7 Lessons Learned From a Maker on Her Wholesale Journey

Photo: Reba Jenson

Photo: Reba Jenson

2 years ago, we did our first Wholesale In a Box giveaway. Makers entered by commenting on our blog, and then we picked a winner from the bunch.

When we announced that Skyler of SugarSky had won the free 90 days of Wholesale In a Box, she was thrilled in the sweetest, most endearing way. Still one of our makers 2 years later, working to grow her wholesale business, we got the most wonderful message from Sky when we announced this year’s giveaway: “I SO VIVIDLY remember when I won the WIAB free trial via Dear Handmade Life! I never win anything and I was AMAZED. It’s proven to be such an incredible thing to win :)”

So we decided to hop on the phone to hear how her business has evolved since then. What she shared was really inspiring, very actionable, and sometimes surprising. Sky has managed to grow her business by leaps and bounds, and to a size that few makers know is possible. She’s stuck to her mission and values, finding thoughtful ways to bring in production help as she grows, but never compromising on what is most important to her.

Listen in as we talk to Skyler and she gets honest about wholesale, growth, hiring, what’s worked, what hasn’t, and what she wants newer makers to know...



“My motivation to do this daily is that our whole operation is based in the US.  We get to support the people in our community, as those are the people who design and sew our products.  That is very motivating for me because it means we are helping people here in our country continue to feel empowered and appreciated.  

I could manufacture our products at a 16th of the cost if we outsourced some to offshore but, for me, keeping jobs here in the US and helping people on our soil to be employed is top of my list and always will be with SugarSky.

Of course, you have to keep your margins working,  but I know that so long as SugarSky exists, jobs for people here in America will exist.”



“Before launching the business, I started brainstorming and thought; What talents or skills do I have in my wheelhouse that I can turn into a business?  I tossed some ideas back and forth and thought, well, I know how to sew and I am always wearing headbands.

The idea was born after a couple glasses of wine in our tiny little apartment in Atlanta.  My husband was like, ‘OK why not?.’ I also knew how to build a website so that wasn't a barrier to entry for me so decided to give it a go from there.”  



“My original goal was to sell 10 headbands.  I thought: If I sell 10 headbands this is a success.  I had left my full-time job in Corporate America so my aim was to sell 10 the first month so that could go towards helping pay our bills that month.  The next month, we planned to reassess.

There were lots of trips to fabric stores to find a good material and sewed prototype after prototype, finding the right material that was comfortable and a good fit.  After that, I just pressed the launch button, with only 5 patterns. The business was me sewing everything and trying to work out the kinks as I went along.

Not everything has to be great when you start and focusing on progress over perfection is always my aim.  You just need to pull the trigger and work from there.”

Photos: Reba Jenson



“My business is very different now than when it first launched.  In the beginning, I was sewing everything. Still being in my corporate job at first meant things were taxing.  You can almost get burnt out because, after a day at work you don't want to spend so much time on your business even though you love it, but you have to.

It then went from me sewing everything to having a team of highly skilled seamstresses. That transition was a huge learning curve and I am so thankful we did that.  We received our first wholesale order of 6000 which was huge for us at the time so this forced us to reassess. I knew I couldn’t sew everything myself forever.

We hired the seamstresses as contract workers -- paid by the piece..  This means you cannot designate hours or manage them as employees but they produce the volume of product required to meet your demand and they are paid on how many pieces they produce. This worked really well for us because they could do the work while their kids were napping or on weekends… and we didn’t have to worry about filling the time every single month of a full-time employee”  



“Inevitably, starting a business is risky. So it's important to invest in people or processes that do things better than you. As an entrepreneur, the biggest mistake you can make is trying to do everything on your own.  

I believe if you are investing in the right things at the right price for your business, you will see a return.  This was the case when we signed up with Wholesale in A Box. I remember getting WIAB’s 5-part email course after signing up and I thought. ‘Oh my gosh, this is all such good information.’  Then with your help, I started drafting my emails to potential customers. I went for it with the help you provided. Ever since then we have seen some great successes with wholesale.

One way to test your approach to investing in something for your business and give it three months; if you don’t start seeing an uptick in revenue after this time, then you can cut it off.”



“We’ve had our fair share of failures. In one instance, my fabric supplier completely ran out of fabric. I realized I had put all my eggs in one basket with only one supplier and there was a real risk I would have to shut down the whole business.  The supplier then provided an alternative solution but their replacement simply wouldn't work for our designs. A year into the business, that was a scary moment. Thankfully we sourced an alternative supplier, who we still use today, and things are working great.

I talked to my Dad, who is an entrepreneur, and he said ‘You have to keep moving.  You don’t have to get back to where you were, just get to a different place that works for your business.’  I then came up with a totally different way to sew the headbands. It uses less fabric and it’s less labor intensive. So the outcome had such a positive impact on the business in the end.

With challenges, you have to take the energy of the problem and let it throw you into the next phase.”

Photos: Gretchen Powers



“The biggest thing that I have learned through this business is to strike a balance between patience and tenacity. There are some things you have to slow play and others that you have to push really hard. Anything in excess or lack isn’t good.

If you’re constantly pushing, you're going to get burnt out, but if you’re always sitting back, you’re not going to get anywhere.

Owning your own business, you need to find a balance between these while not letting your business define you.”

A huge thanks to Skyler for sharing her journey and insights! As always, she shows a remarkable mix of humility, confidence, and generosity, and we’re so glad SugarSky is thriving. You can follow SugarSky at sugarskyshop.com and at @SugarSky.

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