The Unexpected Entrepreneur

Running a Small Business Means Owning a Big Hat Rack

In the last few hours I’ve helped two team members solve project problems, answered 3 urgent emails, had an impromptu phone meeting with a happy client, reviewed an invoice going out, shot a team member with a Nerf gun (deserved), and wrote a proposal for new business. In that time I’ve worn the badge of Culture Director, Accounts Receivable, HR, BizDev, Project Manager, and Account Manager. That’s a lot of hats.

When I get home later that night and my wife, Michele, asks me how my day was and what I got done, I really won’t remember, it’ll all be a blur. I’m not certain it’s an ideal way to run a work day, but it’s part of growing this thing.

My friend, Karim, told me once that running a business takes 40 to 60 hours a week, but if you’re growing a business there’s no upper limit.

So how do you find focus when you find yourself doing more than you thought possible?
Today, 15 years after I built my first community website using Photoshop and notepad, I find myself a startup entrepreneur with 7 full-time salaried team members. I like to think I’m weird, but the more small business owners I talk to, the more it seems that the majority of us ended up here by accident.

Startups weren’t cool when I started. I never intended to start a business. I just loved the web and its limitless potential. I loved building things. I loved helping people. I loved translating vision into digital substance. Perhaps these loves are how many of us stumble into being accidental business owners.

I asked a bunch of friends and clients how they got started and the responses are all very similar.

I was just really good at fixing stuff and making people happy

says the AC Repair owner.

I could do it better than the company I was working for so I started my own

says another client that now runs a service company that does work for almost every Fortune 500 company in the nation.

I hated my boss

says the freelance hairstylist.

I ask people if they’d do it again knowing what they know now. Most equivocate here. Generally I hear, “If I knew what I’d have to go through to get to a successful place in my business, probably not. But now that I’m here I wouldn’t go back.”

How many hats do we wear?

I already mentioned a few earlier. Let’s take a closer look. I’m the marketing guy, then the sales guy, then operations, then project management, then creative, writer, lawyer, then HR, webmaster, bookkeeping, accounting, damage controller, bill collector, jester, leader, and cat herder…yeah, that’s a typical day early in a bootstrap venture.

So let’s get focused. I’ve been told a good small business is a business that doesn’t need its founder to be successful, and I agree. So if we want to cure the too-many-damn-hats disease, we need people and processes. A good process will make average people into rockstars. And it’ll make rockstars into demi-gods.

But here I am 15 years later working with an amazing team of creatives, still trying to build better processes every day. How do we do this exactly? It’s a tricky question. Let’s start with you.
What are you amazing at? What do you love doing most? Where those things intersect is where you should be as that’s the place you’re likely to create the most value.

As your business gets better and you raise your prices, start hiring for the work you’re weakest at and enjoy the least.

For me, that was graphic design. While I loved doing it, I wasn’t great at it. And our designer is not just faster, but insanely better than I ever was.

But let’s not gloss over reality, hiring your first person is one of the hardest things to do in business. It gets easier for a while, then it gets harder again around 10 people. And I hear from there it gets harder again at around 100. Each “level up” presents entirely new challenges and bigger mountains to climb.

But where to begin? You can start by subcontracting or hiring part time and then hire as you have enough work for that position full time. If you hate bookkeeping, that should be your first hire. If you’re terrible at sales or marketing, get help there first. If you need help with something complicated be sure to weigh the costs of hiring vs outsourcing. Good places to do this in the beginning are things like payroll or digital marketing where hiring one person who can do the job right may be more expensive than using a specialized agency.

Every time you create a new position, you’re inventing a new process. Document everything as you go, or better yet, make the new hires write out all the instructions you give them as they go. Have them build their own training manual. They can use that to train the next hire in that position. And don’t forget to update those written processes as your business evolves.

So here I am, an unexpected entrepreneur, but with more focus and purpose than I’ve ever had.

And now, looking back, this is always what I was meant to do. And as long as you keep at it, it’s what you were meant to do too.

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