Offbeat Bride launched on January 1st, 2007 and over the past 8+ years, the Offbeat Empire has grown from a thing I did first as a side hobby, then as a job for me, and eventually as a small business that supports a part-time staff of seven contractors. Looking back, I can see where there were a few terrifying milestones that forced my hand on growth. I’mma offer these up for y’all to consider… because growing pains can be horrific, but also kind of awesome. Forgive me if some of the details here are vague — when other people are involved, I’m going to opt toward keeping things general.
Unhappy advertiser refuses refund = I go S-Corp
An advertiser purchased an Offbeat Bride vendor listing, and then realized it wasn’t the product they had anticipated. I apologized for the misunderstanding, and offered an immediate full refund… which they refused to accept.
Wait, they refused the refund?! What else could I offer other than a refund? What could they do if they didn’t want a refund!? What if they like… wanted to sue me or something? OMG! Suddenly I realized that since my business was a Sole Proprietorship, my personal property (like my home) was at risk. This $300 miscommunication with an ad client could result in the liability of my $300k home. HOLY FUHHHHH. This was the terror I needed to get a lawyer to help me transition my Sole Proprietorship into an S-Corp business. Thankfully, I was able to work things out with the unhappy advertiser, but it was a great prompt to get my business/personal finances separated.
Copyright Trolling = I get Terms of Service and contractor paperwork clarified
A designer who I’d done a trade with in 2008 contacted me four years later saying they were unhappy with how their work was being used on my site. Although I immediately complied with their request to remove their work from my website, the designer’s lawyer then spent a year telling me (and companies I’d done work with) that they were about to file a lawsuit.
This was my introduction to the concept of copyright trolling, and it was the most terrifying thing ever. My small business friends were like “Aww, your first copyright troll! Welcome to the big leagues!” Apparently, this is just a thing that happens as your business gets successful, if you haven’t adequately protected yourself.
Ultimately I was at fault in this situation — not because I’d used the designer’s work incorrectly, but because I never made the designer sign a work-for-hire contract, nor did my sites have Terms of Service. These two oversights made my business an easy target for legal harassment. I spent a lot of money legally defending myself against the threats, and no lawsuits were ever filed… because there weren’t grounds for one. The whole idea with copyright trolling is to get cash settlements from business owners desperate to avoid lawsuits. I learned that every site needs a Terms of Service, and that no small business should EVER let someone do work without a contract. (Even if it feels like overkill, which it totally does.)
Flaky finances / I lock down my bookkeeping
I’d hired someone to help with my finances in 2010, but after a couple years it became clear that the person helping me didn’t have it handled. Quarterly taxes I thought were getting paid, had not been. Suddenly I went from thinking that my business was kicking ass to being like “Holy shit, I think I’m going to owe like $20k in taxes this year…”
In cleaning up the mess, it also became clear that my finances were big enough and complex enough that I needed to be balancing my books weekly, working with a bookkeeper monthly, and talking to a CPA quarterly. Now I log into Xero.com to reconcile my income and expenses almost daily. My bookkeeper and I review my financial reports and talk over revenue projections every month. I work with my CPA to obsessively file every city, state, and federal tax known to man, usually ahead of schedule.
This is the funny reality of running a small business: I may have started this whole thing as a writer, grown into an editor, and eventually graduated to publisher… but at this point I spend a lot of time on the exact same administrative crap that all small business folks have to manage. The financial stuff, the legal stuff, the administrative stuff. I have to make sure contractors invoice on time and track down checks that didn’t get delivered. I have to balance my books. I have to check in with my lawyer about trademark infringements. I consider it “doing things right” if I don’t have to deal with too many terrifying situations… but there’s no denying that those terrors help small businesses grow.