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Bryan Healey - The Entrepreneurial Journey of a Startup Founder

Season 4, Episode 6 | November 9, 2021

In today's episode, Dan and Bekah talk to Bryan Healey about how to kickoff your career as a start-up founder and the lessons he's learned along the way.


Bryan Healey's profile photo
Bryan Healey

Bryan Healey is an entrepreneur, tech leader, data scientist / ML engineer, and biz developer. He's helped create or grow several start-ups, raised money, and built/managed teams of varying sizes, small to large. Currently co-founder and CTO at Aiera.

This week Bekah and Dan sat down with Bryan Healey, an entrepreneur, tech leader, data scientist / ML engineer, and biz developer. Bryan talks about gaining experience as an entrepreneur, how to get started in the start-up life, and how the entrepreneurial spirit has always been in his blood.


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Transcript:

Bekah:

Hello, and welcome to season four, episode six of the Virtual Coffee Podcast. I'm Bekah. And this is a podcast that features members of the Virtual Coffee community. Virtual Coffee is an intimate group of developers at all stages of their coding journey. And they're here on this podcast, sharing their stories and what they've learned. And we are here to share it with you here with me. Today is my cohost Dan.

Dan:

Thanks Bekah! Today, we talked with Bryan Healey. Along with being one of the original members of Virtual Coffee, Bryan is an entrepreneur, tech leader, data scientist, machine learning engineer, and business developer. He's helped create or grow several startups, raised money and built managed teams of varying sizes, small to large. And he's currently CTO of a FinTech company. He co-founded called Aiera. Bryan has had a long and interesting career, and he's been in a lot of different roles. He's being hired as an engineer, hiring and managing others and founding entirely new companies. His experiences have given him a unique approach to decision-making that he was kind enough to sit down and share with us

Bekah:

We start every episode of the podcast. Like we start every Virtual Coffee. We introduce ourselves with our name, where we're from, what we do and a random check-in question. We hope you enjoy this episode. Today's random check-in question is if it were possible, would you live on the moon? I'm Bekah, I'm a front end developer from a small town in Ohio, and not live on the moon. I feel like there are plenty of spaces in the Earth that we have not explored yet. And so I would like to start there.

Dan:

Um, like what.

Bekah:

The deep sea.

Dan:

Bottom of the ocean. Okay.

Bekah:

Where the aliens live.

Dan:

Uh, hi, I'm Dan. I live in Cleveland. I do development of many kinds, I suppose. And, uh, yeah, I don't like the moon as it exists right now seems pretty, you know, boring and empty and all that stuff. Right. But I've read like a number of different books that are set sort of in the future where the moon is... you know, populated to different levels or whatever, you know? So I would consider it in, in those cases, it depends on, you know, like what they got going on there, you know, do they have like movie, if they have like movie theaters and, you know, uh, restaurants and stuff, you know, if it's like that kind of thing, uh, then yeah. But if it's just like all just like tents and science people, and then it's less interesting to me, to you, you know, but I do like exploring like, you know, new areas and hiking and stuff, so that, that could be cool. Plus the jumping always looks always looks fun. Yeah.

Bekah:

vertical would increase. I really think so.

Dan:

I would hope

Bryan:

Quite

Dan:

Yeah.

Bryan:

Yeah. Go, uh, I'm Bryan Healey. I'm a entrepreneur in Boston, mass. Um, and I currently am a co-founder and CTO at a company called Aiera. And per the moon, I'm going to go with probably no. Um, I'm in the same camp as Dan, like, if, if, if it's built out, like we're talking future moon with like colonies and like tons of stuff then okay, maybe, but even then I feel like I have my option, I prefer like Mars over the moon.

Bekah:

Mars. Okay.

Bryan:

yeah,

Bekah:

So maybe the question should have been like outer space. somewhere

Bryan:

Absolutely. Yeah,

Bekah:

cowboy.

Bryan:

we're going somewhere

Dan:

Why? Why is the Mar why is Mars better than the moon?

Bryan:

Uh, just slightly more stuff. Like it's like probably had water at one point. They'll be more to investigate. It's got a little

Dan:

Uh,

Bryan:

uh, you know, it's got mountains and glaciers and, you know, whereas the moments like once you've seen 100 square feet you're just looking at different types of rocks.

Dan:

Just different craters. Yeah, that makes sense. That makes sense.

Bekah:

Yeah. Um, welcome Bryan. We're really, really excited to have you on the podcast today. For those of you who don't know Bryan, he is one of the first people to ever come to Virtual Coffee. And so has been around a really long time because of Bryan, we have a slack. Um, so you, you all owe that to Bryan. Um, this is long overdue. I feel like. So thanks for being here.

Bryan:

yeah, happy to..

Bekah:

so we always start off with kind of your origin story, your background, and a little bit about what got you to this place where you are today.

Bryan:

Just generally like my career? Um, you know, I probably had one of the more straightforward career paths in tech. You know, I, I went to college for computer science right out of high school. I went to Northeastern University, uh, here in Boston. Um, studied Computer Science and jumped right into, you know, working at a startup while I was there. I actually, so the, the actual path of my career, uh, was I. Northeastern has this sort of five-year program where you, you actually do work interspersed with academics. So you six months in school, six months on an actual, like, uh, like industry job.

Dan:

That's cool.

Bryan:

Yeah. it was pretty cool. I didn't even realize how cool it was at the time. I thought it was just like, ah, money, you know, as, as, as a older adult, I'm like, damn, that was a, a big leg up in terms of like how the future progressed. Um, but so I did a, I did two, like more traditional internships. Six-month internships. Um, Goldman Sachs and WR Grace. So fairly large large-ish companies. Um, then, uh, in the intervening period before my third one, I actually started a small, uh, startup, uh, in my dorm. Um, ironically, it was of a silly thing. It was a notetaking shareable notetaking social network for like other college students. I was trying to actually pitch it Facebook style to like the university would sponsor it and to cover fees and everyone's sort of joined in, uh, it did okay. It was sort of making a little money, um, but ultimately I actually kind of got Acqui-hired into my, uh, uh, second role, which is working at another startup in Boston called Garment Valet, which was sort of the, luxury delivery, uh, laundry service. Uh, and so they had this pitch where they were trying to create like a national brand out of it, and they were going to create like a central tech hub that sorta managed, uh, almost like Uber style, like drivers across the country would, would work for different shops. And it would sort of. You know, work somewhat independently, but centrally managed. Uh, and so I joined them as my third before graduation. and they ended up staying there. So I was there for like three and a half years building out their platform scales from like three people to 25 people. Um, Yeah. And so, I mean, can obviously keep going for forever. I don't know how far you want me to take my

Bekah:

Well, I just like want to pause for a second. Cause you're like, oh, I have a traditional path into where I am today. And you were like, I started this startup in my dorm room and then I worked at another startup that was acquired. And I'm not sure that that's the traditional path. And I think that's the very Bryan Healey path of doing all of these things and just like, all right, going to keep going with it.

Bryan:

Fair fair. Yeah. Maybe traditional is the wrong word. I should've said more like I didn't career transition.

Bekah:

Yeah,

Bryan:

I was just like straight into tech, like ran out of the

Dan:

did.

Bryan:

Yeah, it definitely, probably not truly traditional from like what most people experience, which is just like, get a degree, get the first job and sort of March from there.

Bekah:

Well, and so you've always been involved in the startup life then. So it's been startup after startup. And then, so at some point you transitioned from somebody else's startup to your own startup. So where's that happening.

Bryan:

Yeah. I mean, I I'll quickly caveat that by saying that I didn't realize this was potentially unusual until I was older, but I've always had that bug in me. I think I was starting businesses when I was eight years old. Like I was always been doing thing.

Bekah:

Eight year Bryan's business. Thats what I want to know.

Bryan:

Yeah. So, well, like for instance, like random, uh, story in that vein, but I'll only tell one of them. So when I was. 10 years old, I started a lawn care service in the neighborhood, but I hired all of the neighborhood kids to work for me.

Dan:

amazing.

Bryan:

and essentially got about 30 houses in the neighborhood. Just sort of sign up for this like kids lawn service. And, uh, and I would take cuts at everybody doing care for

Dan:

That's awesome. What, what, like, where did you learn to do that? Or think that way, you know, that early.

Bryan:

the weird thing. I just sort of like. I mean, I, I, I must've learned from somewhere, I guess, but I don't have a clear vision in my head of where, I mean, I'd probably just observed

Dan:

Um,

Bekah:

Twain.

Bryan:

yeah, yeah. Just think observed other people doing things and you're like, I could do that. Um, so yeah, that's my random aside. So. So the progression from how I got to college to my own startup. Um, I, I won't tell the whole story cause I I've had a lot of gigs in my career, I think not eight, eight gigs in total. Um, but the gist of it is that I've I've sort of to the startup space in general, at the very least sort of like innovation space. I I've had a couple of tiny stints at bigger companies, but usually it was in a very specific capacity. So like I did a stint at Amazon in 2013 to 2016. Um, uh, but I joined specifically to work on the, uh, Echo Alexa project. Cause it was like an, it was a brand new division in the business. I was one of the first 50 hires. I got to sort of like play entrepreneur inside of a big beast. Uh, and that was its own kind of fun other than like random deviations like that. I've mostly been around startups, either help try to find them or just join very early. like from, from the startup, I joined in college art LA um, I jumped to another startup as the hire, called shape up, um, and was there from six people to, I think about 75 people, something like that. Um, jumped from there to another startup, uh, Uh, sort of a later stage startup, I think I was like the 52nd higher, but it was another like, um, that vein, they were like four years old. Um, whose name actually escapes me now. They were up in Waltham. Um, and then from there, I, actually tried to start a startup of my own, a company called JoinVester essentially early days of like crowdfunding. I was trying to start up sort of like a republic.co style company, trying to get people to sell their startup shares on an exchange using, um, very new regulation called, oh no. What was it called? oh, that's going to bug me is actually a name for it. It's kind of a cool name, but it's just been so long. It's like out of my head now. Yeah, I ended up bringing on two co-founders while I was doing that, we a little bit of seed money and we sort of were talking to investors and sort of try and get things going. We never quite got it up to like launch. There was all kinds of questions around the regulation. Is this going to last there's a lot of opposition to it. Is it worth investing in companies to sign up was a challenge. Anyone who is a really high value would of course just go range, venture raise venture dollars. And so it was like getting quality deals. Do you have the platform was that was a bit of a stretch. So that for about two years, but never really took off. Um, and it was from there that I, uh, Jumped to another startup called name May Media in other ones that like late stage startup, I think I was like the 60th employee they were like four years old. It was like pre IPO. and I was there through them getting acquired. And then from there I jumped to Amazon. And so that's sort of where the next piece of it sort of takes off. So while I was at Amazon, I ended up getting recruited into being the AI director at a company called Lola. Which is, uh, if you know anything about kayak.com was founded by this guy, Paul English, um, he's a big name in Boston. I'm not sure how, how far his sort of like presence reaches in the wider US tech community, but he's a big deal here. um, so he co-founded Kayak after he sold Kayak to Priceline. He started Lola as I, this new venture conversational, um, base. So like, it's sort of like an automated travel agent was the original pitch. So you can. I have the experience of personalized travel agency without having to physically go anywhere, even talk to a real human, you could just do it through, this digital experience. Um, and so I joined there through that whole experience. I got connected with my current co-founder Ken Sena. He was, uh, a senior at a company called Evercore. Uh, and then later Wells Fargo. As an analyst, which basically he's sort of a financial pro. He, he, um, advises big funds and firms on how to invest in money. Um, and through connecting with him, uh, we ended up co-founding Aiera, which was sort of like this, um, AI enabled platform to help analysts do their job better. Make smarter decisions. days of Aiera, it was actually literally making predictions, trying to sort of like do the analyst job of writing research and sort of making recommendations. and it has evolved more into like, um, a pro's, uh, Suite of services to help them do the job on the edges better. We, including the big centerpiece of ours is events. So we connect to calls, conferences, things that investors care about and pay attention to and make decisions on. And we them and analyze them and make it easier for investors sort of like handle that workflow.

Bekah:

Yeah, that's awesome. So all of this experience, it sounds like you've got to play a lot of different roles, which seems really. Fun. I'd love to know maybe like your best experience was or, or what made you, what were you most excited about doing throughout this period?

Bryan:

really hard to pick a favorite experience. Cause it's, it's more like there's been a suite of things that have all just been different in different ways. And I have highlights from all of them. So I get sort of give some of those top line highlights. I mean, like for instance, uh, joining Shape Up, was, was a specific experience. So prior to Shapeup I had been in this other startup, but that other, it was more of a grind, you know, like I joined as the third employee, it took three and a half years to get up to 27 employees. And then the, you know, 2008 recession the business. and so it was just like slow grinding process of like building a business a much more like ground level, like functional business. They actually had like trucks and drivers and felt more like real world, if that makes sense. To join ShapeUp was the, my first experience on like a rocket ship. Like I joined a company that sold digital products. So there was, it was just an office and servers. I joined as the third employee and in a year we hired 50 people and then was just like this curve. And while I was there, we raised a ton of money. Um, and we hired a new CEO, a new CTO, and like, it was just. It was a firehose of crazy every single day for the whole time I was there. Um, and even after I left, I got to watch them. I stayed in touch with people and they just kept rocketing. And eventually they got acquired for big dollars by Virgin Group. So that experience, think colored a lot of the rest of my career of like, oh, this is what I like. This is fun. I enjoy the intensity of it. know, even things that might not even seem fun in the moment. Like we had a couple of stretches where we had product launches with deadlines and I'm literally sleeping at the office for 24 hours a day for like four or five days in a row. And it's like at the, in the moment I might've hated that. in hindsight, it's like, that's an experience that like is hard to reproduce in a successful way. Um, and so sort of colored my realization that. Me being around startups. Wasn't just a convenience. This is where I like to thrive this, you know, I've done the biggest, bigger company thing and internships, and like, this is the fun. Um, and then, oh, go ahead.

Bekah:

I was just gonna say, it seems like so many different personality types. There's there's a fit for that. Right? So there are people that would thrive in that startup atmosphere. There are people that will thrive something that's more like a nine to five, and this is the same things that we do pretty much every day. So it's really dependent on like who you are as a person.

Bryan:

Yeah, exactly. Right. And, and if I, if it's possible, my advice to younger engineers is almost always to do a stint at each

Bekah:

Um,

Bryan:

sort of get that experience level. people just know themselves well enough, and that is that's Okay. you truly are like, now I know I would hate that nine to five, like clock-in, clock-out do my job kind of thing or vice versa that that's good to know that, but if you have any sort of questioning tech is, is somewhat unique in the world of work. And that is very common and not at all judged to do like year or two years stints. So you can sort of do some stuff first and sort of build up a bit of a resume and build up a bit of an experience cash and be like, okay, I, now I kind of know what I like and saying, then you Target. Yeah.

Bekah:

thought about that. That idea that it's normal to move from place place after

Bryan:

Yeah, especially. Yeah. You know, once you get to really senior level, just start rising to like director VP C-suite stuff. Now it becomes more like, well, we expect you to be stable. You're here as a leader, but when you're in the junior C made an even early senior levels, it's sort of like, you're just a gun for hire in most of these places. So it's not judged during usual if you're sort of jumping around. Um, you know, I think the only mark I ever see is sometimes people like I'd like to see at least a year, you know,

Bekah:

Yeah.

Bryan:

so they can at least stick around for a couple of projects and, you know, see some things through to production before they move on.

Bekah:

Yeah, absolutely. So, okay. So kind of like along those lines, do you ever hit that burnout point though? Like, I feel like there's gotta be a point. It may be, it's not hour spent, but the just not there. And you're like, why am I doing this anymore? Or have you just always found that like, okay, I've got momentum, that's carrying me forward. And I'm excited about this.

Bryan:

Yeah. don't know if this is unusual, my suspicion as it is, but for some reason I do have like bottomless energy and always have, so I've never really experienced burnout in the classic way. People describe burnout. I will say I've experienced things, similar burnout, and it's almost always oriented around how excited I am when things are going on. know, we've talked about this in other forums. I'm a, I'm a ADHD even diagnosed as a child. And so I have that sort of like dopamine fixation of like, I need something to me in. If you can latch that, then I'll go 24, 7, 365 at full speed all the time. And I, and I can just. Sustain that energy. Uh, as soon as I start to lose that though, I start to lose the ability to sort of maintain that just because. Connection problem, my brain. And so most times when I've experienced it, it usually just means I'm ready to move on. Like the company I'm at is no longer at a place where it's really engaging me. And I'm sort of starting to work on side projects more than I'm working on my main project. And, um, and, uh, and I'm ready for the next big challenge. So it's, it hasn't happened to me much in my career with a few times it's happened. That's been the result. It's like, okay, it's time for a next big thing that's going to excite me.

Dan:

When you're, you know, um, I have similar, you know, like a, a similar situation going on. Yeah. Um, but the, my question was, um, you know, knowing that about yourself, did that enter in the, your decision making process about starting a company now? So now you're like, you know, a co-founder of a company and maybe it feels like you might be a little less like able to. Hop out, uh, you know, you know what I mean? And I was wondering if I was wondering if that entered in when you're thinking about it. And also like, now that you're, how long has, how long, I'm sorry, how long has, uh,

Bryan:

uh,

Dan:

and

Bryan:

at Aiera uh, we're about three half years

Dan:

three interviews? Yeah. So like two parts of that question, I guess, you know, before, when you're thinking about it. And then now, you know, now does that thought ever like creep up or, you know, like how would you like approach that in this situation? Cause you're not any more a gun for hire or whatever.

Bryan:

yeah, for sure. It definitely changes that capacity too, if I ever did feel so to like the urge to like move on, it would be considerably harder, but th there's sort of a caveat to that is which is, this is my thing. And so like, I can kind of the direction, um, and you know, It's, it allows me to be more flexible than I'd be able to be in more traditional roles. And so there are still of course, boundaries self-imposed boundaries for like what the business is. We can't pivot all the time and we have investors and you have to make good smart decisions about how to run the business. Um, but you know, My ability to contribute to the business has been able to be as flexible as necessary, both for my own ability to contribute and my ability to sort of empower the team to, to what they need to do. And so, know, my role has shifted over time from being like. Primary full-time ML engineer working on a prediction product being mostly a sales tool and business developer to moving back into like where the R and D style role working on, uh, NL projects that are on the, on the front burner of demand, but are important for like long-term value generation. And so being able to sort of like set my own vision and sort of work with the team, opposed to like, here's your project, you're working on X and. As well as sort of influenced, I think that balance a little bit, all that being said is worth caveating. That, and this is somewhat funny to admit, almost all of my career from college to now has had a remarkably small amount of planning. It's mostly just been like, Hey, that's exciting. Hey, that's interesting. And just sort of like moving w where

Bekah:

We're all method, right?

Bryan:

exactly.

Dan:

That also sounds very familiar to me.

Bekah:

Yeah.

Bryan:

For sure. And so I, I confess to say that I think very little of that was pre thought like, oh, I should be careful here. This is a start up. You know, it was just more like

Dan:

Totally.

Bryan:

this now. This is exciting.

Dan:

Yeah. no, I there's a lot in like, you know, I I've, I don't, it start-ups, but I've been just independent, you know, my, my whole career as well, you know, and I think that I find that a lot of people, um, especially people with ADHD that are been in the industry for a long time, I, I think are gravitate towards these sort of situations where there's yeah, in control a little bit more of their own, uh, their own destiny, you know?

Bryan:

Yeah, A little more, you just a little bit more in control of how you can direct your injury.

Dan:

absolutely. I think that's right. It's really important cool.

Bekah:

Oh, sorry. I, So did you decide, like you were ready to start your own thing or was that, I mean, I imagine that can't be really impulsive, right? There's gotta be some thought process. You on a co-founder.

Dan:

Yeah.

Bryan:

well, th a there's, there's genuinely kind of two answers to that actually. Um, the process by how moved into and out of startups of my own creation, I've, I've, I've attempted or successfully created my own startup, like four times. Um, uh, I'd say two of those were genuine successes of some capacity. Every one of them kind of evolve the same way, including Aiera which is that I've never really been anywhere. That wasn't my company where I wasn't working on lots of side projects. I just, I'm the type that can't really sit still. So when I'm, when I'm done the work for the day and I'm home and I'm working on something else and scaling effect is when is sort of in my mind, when am I spending. When am I almost doing two jobs? Like when does it move from like a 10 hour a week? Like having fun side project to like, this is a thing, and it's really showing traction and there's excitement around it. You know, um, building Aiera um, there was a good six month period where I was still in my other job. but Aiera was consuming a lot of time. Like I was doing like sales runs and going to New York and pitching. And like, it was, it was a meaningful thing that I had built entirely on the side. Uh, and so there is, there is a decision point where you're like, I could probably just do this now. Um, but that does genuinely just kind of appear like the, for me, it's always been just like, there's literally a day where I'm like, I should just be doing this. This is really what I'm enjoying doing the rest of the thing, you just paying bills and adding stuff to the bottom, bottom line. And so it's time to shift with the process of getting there is very organic for me, at least like I've just always got another thing going that I'm excited about and want to see if it goes somewhere. And most of them, peter out, most of them don't go anywhere, but you just keep trying stuff and number I've probablty started projects of some kind that I thought might go somewhere 20 twenty-five times. And most of them don't know where they just, they just sort of languish. And then I closed them down after awhile, but

Dan:

Um, do you have any. About, like how to, how to consider those projects that, uh, you know, that don't go anywhere. I I've, I've heard and also experienced, you know, some like people expressing, you know, shame or whatever about, you know, some side project they wouldn't know, or, you know, it's, it's still there and it's, you know, like that sort of thing, you know, like, and, and you seem, I'm asking because you seem like very comfortable and, and, you know, feel good about it, about the situation. You know what I mean? I was like, wondering how you approach that, like, uh, like the. Um, you know, I think people sometimes avoid starting side projects because they don't want to make something that is going to fail or, you know, for instance,

Bryan:

I mean, The, the, the unfortunate answer is some of it. I don't know how to, to answer other than just like, don't be shameful. I know that it's a terrible thing to say. It's like telling somebody don't be sad, you know, but like, this is an element of that where I've just never really felt a problem with that. I liked to do stuff. And when things don't work out, I'm very failure comfortable, I guess is the way I describe it. Like

Dan:

Yeah.

Bryan:

things don't, I, in fact, I almost have this, um, it might be almost a negative. I haven't quite decided, uh, in my own self analysis, but like when things don't work out, I'm really comfortable going like, okay. And then never think about it it's like, I can just completely move on once. I've decided that something's not going to work and like right up until that point, I will be doing like 110% to try to make something work. And it's like this weird thing I can do where I'm just like, okay, I've decided it won't work. And I move on,

Dan:

that.

Bryan:

in terms of like, but other than that potentially. Uh, advice, uh, the, the more practical advice that. we give is really just around like perception thing. Um, the only reason I could imagine to feel a problem with it is you're fearful of like outside perception. Like, does it look like I'm a failure? I guess it could be internal

Dan:

Oh yeah, that's

Bryan:

but I, now I'm kind of projecting a

Bekah:

me out on that. Bryan. I feel like personally attacked right now. No, I don't feel like that. it.

Bryan:

So it's like, so if it's an external validation concern, uh, and I dunno if this is helpful or not, but in general, I would say nobody's going to judge you for that a hundred percent. And anyone, anyone who might is somebody who's weirdly thinking about things in a way I can't wrap my head around, I don't monitor, people's GitHub accounts. They're like, oh, they deleted Something's weird going on there. Like nobody cares. This is not a thing. So like, you

Bekah:

Yeah.

Bryan:

from, from a hire, from like an employer perspective, I like seeing people that are tinkering and toying and creative, like ultimately we're in a field that is a very mental, creative field. I want to see people who are sort of like. Out there willing to take chances willing to experiment. You know, it's a fundamental basis of experimentation is lots of your experiments, prove your hypothesis wrong. Like that's what you're looking for. They all just proved them. Right. Then they wouldn't, you know, something's not right there. So

Bekah:

I love that. And I want to

Dan:

Yeah.

Bekah:

a minute just to make sure that we emphasize that. So, you know, that idea of loss projects can be where you can testify. Like, look, I am trying new things. I am getting creative. I want to push myself beyond these things. And I know when it's time to stop and move on to the next thing. And that's a great way to reframe those experiences.

Bryan:

it's also worth saying that like, there's also nothing wrong with, with having ideas. That linger, like if you're working on something, but it doesn't yet have sort of like a clear niche and you're not taking off, but you're not ready to call it. That's fine too. Can just exist out there. I've done a small handful of those. I got, I'll give you a silly one. out there anymore, but I, uh, years and years and years ago back in 2007, eight God, long time ago at this point. Back in my PhD days, I wrote a framework and PHP called helium. Uh, you know, mean, I'm egotistical uh, it was, it was just the standard MVC style framework, but I spent a ton of time, like just sort of like pouring in there. Um, I had no idea what it was for. I just like did it to do it. Um, and so I put a website up with it, through up a GitHub and I was, uh, I might not have been GitHub back then. It was SourceForge SourceForge and, uh, And it was just sort of like, Okay. here's, here's the thing I built. Maybe it'll be something interesting. Um, back then there were companies that were sort of cropping up that was just selling like frameworks as back in the very early Django days. Um, you know, the early, um, oh, what was that PHP site anyway? Um, but I didn't know what I was gonna do with it. So like for, for a solid like five, six years, it was just a thing that existed that update a year when I got the motivation and then finally. I think I'm the only one that's ever used this. This it's just my thing basically. And I just didn't feel like maintaining it as I took it down. And that that's fine. It's just a, it was a toy that I was wanting to see if it went somewhere. It didn't and that's okay.

Bekah:

Yeah, I really love that. I think so this, this is going to be a little bit of a tangent, but, um, there was, uh, when I was first starting learning how to code, I went to this, um, conference online and one of the talks was about how to monetize your kids hobbeys. And I was like super kind of grossed out by that. Like, Hey, why don't we just let kids have fun? But then as we move into adulthood, like that mentality, I think that that exemplifies what the mentality of adulthood is, right? Like if you have a hobby, you better be making money off of it. Right. And like, why not just try some things out and see what happens with it, or have fun with it and not put all this pressure on yourself to be founder or to build the new and best thing. Like you don't have do that thing in all of your projects. Like sometimes it's just worth pursuing to see like what comes out of it,

Bryan:

It's sort of, it's sort of weird, like, In my experience, this is just anecdotal, but in my experience, the vast majority of successful founders, really aren't people that set out to be founders. They're just people that do stuff. It just like a do stuff. Just constantly doing stuff.

Bekah:

The ADHD people. people

Bryan:

all the ADHD people. And it's just like, I just need, I need, I need something in front of my face. That's taking up my, you know, my attention and, uh, and they just end up, like I said, they fall into something lucrative, like. This is a thing. We have a lot of users. Now, this is, this is cool. And you can sort of lean into it and sort, it takes off. Um, and that's Okay. Like, it's, I agree with you. Like, it doesn't have to be like, oh, how can I make money?

Bekah:

Okay.

Bryan:

I, you know, like, how can I make money right now? What can I do to convert this? I mean, obviously money's important part of life and your job and all that,

Bekah:

Yeah.

Bryan:

you're, you're focusing really just being more on doing things and, and I think it can be... even that's a little bit, want to make sure I'm not being disingenuous. Cause like I'm always wanting to found a company. I'm an entrepreneur mindset. It's more just like, how do those two mix together? My mindset is that, yes. I like being entrepreneurial and I wanna, I wanna take things somewhere, but it's like, I'm not going to a legal pad and going like, okay, my next business idea. You know, it's just, more like in the back of my head, I know that's where I might take everything eventually. Like that's what I'm tinkering. But in the moment I'm just tinkering and then we'll see what lands

Bekah:

I've talked to a number of people who are in like the more senior portion of their career in the past couple of months have just felt. You know, they've hit what we often refer to as burnout. And I've, I've said like, you know, I think your bored, like this was interesting when you got started and I see it all the time. Like it is interesting and you push forward and you do these new things. And then at some point. You stopped doing all of the new things, right. It gets a little bit slower and you're working on the same things. then it just, it becomes hard like in, in honestly, like it's, it's a place where a lot of people experienced mental health issues where they start to become depressed because they don't have that same like or like that momentum for that keeps them going. And then it just kind of like. Oh, that thing that you've invested so much time in, that's given you energy. It's not like sucking all of that energy out and like, Hey, it's time to move on. Like, whether you don't have to find the perfect project, but find something that's better than what you're doing.

Bryan:

Totally. Yeah. And, and you can, you know, I always feel like a little bit, I, I'm not calling anyone specifically, but I hear a lot of things when I, when I go to younger engineer forums and discussion points of like, there's a lot of focus on. Trying to plan your career. That makes sense. It's like, what's the next thing I should do. I'm looking at all this options, you know, and if that's your personality type, that's great. I'm not gonna discourage anyone to do what works for them. But in general, I'd say that there's nothing wrong too, with quite literally being just like a rock in a pond, like. If you see something cool, go for it. Like this. There's really no like, oh, is this a bad career decision? I don't know, do it anyway. know, if you're, if you're working at a company it's not, not making you thrilled and you hear what a startup that just doing something that intrigued you. Pursue it, maybe it doesn't go anywhere. Maybe you don't get the job. Maybe you get an offer. It's not good enough, but always be willing to take chances and just yourself out there and dive into things. I think that's the only way to, like you said, avoid that burnout where you don't feel like you're stuck to a thing. You can always move anytime you need to.

Bekah:

Do you ever find that? I mean, maybe personally, and as a person that like hires people for the company that you have someone on the team, or you've been in a situation where it's very exciting initially, then very quickly they hit that like, oh actually, maybe this is not for me. and then what, what do you do in that situation? Or, or what advice would you give.

Bryan:

um, well, so there's probably, there's probably two answers to that, what advice would I give as the employer trying to retain my talent? I would, I would probably encourage them to pick up new projects internally that they might find more exciting. You know, what things can, can we put them on that gets if the motor moving. From a mentor perspective, not outside there. I'd say that there's nothing wrong with making that realization quick and starting to look right away. done that before. I've had, I have at least one, maybe two. I'm trying to really think through my career now, but I know I had at least one like six months didn't I'm like resume where I was like nah this isn't, I'm not enjoying this at all it's time to move. And I just really looked around and there's nothing wrong with that. I think if you did that repeatedly, like four or five, six times in a row after a while, it starts to look funny, but one or two or even three in a career happens it's normal.

Bekah:

Yeah. I mean, that's such good advice. Like, oh, we find so many people in that position all of the time trying to figure out what they're doing. And it's a lot of, it's the hang up on what it's gonna look like a resume.

Bryan:

Yeah. And, and, and like, anything else I'd say that it's sort of, it's sort of shitty to make this kind of advice, but like, there does come a point where things like that get weird. Like, like I said, if it was six of

Bekah:

Yeah.

Bryan:

as an, employer I might go, oh, they haven't a one, one year stint in the last, you know, six jobs. That's a little weird, but like there's no magic number where it's like, oh, four is too much. Like, it's, it's really just. It's really just an eyeball test of like, how does it look? And in general, I'd say a few of those is not a problem that they were bothered me as an employer. If I see like one or two of those, um, I might ask a question in the interview, just be like, Hey, I noticed, you know, you had a, you know, six months didn't, you know, what happened there all I'm ever looking for is just like, Yeah. it just wasn't, you know, it wasn't the right fit. The projects weren't as exciting as I thought. And we parted ways, amicably that kind of stuff. Yeah. It was like, as long as they don't get the, oh yeah, I hated my boss kind of answer then.

Bekah:

What if they do hate their boss, what does they have? A terrible boss.

Bryan:

Well, has nothing to do what we've been talking about,

Bekah:

Okay.

Bryan:

like random career advice. Never say that even if it's true, cause nobody cares and all, it just makes it look like the wrong answer, even if it was the right answer. And I can't verify it as an employer, so it's always like, oh, to hear that one. just lie to me as an employer. Just, say it was of,

Bekah:

What if you don't have a good lying face?

Bryan:

Well, I guess that's tougher.

Bekah:

Turn camera off. I'm sorry. I'm having issues with my camera. it was totally fine.

Bryan:

I'll answer this question.

Bekah:

I feel like you have a really good gut instinct for things. Do you, would you agree with that?

Bryan:

I like to think I do Who knows how true that is, but, um, yeah, I think so.

Bekah:

And what do you think. I feel like this is a silly question. Can you develop a gut instinct?

Bryan:

Um, I actually think, yes. Um, I, I just don't know how to teach it. I

Bekah:

Yeah.

Bryan:

that you can, you can develop something you kinda have to develop on your own it's cause it kind of also depends what we're talking about by gut instincts. So there's sort of a couple of different things that play in that. So like I have a pretty good read for people in general. I think, um, and that's, that's, it comes with extreme risk for bias. So I always try to

Bekah:

Yeah,

Bryan:

it by looping and lots of other people. I'm never the final arbiter of this kind of stuff, unless it's universally a positive, like sometimes I'll I have in the past taking a unilateral, like positive decision, like I'm going to hire this person because I think they're great. Um, I, I very rarely, almost never have taken unilateral. I'm not hiring this person because I don't like them. Like, I always try to make sure that I'm mixing in people to sort of check me on those kinds of things. Um, but separating that, that acknowledged concern for bias. I do think I have a generally a good impression of people and sort of what I think they can do or, or excited to do. You know how they'll fit in certain roles. Um, there's also like gut feeling for just general things like career things. Does this company look exciting? Do I think that the leadership that I am talking to actually sounds good or bad, and guess it has a little bit fits into the people analysis, but, um, it's like parallel versus directly in the same line. Um, and so a lot of that I think just comes from experience. Like you can have a decent, like, general intuition for it, but most of it you just learned. I've talked to 20 companies in my career, and these are the things I keep seeing in companies that burn out later. And these are the companies that keep seeing in companies who I remember and have good relationships with the founders with. And you sort of like start to develop that checklist of like what you're looking for when you're talking to potential employers or you're talking to potential employees.

Dan:

No.

Bekah:

is that, that Bryan Healey book coming out that specific one.

Bryan:

Yeah. So ironically, um, it, it probably needs massively updating. So I actually, I wrote like I self published it kind of silly but it was basically just the collection of old essays on this, these kinds of topics, like years ago, that was like the kind of crap I see in startups repeatedly. And I find interesting. Um, and I I've always wanted to do one. on like people too, but that one's also a little bit. Riskier.

Bekah:

Yeah.

Dan:

No, we got to come up with a pseudonym for you for publishing. So that'll be a Right. Ryan, Ryan feely.

Bryan:

feely.

Dan:

I don't know.

Bryan:

It's a name. It's not a football player. Oh man. He's like my, uh, ultimate ego.

Dan:

I'm still thinking about the helium named for that PHP thing is amazing.

Bryan:

as I ran through, that was my nickname. All through grade school was always Yeah. That's where it came from.

Bekah:

That was fantastic. Um, okay. So, so through all of this and what you're working on at Aiera, you're doing a lot of machine learning stuff. And so you know, there's been a lot of advancements, I guess, over the past, even couple of years. And like, how does that, you think that like, that's part of what's kept you interested? Like it keeps growing, it keeps changing. It's a fun field to be in. And like, but also it's overwhelming. Cause there's so many changes. So how do you balance that? Like, this is cool versus like a, I don't even know where to start.

Bryan:

So machine learning is my favorite field of any career I've ever been near specifically because it's just. Lunatically fast-paced like tech in general is fast paced. Machine learning is insane. I can't even, actually, uh, I had the, um, a friend of mine talk about it. Like we shouldn't talk about machine learning engineers, like wine vintages, like, oh, that's a 2007 machine learning engineer. know, you know, Keras and because. Rapidly you lose your, you lose yourself. Like, oh, I haven't worked in, in Keras in five years. What's it working on? Oh my God. Look at all this stuff. You know, they come with all these prebuilt models now. Like everything's just always moving at such a pace that yes, it keeps it super exciting. a little stressful, like always think trying to stay on the cutting edge and learning new things and keeping up on what's new. Yeah. But I think, I think you're right in that it, it hits that side of the brain. That's like, I'm never bored. There's always something kind of neat going on in this space. Um, and yeah, so I'd say that's, that's pretty much the gist of there and it's sort of funny. It also fits into the same medium that tech in general kind of fits for me, is, um, I'm trying think how to phrase this, but like learning makes me feel this especially, but really all of tech is that it's not really an industry in a classic

Bekah:

Hmm

Bryan:

It's like it's just there in everything, you know, there's, there's healthcare tech, there's legal tech, there's finance tech, there's, it just, it fits into every vertical pretty much. And so not like I just sit and code for the sake of code. I'm always serving an industry of some kind. Uh, and I, so I can go into any of these and sort of play, you know, I, in my career, I have worked in health tech. I've worked in consumer tech, I've worked in retail, I've worked in voice assistance. I've worked in FinTech and I've worked in travel and, and actually more and more, like, you just always get to sort of play in these different spaces. And so both tech and machine learning, especially allow you to sort of like never get bored in a single space where you just like, I just know this head to toe and it's not driving the excitement anymore.

Dan:

Yeah, I love that. You know, I've always felt the same way. It's, you know, it's another, another bonus of either moving, moving jobs or, you know, being independent or all that stuff is like you get into a different job and all of a sudden it's a whole new domain to learn. Right. And you don't have to, like, I don't know. I, we, we work on, um, I don't know, gas pressure valve, a company that makes those right. But I'm like writing JavaScript and stuff, you know, but at the same time, I know a whole lot about gas pressure that I didn't before. And that sounds like I wouldn't like say I'm going to, I'm going to do like chain. Yeah, exactly. Like, that's what I mean. It's like you get to nerd out about, um, about something new all the time. Uh, aside from the technology that you're actually like building.

Bryan:

And to your point, without having to make the commitment being

Dan:

Right, right.

Bryan:

I have to change careers to learn

Dan:

Right, right, right,

Bryan:

you

Dan:

right. Yeah. No, no. I'm not going back to school and becoming, you know, some sort of mechanical engineer and learning about gas lines and stuff. It, you know, but there is a certain amount of it that I have to learn just to do a good job, you know, and same, I'm sure at the same as with every single industry that you're in, it's like, it's just a new, a new puzzle to like, learn about.

Bekah:

Well, I think it's interesting too, because a lot of early career people or people who are coming into tech, the thing that you hear is, well, do you enjoy front end or do you enjoy backend? Which is really hard to tell because you've been working on these very basic understandings of all of the things. And so I don't think it gives a really good. Um, amount of experience, but you might really enjoy front-end dev in one portion of an industry. Like maybe you love end dev in healthcare stuff, you hate front dev in another sector of the industry. And when I. I've never really thought about it broken down, but I think like, even going back to Jessi's podcasts from the beginning of the season where she talked about that guy who was talking about the sandwich shop or deli, right. Like he was interested in the deli. And so he built something, Jessi was interested in chess. And so she framed everything along those lines. And so in the same way, if. you feel bored in whatever industry you're working in, but you like front-end dev or you want to give it a try, then maybe just try a different industry. And that might be more exciting to you.

Bryan:

For sure. absolutely. I mean, I think there's a lot of, try to think how to phrase this. Like, I feel like. I, I want to say this for career changes. This is probably even true for just young people, people in college. There's a, there's like a lot of this, I think, pressure to understand what you want to do and sort of

Bekah:

Yeah.

Bryan:

into it. And so there's like this of like evaluating things like, oh, do I like front end or like back end? Do I like machine learning to like, to. And my, my generalized advice in my career as it's progressed has always been like, do that. Just kind of do stuff I know that sounds so weird, but like,

Bekah:

Yes, sir.

Bryan:

one of the few industries where you can do that. for the first several years of my career, I was a front end engineer. Anyone who's seen things. I created know that that was a bad decision.

Dan:

Um,

Bryan:

front end skills whatsoever. I can't design anything. And yet there are three ish websites world that I designed. God help them. Uh, you can still find them on archive.org if you want to. it's like, that's okay. Like I fiddled in a space. I even got to get paid for it. And then I was like, this is really not going to work real for me in the long-term it should, I should do something else. And I would experiment with data science. Uh, I would experiment with backend projects and server infrastructure and. Doing things. Uh, it's a big reason why I'm a big fan of early engineers being full stack, just do stuff like willing to make APIs and front end designs and play, you know, an API development and database architecture. And, you know, it's also why I kind of advocate for young people, try a start up or two, because you're going to be in a space where that

Bekah:

Yeah.

Bryan:

as a forcing function, like you're one of five people you're going to do everything. just have to.

Dan:

Yeah, I totally agree with that. And like, I'm glad you said that because it's. It's the kind of advice I've wanted to give as well. And I struggled giving it, I took it like putting it into, into like phrasing it. Well, you know, but that like just stop worrying and just, just do the thing or whatever, you know, like, uh, you know, jump in and, and build.

Bryan:

And I mean, I'll also, I'll even admit, I mean, just for the sake of devil's advocate and B can be, you know, admitting to the, the risks there's downsides to that too. There's not a lot of like, um, there's not a lot of good mentorship in tech either because

Bekah:

Yeah.

Bryan:

Like, there's, there's not a lot of like, um, what's the word I'm looking for? Um, There's not a lot of like apprenticeship paths in tech where you can, like, want to try this. I'm gonna spend two years working with people and learning. It's more like, here's the thing. Good luck. You know,

Bekah:

Yeah.

Bryan:

a lot of that in tech and that can be a negative, but I, you know, just because of my nature, I like to spin that as a positive and be like, yes, that can be stressful and it can have its downsides, but it also means that. And have the flexibility to learn at your pace, to learn on your own, which is always fun. And it's rewarding when you pull things off and it means that you are never get yourself stuck in a path. You're like, crap, I've spent five years on this thing. I don't like now, what do I do? I can't just pivot now. Yeah. You can just keep moving until you find things you like and as an industry that uniquely affords that without much downside risk. Okay.

Dan:

Yeah, all of that. It, and it's, it's so true. And I wanted to call it that advice of, um, that you dropped a minute ago. Having a, when you're early career like joining a small team, you know, where you're going to get that, there's probably going to be a little more pressure on you and maybe a little less, you know, structure, uh, to support you, maybe, you know, but the, but the, the, the bonuses of it are so are so large, right? And then you get the exposure across like a whole, a whole, like a large amount of space. Right. And you're going to end up, like, maybe you're gonna end up doing some database work and also some front end, you know, react to worker. PHP or whatever it is, you know, like whatever they need, right. Because that's what they need. And, um, if you, at least, if you can trust the organization to be okay with you learning on the job, you know, then like that's the best way to, that's the best way to get all of the experiences. I think that's great advice.

Bryan:

And it's sort of like, there's sort of an interesting identity to that that has an element of risk to it. I'll admit like, obviously it sucks when you fail and that happens sometimes and I'll always coach people to be like, that's okay. It really is. I promise, know, you used to learn. The same token by taking the risk where you might fail those times where you do get thrown in the deep end, thrash around and learn to swim, feel like heaven. It's like, I conquered this. This is my thing. Look what I just did. That's that's a great feeling. And there's not many places where you get to experience that so often.

Dan:

I love that. And yeah, that is the thing that happens all the time in tech. It, it, you know, it's small ways in big ways, you know? Even just squashing that bug that was driving you crazy for a hours or whatever, a couple of days, you know, that feeling, uh, vanquishing it, you know, it's like such a, such a good feeling. And, uh, you know, that can scale all the way up to career challenges and all that stuff. I love that.

Bryan:

Yup. For sure.

Bekah:

Yeah. And I think that's one of the biggest takeaways that, that anybody can have from what they're doing, especially early career people. There's just this, focus on failure for whatever reason, you know? Really flipping it on its head. It's not a failure. So what is it like, how else can you reframe how you're thinking about this job experience? What have you gained from this? And really like, kind of addressing like, okay, well, you know, like maybe it's just, I learned where my limits are. I learned that I will not let treat me like this in a job situation, it's I learned that should ask for help sooner. Or, you know, anything, you know, I I've, but thinking about what you've learned in doing that self evaluation is not something that we talk about often, but I think that it can help combat a lot of the problems that we see with early career people who leave the field, even people who are interviewing, right, because. It's really hard to interview. If you are interviewing for junior level position, there's a lot of people interviewing for junior level positions right now. And to get turned down, it's not a failure. about what you've learned, about how you can take that moving forward and, keep using that, you know, build on that. Well, this has been a really great conversation, Bryan. Um, but we are just about out of time. So is there any last tips that you have for our listeners, about career or startup life?

Bryan:

Oh, boy. I mean, that's dangerous. I could probably talk forever. I mean, I guess the last tip I'll sort of piggyback on something you were just saying. I think it's worth addressing, I've said it before in different contexts, but I'll say it again, which is like, especially with things like interviewing. Remember that that's its own skill. And, and, and to

Bekah:

Yeah.

Bryan:

that a little further, most of the things in this space are their own skills. And it's almost a problem that we'd lump them in with the word tech it's like saying medicine. Like a surgeon is very different from nurses, very different. Like th there's a series of skills in this space. And so to your point, struggling with any one of those at any one time, even, you know, getting better at it than struggling. Again, none of this really means anything about you as a person doesn't mean anything about your career path. It just it's its own skill that might need, um, a little workout once in awhile, like interviewing is its own skill. It's a hard skill. You might get good at it. And then it might go five, six years before you're interviewing again. And now you're rusty. Like that's also fine.

Bekah:

Yeah.

Bryan:

just always give yourself grace in this space of being like, not failing. You're just sort of like working muscles as you go. And sometimes those muscles take longer to develop. you develop them and let them atrophy. That's also fine. You can redevelop them, like just let yourself grow at your own pace and just be willing to, your point. Just take lessons from things that don't work out and keep moving.

Bekah:

Yeah, that's awesome. And for those of you who don't know, Bryan is very, very strong as well. so I'm going to keep going with this, this analogy here, because I think like there's some days you go to the gym, right. And you can lift that heavy weight. And two days later you go back there and you can't lift it, you know, what, what has happened. Right.

Bryan:

yeah.

Bekah:

know, A number of conditions that can happen that you just can't, you can't hit it that day, even though it was easy two days ago, that's like, it's exactly what you're saying about interviewing.

Bryan:

Totally. And I mean, I'll even extend that further to something, which I really. I I've, intense ADHD. So my focus is all over the place. There are some days where I'm walked in and I'm writing code and working and managing, and everything is sort of running smooth. And then I'll have, I'll have two week long stretches where I'm just kind of like feel a little bit, you know, and

Bekah:

the listeners, Bryan, Bryan is sitting there with his hand

Bryan:

just

Dan:

Yeah.

Bekah:

in his hand, just living around.

Bryan:

sort of like looking into space and it's like, and it's. I don't know why I have always been able to all the way back to school days I'm always been able to just be comfortable with that. Everyone else I've had this very sort of, um, be a little vulgar for a moment. I always, I always joke that I have a very Boston f you attitude about life. Like worry about my thing. You worry about your thing. We're all gonna be fine. You know? And so I've always been very comfortable with the fact that like, that's, that happens to me sometimes. And it's like, well, the next two weeks are going to be some {stuff} and I'm just going to drink some coffee and, and try to muddle through. But I know a lot of people struggle with that. And so like my advice generally, Try as best you can, whether that's through your own self coaching, whether that's to outside mentorship or even therapy or whatever things needed to get you there to like, be comfortable with your own unique way of managing yourself and your life. Not everybody is going to be in the same boat um, and that's okay. And you just sort of like learn strategies and learn methods to sort of do your own thing.

Bekah:

Yeah, absolutely such great advice, Bryan, this has been a great conversation. And anyone has not met Bryan, you're missing out because Bryan always has advice and hot takes for days. So, very much have enjoyed this conversation. Thank you so much for being here with us today.

Dan:

Bryan

Bryan:

It was a lot of fun.

Bekah:

All right, well, we'll talk to you soon. Bye.

Bryan:

Sounds good. Bye.

Dan:

Thank you for listening to this episode of the Virtual Coffee Podcast. This episode was produced by Dan Ott and Bekah Hawrot Weigel, and was edited by Andy Bonjour at GoodDay Communications. If you have questions or comments, you can hit us up on Twitter at VirtualCoffeeIO or email us at podcast@virtualcoffee.io. You can find the show notes, sign up for our newsletter, check out any of our other resources on our website at virtualcoffee.io. And of course join us for our Virtual Coffee Chats every

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The Virtual Coffee Podcast is produced by Dan Ott and Bekah Hawrot Weigel and edited by Andy Bonjour at GoodDay Communications.