Insuring the modern nomad: A conversation with Brett Estep

Insuring the modern nomad: A conversation with Brett Estep

Full Transcript (in beta)

Curtis Duggan: Hey everybody. Welcome back to another episode of Remotely Sirius. I'm here with Brett Estep. You're the, I think I saw... was it co-founder, president? And COO of Insured Nomads. Is that correct? I'm indeed, indeed. That's, that's me stalking on LinkedIn. I didn't just know that I, I stalked, I got it from LinkedIn, but that's correct.

Curtis Duggan: In in terms of your...

Brett Estep: It is indeed, yeah. And good to be on your show and congrats on the success here at Remotely Serious.

Curtis Duggan: I remember I was, so, I had an exit in early 2020. I sold a company February, 2020 and that kicked off a whole journey about what I was gonna do next.

Curtis Duggan: And so — long story short — I got into blogging and talking about remote work and what was going on with covid and remote work and digital nomads and all that kind of stuff. And one of the first ever brands or companies that I encountered when I decided I had been in, I had been in healthcare before, so I kind of actually knew a little bit about the insurance space I was in.

I sold a company that sold into enterprise. Healthcare, risk-bearing payers, et cetera, et cetera, in the US. But anyway, Insured Nomads was one of the first brands I ran into an enterprise grade company in the remote work in digital nomad space. This is early. Mid-2020, getting going into early 2021.

And then one of the first in-person events I ever went to, I met Andrew Jernigan of Insured Nomads. And so it was one of the first relationships I ever built. But this is really the first time you and I are getting a chance to talk, so it'll be great to talk about it. Insured nomads and remote work writ large and other things related to, you know, fast forward to 2023.

So Brett, thanks again for, for jumping on.

Brett Estep: Oh, all thanks to you, Curtis. Good to be with you.

Curtis Duggan: Maybe let's just jump right into your company and what's in the name and sort of make that a way of getting into an introduction. "Insured Nomads". Stepping back, I think most of the audience that listens to this podcast understands that there's the concept of a digital nomad, but I'll define it anyway in my own words.

And then maybe you can talk a little bit about your target market. I imagine that there are digital nomads who might have health insurance in Canada with a province or in with the the NHS if you're in England or with various public and private insurers in the US if you're American. And then if you're a digital nomad, you might be working in Croatia or Bali or Costa Rica and you realize like — hey — does my health insurance work there?

I don't just want the travel insurance I get for emergencies. I'm going to Bali for six months. I'm going to Croatia for four months. I need some kind of health insurance. Then you go online and you find something called Insured Nomads and maybe you buy health insurance that's really, really applicable to a digital nomad.

But we were talking off mic before we started, and maybe that was that, that is sort of the genesis of a market. But you're also a company that works in enterprise markets as well. So I'm curious, you know, what is insured nomads in 2023 and, and who are you selling to and, and, and what is your product in, in general?

Brett Estep: Yeah, great question. And in 2023 we're far different than, you know, when we started the company back in 2019. And honestly, it was just a few months before the world shut down. So the timing wasn't we didn't stick the landing on that one, but we had no way of knowing. And we have done a tremendous amount of, you know, product and support evolution in, you know, these, the subsequent, you know, four years essentially is what it's been.
Brett Estep: When we first started the company, it was really predominantly geared towards the, you know, consumer. And we were offering both short-term and term you know, insurance products and services almost exclusively to the digital nomad, the location independent, the remote worker There's a number of us that have backgrounds from, you know, either big insurance or group you know, benefits you know, prior roles.
Brett Estep: And it's in those networks that then came to us and said, Hey, we're interested in what you're doing on the direct to consumer side. Can you. You know, make those products and services available for our group clients. And so, mid 2023, it was in April, we finally launched some new plans that are longer term use case health insurance plans that cater to the enterprise segment.
Brett Estep: We're really focused on, you know, kind of the small to mid market employers at this point that then come with all of the, you know technology and safety and security, medical and non-medical, and we can do. Both cross border and local national risk under one policy. So those are the newer plans which really reflect the evolution of the company.
Brett Estep: If I had to share with you a superpower that we had as a brand, I would tell you that it's our technology and our customer experience. So much of what we have tried to incorporate into the underlying offering. Reflects the antithesis of what you may find available in legacy insurance markets.
Brett Estep: And that's because, you know, we started you know, we put this in the cloud initially. We have leveraged both large language models and the original artificial intelligence. Concepts in the backend of what we do. And so we wanted to introduce features and value that was relevant to the communities and, and the audiences that we support and, you know, bring in technology that everybody is accustomed to.
Brett Estep: Engaging with today that just hasn't, nor will it exist in, you know, kind of the legacy insurance markets. And I won't bore you with why I don't think that will happen. But that really is, you know, kind of our unique advantage in, in this market. I.
Curtis Duggan: So let's, let's break this down a little bit, even for my own edification.
Curtis Duggan: When we talk about, okay, so you learned there's this need out there in initially selling to digital nomads who realized there's not quite the right health insurance product for them, and insured nomads can come and fill that void. As, as many businesses do you identify that there's a, there's a bigger, better, or different opportunity in selling to enterprise.
Curtis Duggan: When, when I think about this, does that mean when I think of digital nomads, they can be from anywhere and you might have been able to and will be able to sell to them if, if they're from anywhere. In terms of nationality, oh, your uk, Canada, American, Brazilian, you're going to Europe, you're going to Asia.
Curtis Duggan: The, the branding was, you know, go anywhere, get health insurance. And maybe there are some, you know, unique wrinkles about the United States. But generally it was like that. When you talk about selling plans to Enterprise, does that mean there's an Amer a US focus? Because when I think of a US company in my experience, they're, they're.
Curtis Duggan: Managing things like health insurance. They're thinking about health insurance plans, all the kind of stuff that is part of, one of the, if not the biggest industry in the us, the healthcare industry. Whereas if I think of a big employer in the UK and you say, we're gonna sell you an insurance plan for your employees, it's a little bit more like, oh, well, the n h s handles that.
Curtis Duggan: We don't, you know, we're not Americans, we don't, we're not an American company. We don't handle that. What does it mean to shift to enterprise? And does that mean. Am am am I correct in assuming that means a US focus even more so, or, or, or am I totally off, off base on that and it's, you know, it's for everyone all around the world?
Curtis Duggan: No, I mean, it's,
Brett Estep: it's more the latter, but let me kind of talk through that because I think it is very nuanced. When we approach the enterprise market, we do so almost exclusively through channel partners, which is intermediaries, brokers and consultants that represent those clients. But. To purchase something like medical insurance.
Brett Estep: You are absolutely correct in that it is a notion that makes a lot more sense in the states because of state provided medical insurance in other countries all over the world. But what's interesting is that we did not initially start our go-to-market with these plans in the Americas. We were seeing far more opportunities coming out of APAC and AMEA and Africa which I know is part of amea.
Brett Estep: But we've got a lot of opportunities in Africa and I think a lot of that is a byproduct of. Some of the you know, turmoil in the legacy insurance markets with, you know, big companies, divesting pieces and pulling away from certain, you know sectors of the market. It's, it's created an opportunity for our brand to really flourish.
Brett Estep: But one of the differentiators for us that allows us to continue to have these global conversations is that we may deal with a, an employer that has a hybrid workforce that may have, you know, outbound US risk. But they may also have, you know, pockets of local nationals in Singapore or you know, the UK that our products and services will support under that same umbrella.
Brett Estep: And up until this point, you would otherwise have to, you know, come up with some sort of patchwork arrangement, but then the value that's extended to all of our members, Are the things that we have curated that go into the native app that is in iOS and Google Play that provide them support services for all things medical, including all things non-medical.
Brett Estep: So geopolitical, civil unrest you know, natural disaster, et cetera. And then airport lounge, access and cybersecurity, you know, protection because our communities tend to want good views. Low, low cost good wifi. And so we try to, you know, package up all of these features that really cater to, to those audiences.
Brett Estep: But, you know back to your question we have, I. Really moved into a pretty comprehensive go-to-market strategy for the Americas to address, you know, the point that you had just made. Which is there is a large market of corporate employers in the Americas. But I would qualify that to say I.
Brett Estep: There's still plenty of opportunities outside of this country too.
Curtis Duggan: Got it. So a couple things I, I picked up on there. One is it's not just health and travel insurance. You mentioned in collection or an umbrella of things including political unrest, travel interruption, airport lounges, not, not even necessarily insurance for bad things happening, but mm-hmm.
Curtis Duggan: Some of the perks, the halo of perks, like the airport lounges is, is an important part of it. And, and you also mentioned you say you're, you're, you're mostly or exclusively through channel partners. So does that mean you're predominantly focused on, and I don't know exactly which ones, but like the Mercers or the Aon Hewitts or the Towers Watsons of the world.
Curtis Duggan: That's, that's the, the prime way that you get in front of your, I. Intended buyers for, for your enterprise tier or your enterprise product?
Brett Estep: A hundred percent, yeah. And there's a, you know, small percentage of, you know, direct relationships that we have with employers. But I would say, you know by and large it's coming through.
Brett Estep: The names that you had just mentioned, I. Got it.
Curtis Duggan: So maybe taking, taking a step back, I think first of all, this is really great for all of our listeners like this, this kind of thing is just gonna become more and more important for people and for, for companies that are managing international workforces and remote first and hybrid workforces, just in terms of the product and what you actually.
Curtis Duggan: R as an entity, as an a company or, and as a company, if you have the pitch, which is, you know, whether the distribution is from a B two C customer or a company giving it to 500 employees or 5,000 employees, the pitch for the product is you can go to many multiple, if not over 150 countries in the world, you can relocate.
Curtis Duggan: I won't say often, but you could move. My understanding is you could be six months in Singapore and then three months in the UK and then one month on site in Canada and. There's a global health insurance product that's robust and not just the thin layer of travel emergency, but it's health insurance plus all the other things you mentioned.
Curtis Duggan: Mm-hmm. How do you do that? How do you have like it's, I've known health insurance companies in the US that are saying we can never expand beyond the US 'cause it's, you know, we're gonna be here. We've been here for decades and expanding would be hard. Insurance feels like something. There are Glo of course there are global insurance brands.
Curtis Duggan: But it feels like something for a relatively new startup. I know you've been around for a while. Mm-hmm. Global coverage, that sounds like a a a, an amazing, it's an amazing pitch and it's an amazing product, but how do you actually get that done from a. Contractual level are, you know, what, what kinds of partners do you have to work with in order to deliver this almost magic wand of global coverage, if I can, if I can use that term.
Brett Estep: Yeah. Another great question. So we believe that and, and we're seeing it day in, day out this, this idea of being remote. This concept of, you know, never ending mobility I think existed pre 2020, but really has since so much attention was put on a couple key things, people being stuck and not being able to travel or go anywhere and their lives being.
Brett Estep: Largely disrupted, you know, either from a, you know, health perspective, an economic perspective, a community perspective. And so you have this whipsaw effect of people coming out of the past two, three years that now are, you know, committed to being global and, and global citizens. And so how, how we accomplish that.
Brett Estep: We've designed all the insurance products. I mean, insurance largely has a bad wrap. Either people buy it and they don't use it, they don't buy it, and they regret it 'cause they need it. Then when you try to engage with an insurance brand, the, you know, service component is beyond subpar. And you know, there there's this idea that you have to, you know, pay, pay with your own money and collect some foreign paperwork and send it to somebody and, and cross your fingers that all of it isn't denied, you know, in two months time.
Brett Estep: It's, it's those friction points that we know exist. How to find healthcare and how to finance healthcare. So we've incorporated things in the insurance products to address that. Think TripAdvisor as opposed to just an alphabetized list. Think FinTech integrations with our MasterCard pay card so that you get the digital money that's integrated with your digital wallet, which is how people, I, I go to concerts and I go to, you know, travel, everything is incorporated with my digital wallet down to my, you know, coffee rewards card.
Brett Estep: And, and so why? Should insurance be any different? So in, in terms of the geeky structure of the business, Curtis, we operate as A M G U or an M G A, and we either build things internally. You know, like, you know, some of the tech components or we establish partnerships with companies like Bitdefender who provides our cybersecurity protection because it's an important value delivery, but we have no interest in, in becoming a cybersecurity company.
Brett Estep: So we just partner with some of the industries best to, to make those available in, you know, either a white labeled or a co-branded fashion. And we source Insurance capacity from different companies. But we handle all that on the back end. So the employer never has to handle any of that on the front end.
Brett Estep: Come to us, identify the specific needs, the geographies, the number of belly buttons, what type of plan value you're looking to, you know, in terms of the design. And we bring all that back to you you know, and execute a single agreement to, to get that done.
Curtis Duggan: One of the things that, that's really, that's really helpful, you know, it, it mirrors You know, a lot of successful FinTech companies have, have come in and done that.
Curtis Duggan: You know, there's an element of underwriting your own risk, but it's also about being a router and finding the right partners to deliver the underwriting of the risk and deliver all of these specialty niche things like the CY Cybersecurity. So, so that makes sense. I, I'm curious actually. In terms of the actual, you know, your, your customers and then your company.
Curtis Duggan: Is, is insured nomads fully remote or are you hybrid? What's, what's kind of, do you, what's it like to be an insured nomads? Is everybody a nomad that's somewhere or do you have, you know, an office? I know that I think there was a nominal connection to Alabama, if I have that right. I don't actually, I, I remember there being an address there when I was signing some document or something.
Curtis Duggan: So I'm just curious what the. What the philosophy of your company is internally around this whole world that you sell into.
Brett Estep: Yeah, I mean, it's, it's really a, a mixed bag as we kind of process this. So to answer your question directly, we are fully remote. We do have a corporate HQ that is in Birmingham, Alabama, which is where all of our governance and documents and things are, you know, executed.
Brett Estep: But and that's because my business partner and co-founder Andrew has ties to Birmingham, Alabama through school and otherwise. And But yeah, we, we strongly encourage people, all of our employees that are all over the world to you know, travel and, and live the lifestyle that we support.
Brett Estep: We find more and more applicants coming into the talent pipeline simply because they know that I. Especially the younger generation has a tremendous desire to, you know, travel and work and combine those two things you know, for the betterment of experiences or cultural immersion or, you know, whatever their desire is.
Brett Estep: But we have been fully remote from the, from the start. We are. Considering looking at the fourth quarter of this year, getting an all employee meeting probably somewhere between Koala, Lampur Thailand, someplace in, in the east. You know, but we have had to, and, and one of the things that I'll tell people all the time which is we're trying to create a best practice employer as a fully remote business and all the challenges that come with being a remote business And, and I think we're doing a pretty effective job at it.
Brett Estep: And I, I would never envision, I've never been to our corporate headquarters in four years. I don't know if I will ever go if that speaks to our commitment to being remote. Where are you based? I'm currently in the Midwest in St. Louis, Missouri.
Curtis Duggan: Oh, great. Great. Yeah. I see that. Right about now? No, we're recording in the summer or dog days of summer of 2023.
Curtis Duggan: The current mood, it might just be aspects of the media, but I think there is some, there's some substance to the fact that there's a mood around many leaders and thinkers in. Fortune 50 companies, Silicon Valley a little bit, and then maybe even in the long, longer tail of medium-sized companies as they face a recession, as covid is really quite in the rear view mirror in terms of an immediate risk and the immediate risk of lockdowns.
Curtis Duggan: There is this feeling that many leaders are saying, okay, we're going back to the office remote didn't work. Hybrid doesn't really work. We're gonna negotiate. We might even go back on something we said about being remote forever. I hear it from, you know, Amazon's doing it, others are doing it. What's your, what's your take kind of from speaking to your prospects and your current customers around?
Curtis Duggan: What's happening with, especially as you think about the enterprise, is that just a nice headline that one, c e o said, Hey, we're going back to the office, so all of a sudden there's a trend. How do you see the the long-term trend of more and more remote with this kind of short-term FUD around maybe we're all going back to the office.
Curtis Duggan: My personal bias, which I'll just say is that I think the long-term trend is towards remote, but I try not to be a zealot about that and. Examine with, you know, an open mind. You know, if there's evidence that there's a trend that maybe it's reverting back to the office, that could, you know, that
Brett Estep: could be true.
Brett Estep: It's funny, I'm finding that, you know, on that specific topic there, there seems to be a tremendous amount of response bias based on, you know, industry or their personal point of view. We're obviously, you know, all in on remote work. We are obviously banking on and assuming that it's here to stay, I.
Brett Estep: I've got a lot of reasons that, that support that. But when I talk about this bias, it's like if I'm visiting with somebody that's from a more traditional industry, whether it's, you know, finance or accounting or consulting you know, they, they seem to be the ones beating the drum to return to, you know, on-premise work.
Brett Estep: I think there's, you know, pluses and minuses to both. You know, I, I think humans were not designed to, you know, simply sit behind a screen isolated. But there's ways in which we can solve for that as a, as a remote company. The trends that we're seeing is that more remote, more hybrid. I'm constantly visiting with people that at the very least have flexible work schedules and even in industries that, you know, when I was in corporate benefits consulting in the middle of my career, that, you know, it's a very traditional kind of approach on-premise work, you know, in the office visiting with clients, collabing with the team, et cetera.
Brett Estep: But the trends that we continue to see, and I think it's, it is supported by, you know, good data out there. That, you know, whether it's job satisfaction or employee pro productivity. And, and then this ability to, you know, life work balance. You know, I'm, I'm a father, I've got a young family and, and you know, my wife and I work at the house.
Brett Estep: You know, when we're not traveling, I. And it's, it's nice to be able to have that balance which I think so many people that didn't have access to that lifestyle were thrown into it over the past couple years and I think it's gonna be very difficult to pry them back into the office personally.
Brett Estep: And I think with some, some of these brands that I visited with when they said, All right. You know, this is all done. Everybody's coming back to the office. A meaningful percentage of them said, okay, we will leave. And so that's where I think they had to begin to consider, okay, well we don't wanna lose all of our talent because your key talent.
Brett Estep: Let's come up with this hybrid that allows you some of the flexibility, but us to be able to, you know, bring, and the, the other thing for consideration too corporate real estate, you know? Mm-hmm. Outside of the looming macroeconomic stuff and what may happen in corporate or commercial real estate if companies walked away from it, you know, to what extent do they wanna bring that expense back onto, you know, their you know, budgets.
Brett Estep: So,
Curtis Duggan: Yeah. Yeah, the, the macro situation with the, with the commercial real estate, that could be a whole other, other podcast in terms of what'll happen to downtowns, what'll happen to class a office space and all kinds of classes of, of office space. And will people bounce back to the city even as maybe remote workers?
Curtis Duggan: Will they bounce back to the cities and get bored of the, the home office? There's still, still a lot of stuff that remains to me seen, but I almost want to think of it like There's all this, you know, there's all this uncertainty right now, but I'm curious, kind of going back in time a little bit and looking at the present where we, well, where we know what we do know right now, if you know, obviously you believe in this, this trend, this space the, you know, remote work writ large and everything that's gonna happen with remote work I do too.
Curtis Duggan: But if you were to look at. Say go back to 2018 or even 2021 when remote work was accelerating, and then look at now what has been challenging? What? What would you say in two, in the last two or the last four or five or six years hasn't happened as quickly as you thought, or maybe didn't take hold once Covid hit, you think, oh, everybody's gonna know X, Y, Z, or your customers are gonna come running to you.
Curtis Duggan: Like what have been some of the things where it's like, well, we thought this was gonna. Take off, but you know, there's still more education needed for the market or, or maybe certain things aren't happening as quickly. Are there, are there areas where like, you wish, you wish this, the, your cu the enterprise customers would kind of know something that they don't get yet and you wanna grab 'em and say, Hey, You need to get this, you know, or, or, or tell the channel partners to educate them.

Brett Estep: Yeah. I mean, so the brand visibility has been, you know, difficult. Because we haven't had, you know, a massive marketing allocation that allows us to sponsor golf tournaments or Formula One race cars. Yeah. And, and so that's been a challenge for us. The other thing that's been a challenge, and, and we're not unique in this, is, you know, capital markets are super tight and they have been, you know, I think they're looking at some of these, you know, leading indicators of the economy.

And and, and have some hesitation. And so when we were in periods where the organic revenue wasn't happening as, as often or as fast as we would want, you know, as we scale the business, we have to look to, you know, outside money. And you know what, once was a $10 million check is now a $4 million check.

Brett Estep: And what once was 90 day due? Due diligence is 180 days. And so, you know, you're, you're finding You know, nuances in those aspects of the business that simply didn't exist in 2017 or 18. And, you know, honestly into into 19, it wasn't until the, you know overwhelming economic, you know, hardship that most societies and countries dealt with when things were locked down in so uncertain.

Brett Estep: You know, but those, those are two of the key things that I think that and, and I've told people if we would've started the brand in 2012 I think we'd be, you know, well on our way to achieving some of our both mid and long-term goals, both from, you know, acquisition and market share and top line growth.

Brett Estep: But we've just had to deal with some things that I think have been very tough for us and many other businesses as well.

Curtis Duggan: Do you think that would you — there's probably private conversations you have that you can't talk about, but in general, would you say that VCs get this space or is there a, is there a chill on it?

Curtis Duggan: I, I don't mean not because I know they love software. I think that's, that's, you know, most VCs love the scale of software. But of course he, insurance is, is a whole different beast. And it's not, there are VC backed insurance companies, but it's a little bit more of a traditional industry. And so, What's your take on how the VCs see remote work as the, the a trigger or an inflection point, like the kind that they like to look for and do, do VCs get insurance?

Curtis Duggan: Do they understand the model and in your model or, or? Or what don't they get if they, if they should get it better?

Brett Estep: Some do, some don't. The ones that don't maybe they just don't have an emphasis on, you know, this industry or this sector. Some that don't get it will bring in experts that they have on their team that understand and can take, you know, the deep dive into the insurance.

By and large, I think most of them have gotten it. And you know, if they have certain questions, you know, part, part of. What we have to solve for as a business is that, you know, the, there's a good bit of diversity in our products and services, and we can cover a, a broad range of things. Oftentimes in early stage companies, these guys and gals wanna see, you know, some linear focus on you know, a niche business that has product market fit and is converting.

And, you know, we've got, we've had time to do. You know, evolutionary work on our products and services and, and create some of these new go-to-market strategies, you know, vis-a-vis the enterprise stuff that, that we're doing. And, and so I think that has, I. You know, created some question marks where, you know, we've gotten some VCs that say, hold on, you're doing both D2C and B2B work.

We're saying yes, you know, but that was because we were pulled into that based on many of our backgrounds coming from kind of that group insurance environment. But yeah, I mean, it's by and large they get it and when they don't, there's reasons why.

Curtis Duggan: Got it. So. There are, there are other companies that, you know, maybe one or two other companies like you that emerged in the last decade and specifically say, you know, remote work insurance or Nomad insurance.

There are one or two competitors, I won't say their names. It's a friendly podcast. This isn't hard hitting journalism, but you know, there's a couple ones out there that kind of focus on the same, you know, we're in emerging. Nomad or remote work or sort of the, the hybrid enterprise focused type of insurance.

And then of course there's the world of existing insurance companies. The, the big ones. I don't know exactly, you know, Aetna X or whatever global insurance companies all around the world. Do you see, you know, among, you know, other upstarts, the big insurance companies, and then just. Ignorance and apathy.

Who are your biggest competitors? Do you, do you compete with the other Nomad insurance brands, or do you compete with pulling business off of huge conglomerates that are 150 years old or a hundred years old, or is it really just Blue Ocean where we're just trying to get companies that might not even be doing this for their international employee or employees that are working internationally across borders and kind of.

Pulling them in from the blue ocean of like, this, this isn't even really a thing. How do you think about competition there?

Brett Estep: Yes and yes. The competitive landscape includes both. I would say that more of the competition is coming from the ones that may have nomad or the lifestyle and kind of their name or mission or, you know, purpose.
Brett Estep: Mm-hmm. The larger legacy markets, which many of us have come from, spent our entire careers in, in this industry or this sector are absolutely in our cross hairs. We believe that the, you know, enterprise portfolio of stuff that we can provide, we've gotta make some, you know, important adjustments to align with some of the, you know, specific needs in the US markets.
Brett Estep: But once we finalize that, which is, you know, kind of half two of this year we will look to begin to siphon off share of market from, you know, the, the large insurance companies that have been around forever. It initially wasn't the thinking. It, initially the thinking was focus on this direct to consumer stuff, focus on this digital nomad revolution that's kind of underway.
Brett Estep: I. But for the reasons that I previously stated, I think it makes sense for us to then go ahead and you know, begin to try to acquire some of that available market. And, and I am either ignorant or arrogant in that the value that I think we've created, I. Is far superior than what can be provided or achieved from the legacy insurance markets.
Brett Estep: And we've honestly had conversations with, you know, some of the big insurance providers because I think they want to kind of take a look at what's under the hood. And, and if I step back and say, where does all this go? You know, this is the type of incubator business that I think somebody will watch us doing what we're doing.
Brett Estep: And eventually in seven, eight years, We would then become an acquisition target so they can acquire all of the technology and customer portfolio that we've built. Yeah, something, yeah,
Curtis Duggan: something that plays out quite a bit in, in FinTech and in InsureTech. That's definitely a, a playbook. I. In terms of this, this new focus, what does that mean?
Curtis Duggan: That you have to adjust your, your sales and marketing? So before it might've been, I know obviously like it'd be great to have bigger budgets, et cetera, et cetera, but before, if you're going to digital nomads, it might be ads, it might be, you know, going to trade shows, nomad events, remote, all kind of, all of the direct marketing to nomads.
Curtis Duggan: Do you now have to roll out Salesforce of people that are on commissioning quota and and managing their territory. Do you have to rework that part of your business or is the same kind of marketing functions that you had to market to nomads carry over to the enterprise? Or is that, is there a little bit of.
Curtis Duggan: Digging and reworking to make that work.
Brett Estep: It's, it, it, super cool question. We, we need to, yes, have a business development organization that we have built and we're continuing to build to have individuals get out there and tell the story. We do have some of the, you know, traditional marketing efforts, whether it's, you know, participating in nomad events in other countries, participating in a lot of these remote work, you know, webinars, when.
Brett Estep: You know, the past couple years when everything was virtual, we did a good bit of sponsorship and support for those types of events. But when I made the comment earlier about being kind of a best practice employer, you know, as a remote work, working asynchronously, we're, we're rethinking, you know, the specific collisions in a business development process, leveraging technology.
Brett Estep: How much can we lean into. You know, or you know, a mm-hmm video production or a loom production that allows us to kind of paint the framework, give it to somebody, they can digest it when convenient for them, link with our calendar so they can get time to talk about their customer opportunity.
Brett Estep: You know, with some specific details. Versus losing 90 minutes to two hours in a conference room talking about, you know products and services that, that may or may not fit your client. So it, it's gonna be a combination of things that allow us to leverage current tech. To, because in case you've missed it, people's attention spans seem to have disappeared.
Brett Estep: Mm-hmm. And so we're trying to find the right bit of information to communicate with our audiences, our members, or our consultants, and, and allow them full flexibility to consume it, you know, when it works
Curtis Duggan: for them. I imagine you've, you've. Oh. Well, I shouldn't say I imagine. I know you've, you've tried different things and experimented with r o I, 'cause I just because I see insured nomads as brand sponsoring different things.
Curtis Duggan: I met the insurer nomads team in person in Montreal in 2022 at running remote remote conference. I'm almost just curious for our listeners, one of the things I try and parse and figure out is, In my experience, I almost have two halves in my head. I know on the one side there's this slate of remote worker and nomad events.
Curtis Duggan: Things like running remote, which is business focused, but there's also totally like digital nomad festivals that are almost mm-hmm. A party. And that starts to, you know, stray a little bit from anything that has to do with enterprises. And then that's more just a, a fun party for nomads in Bulgaria or, or somewhere else.
Curtis Duggan: And then on the other hand, I know that there's traditional. InsureTech or insurance conferences like the H I M S S, HIMS and Health. Mm-hmm. In Vegas or you know, there there's any number of dozens of Medicare, Medicaid conferences, pharmacy benefit manager conferences, the consultant conference, the, the channel partner conferences, all kinds of stuff that's very industry specific, has nothing to do with.

Curtis Duggan: Digital nomads wanna wanting to get together for three days and sort of party and attend talks like, and I think running remote is actually kind of something that's in between, it focuses on the enterprise, but digital nomads show up anyway. My, my whole point though is in, in mentioning all of this is are there events that you think are the best, the most well done?

The best fit? Like if you look at. 2024. It's, it's almost for you, but in your experience, but also if there's enterprise leaders listening or there's remote workers listening in terms of like, I see these events, I don't know which ones to go to. Has anything stood out as, oh, that, you know, that that event really nailed it in terms of exactly what you want in terms of the audience, the trade show, my experience is limited.

I've only really been to running remote, but with my. Background as someone who had, you know, I was a CEO of a health tech company, and now I'm thinking about the world of remote working at Digital Nomads. I kind of look at the events and, and I'm trying to figure out like, is there some conference that I'm just not thinking about?

Curtis Duggan: That's the best one. And so I'm, I'm just curious, like what, what's been the best or is there something that you look forward to sponsoring or are looking forward to in 2024 as a. As good ROI or just, you know, an emerging leader in bringing the right people together in this

Brett Estep: space. Yeah. I'll probably talk out of both sides of my mouth on this one for, for good reason.

Brett Estep: And, and I'll start with a negative. I, for years have, have really, and I'm not unique in this you know, kind of line of thinking, but I've, I've really struggled to understand the legitimate r o i in in investing in conferences.

Curtis Duggan: You know, is there — and sorry to interrupt you — but is this like going back decades, like long before remote work?

Curtis Duggan: This is just sort of a principle you've learned over your career
Brett Estep: or specific, and I wouldn't even say it's a principle, but Yes. You're, you're right. This, this goes back, you know, throughout my two and a half decades career. Yeah. You know and when you get closer and closer to. You know, the purse strings where you're having to make investments in some of these events, you know, has, has there ever in my career and I, and I socialize this concern or question with my colleagues and just say, Hey, I know you've been in the industry for 40 years.

You know, what? Say you. So, I, I come at it from a you know, a, a, a thoughtful area because anything that we do right now, whether it's investing our time or our treasure must be done with some efficiency and with some thought. Mm-hmm. Now, having said that if you go to our website, insured, we have an events page.

We are, you know, speaking at a number of various events. We have been sponsors of the worldwide broker network. I'm in talks with the I B N network, that's I B N as in Nancy. You know, for their event coming up in Dublin in October. I'll be in Berlin next month speaking at a conference.

So we. I, I know the Bansko Fest, which is more of the, you know, kind of individuals hanging out and enjoying you know, company and, and discussions. So we're looking at, at many of them to continue to get, you know, our message out. We've been not only sponsors but speakers at running remote especially, you know, during the, you know, two years of, you know, kind of isolation.

But I. So, so I'll, I'll go back to my comment about the r o I. Not only do I have that as just a real question that is not preventing us from investing in these going forward, but then time invested in these things, especially if you are at a virtual conference where you need to sign up. And, and theoretically it's an eight hour day and you're going from virtual room to virtual room and these networking events and going to somebody's you know, booth as it as it was.

I, I just don't know how effective they are. I think if I was to say virtual conference versus in person, I. I would favor the in person minus the, you know, added expense that it comes with. And you know, I, I've been in business development I'm an extroverted guy. I'm, you know, I need to be around people.

And so I tend to favor some of those, but that could just be a personal bias.

Curtis Duggan: Do you like to make use of nomad freedom in the sense of traveling quite a bit? Or is your, is your base in the Midwest and you, and you like to, like to stay there? I'm just, just curious how much of this do you partake in, in terms of global travel on, on, you know, throughout the year?

Brett Estep: I believe in it wholeheartedly. We've got all three of our kids, their passports. We I think just booked some time to live and work in Central America. My business partner Andrew you know, his, his wife is Brazilian. They spend a good part of the year down in Brazil. So fortunately the time zone kind of works.

Brett Estep: We've got the guy that heads up our IT and dev team, he is in the Canary Islands, but he's currently in Germany. You know, we've got One of our business development guys is en route to Eck. We've got a Britt that is our market director that is in, you know, Thailand. I mean, we've got team members in Malaysia.

Brett Estep: So we strongly, strongly encourage people to, you know, do that and, and find a healthy life work balance. And hopefully that includes travel.

Curtis Duggan: The, on that note, this is a little bit of a nerdy question, but kind of in the vein of some of the talks that happen at running remote in places like this. When you have your company that's spread out, everybody believes in the philosophy and leadership supports the philosophy.

Curtis Duggan: Are there specific tools and pieces of software, you know, do you use Teams or Slack or some of the various other. You know there, there's all the, there's always the mention of certain tools can help make ASIN communication work or communication on across time zones. Are there any insider tips that aren't giving away too much of the special sauce on when everybody's spread across the world?

Curtis Duggan: How do you actually, you know, imagine the, the, the, you know, the somewhat conservative person who thinks like, I just can't imagine work getting done unless we're all standing around the whiteboard just getting our energy in the room and. Fixing the problem and being, this is the action, this is how we're gonna, you know, charge this initiative forward.

Curtis Duggan: Oh, someone's in Bali, someone's in Central America. Someone's over here. You know, I, I can imagine if you'd never seen any of the software, you probably would think, oh, that, you would think, oh, there's no way to get work done like that. But I know that there's, there's certain tools that can make all of that a lot easier.

Curtis Duggan: And I'm just curious if you, if there's anything you, anything you recommend, whether it's a tool or just a. A teamwork principle that helps you get stuff done when you're in different places.

Brett Estep: I would tell you a couple things. One, what not to do when we initially started so, so I'm a kind of a tech nerd and I don't mind all the, the computer stuff.

Brett Estep: And so I would collab with my business partner in what. We would affectionately refer to as kind of our omnichannel environment. I mean, we would be, you know, engaging via teams, dms, via LinkedIn, WhatsApp, SMS, email. We did start with a Slack channel back in the day.
And, and there was just, I. And beyond there, there was just too many.
Brett Estep: And while I could effectively manage it, because I know where my notifications are coming in from and I know how to, you know, jump and, and navigate pretty efficiently, it, it really is probably something that should not be done. I. More broadly as, as your team grows. So we've taken that, you know, kind of lesson and really honed in the focus on our platforms.

Brett Estep: And right now there's two key systems that we use. One is Slack and the second is Monday.

Curtis Duggan: Oh, Monday. That's awesome. Well, I, I say that's awesome only because I. In the 2010s. I, the, the company that I, I sold had an exit in managed it a lot from New York City. Mm-hmm. I would always see the Monday ad on the subway and I didn't necessarily hear anybody about anyone using it.

Curtis Duggan: You know, there were all kinds of different project management software, but I just remember, I. There was, there was some time in the bull market of the 2010s where Monday was just doing ads everywhere on the subways in New York City. So it some fond and nostalgia and, sorry to interrupt, but No,

Brett Estep: no, no. I mean, I recall those ads, not specifically in New York, but I mean their, their ads were ubiquitous and, and I remember 'em, and it's just, you know, it's interesting that I found my way here because part of my professional background, I was a, you know, big, big company.
Brett Estep: And so of course, you know, the solution was an enterprise Chicago-based c r m type system that we used. And this one, you know, so, so those are the two primary platforms? Yes. We still engage with email. You know, and if I need to WhatsApp somebody, you know, I can do that. But more broadly as a team, we, we try to focus on that.

Brett Estep: And then we've created, you know, I don't know, dozens of channels in, you know, kind of our Slack environment. But the, the, if you look at how I work and how my wife works, it's, they're, they're fundamentally different. And I, and I think the way that I'm one is not right. I'm just saying I find that there are so many people that now, Can effectively do most of their job via their laptop and in some cases via their smart device, their, their phone.

Brett Estep: Mm-hmm. And systems like that, that were designed with those platforms in mind. To me it's, it's gonna be the way work gets done. I mean, the integrations and the automations that are connected between those two. I mean, slack and Monday, you can go back and forth from either platform. Monday's really well funded and they've got a lot of automations and integrations that have been effective for us.

Brett Estep: And now we're using it as our CRM as well, so,
Curtis Duggan: And, and you, you mentioned that you have, you got iPhone and Android apps, so you have an engineering team. It's not just policies and DocuSign policies and signing new insurance partnerships and specialty partner partnerships.

Curtis Duggan: You're shipping updates to apps and websites and things and have that tech company part of your overall operation.

Brett Estep: Well it's part of what I share with people too is that in a prior life we espoused to be a technology company that we could never generate an accurate invoice, and the invoice seemed to have come from a, you know, 1982 dot-matrix printer.

Yeah. And, and so here since there were no system constraints or limitations on the frontend. When there were ideas that were had that we knew would address a specific need, especially if it was tech organized then we would put it in. And just do it.

Curtis Duggan: On the topic of tech, I might just ask a clichéd question, but a clichéd question nowadays in the sense of I'm not sure if you get asked this a lot, but I'll just ask it and it's:

Does generative AI and the new ChatGPT or OpenAI technologies, LLMs and the various competitors, does any of this latest technology trend that's exploding in popularity, exploding in hype, and maybe reaching a point where we're starting to evaluate, you know:

How real is the hype?

What are the actual applications?

Does any of that trend of the last six to nine months affect your business, or is it essentially a nice tool. Maybe the engineers will use it a little bit, but AI doesn't — Does it necessarily disrupt insurance anytime soon?

Brett Estep: It, we are using it. I have some, you know, moral and ethical question marks in my mind because I'm a man of faith.

But right now, the way in which we're using it is more mid-office to backend. Mm-hmm. It is not, while some of these platforms can replace people because essentially you can feed it everything, everything about your business. Mm-hmm. You know, chat transcripts, policy language, legal documents, benefit designs, you can feed them everything and you could essentially get somebody that doesn't have to go and.

Check a document or a website or a page to get the answer. The answer is instantaneous. And it could be in any format, telephonic, email, or otherwise chats. We use a lot of chats. So yes, I think there, it, it can and will continue to impact this industry. And I worried that it is going to be, you know, a replacement.

No. There are other industries that I would be. More concerned if I was in them that I think AI will decimate

Curtis Duggan: decimate. So you, you do think it will come after some other industries quickly and to the detriment of some in some industries?

Brett Estep: I, yeah. I, I personally do, I feel like tens of millions of jobs will be lost at the expense of artificial intelligence and large language models.

I mean, when I have used it, you, you can go into our app and, you know, we've got an LLM out there that's our travel concierge. I mean, have a conversation with it about any destination you're going to, and it's gonna give you the information back in a second. When we've needed to you, you know, understand and write code create draft legal documents you know, Support our marketing efforts and copyright for website.

I mean, it really, and, and now that you look at some of the ai, you know, videography, you know, where is the place where all of these things converge inside a marketing department? You know, how is it gonna transform agencies like that? How is it gonna transform healthcare? How is it gonna transform legal?

You know, it's only limited by your creativity in terms of where you wanna put it in. And, and I do think it will have, you know, a pretty seismic impact on, on industries.

Curtis Duggan: Got it. So I mean, it sounds like you recognize and are already using it in the sense of we need to interpret this legal document or rephrase this, or, oh, what's this JavaScript function that should go with this CSS?

Mm-hmm. In some frontend web code as a functional tool, it can spit out the function you needed and you know, The intermediate engineer might have taken three hours. This takes three minutes. But you know, so, so on a day-to-day level, there are some use, there's some usefulness, but but you have objections more on like the long-term basis, you know what, whether it's going to take away tens of millions of jobs, how it affects society.

I think that's, it's probably the same same view though that a lot of people have, which is, I found this useful for, this, my recipe, my this or that. But I'm worried about. You know, what the, what the macro picture is if it continues on a, on a certain trend. So, you know, we'll see. You know, I feel like it changes.

I feel like there's a little bit of the hype coming down and Okay, we understand let LLMs, they just kind of spit out what has come before in a new package and maybe the idea that we're on a disaster trend by the end of the year because it's just gonna become a, a smart singularity. Some of that. Hottest take hype has died off a bit.

But I, I do think that people, you know, compounding is something that's hard for people to understand and we don't really know what compounding for the next five years will do to what, you know, our relationship with, with AI is. So it's, it's, it's interesting to get your take from, from the point of view of someone who's implementing it, but has, has some, you know, a few concerns about it.

Brett Estep: I, I, I mean, we're gonna continue to monitor it carefully and, and watch what Yeah. You know, it's, it's application but it's out and you can't put it back. Yeah. And I think that you know, somebody will continue to push it and I hope it's for the continued betterment of, you know, all industries, our industries and society at large.

Curtis Duggan: Well on maybe close to a closing note, and on a more positive note, you mentioned you're going to Central America. If you were just talking to the average, an average family in Chicago or Manchester, England or Toronto, Canada — they've never worked outside of their home country in their lives.

They maybe just found out they work for Deloitte, they work for some company, and they just sat around the dinner table and said, Hey, you know, we can. We can work somewhere else. We could go to Europe, we could go to Asia, we could go to Central America 2024. Maybe even even this coming winter in 2023. If there's people out there looking for places to go, I.

What are you excited about and what's sort of just more on the the light and fluffy topic of what are the hot destinations what are you excited about in terms of workation destinations and places that families or, or, you know, or single people can go? I feel like a lot of the A lot of the recommendations out there are just for young, young single people, you know, 25 year old nomads on nomad lists and all that kind of stuff.

So I also try and like ask around and, and figure out, you know, okay, but what if someone has a, is a young family or, or even people are older, they have, they have kids that have left the home. Like, what are some of the great destinations around the world? For a workation, so like, need the wifi, need the coworking space.

But a fun place to go. You, you got anything on the, on the list?

Brett Estep: Yeah. I mean, we're seeing a lot. So from a personal perspective you know, Belize in Central Americas just, it, it takes all the boxes especially for us with the young family and to live and work and time zone and ease of access.

Brett Estep: But, you know, places like Lisbon in Portugal, places like Estonia are super hot — Croatia. And then the number of people that I personally know that have spent a tremendous amount of time in Europe this summer and broadly this year. You know, various places. A a lot of the hotspots, you know, whether it's, Italy and places like that. London.

And then I think the jury's out on Thailand. It used to be such a hotspot. But I'm seeing conflicting stories about what's going on there. But, you know, from, from our perspective ywe, we enjoy being in the sun. The kids enjoy being in the water and the sand. And you know, I've been as far as Bora Bora in the South Pacific and as close as Central America here and even closer still — great places in Florida.

Curtis Duggan: Yeah, I spoke to a representative from Palau in a previous episode, and so there's places now in the South Pacific that I never necessarily pictured myself going to, even in my lifetime that now it feels like at some point I gotta go down there and see what's going on in Micronesia in the South Pacific.

But yeah, Belize is an interesting one. That's a good recommendation. Not necessarily everyone's first recommendation in Central America. People talk about Costa Rica a lot first, and then other countries, but a country with more of a history with English than you might expect, if you imagine everywhere being completely Spanish. is my understanding that it's the official language and has a history as a colony — A British colony. So that's a great recommendation.

Brett Estep: And yeah, so Costa Rica's great too. Don't get me wrong. We've done Costa Rica we just haven't done it with our kids, but, oh yeah. When we were there, we specifically said this is a place that we're gonna bring the family back to.

Brett Estep: So, yeah. What, what

Curtis Duggan: part of Costa Rica is have you been, or your

Brett Estep: Favorite? That was, we were on the western side, so I forget if it's Liberia or. Yeah. Another airport.

Curtis Duggan: Yeah, probably the Liberia airport and then that the, the Guanacaste or Nicoya side, the Pacific Coast. That's great.

But yeah, thanks. Thanks for coming on remotely serious. It's been great to reconnect again with, with you and with insured nomads in general. And we'll, we'll definitely be tracking what you're up to this year and next year and, and we hope everybody will, we'll put. Insured nomads and your info in the show notes as well for people to take a look.

Curtis Duggan: If they've listened to this episode,

Brett Estep: please do. And once this is up, then I will send it out on social media. But Curtis, it was awesome to be with you and I appreciate Your time and, you know, continued success on remotely series. Thanks Brett.