know, I found my wave and I rode that wave. And and if you have the opportunity to ride a wave that that is enduring, that that you know gives you fulfillment, there are there are shiny opportunities out there. but but for me, the best answer has always been to keep riding the wave I'm on.

It makes me think about the movie Point Break Point Break. The red hot chili peppers were in that movie, so I I'm thinking about his music. I do have red hot chili peppers in my collection. there we go. So do you know the movie Point Break? I do. I don't I mean I it was a long time ago. they remade it recently, though. I've I've didn't see the remake and I can't remember the original. I know it's about surfers who get into some crime. Yeah, yeah, yeah.

But I don't know why like why riding the wave and the music thing kinda brought that movie to the forefront of my brain, but yeah. So we always end these things with a terrible dad joke. All right? I always I always sort out to the to the guest if you got one on Standboy, I'd love to hear it. If not It's really simple. Okay, let's hear it. We normally don't get them right, so skeleton walks into a bar and says to the bartender, I'll have a beer and a mop.

there wasn't even a hand. That's a good one. That's good. that was the moment so I I told that joke to ChatGPT about f I don't know, like right after it came out. And it f it read back to me why that joke was funny. And that was the moment that I knew the world had changed. I actually remembered your your speech, right? Yeah, I think you talked about that. Yeah, I did. Yeah.

I I I thought you said that put it in the chat GPT and it somehow you just showed me a picture of eyes rolling back. And then you had of course had to go and tell the joke to your kids. But thanks for joining us today. It's it's been fun, Aaron. Throw the titles aside, and all the all the career accomplishments, all this fun stuff. What would you say is your most proud moment in your life? Well I I I think

Very that's a very personal question that I didn't prepare for. But what I immediately go to is I'm proud that I have good kids. And and and I don't mean successful, you're right. I don't mean f you know, lots of accolades. Obviously they're they're they have degrees of success, right? They they do have their accolades, but they're they're good. Like they're genuinely good people. They're good people. Yeah.

and I I'm really, really proud of my kids for just being good people. and it's genuine, right? They they are just genuinely good people. I I I often laugh when people tell me or ask me how my kids are doing, and and my standard funny response is, Well, there's no wanted unwanted pregnancies and and nobody's in jail. and but in fact the opposite is true, right? They're they're just they're good people.

And I'm really proud of that. And they they they've got a a view of life that's different than mine in a good way, where they they they really look at what they want to get out of life, I think in a really balanced way that I admire. I think that's amazing.

Doug is expecting a a a new born in July. that's his second. I have Congratulations. Yeah, yeah. I'm already tired. I have an eight and a six and and I think that's like what all of us as parents want is, you know, it's not about what they do professionally, it's about who they are, what are their principles. and I think that's I I think that's amazing. So Yeah. I I hope to be able to say the same thing.

When my kids are older. And then when he finally does something where people want to interview him.