We can Insure Your Universe in these States....

"Solid in every way. Experienced and knowledgeable, but also very reliable." 

— Pinnacle Mortgage

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       Commercial Insurance     


“Steer clear of Developers”, is the advice given to most insurance agents. “They’re complicated, time consuming, and only execute 50% of the projects they discuss with you.” The insurance sages were only wrong about the percentage. I’d say it’s closer to 20%. But it’s a fun and adventurous 20%! As far as the rest of it goes, we like the challenge. Multi-Family Wrap Projects, P3s, Condo-Conversions, Tract-Housing, Hotel/Motel, in a flood zone, polluted soil, you name and we’ve handled it.

Real Estate


Whether your asset is Multi-Family, Office, Industrial, Retail, or Vacant Land, UPSIDE has the experience and relationships to handle your account. Our clients range from owners of single properties to portfolios with values in the hundreds of millions.  


This industry continues to grow aggressively and the insurance companies interested in partnering with our clients are just as aggressive. Economies of scale are strongest when there are 7+ locations. This will be experienced from a cost perspective as well as the capacity to implement risk management strategies. 

Work Comp

Work Comp is an animal all it's own. As a federal mandated coverage it's less about the complexity of coverage language and mor about how you and your agent can navigate claims, EMOD calculations, loss reverses, safety programs (and no the safety manual you downloaded from LegalZoom does not count as a "program"), and risk control. We trudge through that mud with you until you end up with a clear plan moving forward. 


Here's a few google forms. Fill out the one that best represents the real-estate asset class that you're looking to insure.


Personal Insurance

Insuring Your Universe...


Auto | Home | Life   

Umbrella | Recreational 

  About Upside   

Who is Upside Insurance Services?

We are an insurance broker that is contracted with 40 different insurance companies to be able to offer a customized insurance product with the most competitive rate available. 


Here are some well respected companies that we currently work with: Travelers, Hartford, Liberty Mutual (Safeco), State Auto, Nationwide, CNA, and Pekin.  With Upside, we will be able to help clients choose the right company & coverages for them, and it will be at a phenomenal rate as well.

Why use an independent broker?

Insurance rates are constantly going up and down. As your broker, we will encourage you to review coverages every few years. During those reviews, we will make sure your coverage limits are where you want them to be. We also will want to make sure that the company you are insured with has the most competitive rate.  

Why would my insurance coverage change?

A few examples that change coverage needs are having kids, kids moving out, new cars, home improvements, retirement and promotions at work. All these life changes will affect the amount of coverage you need from life insurance to your home insurance. We want what is appropriate for make sure we protect your universe. 

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Drew Cottrell

Commercial Insurance

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Chad McFarland

Personal Insurance

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Commercial Insurance


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Megan Cooper

Personal Insurance

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Debbie McErlain

Commercial Insurance


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Adrienne Ferro

Commercial Insurance


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We're looking for people who are intelligently hardworking, driven morally, and encouragingly creative. Send us an email if you're interested in joining the team.


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