Potential Newbie Insurance Questions


New Recruit
Met an expediter several months ago while at a dirtbike ride and he enlightened about the expediting world. Since, I've been seriously looking into making a swap from my current soul sucking job and have been asking my new found buddy all sorts of questions so figured I'd give him a break. I'm 25 and my first full time job was/is W-2 so the 1099 switch includes many new components and I've been struggling trying to gather useful info. Making the switch will make me drop all of my healthcare/ HSA, 401k benefits so I've been struggling trying to figure out cost of different insurances and unknown costs. I have a gig lined up if I want it, but want to clear up all of the unknowns prior to dropping $$ on a van.

1). Healthcare: I'm planning on using the state marketplace to find the most affordable coverage. Any other recommendations would be great, and estimated monthly cost of healthcare would be even better so I can budget to see if expediting will be worth. Most health care premiums are based on estimated annual salary which varies in this industry and I have no experience so trying to get accurate #'s has proven best guess.

2). Auto Insurance: To get a van insured do you all use business auto insurance or personal auto insurance? I'm assuming business, but since it would be my only vehicle it would be a mixed use when I'm not on the road. Non-trucking insurance would cover the cost of the personal side of things, right?

3) Any comments on need for disability insurance? I'm definitely a 'Better safe than sorry' guy, but wondered if there were other options available to ind. contractors.

4). Occupational Insurance: I have a job lined up if I want it and they have a policy available for $35 a week. Would this eliminate a need for disability insurance?
5).They would also pay cargo insurance and non- trucking insurance.

Lastly, any other expediting specific policies I am missing that I will absolutely need? Any gap insurance I should look into?

Thanks for any feedback. P.S. I've done a good bit of research and read previous forums so I'm asking for additional info since I couldn't find a ton of useful input. Not being lazy w/ all the questions.


Veteran Expediter
Charter Member
Retired Expediter
US Navy
1st thing I would do find good accountant , to go over all the taxes. Talk to people at OOIDA, they have a lot of good programs for insurance and others things. .To see if joining OOIDA would fit for you. Also look at wanted ads on here there are people looking for someone to drive there trucks. Try driving for some one before jumping in and spending a lot of money. . I drove for Roberts Express/Fedexcc, , CEVA . Was owner operator for 25 years. Also do out side sales at Tysinger Motor Company , Hampton , on Sprinter Vans . send me your phone number in pm and be willing to talk to you. drove straight trucks for 11 years, sprinter van for years 14


Veteran Expediter
Retired Expediter
For insurance there's CIS, one of the long time members and advertisers here on EO, and then there's everyone else. They can answer all your questions and can make sure you get the CORRECT insurance coverage.