Why all Entrepreneurs Need a Team (Whether They’ll Admit it or Not)


When I first started out as a (part-time, evenings-and-weekends, lunch-break) small business owner, everyone seemed to have advice for me. From what type of legal entity I should become to when I should consider space and overhead to how I should look for clients. One fairly consistent suggestion I heard from more seasoned business owners was that I should start putting together my "team."

As a first-child control freak who always hated group science projects, the idea seemed kind of foreign. Slightly preposterous, even, since my whole vision of running my own business involved sitting behind my computer or my printing press, silently shuffling out designs and orders, and not relying on (or being disappointed by) anyone.

Over the years, however, I have come to realize that I, in fact, do not know everything. Trust me, this was a shocking revelation. If you haven't already come to this conclusion yourself as a small business owner, you will. You will have to. Here are some of the most important people to start collecting for your "team," plus what roles you should have in mind for them come year one and year five.

1. Accountant. Year one: Quickbooks is fun! Reconciling makes me giddy. Year five: Please, please just take this giant mess of numbers and make it pretty for the IRS.

2. Attorney(s). Year one: Finally got my DBA certificate from the city! Year five: Please threaten my landlord after my shop fills with water, and protect me from my own clients.

3. Business coach. Year one: Here's my business - I'm going to be rich! Year five: I have no idea what I'm talking about, and need help re-evaluating my place in the universe.

4. Business owner mentor(s). Year one: I'm never going to turn into you bunch of jaded, disorganized, burnouts! Year five: I am you. Where do I go from here?

5. Web design firm. Year one: Dreamweaver is cool! I look very professional on WordPress. Year five: I do not wish to read any more about CSS, SEO, or CMSs. Whatever amount of money you charge is worth it to make my web presence enchanting.

6. Business strategist. Year one: Business plans are for the birds. Year five: Wait, the bank wants to see my 12 month cash flow forecast and investors want to know my profit margin?

Optional, but extremely helpful: PR firm, social media expert, trade organizations, business banker, insurance agent(s), financial advisor.

I can say with total honesty now that I love having a "team" of people helping me with my business. Whenever I need a little guidance or questions answered, my team is there. PS - make sure you pay your team on time. And treat them nicely. That way they always pick up the phone when you call! 

Nina Interlandi Bell, co-owner of Tweedle Press, a small letterpress printing company in Chicago’s Rogers Park. Nina is Tweedle Press' fearless leader of design, letterpress printing, and sustainability research. Her laserlike focus and penchant for mission-hood make her prone to both fits of creative excitement and, occasionally, an overwhelming urge to do everything.

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