‘First and Foremost, You Must Learn Insurance’

I fell into it. I don’t know anyone who’s a millennial who wanted to work in insurance; most of us fell into it because we had an uncle or something who just kind of got us in. I mean, now I know there’s more and more people who have risk management degrees, and they study it in college, and they become aware of the industry younger.

I did what everyone else did. I kind of thought I would do something else. For me, I was going to go to law school. And I had an uncle who was in insurance, and he was retiring, and he knew someone who needed somebody, and so I did what a lot of people did where I took a job at a brokerage firm. “You know, I’ll do this for a year, and then I’ll study for my LSAT, and I’ll go to law school.” I’m still here 15 years later. It’s a story that I think probably 50% of people in our industry can say is the same.

I was kind of drunk in a bathtub six years ago, and I came across an insurance meme site on LinkedIn. And they were making jokes about insurance. It was very LinkedIn-friendly, it was very clean. [I thought] I could totally do this, but I’ll do it on Instagram so it’s outside of the corporate tornado of LinkedIn.

If you go back on my site to 2019, the jokes are really basic. I couldn’t really figure out what I was doing. It didn’t really click until COVID in early 2020 and we all got sent home. And so then I went really far with the jokes.

I want to say right around that time is when Aon and Willis were trying to merge or the news came out that they were going to merge. So I started making jokes about that and making the jokes more specific. It was one of those things where I thought we would be home for three weeks. So I just started making them a bit irreverent, a bit spicy, thinking that it’d be this funny thing, and I would be done in three weeks, we’d be back at work like nothing happened. And then it just blew up so fast.

For the first several months, nobody followed it, and then somebody found it, and then somebody else’s algorithm found it. And then it became seven people and 70 and 700 and then 7,000. It kind of took off from there. How it [has been] molded from there is a long journey.

I’m making jokes about what we do. That was the first thing people saw, and they’re like, “Oh, wow, you’re making jokes about bind orders.” But I think also what keeps people there is I literally try to pander to what people need or want from the site. Which sounds, you know, weird. But what I mean by that is when you have a site [where] its followers determine what it is, they respond to certain things, they don’t respond to other things. They DM you and tell you what they’re looking for. You put out a poll, or you put out a survey on pay. And certain things meant a lot to people.

There’s only so many jokes you can make about buying orders, and those are always fun. But when I started talking about pay equity in the industry, or how to advocate for yourself if you want a promotion, or traveling, or how to grow your book of business, and kind of make it more of a sounding board, people really responded to it.

I think what drives people to the site is that I let people tell me what they want from it and I try to go in that direction. Sometimes it works, sometimes it doesn’t. Sometimes it can go off the rails. When this site was smaller, way smaller, and I had less of a responsibility to the masses, somebody would complain about one thing, and I would repost it, and then you keep reposting things. [If] you’re not careful, it just becomes an echo chamber. It doesn’t really get anybody anywhere. So you had to have a responsibility to keep the train on the tracks.

But, for the most part, the conversations on my site are controlled by the people that follow it. Definitely interesting what people will tell an anonymous site. They’ll write into my DMs. To them, it’s screaming into the void. I have a very unique insight into the mood of the industry at any given time. Sort of. I say that, but remember, 200 people might write me about something, but there’s another 58,000 who haven’t said anything.

But for the most part, I get an idea of the vibe of something, and I feel it just tells me, it tells all of us a lot more than the guarded corporate-speak that you get on LinkedIn. I know why LinkedIn is the way it is, it’s a very public kind of bulletin board. We have to behave a certain way on LinkedIn.

Instagram provided a place to be a little looser, be a little bit more irreverent, a little bit drier. And it was supposed to be funny. I hope it’s funny. But behind all the humor it’s supposed to have larger conversations and get the message across to people that, first and foremost, you must learn insurance. That’s the base thing that you should be doing. And here’s how to maybe talk to your boss about traveling or making more money or whatever. But I wanted to get people thinking about their career trajectory through the humor and the conversations that were being had on the site.

That’s a really good question. Anything that we try to infer from the different generations is always going to be against the background of what we’re told in the media. You know, everyone said that millennials were entitled and that they couldn’t work hard unless they felt that they were going to be the CEO someday. And we’re told that Gen Z is very nihilistic. We’re still trying to figure out what they are. People made a lot of assumptions during COVID, and now it’s different. People make assumptions about boomers being greedy or Gen X, they divide their personal life and their work life. All of that is going to be against the background of what we’ve been told about them.

The way they interact with my site is pretty much the same. I can say that Gen Z asks a lot more questions about the future of their career, whereas boomers will be much more reflective. And Gen X and millennials are more in the thick of it, so they’re just sending day-to-day observations about work.

Gen Z tends to ask money questions, which I find very interesting. They’ll always ask me, “Will I make more money underwriting or broking?” And that’s the question: where should I go work to make more money? They’re thinking of it in terms of, “Where can I line myself up? My buddy works at this firm, and he’ll be making $200,000 within five years. How do I also line myself up at a firm that will do that?” And there’s less concern over how do I learn as much about insurance as possible, and what would be the best firm for me to do that, where I can wield my expertise in a way that will get me money?

To me, it’s not so much about the generation, but it suggests to me that Gen Z isn’t being trained at the level that we were all trained. There’s several reasons for that. One is obviously COVID. It disrupted the in-office part of our job. And the other part was a lot of the materials that we had. I’m an elder millennial. There’s a lot of insurance materials that were available to me when I was starting out. [There were] IRMI [International Risk Management Institute] manuals that were sitting on shelves in my boss’s office that you could always look through. If somebody’s asking a question about a form, I could go look at it. And I don’t think Gen Z has that. They literally don’t even know that all of this stuff has been digitized. Most major retail firms have subscriptions, and they have a password, and they could be looking it up on their own, but they have no idea.

I get really basic questions like, “I just started insurance a year ago, what should I be reading?” I don’t know how to answer that. I don’t know what line of insurance you’re in. I don’t know what industry sector you’re in. A year in the industry, they don’t even know what they should be looking at, or, hey, should I be underwriting or broking, which will make me more money? They’re not [asking], “How will I learn more, how will I be better positioned to be an expert in this field?” There’s not questions like that. It’s very cut and dried—how can I make more money? I’ve just noticed the lack of training, and I don’t know why that is.

With boomers, it’s more reflective. Oh, back in the old-school days, we used to work on fax, everything was printed out and we handwrote quotes on paper. It’s very romantic when you hear about it from them. And that’s always really fun. They’re there for the nostalgia.

No, never, really. The only pressure I feel is to put out more content and that I have to avoid. The key to success when you’re an influencer, which I am not, but I’ve spoken to people who are, they’ll say that the most important thing is to have regular content, to regularly post, and to regularly use that network. And I don’t know how to do that because my site is not an influencer site in that way. I’m anonymous and I’m posting memes. I’m more just celebrating or informing about our industry.

There’s some pressure to continue to post. But as far as what I’m saying, I genuinely think that most of that comes from the things that people send me. A lot of the time I’m just reposting stuff that’s sent to me. But there’s also more like the mood, something big will happen in the industry, and then we all talk about it. Or we all talk about pay review, we talk about whatever. I’m in the industry with everybody else. We’re all in it together. I happen to be running this site, but in general, I’m just driving the bus. So I don’t think that there’s pressure in that way.

The pay survey was an accident. On Instagram, when you post a story, there’s a question box that is automatic. I think I posted, “Hey, tell me about where you work and what your pay review was like.” And people started writing in, “I work at blah blah firm, and I’ve been there for three years. I’m a male, and I made $68,000, and I got a raise to $82,000.” I was sharing to my stories the responses I was getting in that little question box. I was posting 50, 60 a day. I made $82,000, now I make $100,000. Oh, I made $150,000, now I make $200,000. And people were talking about what city they were in.

I was not consolidating this information, collecting it, writing it down. It was just resharing, resharing, resharing. It was very bizarre: my site went from, I don’t know, 19, 20,000— this is three years ago, four years ago— to 35,000 in a matter of a week. It shot up so fast. I think by the end of it, I doubled my followers and a couple of insurance trades wrote about it.

What’s interesting is I [personally] don’t like pay review stuff. Some people need to know what other people make, and I think that’s important. I think that transparency is important. I’ve always worked in a sales production way where my compensation is tied to what I’m producing or what I’m selling. So for me, it doesn’t really do me any good to know what other people make. It just stresses me out. But for others, they might work in … [a] very corporate thing where you want to know if you’re this title, if you’re account manager 3 and you know the pay band is this, you want to know what other account managers your age are making.

I did not foresee how addictive that information was going to be. It was wild. And then everybody who DMed me separately said, “Please write this down. Can we try to put it in some kind of chart?” So I tried to, but it was hard to go back and collect that from a bunch of DMs. So what I did the following year is I had a Google Doc that people filled out. And that also was shortsighted of me, because people could type in and it was all blanks. So then cleaning the data became very difficult. People would type crazy stuff in, or they wouldn’t type the number correctly. I had to get an actuary to help me with that.

Sometimes if you’re the first hundred people answering, it doesn’t do you any good. But after you have 10,000 people answer, you suddenly have a good sample group of data. That’s important, because people would go to their boss and say, “These people my age are making more money than me.” And the boss will say, “Well, you don’t know if that data is accurate.” But if you go in with 7,000 pieces of data and say, “No, actually in this city, people my age working in this rough sector are making more money than me,” that’s hard data. That is data that every firm’s HR has. And now my followers have it and they’re able to go in and say, “My market value is this, and if I’m not going to be paid my market value, I can then go and shop around.” A lot of people had written to me saying that they’ve used that information to negotiate really sizable pay increases or that it finally gave them the push they needed to find a job elsewhere.

A lot of people do the pay survey and realize they’re being paid very well, and they’re very lucky, and maybe they should stop complaining. There’s all kinds of information to be learned from good data, which is what the site is trying to do. Every year we do the pay survey, we get more and more people who answer it. What it was more about was individuals. How long have you been at your firm? Is it time for you to go? Have you not advanced long enough? The data was telling us different things, like who was staying at their job too long and not advancing. And there were people who jumped around too often. There were people who didn’t jump around enough, and there were people who jumped around every four years, which is like the sweet spot. And they were making a lot more money. So the data was more about movement in the industry.

I don’t know the answer to that because, first of all, the tagline safe place for insurance professionals was joking around. I don’t know where safe place came from. It was just, hey, this is a fun place where we can speak a little more freely than maybe we could on LinkedIn. But now it is a safe place for everyone. All kinds, very senior people come and send information and tell me things, and in a way that’s good to share with everyone. As the market changes, I don’t know what it’s going to be.

I mean, we all made it through COVID together, and none of us knew what the hell that was going to be. And we took it one step at a time. Now we have a situation where the market seems to be, at least in the casualty space, softening overnight. And we have a lot of action in the Middle East, and the risk profiles are changing, capacity is changing, and I have no idea what it’s going to be. I’ll still be here.

I’ll say this, I’ll do this site as long as it works. I’m not really going to take it to TikTok or something. So as long as Instagram’s a thing that people use and go and visit, it’ll be there. There’s not as much action as it used to be. Five, six years ago, Instagram was something you went and looked at pictures, and so when you post a still meme, it worked and tons of people wanted to look at it. People know this now, but Instagram is taking on a TikTok sort of model where it’s all about the Reels, people flip through and they’re watching videos. I might like post a scene from a movie or something, but I don’t really do a lot of video. The algorithm doesn’t necessarily favor that. I’m doing still memes, and I’m doing a lot of stories. So engagement has lightened up a little bit because Instagram favors influencers who are doing long-form videos.

But for the most part it’s still a safe place for professionals. As we navigate a new market, I’m still going to be there posting jokes or posting things about it.

I don’t think people realize how much information is available to them about the actual subject matter of insurance. We’re selling contracts to people, and we’re not lawyers, which is crazy. You really shouldn’t be selling a contract to anyone if you don’t know what it is. There is information from the Risk and Insurance [Education] Alliance, from IRMI, from the Institutes, which is how you can get your CPCU, how you can do your CE credits. Chances are, the organization you work for has a subscription to one of those organizations, and you just need to talk to your HR or even send an email to the organization directly and ask them for a login. You probably already have IRMI’s entire library at your fingertips for free. And anytime somebody in your office or a client is asking about a coverage issue, all of that is available to you.

Do not resort to using AI. AI can help you a little bit, can help you shape out an email, but you need to learn insurance, and you need to learn it from insurance manuals. If you don’t, your job is going to get eaten up by artificial intelligence in a matter of five years. But if you really learn the intricacies of what we do, your job will be safe for a long time. So don’t worry about whether broking or underwriting is going to make you more money. Just learn insurance, and once you know what you’re doing, the road will illuminate itself for you.