Since the time I could work, I did. I liked to be able to buy things when I wanted them. I liked the freedom that having your own money would provide. If you were to ask any of my friends, they would confirm that I am one of the hardest working people they know. I like to work. I like to keep busy. I like to be in charge and I like to win. All of that to say that during my entire college career, I worked both during school and outside of school like a crazy person. The years flew by because I rarely had a second to spare. Between working a full-time job in retail, a part-time job at a bank, having a boyfriend and active social life and always carrying a full course load, there was just never a dull moment! So, when I graduated, I accepted a full-time store Manager position with the retailer I had been working for, and moved back to Kansas City with my new big-girl job. I stayed with this retailer for 7 years, taking multiple promotions and receiving awards along the way. In 2004, I became pregnant with my first child, and I succumbed to all of the unsolicited advice about how difficult it was going to be to raise a child while working a retail schedule. I left soft lines retail and accepted a position as a Branch Manager at a bank. They were hot into recruiting retail personnel at the time, as they wanted to bring a customer-centric focus into banking. That job was an absolute beating and one of the worst experiences I have had! They had these kinda crazy unrealistic expectations for sales. They required you to be on a million calls a day to get numbers from you, and I gotta tell you, there are only so many checking accounts one person needs. At some point you find yourself folding under the crazy pressure to meet numbers and have great operations and give great customer service and control your wait time…it was all too much. I hated it there, and it wasn’t really any less work than what I had been doing in retail…the hours were just different. So I went back to retail. This time big box, department store. Different than the specialty retailers I had been with, I set out to learn the other side of things that I felt I didn’t have experience in. And it was an education for sure. Similar issues and pressures as any retailer, but on much larger scale. When I was in specialty, if we needed to make the day, we could work with one or two more clients to make that happen. When you work in big box, the numbers are so much larger that you can’t directly influence them in the same ways. It was a great education. I liked my time there, but in the meantime, my son was getting older, his father and I decided to get married, life was changing. And as my son got closer to being school-aged, we really started to have discussions about potentially moving away from Kansas City. See, I had lived there my entire life, except for the time I was in college, and that college was truly only about 45 minutes away from home. I felt like I was ready to see new things. My husband had lived all over, as his father worked for the airlines while he was growing up and they moved often, so he really wanted to move out of Kansas City. I knew that I didn’t want to move my son in and out of schools once he started, so I knew if we were going to move, the time was now.

I didn’t have the first clue how to make something like finding a job in another state happen, but if I am anything at all, I am determined. When I set my mind to something, I will find a way. I set about cold-calling different retail District and Regional Managers in the Dallas area (as we had compromised that destination for our relocation). I would get them on the phone and tell them who I was and that I was relocating and why they needed to have me on their team. I picked a week for travel, lined up back to back interviews for the time I was in D-town, arranged to stay with my Uncle who lived here, borrowed his enormous Texas truck while here, and set out to drive all over the city for these interviews I had lined up. I believe I had 21 interviews scheduled over four days time…it was intense! I needed to make something come out of my time there, so I prayed that at least one of them would pan out. Luckily more than one did, and the offers still would come after I had already relocated and made my decision. Back to specialty retail I went. In the meantime, I worked for a few retailers (Dallas has no shortage of shopping), had two more children (a boy and a girl) and life kept moving.

My last retail position was with a store that is considered to be specialty but it was enormous and runs a ton of volume, so it is really more of a hybrid between specialty and big box. It was also an absolute beating! Physically, mentally, you name it, it was tough. Also, the Dallas district for whatever reason was a little cult-like in how they did things. To play the game, you had to be willing to give your complete self over to this company and team and their insane ways of doing things. It was kind of a mean girls situation, and if you were at all different or challenged their ideas in any way, they would set out to make sure you weren’t around for long. Well, that was me, for sure. Funny to be hired for your experience and ideas and inevitably be singled-out and targeted for implementing and sharing them. It was nuts! So they did what they do in these types of situations…when they want someone out, but have no real reason to get them out, they set out to use the surprise internal operational audit to catch you and terminate. For me, they came on a day when I was at a doctor’s appointment and they used the trash bags in a fire egress, no-zone (which carried a lot of points on the audit) to cause us to fail and to terminate my employment. Although it was scary and really wrong, I was kind of relieved to be freed from the insane toxicity of that organization. I had small kids at home and was absolutely killing myself to make it work there…if they hadn’t freed me, I don’t know how I would’ve had the courage or energy to free myself.

So, now I was unemployed, which had not ever been the case since I was 16 years old. It was a strange and uncomfortable feeling. And now I was so tired of the grind of retail, I decided to take a moment to think about what to do next. Meanwhile, I had already been applying (because I could sense their evil plan unfolding) and had accepted an interview with an unknown company for the very next day. The job listing was so vague (I know now that was intentional), and I was completely intrigued (which was the exact reason they were so vague). So I headed into this meeting in Dallas, excited to see what it was all about. I walked in, a woman whom I assumed was the secretary, gave me a paper to fill out and escorted me to a larger room with other candidates. We then listened to a very lengthy, definitely boring and maybe a little scattered hour-long pitch from another gentleman. He introduced himself as the Regional Manager. Turns out the opportunity was in health insurance. As he went on and on about things I cared nothing about, I looked at all of the awards on the wall and realized that the woman and man were a married couple. As I noticed the evolution of her name, I gathered that they weren’t married and both worked for this company, probably met while here and had become married at some point in their tenure. After his pitch, he would take candidates in one by one in the order they had arrived at the meeting, and she would ‘work the room’ in order to keep people there. I learned all of this after the fact, but this was the strategy to keep people on the hook, as so many would leave after his sales pitch. Later I would experience many who would say they were going to the restroom and they would never come back. The whole thing had a bit of a MLM vibe to it. But, that day I had all the time in the world, so I let other people go ahead of me and waited until the end to speak to the Regional Manager. In the in-between time, I got to talk to and learn a little about the wife. I found her pleasant and sweet, and I liked her pretty immediately. He, on the other hand, seemed super slick and smarmy, but I thought she made his stock go up.

I found out in my one-on-one that I would need to study for and take the health and life insurance exam. The cost was around $300 for the course and the exam. I would need to get fingerprinted and pass a background check. Once I had my license, I was to call him directly to let him know I passed and they would set up training. I decided that I would go ahead and pursue it since I didn’t have anything else going on at the time. But, as I had really never had any significant time off in my entire working life (unless you count maternity leaves), I wasn’t super keen on getting to work in a timely manner. I took some time, went to KC to visit my family, took my time studying and kicked the ball further down the field for a while! Finally I locked in, took and passed the exam, got the fingerprinting done and was scheduled to start my training in June…my last day of employment was in April, just to give you an idea of how much I had slacked off. In the meantime, I had begun to feel badly about not working, and didn’t ever want my kids to see that I wasn’t hustling, so I took an overnight job at Walmart so I would be doing something! Turned out to be kind of a mistake as the insurance thing would take off quickly and I wouldn’t have time. But, being a person of my word, I stayed with them until the end of the year, as I had agreed to make it through the holiday season. This was all in 2017.

In the meantime, I was learning what I needed to about offering this niche health insurance product. Now, most people struggle tremendously when starting out. Honestly, the deck is stacked against you. It is hard to move to a commission-only job. I was fortunate that I was able to collect unemployment since I had been let go from my previous position. It is tough to find people who have a need for your product. This company really sold you on the fact that they had leads lined up and that they were people who were actively looking for insurance. They made it sound like you would just make a call and the person would be so grateful to hear from you that they would buy and you would get rich. None of this is true! The leads were lukewarm, at best. As is so common in this industry, they gave the hard sell to all candidates…turns out those leaders bonus on getting people to sign-up as sales agents, so their motivation was really just to get anyone they could to say yes. The deception really started in that first meeting, and unfortunately, I found that it continued on from that moment forward. I think that insurance brokers get a bad rap for being kinda smarmy, but the truth is that there seems to be a higher concentration of smarmy people who are attracted to the industry. I found a whole bunch of them at this organization...I had never encountered so many dishonest people in one place...it was intimidating and (in hindsight) terrifying. I felt that there was something off early on, but the checks were rolling in. I truly took to it like a fish to water. When I started, I went out on sales calls (we did everything face to face at the time) with my leader. My job was to set the appointment with the qualified lead, and he was supposed to close the deal. The money would come to me to get me started, and I would learn how to do it on my own in the process. All great in theory, however, I went out on at least 8 or so sales calls with my leader and he closed exactly NONE of them for me. While I appreciated the help and the extensive car time to team build and get to know one another, I was getting a little tired of driving all over Texas with no fruits for the labor. The next appointment I booked, I told him I thought I was good to go it alone and that I would let him know how it went. I sold that first deal, and the rest was history.

I continued to go out on my own sales calls, and very early on my personality gained me a few loyal clients who had vast networks. The referrals started to roll in and so did the large paychecks. I went through my first Open Enrollment (which happened to be the last of the years for the tax penalty for not carrying qualified healthcare), and ended that year the most issued agent in the Dallas office. I was busy all the time and outselling even the most tenured agents. I give the credit to work ethic and retail training. See, I was one of the first at the office daily and definitely the last to leave most nights. All of my years in retail had trained me for the hours. Outworking everyone and connecting with people through my winning personality really paid off in this field. I was hooked! Sure, the money was great, but I really more enjoyed the work I was doing. There was really a need for this service, and I was proving to be pretty great at it.New year, new me, new promotion and new goals! When the year turned, I agreed to take a team. This would mean that I was now the leader responsible for training newly recruited agents. I would be the one running their appointments, teaching them how to sell this product. My team grew quickly and was super close. I had a lot of fun in the early times.In 2019, there was a new agent who signed on to join our office. His name was Dakota Myers. He was this gentle giant, standing at 6 foot 4 inches, and when I first heard him on a sales call, I thought, “This guy is so ballsy on the phones that he is either going to crash and burn or completely set this business on fire.” The results would be drastic one way or the other. Well, the answer is that he initially crashed and burned. However, he is one of the most resilient and tenacious people I ever have met. He had become fast friends with one of the agents on my team, so they would work together sometimes in the evening, and it allowed me a lot of proximity to hear and coach Dakota. He was working so hard and making no traction. I went to his leader and asked him to give him additional help. The guy was putting in the work. I believed he deserved for us to give of our time to help him become successful. Unfortunately, his leader disagreed. He essentially told me that he wasn’t going to give him any more attention than anyone else and that if he made it, he made it. If he didn’t, it wasn’t meant to be. I still felt strongly about the cause, so I went to the District Leader (same wife from the first interview) and asked her to move Dakota to my team...I had never done this before. She obliged and so started my closer working relationship with Dakota.

Through grit and perseverance, Dakota did finally figure out how to present this product and actually make a living in insurance. Fast forward a couple more years, and Dakota had it down pat. Interesting fact about Dakota is also that he is one of the most curious people I have ever met. He loves to dissect and inspect and really get into the nuts and bolts of any business. In context of this story, that means that Dakota was beginning to really dig into the inner workings of compensation and residuals and what it truly meant to sell as a captive agent. He also started to become less-tolerant of all of the potential clients he had to turn away because they couldn’t be covered by that super niche, very stringently underwritten health insurance product. He started to watch insurance videos on YouTube (such a millenial thing to do), and educate himself on what it looked like to be a broker. He met a YouTube influencer (one of many connections we would make in our journey) and asked me if I would like to come to the meeting to see what he had to say. Caring more about Dakota as a person, and less concerned about keeping him on my team, I supported him in his transition to broker. We were still working side by side. He was helping the clients that I couldn’t. It was a good union. But, as typically happens, good things sometimes run their course and come to an end. We thought we could have a brokerage together. I would help the clients for which the niche, captive product made sense; Dakota would help the rest. But, the higher ups at the company I worked for caught wind of the union and terminated my contract. It hurt financially, and I was validated in my thinking that these people were terrible. After arbitration and battling it out with them, I was free from them and moved fully to broker life as well.

As much as the whole thing was stressful and sucked at the time, in hindsight I am so glad that it happened and saved me from myself. I knew I shouldn’t be there. The organization was so crooked and gross that I knew I didn’t belong. But I was making a great living and enjoying what I was doing, both with my clients and my team. Honestly, it was a moral dilemma of the worst kind. I was constantly conflicted about not wanting to make more money for the terrible company and leaders, yet wanting to continue to help the clients and agents who I so enjoyed working with. Honestly, if they hadn’t come in heavy-handed and pushed me out, I don’t know how I would’ve been brave enough to make that move on my own. Their lack of scruples saved me from myself!

Moving to broker life was a simple transition. I simply went to work on a Friday pushing a certain product line and then returned to work on Monday with a whole new breadth of products I could serve people with! And now, I could literally help every single person I spoke to. It was a dream come true.

Now it is 2025, and I am so grateful for the unexpected turn of events. We are growing, building, meeting so many great partners along the way. I have learned so much about this business, and I am so excited for all of the exciting things coming in the future. Dakota and I are a great yin and yang...he is the visionary, I am more the personnel, financial side of the business. He makes up for what I’m lacking, and vice versa. When they say ‘two heads are better than one’, we are the epitome of the expression.

I would just say stay tuned to see all of the exciting things coming soon. We have hit a stride and we are aimed for total world domination. We are thankful for all of the people who have helped us thus far on the journey. We are preemptively thankful for all those we have yet to meet who will also be a part of our success journey. Look out...The Benefits Boss is coming for ya!