OWAHL 006: Thinking of going full time with your business? Here are some things to think about!

Question: "My husband and I would love to entertain the idea of entrepreneurship. While his job is sufficient in providing for us financially, it leaves much to be desired in regard to family life. However, we feel completely stuck at the moment. In addition to a dependable salary, his job also provides excellent insurance coverage for all five of us (dental, medical, and vision). He has a 401k and retirement account that has been funded since he began with the company over ten years ago.

There is a lot to fund financially, and these are all just the basics! How is this done while pursuing entrepreneurship? Are people (entrepreneurs) able to get on top of all these in ways we've yet to discover beyond dependency on a corporate job? Or, are people just going without the future being funded?

Furthermore, how do you fully learn about the local, state and federal regulations and requirements? Registrations and taxes are required of a business.

These are the kind of entrepreneurship questions that are generally not addressed. Having started and managed several successful businesses yourself, what has been your experience in these areas? Have you found any resources that have been particularly helpful? Again, please don't feel obligated to answering anything that may be too personal since these questions do pertain to finances. I appreciate your time in reading and responding to this message."

Getting Started

All this little stuff IS the overwhelming stuff. It's what holds you back. It feels huge and impossible and so scary. And a lot of it we are still figuring out along the way! 

If your husband (or you) works a corporate job with a good income, it can be really really difficult to leave. We gave us all of those things when we took the plunge to be self-employed. 

Years ago, the security of a corporate job made us feel safe. We needed that. Now we've embraced the freedom in being self-employed AND we've started to view our life as a lot more secure, since our business is up to US, and not a huge company or bosses that could change our fate with a pink slip. 

It's a slow process. We built things up on the side first. Jason didn't quit his job on day 1 and then day 2 we tried to figure out an income stream. We tested things out, we built up side income, we knew that with more time and attention dedicated to the business, we could make more money.

So yes, there is a LOT to consider and a lot of different pots that money needs to be funneled into, but those things are simply coming from a different income source. At your job, medical, dental, retirement, etc all comes out of your paycheck. It's just all done for you, BEFORE you see the money and somehow that feels a lot less painful. 

So these are all things to keep in mind when considering the jump! But it is doable. Millions of people are self-employed and figure it all out :) 

Taxes & Regulations

Personally, I think this was the biggest headache trying to figure out. We had to figure out taxes, what kind of company we needed, did we need a business license, what forms need to be filed, etc. 

LegalZoom.com was a huge help to us in the beginning! Because every state (and country) is so different on taxes, regulations, and companies, it's impossible for me to give any advice on how to get started with this. 

They have sections that explain all the different companies you can form from an LLC, to a partnership, to a sole proprietorship and more. We landed on needing to form an LLC and then we were able to file the paperwork with LegalZoom! They help you to file the correct file for your state and everything! 

Our next negotiable suggestion:

Hire a CPA in your state. We have an amazing CPA who specializes in small business and we don't know WHERE we would be without him. When we get a tax form, or want to try something new, we run it all past him and he tells us what to do. 

For what we do, we need someone who is very familiar with online business and our forms of revenue. Our CPA is amazing he helps us with all of that. Yes, it costs a little bit to have him handle all of our taxes but it is WELL worth it. He has walked us through everything. 

Medical, Dental, and Vision

Yes, this is another headache. And again, this depends on what state you live in. 

We ended up with a sharing company. Medishare. 

Dental and vision not worth it. So we pay out of pocket. 

Savings & Retirement Accounts

These are all totally doable, but you just need to do a little work to get them set up. We are actually in the middle of setting up these accounts. But again, a good CPA can help with that!