An Interview with Liz Raad on Her Journey into Startup Life
10,000 for a goatee.
Speaker 2:No. No. I'll take that money and I'll go stay at a hotel while I wait for it to grow back.
Speaker 1:Is that bad for you?
Speaker 2:It's like a different person. It's like like a stranger man in my house.
Speaker 1:A stranger man. But today we have a a guest. And our guest today is Liz Rad, who I'm married to, but more importantly, she is a founder and has been in tech for a while. And unlike most of the people we talk to, she's not an engineer, so she does everything else besides that. And she listened to the podcast that the episode me and Adam had about being a founder?
Speaker 2:The startup one.
Speaker 1:The startup one. Right.
Speaker 2:Yeah.
Speaker 1:And she said, it was pretty good, but you guys didn't talk about any of the good stuff. So I was like, okay. Then you come on and you talk about the good stuff. Just so everyone has a little bit of context, give us a little bit of background on yourself and, like, how you got into tech and
Speaker 2:So I'm not an engineer, but I'm also not originally a tech person or a startup person or a business person. I wanted to be a therapist. I wanted to be a psychologist, I think because I just wanted therapy. So I studied that in college. And then I ended up kind of working in a couple of research labs because everybody was like, well, if you want to be a therapist, you need research experience, you need research experience, whatever.
Speaker 2:So I did that and ended up liking that a lot more. So for a while there, I was like, I wanna be a researcher. And I did that for enough time, it'd be like four or five years, where it was very clear, no, I do not want to be a researcher. I definitely do not want this. But at that point, it was pretty hard because I had gone, like, so far down that path, and I was so set up to, like, keep going and be in that world.
Speaker 2:And I really didn't have, like I thought I didn't have any other skills or experience. And I didn't even know people in other industries. I didn't even know what a startup was. Like, stuff like did not exist in my world. But I had one friend who like pointed out like, Hey, like a lot of the stuff that you like, there's this thing called like a startup and like, you might be a really good fit for it.
Speaker 2:So I just started learning a little bit about that, talking to whoever I could talk and then I, whoever I could talk to. And then I convinced myself that I could do it, that I could like fully pivot my career. And I did, but it was really hard and it took a really long time. And I ended up moving from Miami to New York and trying to find a job and I couldn't. And so then I had to keep being in the it was like a whole situation.
Speaker 1:Yeah. So I think one of the things that's interesting is you had to discover that tech existed and that startups existed. It's a little different for myself because my family is in that like my my dad's a software engineer so I kinda grew up knowing about all that. So that's very weird for me to hear like, how could you not know existed because it's like, was so in my face all the time. Mhmm.
Speaker 1:So when you were growing up, like, what, like, what did you perceive the world as? Like, did you not even know that was a thing? Like, what was it what are the options for your career?
Speaker 2:Didn't even know that a software engineer was a thing. Don't even get me started on like a product manager or a designer. Like, didn't this was also like, I think a little bit earlier. Like, I know this world already existed in like 2011 to 2015, but I think now it's like definitely everywhere. And before it like, it hadn't hit Miami yet.
Speaker 2:So to me, the world was like doctors and lawyers and small business owners, and that's it. And then I discovered academia and I was like, oh, I didn't know this existed. So it was pretty small. You mentioned like your family. So my family, all small business owners, all immigrant small business owners.
Speaker 2:And later in my life, came to realize like how important that has been for my psychology and the way I see the world. I didn't really appreciate it at first, but I think we've talked about how now I appreciate like, oh yeah, like I'm comfortable with responsibility. Like, I feel weird filling out a time sheet, you know, things like that.
Speaker 1:So if your family is all small business owners, do they Is it one of those things where they didn't want you exactly Like, what were their hopes you? Like, did they want you to also be a small business owner or do they want you to get like a professional job? Because they kind of saw that as like the next level.
Speaker 2:It was very important to them that I get like an education, like getting into college, getting a college degree, that stuff was really important to them. My dad kind of said he like wanted me to take over the family business, but you know how he is. I think he was just kind of like playing the character of someone who wants their daughter to join. I don't think he like really wanted that. And then I think that they wanted me to be like a professional with a title and with job security and haven't given me too much of a hard time, but we're not into the idea of I'm gonna switch careers.
Speaker 2:I'm gonna quit my job. I'm gonna move to a new city. We're not into the idea of I'm gonna start my own business. Mhmm. Even even though that's what they did.
Speaker 2:But once the ball got rolling, I think they get it.
Speaker 1:Yeah. So once you did decide to, like, switch careers, I think in at least in, like, you know, the the things that we generally talk about, we talk a lot about engineers or people that are new to engineering, trying to get their first job, how to bring in the tech. And that's discussed to death, I think. And, there's a lot of challenges with that. But I imagine do you think it's even harder as, like, a non engineer to get into tech?
Speaker 1:Like, what was that process like?
Speaker 2:I wouldn't know how to compare, but it was really hard, but not impossible. And I think there's two things I took away from it. So one, like you always have something. Like you always have a way to like fit yourself into whatever the new thing is that you want, even though it's not startups or tech. So for me, I like looked at the experiences I'd had and I found a way to like kind of shape it into a narrative that made sense for why I wanna be at a startup.
Speaker 2:So like the lab that I worked in was brand new. The professor I had worked for had just moved down to the university where I was, and we had to set everything up from scratch. So it was like me and another professor and him for a really long time. So it's kind of like a startup where I'm like the third employee. And I had to set everything up by myself.
Speaker 2:And we grew the lab from just me to like 20 to 30 people. And I was involved in all of that. And so if I tell you the story in that way, all of a sudden it seems like really, really relevant. So that's one thing you can always just kind of understand like this new industry you're trying to go into and find ways of like seeing your own story in a way that fits. Another thing is I was kind of constrained and, you know, maybe this is something people should think about and maybe it's okay for that first, move into the industry.
Speaker 2:So I really couldn't make progress in anything that wasn't healthcare related or psychology related, because it needed to kind of fit in that way. Like I just, I tried, I tried, and I really only clicked with startups that were doing something related to healthcare and that valued that. And that was a constraint. It was also, you know, fine by me. And the other constraint was I couldn't just like get whatever job I wanted at a startup.
Speaker 2:And that helped, I was clear on that, right? I was like, I just need to get into a startup. That's all I need to do. I don't have to have like the perfect job. I don't need to have a cool job.
Speaker 2:So when I joined Bright Health, which is where I met you, and that was my first startup, I just did customer support. And then I worked my way into where I am today. And I can talk about that too, but.
Speaker 1:Yeah, I mean, I could tell a little bit of that from my side. So I met Liz at a startup, as a company there. It was just me and one other person to start. And we started after the first like, maybe like ten months or so. Think it was still under a year we started hiring more people.
Speaker 1:It was a company that did transportation for medical situations, like non emergency transportation. People needed to get to their chemo appointments and they get to surgery, they didn't have access to transportation. The hospital would pay for it, but it would be fulfilled by like Uber or like something that was not an emergency. And we did have a pretty heavy support burden because we were transporting, older people, people that are like less adept with technology. So there are always things going wrong or like slightly wrong with the rides.
Speaker 1:People call in and we had, I guess, support burden. So as we scaled, we needed to have more customer support people. So that's all we were hiring for. We were just hiring for, two more support people. And Liz was one of the people that interviewed for it.
Speaker 1:We decided to hire her. I was pretty excited because she came across really competent. It definitely in hindsight, like, I think it was clear that she would have always outgrown that role. But we did hire her and then when she came in, that was like her foot in the door and it was clear that she was just using the support role to get what she actually wanted, which was like a bigger role at the company.
Speaker 2:And that was also the day we met, the day of my interview. Yeah. And I also almost didn't take the initial phone call with the founder. It was like a very because the way he reached out was kinda weird, and I was a little weirded out. And so it was like a very, very last minute decision to, like, pick up the phone.
Speaker 2:And Dax hates this. Like,
Speaker 1:hates this. Okay. But let let me explain. So Liz is, like, playing it down a little bit, but, our founder was really weird. Really, really weird dude.
Speaker 1:And most people could tell right away when they spoke to him. So I think that's what happened. Right? You were kinda weirded out?
Speaker 2:Yeah. I got, in the psychology world, you call it the axis two tingle. I got the axis two tingle.
Speaker 1:And what is axis two tingle?
Speaker 2:It's
Speaker 1:You can't just say and not explain it. Know?
Speaker 2:Alright. Fair. It's a weird it's kinda like if you know you know kind of thing. It's a weird feeling you get when you're around somebody who probably has a personality disorder. In the diagnostic thing, access to is like a personality disorder.
Speaker 2:So we, we call it the access to dingle in the field.
Speaker 1:So Liz got that and almost, she almost didn't take the call, and then I would have never met in my whole life as it is now, which I love, wouldn't exist. So I I always freak out when I when I think about how small of a choice. You would've just blown it off for no reason. Like, you probably were just, like, being lazy.
Speaker 2:I would yeah. I was running late, because I'm always running late to everything, but I I also feel embarrassed about running late. And so I was like, I I I'd rather just bail on the call than show up to call late.
Speaker 1:Yeah. So lesson of the story, don't bail on stuff. It could literally ruin So a great stop bailing everyone. Yeah. I'm like annoyed at you somehow for this.
Speaker 2:I know.
Speaker 1:I'm annoyed that you're someone that is late to things and potentially almost ruined my life because of that.
Speaker 2:Alright. Okay.
Speaker 1:Yeah. So you were saying, you got so what was like so you finally got a job in tech. Again, not the role. It was just it was a customer support role, so not the role you were looking for. But, yeah, how'd you take it from there?
Speaker 2:Yeah. And then just going back a little bit, the last like piece of advice that I would give is you can like read about the industry you wanna go into and research it a little bit and understand it. Not because you're really going to understand it until you're in it, but just so you have like at least a common language that you're speaking going into it. And I think that really helped a lot. I think it was those three things coming together that helped me actually make the pivot.
Speaker 2:But yeah, once I was in Ride Health doing customer support, these things were just very like instinctive and like very clear to me. Like very clear to me, like I didn't join this five person startup where I'm getting paid nothing to do customer support. Like, it's very, very obvious. Very obvious that it was a situation where a control freak just needed to take control and, like, fix a bunch of stuff and set up a bunch of stuff. And if you did that, you become indispensable and you get a lot of options.
Speaker 2:And so I just got to work on that immediately. Like I would do my customer support stuff, but I would be setting everything up so that, you know, I was creating systems that other people could use, started working with you immediately and discovered product management, which was awesome. It was so fun. It was very like very pure, right? It was like, I would get a customer support thing and like you deal with it, but the way to actually fix it is to like change something about the product.
Speaker 2:And so then I started working with you on some product specs. I didn't know what I was doing was called product spec because I didn't know what a product spec was, but that's what it ended up being. I impressed you with a flowchart. Do remember that?
Speaker 1:Yes. I do remember that. I I well, I think I technically showed you the tool. Right? It was whimsical.
Speaker 2:Whimsical. You did. And I love whimsical now. Yeah.
Speaker 1:Yeah. So we were getting a lot of this complex support cases and Liz was handling them all. So she came back to us with, you know, this tool whimsical that lets you diagram like flow charts and things like that. She came back to us with an idea for an automated system that could like that can handle some of these complex flows and, yeah, like I remember thinking like, wow, this is like really well thought through. It like handles all the edge cases and the places where we can't handle it like nicely ejects.
Speaker 1:It's not too annoying for the user. So yeah, I think I remember thinking, you know, like really good instincts and and thought through this really thoroughly. And again, from our point of view, we had just hired a customer support person to answer the phones. We didn't really expect this level like this. So no one told you to do that.
Speaker 1:No one asked you to do it. It was something that kinda you just saw and grabbed.
Speaker 2:Right. Because I had like a master plan. Like, little did you know I had I had just, like, snuck my way in, and I had, like, a plan for what I was gonna do there. And if I'm being, like, totally honest, I don't see any other reason to ever join a startup. Like I do not, I don't get it.
Speaker 2:Like I don't understand why you would just like go join, especially a very because we say startup, but like, I'm not talking about like a 100 person series. I'm talking about like, there's five people, there's 10 people. I don't get why you would ever do that to yourself unless it's because you're gonna take advantage of it in this way. You wanna pivot careers, you're very early on and you wanna get a ton of responsibility, which I think you've pointed out, Dax, or you want, like, you're really gonna like get something out of it and you're not going into it expecting that anybody is gonna tell you what to do. Like that's the opportunity.
Speaker 2:The opportunity is no one's gonna tell you what to do and you go and figure it out. And all of a sudden you're like the most indispensable person in the company. And you work your way into whatever job title you want. And then your next job is that career that you've basically chosen for yourself. If you're not gonna do that, like don't, I don't know what you're doing at it.
Speaker 2:Don't go to a startup because also you're gonna annoy people like me, right? Because you're gonna be like, oh, like what do I do? Like, where's the docs? And I'm gonna be like, why are you here? So just only go into a startup if that's how you're gonna approach it is my hot take.
Speaker 1:It's, it's such a huge opportunity to lever up. Like, so you literally had no experience in tech. And after that job, you were set up to basically get any role you wanted.
Speaker 2:Yeah. So hold on. I I do think it's really funny. So I entered doing customer support and I exited as head of pro
Speaker 1:Yeah. Exactly. Yeah. So it's just like the opportunity is so there because when things are early, there's just so much it's like a land grab. It's like the startup itself is trying to be early to something and grab a bunch of land.
Speaker 1:But similar to like internally that applies as well. Like you can go and grab stuff because no one has grabbed it yet. And the way I always phrase it because I find it funny is, the whole thing with startups is when you're trying to get a job there, you're trying to trick someone to giving you more responsibility than you should have. And you probably don't know how to do half of it but you're gonna someone's gonna pay you, maybe not a lot, but you're gonna get paid something to do to do that. And then once you've done it once, you have that experience forever and that's how you, like, launch your career.
Speaker 1:I think this path is like a fantastic path and I think it gets you really really really far ahead compared to some traditional paths. Like even if you look at, let's say someone that, you know, knew they're gonna go into tech, you know, went to school for for x amount of years and and got like an entry level position already at an established company, you can only go up so fast. Like the best person maybe is gonna move up like 20% faster than like the average person. But when you join a startup, you can like skip four or five years of your career if you do take advantage of like, you know, working really hard and being able to operate on your own without someone telling you what to do.
Speaker 2:Yeah, I think that's the key thing. I mean, everybody works hard and everybody suffers, but it's like the part where you're okay with taking responsibility and you're okay with, like, the ambiguity of like, what do I do? What do I work on? I think that's the key part.
Speaker 1:Yeah. So, yeah, so what happened after you left that first role? Was you were there for like two and a half years? Something like that?
Speaker 2:So I was at Ride Health, first startup, started customer support, did like a bunch of stuff in between and eventually ended up in a head of product role. So I was head of product expert as head of engineering, and then we started dating. That surprise now when. But after I left Ride Health, yeah, I joined this other company and this was like March 2020, March, April 2020. So the pandemic had just hit, everybody was working from home.
Speaker 2:And then these like digital healthcare startups were like, all the rage, like the hims and hers and the row. And like, everybody was like taking some thing in medicine and like creating a startup around it. And I went to one of these places that was focused on psychiatry. And it's kind of embarrassing to like say that now and to talk about it because there's so much, like at this point, there's like so much negative press with that. Like, everybody thinks cerebral and it's, that was a disaster and it's like so embarrassing.
Speaker 2:To be honest, like a lot of the shady things that are in the news are like kind of right when it comes to this space. So I did not enjoy my time there at all for like so many different reasons, but I got the idea for my current company, which is great. So I think I ended up being there for maybe like less than a year.
Speaker 1:Was it really less than a year? Oh my God, that felt like forever.
Speaker 2:Yeah. So my role there was so, okay, just picture like an online psychiatry practice. So just like a regular doctor's practice, but instead of in person, it's online. So you have your patients and they wanted to create a product that the patients could use, but you also have like doctors and nurses and admin, and you need a product that they can use to actually see the patients and provide the treatment. And that was the product that I was in charge of.
Speaker 2:And what I learned is that, first of all, that product, matter how small and minimal you're trying to keep it is a beast. So if that's not the focus of your company, you should never build that. But second, there's no good options in the market. So I'm like really no good options. Like this category of software is horrid.
Speaker 2:So I understand why people end up building their own thing. It's because what's in the market is like so crappy. And so I thought this was a great opportunity because I'm an idiot and I didn't realize how hard it was gonna be. But, yeah, that was the idea for Boomi.
Speaker 1:So I mean, we can talk about this a little bit. So it's build versus buy thing. It comes up, across, I mean, any business and engineers sort of think about this, non engineers would think about it as well. So in that case, the thought process was you guys did try to buy something. Right?
Speaker 1:You guys went and evaluated everything that was out there?
Speaker 2:We actually did what most people do, which is we did a combi we took a combination approach. So we took some things off the shelf and then we created our own tooling on top of that to just kinda like compensate for the things that we needed that it didn't have. So what most people actually do is they'll buy a bunch of different things and they'll glue them together And or they will also build their own little tool to compensate for like all the issues that the tools that they bought have. So it's sort of this like hodgepodge approach. We just glue stuff together.
Speaker 1:Yeah. And did that work well? No. And why not?
Speaker 2:Well, because when you glue a bunch of stuff together, you're just you're never gonna get a good outcome. Like, we love APIs. We love integrations. But when it comes to a tool like this, that's running your business, it's your operations tool. It's like how everything runs and works.
Speaker 2:It's just that there's always gonna be like something stupid, like a date of birth got updated in this tool, but not in this tool. Now you're working with two different types of information. There's always gonna be reporting is a nightmare. I think we've talked about this, but the people who end up doing the reporting are the ones that know exactly how much this doesn't work because everything is gonna end up showing up in the reporting as like, why do I have like five instances of this patient? Like, why does this look so weird?
Speaker 2:Like, why did this weird thing happen? Like, you know, all the ways that people are compensating for the shortcomings of the tool, if you do the reporting. So it's just for a tool like this, for the thing that operates your business, that runs your business, you need something that's greater than the sum of its parts. You can't just be like, well, I need to schedule something. So I'm going to use this scheduling tool and I need to take some notes.
Speaker 2:So I'm going to use this charting tool and I'm going to glue them together. Cause now I have the capabilities of scheduling and of charting. Like, yeah, you have the capabilities of scheduling and of charting, but when it comes to like a nice workflow and like clean operations, you need something where it's greater than the sum of its parts. Like when something happens with scheduling, like this other thing happens and it all kind of flows nicely. So that's just like the beginning of why I think that doesn't work.
Speaker 1:Yeah. And then going back to the company a little bit more. So I think you you, like, said it a little bit politely, but I'll, like, recall from my memory, Liz's entire time there was a disaster. I remember just every week, there was just, like, some other thing going wrong and just kind of all all unforced errors. Like, it wasn't like, the business was getting hit by a bunch of externally, just internally, it just could like, you know, were just a lot things have gone wrong.
Speaker 1:And it got to the point where it was it was, like, bothering me. Like, I was spending my time thinking about it, being like, that's so stupid, like they should do it like this and I was getting frustrated and I like, I got to the point where I was like, I wanna go talk to people there and tell them what to do. So yeah, it like, you know, months and months of this just was not working well and I think at some point I was just like, why are you doing this? Like, what are we what are we like getting out of it? I'm gonna spend a you know, you can spend a couple years here.
Speaker 1:Even if it's successful, if all this like pain is is worth it and it produces something successful, it's not gonna be like a life changing amount of money or anything. Maybe you get set up for like a better role next. So I do think I remember me saying that you should go try to start your own thing. Right? Is that how you remember it?
Speaker 2:Mhmm. Yep. It was your idea. Yeah. I remember you and I
Speaker 1:because I was so annoyed by it. Was like, we need to find a way out of this situation.
Speaker 2:Get out of this. Yeah. We're at Dinosaur Barbecue in Brooklyn.
Speaker 1:Oh, yeah. So how was that, like, how was that thought process of deciding to leave and and start your own thing?
Speaker 2:I kind of felt like I definitely wanted to leave because the company was a disaster and it was a whole thing. But, yeah, I definitely wanted to leave and I just couldn't think of what the next thing would be. Like, I couldn't imagine, like, what company I was gonna work for next and what role I was gonna have next because anything I could think of kind of felt like just going around in circles, like just doing the same thing all over again. And I think when you get to that point, like that's probably a pretty good signal to go and start your own thing, especially if that's something that you've always wanted to do because yeah, any other job I went and got like, it wouldn't just been the same thing as before. And, know, we had a good idea with Boomi.
Speaker 2:We weren't like really grasping for ideas. Although I remember at the time we were exploring a couple of different things, I forget now. We were thinking about like a finding a therapist type business or tool or something like that. But yeah, I got really excited about Boomi. I think that ultimately, like I am an operations person.
Speaker 2:That's how I think. That's what I like. But because it's the year 2023, I'm an operations person with access to an engineer. And so the way that I express all of that is, like, through products that support the operations of the business. So the type of product that Boomi is, was like a really good fit for that.
Speaker 2:And it's like one of the hardest products you could choose. And I like kinda knew that, but I was like ignoring it. And now I really understand that. So it's been just massively painful, but also really fun because selfishly, like, I like thinking about these problems and like, I like working through this stuff and like, I find it really fun. Sometimes I feel a little guilty, like, oh, maybe I should have like, because this is like my business and my livelihood and I should have picked something that was easier and more straightforward, but I'm like enjoying how hard it is.
Speaker 2:So I feel a little weird about that, but yeah, I mean, it's like a massive product, it's vertical SaaS. So you have to build like all the features and it's in healthcare, which is one of the most highly regulated industries. And, that's just the beginning of what makes it hard.
Speaker 1:Yeah. But the good side of that is if you and that's what I tell people all the time, like, I think a lot of advice gets mixed up together and applied the wrong way. You do need to build simple products. You need to, like, start small and grow and, like, learn and and do all that. But think people conflate that with just picking, a very simple ambition.
Speaker 1:So I think with this, it's like a very ambitious product, very difficult. The upside the downside of that is like very hard and it takes a long time and and it's pain can be painful. But the upside is like, you're really not gonna run into a competitor. Like, who is willing whatever pain you had to go through, someone else has to go through as well. And at the end of that, like you can sit on, like, let's say it took you like two or three years to get it to a place where it's usable.
Speaker 1:Someone else more or less has to go through that same pain. So yeah, it's hard to create things of value. Well, something is valuable because like a lot of input went into it. If something could be built in one month, you know, it has one month of value behind it. So yeah, I generally don't mind stuff being really hard and I think I've changed my mind on this over time.
Speaker 1:Think I definitely initially was like, I would kind of see like these simple little tools that make money and I would think like that's what I should be doing, I should be making like 10 of those. But there are people that find success with that but motivation is a big thing and if you're trying to if you're going for something way way way more ambitious like, it's just a lot more fun to work on much much bigger problems. And even at SST, like we're always thinking about like how there's like a current market we're focused on but like, what's the next one? What's the next one? Like, what's the craziest version of of what this all could look like?
Speaker 1:And that excitement I think is is helpful in in keeping you motivated.
Speaker 2:Yeah. So let's talk about this for a little bit because there's an interesting like me and you dynamic here. So we were talking about this the other night, but I'm somebody that I can only do something if it's gonna be like the best and the most exciting and the most challenging to the point where you can like make fun of me for being like extremely delusional about where I think Boomi is gonna go. And we talked about it for the first time the other night, and you were like, no. Like, I never thought that that's where that would go.
Speaker 2:And I'm like, yeah. No. Like, we'll replace the Salesforce tower. Like, that'll be like but it's important for me because if I don't think that way, like, I'm not gonna do it. Like we joke about this, but this is the way I am with like preparing dinner.
Speaker 2:Like your approach has been like, Liz, just make it simple so that you can do it more consistently, like just this and that. And then I've tried that. And I'm like, I just don't wanna do it if it's not gonna be like really great and perfect and delicious and beautiful and like, and it take a little bit of time. So I need that to be motivated. I need that to do things.
Speaker 2:Like need it to be like the highest version of itself or whatever. But I felt bad about that for a long time because I was like, what if, you know, I wanna do this grand thing and then trying to do the grand thing, like I totally flop and we could have been spending our time on something more straightforward that would like make us more money and all of that. And yeah, think you've kind of come around to this way of thinking a little bit more, but I used to think that the ideas you had around just think like a little simple tool and make a ton of money off of it. I used to think that I used to feel bad about not taking that approach basically.
Speaker 1:Yeah. I think the thing you described, I've said this to you before, like I'm definitely a founder persona, but I think you are even more so a founder persona, specifically for the thing that you described. I kinda had
Speaker 2:to I like learn delusional.
Speaker 1:Yeah. Yeah. But it's it's important. It's like an important trait and I I feel like for me, I kinda had to learn it and I realized at some point, I was kind of artificially capping my ambition because at some somewhere in the back of my head I was like, the thought was something like, who am I to be the one that does something like that? Like, kind of overly practical to the point of like, maybe being cynical or like pessimistic.
Speaker 1:And I think over time, I just started to realize like, even the people who done like the craziest things, they're actually not that different. Like, of course, like I'm not gonna, you know, be like a crazy NBA player, right? Like there's just like, some people are like truly gifted and special. But for a lot of the things that are within my realm of, like, in my space and kind of stuff that I could do, a lot of people are working on stuff are just normal and they just kind of decided to do it. So I think it took me a while to think more that way and I think I've landed somewhere in the middle.
Speaker 1:You much more naturally think that way.
Speaker 2:Yeah. And I also feel like, who am I to think that I can do that? And I find I find this trait that I have, like, really embarrassing. Like, it's embarrassing, right? Because if you don't get there, then it's like, yeah, like, of course, you didn't get there.
Speaker 2:Like, I can't believe you thought you were gonna get there in the first place. But I'm feeling more comfortable, like, saying it out loud. Like, there was a time where I would never share this with anybody, like, not even you. I would just silently be like, I think it's gonna, like, work out for me. Like, I think I'm gonna, like I think I'm gonna replace Salesforce.
Speaker 2:So I both have this, delusion and then this self consciousness and I don't know, just the way it is.
Speaker 1:Yeah. Yeah. So I mean, I've talked about this before, but obviously when you are a founder, some days you wake up crazy motivated, some days you wake wake up think you're doing everything wrong. So we were in a phase where we were working on like this pretty complicated table. It's like, you know, filtering, sorting, all that stuff, grouping, views, all that.
Speaker 1:And it was already pretty complicated despite being MVP and I was like, can this really be sometimes you like, step back and you get a sense of like, I'm working on a table. Like, how is this the thing that's gonna get us to like, all these crazy dreams and everything? And I just couldn't see it. I just couldn't see how, like, continuing on this path, like, gets to the place where we needed to go. But yeah, I think that was that was my head was at.
Speaker 2:Yeah. And then the interesting thing is that you came to me and we both I was also feeling it. Like I was also feeling like a lack of motivation and some insecurity around that. And so when you brought it to me, was like, my insecurity is like, correct. Like, I don't know what I'm doing.
Speaker 2:And I don't know if this is the right thing to work on. And what if like we are putting in all this effort building stupid table and that, amounts to nothing? Like, I was feeling the same things that you were feeling. And so when you brought it to me, it was like a confirmation. And I was like, oh, no.
Speaker 2:And then I think it's interesting that we took it to a place where we just immediately started like fantasizing, fantasizing and negotiating, right? It was like our brain needed to like find an escape hatch from this thing that we were stuck on. And we started fantasizing about like little products that we could build and like things we could turn Boomi into so that it wasn't Boomi anymore. We were just fantasizing about ways to give up. And it kind of made us feel better because it made us feel like we had an escape route.
Speaker 2:And, but they didn't feel good. Like I knew it was wrong. It just didn't feel good. And then I think I took a step back and I literally Googled, I literally Googled like how to not give up.
Speaker 1:Is that how you found that Graham thing?
Speaker 2:Yeah. Yeah. And like the first search thing was that Paul Graham essay titled, I think it's titled like how to not give up or something like that. And I read it and I was like, and it I mean, the the takeaway is like, if you just don't give up, you'll be successful. All you have to do is just not give up.
Speaker 2:And I was like, that's right. And so then I messaged you that whole thing about how, okay, we were clearly just like fantasizing and we're not going to give up. And here's all of the good things that we already have. And if we have all of those good things, there's no way we don't turn that into something eventually. And ever since that day, I've given myself some version of that, like once a week.
Speaker 2:Because it's really hard out here.
Speaker 1:Yeah. It's funny because, like, you did I think it literally said, like, if you if you don't die, you get rich. So it's something like that. As long as you don't die, you get rich.
Speaker 2:Of course, you like that angle.
Speaker 1:Yeah. I know. Because I love money. I'm only doing this for the money. Yeah.
Speaker 1:It's as stupid and simple as that sounded and as cliche as like quoting a Paul Graham essay is, like that did have a massive impact because, it is really that stupid and it's it's easy to forget that it's that simple because in the moments where you're like, I don't know if this is gonna go anywhere, like maybe you should give up and start over. You're forgetting that where you currently are is a result of one year of work, whatever it is. And if you give up and start over, you're just starting down that same path again from the beginning and you could easily just end up back in the same spot. But now you've wasted another year. So with all this stuff, as long as you just pick picked a big enough market, if just spend enough time in it and just continue to like tweak and learn and and try stuff.
Speaker 1:If you can just do that for like longer than other people, eventually you would just have to hit on something that works. Because this stuff takes time, right? It's the work is figuring out what to build. And everything before product market fit just feels like it's completely unknown, like you're out there to figure it out. But that's the actual work.
Speaker 1:Everything after that is like pretty basic. But the actual work and the miracle is like being able to spend that time with ambiguity and figuring out what figuring out just something that that can work. So ejecting out of that, just ejecting back into the same exact environment just from the beginning. So again, very very simple but that paulgram essay did because it like alright, maybe just because like the get rich part really really spoke to me. But yeah, it did like snap me out of that and I haven't felt that way even remotely close feeling that way since then across everything I'm doing.
Speaker 1:So yeah, that was an important moment. So this is your first time being a founder where you're literally the one responsible. I think you had some expectations of what it was gonna be like. I think it's very different than what you expected. So yeah, do you wanna talk about some of that?
Speaker 2:Yeah, the biggest difference is I've always been in like small environments, small number of people, three people, five people, 10 people, things like that. Always been good with ambiguity, giving myself work, figuring out what needs to be done and doing it. But I didn't appreciate how even then, even when I thought that there was ambiguity, there wasn't. There was already something, right? There was already like research studies that had protocols.
Speaker 2:There was already like a business. Like by the time I joined RITE Health, we had customers, we had a business, like it was clear, like things were clear. And I just did not, I was not prepared for what it feels like to be staring at a blank page and to just have to figure it out all completely on your own. And I wasn't prepared for like how lonely that is. Like I've always been in these environments that are really chaotic and I would see founders and leaders struggle to deal with the chaos.
Speaker 2:And I'm very, very, very good at managing chaos. Like, dream job is I coordinate an emergency room or something like that. Standing in the middle of it and like
Speaker 1:Or like a kitchen at a high end restaurant.
Speaker 2:Exactly. Yeah. So if there's like a bunch of stuff going on and it's super chaotic, it I think of myself as somebody who would do really well there. It'd be stressful, but I'd figure it out. And, you know, I I like that.
Speaker 2:There was just nothing like no chaos, nothing like no emails in my inbox, no Slack messages, no coworkers in the beginning, no customers, just nothing. Just like a whole day where my calendar is blank, which I'm sure to people who are like, they have a lot of meetings right now. That sounds amazing. Yeah, but also it's like, what do you do with the, what the hell do you do with yourself? It's like too much freedom.
Speaker 2:It kind of feels like the bottom is like ripped out from under you and you're just like falling into an abyss. It's like a very, it was honestly like a scary feeling for me. And I'm sure there's people who they actually wouldn't have a hard time with that, but for my particular temperament, very difficult, very, very difficult. And so, you know, the further we go, the more things that exist, the easier it gets for me. So we get customers, that's easier.
Speaker 2:I have people to talk to. I have like a way of looking at this and reducing degrees of freedom and things like that. It gets easier and easier, but I just wasn't expecting like the quiet to hit me so hard. And it's just hard, like you don't know where you're going or what you're doing. You're getting no feedback.
Speaker 2:You're getting no inputs. There's no coworker to be like, you're being annoying or you're being great. Or I love what you did or what you did sucks. Like there's just, there's nothing. There's nothing, nothing, nothing, nothing.
Speaker 2:And so you just keep plugging away and this thing is like going into the abyss and you're like, and yeah, I mean, it's gotten better, but I still struggle with it. Adam talked about this a little bit in the startups episode, but it wasn't like the thing. And for me, for where I am right now, this is like the thing. Like, this is like the struggle.
Speaker 1:Yeah. Yeah. It's easy to underestimate how much input most of us are getting all day. Even if you're an early stage company, like, there's just stuff usually happening and coming and coming in your way. And it might be annoying things, like, might be things you don't wanna deal with, but at least it's something.
Speaker 2:It gives you structure. You're like, I have an email. I have
Speaker 1:to
Speaker 2:reply
Speaker 1:to You have to do this. Like something is telling you what to do. There's like some signal telling you what to do and it is like, it's really easy to underestimate how shocking it is when you literally like nothing exists besides you doing stuff, you giving yourself your own input and trying to make stuff happen.
Speaker 2:Yeah. Building your own momentum.
Speaker 1:Like, startups only get easier over time because you just have more knowledge, more stuff happening, like like you said, degrees of freedom. In the beginning, like, you can do literally anything. Like, you have 10 potential things you could do. They all seem equally important. You have no idea which one makes sense.
Speaker 1:And as as it goes on, it's annoying because you wanna do 10 things but you are forced to do like one or two. And that's annoying, that's the environment that most of us are used to but it actually is kind of a blessing because it's you're kind of being told, okay, this is what you need to do and and it's clear. So very different early on and that's what I was saying earlier like, yeah, it's a miracle to get to a place where you have a product market fit and you have customers and everything because those initial phases are where people get filtered out because they're just so, like, weirdly hard and it's all, like, internal mental challenges. Nothing really, like, external. It's not really about, like, building a product or making a product look and feel good.
Speaker 1:It's it's all these, like, internal struggles you need to need to conquer.
Speaker 2:Yeah. Yeah. And this time, it's funny. I got really into reading these books that were like aimed at writers. And that all that stuff weirdly ended up being like very helpful because I think it kind of is like that, right?
Speaker 2:You're like staring at a blank page. It's just you alone all day trying to figure out how to structure your day, how to like bring this thing that's inside of you to life. I found it weirdly like comforting and helpful to kind of read through some of that stuff to kind of get me through this phase. I'm still in it, but I feel like we're at the tail end. Like, I think also like how long it has taken is not what I was expecting.
Speaker 2:And we kind of get into this all the time because you're like, I don't know what the hell you were expecting. Like things take forever. But I really have this narrative in my head that if it's gonna work, it works fast. And that things are supposed to be going really fast. And if they're not going really fast, then you're doing something wrong.
Speaker 2:You're never gonna be successful. Give up now, you total loser. Like that's the narrative that I have in my head. And I've found it hard to just like stop worrying about that piece of it. And I've found it hard to like tell myself like the type of product that we're building and the way that we chose to capitalize the company means that things are gonna be slower.
Speaker 2:It doesn't mean that it's wrong or that it's not gonna work out or that, you know, we're doing something massively wrong or.
Speaker 1:Yeah. And it's funny because we we have this discussion a lot because it took some convincing for you to believe that it like, this going this slow or, like, things feeling this slow is the norm. But if you like sit down and like go I think we sat down and I thought through like, okay, all the people that I know, whether they're like in it right now or whether they've already been successful, like how long did it actually take them? It takes a very long time and people it's like very easy to forget that. So with SST so I joined, I think it's gonna be two years two years ago.
Speaker 1:Frank and Jay had already been working on it for like four years before then. Three or four years, something like that. So from my point of view, I'm like, I basically started at the beginning and like, even then it's taking forever. They had already been working on it for like years and years and years before then. They had they've been working at other companies before that as well.
Speaker 1:And it does take a very long time and they're both very very good at what they do because of all all this time has gone gone by and and what they've learned in that. And that's the norm. Like everyone I know is like, even people that are massively successful, it's like it's taken 10 or so for them to really get to a place where things are humming. I think we get distracted by the weird times over the last five years where certain companies like rocketed to, you know, building out evaluation in like under two years. I think we're hearing that left and right.
Speaker 1:A lot of those were fake, like not real. Some of those are probably real, but the reality is is like, it's just not the norm. The norm is it just takes a very long time.
Speaker 2:Yeah. I know. I mean, I don't know, maybe. You're still not fully I was still not fully convinced. Yeah, exactly.
Speaker 2:It's just, it's hard because you don't have a guarantee, right? Like you go to med school, you go to grad school. It's gonna take a long time. Years, years of your life, like five, six, seven years. But you know, if you follow this path and you like do these things, you get this outcome.
Speaker 2:The startup isn't like that. We could be doing all of this and it could turn into nothing. And you feel this like opportunity cost of what if I had done something else? Of course, there's like a totally different way of looking at it, which I think you are very good at looking at it in a different, more helpful way. But that's kind of the fear.
Speaker 2:It's like, you just have no guarantee that you pour all of this stuff into it, but what if I'm pouring the wrong stuff? And over time it just, I spent ten years on it and nothing. But anyways, you have a much healthier perspective on that.
Speaker 1:Well, I just think about what's the worst case scenario. I yeah. The opportunity cost thing is there, but, the worst case scenario is you spend a bunch of years doing something a lot harder than what most people do. So if you spend five years on it versus someone spending five years at a company, you exert yourself a lot more over those five years and the reward for that is you've learned a lot more, you understand a lot more about the how the world works. You just are just becoming a more capable person at that time.
Speaker 1:So the worst case outcome is you'd kind of spend a bunch of time training really hard and that maybe sets you up for something really incredible as your next thing. I've always looked at my career as like just constant setup for the next thing. I think I'm getting to a phase where I think I'm like doing the stuff that I was training for. But yeah, I've everything I've I've worked my official career maybe is eleven years now. I've only worked at very small companies.
Speaker 1:I've only founded companies, I've been at very small companies. Every single one of them has failed. None of them has actually worked. Maybe save for one, but that's the one where I joined much later and wasn't, like, don't even count that one. So I've only had a career of failures.
Speaker 1:But I've gotten to a place in my like, own understanding and ability that's well well beyond what most people have, just because of those experiences. And I don't like I'm not sitting here looking back at that and feeling I think people imagine like, there's gonna be a moment where my stuff fails and I'm gonna feel terrible and look back on it and it all feels wasted. Just being in a situation where I think that is literally the situation I'm in, I don't look back on it. It just doesn't feel that way at all. Because you just continue to get excited about the next thing and you bring all all the skills with you and then, it just gets easier every single time.
Speaker 1:Like I remember, I used to work a lot harder, I think. Like I would like exert myself a lot more to just get worse results. And I can like sit back and think about where my energy would go to before and like how little of an outcome I would get and think about now where I spend my time and like how much bigger of an outcome. So it's the same thing, like if I just keep going eventually, the outcome becomes a thing that is big enough to be the thing that I that I want. So again, it's just it's just time.
Speaker 1:Just like knowing that nothing great happens without a lot a lot of time behind it.
Speaker 2:That's the thing I've like struggled to internalize because I ate up all these other stories about how it was so fast. But the other thing is it's just like it's just like embarrassing. Like it's embarrassing to be like, I'm gonna phone this company, you guys. And they're like, Hey Liz, like, how's it going? And you're like, Yeah, like no updates since the last time.
Speaker 2:That's embarrassing. It's embarrassing to think that, you know, at the end, it won't work out and everybody will be like, yeah. Well, you know so I don't know. I feel like you're very good at dealing with embarrassment or, like, not having it be a factor.
Speaker 1:Yeah. Have you seen our YouTube channel?
Speaker 2:Yeah. Can you tell like, talk a little bit about how you just like this is not like a factor for you at all. Embarrassment.
Speaker 1:It definitely I wouldn't say it's not a factor and I definitely know exactly what you're talking about because I, like, you know, definitely earlier in my career, it was like more of an impact. I think I was always so motivated by proving people wrong. I would just like make up fake enemies in my head. I pretend like someone cared about what I was doing way more and I wanted to prove them wrong. They probably didn't really care that much.
Speaker 1:So that kind of like pushed me forward, at some point. I mean, everyone's heard this quote, Nikita Beers quote where, I forgot what it is. It's about like, literally the thing that's stopping you from getting to the next level is like, being worried about looking bad or like being embarrassed. Mhmm. And again, are just filters that we talked about, things that filter people out.
Speaker 1:And some part of that clicked for me where I was like, oh, yeah, if I just randomly do stuff that's more embarrassing, I'm like now in the 1% of people because 99% of people would have just not done it. So now I get excited to do things that are embarrassing because I'm like this is an edge, it feels like an edge for me. I definitely remember it like, YouTube's a great example because when I first was hearing about the YouTube stuff, and I would see all like the stupid ass thumbnails and I would be like, that's so embarrassing. Like, my friends who know me are gonna see that and they're gonna be like, what are you doing? Like, that's not who you are.
Speaker 1:And I was, like, rationalizing all the stuff in my head about why I would never do that. And then over time, I, like, started to learn, a little bit more and I, like, rationalized it in, like, a stupidly intellectual way, like, where I was, like, I'm above that. I need to do that. But really, it was just me being scared. Eventually, it just sort of makes I started to understand it and it started to make sense.
Speaker 1:And it really flipped to a place where I'm like, now I just genuinely enjoy it. It doesn't even feel embarrassing. It just feels really funny. It feels really creative. So yeah, a lot times it doesn't work, you know, but the thing we talk about all the time is everything we try to do, we try to it just has to have the potential of being a massive hit.
Speaker 1:Doing a conservative bet is not worth it because the reality is you need to try a 100 things and one of those things will work. If the one thing that works is a conservative bet, like you didn't really get anything out of it. So yeah, I'm just like really now excited about trying all these crazy things and like I said, my whole career has been a failure in a way. So at this point, I'm not like worried about it. I'm still in a great great place.
Speaker 1:So it kind of doesn't yeah, just internalize it just doesn't really matter. I think everyone kind of feels that way when they get older also. Like, we all know like the older people in our family that just like don't give a shit about what anyone thinks. So I think it just kind of is like a natural thing that happens.
Speaker 2:Yeah. That part about dragging your competitors through embarrassment really clicked for me.
Speaker 1:Yeah, exactly. Yeah. So once we do boomy marketing, it's gonna be really embarrassing.
Speaker 2:Yeah. I'm excited for that. I think the other night I told you like, hey, by the way, you're definitely in charge of the marketing. And that's something that even a year ago, like, I would have never said because I wanted to, like, really be in control of it and be in control of, like, being perceived in a certain way. And now that I've worked my ass off, the only thing that I care about is that people know that it exists.
Speaker 1:Yeah. That it works.
Speaker 2:Like nothing matters. Know it exists. I literally just want peep no. I know it works.
Speaker 1:No. No. No. Not not the product. I mean, that the marketing works.
Speaker 1:It doesn't matter what it is.
Speaker 2:Exactly. Exactly. Exactly. All I care about is that people know that it exists. Like, I can't just have worked that hard on this thing that I know is awesome for it to just fail because people just don't know it exists.
Speaker 2:So I'm definitely willing to do, like, literally any like, anything.
Speaker 1:Yeah. And that's just that's what I'm talking about. Like, it just it's such a natural transition where, like, you'd, like, have all these thoughts and, like, opinions about it. But you guys get to a place where you're like, I will do anything that that works. If it works, I'll do it.
Speaker 1:I don't care what it is.
Speaker 2:That's the other thing about being a founder is you get so, like, like, religious. Like, I will literally, like, I will pray to God. Like, I will give this offering to this goddess at this temple. Like, just help me. I'm trying so hard.
Speaker 1:When we were visiting my parents, my mom got Liz this what is it? The idol?
Speaker 2:Akshmi.
Speaker 1:Yes. The goddess of wealth.
Speaker 2:Prosperity.
Speaker 1:Prosperity. And and and what what
Speaker 2:Well, she gave me options. She was like, you could get like this one or that one and I was like, yeah, the prosperity one for sure. Like, give it here.
Speaker 1:And now it's on her shelf and then let's praise to it.
Speaker 2:I do.
Speaker 1:Yeah. Whatever we'll do whatever it takes.
Speaker 2:Whatever it takes.
Speaker 1:Yeah. It's funny. This reminds me of Frank a lot because Frank is like most of the time, people know Frank is like, he's just working. He's like very like focused on his work and it's like seems kind of serious. So when we started doing all this weird YouTube stuff, in my head, I couldn't really picture him outside of like like, he's always funny but like, I couldn't really picture it but he he's like the definition of he will literally do whatever it is and historically, it's
Speaker 2:been Mhmm.
Speaker 1:It's looked like just working super hard and cranking out like a bunch of work. But as soon as it became, like, we needed to like be funny on video, he just went super hard. He didn't even think about it. He didn't even like question it. Didn't ask questions about like, he didn't like clarify what does it make.
Speaker 1:He just went way harder than I expected. Because again, he's been doing this for so long. He's again at that point where, yeah, we'll all just do literally anything. If it seems like it can work, like, we'll we'll take a shot.
Speaker 2:Yeah. And it's cool that he gets to express that part of himself. And I feel like you guys have a lot of fun and it's it is kinda like I mean, it's corny and basic, but, like, yeah, at the end of the day, like, it's the journey. You gotta you do you have to enjoy it like you do. But otherwise, you lose motivation, you're gonna give up and it's all gonna be for nothing.
Speaker 2:And that's a tragedy.
Speaker 1:Yeah. I will say it's all very very fun. I think we talked about how intense all this and some of the painful parts of it. But there's to me, there's really nothing more fun in my life than than working on all this. It's just like, we do have a lot a lot of fun every single day.
Speaker 1:The frustrations we feel are things that feel worth it. Like I'm frustrated because our product isn't good enough or like we haven't found the right way to talk to our customers or like we haven't thought about the right features. Those are great frustrations. Like they don't like kill you over time. The frustrations a lot people run into is like, my boss is an idiot or like we're using a stupid we're using Jira and it sucks every I I wanna kill myself every time I'm in it.
Speaker 1:Like, all those, like, micro frustrations you find, like, that is what really kills your motivation over time. The frustrations I think we have are good ones to have. They feel healthy.
Speaker 2:Yeah. I I totally agree. As somebody who has spent their entire career frustrated, I totally agree.
Speaker 1:Career. Your entire life frustrated.
Speaker 2:My entire life frustrated. Yeah.
Speaker 1:Okay. Well, it was really good. I think it was great. And do think it was better than me and Adam's episode?
Speaker 2:For like the stuff I wanted to hear reflected in the world.
Speaker 1:Oh, yeah. I qualify it. She thinks it's better. She thinks it's better. Adam says yes.
Speaker 1:Adam says it is. It is better.
Speaker 2:I don't know. We'll we'll see. We'll see like what the people what what the people say.
Speaker 1:We'll see what shorts we attract out of this. Alright. Cool. Thank you for joining and, have a good day. I'll see you in the other room in a second.
Speaker 2:Alright. Alright. Bye. Bye.
