The Startup Project: OLEO Part 4 – The Worst Part About Starting a Business

The freedom owning a business provides is one of the greatest things about starting your own thing.

Figuring out all the back end details is probably the worst thing about starting a business.

I feel like I’ve been blessed in my life with a very solid big-picture look at life. This is good when creating the leadership and vision plan for a company… but it hamstrings you when you inevitably have to dive into the gritty details — which I hate doing — especially details relating to insurance, legal issues, merchant accounts, payroll, and anything relating to these critical but time-consuming and detailed tasks.

I had decided on a direction and vision for Oleo, validated the idea enough to know it was worth spending time and money on, but there was a ton of back end stuff to set up and figure out. I had a TON of questions, among them were:

How am I going to pay employees? W2 or 1099?

Should I incorporate as a LLC or S-Corp?

Which accountant should I pick and how much should I pay for the services?

Do I need a waiver? What should it include? Who should review it?

Do I need a lawyer? How much does that cost?

How am I going to process payments? Which merchant should I use

What about Insurance? Worker’s Comp? Does it cover employees? Damages to customer vehicles?

This list peels back the curtain a bit of how overwhelming the whole process is when you look at it as a whole. There were many more questions than this that I needed answers to. So what do you do when you’re not sure where to start?

You start with one problem. And you solve it.

Then you move on to the next problem. And you solve that.

I picked up the phone and called an insurance company to get quotes on insurance. I e-mailed several accounting firms and asked friends for recommendations. I talked to several different merchants and compared prices.

No matter how successful you get, you never really run out of problems — you just upgrade your problems to better ones. Warren Buffet has got problems, he’s just got better problems than you and I.

I’m no expert on this stuff, but my advice is if you’re feeling stuck or spinning your wheels, just try accomplishing one task. Get that one thing out of the way, build some positive momentum, and remember to BE PATIENT. Sometimes you have to go through the shit to get to the caviar.

I didn’t want to get into the tight details for all of the questions above because its BORING, but if you are curious or have specific questions about any of these processes I’d be happy to help!


Thanks for reading,







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