The importance of empathy in leadership, exiting two companies, and maximizing your data with Margeaux Giles (CEO at GoGiles)

Callan Harrington 00:01
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here.

Callan Harrington 00:21
Today, our guest is Margeaux Giles. Margeaux has been an InsurTech vet and an insurance industry veteran as a whole for a while now. She's had a ton of successful businesses. She’s the founder of Go Giles InsurTech Consultants, InsurTech Innovations, Women CEO of the Year, top 20 InsurTech providers of 2022, founding member of Insure Women, Forbes author, and keynote speaker. Margeaux, super impressive resume. Very excited to have you on the show. Welcome. That was a mouthful.

Margeaux Giles 00:57
I can't believe I got it. I can't believe I got it.

Callan Harrington 01:02
When I'm on the spot, and you know when I have this problem—if I have to go in front of a group, I don't mind public speaking, but if I have to write anything on the dry erase board, I can't do it. It's impossible.

Margeaux Giles 01:12
It's impossible. I do. I mix up my note cards constantly. I'm like, “Oh, I hope that was the right order.” I have to memorize it because if I don't, I can't do it. I can't do it. I get lost.

Callan Harrington 01:22
So tell us what you're doing today.

Margeaux Giles 01:25
Well, today I'm preparing for a hurricane in Florida, which is always a hot topic, right? But I’m also working with the insurance agencies that I own and prepping for the hurricane. We’re also prepping for the release of a SaaS product, which is a new venture we’re working on from the consulting firm—releasing a SaaS product for InsurTech on the distribution side, so brokers and MGAs and that kind of stuff. So, I mean, a lot. I think we can say that there's a lot going on.

Callan Harrington 02:00
A lot going on, surrounded by a hurricane, which is typical, I guess, now in Florida.

Margeaux Giles 02:06
It seems to be, which is such a bummer, the fact that you guys have to deal with that almost constantly.

Callan Harrington 02:12
One of the things that I want to come back to is that I started a consulting company about a year and a half ago, and what I love that you did is the SaaS product came out of the consulting company. I see that a lot. There’s a stat on that, but I don’t know what it is, so I’m not going to try to dig it up and see if I can put it in the show notes. But I need to verify it—it was so high. I was like, that sounds incredibly high, the number of companies that spun out of consulting companies. But it’s a great route. I love it. You’ve had a really successful career. Where did this all start?

Margeaux Giles 02:59
Like everybody in insurance, it started by complete accident. Nobody graduates college and says, “I can't wait to start that insurance career.” I mean, there have been a couple, but it’s few and far between. So I started as a CSR. I was coming out of college, I moved back to Tampa with my family, and I was just in that “now what?” stage that a lot of people find themselves in. I started working in a small insurance agency, and I didn't fall in love with insurance—let's clarify that. I did eventually, but in the beginning, what I really enjoyed was how messy insurance was on the back end. I enjoy untangling knots, solving problems. I'm a business process person, and when I got into the agency side of insurance, I realized that no one really knows what they're doing. There’s no standard practice. I thought maybe it was just the climate that I was in, but as I went through and started to consolidate the business practices within the agency that I was working for, and as I moved up the chain from CSR to selling insurance, I fell in love with putting business processes together and becoming really efficient. That’s what drove me to push on in the career I was in. It was a very natural progression for me, but it just happened. I think insurance really sparked that passion because it was so messy.

Margeaux Giles 04:25
To clarify, I was on the commercial insurance side. I did a little bit of personal property in Florida, which is not like personal property in other states either. So even that is, in its own right, complicated and a little more difficult than maybe some other parts of the country. I found that there was this lack of “we do ABC, and then we get to D.” Every agency had their own flavor of how they did stuff, and the business processes were very different from state to state, from line of business to line of business. I found it fascinating—I basically found this plethora of knots to untangle, and I’m still untangling them to this day.

Callan Harrington 05:00
Cool. I fell in love with insurance on that side of it too. I totally agree with you—nobody plans on getting into it. It’s funny, I was just talking to someone the other day, and the only reason I got into this is because my best friend was interviewing at Northwestern Mutual. When they asked him, “Who else could be a good candidate for this job?” I was the only phone number he had memorized. I had no internships lined up, so it was perfect for me. I’d love to back up a little bit because I looked at your career arc at OIG, which was the insurance agency that you came on, owned, exited—all of that. You’ve been through the full process, which I think is awesome. What was that journey like? For those that don’t know, CSR is typically an entry-level position within an insurance agency. Moving up the chain is not super simple because the agency has to be actively trying to grow. One of the beauties of insurance is it’s phenomenal. It’s one of the best business models. It’s why it’s so big in private equity—you can get to a certain point and you don’t have to work very much, which is great. It’s a different kind of hustle, but you’re right—some people might get to a point where it might get easier as you go up the ranks.

Margeaux Giles 06:27
That’s exactly right. And to clarify, if you started the agency, grew it to a couple of million in revenue, and you’re able to hire enough staff to operate the full business, you probably even—some will hire a CEO, or some will put in a managing partner. In that way, they don’t have to do as much, which makes it a great career path. I mean, if you start from scratch, those first 10 years are hell. But if you’re interested in hustle, you can get in, own a business, and become a business owner, I think, more quickly than in some other areas.

Callan Harrington 06:58
I think you’re 100% right. The progression for me was difficult. It wasn’t easy. It took a long time to go from being a CSR to understanding enough. But I think I had a competitive advantage over other agency owners because I didn’t start as a VP—it wasn’t something handed down to me from my family. A lot of people in insurance are in insurance because their fathers were, or they grew up in it. I think what made it easier for me was that I had an understanding of all of the processes, from the lowest-level employee or the most entry-level employee all the way up through. It made hiring and retaining employees a little bit easier for me because I had more of a rapport—I had more of an understanding of their daily struggles. I credit the largest part of my success to technology and the ability to embrace technology in an agency that, when I got there, didn’t have any. We were still writing everything on paper; we had filing cabinets. That was 15 years ago. But embracing that technological journey, I think, ended up being key when it came to the exit—being really successful and getting that edge and multiplier that made a difference. Taking an agency that, like you said, some people get kind of stuck in their ways, saying, “This is the way we do it, and we’re not going to change.” It’s incredibly expensive, you’re going to make mistakes, and it’s scary because it’s something that you probably didn’t know how to do prior to digital transformation. But if you embrace it, especially in insurance right now, as an agency or a brokerage, you’re going to have a leg up on those others that are selling without that technological advantage.

Callan Harrington 08:47
Yeah, I totally agree with that. I’ve spent a lot of my career in the insurance space, and I started out as an agent as well. A couple of points I want to touch on—one, I think that is one of the most interesting models. There are debates about whether you can be an effective executive if you haven’t done the job. This gets talked about all the time, especially in sales. You know, if you weren’t an individual contributor, can you be a leader of a large sales organization? It’s hard for me to say because I’m a little biased—I started as an individual contributor. But I will say this: to be the Chief Sales Officer of Microsoft, I don’t know that you have to be an individual contributor, because it’s so much more about scale at a really large level. If you were, great, but I don’t know how much that impacts it. But in earlier-stage companies, I think it’s very beneficial. I don’t think it has to be that way, but I think your team, especially if you rose in the ranks like you did, has a lot of respect for that. It also shows that you have a lot of empathy for what they’re going through.

Margeaux Giles 09:54
Absolutely. A lot of it is empathy, and that’s good that you touched on that. Even if you don’t have that experience, you can still be successful, but you have to prioritize truly being interested in understanding what your team is doing within their daily routines—what’s working or not working. You don’t have to sit in the seat to have the emotional intelligence or empathy to sit down with people who are in that seat and truly listen to what they’re saying and take action based on it. I had an advantage because I sat in the seat, so I didn’t necessarily have to do a lot of the fact-finding that someone else might. But I’ve seen plenty of agency owners and MGA owners who haven’t necessarily done that, and they’re still incredibly successful because they’re willing to listen to those people and try to solve the problems they’re having.

Callan Harrington 10:42
That’s so true. When I got out of individual contributing, an example I give all the time is when we implemented SalesLoft, a sales engagement tool at a previous company. I was out of individual contributing at this point, and I heard, like, 98% positive feedback, and 2% of people said, “We need to change this.” I thought, “Ah, it doesn’t really make sense; I don’t think we need to change this.” Then I joined an early-stage company where I was taking the inbound to help build the process before we built a team. I was using SalesLoft, and within 30 seconds, I thought, “I see what everyone’s complaining about. This is a pain; it’s not going to work.” I was 100% wrong, which I think shows the importance of listening to your team.

Margeaux Giles 11:23
Exactly. And that’s such a great point. The other piece I want to mention is the technology piece, and I totally agree with you on that. One of the areas I think is really interesting, and I’d love to talk about it a bit more, is taking those legacy businesses and bringing that technology inside of them to make them better from within. It’s not easy to do. How did you manage that?

Margeaux Giles 11:52
Yes, it’s a great question. If we’re talking about the digital transformation of the agency versus what happened when we got acquired by private equity, the challenges are similar but a little different. Walking through the agency’s transformation, I made so many mistakes because it was the first time I had gone through this process. I look back and think, “Oh my God, I made so many mistakes that I wish I could erase,” but they taught me so much about how to do this better the next time. Just simple things like watching a sales demo—I had no idea about software sales. I was in the insurance world, so going through the process of vetting technology, I made so many mistakes, like getting sidetracked by all the shiny features. You’re watching this demo, and you think, “This is so good.” We fell into that trap, made a six-figure mistake, and bought software because it had a really good sales rep and a shiny demo, and we ended up paying the price for that in the long term. But I’m thankful because had that not happened, I would never have had to build my own software.

Callan Harrington 13:03
Wow, that’s incredible. It sounds like you really learned a lot from that experience.

Margeaux Giles 13:07
Absolutely, but there are some agencies that are not going to be able to do that. So part of my daily work is fueled by a little bit of rage—I don’t want anybody else to have to go through what I did. A lot of what I take on now, and part of our consulting strategy, is helping smaller agencies avoid those mistakes. We’re not going to build custom tech stacks or do massive digital transformations, but we can help in that area.

Callan Harrington 13:35
Do you mind telling that story? I think it’s really valuable for people to hear the specifics of what you went through, even if you don’t get into names.

Margeaux Giles 13:44
Sure, it’s not a secret. We were really looking for a switch from being mostly personal to being mostly commercial. A lot of the processes had to be redone. I went online, and I did the same thing as anyone else—searched for insurance software. We had a legacy system that was very rigid, and we needed more flexibility. I didn’t understand then that tweaking software has a downstream effect. I’m not sure I would choose that path again. I watched so many demos, and there were so many shiny things—new buttons, and I was so used to writing things down and being what I call analog that I didn’t stop to think about the three to five most important things we needed to change and iterate. There’s no such thing as creating a perfect system in one fell swoop. And when you talk about rolling it out to your employees, you're talking about changing something they’ve done for 20, 30, sometimes 40 years. I severely underestimated the time that would take. I thought, “I love the software on the technology side so much that everybody in the agency is going to love it.” That was not the case at all.

Callan Harrington 15:00
Wow, I can imagine there were some challenges with adoption.

Margeaux Giles 15:03
Oh, there were lots of tears, fights, and meltdowns. In bigger companies, you're going to have attrition when you do big transformations like that—some people are going to leave, and you have to understand that going in. But all in all, it ended up being great. Even after my exit, I’m still building software for my agency. It’s never done, and if you’re going to do it right, it shouldn’t ever be done. It doesn’t mean you’re going to come in, drop a bunch of money, get a great new system, and everything’s going to be perfect. It really is a long process, but in the end, it’s worth it. I can tell you I got a higher multiple when I exited because I was able to show my book and my business in a way that competitors didn’t have. I could forecast better, show the value in my appointments, and demonstrate how steady my book had been because of all the data I had collected and analyzed. That alone was worth it, but it was stressful.

Callan Harrington 16:11
You’ve got about 15 things in there I want to go back to.

Margeaux Giles 16:15
No, not at all. This is excellent. A guy we had on the podcast, who was a former boss of mine and someone I think very highly of—he’s been a CRO at many companies and has three or four exits under his belt—said something very similar. He said when you’re in an executive position, and that could be when you’re exiting a company or in a larger company, you have to be able to tell the story with the numbers. Those numbers have to back it up, so if they take that and you’re not in that room, what you gave them needs to tell that story without you being there. I think that’s such a great point.

Margeaux Giles 16:52
Yeah, and there’s no better way to do that than when you have a couple of years of data behind you. I think agents and brokers don’t really understand the power they truly have. We’re usually the first point of contact, we have the ability to collect the most information, we can forecast—we’re the front lines of the process. I think agents dismiss too quickly the importance of collecting the data. When we do digital transformations, anytime I talk to a salesperson, it’s about how little data they can put in. They think, “I marked my sales job off, and I have to put these things in, or else my boss will yell at me,” and they hate putting data into a database. But if they could understand how that benefits them in the long term—yes, it’s more work upfront. However, if you’re in this business for two or three years, and you’ve been collecting data like this, you know your speed at renewal, your retention rate, year two, year three—you’re walking into the office, you’ve got $150,000 base, and your software is now doing the work for you. There is tremendous value in that. I think that’s an area where we butt heads a lot with the older, more senior, tenured sales reps and some of those owners—trying to get them to understand the true value they have and all of the things they can do outside of just sales, like retention, training, and hiring new employees. I just wrote a feature article for Forbes about the importance in InsurTech of creating software that engages employees now that we’re all in a more hybrid work environment. You don’t have the ability to just turn around if you’re a junior agent and get that advice from a tenured senior agent. So how do we incorporate that into your digital transformation? How do we get knowledge centers? If you’re working through a quote and you find a coverage that you don’t understand, can you click on it? Will it explain that coverage to you? Those types of things. When people start to understand just how deep that can go and how much of their business it actually touches, it becomes easier. But it’s hard to get people to recognize that—they’re very stuck in their ways.

Callan Harrington 19:00
That’s a great topic to chat through. I talk about this quite a bit because I started out in the field, and I’ve been a part of all sales—inside sales, outside sales, enterprise, SMB—and field sales in particular, it’s a pain. It’s a pain because you’re going from appointment to appointment. I remember days where I’d have to be in Canton, which was two hours away, then back in Columbus, then in Toledo—two hours, two hours, two hours—and I’m living out of my car. The last thing I felt like doing was updating. I talk about this quite a bit too. A number of companies will come up and say, “Hey, if you could build any tech product in the RevOps or sales or marketing space, what would you build?” It’s a great question because there’s so much good product out there. I don’t know that we necessarily need another one, but I will say this—it is a major challenge on both sides, the rep side and the company side, when you’re in the field, to drive good data from that. I love what you’re saying. I think that’s a really important area. If you can show what that looks like, then it could help. But yeah, it’s one of those things where it’s about how you can make that as easy as possible, right? Whether that’s a form—I’m using just rudimentary things—but if you can make it easy as possible to get the exact information that you need. The reality is, especially if you’re really good, your pipeline is going to grow real fast because people are going to figure out who you are, and then they want to talk to you. So I think that’s great, but it is a challenge for sure.

Margeaux Giles 20:30
One of the things we’re exploring now with the SaaS product is this idea of being able to network from your computer because there’s a lot of open-source data available. Before insurance, I worked for AT&T, selling fiber optics to companies, and I had a territory. I would literally drive to that territory, and I was out in the field all day. The last thing you want to do is try to type into your iPad. Back then, I was writing on a notepad. One of the things we’re trying to do is say, “Hey, it’s 2024. We do a lot of things from our computers, and you can do some of this pre-work, this networking, so that when you do get that face-to-face time with a potential insured, you’re coming in prepared.” We don’t necessarily have to have the long sales cycle that we used to. I’m a huge proponent of face-to-face human interaction—I will die on that hill. I don’t think there’s ever an instance where an AI will replace that, especially when you’re talking about commercial insurance, and you get into premiums that are over $10,000, $50,000, $100,000. We have premiums that we write that are in the millions—I’m never going to buy a million-dollar policy from a chatbot. It’s never going to happen. No one’s going to do that, so focusing on that human element is crucial.

Callan Harrington 21:47
That’s a great point, especially in those larger commercial deals. That human interaction is so critical.

Margeaux Giles 21:55
Exactly. What I’m looking at is how do we give sales reps the tools they need to be prepared for those meetings? There’s a lot of pre-work that goes into those accounts. You research the business, understand the risks, look at the person personally, see how many lines of business they need. Can we get a complete view of that person? One of the things we’re doing with the SaaS product is really harnessing some of the good InsurTechs that are coming out right now that pull open-source data—not PII, but basic data about the business or the person, that prospect—before we even make first contact. So that when I am making first contact, I’m prepared for that sales meeting. We do it in other sales aspects, right? In other industries, there’s a lot of pre-work. I do it when I’m doing consulting work—I research the client before I invest time and energy. That’s one of the things we’re looking at with the software—how do we harness these InsurTechs that are pulling data? There are companies like Plank, Fenris Digital, and others we’ve talked to about pulling in this data and really giving that sales rep pre-populated information. We’re saying, “We don’t need you to type this in or write this down. Here’s the base of information you need. We just need you to track your process and how long it took you to get there.” It’s all digital now—it’s not as cumbersome as it used to be, especially if we’re pulling in that open-source data and using those connections that we’re seeing come onto the market.

Callan Harrington 23:23
That’s huge for a salesperson. If you can walk in the morning, and your software has gone through your existing book of business and surfaced and ranked opportunities for you, and you wake up and open your computer, it’s like, “Hey, Bob got married in the last 60 days, and she owns a business. You insured Bob, but let’s talk to his wife.” That’s a great lead, instead of hitting the pavement, which is time-consuming and costly. Plus, there are these lead companies where you’re paying astronomical amounts of money for leads that nine other people are calling on, and they don’t want to talk to you—they’re angry by the time they do. So one of the things I’m looking at, and trying to convince MGAs and brokers of, is that you can mine your own data. There’s value in what you currently have. You don’t necessarily need a huge outside sales team if you haven’t gone back to the book you have to really maximize it. I can get owners on board with that because they see the value in making sure their book is rounded out. That’s one of the things we’re looking to build out on the SaaS side, which has been very exciting.

Callan Harrington 24:30
Absolutely, and I agree with that. There’s such opportunity in your own book of business. I would look at that in almost any business—any business that’s got volumes of clients. That’s one of the places I talk about all the time—your lowest hanging fruit is your clients you already have.

Margeaux Giles 24:50
100%.

Callan Harrington 24:51
So you founded Go Giles. Was this the first company you started from scratch?

Margeaux Giles 24:56
No, no.

Callan Harrington 24:58
Okay, so you had some experience with it.

Margeaux Giles 25:00
Yeah, so I joke because I was just telling this story the other day. My first company I ever started, I was nine, and I lived on a public golf course. I would go out at five o’clock when the golf course closed, and I would collect old balls that I would find on the golf course. I had a big bin of them, and I would ride my bike to the 7-Eleven, and I would get waters and Cokes, and I worked every weekend from about nine to eleven, sitting on the golf course selling balls and drinks. I was just naturally entrepreneurial. I loved enterprise, building relationships, and helping people. So at nine years old, that was my very first job, and someone wrote an article about it a long time ago. After that, I started a secondary company with one of my great friends doing club promotion and DJ nights, and we did that through college. Then I started a company called Zingo. Some people might remember this—it was a designated driving company where our drivers would ride scooters to you, drive you home in your car, and then drive the scooter back, so you didn’t have to leave your car at the bar. We did that for many years. We ended up getting sponsored by Anheuser-Busch, and I did that for many years. I tell this story too because it’s a cautionary tale for digital transformation. I went to Anheuser-Busch and said, “Listen, right now, when people are inebriated, they have to call our phones—we had a call center—and tell us where they are. I think we should build an application on the iPhone where they can just download the app, track their driver, track their stuff, and call for these on-demand rides.” Mind you, I was 21 at the time, so I’m in this boardroom pitching this crazy idea. Everyone was like, “Yeah, yeah, you’re a nice girl, no thanks.” I ended up selling that company for a profit, my first exit, when I was 21, and then, like, six months after I sold it, Uber came out with their app and just destroyed the whole concept of it. I died because I know that somewhere, somebody from that board meeting is watching this and thinking, “Damn it.”

Callan Harrington 27:15
Wow, what a story.

Margeaux Giles 27:16
Yeah, so that’s my cautionary tale for not embracing technology. But that was my first exit, and then after that came the insurance business. So I’ve had a couple of companies—I think I was born an entrepreneur. I’ve had successful companies before this, and I love it. It’s so challenging, and there’s no limit to what you can learn depending on where you go. Zingo actually ended up pushing me into insurance a little bit because I had issues insuring that company. I had to work with attorneys, and we actually ended up having a carrier create a special product just for our company so that we had the ability to drive other people’s cars. I remember thinking, “Wow, that’s really intense and interesting.” That sort of helped me get into insurance, but that’s my background.

Callan Harrington 28:00
I love it. So why a consulting company? You’re in these great recurring revenue businesses, and I’m not saying consulting companies don’t have their place—of course, they do. But it’s not recurring revenue, right? So what led to that?

Margeaux Giles 28:16
Honestly, it was natural. Once I started building software for my agency, my sales reps and carrier partners would come in, and they’d say, “You know, they come in once a month, we go over our numbers, and they look at your appointment,” and they’d come in, and I’d have more data on their business than they had. I’d be like, “Yeah, let me tell you all about your company. I quoted you 100 times, you lost 100 times, and here are all the reasons why.” They were like, “Damn.” So I started getting phone calls asking for help—“Will you look at this tech?” or “Will you help this agent?” At first, I did all of it for free, and then eventually I thought, “Yeah, I’m going to incorporate this and work on it.” What ended up happening is it just grew from there. I was open to the opportunities that were coming my way—I never said no to something because I wasn’t an expert in it. I was an expert in agencies and distribution, but when it came time to talk to carriers, I think a lot of people, especially women, underestimate their ability or get scared and are afraid to say, “Listen, I’m not an expert in carrier operations, but I can give you a unique perspective on how this affects your distribution channel. Let me get in the room.” I may not know all of the answers, and I’m not going to have the full gamut of experience, but I can find it, and I do have a network big enough to bring the smart people into the room to collaborate on those things. Being open to that led to the progression—from brokers and agents to carriers and MGAs, and then to InsurTechs. For the last two years, our biggest clients have been other InsurTechs that need SME, deep insurance knowledge, or they get funding, and now they need to scale.

Callan Harrington 30:00
That’s fantastic. And there are so many of them now.

Margeaux Giles 30:02
Absolutely. There are a ton of them. You’re not going to know everything, and that’s okay. At that point, I had never worked in software—I had no idea how software functioned. I didn’t know anything about the politics around it or any of the acronyms because there are so many acronyms.

Callan Harrington 30:20
Great call. It’s so true.

Margeaux Giles 30:22
Yeah, but being open to that, saying, “Alright, I’m going to push myself. Even though I don’t know this, I’m still going to be open enough to learn about it,” that’s how the progression went. And naturally, as you said earlier, why a lot of consulting firms push out SaaS products is because I was hearing the same pain points over and over again within the industry. So to me, it was like, “Why keep charging people to build custom solutions when I’ve built something 99% similar in a different scenario? We need to make this easier and more accessible to people because custom software builds are not easy, and they’re not accessible.” That’s what happened—consulting turned into a SaaS product because we knew the market so well. I never questioned what to build. It was always like, “We have to build this. Let’s go build it.” That’s why it was successful.

Callan Harrington 31:12
I know exactly what you’re saying. Or at least I think I do. But if I’m hearing you correctly, and I totally agree with this, you’re looking at a problem that’s coming up over and over again, and you’re taking the initiative because you want to do it a different way. You built into where you had a problem, and where you saw that problem, you leaned into it.

Margeaux Giles 31:30
I leaned into the most difficult, and this is factual about me—if it’s the most difficult thing, that’s what I want to work on. With the SaaS product too, we’re going after large commercial, the most complicated, complex sales process that you could possibly go through. That’s where we’re starting because I’m a glutton for punishment, and I just cannot resist the challenge.

Callan Harrington 31:55
You can't do these roles without it—you’ve got to be a total masochist.

Margeaux Giles 31:58
I totally get that, yes. So I was like, “You know what? That’s the hardest thing—let’s do that first.” Luckily, I have people who are also like that with me on the journey. But I think that it’s very true—it’s about leaning into the most difficult thing that you can solve. Here’s the thing—if you solve it, you win. I love that idea of being the one who finally cracked that code. I think that’s what kind of drives me in that masochistic world.

Callan Harrington 32:25
I love that. You know what? I found that with insurance in particular, and this is something I always liked, and I found it to be pretty common with other people—that insurance has a high barrier of entry. And if you’re going to do InsurTech, it’s much bigger now, but when you and I were getting into this, there was such a high barrier of entry because it’s so regulated. Especially in the Medicare space, where there are all the regulations to protect seniors. To me, I always liked that because it was a higher barrier of entry, and it was harder, but like you said, if you solve that, there’s a big win, and you can make a significant impact, which I think is excellent.

Margeaux Giles 33:03
I like that high impact. Looking back, the advice I would give is that there was a lot of pressure, especially for me, to go the traditional route—go to college, get an entry-level job. There were many times in my early 20s when, despite the stories sounding great now because it’s all wrapped in a bow, I was dirt poor, just struggling to get by. It was very, very hard. But I would tell my younger self to stay with that path because I don’t think that had I taken that normal path and stayed safe, I would have had the experiences I needed to take all of those steps. Every one of those steps was necessary. When I exited Zingo, it didn’t feel like a failure, but it didn’t feel like I had built a billion-dollar company. I was 21, and it felt like I was leaving something behind, and it was sad. But understanding that every failure is an opportunity for a new opportunity—every time I left something or made an adjacent move, it was always the right move. A lot of people get stuck in a hamster wheel, afraid of making a decision, especially a decision that feels really heavy, like quitting a job, closing a company, or selling a company. People like to stay in their motion and not recognize when it’s time to exit something or when it’s time to dig in and grow. Because there were a lot of those moments too where it was do or die time—I either had to quit or dig in. Understanding that is a necessary process. You are going to fail, hands down—if you’re worried about failing, this is not the job for you. You are going to mess up probably more times than you get it right, but every time you do, there’s something to gain and learn from that. I applied that every time I made a pivot, and I think that was incredibly helpful.

Callan Harrington 34:55
Margeaux, the mic is officially dropped. We’re going to end the podcast right there. Thank you for coming on. This was excellent—there’s so much good stuff in here. It was great to hear your story.

Margeaux Giles 35:05
Anytime! I love talking about myself.

Callan Harrington 35:10
I love it.