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David Aviles
Getting knocked down twice, right before the big moment, and what he chose to build with the time that gave him.
David Aviles
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Life Between Titles

He Got Fired Months Before His Startup Hit a $500 Million Valuation. So He Started His Own.

with David Aviles

🎧Spotify

David Aviles spent his career in early-stage tech sales at Optimizely, Amplitude, and Mintlify, and got fired twice — both times just before the company he'd left took off. He hiked alone into the Marin Headlands to decide what came next. Conversations with contractors working on his mother's house became the idea for the company he's building now, for the trades industry his own brother works in.

Key Takeaways

  • Entrepreneurship starting at age 11 with a newspaper route: David's first business came from scanning the newspaper classifieds at 11 to find a delivery job, then pivoting at 12 to a lawn-mowing operation after he couldn't stand the 4:30 a.m. wake-ups — landing his first 'enterprise deal' from a realtor who needed weekly service for three months while a listing sat on the market. He estimates he earned about $3,000 off that single client.
  • Transferred to Berkeley through a community college back door: After being rejected from his top choices and committing a deposit to UC Davis, David received a letter from Berkeley about a transfer pathway for high-potential students. He spent two years at Diablo Valley College, transferred to Berkeley, got into the impacted economics program, and worked 20–30 hours a week at Ruth's Chris Steakhouse the entire time — which he now cites as his one real regret from college.
  • Fired twice, each time used it as a launch pad: David was fired from Optimizely a quarter after a promotion — an experience that left him 'bawling' — and then from Mintlify (which later raised $45M from Andreessen Horowitz at a $500M valuation) with no warning. Both times he reframed the firing as evidence he could set his own ceiling, ultimately using the Mintlify departure as the permission slip to start his own company.
  • Switched to customer success to support his mother's crisis: When David's mother had a nervous breakdown and he became her power of attorney — cleaning out a hoarded house and managing contractors for months — he quietly requested a transfer from his Amplitude sales role to customer success, never telling his manager the real reason. He got promoted within seven months and then transferred back to sales as soon as the situation stabilized, parlaying the renovated house into an investment property.
  • Building AI for trades and services because he watched his brother struggle: David discovered his startup idea not through market research but by interviewing the contractors working in his mother's house, then watching his own brother — a handyman — struggle to find leads, invoice clients, and get referrals three years into the business. His company (currently called WorkTrue) targets solo operators and small teams in HVAC, plumbing, painting, and contracting with an AI-driven one-stop shop for lead response, scheduling, invoicing, and reviews.

In This Episode

  • How an eleven-year-old paper route turned into a lawn-mowing business that made $3,000 off one house
  • Why graduating into the 2008 recession sent him into a toxic recruiting agency
  • What changed when he joined Optimizely, and why they fired him a quarter after his last promotion
  • How a solo hike in the Marin Headlands helped him decide to bet on himself again
  • What happened when he got fired from Mintlify months before its $500 million valuation
  • How conversations with contractors working on his mom's house became the idea for his new company

What We Discuss

00:00Intro
05:00Growing up the youngest of five in Concord, CA
13:00The paper route and lawn-mowing business
17:00Feeling his way into UC Berkeley as a first-gen student
23:00Graduating into the 2008 recession and the toxic recruiting agency
26:00Joining Optimizely and the culture shift that changed everything
37:00Getting fired a quarter after his last promotion
42:00The hike in the Marin Headlands and betting on himself again
55:00Fired before the company's $500M raise
58:00The conversation with contractors that sparked his startup
1:08:00The elevator pitch for his new company

Q&A

Questions answered in this episode

How do you get into tech sales without a tech background?

David graduated into the 2008 financial crisis with a Berkeley economics degree and spent two years serving tables because no one was hiring. He took a 10K pay cut to join a technical recruiting agency — a full-desk cold-calling role — purely to get a professional credential on his resume. From there he parlayed the sales fundamentals into an SDR role at Optimizely, describing the move as deliberately going backward in seniority to extend his long-term ceiling.

What is it actually like to work at a high-growth startup like Optimizely or Amplitude?

David describes Optimizely's culture around 2013 as built on values he'd never encountered before — ownership, transparency, growth mindset — and says it 'humbled' him into wanting to become a student again after years of figuring things out on his own. At Amplitude he went from roughly employee 45 through the company's journey to $80M ARR and an IPO, working in both sales and a year-and-a-half stint in customer success before leaving when the manager path he wanted didn't open up.

How do you cope with imposter syndrome when starting a company?

David says he experiences imposter syndrome 'already' in the early stages and counters it by recalling that every time in his career he has doubled down on himself — taking the toxic recruiting job, stepping back to an SDR role, moving into customer success for his mother — the bet eventually paid off. He acknowledges that the fear of letting investors down is actually what led him to initially plan to bootstrap rather than raise, because he doesn't want to take money before he can protect the downside.

How do you balance starting a startup and starting a family at the same time?

David is candid that there is no right time for either — he draws the parallel explicitly, noting that everyone told him the same thing about having kids. He is currently doing fractional consulting work to pay bills while building the startup, and manages the fear of failure by telling himself that the statistical odds against startups are exactly why the bet on himself has to be total rather than hedged.

What market is WorkTrue (David's startup) going after and why?

David is targeting solo operators and small teams in the trades — HVAC, plumbing, painting, handyman, contracting — specifically because he believes AI will not replace those jobs for the foreseeable future, making it a durable market. His pitch is an AI-powered one-stop shop covering inbound lead response via voice and text agents, scheduling, invoicing, payments, and review generation — the exact workflow problems he heard from contractors working in his mother's house and from his own brother's handyman business.

Full TranscriptLightly edited for readability · click to expand

[00:01]

Savan Kong

Welcome to Life Between Titles. I'm your host Savan and today I've got my good friend David Avalas. David, good morning. How are you? Morning. You know, still getting topics. Yeah, do it, man.

David

Morning, morning. You know, still getting the the coffee in, so I hope you don't mind me grabbing a little bit here, but no I'm I'm doing good, man, I'm doing good. How are you?

Savan Kong

You know what? Like it's it's not raining here in Washington and the kids got off to school on time and I can't complain, dude. You know, it's like one of those mornings where it's chill and I'll take every chill morning I can get, brother. David, here's where I want to start, my man. Here's where I wanna start. So, you know, one of the good things that I love about LinkedIn, and there's a lot of shitty things about LinkedIn, like people, you know, putting things that they actually are doing that may not be representative of real life. weird. Hold on, brother. This is I don't know why it's like it's trying to reconnect here. are you on Wi-Fi by chance?

David

I feel it. Sounds good.

David

am. Is it not strong?

Savan Kong

Am interesting. not strong. Yeah, for some reason it was trying to reconnect and I don't know if that's like a thing on your side or on my side. I don't think it's on my side. This is Okay.

David

Yeah. Hold on one second.

David

I'm gonna keep the door open there, cause the Wi Fi is like not coming in very strong. Sorry, I just sucked my wife real quick.

Savan Kong

I'm gonna keep the door open there. Okay. Yeah, it's all good. It's all good.

David

We had checked the door, but sometimes that makes it a little weaker, so

Savan Kong

We check the door but sometimes that makes it the the funniest thing, like the the the little hacks you get. You're like I've gotta keep the door open for the Wi Fi.

David

I'm like, bro, can we're in twenty twenty six, like we've been working for home for six years. Can it not just be solved already? Like I don't know, my last house, like we moved a year ago, it was totally fine. And then now it's like I don't know, like I I only learned that because I was like on a call and then I shut the door and then suddenly everything was like messing up. So I like, Alright, guess I keep the door open now, whatever.

Savan Kong

Twenty twenty six, like you worked for home for six years because it's not just be solved already. Like Yeah. I don't know, my last house, like it was totally fine. Yeah, now it's like like a I don't I only call and then I shut the door. yeah. So I was like Yeah. I mean it's a little better, so whatever hack you got going on seems to be working.

David

All right. Well I mean I got a direct line. I can see the router right here, so should be good.

Savan Kong

Okay, let's get started. And I think like to maybe compensate for potentially any of the lags, I'll I'll I'll I'll have a beat and then if there's a couple seconds pause, I'll continue the converse the conversation, but we'll we'll give it a little bit of buffer to make sure that the internet connection is keeping up with our conversation. How's that sound?

David

Yeah, yeah, yeah. Sounds good.

Savan Kong

Yeah, yeah, yeah. All right. All right. Well, let me restart the original question. So, David, you know, the thing I love most about LinkedIn is not, you know, where people promote if they got a new job or what they're doing or what conference they're going to. It's the ability for people like you and me who met over a decade ago, at two different places, Reconnect and really like stay engaged, right? Like, and and like I've been following your career trajectory over the years. I'm sure you've been doing the same thing with countless amounts of professionals, man. But for the people that are out there that don't know who you are, give me a one-liner about who you are right now in your life that you would tell a total stranger. What would that sound like?

David

Man, that's a great question. To a total stranger, I would probably just tell them that I am trying to start a family with my wife of three years and also build a company at the same time.

Savan Kong

Yeah, dude. You're you're a brave man, as I've told you over the phone, trying to do both those things at once because neither one of them is for the faint of heart. And it takes balls of steel to to try to juggle that. and we'll get to that, and I think that's gonna be a core of our conversation because today I wanna dive into how you got to where you are right now as a founder of a of a startup.

David

Yeah.

Savan Kong

And how you got to where you are as a family man. But before we get to the juicy parts, tell me about where you grew up, brother. Like what shaped you to be the man you are now? What did high school look like? Where was that at?

David

Yeah, absolutely. I actually had my aunt over for lunch this past Saturday. We meet up every couple months. She lives here in San Francisco, not too far from me. And she told me of her text message that she's she's from my Puerto Rican side of the family, Puerto Rican Spanish side of the family. She's like, I want to cook lunch, I want to listen to Puerto Rican music, and I wanna really get to know you. And my aunt's kind of a hippie. So I was like, Yeah, sure, I'll see like whatever you want, you know? and the first question she asked me was, so

Savan Kong

Yeah, yeah, yeah.

David

What are your core beliefs? Like when you grew up as a kid and through your life, what what were those core beliefs that stuck with you? So without knowing, I I had a little bit of a chance to practice for this question, I guess. But I mean, man, I could talk about this all day, but I think the way I like to say it is, you know, I I grew up the youngest of five. My mom had two sons in her first marriage, my dad had two daughters in his first marriage, and then they married in you know, had the sort of Brady Bunch thing going on. But I came out as a surprise, and you know, was the youngest of five in a pretty chaotic household. Like my oldest sibling, my sister was 18 years older than me. My closest sibling in age was my brother. he was six years older than me. So a huge gap in age. And you know, I wouldn't say that my siblings were were perfect little angels either. They had a lot of stuff going on with all sorts of things that you might expect of P pubescent through just graduated high school age folks. And you know, something my mom always told me growing up that to just for some reason just always stuck with me since I was a little kid was you're allowed to make mistakes as long as you learn from them. And I I really took that to heart, like I said, not just for myself, but in

Savan Kong

Mm-hmm.

David

Thinking about others, like when I see my brothers messing up or getting in trouble, or my sisters messing up or getting in trouble, I'm like, well, I don't need to make that mistake too to learn from it. I can see them fucking up and not do that. And so, you know, not to say they weren't total fuck up. I'm I'm making that sound hell like horrible right now, but point is I was able to learn from their mistakes as well as my as well as my own. And you know, but

Savan Kong

Yeah. Yeah, yeah, yeah, yeah.

Savan Kong

Yeah.

David

sort just brought that with me all through life. And, you know, I grew up in the East Bay here of San Francisco in a city called Concord. It's a suburban town. not particularly nice, not particularly horrible, just a kind of a standard middle class suburb here in in the Bay Area. went to went to public school. I was in one of those gifted and talented education programs that apparently get a lot of heat now, at least so says my social media.

Savan Kong

Yeah.

Savan Kong

Right.

David

and yeah, throughout high school I was kind of I always described it as just like just feeling my way around. I had no there was no precedent for what I was doing. I was playing sports, I was working, I was, you know, top of my one of my, you know, one of the top of the class of our school and like my family never had that. And so I was just kind of figuring it out as I went.

Savan Kong

Yeah.

David

Like I didn't know if I was supposed to be talking a guidance counselor about college or like what, right? Like it seems so obvious now, but back then I just like I said, I was I was kind of just feeling feeling a way around and then I found a way forward, I would I would go forward basically. and yeah, we we basically just, you know, did what we had to do and just worked, man. I always say that's like one thing that like I I posted about this on LinkedIn recently was like

Savan Kong

Sure.

Savan Kong

Yeah.

David

My superpower isn't necessarily being the smartest guy in the room. My superpower is being able to outwork the competition, the person next to me, my neighbor, whatever. and I I think that's just sort of what got me through those high school years. I don't know if you want me to go beyond that, but

Savan Kong

Yeah. And the person next to the name Yeah.

Savan Kong

No, that's great, man. That's great. I I wanna I wanna dive into that a little bit and talk about what that work ethic looks like. Do you feel like being the youngest of a family of five? And I I'm the youngest as well by the who's closest to me is eight years older than me. and so I it in some ways you you are an only child, but not really. Like you you you have a lot of the benefits, but you also have a lot of the downsides of that, right? Because the age difference is so great. for you, what was that like? Like how did that how did being so much younger than your brothers and sisters instill that sense of competitiveness and that work ethic?

David

Yeah, I think the reality is that like by the time I was like forming actual memories, only one of my siblings still lived with me, which was my six year old my brother that's six years older than me. 'Cause my my next sibling is twelve years older than me and the next one after that is thirteen or fourteen years older than me. So by the time I was like six, they're already out of the house. Right. And like that's when you're really starting to be like a human and and remember things.

[10:06]

Savan Kong

Right.

Savan Kong

Yeah.

David

And so it was mostly just me and him. We were definitely like not only close to finage close to fire relationship. He was my best friend, he was my like mentor in a lot of ways, like the guy that just even though he wasn't necessarily doing all the things that he maybe would have wanted to do, he was like always making sure that I was staying on the path. And so I think that was a big influence in my life. Like for example, when I played football, so I'm five foot four. You can't really tell 'cause I'm sitting down right now, but I'm not a a very tall guy. And you know, American football is usually bigger people, right? but I've always been super competitive, like you like we're just talking about. And I've always been decently athletic. So I went out and played anyway. And my brother also played in high school, but he never actually played. He was on the team, but he never actually got any real playing time. Maybe some like, you know, garbage time here and there, or special teams or whatever, but

Savan Kong

Yeah.

Savan Kong

Yeah.

Savan Kong

Mm-hmm.

David

he told me and 'cause asked him, I like, Man, if you're not even gonna play, like, you know, when I was like a little kid, I was like, What's going on? And he's like he's like, Look, like I probably will never get playing time, but I'm gonna put it like all out I'm gonna leave it all out in the field every time I go out there, whether it's practice or even if it's garbage time. So I know that I did everything I possibly could get everything I possibly can out of it. And I was like, Damn. Okay, I I see you like that.

Savan Kong

Yeah, state.

David

That that really stuck with me too, you know. And so when I went out there, I didn't care if I was the smallest, I was just trying my hardest and putting extra practices together and like recruiting guys to work out with me when we didn't have mandatory workouts and practicing the drills and and all of this stuff. And when my time came, there was an opportunity where I I could get a starting position in my senior year. And yeah, I got it. I started our entire season. and

Savan Kong

Right.

Savan Kong

Wow.

David

You know, that when you talk about that competitive drive, it's just honestly most of it just comes from the family environment, not just from being the youngest, but I think from having that sort of guiding light with my brother and parents who basically just let me do whatever I want. I think they were tired by the time they got to me. They were like, Man,

Savan Kong

Yeah.

Savan Kong

Yeah, no, I I I love that.

Savan Kong

Yeah, I love that man. I you know, I read somewhere you had posted that at at twelve you were mowing lawns and posting flyers and you used the funds from that little operation to buy a basketball hoop and I I just find that to be so fascinating, especially being a twelve year old and my daughter just turned thirteen, so I'm like trying to put that into perspective of the amount of entrepreneurship that it takes for stuff like that, you know?

David

Ha ha ha.

Savan Kong

How how how did you get into that little operation? And I think more importantly, like what what was your learning lesson at that young age from that?

David

I don't know. Like when you're that age, you get an idea in your head. Usually it's like a fleeting idea and then you forget about it. But something about me, man, whenever I get my eyes locked on something, I just I get it done one way or another. And I if you read the whole post actually, I started at eleven years old. So when I was eleven years old, I really I forget what it was at the time. It might have been a dreamcast or whatever whatever it was, right? I I wanted something.

Savan Kong

Yeah.

David

And my parents were sure for sure were gonna buy it for me. So I opened up the newspaper. I found a newspaper delivery job. I called them. The woman sounded very I remember she sounded very confused on the phone because I must have found it like a baby. I went over to her house. I will never forget this because she was a very memorable woman, I will say. And the house was a little crazy and hectic, but she was like, She kinda looked at and I was with my dad and she was like, All right, well here's your route and blah blah blah.

Savan Kong

Yeah.

David

So my dad would wake up with me at 4 30 in the morning, we're rolling newspapers, he would drive me around and I'd toss them out. I would go door to door. This is the crazy part. Like waking up at 4 30 in the morning is when you're on delivering newspapers. That's pretty crazy, I guess. But I was actually responsible for collecting payment for these subscriptions from my neighbors. So I would and and my by the way, it was not my immediate neighborhood, it was like one neighborhood over. So I didn't actually know these people. So I'd like literally like knocking on the door, like, hi, like you're 32. Dollars is due or whatever. I don't remember what it was, but whatever. And they're like looking around like, You're my delivery person? And I'm like, Yeah, that's me. and so I'd be collecting cash and checks and I go drop it off to this woman's house every month. And it was a trip, man. I remember too, 'cause I did it during Christmas time. It was like during the holidays, and a bunch of people left me like tips and like canisters of cookies and all sorts of stuff. And I I thought that was super cool. I'd never really

Savan Kong

Yeah.

David

knew that was the thing when I was 11, right? but I couldn't I couldn't take the hours, if I'm being honest. I I hated waking up that early. And so I was like, how else can I make money? And we had a a lawnmower. I saw people that had long grass around. I I went up, I got on my computer, I I typed up these posters and we put it in like a a child's fonts. I forget what the font name was called, but it was me and my buddy, my neighbor, we wanted to make it look like

Savan Kong

Yeah.

David

It was kids doing this and we just put ten dollars per lawn and then like little Yeah, something like that. Something like that. Yeah. And then like little sort of five print said depending on the size of the lawn. We were just trying to get them in with that ten dollars per lawn, right? And a lot of them we actually did for ten bucks per lawn. Mindy, this was whatever, twenty-five twenty-eight years ago, right? and so yeah, we just did that. And I remember my first

Savan Kong

Yeah, little comic sands font.

David

quote unquote enterprise deal came from this too. We ended up hooking up with a guy that was a realtor for a house that he he had on the market and it was like right up like right at summertime. for whatever reason it took him like three months to sell this house. So basically went through the whole summer and he had us out there mowing it every week, front and back and watering the lawn front and back if he wanted it to look good for his clients. Ended up making like three thousand dollars off this guy. So I hope you made money on the house because he definitely paid us

Savan Kong

Mm-hmm.

David

and it was it was quite an experience, but yeah, it was it was cool.

Savan Kong

That's wild, dude. I love that story, man, for so many reasons. David, take me back to your college days at at at Berkeley. You were the first one in your family to go to college. What what inspired you to to take a different route than your brothers and sisters? Like, how did that conversation go with your family? Because it's expensive, man. Even if you're in state, it's expensive and it's an investment. But like, what did that conversation look like for you guys?

David

Yeah, th this is one of those just feel around moments and and find your way forward because ever since I was a little kid, since I can remember, my family was saying, David's smart, David's gonna go to college, David's gonna be the one. And they kind of treated me as like the golden child in that sense. And so for me, when you you know, when you're a little kid and you hear this stuff, you're just like, Okay, that's that's that's my path. That's what I'm gonna do. Cause you don't know any different, right? And so for me it was just always what I was supposed to do and what I was going to do. And when I got there, right, like junior, senior in college or senior of high school, I'm like, okay, it's time to apply, time to get ready. again, sort of feeling my way through. I didn't have any of the like extracurriculars that all these other kids did. My CTs were good, but they weren't great. Like I never studied. I just kind of took them and, you know, the one time and that was it. I did have good grades. I was like top five percent of my class. So I figured, you know, like write a good entrance essay and I'll get in wherever I want. Ended up, but I got into some UCs, but I didn't get into my top which like Berkeley, LA, San Diego kind of thing. I got it at Davis and Santa Barbara and a few others, but and those are great schools. But in my mind, I was like, man, like I really want to go to Cal. Like this is the place I want to go. Like I want to be at Berkeley. Berkeley's like the best school out there. Like I just want to do this. And I was actually committed to Davis. I had like sent in my dorm deposit and all that. And I got a letter from Berkeley and it was like, hey, that you know, we noticed that you applied but didn't get in. We'd love for you to join this program. And it was like a transfer program. It wasn't like the guaranteed transfer program, it was some other assisted thing that they did for like high potential students or whatever. so I ended up going to my local community college, Double Valley College, DVC, spent two years there and ended up transferring. how and then once I got there, what I didn't realize was In order to get into Haas, which you is their business school, I would have had to wait another year based on the way that the the classes I would have had to take and the way that the admissions work. So I was like, Well, I'm not gonna do that. I wanna graduate in four years. So let me go do economics. I go to find out that economics is an in impacted program. So they only accept two thirds of the students. So I was like, shit, man. Now I'm at Berkeley, like competing for these, you know, these spots basically when all the with all these other Berkeley kids that have been there their entire like

David

college careers at this point. But somehow, some way, figured it out, got it done, got into the econ program. did not graduate with a very high GP, I'll tell you that. I was also working 20 to 30 hours per week. My mom, man, I love my mom and you know, I wouldn't be here without her. But the one thing that I really actually and I don't have a lot of regrets in life, but one thing that I actually really regret from this time is that I wish I didn't work or I worked as little as possible.

[20:01]

Savan Kong

Yeah.

David

You know, her whole thing, and like you said, it's expensive. You don't wanna graduate with all this debt. Like I've heard so many horror stories of students that are graduating, now they're drowning in debt. And so I was like, man, I can't graduate too much debt. I can't graduate too much debt. So I was working my, you know, butt off working at like Roos Chris Steakhouse and PF chain, serving tables, all this kind of stuff. and I didn't. I graduated with like I call it a Honna Civic's worth worth of debt on my name, at the time. And that's all great, but

Savan Kong

Yeah.

Savan Kong

Yeah.

David

I I didn't really get to focus on my studies. I didn't get to travel study abroad. I didn't get to join, you know, the campus activities and groups and and all this kind of stuff. It was like a very transactional motion for me. So yeah, one thing I would change is that, but I also worked thirty hours a week supporting myself going to full full time U C Berkeley Econ impacted program, which that'll build some character, tell you what.

Savan Kong

Yeah.

Savan Kong

Yeah.

Savan Kong

yeah. Yeah. I love that hustle, man. You know, I I I went to I went to Occidental my first year after high school. and you know, I think at the time this was back in nineteen ninety eight, nineteen ninety nine. It's still expensive. It was like forty grand, maybe, forty five with housing and all that, which is not a lot by today's terms by any means, but

David

wow.

Savan Kong

When your family's not well off, like that's a significant amount of money. And dude, I dropped out that first year to go work at a startup. And when I decided to go back to college, I w I finished up at UW. But I worked my way through UW as well because I was like, you know, my parents are gonna aren't gonna pay for this. And so I did the exact same thing. I was like literally working full time and then overloading every single one of my classes cause I was I was just antsy to graduate, bro. I just wanted to go work at startups, wanted to build companies and like this was the dot com boom, right? Like the early two thousands. And I just wanted to get out of there. And I I I I feel the same way as you, man. I regret not doing all the things that you should do when you go to college. Like build those communication skills and build that network and all those things. and it's just it's just a

David

Mm-hmm.

Savan Kong

A different mentality, you know, when you've got that drive to to get out and do things, right?

David

Yeah. Yeah.

Savan Kong

David, tell me about after college, brother. So you're did you start off as an SDR? Was that sort of your first official role or how did you get into tech?

David

man. I I I'm hesitant to say this 'cause like it's really, really tough. I think for any new graduate that didn't really have the sort of prep in the background that one might need to just like get a good job right out of school. It's really, really hard. Like I'm talking to my

Savan Kong

Yeah.

David

My barber, she's like a first generation Chinese immigrant. Her daughter's at San Francisco Bispo and she's working cra like way whatever I just told you she's like more than that, which is crazy. So I was like, man, like tell her to like chill, you know, take some take a break, like here are my lessons and she'll find a job, don't worry, and all this stuff. But she was like struggling to find internships and and all these crazy things. It's like super hard worker, super smart, super sweet girl. But basically I graduated in two thousand eight. Which was, as you probably recall, our generational downturn of the economy. I studied economics, like I said, at UC Berkeley, which I thought was going to get me into something finance related, which is like what 80, 90% of econ kids do, at least from Cal. But nobody was hiring at that point. All this is when all the banks were collapsing, right? Nobody lots of friends' offers were getting rescinded and it it was not a great time to be graduating.

Savan Kong

Yeah.

David

especially with an econ degree. So I was working at a restaurant at Ruth's Chris Steakhouse at the time and I was making like, you know, when I was put when I basically went full time, I was making like 40, 45 grand a year, which at the time was not that much lower than like an entry level job coming out of college. maybe not in finance, but like most other jobs. And so I was like, you know what? I'm just gonna ride this out. I've been working my ass off. Like I need a break anyways.

Savan Kong

Right. Right.

David

So I told myself I was gonna take a year. I went and traveled to Europe for like a month with some buddies, did the whole like backpacking Europe after college thing. but a year turned into two years, and I actually was just so desperate to get out of restaurants that I took a job at a recruiting agency. It was a technical recruiting agency, they call it full desk, which means You start with nothing, you're cold calling into candidates, you're cold calling into hiring managers, and you're trying to just build a business from nothing, basically. and just so happens that I'm super competitive, I like to talk. and it it suited me. Like I wasn't good at first. I was horrible at first, actually. I must got fired in my first couple of months, but I figured it out and ended up, you know, taking over as a sales manager for one of the highest revenue generating teams in the company. But I hated that job, man. It was it was a horrible environment. you know, my my boss, I still talk to every now and again, but and he was great as a boss, but that environment overall was was not for me. Wasn't getting migraines like almost every day at the end. and one of our one of my coworkers had quit and left to a company went to a company called Optimize Day, where she became an SDR. A couple months in, she's like, David, you gotta come over here, you're gonna love it. So of course I went and joined her.

Savan Kong

Yeah, my

David

over optimizely. And that was my first foray foray into actual tech sales where I started as an S Cr.

Savan Kong

Nice. What was tell me a little bit about the the environment of this recruiting place? Like what was the thing that caused you the most consternation and and stress? Like was it the people that was there? Was it the policies, the expectations? Like what was that like?

David

Yeah, it was a little bit of all of that. So I had never been in an a working environment, so I didn't really know what was like right or wrong. I realized it once I went to optimize sleep, but apparently it's pretty common for this model of like sales team where they recruit kids right out of college, they really grind them, build a book of business from nothing, pay them very little, and they kinda, you know, work their way up in commissions and base pay over time. So I didn't know that. I didn't know that was like a common sort of model that that companies did. I was just again trying trying to get into any kind of professional career. So that was, you know, hard. I was taking like 10K less at this recruiting company than I was serving tables for half the work, right? So I was like, all right, well, this is what I want to do. So like I'm gonna make this sacrifice. Like when I first moved to San Francisco.

Savan Kong

Mm-hmm.

Savan Kong

Wow,

David

I was depleting my savings because I was getting paid so little that I couldn't afford my room that I was renting in North Beach plus like my living expenses. And you know, that's motivation in and of itself for sure. Like you're like, I gotta figure this out and like make more money. not necessarily what I would recommend, but it it was the way I I got into it. And it was a lot of little lot of little cultural things. Like if you had to be in your desk ready to dial at eight AM every day.

Savan Kong

Yeah. And

David

If you were there at 8 01, they would take your seat away until lunchtime. So you had to stand up and we we sat in like a bullpen style. So there's like four desks pointing, like we're all looking at each other, kind of thing. And so you'd be standing up for, you know, that first four hours of the day. if you were late from lunch, same thing, you you lose your seat for the the second half of the day. one time I remember a colleague of mine that was in my team was like, I'm gonna go grab a cookie from downstairs.

Savan Kong

Wow.

Savan Kong

Wow.

David

And then she like gets up to go and the director is like, No, you're not and she's like, ha ha, good joke, I'll be right back. And he was like, No, sit down, like pick up the phone, start dialing. And she was like, okay. And like sat down and did that. And it was just a bunch of little sort of toxic stuff like that, where it was like not not how I operate, basically. so yeah, it was it was not fun.

Savan Kong

Yeah. Holy smokes, man, that sounds traumatizing, right? Like just the amount of things you see and hear there.

David

Yeah, w you know, it was one of those places where they they buddy you up after hours though, like take you to Happy Hour and buy you drinks and you know, take you to fancy dinners when you do well and that kind of stuff. But the day to day was like this is how they're trained to to like train their people, you know. And the model worked. Like the company did really well. So I don't you know, I don't I don't wanna blame the the folks in front of me that were doing it necessarily, but it was

Savan Kong

Mm-hmm.

David

Yeah, like I say, it's just not not my place. I don't know how many places they're still like that, if any, but from what I understood back then it was actually pretty common.

Savan Kong

Yeah.

[30:00]

Savan Kong

Yeah. Yeah, that's wild to me, man. the thing that I find interesting, David, when you tell me this story is, you know, you're you're this guy who's fresh off of waiting tables at Ruth's Chris, and you go and you trade that for a job that's toxic, that pays you less, where you're building debt in a city that's expensive, and all those things when you stack it all up to a person that doesn't know you and you tell them, hey, I'm gonna make this trade-off for this other thing that is has all these disadvantages, they probably look at you like you were crazy. But there was some method to the madness in your head of why this works for you. Tell me a little bit about your rationale. Like what was the driving force to push you through all these things that are clearly not a positive force in your life at the time. Like How did you get yourself to get up every day and continue to do the work that you were doing?

David

You know, I don't know what the saying how the saying exactly goes, but something about desperation drives like creativity and ingenuity kind of thing. and that that's basically where I was at, man. I was so done with working in restaurants two years removed from college and I just needed an I would have taken any professional job in San Francisco at that point. Just so happened to be that, you know, I came across this one.

Savan Kong

Mm-hmm.

David

And when it came to the day to day, it was for me, failure was not an option. Failure meant going back to working in restaurants or back to some other thing that I I hated even more than that. So it was like the lesser of the evils. And also like I said, man, I was naive. I didn't really understand that like you're not supposed to be treated like that in a professional environment and you're not supposed to have like whatever, like all these things. So at the time the the sort of naivety and just the desperation pushed me through a lot. Once I became a manager though, I started to know better and I started to talk to other professionals and I started to figure it out and like what other opportunities were out there. But I really wanted at that point to be able to demonstrate that I could run a team. And so I stuck with that for a little bit. and by the way, like when I went to Optimizely, I took another career step.

Savan Kong

Mm-hmm.

Savan Kong

Mm-hmm.

David

backwards essentially because I remember talking to recruiters and they were like, Well, you're a manager now and you run a team of five and like all this stuff. Like, are you gonna be okay taking an entry level sales job? And I was Yes, one hundred percent. Like I want to do this the right way. I want to be able to extend my ceiling and be happy when I'm doing it and, you know, all those kinds of things. But in the moment it didn't it didn't yeah make sense or didn't all all I cared about was just getting out of restaurants and staying out of restaurants. And then as I sort of figured out it became

Savan Kong

Right. Right.

Savan Kong

Yeah.

David

All right, let me just prove myself. So on paper, I'm easy to hire like the next spot.

Savan Kong

Right. Right. Right. Right. Right What was it about Optimizely? You said it was, you know, very stark contrasts between the recruiting place. When you got there, and I assume this is probably your first positive work environment, at least in tech. what was it about Optimizely as a company and as a culture that you think they did very well at, where you could grow as a leader and a professional?

David

Yeah. They man, so optimization shaped everything that I've done since then in tech, both from like a cultural operations perspective, as well as just my own professional development and how I think about sort of navigating my career. Because they were you know, I I went from what do you call it, like small fish or big fish in a small pond, to small fish in a big pond, or again, I'm not great with these idioms and sayings, but They were just growing at an unbelievable clip. It was all inbound driven. So at the agency we're cold call. All we did was cold call. There was no LinkedIn. There was no I mean, we had LinkedIn, we had email, but all we were doing was cold calling all day, every day. People were calling us to to do business with us at at Optimize. So it was like complete turnaround. And then in terms of the culture, man, it was it was one of those places where now now everybody talks about these cultural values and stuff, but

Savan Kong

Yeah.

David

You know, back in whatever this was, twenty thirteen or so. the ownership like I come almost remember all of them. Ownership, transparency, integrity, 'cause we had it was called Opta. It was almost an ex it was like almost an acronym of the name Optimizely. It was like yeah, I can't remember what it was. But basically with like ownership, transparency, integrity, growth mindset, like all these things that were novel to me at the time, but now you see them everywhere and they've just been instilled in everything and everywhere that I've worked. And it was so like mind blowing to me. You know, and it humbled me actually a lot because I I actually came up quick there. My first six months I got promoted to an AE. And the next eleven months I got promoted to the second level of AE and and all that stuff. So I was doing really well professionally, but it humbled me in that like, you know, as an eleven year old

Savan Kong

Mm-hmm.

David

Getting a new stripper out and the twelve year old, you know, mowing lawns around the neighborhood and never stopping and just figuring out. I always thought like I would do something on my own. But when I got there, I was like, Whoa, this is like a whole nother ball game. Like I'm not even in this arena yet. I haven't even stepped foot in this place. And it was crazy because if it really brought me back down to earth of like what was possible and also what I could do. and so I just wanted to really become like

Savan Kong

Yeah.

David

Like a student again, basically. Like just learn as much as I possibly could.

Savan Kong

Yeah. Yeah. I I I love that framing for so many different reasons. And I think we we all will probably be better off if we were lifelong learners. You know, it's like one of those things that that we take for granted when we get to a place of comfortability where you just think you know everything and you're you've been in this place for a long time and you sort of stop. putting yourself in uncomfortable positions and I love that for for you especially at that time. for Optimizely itself, like what were what were some of the skill sets that that you picked up because you're essentially an account executive and you know there's a lot of very soft skills that you have to learn very fast, right? You have to be personable, you have to be interesting, you have to nurture relationships and all these things. and they don't teach you that in college, right? Like they don't teach you how to be an e account executive. What did you learn there that helped propel you through th this growth that optimizely?

David

You know, honestly, most of my sales learning came after Optimize Lee. But what I did learn, and why I say that because we I had some the fundamentals from sales down from the recruiting agency. And so I brought that over to Optimize Lee and I knew how to qualify. I knew how to close. I knew how to kind of just do the steps. But when you get into like legitimate enterprise sales, it's a whole another ballgame. And

Savan Kong

interesting.

David

I didn't realize that when I was when I was there and actually that's you know, I don't talk about the lot, but I actually got fired. I got fired from Optimized League a quarter after my last promotion. Maybe that's a whole nother time or story, but basically, I wasn't learning fast enough. And I I you know, like you said, you have to especially in a high growth place like that, like you gotta keep up or you fall off. Like that that's it. Like, and it's tough because everybody's moving super fast. So even if your manager cares, it's not like they can necessarily do anything about it all the time. They can't just support one individual. They have like ten people in their team or whatever.

Savan Kong

Wow.

David

Do I think some things could have been done differently? Of course. Like every everyone would probably agree with that there at the time. But you know, I think the things that I did learn outside of those hard learnings in terms of being a salesperson was just being my genuine self, being as quick as I could to respond to people, really, really like understanding what they're trying to solve for. I think I did that really well on like a one-to-one level, and that's what got me to where I was. I struggled on the enterprise side was doing that one to many, because that's just a a standard requirement for selling an enterprise is being able to get a lot of different folks involved and aligned and on the same page and at different levels of the organization and different departments and and all this kind of all these kinds of things that at the time I didn't I didn't realize how important that was and never really figured it out. but there's probably a ton of little things I learned, to be honest.

Savan Kong

Mm-hmm. Right.

Savan Kong

Mm.

David

That was a while ago now, but the thing that really stuck with me was you know, that that relationship building, that trust building, that hyper focus on like what you're actually solving for that person and that company.

Savan Kong

Yeah. How did you how did you take those lessons that you learned from from being fired? Because I you know, knowing you for the last whatever decade and and seeing your trajectory, I think there's a lot of traits that you have that are similar to mine in that we strive to be the best in whatever we're doing. we're very competitive, type A, personable, and I think like Either you're getting laid off or you're fired, or even when you quit something, it feels like you've misstepped in some way. and you know, when you made this transition from optimizely to I I think it was Amplitude, right? Like right after that, like what did you take from that transition and how did you rebound? 'Cause like something like that, man, it's a blow to your ego, especially for people like us.

[40:20]

David

Yep. Yep.

David

It was hard, man. I I remember when I got pulled in the room and they they let me know they were letting me go. I was I was crying. I was bawling my eyes out. 'cause this was like all this all the story I've told you up to this point was like all leading up to this point of me being in this amazing place and having this amazing career with this amazing company. And within three months of getting a promotion it was gone. And I was just like, What just happened? Like I my mind literally couldn't process it. And I actually tried like interviewing for this customer success team. So I was like, no, I really want to stay at this company. I love this company, I love the people here. And the the success leader at the time was like, Look, you seem like a great guy. You obviously know the product and all that stuff, but your confidence is gone, man. I gotta tell you, like, you have no confidence right now. You gotta go fix that before you do anything. And it's just like

Savan Kong

Mm.

David

so you don't want me? Is that a no? 'cause I was just so shook up at that point, you know, I was rattled. And when I left, I really did some soul searching. You know, you talk about what did you take away from this? And it's kind of like I said up to this point, it's I just felt my way around. I figured it out. I was like, all right, do I wanna be in sales? Do I wanna be in tech sales? Do I wanna be in San Francisco?

Savan Kong

Yeah.

David

And I I remember I went and hiked up in the Marin Headlands area and I biked up there. I went up by myself and I hiked up into the hills and found like this secluded spot and I brought a pen and paper with me and I was just writing down all the pros and cons of my situation and like where I wanted to be in life and I was saying it out loud and just really did like some legitimate soul searching type type work. I promised myself after that that I was gonna do that once a quarter. I've done that exactly zero times since. but at the moment, at the moment, it was what was needed. And I realized, you know what? I I've always had a chip on my shoulders. I've been the underdog, I've always been the the guy that wasn't supposed to make it, or the that nobody had any expectations of, or the one they forgot about and were surprised by later or whatever. And so I kind of took it as that, which was like, you know what, fuck them.

Savan Kong

Okay. Yeah.

David

Fuck that company. And I didn't really mean that. And I don't mean I love that company. I love the founders of the people. But like at the time I had to like say, you know what? Fuck that. Fuck them. I'm moving forward. I'm going to stay in sales. I'm even going to go earlier than I was at Optimizy, where it's even harder. It's like even more of a challenge. And then figure myself out, whether I want to become a manager or go into partnerships. At the time, partnerships in my in my mind was the path forward. and and do that. And so I ended up finding amplitude.

Savan Kong

Mm-hmm. Mm-hmm.

Savan Kong

Yeah.

David

I was the fifteenth higher at optimized. I was like the forty fifth higher or something like that. and so, you know, really doubled down on it, challenged myself even more than I did the first time. So

Savan Kong

Mm-hmm.

Savan Kong

Yeah. How did you how did you s first of all set the expectation for yourself? 'Cause I feel like that is that is something that individuals that have high expectations of themselves usually accomplish most of the things that they set out to do, but a lot of times it's really s making those concrete enough where you can you can achieve them in in some reasonable way. so that's my first question is how did you, when you got into your next role at your next company, set those expectations? But I want to learn more about how you kept yourself accountable because you eventually did well at amplitude and you know, based on sort of like the company and and how it's done. so the outcome of that was great, but I want to know how did you set those bars and then how did you keep yourself accountable?

David

I mean, sales is a pretty is the most accountable role you can be in, I think, in any organization, because you're very measured, there are like very clear metrics, more than any other role or any other in any other in any other department, right? So that's sort of already assumed, I guess. But for myself, it was more about, okay, I can go sell some deals, I can hit indeed a number, but what's next?

Savan Kong

Mm-hmm.

David

Like for me it's a and this is kind of a gift and the curse 'cause I always want to know like well, what's the next thing? Like if I'm at point A and I wanna get to point B, once I land on point B, I'm like, all how do I get to point C? I'm not like enjoying I'm on point B, great. You know, it's like so it's a gift and a curse 'cause you're not really enjoying it but you're driven and so you're getting to the next next slot. And that was always what it was about for me when I went to amplitude. And at the time, like I say, I thought I was gonna start off like a partnerships arm there because we had done that at Optimizely and it was like a huge part of the business and I really believed in it. Kind of explored it for a while. Glad I didn't go that route. It's just not my thing. I'm more of a direct sales guy. But you know I I just kept my head down and was like, all right, well now I really want to figure out enterprise because that was the thing that was like holding me back at at Optimizely. Doesn't get talked about a lot. I actually only bring this up when candidates ask me or when I'm like talking to somebody that I'm interviewing with. But you'll look if you look at my profile, I actually had about a year and a half at Amplitude where I was a customer success manager. very, very different situation from what happened at Optimizer. I was actually doing quite well at Amplitude and sales at the time. but my mother had a nervous breakdown. I had to become her power of attorney.

Savan Kong

Mm-hmm.

David

And basically spent a bunch of time. she's an extreme porter. So I basically spent a bunch of time about six months cleaning up her house, renovating it, all this stuff, all in the weekends. So I asked our CRO at the time I was like, hey, can I, you know, move into a success role because I just won't be able to manage both you know, full-time sales role and a high growth startup, as well as all of this sort of like mom life stuff, right? And

Savan Kong

Yeah.

David

Best decision I ever made because ended up that we got it done. I actually got promoted in my first like seven months as a success manager there to like enterprise. and, you know, we now still have that house. It's a rental. We actually parlayed that into a a second home because we were able to pull a bunch of equity out of the house once we renovated it. and then as soon as I was done, I went right back into sales. And so

Savan Kong

Mm-hmm.

David

Yeah, a little bit of a blip on the radar there, but you know, I it had had to be done, basically. It was it was my mom, it was my family and was like a a high value situation. sorry took a step back in my career, ultimately did wonders for me, but at the time it didn't I was very uncertain. I didn't know what was gonna happen. So

Savan Kong

Yeah.

Savan Kong

Yeah. I want to talk about that a little bit because I you know I think we frame we frame these titles and promotions in a certain romanticized way, especially at startups, right? Especially when you're at a place that's exploding in growth and anytime something deviates from the traditional line that we may or may not have in our head about what success is. We feel like that's taking a step back or taking a step laterally in some way. and for you, you know, going into this role, which eventually you did very well at because you got promoted, is is, you know, a couple things. One, it's probably very it was very hard for you to stomach that and make that decision. Like there's some sort of process, I'm sure. That went into your head that said, okay, like this is the quote unquote sacrifices I need to make with my career in order to support my mom and all these things. and the the second part of that is, you know, I I I do wonder how you thought other people were gonna portray your move. And I'm sure there's a bunch of people that were surprised by it. But when you made that decision, what was going on in your head? Like how how did you process that move and then eventually how did you reconcile that you were okay with it, right? Like this is something that's gonna happen and this is the right thing for me at the right time.

David

Yeah. I mean, honestly with all of these transitions where on paper it might look like I'm taking a step back, there was never a question in my head if it was the right thing or not. I I just kind of knew. Especially in this scenario. for me, family always comes first. And you know, I don't have I'll say that I have a lot of great relationships that aren't necessarily blood family, but family.

Savan Kong

Right.

[50:00]

David

And for those people, I would do anything for them at any time. And especially my mother. And so it's like not even a question that I was gonna do this. It was just as soon as I got the permission and ability to transfer over, I just did it. internally I didn't say anything about that because I didn't want there to be this like, you just wanna come to success because whatever reason. It was just like, No, I'm interested in success now and like kinda just played it off like that. And so I felt bad 'cause for my manager at the time when I moved back into sales, he was like, why didn't you tell me? And I was kinda like, Well, this was always the plan and I didn't want to tell you that 'cause, you know, like and so he was taken a little off guard off guard for sure. But you know, it's just I knew I had to do it. There was never a question in my mind. I knew I'd give my opportunity again on the other side, whether it was with Amplitude or or another company. And

Savan Kong

Yeah.

David

Yeah, it just it just was. That makes sense.

Savan Kong

Yeah. What was it about amplitudes and and and startups for the people that are listening? You know, we've got a wide variety of different types of people that listen to to the show, and some of them have been in government their whole lives and some of them have been either enlisted their whole lives, but for for you and startups and tech specifically, like what is it about that environment that gets you motivated that gets you up in the morning and keeps you driven throughout the day. what does that look like for you?

David

Yeah, I so I've had a lot of conversations about this with my therapist, actually. She thinks because I grew up in a chaotic household, that I seek the chaos in my life and work. and I think there's definitely yeah, definitely something to that. but I think on the more sort of cerebral side of it, like I really love the figuring it out part.

Savan Kong

huh, yeah.

David

something about that just really like gets my brain going in a way that nothing else does. Like if I have to figure out a problem, I just get stuck on that for the most part until I figure it out or find a better way to do things. and startups are that's basically a startup in a nutshell of like every day you're doing that with five different things. and that's also why I've only ever done super, super early stage.

Savan Kong

Mm-hmm.

Savan Kong

Yeah.

Savan Kong

Yeah.

David

Like even at Amplitude when I left, they were about they're about like 80 million in in air when I left. So they're pretty, pretty far along. They went probably a year and a half after I I left, right? So they're pretty far along. and at that point, you know, I was gonna get into a manager role that got sort of I wasn't able to do that, basically I'll say. And then that's when I decided, you know, it's time for me to move on. I don't really want to do this rinse repeat thing of the playbook. but yeah, it's that.

Savan Kong

Mm-hmm.

David

Controlled chaos, constantly learning, constantly figuring things out.

Savan Kong

Yeah. Yeah. Yeah. David, I wanna fast forward a bunch of years and and talk about your startup and and how you chose to do this. You know, in the beginning of our conversation, we talked a little bit about you starting a family and also trying to start this business at the same time. tell me why this is the right time now for you.

David

Yeah, I I see it as there is no real right time. everybody tells me that that's had kids too. They're like, you can plan the perfect quote unquote time to have kids, but you just gotta do it. So I kind of see it the same way as the company. It's like it's something I've been thinking about since since Amplitude at least, like in terms of a tech company. I had a buddy of mine that was an engineer at Optimizely, and we had sort of

Savan Kong

Yeah.

David

talked about teaming up a couple of different times together, but never settled on a thing. And even before my last role at Mintlify, I was looking for a technical co-founder that had already started building a product that I could then partner up with him and or heard them and and you know, bring it to market and and all that stuff. I actually got offered a co-founder role, but I I declined it. And I only took Mintlify because it was the literal ideal scenario for me to take a full time role that wasn't co-founder role. I was the fifth higher, first non-technical hire. The company was doing really well at the time. I mean they were like a million in ARR, but there was some clear traction going on, gave me a lot of vibes, like optimizing amplitude. Turns out I made the right bet. We went from one to 10 in 18 months and they got, you know, a couple months after I left they took on 45 million from Andreessen Horowitz and got a 500 million dollar valuation.

Savan Kong

Yeah.

Savan Kong

Yeah.

David

But you know, I got fired from that job and it was very much a that one was very much a surprise. I had no idea that was coming. The optimizer thing was like, okay, yeah, I can see this coming, but this one was huge, huge surprise. And I just left sort of okay with it. I was like, this sucks. Like I was disappointed. But I was like, I know at this point in my career that I can do whatever the hell I want. And then that idea kind of just kept like

Savan Kong

Yeah.

Savan Kong

Right.

David

Growing my head because after I had like, like I said, gotten offer for co-founder role like a year and a prior and had all these other sort of interesting, super high-level conversations, I knew I could literally do whatever I wanted. And so I had to spend two months, three months really, cleaning my mom's house again. Kind of see a trend going on here. the hoarding the hoarding never stops. I won't get into that story right now, but basically it was required that I had to help her again. I had

Savan Kong

Yeah.

Savan Kong

Yeah.

David

So after we cleaned our first house out, I bought her a mobile home. She went and then filled that up over the next eight or whenever it was years. And it got really bad again. So, and we just did this like a couple of months ago. So I spent, you know, three months there with my my oldest brother and we yeah, we cleaned it out. And during this time, I'm like, What do I wanna do with my life? What do I want to do my career? Like, where do I wanna go? And you know, there's all sorts of options out there, but

Savan Kong

Right.

Savan Kong

Yeah, says fresh.

David

This like starting my own thing because I was like, well, if I go early stage again, I'm just ultimately going to be working for somebody doing the same work I just did with potentially the same outcome. And I was like, I really don't want that. I wanna, I wanna have more control. And so I was working alongside, you know, she had a lot of work that needed to be done. So the roof, this some parts of the ceiling, like with different contractors, painters, handymen, you name it, were coming through the house. I just started asking him, like, hey, like. What do you guys use for software? What do you guys use for apps? What problems do you deal with that you wish you didn't have to deal with? Like really basic, just sort of not even real research. I would just say it was just like conversational kind of stuff, just doing some discovery work. and that's what ultimately led me to like, I am gonna start my own company and it's gonna be doing this. That that was really the moment because I just couldn't keep myself, at least for now, working for somebody else. at this point in my career and

Savan Kong

Yeah.

David

And like what I've been able to accomplish. It just doesn't feel right, honestly. Like I would do it for the again, the perfect scenario for sure. But right now, you know, I'm not looking for that. It was more like I'm gonna go focus all my time on starting my own thing.

Savan Kong

David, do you feel like the firing at Mint LeFi sort of pushed you into this decision? and you know, call it fate, Jesus, God's plan, whatever you may call it. But you know, there's a there I see a series of things that's happened throughout your career that eventually led you to where you are now. and I wanna know. You know, if you were still at Mintlify, would you eventually have founded this company that you're doing now? and and if not, then you know what what it what would you still be trying to do? 'cause I feel like there's I'm trying to understand the psyche of where you are now and what what's motivating you. And it sounds like the freedom to be an entrepreneur is a big part of that. And the ability to control your own destiny is a big part of that. But what are some of these other things that sort of go into it?

David

When I was at Mentlify still, I was kicking around a totally different idea that applied directly to my job as a sales leader. And funny enough, two of our guys from Mentlify are now building that company and I'm probably gonna be advising them on it. but I decided that was just not the problem that I felt super passionate about solving and just sort of was

Savan Kong

Mm-hmm.

Savan Kong

Yeah. Yeah.

David

I'm always think like yes, my wife, I'm always thinking of ideas. I'm always thinking of and not just tech. Like I have this idea for a mug warmer. I have this idea for a hot tub. I have this idea for like random shit, you know? And it's just kinda my brain is just always going off on like on stuff like that. But I was just kinda waiting, honestly. So in a perfect world at the time, like back in November, if you would have asked me, I would still be at Mimify growing the sales team.

Savan Kong

yeah.

David

Like that's that's what I would be doing right now. if a you know, idea came along that I was super passionate about, I might pursue it. I might not. It's not it's really probably even less than fifty-fifty, honestly, at that point. but yeah, absolutely. Once once this happened, once I got let go, it's like it really accelerated my decision into to doing that. And you're you're absolutely right. It was a freedom. the I mean, I've always had this sort of entrepreneurial like spirit, if you will.

Savan Kong

Mm-hmm.

[01:00:14]

Savan Kong

Yeah.

David

But it was really the freedom, man. And you know, I I had consulted before too, right? I consulted for two years just working with early stage startups. And turns out you can make a pretty good living doing that. And you don't have to work that hard. But again, it wasn't a thing that excited me. I didn't own I wasn't owning anything. I wasn't like really I was contributing, but kind of not really. I don't know. It was just like a weird in-between space. And so I, you know, I'm doing that now actually, but just as like a way to pay the bills. and the startup, like the product.

Savan Kong

Mm-hmm. That's a

David

building, the company building part for me is the part that's like, all right, let's go. Let's do this.

Savan Kong

Yeah. Yeah. What what scares you the most right now about where you're at in life with the family and the startup and all those things that you've got that are unknowns?

David

my God. You know, I I saw when you talked about this podcast and sort of the I don't want to call it the ugly side of things, but the the parts that people don't really talk about a lot, I think it's super important and it's hard to do and it's hard to listen to, honestly. But it's just it's reality, you know, it's what's happening. And I I think for me, the thing that scares me the most is failure. Like I don't want to fail. I'm taking a huge risk. I'm taking a huge bet on myself. and I can have all the conviction in the world, I can have all the drive in the world, I can make all the right decisions and still fail. And most companies fail, right? Like 99.9% of companies fail, like spec tech startups do. And so you think about that and you're like, Well, what the hell am I doing? Like, why am I doing am I the right person? And like, have I been sleeping well? I'm like already getting what do you call imposter syndrome and like

Savan Kong

Yeah.

Savan Kong

Yep.

David

All these things. But then I just tell myself, man, like every time in my career that I've just bet and doubled down on myself, I've seen the dividends, I've seen the ROI, it's paid me back tenfold. And if I don't do this now, like I'll probably never do it, or I'll do it like way later on in a much sort of less involved way.

Savan Kong

Yes. Yep.

David

'Cause kids are like I say, family is important to me and I've really, really, really have always wanted to have kids my entire life. Being the youngest of five, like I said, just just something in my head I've always gonna have like two or three kids and starting a little later in life, right? Like later than I would have liked. But like I said, there's not really a perfect time for these things. You just kinda go for it. So yeah, I'm scared of failing. I'm scared of of not being able to provide. Like, you know, I've

Savan Kong

Yeah, yeah.

David

Done well, it was five years at Amplitude. We had the whole going public thing and I have a financial advisor, you know, I have some investment properties and and whatnot. So I'm I'm good. But when you grow up with not that stuff, you really wanna hold on to it. You don't wanna you don't wanna even risk or talk about or think about losing it or or decreasing it. So I'm still fighting with that, honestly, like every day. But at the same time, like you say, like

Savan Kong

Yeah.

David

I can't think of any other better investment than in myself. So

Savan Kong

Yeah. I mean, I don't know about you, but like for me the that fear of failure is I think less about myself and more about like letting other people down, right? That have like genuinely made investments in you or your career or your education, whether that's your wife who's sticking by you when you're not making any money and it looks like you're spinning in circles or your parents Or your friends, 'cause you can't go out with them anymore, 'cause you're still working on something. Like that to me is the thing that scares me the most. And how how how are you sort of like coping with that and getting over that?

David

You're seeing it, man, real, real time. I don't know. No, I mean, I was just talking to my my co-founder about this because he'd been working on something for a year and he was like, I'm starting to lose confidence. I'm starting to, I need momentum, I need some wins, you know? Like I can't keep just pounding my head against the wall, like this just doesn't work. and we're talking about fundraising and initially I had this like bright eyed version of like, I'm gonna bootstrap for a number of years and then when when we're

Savan Kong

Yeah.

David

Ready to do it, we'll we'll raise. And a lot of that honestly had to do with, like, say, not disappointing people. Like if somebody's gonna write me a check, like I want them to get all their money and then some on that check because they're investing in me. They believe in me, you know. And well, my co-founder, they believe in us. Like, and I don't want to do that blindly. Like you see all these companies that are like, I have this concept that isn't a problem yet, and we don't even have a a prototype for it. And they're like, Here's ten million dollars, and you're like,

Savan Kong

Yeah.

David

Why? Like what is I don't understand that, right? so I do think there's an in between of those things. Like you don't have to go all the way to the extreme of one or the other. And we came to that conclusion and we're like, okay, yes, we can do this. And so just honestly every day I'm just sort of figuring the next thing out. Like the the fundraising was one, the conviction of like where we want to focus is the current sort of problem that we're working through. at some point you just gotta stick your flag in the ground and go.

Savan Kong

Mm-hmm.

David

And like you're not gonna be right. Like no matter which direction you pick, you're not gonna be a hundred percent correct. You're gonna have to find your way through it and figure it out, right? Like like I've said my whole life, my whole career. and so you know, it's it's tough when you're in that uncertainty and it's all uncertain. There's zero certainty. Like at least in a million ARR startup, there's some there's some certainty, right? This is like we don't even there's zero certainty. So it's it's tough, it's hard.

Savan Kong

ja

Savan Kong

Yeah, something. Yeah. what what what are some of the things like let's just fast forward a few years, let's just say like a year or two, what are some of the things that you have in your head that would be success metrics for for your business? Like, you know, what are some of the things that you're you're looking forward to that you're driving towards?

David

My philosophy on success on a successful business is building a lasting company, meaning a company that's around for more than you know five, six, seven years and provides like value to real people and that they pay a fair price for. So if in a couple of years we're starting down that road, meaning

Savan Kong

Mm-hmm. Mm-hmm.

David

We have product out there that at least a handful or a couple hundred or a couple thousand, whatever it is, people love. and they're paying a fair price for. And the whole reason why I chose the services and trades industry is because I firmly believe that's going to be a lasting industry for the foreseeable future. meaning AI is not going to take over those jobs anytime soon. that would be a success to me. And it like whether it's a hundred thousand dollar company or a hundred million dollar company. I don't really have a number on that. Obviously the more the better, I guess. But I my whole thing is like I want to do it in a way that is like morally aligned with how I think and operate. Meaning I don't want to just grow at all costs. I don't want to just like fire people for whatever random reasons. I don't want to, you know, do do the quote unquote wrong thing. Do it the wrong way. And if I can do that

Savan Kong

Yeah.

David

mostly at least. And I know there's gonna be a lot of challenges with that, but if I can do that mostly and also accomplish those other things about, you know, product that people love and pay for, like I think that would be super successful in the next few years for myself.

Savan Kong

David, last two questions, my friend. first one is do you are you at a point in your business where you want to give an elevator pitch about it on the show?

David

Yeah, sure. We're still noodling on the name. right now we're at work true. So we're building we're building AI essentially for the services and trades industries. You can think about HVAC, plumbing, painters, contractors, that kind of handyman, that kind of thing. Like I was saying to folks that I was working with. My brother is a handyman. he was previously in retail and restaurants for them for the bulk of his career. And he struggled. He was trying to figure out how to find leads. And once he got customers, how to get them to pay him on time and if they needed an invoice, what to do, or if he wanted a referral, or like, you know, basically just market himself in any kind of way. He didn't know how to do any of that stuff. And even three years in, he's you know, he he took two months off with me to go help fix our mom's house and he was like, Well, I need to go find clients again. Like, you know, how what do I do here? Like And I just kind of saw him struggling. He's a great guy. He works super hard. He has a lot of regulars. And it wasn't a matter of like him being able to do the job. It was just like, how does he figure it out? Like in a quick enough way that he can support himself and then grow and sustain that. and so that's really what I'm building for is that that solo operator, that small team where they really want to be successful. They just don't necessarily have the tools to do it or they don't know how to string all the different tools together. so we want to be a one-stop shop for everything from responding to leads, whether that's with like voice agents and voice AI, text message, you know, kind of agentic follow-up, scheduling, all the way through invoicing and payments, getting reviews for your business, that kind of thing. so right now we're in a prototype stage. We're just collecting feedback. If anybody wants to take a look or take our two minute survey, we we'd love to hear from you.

Savan Kong

Mm-hmm.

[01:10:12]

Savan Kong

Yeah. Yeah, we'll I'll I'll get a link from you to some form that you want to promote. We'll put it in the description and in the newsletter. So if you're in that trade space, definitely fill out that form. all right, David, last question. And I typically ask this of people that have families or want to have families, but you know, we're gonna fast forward about thirty years and your kids are listening to this show. What do you hope they take away from our conversation today?

David

just keep trying. Just keep going. Like it doesn't matter if it's work, if it's your mental health, if it's your physical health, just keep going. Like there's nothing better than just the belief in the momentum. Because you keep doing that and it compounds day every day. And the next thing you know, you're in an amazing spot. Again, whether it's career-wise or mental health or physical health or whatever, whatever it is in your life, just keep going. The second thing I would say is always bet on yourself. Always, always, always bet on yourself. something that if I were to go back to my younger self and tell, you know, give them one piece of advice, it would be that, honestly. Do it even more. Like you think you're taking a big bet, take an even bigger one. Like, because it's gonna work out. And if it doesn't work out,

Savan Kong

Mm.

Savan Kong

Mm-hmm.

David

Keep going, keep moving forward and you're gonna figure it out. it's just while you're in it, it's really hard, but if you truly stick to that, you'll have great results.

Savan Kong

Yeah.

Savan Kong

I love that dude. That's a perfect way to end the show, my man. David, I want to thank you for coming on. I appreciate your friendship over the years and I wish you and this new business all the success in the world.

David

You too better.

David

Thank you, sir. Appreciate you, my friend.

Savan Kong

All right, we'll talk soon. Peace.

David

Yeah let it.

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