NEXT Insurance is 100% dedicated to making it easy for small business owners and the self-employed to get the insurance they need to take their company to the next level. Autostraddle and NEXT Insurance are pleased to bring you the first installment of “Next Level,” an article series in which successful queer small business owners share how they tackle the challenges of business ownership to live their very best work lives. Today, our small business owners and self-employed superstars are sharing their inspirations and tips for living your best small business ownership life.
Delena Mobley and Kim Blessing had always loved fashion and had always wanted to start a Black-and-queer friendly business. But it wasn’t until the pandemic hit that they realized it was “now or never” to go for it and launch the gender and size-inclusive brand of their dreams, dom+bomb.
Brittany and Summer of Culture Flock started their quirky, eclectic store in 2013, during a transitional period for both of their careers. The same was true for me and my co-founder at Autostraddle: the recession that started in 2008 upended most of our career plans, so I figured 2009 was as good a time as any to see if my little dream had any legs.
For Jennifer Vinciguerra, CPA, it was ten years of notes on what she wished she could change about the small firm where she began her accounting career that eventually led her to decide it was time to go her own way.
Tracy and Mia, the co-founders of web design and development company Yikes, had been building websites for their non-profit and activist communities for a while before deciding in the mid-90s that they were ready to get paid for it. For Tracy, that was a realization of a desire she’d held since childhood to start her own business.
No matter where you are in the process of small business ownership or self-employment — still deciding if this is the right moment to turn your idea into a business or already getting your show on the road, it’ll undoubtedly be a lot of work, but the rewards can also be immense.
Here’s some of the best advice the queer small business owners we spoke to have picked up along the way:
Ask For Help
People with expertise, skills and experience are often willing to lend a few hours of their time to provide insight and support. Nothing I’ve read or been able to find online has ever matched the level of insight I’ve gleaned from others who’ve done similar work at different companies. You can often connect with other small business owners through industry conferences, local neighborhood associations and networking events, or through your local chamber of commerce.
“Small business owners want to see each other succeed, and queer and BIPOC business owners even moreso,” says Kim of dom+bomb. “We’re all in this together.”
Accept That You Can’t Do Everything Yourself
Nobody comes to the table with a full suite of knowledge about every aspect of running a business — and sometimes you do have the knowledge, but your skills or talent might be more efficiently spent elsewhere. Kim and Delena of dom+bomb are both marketers by trade, but they eventually outsourced their marketing to an external firm (queer-owned TinyTall Consulting), which is also queer-owned!) because other areas of the business required their focus.
Although I’d been trained in basic accounting and relevant software while working as the VP of Accounting for a literary agency in my twenties, I didn’t have any special bookkeeping skills or knowledge. Hiring Jennifer Vinciguerra to do Autostraddle’s accounting enabled me to focus more squarely on the creative work that resided in my specific zone of genius, and it was well worth the cost in the long term.
Follow Your Heart to Fill a Need
Many small businesses begin with a dream to put something into the world that wasn’t there before. “As queer kids from Springfield, MO, we wanted to create the kind of quirky, eclectic shop commonly found in big coastal cities like Portland, Seattle, and LA,” said Summer of Culture Flock, “ultimately creating a place that we wished we would’ve had growing up.”
Kim and Delena of dom+bomb always struggled to find cute clothes that fit, so they decided to make their own.
Sheena Lister, the CEO of short-hair styling products company Barb, had an idea that had been “percolating for many years” based on her own experience as a short-haired consumer who felt unrepresented in the industry.
Surround Yourself with Supportive People
“I could never have accomplished what I did without the resounding support of my wife (formerly my best friend), and an exceptional community of friends and family,” Jennifer says. “You need people around you who you can bounce ideas off of — there’s no shortage of wrong decisions to make and sometimes heeding the advice of an uninvolved third party is just what you need to figure things out.”
Often I’ll be grilling my girlfriend or friends for their take on my ideas, and they’ll often say something along the lines of “but I’m no expert!” That may be true, but they’re also my potential audience and customer base, so their input is far from irrelevant.
Don’t Be Afraid to Mess Up
Time spent trying out a new idea or working on an eventually-thwarted project is not time wasted — it’s a learning experience. Sometimes it takes 20 bad ideas to get to one good idea.
“We’ve learned the most valuable lessons from our mistakes in our 10 years of business,” says Summer of Culture Flock. “Even though they’re painful to your ego, those mistakes can lead you in the right direction if you’re open to it.”
The act of starting a business or working for yourself might seem risky enough in and of itself, but there’s no innovation without risk. “I wish I’d taken more risks in business earlier on,” says Tracy of Yikes. “Almost every risk we’ve taken has paid off.”
Often, women and people from marginalized communities are more risk-averse — they may lack a safety net or fear greater consequences arising from the risks they take. These aren’t empty fears: many successful entrepreneurs who are perceived as having a large appetite for risk are simply just rich enough to afford those risks. But there’s a middle ground between “playing it safe” and “buying twitter.”
Charge What You’re Worth
”Don’t put yourself on sale,” Tracy advises. “Charge what you’re worth. I’ve seen behind the curtain of businesses I thought were levels above us to discover everyone’s faking it. Don’t assume you’re inferior to others, and charge less for whatever your product is.”
This is especially true for service-based businesses. Be confident about what your time is worth and refuse to settle for less. I often try to envision what a cis white straight man would feel comfortable asking for, and then carry that sense of self-worth into the room with me.
“For those in a creative field,” Summer of Culture Flock suggests, “make things that you actually like! When you make things that are only for consumption by others, they don’t come across with the same heart and soul as projects that are close to your heart. So don’t be afraid to be authentic. It will be much more effective and appreciated!”
Get Inspiration Everywhere
Becky Bacsik-Booker and Alyssa Kaliszewski of Doll Parts Collective, a sustainability-focused vintage-shop-meets-curated-boutique in Seattle, cite an eclectic range of influences for their store, including Meow Wolf, Trixie Mattel, Iris Apfel, maximalist thrift/op shops of the 60s/70s, Nooworks and Robert Crumb.
Brittany from Culture Flock loves the Design Matters podcast. The dom+Bomb co-founders recommend “The E-Myth” by Michael E. Gerber for all small business owners and “Big Dress Energy” by Shakalia Forbes-Bell for fashion entrepreneurs specifically. Inspiration can come from so many different industries, not just the one you’re working with.
Get The Right Insurance For Your Small Business
All small business owners and the self-employed need small business insurance, although what type you need depends on the type of business you’re running. If you’ve got any employers or contractors, you’ll need workers comp. Brick-and-mortar stores require general liability and commercial property insurance to protect your inventory, your vendors and your customers, which covers issues like theft or disasters. Providing services or advice? You’ll need professional liability insurance for that!
Next Insurance makes it easy and affordable to figure out what insurance you need for your small business, with an easy-to-understand interface and convenient packages like the Business Owner’s Policy, which combines General Liability and Property Insurance. They specialize in providing insurance to small businesses and the self-employed.
Good luck out there, I’m confident you’ve got a great thing going!