On this week’s episode I chat with Darius Monsef, Founder and CEO of Brave Care.

Brave Care is creating a new, better healthcare system for kids by providing primary, urgent & remote care catered just for them, 365 days a year. By tech-enabling a system that’s been long overdue for an upgrade, Darius hopes to make Brave Care the premier children’s healthcare partner for parents.

Interplay is lucky enough to be an early investor in the company and we absolutely love their mission.

Darius is a serial entrepreneur with multiple successful exits. You might think that things get easier for entrepreneurs with each new company they start, but the journey is always an arduous one. Darius and I explore this topic (which includes a thoughtful and - IMO - very helpful discussion about wealth in the tech community), why he went through Ycombinator multiple times, the startup scene in Portland, and much more.

It was a great conversation. I hope you enjoy it.

Show Links


MPD: Thanks for being on.

Darius Monsef: [00:01:43] It's good to be here. Thanks for having me. 

MPD: [00:01:45] Yeah, absolutely. So I'm going to start off by Doris by just introducing you. Uh, I'll help people get ramped up a little bit. We can dive into more topical issues. Sure. So for those who don't know, Doris, he's a serial successful serial entrepreneur.

He is on his fourth venture backed company. His current venture, where he is the CEO and co-founder is a company named brave care. The company is re-imagining health care for children, uh, for full disclosure, interplay is an investor and suffice it to say, we think he's doing something awesome. So pay attention, uh, before brave care, he was a co-founder of a number of other companies, including Sidebox credit market.

He's had successful exit. Um, and before going out as an entrepreneur and I may be integrated in some of your entrepreneurial story, he spent some time as a head of growth at Zapier. And I have a question for you after this, because I don't think anyone knows how to pronounce the company name. There's a lot of Zapier and Zapier.

No one knows, you know, to correct each other on that. It's confusing. Uh, he did a tour through Autodesk, Microsoft, um, and you know, there's another side to Daria's, which I don't know if we're going to cover too much today. He has an eclectic side and I don't know if it's all true, but at least he, at least he lists online that he is a ballroom dancer and cattle rancher.

So there might be some times opportunities to talk about that you went deep. 

Darius Monsef: [00:03:05] There you 

MPD: [00:03:05] go. Uh, and he's very passionate about impact and involved with a number of charities, including Make-A-Wish and others. And I think it's no surprise that his current vendor. Is oriented towards the social impact of having a positive impact on children.

What did I miss before we jump in? 

Darius Monsef: [00:03:20] Uh, also co-founded two different nonprofits, but I sort of, that could be in the realm of successful ventures, but, you know, basically trying to build things that make the world a little bit better, both for-profit and, um, I 

MPD: [00:03:31] love how prolific you are. So let's start off, uh, maybe go reverse order.

Would you start by just giving an overview of brave care? So folks have some context to what you're working on. 

Darius Monsef: [00:03:40] Sure. Yeah. I met my co-founder. Who's a pediatric MD when my middle daughter split her chin at a bike park, uh, as a parent of a nine, six and three year old young kids. Uh, although we are most concerned about the injuries of the first one, we sort of three kids and a little less concerned about them, but I met him in an emergency visit.

Uh, my middle daughter needed to get her chin stitched up and I am in a fortunate position to have access to whatever healthcare I need for my kids, but got to experience the really uncomfortable position of a parent. Who's really concerned about their kid in these urgent situations. Um, met him, got incredibly good care and sort of came out of that going.

I think every parent deserves access to that, regardless of a financial position, a lot of parents end up in the ER there's 25 million ER, visits a year for kids that are mostly unnecessary because they don't have action, uh, access to after hours or weekend care options. So brave care is trying to take primary urgent and remote care, build it out of the same, you know, kid friendly, but pairing, uh, Design clinics to make everybody the two sides of our transaction, the, both the parent and the child fairly comfortable so that we can deliver the best medical care possible.

Um, we, I come from a technology background, so using technology to, to build the best personal and thoughtful experiences, not putting technology between a patient, um, and a parent or a child, but using it as a way to make it a more efficient visit for, for both sides of that. And the ultimate goal is to be the national children's health care partner for.

MPD: [00:05:16] That's amazing. And, you know, hell hath no fury like a frustrated customer who happens to be a serial founder. Yes. Yeah. So we actually I've had a, a bad urgent care, uh, experience and same type of thing. I feel like stitches is the reason you go to the ER, as a parent. And my little guy, uh, ripped open his eyebrow when infrastructure is fine, doubt the stitches, they got it done $26,000 bill for three stitches.

And so the game is clearly dysfunctional and they expect you to dispute it, right. They're just taking advantage of people who don't know the, how the system works and you have to fight. So I I'd love to hear how you are approaching the market differently. So folks could, you know, get an understanding of.

More than making healthcare affordable and good. How do you do it? And what is the, how does it experience fundamentally different from 

Darius Monsef: [00:06:07] parents? Yep. So part of what you're talking about is we typically just say we're 10 X, you know, cheaper one 10th, the cost of an ER, visit in New York. Uh, we wouldn't even have been $2,600.

And I think my daughter's stitches were four or $500, so substantially less. And it's about so much more mailable economies of, uh, basically a much larger organization or rental hospital. They charge more just for the basic visit fee. And then all the things you sort of experience with just. You know, uh, an unfortunate need to dispute costs rather than transparent pricing.

So what has been challenging about healthcare is I come from consumer tech and, you know, the common startup mantras move, fast break, things like that. Doesn't really work in the healthcare it's regulated. As in some ways it should be, you have medical licensing. We have payer agreements with get hit and privacy compliance.

There's a ton of layers of bureaucracy. Fortunately, that also means there's a lot of room for improvement. It's just hard to get it done in this space. Um, I. Great. Co-founders who have medical backgrounds. I try and tread the balance of naivety about how healthcare currently works, because I'm not trying to integrate and only improve some bullshit in the middle.

We're trying to dramatically move it forward. So I don't really want to calibrate to how it is now. And then look for improvements. It's just what could or should it be? And that is access. You know, either through technology or just broader hours of an in-person, is it, um, patient data, 74% of healthcare data is still transferred via fax, which is insane.

Uh, or it should be digitize all these patient records without the Manila folders on the wall anymore. But now they're digital Manila folders because those images that were scanned haven't even been OCR so that we know what's in them. They're just images that one person has to go reference. So. Such dramatic improvements can be built if we just built the best clean single queryable data set of lots of, you know, wellness tracking events for kids tracking, escalations, and then ultimately outcomes.

So that whether us or a children's hospital, you could someday just say, here's all this data, like go stop these really unfortunate events from happening in the future. Um, so it dramatically moves forward with actually modernizing it and not modernizing it where. You need to walk in and talk to a robot or whatever, especially in pediatrics, like kids believe in magic still.

So if this space is scary, if there's not somebody warm and personal on those to get on their level versus being a giant adult, there's a lot of things that can disarm a kid. And that really helps you, uh, deliver the best care. And we can talk a little bit about it or not, but a tele-health has limited impact in pediatrics.

COVID was the perfect opportunity. To use this technology to open up access and transform it. And in pediatrics, you need the patient to be able to accurately describe the issue that they're having. I can tell you, I have a strained ACL on the back of my knee on full extension. I have a sharp pain.

Otherwise it's a dull ache. My nine-year-old is just going to say her leg hurts. You might even say her back hurts because she doesn't understand sort of referral pain. And a two year old has no ability to communicate any of this. Even in person, the difference between a family practice or somebody who hasn't been as experienced with kids, isn't, it might be less skilled at really getting the kids to relax and be disarmed so that we can get good information out and we can do a good diagnosis and treatment.

So that's where the specialty and specialization and, you know, working with kids comes in and then the technology is, well, how do we open access without removing this personal relationship that you can form with somebody who knows your kid and knows how to treat. 

MPD: [00:09:47] So you're cleaning the data. I get that part for the folks listening.

Why would they choose to go to brave care over their current combination of a pediatrician? ER, urgent care, Kim 

Darius Monsef: [00:10:00] build the most complete solution. So I have been to brave care, 24 times as a patient, as a parent, not as the CEO walked in and dependent on them to take care of me the same way they take care of somebody else.

Um, Unpleasantly. I am a regular consumer of my own services because a lot of those visits are urgent or unplanned, but trying to be one consistent partner for a family. So, you know, the primary care visits, those are scheduled. We know those are coming. The unplanned unfortunate, urgent care options. We're open 10:00 AM to 10:00 PM, seven days a week.

You can do a walk-in same day appointment. So even the challenge and often white people, over-utilize the ER, especially 21 million single parents in the room. They have jobs that don't particularly give them time off during working hours to get in. And then I've got to pull my kid out of school in order to this appointment.

So. They're trying to make a good financial decision by going after hours, but then often the only thing available after hours ends up being an ER. And so simply being able to have, Hey, 7:00 PM on a Saturday, if that's when you need to get your well visit in for your kid, that's fine for us. So the convenience of access, meaning the hours and availability.

We have 24 7 chat through our app. We staff our own pediatric triage nurses. So again, it's not just somebody who answers and says, well, let me get back to you. We are able to understand and give you good, actionable information through the chat service. And then we have x-rays and pharmacy onsite because it is again, I've been in a clinic where we needed Tamiflu.

And now I got, gotta hold a couple of sick kids and go to the pharmacy and wait for 30 minutes. It's like, let's just do that for you in clinic and let you get home and get back to your life. So trying to really provide the most complete offering for parents and then use technology to ultimately give you your child's personal health record in an app.

So that over time you can track progress to early intervention or just best support your kid where they're at. 

MPD: [00:11:53] What do you think the most common use cases will be for the data side of it, the early intervention. And where do you think that really manifests for folks? 

Darius Monsef: [00:12:01] I think there's a lot of opportunity for subtle intervention.

So my wife is a speech language pathologist focused on early intervention and language delays for kids, which is the longest way to say speech delays. Um, but her skill is, you know, helping kids. Move their mouth in a way, and basically form language she can hear and know that this kid's got this little issue and it's often hard for her in a social setting, obviously to bring this up and suggest it to a parent.

But it's one of those where the sooner that you do that intervention, the kid's going to have an easier time communicating. They're going more confident, social, like it has such a dramatic impact in often it can be this small, but fixable. That we can hear, like, that's an easier example to sort of like, oh right.

I can hear when a kid has a lisp or maybe there's a delay in some of the words, but we want to figure out is what are all the other things that might be under them? Height, weight, motor skills, other things that we probably are collecting and all those digital Manila folders we can't get access to. But if we put them all into one.

It's just an opportunity to help every kid reach their potential by using the information that is being collected. It just isn't usable. Right. 

MPD: [00:13:09] Are there other research organizations that are compiling the data and making sense of patterns and signal in it, or has that not even been done because all these Manila folders, 

Darius Monsef: [00:13:19] I think there are physicians doing it.

I mean, we've got great children's hospitals around the country. They're doing it with the ax, with the data they have access to. But even, I don't remember how many there were. Um, there are. Probably hundreds of EHR, EMR is this is the software that every clinic uses to run their business. Those don't connect to each other.

We've had to move a couple of times and like I'm getting PDF images. Every single time I move the data does not connect and sync. So our hospital systems are having access to only the data that has been collected. There are very large players like epic that do probably have a lot of patient data, but it's not.

Anywhere near as substantial as it could be that we have access to. 

MPD: [00:14:02] That's not the way we think of things in the tech community. 

Darius Monsef: [00:14:06] No, I'm often, you know, the interesting balance to being between being a consumer kind of oriented startup as well as a healthcare is that the consumer startup people, when I'm pitching them and I could show them our check-in app.

An iPad. We just hand to you, so you don't have to sit in the visit room and then it's this really beautiful step through, take a photo of your insurance card. If I demo that to a consumer investor, they're like, yeah, whatever. It's like, no, no, no, no, no. But like in healthcare it was really hard to do, like, this is magical in this space.

This is just super basic in any consumer app. So right in healthcare they're they're miles behind where we could be compared to anything 

MPD: [00:14:41] else. So how's it 

Darius Monsef: [00:14:42] going? It's going very well. Um, it's was a hard year. Um, so our story, basically two years ago, we got started. We, I took over the clinic. I went into versus a patient.

It became our first brave care clinic. And honestly, we started in a position really tackling the ER, the urgent care side of things. Let's pull these millions of ER, visits away by having urgent cares. What we learned about moving forward with that though is. Nobody wants to have a relationship with an urgent care.

I'm like actively trying never to come to you. And so if we wanted to build a relationship and have a consistent touch point, that was to move into primary care, which is exactly what primary care is. It's a relationship I'm expecting you to come in at least once a year. And so, as we got started, we sort of evolved the platform to say, oh, well, primary care really adds value to the urgent care.

And when you are somebody's primary, you can capture the urgent. So there's this reciprocal relationship between those two sides of sorts. And then we are always going to build great technology because it's my background and where there's opportunities, but COVID allowed us. Basically, we were growing very well.

We went through Y Combinator, summer 19 batch. So it gets to be a year and a half ago had raised a big seed round, really had the resources to go and grow, open more clinics. And then COVID sort of took the wind out of our sales early March. Um, Had anybody provide any other data? So I believe it's true. I think we were the first of any company to ship a COVID symptom checker.

So March 2nd, 2020, we repurposed the logic sort of tools that we had built for symptom checking to build a COVID symptom. When we shipped that we very quickly responded and built tele-health for, for 14 different things. But limited utility. I mean, there's only kind of visually diagnosable things. And if you looked at we've done more than 13,000 visits, now we're going to publish a paper on it.

But it's like 70, 80% of those visits that we did in clinic had to have been done in clinic. It's a shot, a stitch, a lab, and x-ray breathing treatment and things that there's no dongle on. Uh, any device that's going to facilitate in the near term. Right. So we did what we could. Um, it was really hard there through the fall, but the harder thing that we did was we raised a little bit more money to maintain the momentum we had sort of like leaning into the abyss instead of doing this.

I understand why startups would do it. We'll skeleton crew. Let's make sure we survive. What we saw was that. You know, as a startup, you kind of planning to lose money every month for some long period of time, that's not how normal businesses operate. So COVID just meant I was bleeding more than I was already planning to bleed, but for a typical kind of small business clinic that's can be catastrophic to have several months of no income or very little income.

So as the overall capacity for pediatric care would be reduced. If we leaned into this and got our second clinic built a mobile clinic, increased capacity, the goal was that when there would be a return in demand, we'd just be better positioned to capture it. So it turned out to be the right decision. We went ahead and.

During a pandemic with riots and a recession, and then fires in Portland, Oregon. We still got our second clinic open, which was hard to do, and we had our mobile clinic. And then in the fall we saw a pretty dramatic return, uh, in visit volume. A lot of that underline is COVID tested. We do rapid COVID tests, um, in both of our clinics.

So enough overturning growth to validate all these assumptions that we had when we started to be able to go raise our series a, which we just closed, which appreciate your support and to do the next phase of this, we've made it, made it work in one market. I think Portland was a great market and that it is a lot, like I'm an importance of special city for a number of reasons, but it's a lot like 70 other cities that are half a million to a million population in the us.

By making it work in a city like that just better helped us understand that we could also do this in a number of other cities. And our expansion plan is not tier one high density, urban markets, because often that's where families or people defer families for careers. We want to know that we can exist in tier two and tier three markets where people have more kids and get started earlier.

So the series a is letting us drive that expansion, which is what we're doing now. We're opening four additional clinics building the next couple. Um, mobile clinics and then having to build all of the software on the backend to enable us to deliver care. So, uh, it's, it's good. I, you know, it's always fun coming off of a fundraising announcement cause you get a lot of congrats on social, right?

It's like getting a giant credit card. It's like, thanks. I have a lot of work to go do with this money now, but it looks nice. Feels nice. I think it is not easy. 

MPD: [00:19:05] You have to hire people. 

Darius Monsef: [00:19:07] Yes, that's tough also because we've been well capitalized here and it was required because we had to do hard things was it's it is I think, dangerous and easy to spend money when you raise a lot of it.

So that's also the balance of not leaning so much on like, oh, just hire the person to solve this problem. But like, do we really need to solve it? There's another kind of critical eye that really has to be used when you're welding. 

MPD: [00:19:29] Hmm. So what, what cities are you going to next? So where should listeners look for the next brave care locations?

Darius Monsef: [00:19:35] We're already two in Portland, sort of a home market. We'll expand them to the Beaverton area. Portland, Austin is our first sort of major new market that we're opening. And we're, uh, also moving into North Carolina. It's an exciting opportunity for us to test out a different way to expand into new markets, which popped up in, in North Carolina.

MPD: [00:19:52] That's fantastic. So can we talk about Portland for a second? So it's not one of the primary startup hubs historically. Yep. The world is decentralizing and a wonderful way. What is the, what's your experience as a founder in Portland? Is it a viable place to be doing business? What do you think about the, uh, the region?

Darius Monsef: [00:20:14] I have mixed feelings of it. I've sort of lived on and off in Portland for 15 years. I started my first company color lever is the first thing that ever became venture backed. And then I had an, uh, an exit. So, uh, there is a love frustration with the market. I think in terms of a community to live in for my kids to sort of feel more normal and be around it makes the people think Portland's great for that.

So quality of life is incredibly high. There is a tech scene. Um, I it's clearly not as strong as some other markets. I mean, LA San Fran, Cisco now Miami New York, like you just around so many other peers that are actively doing what you're doing. Uh, Portland, I still think is probably a lot more optimistic or ambitious about doing startups than it actually is happening in market.

I think as me, interesting post COVID how much more it gets distributed though. Cause I, despite, you know, even my previous company that I co-founded site box had a very big exit for Portland. Tech startup scene, right after that raising money for brave care. I don't have any Portland investors. Yeah, I went, it was, I went back to the bay area and LA and New York and Boston.

I, we didn't have. Maybe for me, because I'm used to things moving faster, the kind of investor that I wanted to spend my time with gear in Portland. Um, but I think again, this sort of a decentralization of where startups need to be. Uh, I didn't, even for my series, a huge benefit of doing it during COVID is I ended up doing in-person so I wasn't flying all over the country.

Like I normally am. So if we're okay, doesn't matter. Yeah. If we're doing this now, maybe I can keep my company here. I don't get pulled to the bay or somewhere else where I need to have these in-person meetings. So I think. Hopefully the startup scene catches up to the high quality of, of life here. Um, but again, I think it's a mix, uh, sort of give and take 

MPD: [00:22:03] with remote investing fundraising process right away.

You don't have to meet the invest investors in person. What is missing from the Parlin ecosystem for folks listening, who are, would be entrepreneurs or entrepreneurs and other cities, which should they come and ask to Portland or help build to put pajamas? 

Darius Monsef: [00:22:21] I think it's boost it's builders is exactly the point.

Um, Portland again has benefited from some incredible, you know, Nike's here, uh, Columbia sportswear. There's these big companies that I think have built great products and companies, but people that come Intel's you come from kind of long-term employment. There's just less. Risk tolerance to go actually do this startups.

And so I think a lot of the community here has historically dabbled there, dangled their feet in the water. Yeah. Versus that I'm going all in on this thing. Cause I believe it to be true, fail or succeed. And I try and find those. I small, I make tiny angel investments, but mostly I do it because fortunate enough to one be privileged in many ways.

Ways, uh, but one of them is, uh, previous experience living in San Francisco, going through Y Combinator, twice, having access to a lot of investors, meeting founders who are here in saying, look, if you're going to go all in on this, then I will back you early and I'll try and help you through this fundraising process.

Cause that's really counterintuitive in a lot of different ways. What no offense y'all look for and how you run your processes. It really is an opposite sometimes for how I run my company and how I think about what I'm doing. So just helping somebody navigate these things just cause I've done it before two times absolutely is something that I think is helpful for the kids.

MPD: [00:23:38] And you had moved to Portland from San Francisco, the bay area, right? 

Darius Monsef: [00:23:42] He has a little, there's a couple other stops there in between. So my wife and I are both born and raised in Hawaii. Um, we, I was at Microsoft at the time. We met second grade, uh, when we first met, but ten-year high school reunion was the full reconnection of us getting together.

She was in San Francisco. I really wanted to do this startup. That I'd started full-time. So I moved from Seattle. I left Microsoft and I moved to San Francisco full-time with all that. I owned in a car and no savings, but luckily she was very supportive of it. She saw some potential, she should be an investor because clearly.

Not a lot of resources at the time, but, um, lived in San Francisco, went through Y Combinator. When we got ready to have our first kid, we tried to move back to Hawaii, um, and live there. And then probably a year into that, I got sucked back cause there was zero community out there to support what I was doing.

So we moved back to San Francisco and then post exit to Autodesk of that company. Getting ready to have her second kid. We moved home to Hawaii. Again, this is where a post exit. I can choose how to spend my time. Again, very, uh, lucky in being able to get an exit that would set us up that way. Uh, this is where we bought 40 acres in our hometown.

I got cattle. Well, I spent, I would say three years started jokingly losing my mind. Um, and then ultimately I ended up losing your mind. I for better or worse am most fulfilled by doing hard things. And startups are every single day. Some there's some challenge. There's something that I have to rise to. Um, I should know this as being from Hawaii.

Hawaii's culture is a little bit of the opposite of that really. It's, it's there to relax or connect with nature and not your device or all the busy-ness. So when I got home having come off of a decade of high energy startups, I filled my life with all of the same. Chaos and stress, but none of the fulfilling, it was just like I had land to take care of.

I had a house we were building, it was just busy-ness with none of the fulfillment, my analogy. I was chain sign water until that motor blew. And I really had like a popping depressive moment where. Oh, all of these layers of privilege are hiding the fact that I'm depressed. I'm not happy even with all the things that I was able to have access to what mattered most to me, it'd be the fulfillment of building and making wasn't there.

And again, supportive wife and that we've basically had a dream life in Hawaii is like, I think we have to move out of here. We got to go. Didn't want to go back to the bay area. We really, again, we mentioned this a little bit earlier. I'm trying to sneakily get my kids to not know all of the privileges they have and just sort of live a more normal life as long as possible.

And Portland felt like a great way to just live in a normal community and be around that. She let us do this test and move back to Portland, uh, which fortunately worked well. It gave me the energy and inspiration again. And then my daughter obviously got hurt, which is how we started brave care for COVID.

We moved back there early on because we felt like man, there was space. We have now been in Hawaii, although important Portland right now for more than a year, just because there was lower, lower COVID case rates. And it was a nice place there. If you're going to run things remotely, having them all three kids be able to be in school was it was a pretty supportive environment.

MPD: [00:26:57] That's great. So one thing you kind of alluded to there's, um, choosing to go to Portland versus back to San Fran and given that there's a huge ecosystem in the valley, um, you are networked in the valley. Why not raise the family there? 

Darius Monsef: [00:27:12] It's probably a couple of things. One. Obviously it makes sense. A lot of my friends are all startup founders and my wife one does not care about technology or startups or any of that.

It's a good balance for us to have in our home. But also it means like when you have a dinner conversation with a group of people, it's not even just about the device, it's about the SDK that just released for the new version of whatever. It's like, that's not interesting normal people conversation. So it was always harder for her to engage.

In just what people were interested down there. Um, and I think also, you know, because I had this position of the fortunate place of already building those relationships, I knew that I can same day fly to San Francisco. If I needed to, if I needed to maintain those socials, I could from Portland, but really setting my family up for the best life felt like Portland would be the place to do it.

Um, and then also. The hyper we've talked a little, those two, that's just the focus on wealth that happens in San Francisco. And it's fine. Cause it to be fair, it's a lot of our motivation. Like honestly, you probably, it shouldn't be your only motivation to go do entrepreneurship in Texas, but clearly that is the most massive exponential way to build wealth in a short period of time.

So it is obviously right. But I didn't want my life to be so much focused on that. And I've had exits I'm in a very fortunate position, but we're always in this world of comparing ourselves to whomever is over the neighbor's fence. And among startup founders, the personality as a offense is like a mega billionaire and is just sort of like a very distorted reality, uh, depressing thing versus like, oh, we're actually like incredibly well positioned compared to most, every other family.

Let me try and remember that every day, rather than feeling jealous of what somebody else has. 

MPD: [00:29:01] Yeah. It's a very strange dynamic. The relationship with money in the tech community in particular, because fortunes change so quickly for folks. You know, the poor entrepreneur walking through your hallways, you know, a couple of years ago.

After their exit, their, the, the very affluent, super wealthy angel LP, you know, running their own family office, the whole thing, you know, I think I hear what you're saying. It's very hard to stay grounded because, um, as you're in this career for awhile, you know, if you're talking to people, if there's going to be success, which is a beautiful thing, I love seeing all my friends doing well, but it's, you have to remember to look down, not up so you can appreciate.

Where you are in the stack and be grateful for it. I think it's very hard psychologically for folks. Um, so I think this is a common thing, actually, I, we, I think we both probably know people who made a lot of money and that got them into different circles and then became depressed about how poor they were, even 

Darius Monsef: [00:29:57] though they were rich.

Well, I think the other thing I recognize, and I don't think. Fully recognizing my luck takes away from the hard work I also put in, but I also know people who have worked harder than me and not been lucky enough to have the exit. My greatest fear as a parent was going to be. Coming back in to a late dinner and telling my kids like this is going to be the one it's like, I dragged them through 20 years because I knew I'd never let that go.

I would be trying for my whole life to have some validation that I could build or that I have good ideas or whatever it is. And. I was very lucky and I've obviously put hard work into manifesting that look, but I know great people who haven't had that yet. And so you not only have the, let me compare myself up often, there's the carnage down below of people who are putting their lives and dreams and may not ever make it there.

And that's like sometimes looking down and it can be as depressing as it is looking up. I want it to be able to be in a position to try and give back where I can, but overall put myself in a position for my family, at least to be fairly neutral to that. 

MPD: [00:31:04] That's a great perspective. Uh, one thing that's interesting about your story is the fact that you went through Y Combinator twice.

Um, you know, I, I think most entrepreneurs would look at that and say, Hey, you go through the first time you get the network, you learn what they have to teach you. And the next time you just do it solo. Yep. Uh, I'd be interested to hear your rationale for the second journey through Y Combinator. 

Darius Monsef: [00:31:28] What was funny is when I got accepted the second time my brain went like, oh, I'm a two time YC founder.

This puts me in some exclusive club. And then I thought, well, probably the super successful YC founders don't have to come back a second time. So it was kind of a funny backhanded compliment to me self. Um, but honestly why I did it was that when I came out of Seattle and having lived in Portland before.

I had no access to the bay area. I didn't know how to raise around. I was cold emailing investors. It was never going to work out. So YC was this massive opportunity for me to sort of get into startups and do it for real. So, I mean, it was life changing to get. In the first time we had raised seed rounds for that company, we had a great exit life-changing, uh, to

In 2014 and then this is when we thought, oh, we're going to move to Hawaii permanently. And so the three years I spent, I did do another startup, two of them, technically I co-founded Sidebox, but largely that was my very good friend, Travis, who is founder and CEO. And he ran that in clarity really well. I was just the big shove out the door, but I did try and build my own startup from Hawaii.

I was flying to LA all the time. I did that one didn't work. So I'm sort of two for two is what my success rate is so far. Um, But, you know, tangent there on unfilled. So why did 

MPD: [00:32:49] you, why'd you go back to why comment or for the second round? Yeah. 

Darius Monsef: [00:32:54] Because I basically killed my reputation for three years.

Like what's interesting in startups in tech is that it's almost better to have a massive failure than to just be quiet for some period of time. Like if I raised tens of millions of dollars in a huge blowout failure, it probably would have been better for my career for my network than to have sort of limped along quietly on a startup for three years.

And so. When I came back, what really one motivation for me and doing Y Combinator again, was how do I kickstart all that I built before? What's the fastest path back for me to get on this podcast to sort of have awareness, to be a part of these founder leaders. And Y Combinator is really specifically built for that.

It's to help you very quickly build hype momentum and connection for your company. I think it was interesting. Uh, I don't know if YC would like this perspective or not. But I think what every other accelerator incubator gets wrong that is modeled after YC is that YC is not about the company you're building.

It's not mission and value statements, only things it's just raising that first round of funding, because if you cannot get a product and validate it, then none of that other stuff matters. And so, so many of the other ones that compete and I'm a mentor to some of those other ones with YC, they add all this curriculum and plan time to try and.

You know, compete with YC, but all that curriculum doesn't matter. If the company can have a product that people will start paying for as fast as possible. So YC is this a pressure cooker momentum towards raising around the second time through, this is a sort of a funny, full circle is when you're first doing my company, which was color lovers, which became creative.

I was like building a design community with color pre this sort of big Figma sketch design Renaissance that we had. So it was hard to raise those rounds. And I watched other startups is the other problem with venture startup life is like, wow, how did that start up? Raise this massive round, like what we've got so much more validation than them, and that can be depressing.

Um, and Gumroad was one of those companies we I'd met Sahil out in New York several months before that. I think he maybe was still at Penn. And then he moved out. San Francisco raises huge round for Gumroad and I was so jealous. I mean, for a number of years, I think I held like almost animosity and that I wanted it to not work because that's somehow validated me.

But one, he did a very thoughtful post. Not that long ago, maybe last year, about how hard it was, even when he raised that round. And then I'd sent him a note. Cause it was like, that sucks for so long. I almost wanted him to fail to make me feel good. And I was like, oh, I'm so sorry. I don't want any of that.

I, uh, fortunately we were able to reconnect and full disclosure. He's also one of our investors now. But this time, when we went back through brave care, we were one of the hype companies. We were sort of raised the second biggest round during YC. I didn't go to demo day. I had enough connections and enough momentum to not have to go and do that.

And I only, I mean, there's only one hate comment on Twitter, which is pretty good. A lot of the social media platforms, but this person was like, how could you possibly raise it? He basically was hating on us for raising a big round without a lot of validation. And I was like, I really get it. Like, I'd been you.

So I'm actually not mad at you for being mad at this. It's just like, there's other stuff you don't see. There's my history. There's the market. There's connections. There's a lot of other things, but it can be so frustrating about fundraising. 

MPD: [00:36:23] Yeah, there's the hater thing is real, uh, I think in all communities, but it's also real in the tech community and I get it.

I think, uh, jealousy is rampant. Um, I think it's good for everyone on all sides of this to have a dose of humility, because there is, as you said so much luck and so much challenge that terrific people don't make it. And you know, people who maybe shouldn't make it do there's a lottery. Yeah, but it's not about us.

And it's actually not about our money. It's about, you know, building a better society. And that's the thing that the machine is very good at. It's not good at solving fair individuals. 

Darius Monsef: [00:37:01] No, I would hope. I mean, this is a very value aligned for us. Like our series a I'm very happy that we had a lead in city light, which has an impact sort of focused fund.

We are clearly a for-profit I'm trying to build a big successful business, but I w I don't want to do it at the expense. Of delivering great care. And I think in some ways, maybe healthcare shouldn't be for profit. You know, there's a very slippery slope to compromising the quality of care for business metrics and, you know, pushing people through a funnel.

We wrote a healthcare pledge to match my providers that piss gates, the Hippocratic oath or physicians pledge. We, we have one as a company that mirrors that like my provider. Committed to this, like why run the business? I can actively sabotage your abilities by doing things that I really shouldn't be doing.

So we really wanted to commit to this. I think I can build a hugely successful, very valuable company without compromising on those things. It might mean extra turns of the entrepreneur creative thinking wheel to figure out how we can still make the margins and the profits while delivering great care.

Um, but it was important for us to commit to that. Um, and so. Again, maybe it's the position of having previous exits and then getting to taste still on happiness or pain. Even through that as like, man, I really am fortunate and I want to try and provide access to the same things. My kids, every kid deserves that again, regardless of who their parents are.


MPD: [00:38:25] let's rewind for a second. You mentioned you had a lot of success raising the round out of YC the second time, but you also told me earlier, it was very stressful. Can you tell us a little bit about tattoo therapy? 

Darius Monsef: [00:38:38] Yes. Uh, I, I do have a therapist and a coach thing. Everybody should invest in their brain as much as their bodies as well.

Um, and so there's probably a healthier way to manage this, but yeah. I've gotten good. I think this has maybe six or seven seed round that I've raised now. There's a lot more in the pre-seed seed, post seed, all of that. And so I have a process I'm pretty good at running them. Um, and because of all the momentum had been in YC, I had like a packed funnel is all what you want.

I would, this was summertime. So we'd gone back to Hawaii to be with family. And I was doing YCS bachelor. I was flying back and forth and I had an incredibly busy day meetings. I took some of them zoom. Some of them in person it's like all the, you want all this hype energy. And the last meeting of the day before I headed the airport, he said, Hey, I'd be really curious if you can model this scenario out.

And so on the plane ride home, I started modeling, but in startups, it's all assumptions when you start and he wanted an assumption. Two assumptions down the line and I was modeling it and then it got to a point where it hit me so hard. I literally almost passed out. Like, I, I, I felt the like eyes going inward because I ran through this.

Am I lying. And is this not real? Like I on a good stellar retailer. So I might telling myself a story because I have all these assumptions and then he wanted all these ones that were added onto it. And I, it was so much pressure and anxiety was this like acute whole, I think I'm gonna pass out. I ended up sort of being able to tell myself, although it was hard to truly believe it.

If I'm not supposed to, to know the answer to it. I know the building blocks. I know what we could do. I have a vision for where it could go. But there's a lot of unknowns along the way. That's the whole point of a startup sort of checking boxes on assumptions. And so I have a friend, uh, back in Hawaii who I have an arm tattoo, um, in Hawaiian iconography.

And I basically just said, Hey, I need like five hours because I don't know the healthy way to process this, a stress and anxiety that I have. So if I could just be in pain for five hours and pull my brain away from it, then at least it would be something that might help me. Um, and it did. And in my whole, maybe.

The last round. I didn't need to do it, but my entire arm is covered. So maybe in my career, my whole body will be covered at some point. Well, hopefully 

MPD: [00:41:00] it's not that stressful going forward. Yeah. It is a challenge because you don't want to lose people's money. You don't want to lie to people, but you also are hopeful and optimistic and you know what you're chasing.

And so bridging between those two realities, it's very 

Darius Monsef: [00:41:13] challenge. Okay. Well, I think also there's an assumption that, you know, we celebrate fundraising rounds and it's good. That's fine. It's nice to do this, but we, you know, sort of joked it's I just, it's not my money. I got a massive credit card. I have a, I have a responsibility to use this money to do something with it.

So we also, I get this feedback from my wife. I'm needing to stop and pause and celebrate and. It's hard for me because I, I see where we're going and what I'm trying to do. And again, for better or worse, it's hard for me to celebrate anything because I don't want to feel that like I'm there yet. I'm trying to be irrational high expectations of myself and what I'm trying to do, what therapy and coaching has helped me do is they short circuit, the negative.

Time that I spend sort of stuck in a, well, I'm not there yet. It's like, well, of course I'm not there yet. I'm never going to be able to, to get there. I don't want to lower my bar. I want to, I maintain it, but I just want to find some way to get out of that and go, okay, cool. Well, here's the things you've done well, and let's move forward.

And so, you know, we, I didn't celebrate the a, because I got stuff to do with the EA. I mean, we had a nice piece of chocolate cake. It's a very good job cake, but it was like fine. Now let's move on. 

MPD: [00:42:23] I love that. Uh, one of my, um, good friends recently taught me the phrase post economic and what he means by that is the moment when you've made enough money where your decisions are not all wrapped around optimizing for economic outcomes.

Um, when you had that moment where you became post economic, how did it change you as an entrepreneur? How you think about entrepreneurship, your motivations. 

Darius Monsef: [00:42:51] For me at least. Uh, and I wrote a blog post about this once with actually about like founder suicide. Cause unfortunately there was a period of the early 2014, so there's kind of, back-to-back um, really unfortunate events with founders and one of the hard things.

You can't even confide often and the people who are closest to you of how hard it is, because they would any same person who loved you would like tell you to stop doing it sounds terrible. And I wouldn't want to confide in my founders, they're trusting me to lead. And so it can feel very isolating and very alone.

And so the blog posts is if you're ever alone, like there are other people who are here for you and don't ever consider that, uh, that other option. Um, but you know, I want it. Do something that wasn't just for me, I'm the youngest of seven siblings. I'm generally the one that was most entrepreneurial, I think fortunately growing up in Hawaii and having a sense of community and connectedness to people was a good balance of my mom, the hippie Montessori educator, my dad, very egotistical, you know, capitalist.

I got a good balance there. And so. Mostly what changed for me is like, okay, I have enough, but my siblings don't yet. They're still working hard. My community still working hard. There's a lot of people who will never have my privileges. So what can I do to give back to them, um, whose I'm going to forget who it's from.

But there's a quote. You can never go broke by giving basically you never go poor by giving I, I want more money to give it all away. Um, basically, and there was inch, I think it was when Chris ACA and I had talked a number of years ago through IC it's a conversation, right? The quality of life difference when you have $50,000 in debt to no debt.

I mean, this is a life-changing change to not feel the burden of that debt. Just to be neutral, to have 50,000 in savings versus zero again, life-changing because you have resources, even ability to do something now. And then I think you feel it again, 50,000 to 500,500,000 to 5 million. And then it just becomes less of a big difference.

Like we got two homes instead of one, or I fly first or private sometimes like. I don't care to have a wealth north of $10 million. Um, you know, 10 million is enough to sustain my family and, and downloads for my kids and all this stuff. I really would give the rest of it away. Um, and there's so many areas in communities that obviously can need it.

And this is where. The other thing I did for a number of years was co-founded a nonprofit that set up and run volunteer centers in disaster areas. I enjoyed that work cause it was very similar to startups. It's like literally a problem every single day. If you're living in a community that just was wiped out by a mudslide or a tsunami or a hurricane living in that community, what do you really need today?

How do I problem solve with the resources that I have to do the best job to help you rebuild and get back? Um, I'm wired to do want to do both of those things, but to do it in the biggest way possible. And is 

MPD: [00:45:40] that non-profit still active? 

Darius Monsef: [00:45:42] Yeah. So I was fortunate to help be a part of, so finding that hans.org is the website.

Obviously COVID impacted a ton of volunteer work, but previous to COVID was, uh, you know, maybe a dozen active projects around the world, tens of thousands of volunteers that have come through. I'm very proud of obviously having helped be a part of that story. And you mentioned 

MPD: [00:46:03] there's a couple nonprofits you've been involved with was there?

Darius Monsef: [00:46:06] Yeah. The other one is called . I know Chi means to be C weathered or to weather, the storms of life, which feels very apt for startups. Um, and so I was lucky in that I went to a private school growing up. I, my dad could buy me a computer when I was a kid. And because of the ego of my father, I was told every day that I was special and then I was a worth.

And then because of that, I think you look for it because you assume it to be true, sort of the. The manifest destiny kind of. And so I started a nonprofit in Hawaii too. Right now it runs a summer camp at 20 to 40 kids a summer where we get them from around the state. And we give them 10 days of that, where I buy every single kid, a laptop, they have the same Mac book that I have.

So like you're unlimitless they wear the Nalo. K t-shirt. And so you don't know once the kids get to camp, Who comes from a private school or who comes to public school, they all earn their spot there. And often the same thing I felt being in the most isolated island chain in the world, and then isolated from each other on different islands.

And then even on the big island, I'm 90 miles away from a major town. I was, you're just friends with whomever versus we hear this from the kids in camp a lot is I never met somebody else. Like me just thinks a bit different and just really had this creative entrepreneurial drive in them. So we just want to nurture that in the next generation of kids and especially in the community that feel so disconnected from it to give back to the same place I grew up with matters a lot to me as well 

MPD: [00:47:25] is the hope to build an entrepreneurial community in Hawaii or it's to empower people to take on more, more challenging goals.

What, what is, what's the goal? 

Darius Monsef: [00:47:35] It's a bit of both, because I don't want to ruin what makes Hawaii so special. And I think often we there's been an influx of a lot of, uh, people moving from tech or centers into Hawaii this year because I haven't vacation there and this was the year they could work remotely, but I would hope everybody comes with the, you came there because it is so beautiful and so special and so precious.

Don't make it what you want it to be, that you're going to come in again. This is our nature. We want things to be, and it should change. We could, uh, I just drove to the airport cause we I'm in Portland. It's my first post COVID trip. The lower highway is closed. It was actually a 40 minutes for me to round trip around and I'm going, my brain is going, like, why is there not a police officer, two intersections back to read around people?

And it's like, there's these things that are frustrating there. And that's why it's like, it's Hawaii self-protective mechanism. It will try and maintain why it's special because it shouldn't be as efficient as everywhere else. Let's stop trying to make it something and let it be what it is. But by trying to invest in the next generation, and there's a mixture in this camp.

Teaching and sharing Hawaiian cultural values as well as entrepreneurship and creative, like, well, really it's just solving problems. So Hawaii has its own set of problems. You know, how do we diversify the economic industries there? How do we become less dependent on. Basically anything else. We have the most opportunities for neural energy in Hawaii, and we still import millions of bear  and it just like, there's so much that could be improved in there.

And so by investing all the way back in the kids who are going to spend more time and give to that community, they'll have hopefully successes and then come back. So rather than feeling like we import it, let's just go, it's a little bit more of a long-term view, but how do I invest into it today? So that there's a value for them.

MPD: [00:49:21] That's fascinating. That's fascinating. Uh, I wanna move through here. We're coming up towards the end. Um, you've started you're on your fourth venture back company. There's not a lot of people who can say that. Can you share learnings you had through each venture? I mean, they've probably evolved. You have maybe some insights from each one.

If you can think back that far. 

Darius Monsef: [00:49:43] Yeah, I think the first ones, again, that would be 15 years ago. I didn't know a lot. Um, also so much has changed since then. I, when I was sole engineer designer, I did everything back then. Uh, the ability to deploy things so much faster now, um, maybe as both good and bad and that, because it was so easy, less of a barrier to get started.

I think every generation of every community had said something to the effect of like, Well, it was different when I was whatever, as if it was better previously. So when I had to FDP up my code and I couldn't deploy automatically, like, so it's easier now, but it means it might be more things get started, but how do we focus that on the best things possible?

Um, I unintentionally ended up in design companies for a long time. I liked design. I care about it. I would brave care. I love it. You know, I love kids genuinely. Um, I normal zoom backgrounds, all my kids' artwork. I'm on the board of the Montessori school. In my spare time, I have cars play, which is a, uh, That looks like lightning McQueen from the Pixar movies I could do.

Make-A-Wish things that's also doing. COVID acquired a Batmobile and a bat suit, so I can actually interact with kids as well. So those are the, how I choose to spend my personal time. So being able to, I guess maybe one major thing was getting closer to who I really want to be and how I want to impact.

And starting to start up and the financial returns, I think before it was just like I happened into something and it was probably again, early twenties, not having any money, really focused on myself. Now I'm getting to shift to, well, how can I still do that? Clearly, it'd be nice to make more money, but how do I do it in a way that really gives different value to the world and into the community in which we're serving.

MPD: [00:51:24] I direct you a little bit on this. Could you, could you give us for the entrepreneurs listening? A couple of tidbits, things that maybe are off the beaten path, knowledge. That you've, you've found along the way, things that people just need to know, like do this, don't do that action items. 

Darius Monsef: [00:51:42] The one, I guess it would be a little bit more philosophical, but I think is still really important because culture is super important in startups is how you convince people to join you.

It's how you retain the talent. Hopefully it's building something longterm. And one of the lessons I learned, uh, might have been Don Hutchinson. Who's an angel. Um, In the bay area that had given me this lesson, but it was, we were building this family culture or a family, and I want everybody to feel like it it's like, that's really not what we are.

Um, I think in some cases you don't fire your family. Some people probably should. They got toxic relationships. What we've evolved to brave care, which feels a lot better is where the women's world cup team. We're trying to be the best at what we do. And when the ultimate goal in an environment where everybody else there has earned a spot.

So I. Trust them I'm empathetic to their skill, but I can also provide some critical feedback because if somebody's standing off sides and they don't see it, I'm a shout at them to tell them quickly they're off size. I'm not critiquing your skill or your experience. You just didn't see something that I saw.

So were they brave care invested heavily in our leadership and communication and the culture? We have a full-time coach inside the company to help people provide critical feedback and in a way, yeah. It's been a very big topic of discussion recently, whether or not startups should have any political or ethical or moral decisions in that.

Um, I don't think we can do what we do and build better healthcare outcomes for all kids. If we created an environment where that wasn't accepted or tolerated, uh, just because there are systemic things that prevent kids of color. Yeah. Other communities from getting access to really high quality healthcare.

So it's important. We have a supportive environment where we can talk about hard things. So that we can make healthcare equal across all different kids. Um, and so I think investing into that culture earlier, anything that you do early, yeah. John just will be perpetuated. So cultural things you put in place, I wrote mission and values and guiding principles, things that I wanted to be true because you'll hire people around those.

And then again, sort of like-minds acquire other like-minds. We're 70 plus women in brave care. It's 50 plus employees. Um, we're not quite to the cultural representation. I want to fully represent our, our customer base, but I'm proud of the work we've done while acknowledging there's more work to be done.

Um, so I think the Mo the, maybe the non obvious thing there is. You're making so many in the moment, decisions, it it's worth a pause to go, how much will this become a pattern and then continue forever. And so every little thing you do as building the, you know, further rut in the path that you're going to continue to walk or building the muscle memory.

So some you just need to do because you have to do them, but what are the ones that you really don't want to get in the bad behavior of and, 

MPD: [00:54:23] and, you know, on specific things not to get in bad behavior of. 

Darius Monsef: [00:54:29] Not allowing a space for people to give you criticism as the founder and CEO of a company. Um, I, I have a vision.

Uh, you know, uh, maybe it's like a democratic dictatorship, something like I need to be able to make long-term visionary decisions and not get everybody to literally provide input on it. But I also want to see where I have weaknesses and blind spots. I exist in a very narrow lens of the world and the experiences people have.

So, um, I think it's important to create an environment where you can hear criticism and use it to inform your intuition and then to go from there. 

MPD: [00:55:04] And to shift gears here for a second. Last question for you, where do you see yourself in 10 years? 

Darius Monsef: [00:55:12] It's interesting because as a founder and especially having been through Microsoft and Autodesk's more bureaucratic thing.

There was a, there's a loop, an audio soundbite. I would play this like, well, I don't wanna, I don't wanna run brave care 10 years from now, once it's like thousands of employees, like, that's not me. I'm an early stage person. I like the creative, all these things. And a coach of mine was like, you know, you're creating the company, right?

Like, why are you creating one? You don't want to be at in 10 years, I was like, oh, Right. Like w why, why is the default assumption? I have to build something unpleasant to work at, or not an environment where I can still be creative and feel connected to the things that I'm building. Um, so I think that has shifted like, right, this actually can become my legacy.

I think again, deeply care about kids. Um, brave care is focused on healthcare right now because you know, the foundation of every kid reaching their potential as their health. There are related things to be supportive, diet, nutrition, exercise, even apparel toys. Those are all things that, especially in young kids, the toy you play with develops your motor skill that helps you.

So brave care has won. The challenge of opening several hundred clinics in the country will be enough of a challenge over the next 10 years. But given that I deeply care about children. There's a number of things and maybe I'm more running our philanthropic, uh, education kids book department, someday.

Like it will be something that I can connect you do. Um, so 10 years from now, uh, very sad thought about how old my kid will be. One of them will be out of the house, which will be a change for me, but still focused very much on helping kids reach their potential. 

MPD: [00:56:46] Doris, thank you for the work you do.

Thanks for taking the time to be on the show today. Appreciate you. Thank you.

Big. Thanks to Doris for joining us on the pod to today, he really opened up about his entrepreneurial journey. I thought that was very real. I love what he's all about, and I'm very excited. As you might imagine to watch brave care, continue to crush it I'll be rooting for all of them. If you like what you heard, please look us up with a like, or a five-star review and feel free to share with a friend.

You can find me on Twitter at MPD. And to hear more of my conversations with innovators, subscribe on YouTube, Facebook, or any other major podcast platform. Just search for innovation with Mark Peter Davis.