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Meet Theodore Carpenter of AutoMatic Insurance Services in Wrigleyville

Today we’d like to introduce you to Theodore Carpenter.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
Around 20 years ago, I became an independent insurance broker. Shopping around for folks I noticed the huge discount you get for buying a high deductible plan, and it gave me the idea of packaging insurance plans together. I’d put a $2500 or $5000 deductible with supplemental plans like accident and critical illness to offset the higher deductible.

A typical case would have a major medical plan, an accident plan, a critical illness plan, and a health savings account (HSA) contribution. If they needed a doctor’s office visit or relatively small bill they could use their money in the HSA to cover it or make monthly payments to the doctor with it. That money they contributed also reduced their taxable income by the amount they contributed annually. This was all for the same or less than they would have been otherwise been paying. Except for in my plan design if they stayed healthy the HSA contribution goes to their savings account instead of the insurance company’s pocket. I also made it so they could write one check for all of it so that it was seamless to them. In many cases, folks didn’t have many claims and their HSA contributions started to add up pretty quickly. This allowed them to take even higher deductibles over time further reducing their premiums as their HSA savings were building up. In one example, the person saved $20,000 over what they were currently doing at the time they signed up with me. In 2013, I founded Automatic Insurance Services, Inc, and negotiated with Compass Health Professionals, a health concierge company, for all my Automatic customers. Compass facilitates in helping my customers understand and use their benefits as well as looking to make sure claims are processed properly. Now with under 65 healthcare all messed up it’s more important than ever to have someone represent you that knows what they are doing.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It’s been very difficult. I had two different business partners, each one lasted 3 years separately, before I started Automatic Insurance. The two partners were primarily large group health administrators, and after a while my business model didn’t fit theirs, and just we had to part ways. Finally, I met a man at an insurance meeting, and I got to know him pretty well.

He was hearing of my struggles and kindly lent me $5,000 at low rate of 10% to start the business. Finding a bank that will think outside the box, and work with a small business like mine has been a huge battle the whole time. Through all of that, the business is now running stronger than ever. Learning all the new healthcare law ins and outs has been pretty tough as well.

AutoMatic Insurance Services – what should we know? What do you guys do best? What sets you apart from the competition?
AutoMatic Insurance Services, Inc solution provides a turnkey alternative to standard individual health plans. Automatic Insurance combines the insurance carrier’s premium with outside expenses into one fixed, monthly payment, making budgeting for their healthcare – well, AutoMatic. Having a fixed monthly payment helps users control the unpredictable costs of standard plans because these expenses have already been factored in. No more worries about the upfront cost for doctors’ visits or diagnostic tests, allowing you to deal with your real concern which is your health. Even more exciting, early diagnosis normally means a great prognosis and hopefully saving lives.

Automatic Insurance helps users not only prepare for unexpected healthcare costs, but potentially helps them save for their retirement. Automatic Insurance deposits a portion of the monthly payment into a user owned savings account providing the incentive to use their insurance judiciously, plus an opportunity to save a ton of money. The balance, after claims are paid out, rolls over towards next year’s health budget. However, if a user stays relatively healthy, they may use the excess money saved over the years, towards their retirement at age 65. What standard health insurance plan has that? NONE!

Automatic Insurance’s primary goal is make the use of healthcare plans virtually painless.

We also do Medicare, life insurance, and long term care as well so we are a one stop shop for all your insurance needs.

What moment in your career do you look back most fondly on?
June of 2013 when I opened the company that I had been dreaming about for years, but I was always hampered by my partners. Also, the first time that my customer’s health savings account built up to the amount that they could purchase long term care included in the price they started with for just health insurance alone. I knew I was on to something.

Contact Info:


Image Credit:
Bill Rancik Meeting in Chicago at Capital One Cafe on small business.
Compass Photo and luncheon with Dr. Bricker founder of Compass Health Professionals: Frieda and I were at a Compass luncheon Symposium in Chicago.

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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