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James Underwood

License #: 18607458
4.9 OUT OF 5 STARS
star star star star star (50 Reviews)
Christopher Draegert
License #: 16765125
4.8 OUT OF 5 STARS
star star star star star (95 Reviews)
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About James
With over 6 years of industry experience, I am committed to providing my clients with accurate insurance solutions, informed decision-making, and competitive rates. I take the time to ensure that my clients have a comprehensive understanding of their insurance coverage and explore all available options. As an independent agent, I have access to an extensive network of 40+ insurance companies, allowing me to thoroughly shop rates and find the best fit for my clients' needs. My passion for insurance extends beyond my professional life; I am an insurance nerd who stays up-to-date with the latest industry trends and regulations. My goal is to empower my clients by equipping them with the knowledge they need to make confident insurance choices. Trust me to guide you through the insurance process, providing meticulous attention to detail and unwavering dedication to your insurance protection.
States Licensed In: IL, WI
About Christopher
With over 10 years of industry experience, I am dedicated to providing exceptional insurance services. My priority is to ensure that my clients have a clear understanding of their insurance coverage and available options. I believe that informed clients are empowered to make better decisions. As an independent agent, my access to an extensive network of more than 50 insurance companies, paired with my in-depth knowledge of the insurance industry, enables me to identify the most suitable solutions tailored to my clients' unique needs and budget. Insurance is not just a profession for me; it's a passion that I live and breathe every day. With my commitment to outstanding customer service, backed by Goosehead and our amazing support, I strive to make the insurance process seamless and transparent. Trust me to be your insurance advisor, guiding you towards comprehensive coverage that protects what matters most to you.
States Licensed In: IL, WI
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100 North Waukegan Road, Suite 209
Lake Bluff, IL 60044
Languages spoken:
English
Hours:
We’ve got you covered,
and then some.
  • Homeowners Insurance >
  • Auto Insurance >
  • Flood Insurance >
  • Renters Insurance >
  • Condo Insurance >
  • Landlord Insurance >
  • Motorcycle Insurance >
  • Boat Insurance >
  • RV Insurance >
  • Life Insurance >
You probably looked at several houses before you found the right fit; why not look at home insurance the same way? Goosehead does the looking for you, and finds the policy that fits your needs and budget, without compromising coverage.
It seems like there’s as many car insurance companies out there as there are cars. Lucky for you, Goosehead looks under the hood of all those policies to find the right coverage for you and your ride. Think of us as your roadmap to better protection and better rates.
Having the right amount of protection in case of flooding is important. That’s why our Goosehead experts will do all the research for you. We’ll compare dozens of plans and choose what’s best for your residence, and your budget.
Sure, you may not own the building. But you own what’s in it. If a fire or disaster would cause a major setback, take a close look at renters insurance. Better yet, let us do it for you. We’ve evaluated products from dozens of the most respected insurance companies to help you home in on the right policy.
From an insurance standpoint, high rises, townhomes and condos can be, well, a little different. HOAs cover some parts of the property, leaving other areas up to you. We can help you find a policy that provides the coverage you need — at rates you’ll feel right at home with.
A rental property isn’t the same as a primary residence. Without proper protection, a landlord might be personally liable for damages from accidents or other events. We can help you determine the right coverage for your rental properties and compare rental property insurance quotes so you can operate with total peace of mind.
Driving a motorcycle is all about freedom. Speaking of freedom, there’s no need for you to spend end less hours of your free time comparing insurance plans. Comparing the best motorcycle policies from the best insurance companies to get you protected the way you should be protected, at the price you deserve.
Chances are you bought a boat for a little rest and relaxation. Goosehead makes shopping for boat insurance just as relaxing. Our expert agents will shop dozens of policies and find you the right protection, at the right price, that will really float your boat.
Your RV lets you escape to the open road. And with Goosehead, you can escape the usual time commitment of buying insurance. Our expert agents do the research for you, comparing dozens of policies and choosing the right protection for you and your home on wheels, all at the price you deserve.
As the saying goes, life happens. But sometimes it happens in ways we don’t expect. For all the great times, and the more difficult times, Goosehead can be there to make sure you and your family are prepared, and protected. If something happens to you, the right coverage will ensure your family is financially secure and well taken care of in your absence.
SPECIALTY INSURANCE
Umbrella Insurance 101
Umbrella insurance goes beyond your normal limits of liability to protect you and your family in the event of a sudden and serious situation. Relatively cheap, umbrella policies can offer additional coverage for things like injuries to others, legal fees and litigation, excessive property damage, and other personal liability situations.
HOMEOWNER INSURANCE
Homeowners Insurance 101
You found a property you love, you managed to save a down payment, and you got approved by a lender. Now you need to find a homeowners insurance policy that meets your needs, but how do you know if a policy is the right one for you?
AUTO INSURANCE
Auto Insurance 101
Most states require you to carry auto insurance. But how do you know if you have enough? A basic understanding will equip you with the knowledge you need to make smarter decisions when selecting your auto insurance policy. Let’s get started! 
HOMEOWNER INSURANCE
Water Coverages Explained
Four different types of water coverage may or may not be part of your home insurance policy. Let’s look at how they could help better protect you and your family from financial burden due to various causes of water damage to your home.
Recent Reviews
Total Agency Reviews 145
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Elizabeth R., Jun, 25 2024
James was incredibly helpful explaining all details of the policy and was very honest and up front about recommending the best option at the best price!
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Amy S., Jun, 24 2024
Christopher was very helpful and thorough in helping us to find car insurance for both of our vehicles at a very cost effective rate. We are on a tight budget, but also want to know we are covered well in any case. Christopher has a wealth of knowledge and got back to us in a very timely way. It was such an easy process and transition. Thank you!!
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Onkarjot G., Jun, 13 2024
Chris is very knowledgeable and was great to work with.
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Catlin P., Jun, 13 2024
Christopher was extremely helpful and made it a breeze to get through!
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Monica B., Jun, 11 2024
The communication and explanations were wonderful and at no point did I feel embarrassed or uneasy.
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David T., Jun, 01 2024
Very polite and eagerness to help, answered all my questions and a feeling of true caring in help me with the best policies
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Karen A., May, 25 2024
Very nice and very professional
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Samuel C., May, 24 2024
Christopher and James are great!
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Sandra S., May, 16 2024
Good communication and comment.
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Kimberly N., May, 12 2024
James was easy to work with and explained all of our options to us very clearly. We were able to save a sizable amount of money while keeping the same coverage.
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Jacob C., May, 02 2024
Christopher was wonderful throughout the entire process, what you want out of an insurance broker is a true “nerd” about it and from someone who is a nerd about payroll and taxes myself, I can recognize his passion clearly!
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Jincy J., Apr, 25 2024
It’s vey comfortable and useful
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Trevor S., Apr, 24 2024
Customer service
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Taylor J., Apr, 16 2024
James has Incredible communication and a clear passion for insurance! Extremely helpful and was able to find the best policy with a great price for us! Would recommend 10/10
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Timothy H., Apr, 14 2024
Chris was friendly, very responsive, and found us a great deal!
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Barry C., Apr, 07 2024
Christopher explained things with great details. He managed to get me more insurance coverage and renters insurance at a rate lower than my current insurance.
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Kelly P., Apr, 01 2024
Christopher called me on Easter morning to help get my policy set up to start the next day. He was super helpful, informative, and very professional and personable.
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Ryan R., Mar, 28 2024
Honest and straightforward!
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Megan P., Mar, 21 2024
Helpful, informative and knowledgeable
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Janet L., Mar, 17 2024
Christopher is easy to work with. He is very knowledgeable about all the products out there and what best fits for us.
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Dorene S., Mar, 16 2024
Excellent ang highly knowledgeable with a focus on customer service
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Keith B., Feb, 24 2024
Chris Dragert is a guy that I will recommend anyone who needs insurance. I don't say that lightly. He helped me get what I wanted it's such a reasonable price. You are so lucky to have a person like him to work for you.
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Nestor V., Feb, 10 2024
Very happy with the service, I wasn’t expecting the agency fee.
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Peggy A., Feb, 10 2024
James explained every thing and answered all my questions.
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Sean H., Feb, 08 2024
Christopher gives great service!
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Shon P., Jan, 31 2024
Chris is the best he was my agent for years in the past happy I to be back with him
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Glenn B., Jan, 17 2024
I was very impressed with Mr. Underwood's insurance knowledge and professionalism.
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Rebecca B., Jan, 16 2024
We were given great service in our initial meeting, were quite satisfied with prices quoted, and look forward to a good rapport with the team going forward.
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Kimberly L., Jan, 14 2024
James was very friendly, very knowledgeable, and he gave a lot of advice that we've never gotten from any other agent.
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Shanika S., Dec, 31 2023
I received excellent customer service from Chris in addition to securing better coverage and saving money!
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Elizabeth R., Dec, 25 2023
Chris was wonderful to work with. He gave us all the information we needed and asked about, and provided high quality customer service.
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Gerald H., Dec, 07 2023
Great service and knowledge and didnt stop till he found the best costs for my needs
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Mary L., Dec, 06 2023
Christopher Draegert was a pleasure to work with!
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Cheryl J., Nov, 02 2023
He made it fast and easy with great rates
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Yvette M., Oct, 26 2023
Chris explained the details of the policy, cost, recommendations etc., so I understood very well. I have already referred someone to him!
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Dale S., Oct, 26 2023
Excellent service and great products
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Hannah D., Oct, 24 2023
Very thorough and professional. Thank you!
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Denise S., Oct, 23 2023
Efficient service, friendly & knowledgeable agent
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Abram D., Oct, 22 2023
Personalized attention
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Jessica S., Sep, 27 2023
James is great!
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Andrew C., Sep, 15 2023
James was awesome. He was knowledgeable, informative, and sincere in his desire to get me and my family the best coverage possible. He is a fantastic representative of your company and has secured my business for all future needs. Thank you!
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Rebecca P., Sep, 14 2023
I had some frustrating experiences in the past, but James made the process easy and enjoyable. He was thorough and explained everything to me. I feel supported and well informed!
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Eric H., Sep, 12 2023
Knowledgeable
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Koonal P., Aug, 25 2023
Simply put - because of Christopher Draegert ! He was so personable and really took the time to explain things to me. I could tell that working with Christopher meant that I was forever now part of the flock, and that means we're protected and can go to sleep at night much easier. Thank you Christopher for all your help and assistance!
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Thomas L., Aug, 14 2023
Chris was knowledgeable and helpful, able to answer questions quickly and personably.
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Katie L., Aug, 12 2023
Seems very good. The rep was very knowledgeable
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Jason C., Aug, 12 2023
The process was easy and saved me a lot of money. James was helpful and did a great job of explaining everything.
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Geraldine C., Aug, 09 2023
Christopher Draegert was patient, thorough, very knowledgeable.
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Mark S., Aug, 09 2023
Excellent communication, fast response, all boxes checked on service and pricing. Thank you!
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Tracy T., Aug, 08 2023
Very knowledgeable and explained everything in detail instead of just saying this is what we quoted you and here’s your policy
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Timothy R., Aug, 06 2023
Great guys 👍
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Steven Z., Jun, 05 2023
James was incredibly easy to work with and is very good at explaining different things on both the auto and home insurance side of things.
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Bridget O., Jun, 04 2023
Chris Draegert is more excited and knowledgeable about insurance than anyone I have ever met! Glad to have someone like him helping us out.
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Ardene K., May, 31 2023
James Underwood was very thorough in researching insurance companies for me to consider. Also, he’s great with follow up.
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Raymundo Z., May, 30 2023
Great Customer experience and all the options really explained in detail. Thanks
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Michael F., May, 30 2023
Chris’s knowledge on the topic. Shortly into my first conversation with him I could tell he was a credible source of info.
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Kane A., May, 30 2023
James and Chris have been long time friends who I trust with not only my life but my insurance. They do not sugar coat what is or is not on policy and compare insurance to similar life experiences for the naive person who have yet to buy insurance. Ten out of ten use them.
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Tonya S., May, 11 2023
My representative, Christopher, was helpful beyond words. A first time home buyer, I was full of questions but didn't want to be overloaded with information that I wouldn't be able to process. Christopher was timely and crisp in his defining of my insurance needs and choices.
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Elyse S., May, 02 2023
Chris got me a great deal for both auto and homeowners insurance. He did all the leg work of calling the company's and working with my lender. Great experience!
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Linda O., Apr, 26 2023
Competitive rates, responsive, easy to work with, friendly
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Patricia T., Apr, 26 2023
Goosehead provided all the information for our insurance needs in Winthrop Harbor, IL. They provide all the information so we could make the best decisions for our new home.
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Thomas L., Apr, 24 2023
Chris explains everything very thorough and is a pleasure to talk with
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John T., Apr, 24 2023
Mr. Draegert is extremely knowledgeable. He makes complicated financial transactions easy to understand. He also has built a strong network. This allows his customers to talk to him to solve most financial transactions.
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Shawn B., Apr, 16 2023
The agent
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Amybeth B., Apr, 16 2023
The friendliest of the agent
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Alec S., Apr, 12 2023
Chris went above and beyond in helping us as first time home owners getting the best plans for us! Also, got our car insurance into a great rate with a complicated situation!
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Brett B., Apr, 09 2023
James Underwood was hands down the most helpful person I've ever delt with dealing with insurance. He took the time to thoroughly explain everything and even things after that I was unsure of he went into even more detail. I don't even personally know James but after talking on the phone with him and the way he treated me made it felt like I was dealing with a long time friend. I'm very happy I was able to stumble across Goosehead and even more greatful James was the one I spoke with. I'm sure this was a long term move for me as well. I thank you again for the smooth painless crossover. Sincerely, Brett Brenner.
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Christine C., Apr, 03 2023
Chris explained everything and helped me understand the process.
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Austin G., Mar, 31 2023
Christopher was amazing, very educational and super helpful.
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Ana G., Mar, 29 2023
Because Christopher knows about what he is presenting to you, which makes you confident about making the right choice. He will also always be looking for the best options not only making sure we have the best coverage but also a good deal as in terms price.
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Heather R., Mar, 23 2023
The process was smooth and easy. Everything was explained perfectly.
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Daniel S., Mar, 17 2023
Chris was very knowledgeable and provided prompt answers to my questions.
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Jennifer L., Mar, 07 2023
Christopher was very easy to work with. He made suggestions that work best for our family. Looking forward to continuing to work with him.
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Dustin M., Mar, 03 2023
Chris was extremely helpful and patient throughout the entire process! He explained everything about my current and new policy with me and talked me through each step! I would highly recommend him anytime!
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Laura H., Mar, 03 2023
Informative, clear and kind. And fast!
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Kyle O., Feb, 28 2023
Not only was James polite and positive but knowledgeable! He would have answers to my questions before I even asked them. 10/10!
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Lori M., Feb, 27 2023
Christopher Draegert was amazing! Fast and very detailed. And the price could not be beat. Trust me, I shopped around.
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Amy H., Feb, 17 2023
James was great!
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Adam H., Feb, 17 2023
James was fantastic! He not only helped me save some money on my policies but took the time to go over every coverage type that made sense for me and my family.
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Maribeth W., Feb, 16 2023
James was very helpful in finding me a better rate. Very knowledgeable about insurance
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Steven L., Feb, 14 2023
Chris really knew his insurance- better coverage less money and love covered for 12 months.
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Christine M., Feb, 13 2023
Throughly explained all aspects of the policy. Able to answer all my questions and concerns. Wonderful personality.
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Maria S., Feb, 12 2023
very good customer service
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Eden M., Feb, 12 2023
It was a pleasure talking to Christopher for 2 reasons....very competitive rates, but moreover honesty and simplicity going to every detail of insurance. Definitely I'll call him again.
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Kelan S., Feb, 03 2023
James was very knowledgeable and enthusiastic throughout the whole process.
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Paul D., Feb, 02 2023
Excellent customer service and knowledgeable in their field, would highly recommend.
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Manus R., Feb, 02 2023
Very helpful, saved me lots of money
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Pawan K., Feb, 01 2023
Excellent Advise on Insurance selection and reasoning behind it by providing competetive pricing.
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Kerry A., Jan, 25 2023
James, you were awesome and thanks for all the help and taking the time! Kate will be calling you when she is ready.
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Courtney B., Jan, 07 2023
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Jack H., Jan, 01 2023
I was able to get better homeowners coverage for the same amount of money and save on my auto. Chris did a great job and was very informative.
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Nicholas N., Dec, 28 2022
Christopher is a fantastic agent. Incredibly knowledgeable and enthusiastic about insurance. He knows his stuff.
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Kelly A., Dec, 27 2022
Christopher easily is the best insurance agent I have ever had. He researches, listens very well, and customizes insurance to needs. This is no "one size fits all," this is a great human taking time to listen and help. I will readily refer him, as I know he will take great care of whoever I do refer, and they will get great insurance based on their specific needs!
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Gregory A., Dec, 14 2022
Chris was wonderful, spending time actually analyzing our needs and presenting in a way that we felt he was looking out for our best interests in every way.
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Jodeen G., Dec, 11 2022
James was friendly and helpful. I will recommend
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Irmgard K., Dec, 10 2022
Christopher is really easy to work with and knows a lot about insurance. I appreciate him taking the time to go through the policy and coverage with me. Highly recommended!
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Adam J., Nov, 29 2022
This company is great and Christopher is awesome.
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Jordan Z., Nov, 29 2022
It was very easy to get switched over and I feel Christopher hit the ground running with all our needs! We are sort of a special difficult situation and he handled it quickly and effortlessly. I look forward to never having to deal with anyone again and we have found our forever company!
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Jason R., Nov, 12 2022
Customer service
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Salina S., Nov, 10 2022
I've never sat down with anyone who is as knowledgeable and thorough about insurance as we are.
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Salvador S., Oct, 22 2022
I know, Chris for a long time and he is a very good person. If you want honesty and good services Chris is the best.

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