How i made $20,000 in one day in the Insurance Industry

Here’s a story for the books! Back in 2015, I had just sold a small business and it left me looking for a new opportunity. I was approached by a friend of mine that showed me some of the opportunities in the insurance business. She explained all the different ways to help families and how it could be a very lucrative business if you apply yourself and put the time in. I was very interested, but wanted more information and wanted to meet some of the people in that organization that had been killing it. I always like hearing it from the top producers. Come to find out, the company was actually a marketing agency that provided leads, coaching and many other things to help it’s team members grow their own business. The only thing I had to do was get a license. Well, here I thought that would be manageable, but it was actually troublesome for me. It took me three times to just pass the state licensing test.  Now that I had my license, I thought I was ready to go to the top. I was “gung ho” for sure.

I started studying up on the products to offer and practiced scenario numbers on my laptop. I finally jumped out there and started purchasing leads that the company offered and actually got a few deals here and there. I continued to dive into all the training calls and went to as many company meetings and conferences that I could possibly attend. Over time I kept running into colleagues that were making the kind of money I wanted to make and I would always ask them more and more questions about what they would do to close so many deals. As always the answers were basically the same. Read, be on all the calls, go to the meetings, know your products and schedule appointments and repeat. It took me a while for it to sink in that that’s it. I finally gave in and it worked.

During this time period, I consumed every business and sales book I could get a hold of and went to every meeting that I could go to and attended all the conferences. I was on most of the company calls each week. I was a sponge. This was an incredible process for me as I was learning and growing at a faster pace than ever before in my life. I quickly started booking more appointments than I could actually handle. I was running on all cylinders and loving it. I was getting deals and it was consistent. I knew I was gaining more and more momentum because I had totally transformed my mindset with all of the reading and being around like-minded people that had a passion for winning. 

How it happened

During the time I was all-in on transforming my mindset. Every week, I received another set of leads and called everyone up and set up my normal route for the weekend. I set out that Saturday to hit several appointments and I noticed one of them was in a very affluent neighborhood in Atlanta. As I pulled up to this particular home, I understood it to be a multi-million dollar house. So, truthfully I said to myself that there is no way these folks will buy anything from me. I was assuming that they already had everything covered or had their own financial guy that took care of everything. I knew that this home was just going to be practice for I thought to myself, “ I should still go ahead and go through my routine and see what I can offer them”. It was an older gentleman and we sat in his living room. I had my laptop out going over a few scenarios based on his age and what coverage amounts he was looking for. I gave him a few numbers almost hesitant to even say the premium amount because I had never even looked at a number like that before.

I finally got it off my tongue and he didn’t even flinch. He paused for a minute and then asked if I could meet him the next week at one of his businesses, which was basically a horse boarding farm about 45 north of his house. He told me he was going to have his business partners there as well to possibly look at a policy to cover each one in case something happens to any one of them. So, I agreed. Still, at this point, I didn’t think too much about it. I figure once all of them hear the pricing, they would just get their financial advisors to get the same thing. So, I went on out the next week telling myself again that at least it’s good practice.

I arrived at the farm and sat down with all three and about an hour later I had quoted out for all three and the main business owner looked at me and said: “Write it up, let’s do it”. I sat there going through the application for each one and then got the check for each one and was quickly on my way out. I told them I would be in touch in just a few days with more information to give them about each policy. Then I headed back home and as I was driving, I realized what I had just done. I did some quick math in my head and realized that I was about to get $20,000 in commissions from this one deal. I was blessed to have this opportunity but also realized that I could have easily not closed this deal because of my mindset going into it. Even when your mind is not in the best place, deals can still happen. It doesn’t always happen that way and that’s why it’s so important to get your mind right. 


The lesson in the story is to never judge a book by its cover. We have all heard that before, right? This particular experience was a big breakthrough for me in my life and sales journey. Always be ready and have the certainty that everyone you encounter will be an opportunity in one way or another.


Shawn Greenway, CEO