3 Fears I Had About Becoming an Entrepreneur, and How I Overcame Them

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A City Meetup speaker shares her past fears about becoming an entrepreneur and her solutions to overcoming them. 

By Reva P. Minkoff (Founder & President, DigitalGroundUp Inc.)

In many ways, I consider myself an “accidental founder.” I sort of skipped the wantrapreneur step. I didn’t sit around with an idea for years waiting for the right moment to pounce. I didn’t even aspire to be an entrepreneur. I admired the people taking the leap, but personally, I wanted a safer path – to be someone else’s CMO or COO or something.

There were a lot of things that were unappealing or scary to me about entrepreneurship, but I figured out how to get past them. Now, after nearly two years as the sole founder and president of two different companies simultaneously, Digital4Startups and DigitalGroundUp, I’d like to pass some of that advice to you.

Freedom is Scary, So Make Sure You’re Accountable

I was very afraid that I would be unproductive having the whole day to myself. I work best under time pressure and am deeply concerned with the opinions of others. But I realized that by building a team with stakes in the company and my leadership, I gave myself the accountability that I needed. No matter how much of the company I own, it was a big wake up call for me when I realized that for my employees, the company was a lifeline. I can’t fail for me, but they’re also counting on me too. That helps keep you grounded.

Money and Accounting Can Be Scary, So Tackle Them Early

I used to say that I hate accounting and didn’t get it, but after starting a business and spending many hours in the books, I’ve realized that accounting can actually be enjoyable. That said, it’s also an area where I’ve made a lot of mistakes. Most entrepreneurs won’t be familiar with accounting coming in, so as soon as possible, be sure you get someone on your team either officially or unofficially who is. My accountant has been a godsend in teaching me how to keep books, but my friends who are certified public accountants and two people I know who understand accounting from the point of view of business people have been equally as invaluable.

I didn’t realize how many taxes and filing fees there would be, so make sure you’re keeping at least 40% of what you’re making to the side for taxes. Taxes for businesses are due before April 15th or sooner (and if you don’t, you have to pay penalties). The more on top of what you’ll need and when you’ll need it you are, the better you’ll be able to avoid “surprises.”

Building a Company “On Your Own” Can Be Scary, So Make Sure You Have a Great Team

As previously alluded to above, a large portion of both our success and my sanity can be attributed to the amazing team that surrounds me and works with me on each of the companies. Even though we don’t have a huge team, everybody we talk to, whether it’s officially or unofficially, brings a lot of value to the table.

Even though we don’t have a huge team, everybody we talk to, whether it’s officially or unofficially, brings a lot of value to the table. From the friends who’ve offered to go out for dinner or drinks after a particularly rough day to my officemates who are always brimming with good advice to our art director who is always ready and able to turn around great work with short notice, my company may be “mine,” but it is also “ours.”

So make sure you surround yourself with good people whom you trust. You’ll learn from them, they’ll learn from you, and the company will be more successful as a result. No one can accomplish something like this all alone.

And it’s really not that scary after all.

Reva Minkoff spoke at Women 2.0 City Meetup. You can register for the next City Meetup here.

Reva Headshot Oct 2013 (1)

About the guest blogger: Reva Minkoff is the Founder and President of DigitalGroundUp Inc. and Digital4Startups Inc. DigitalGroundUp won 2nd place at Chicago Booth’s SeedCon competition and was named a finalist in the Chicago Interactive Media Association’s Digital Startup Initiative. Reva was named The Founder Institute’s Female Founder Fellow, a distinction awarded to the most promising female applicant to the Founder Institute.