I Taught 10 People How to Make $40,000 Per Month in Insurance Sales

In this presentation, John Wetmore shares his personal journey from a low‑income upbringing in Boston’s projects to building an insurance agency that generates roughly $250 million in annual production and employs about 6,000 agents. He recounts early jobs, a brief stint as an accountant, a disastrous foray into sub‑prime mortgage lending, bankruptcy, and multiple career pivots before discovering insurance sales in 2008. After four years of selling a single policy, he committed to a high‑volume activity model, tracking calls, presentations, and recruiting minutes. By dramatically increasing his activity (e.g., 600 calls, 20 presentations, 30 recruiting calls per week) he grew his earnings from $6‑8 k/month to $460 k in a year without mastering traditional sales scripts. Wetmore distills this experience into the “Do More” framework—discipline, ownership, mistakes, obsession, resilience, expectations—emphasizing consistency, volume, and self‑accountability over flashy techniques. He stresses the value of embracing mistakes, seeking feedback, and maintaining professional obsession. The talk concludes with a free digital copy of his book and a downloadable activity tracker to help others replicate the model.
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Next, John Wetmore will be teaching us the 2 moral codes for leadership. Appreciate you guys. Good afternoon. I'd like to ask, what if what you thought about succeeding in sales Building a massive sales agency didn't take quite what you think it takes. You know, I— my background is lots of different things. She said accounting. That was the most recent thing I did before. Oh, that's a cool slide. I know we had that one. That's what I did right before insurance. But I have quite a lot going on in my history. And fast forward to today, we do have a lot of insurance agents. We have like 6,000 insurance agents sell policy last year, which is cool, which means my goal is always help people get paid. And I focused on that, and that's what's allowed us to grow a lot. And I had a lot of help getting where I'm at, and people helped me figure out how to get paid. So those things is what I'm going to be sharing with you today, and the concepts that I've put in place to build the agency the size we have. But for perspective, 10 years ago, January of 2014, in the insurance business I made a whopping $800 for the month. So a lot can happen in 10 years. Now we'll do, I don't know, $250 million in production this year. Doesn't suck. So if any of you are feeling stuck, like, what's going to happen next? Where am I? I've been doing this for a while. How do I break out of this thing? Man, it can happen. I grew up in the projects outside of Boston. So all I remember was being a kid is standing in line for cheese and peanut butter and taking my mom's food stamps to the store to buy her Newport Lights in the Box. That was my childhood. I had a blast doing it. We played in the park a lot. We caused a lot of trouble. We did things we shouldn't do. We threw rocks at trains. I just did a lot of dumb stuff, but I was a happy kid in the hood. And, um, you know, my— so my grandma was a teenage mom. My mother was a teenage mom. My dad wasn't there. Um, at all really. Every once in a blue moon he'd show up. I had to one-up both of them. I had my first kid on the way at 16. So my oldest today is 30. I have 5 children total. My youngest is 12. So I just started having babies in high school and I never stopped having babies. It was a lot of fun, but it was hard, you know, trying to take care of business. And, uh, out of high school I started working in high school at a pizza joint, worked 4 years there. Eventually ran, ran it as a manager. They paid me $7 an hour, gave me a cool title, but it didn't pay anything. Um, you know, and all through school, I, I like— my favorite thing in school was to skip it. So I did a lot of that. I did just enough to get by. I wasn't dumb enough to ever stay back, but I didn't want to go any more than I had to. Um, and unfortunately, that mentality and that path followed me along my life. And when I started working, I did just enough to pay the bills, right? And then I went in and I got a little warehouse job and I paid a little bit more. And at that point I had several kids and we bought like a new minivan to fit the kids in. And now the extra money I had was now gone again and we're just getting by again. And at one point I remember looking at people that were— I was in a very blue-collar job loading trucks in a warehouse overnight I remember looking at all the people that were ahead of me, older than me, had been there a long time. And, um, again, I work nights. There, there was a day shift also that unloaded trucks. At night we loaded them. At night everybody's goal was just to get day shift. That was their goal in life. You've been there, I heard it, you know, that was it. I was like, that, that's the vision. Just do the same thing in the morning, then at night. Like, this sounds stupid. So I was like, I don't want to be in that spot. That was my future. That's what I saw as the potential future. And I was like, I gotta go back, I gotta go to school, right? I'm mid-20s or whatever. I'm like, I guess I should go to college because I didn't do that out of high school. I walk into a local community college we have in the hood where I grew up, and it was like no money to go. I walked in and I go to sign where you go to sign up and there's this little board. We have all these majors, all these different colored flyers. And a lady walks up to me, she's like, "Can I help you?" I'm like, "Yeah, I wanna go to college." She goes, "What do you wanna do?" I said, "I have no idea whatsoever. That's why I'm staring at the board here by myself." And she goes, "What are you good at?" I said, "I'm really good at math." And so she says, "Why don't you become an accountant?" I was like, "Dope, let's sign me up to that." To this day, I still hate that lady because she asked me no questions whatsoever other than, "What are you good at?" And math has nothing to do with accounting, really. And I got stuck as an accountant, and I'm not supposed to be one. But it did help me a lot. I learned a lot from it. The biggest thing I learned is I was a corporate accountant, not even a CPA. Every time I tell someone accountant, they think I did taxes, and I didn't even get that far. Um, again, I just kind of limped into accounting too. And, uh, you know, when I started seeing what the potential was in that position, same thing. It was like I was at my peak. I was making $40 grand a year as an accountant crunching numbers. And the person in charge who told me what time I had to show up and when I could go to lunch and when I could take a break and when I could go on vacation and when I could do all the things, she was making like $80. I'm like, she'd been doing it for 30 years. Like, shit, here we go again. I guess I gotta get better at this, like, picking a career thing. And again, I saw the vision and I'm like, I want more than that. I want— I just don't know how to do it. I always felt different. I always felt like I could achieve more. Anybody feel something inside of you? I'm like, I know I'm not supposed to be here. I'm supposed to be there, but I don't know how the hell to get there. That was me. And, um, you know, at this point, um, I'm, I'm what, 27, 28 years old. Doing accounting work that I hate. I get a side gig in the mortgage industry. Kobe, I know you're here killing it. I was the guy who sold all the 100% subprime loans and 100% no-doc investor loans. You close 4 of them in a day and they ask no questions. So I was one of the ones that contributed to ruining the country by giving out money that people couldn't afford to pay back. And, uh, I sold a couple loans And when I sold the loans, I made good money. And then I went out and bought stuff. And the first time I did a couple loans for that investor, I made like $10,000 one month because I closed a loan for— 4 loans for one dude in one day. I made like $10,000. And I went out and bought a new truck and a new house because I acted like I signed a record deal with Jay-Z. And I really just closed 4 houses that foreclosed the next year. And You know, at that stage, that was 2007-ish. I went through that year, I lost everything because I started spending money I didn't have. I had two houses taken back because I had the little baby house where I was in. I bought the big one I shouldn't have. They took both of them back. I then learned when you get a mortgage and quote unquote buy a house, it's not really your house, it's the bank's house. So they wanted their shit back when I didn't pay for it. I got my car taken away, I filed for bankruptcy, and I got divorced. All in like a 12-month period. Yeah, really, right? Sometimes life punches you in the face. So I go back to accounting for 4 more years, hard to find a job. Long story short, get back into accounting, but I still have this vision of like, how can I figure this thing out? I do get into insurance, um, part-time. Somebody again refer— someone I knew in the mortgage business, knew me, knew I had like a vision, like I want more. So he referred me to insurance. And I get in— long story short, I get my license, I pick up the phone, I start calling clients, right? There's so many of y'all that are in insurance. I've talked to a few of you guys. I start calling clients. They basically told me no or to F off or they didn't do it, right? Hung up on me, whatever it was. And I was like, this don't work, I quit. And after one day in the insurance business, I quit, went back to accounting, right? Because it was hard in my head. And, um, I, I just go back to this job that I hate, and I'm like, but all these people are succeeding in all these other industries. But I kept like putting in a little bit of effort and didn't get rich right away and quit. And I did that multiple times over. I just kept giving up. You know what I mean? I didn't push through. And I'm like, God, I gotta, I gotta figure something out. So get into, um, back to my accounting job for a couple years. Long story part, like, it goes through it. I get back into insurance. I had a buddy reach out to me and he DMs me and he's like, hey dude, I met this guy, I found something I think you'd be good at. It's the guy doing the mortgage business. And he's like, are you open to conversation? I call him, he's like, hey insurance. I was like, no, I did that, it don't work, I'm not doing that. But he comes and he expl— he, he takes me to dinner, actually offered me vodka, so I went, because that's how I used to like bury my feelings and all the problems. So I go meet him at a bar, he explains the business to me in terms of like, you can sell to get out of a situation, and or you can build a business and you can hire agents and you can build something. And it reminded me a lot of the mortgage industry, they're very similar. And I was like, let me give it a try. I get into sales again and I'm 2 years in the business. This was 2012. This happened. I get back in. So for perspective, I got in, I got in, I applied in insurance in 2008. I got my license 2010. I didn't sell my first policy till the summer of 2012. It took me 4 years to sell one policy. Yeah. So I start messing around with a little bit. I do it part-time for a year. I make enough to figure things out. I make $50,000 part-time. I leave my job. I start doing it. But I'm like very up and down for the next 2 years in the business. One month I make a few bucks, next month I make no money, next month I make a few bucks, next month I make no money. And it is very roller coaster style, right? And, uh, I was extremely tired of being stuck there. So I start looking at my situation, and I mentioned the divorce prior, right? Now I got 5 kids at this point. My youngest is like a year-old Maddox, who's now 12, and I still can't buy my kids the stuff they want. Christmas still sucks. I still have to tell my kids no. They still go to public school and ride the bus where dumb shit happens on public school buses. That frustrates me. And but I didn't know how to get out of the situation. Fine. When I got divorced, I signed this paperwork that was like, you pay alimony later, because I made money in the mortgage business for half a second. I couldn't afford it then, so they delayed it 5 years. 5 years came up March of 2015. I get a letter in the mail like, hey dummy, you haven't paid your bill, you owe $1,000. And I lost my mind because I didn't know how to pay an additional $1,000 bill obligation. I didn't know how to do it. And I always ask people, like, if I gave any of y'all— maybe it doesn't happen to everybody— an extra $1,000 obligation a month, would that stress you out? Right? And I felt that. And I started— I had a guy that challenged my thought process. And I remember, like, any of y'all struggling in sales, like trying to figure out how to get to the next level? You sell something? A little? You? Yes. Jeremy, right? I know you're in insurance. You do exactly what I do, don't you? Cool. How many last week, for perspective, Right, you good if I ask you some questions? Last week, how many presentations did you make to attempt to sell? Ballpark. 12. 12. Cool. How long does each one take? About 30, 45. 30 minutes. So 12 presentations, 30 minutes, 6 hours of presentations. And then you prospect also to set up appointments, make phone calls, whatever that leads. How many of those did you do last week, roughly? At least 300 a day. Okay, so you can do a few hours a day. Like, if it's— it takes like a minute for a phone call in my world. We call leads, right? So most don't answer. You're just— you're prospecting like crazy. So a few hours a day of that, 12 hours a week of presenting. So when I did— when I did mine, I'm gonna— I'm gonna explain it up here. I sat with myself and I looked at my numbers and I was making 8 to 10 presentations a week, hour a pop, and I was making 150 phone calls a week, which takes a few hours. And I said to myself, I'm making— I'm working 15 hours in money-making activity. Does that make sense? But I was making X, I was making like $6,000 a month. And I learned that every presentation I made equaled a dollar amount regardless if I closed it or not. Right. So for me, I was making 8 or 10 a week. But I was making like $6,000 or $8,000 a month. And one day I did the math and I was like, every presentation equaled $200 regardless if I closed it. Does that make sense? And I, I had to have this period where I really wanted to make changes in my life. And this is a question I ask a lot of people. This is like for you and other people. I have this off the sign that hangs in my office and it says, do you hate losing so much you're willing to change, or do you hate change so much you're willing to lose? And for me, I was at a position where I had to make a change. This, this child support thing came to me and I lost my mind. And someone challenged— they asked me the questions like I did to you, and I realized when I presented it, when I prospected, those time frames only added up to like 15 or 20 hours a week max, like on a good week. And I was usually exaggerating. And I decided that I was going to go out and change my world to make it to where I never have to worry about $1,000 again in my life. That makes sense. And when I started going at this with a different level of activity, for me, this is one thing that helps me a lot. If you write down some level of activity— for you it's phone calls and some presentations. For me, phone calls I can do 16 hours, presentations I can do in an hour. This is how my math added up. I was doing 150 phone calls, 8 presentations, 6 recruiting calls, and that added up to 12 and a half hours a week in money-making activity, right? So just write down your stuff, whatever you sell. I prospect, I present. Here's how much, how long each one takes. Here's the number of hours making money. But I realized I was making $2 grand, but I was only putting in 12 and a half hours. I'm like, shit, that's $160 an hour. But I felt like I was no good at what I did. I felt like I didn't know how to sell. I felt like I didn't know how to get to the next level. And I said to myself, because I was like trying to figure out how to be a sales guy, but I'm not a sales guy. I'm a dude from the projects who's willing to work hard. I don't know any PQ and 7 steps to sales. I don't understand that stuff. I don't wear a suit and tie. I don't— I don't— that's not me. But I was doing something. And I decided to go like, what if I just go at this different instead of— I spent 2 and a half years trying to get really good at sales, and I decided to take a different approach and go, just what if I just do more of this and worry about getting better later? Hence the name of the book you saw on the previous screen. Um, and I just did basic math because I wasn't accounting, and I'm like, if I just do 40 hours of it, so now instead of 100 calls I do 600, instead of 8 or 10 presentations I do 20, and instead of 3 recruiting calls, I do 30, it adds up to 40. If I just take those hours, just doing the same exact thing with the same exact skill set, with the same presentation, the same phone script, all the stuff I thought I sucked at, if I just sucked more often, I can make $300 grand. So I was like, "That's it. Let me just try that this year." Right? Let me just figure it— I'll get better another day. In that year, I went out and I made $460 grand. Doing this. I didn't learn how to sell anything any better. I was in the same industry I struggled in for 4 years, and I just took a different approach, right? And when I look at the Do More, for me it does mean some things. I'm sorry, it's skipping a little bit out of the order, but for me, the D does mean discipline, right? So it's like, the problem I see with a lot of people is they're disciplined this week and they're not disciplined next week, or they're disciplined on Monday and they're not disciplined on Tuesday. And John Maxwell has this quote which I really like that says, consistency compounds, right? And discipline is the ability to do things that you said you would do when you don't feel like doing them. Consistency is the ability to do those things over an inordinate amount of time. So if you have discipline and you put consistency with it, things compound. And I didn't understand that logic. I was trying to like do the same activity but get so freaking successful at it that my income went up. And I just decided to kind of reverse the order and go, getting better is important, but if I do more of it, won't I just get better by default? And I was okay with that approach. I don't have to be the number one sales guru. I don't care. I just want to make money for my family, right? So this model of do more became more than just like the workload. And this is what I started teaching, and the concept is having discipline in the right areas, not just the areas you feel like having discipline in. And you can make this apply in anywhere. I can do it in sales. I can have discipline with my children to make sure I, I see them when I need to see them. I can have discipline in the way I speak to people or agents who frustrate me. During a sales part. Like, I get frustrated with agents because they don't do A, B, and C, and I want to just tell them to like stop being lazy and go— like, I want to yell at people by default, which isn't good. So I had to learn how to have discipline in conversations. I had to learn how to control my emotions. I have to have discipline in a lot of different areas of my life. Ownership is the second part of it, and for me, ownership really means own your shit. This is how I talk to myself, but like I put up a nice version of it for people that don't like when I cuss. But for me, like I just had to understand who I was and be okay with it. You know, I was a dude who gave up on a lot of stuff. I don't have like the biggest vocabulary. Some of the stuff some of you guys set up here, like I gotta— I'm up there and I have to like Google the words because I don't understand them. Does it make sense? I don't— I don't— I'm not that deep. I would get frustrated. I was super emotional. So when people— clients told me no, I would get frustrated, right? When, when agents didn't perform the way they did, I would get annoyed. And I had to understand that's who I was, and I had to make change. Again, the change thing had to be on me. I had to own who I was, and the reason I wasn't growing was because of me and my problems. So I had to take those things and start to adjust them and get better at it. Does that make sense? And I try to help people understand, like, it's okay with who you are. Your deficiencies are okay. Can we tweak them? Can we get better at them over time? Sure, you know. But I was trying to be— there was this guy that was so good. He was the number one producer at our company, and man, he could rattle off some of the slickest sales stuff I've ever heard in my life. And I would show up to a client And I'm like trying to regurgitate the things he said the way he said them, and I just didn't— it didn't feel like me. I wasn't being genuine. And I'm like, can I just be me and just do it and figure out how to make a bunch of sales also and just connect with people? I'm a curious guy, right, which Nicole talks about. I'm like, if I just ask questions, people answer. I don't have to go salesy because that's not authentic to me. I'm like, can I just talk to them? And that started opening people up. And what's crazy is the activity level for me took the burden off of having to make a sale. You ever have to make a sale because your bills are due? It's a really shitty situation to be in, and I was in that for far too long. I was 35 years old and broke as a joke with 5 kids. So every time I'd sit with a client, it was all about me, not them. When I see 3, 4, 5, 6 people a week It's about how much money can I make in that situation. When I started seeing $30,000, which wasn't anything— again, $40,000— all I did was get to 40 hours. Some people look at it and they're like, work smarter, not harder. And I want to punch those people in the face some days. I'm like, can't we work smarter and harder? Can we do both? You know? And I'm like, I'm not working that hard. It's just 40 hours. Like, isn't that average? The problem is we tend to work 40 in the wrong areas. Or we tell ourselves we're doing work when we're not doing work. So for me, my work became presentations, prospecting, recruiting. Everything else didn't count. I just was going to do 40 in the right areas. Next spot, mistakes. Mistakes are insanely valuable if you do them the right way. And I think there's like 4 real good keys to mistakes. Number 1, be willing to make them. I think it's a really simple one most people won't do. A lot of people don't want to mess up. Perfectionists. I need to know everything before I do it, which makes zero sense in any application at all. You know what I mean? Maddox, if he wants to know how to play baseball before he plays baseball, would be really weird. You know what I mean? But I hear a lot of salespeople that just like, I want to get really good. And I was that guy. I'm like, I want to know exactly what to say before I take the step. So be willing to make mistakes, number one. And you can obviously write these down if you'd like. Number 2, own that you made the mistake. When you mess up, it's okay. Stop blaming everyone else. I was a guy that every time I missed the sale, it was the client's fault for some reason. They were broke, they were stupid, they didn't understand, they didn't need it, they didn't— you know what I mean? Whatever it was, it was always another person. It was, I was in the wrong area, the weather was wrong today. You mean, I always found reasons why 'Cause I didn't wanna tell myself I was messing up 'cause that hurts, you know? Number 3 part of mistakes is I think getting feedback from people who are better than you and where you wanna be about the mistakes, like be vulnerable, like was talked about 27 times today, you know? And it's okay. And some people wanna like not say where they messed up. So me being vulnerable, getting feedback from someone who is better than you— please don't ask the people who are broke next to you about the issues you're having because they'll probably whine with you. And the last thing is implement the advice you're given, which is a killer for most people. Most people won't implement it. Obsession is really simple. Like, I was taught, if you want to get paid like a professional, you got to act like a professional, and you should know your craft inside and out. Not day one, but you should learn it. Again, I, I do want to learn stuff. I just want to learn it after I do the activity. And when you have a lot of activity and then you combine it with coaching and counseling, you tend to get good really quick. Resilience is just— I talked about it earlier. A lot of you guys related to being broke and having issues. Like, we all got shit in life. Stop using it as an excuse. Use it as the reason why you should get out of your situation. You know what I mean? Like, my wife was 40, first mammogram, all is fine now, diagnosed with cancer, breast cancer. She had to get surgery to get it removed, had to go through radiation for like 6 weeks. She went to radiation on her lunch break, worked every day, didn't miss a day of work. You know what I mean? A lot of people use all kinds of reasons why they can't do stuff. So just get through life and again, don't compare stuff. Expectations is the last one I'll tell you about. Inky Johnson, hey, y'all know him? I love Inky. We live super close to each other. Our kids go to the same school. I follow him online. He says expectations is premeditated disappointment. You know, and if you look at any situation you're probably frustrated about, it's probably because you expected someone to do something differently. So just be very careful about expectations of others. And pay more about— more attention to the expectations you put on yourself. You know, it'll get you into a lot of trouble. And so this model has been what's helped me get where I'm at. I have a couple QR codes up here. If y'all do it there, I do actually have a book. And at the first slide, somebody else said— saw it, said buy now. I'm actually giving it to y'all for free. Like, so if you scan that, um, it's a digital copy. There's no catch whatsoever. I literally just giving it out for everybody to impact. So scan it. I hope this thing helps for you guys. I appreciate all your time, and I'll be around for the day if you need help. Hey guys, you know I preach do more, I preach activity, I talk about tracking your numbers. And for now, for the first time ever, I'm giving away free my activity tracker that I've used my entire career to keep up with my numbers— how many clients I see, how many phone calls I'm making, money, deposits, how much I make per hour, all kinds of stats that you can get by downloading the tracker for free on the link below.
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