Side Hustle Adventures: How I Made My First $1,000 With Sip and Sew Workshops

My pal Crystal Hammond of Sophisticated Spender. Crystal is really amazing. She excels at pretty much anything she sets her sights on doing. In the past few years she has made extra cash on the side doing everything from teaching fitness classes to blogging. And she is an amazing seamstress. She has created some gorgeous dresses, skirts—whatever she envisions. I’m not really sure how she pulls it off.

Earlier this year Crystal raked in her first $1,000 from her side business, Sip and Sew Old Town in the Washington, D.C., area. She teaches workshops for groups to sew a purse, pillow, bow ties and what have you while sipping on libations.

Making money off of what you love to do really hits home with me because what I now do full-time started off as a side hustle. And I’m a firm believer that if you can make your first $100 doing something, you can make $500, then $1,000, and so forth. Crystal shares with Cheapsters her journey in side hustling and just exactly how she made her first thousand bucks:

Cheapsters: You are so talented when it comes to making your own skirts, dresses, pillows. How did you get into sewing?

Crystal Hammond: My mom used to sew and I used to hand sew clothes for my barbies.  My interest increased in high school. That’s when I learned to sew, but we didn’t have machines or anything like that.  We read about sewing in books and had to figure it out on our own if we wanted to learn.  

Well I went out and made myself a three-piece suit and got laughed right back outta school.  I quickly quit sewing after that debacle. Then around 5 or 6 years ago, I saw a really nice Nicole Miller dress in a magazine.  I fell in love with it, but couldn’t afford it. Then a friend told me that JoAnn’s was selling the very same Nicole Miller fabric.  So I bought the fabric and made my own version of that dress.  

Cheapsters: That’s awesome. So tell us a little bit about Sip and Sew Old Town? What is it exactly?

Crystal: We basically turn piles of fabric into something cool.  From newbies to experts, all sewing levels will enjoy this sewing class in beautiful Old Town Alexandria! We provide everything: sewing machines, supplies, materials and fabric.  We’ve had private birthday parties where a group of 10-year-olds made pillows. We’ve had couples parties where the women made a clutch and the men made a matching tie–or bowtie. We’ve made pencil skirts and zippered pouches.  All while sipping wine—and other crazy cool non-alcoholic beverages.  

I also have other classes in the pipeline: Bourbon and Blankets, Mommy and Me, Girls Night Out, Tutus for Races and a host of others.

Cheapsters: How did you get the idea for Sip and Sew Old Town?

Crystal: I attended a Sip and Sew class around four years ago.  We made a skirt that didn’t fit too well and I’ve never even worn it since then.  And I thought, if I ever had a class like that, we’d make items that the students would love.

Enter the $1K Side Hustle Income Challenge. I partnered with another blogger to challenge our readers—and ourselves—to make an extra $1,000 with a side hustle.  My initial idea was to have an online sewing webinar or something along those lines. So I created a sewing website.  It flopped big time.  Only two people signed up, and I was not gaining any followers or getting any interest.  However, I did an in-home-sewing lesson for one of the people who had signed up for my online sewing class.  We made pencil skirts, and that’s when I figured I can teach others that exact same thing.  I reached out to a local business and asked if I could teach my sewing class in her Paint and Sip studio on her least busy day.


Cheapsters: So how exactly did you make your first $1,000?

Crystal: I made my first $1,000 by being flexible.  I didn’t make a lot with the online webinar, and figured out what went wrong and quickly made changes. Even though 0 people signed up for my first Sip and Sew, I knew there was a demand for the service. That 0 meant that my message was not getting in front of the people who were looking for me.  So I started networking.  I introduced myself to people, got a mentor,  spent money on training, and on Facebook ads. I created a sewing meetup, posted more and more pictures on Instagram, and communicated more clearly with what I offered and what the students would learn.  I am also a part of some amazing Facebook groups.

I made $65 in November, $455 in December (thanks to an Eventbrite ad, Facebook ads, and an Instagram account created, $$1,059 in January (thanks to: Meetup Group created, Facebook ads, Instagram ads, networking with other local business owners).  Not sure what my totals were for February, but I’ve created a new Meetup group, and joined the gain more clients challenge and that’s helped tremendously!


Cheapsters: You’ve had other side hustles before. For instance, teaching Zumba, doing meal prep, and blogging. How did those other side hustles help Sip and Sew Old Town be successful?

Crystal: I still blog and teach the fitness side hustles and I’ve carried over all of the skills over to Sip and Sew Old Town.  

From blogging I’ve learned how to:
+Keep a consistent schedule
+Create websites
+Create a weekly newsletter
+Create cute pictures and ads
+Negotiate and barter

From teaching Zumba (and INSANITY) I’ve learned:
+Paying attention during class
+ a large group of people
+how to treat every individual like i want to be treated
+how to be myself in front of others (hello introvert!)

Cheapsters: What did you learn from your other side hustles that helped?


Learn to fail. I had a lot of failures on this journey.  Like I said earlier, I would never have made $1,000 in 1 month if I’d given up after the first class had 0 signups.  I wasn’t married to any single idea or single way of doing things.  I paid $95 for an Eventbrite ad that produced 0 signups.  I was really shy about asking the owner of the Paint And Sip studio if I could teach my sewing class there.  When I originally met her back in the spring of 2016, I didn’t ask.  It wasn’t until I volunteered to teach a Zumba class at her studio, I mustered up the courage to ask her if I could teach my sewing class there.  She was delighted and even more excited that I was.  Can you imagine if I had asked her earlier?

Work through bouts of discouragement. I also got discouraged because a very fancy sewing shop had opened doors two blocks away from where I’d be hosting my class.  I thought, ‘why would they pick my class over that fancy place?” I also doubted myself.  I don’t have any formal sewing training. I don’t have any special training or certificates or degrees. All that I’ve learned, I’ve learned from my mom and YouTube.

Practice makes perfect. When I taught the first class you’d have thought I was moving into the studio. I packed in so much stuff. I had so many things that I didn’t need.  Now I can pack an entire class into just three suitcases.  

Reflect. I also take about an hour after each class and write in my journal.  I write three things:  1) What went well; 2) what didn’t go well, and 3) how to improve for next time.


Cheapsters: How do you balance your day job with your side hustles?

Crystal: I keep a very tight schedule.  I work my eight hours on weekdays, then the real work begins. I have a notebook and calendar and I plan every single task.  

I also do the same things over and over.  For instance, on Mondays, I post a “Sewing Tip of the Day”, the day before a class I send a “Here’s what to expect at tomorrow’s class” email, and  three days after each class I send a “thank you” email to class attendees. Every day I have a task and I make sure that task is done.

It takes out all the guesswork on how to run my business. It’s just like teaching Zumba: I know that every Friday at 11:00, I’m at the gym teaching my class.  If you apply that to all of your tasks, it will go very smooth!


Cheapsters: What advice do you have for those who want to do their own side hustle?


Get started now. Like today!  Get a mentor, get a counselor, get involved in your side hustle industry.  

Get to know all you can about your side hustle. Learn from others!  Learn from me!  I am available for any and all questions and assistance. I actually help people start their own websites.  

Build your tribe. But I didn’t no do all of this on my own. I have so many advisors, mentors, coaches, friends, and so forth. I rely on my tribe to help me be great. Just don’t doubt yourself.  

Be authentic. People always hesitate because they think something has already been done but this is where you need to let your personality shine through.  People are looking for you. They are looking for someone who they can relate to and connect with. What if you’re a fitness instructor who wears glasses? You can teach a future fitness instructor who wears glasses all you can about how you make it work. A short person who loves basketball? A non-engineer who loves computers?  So be your authentic self when going after your dreams.  

Cheapsters: What’s next for Sip and Sew Old Town?

Crystal: We’re going on location. I’ve created Sip and Sew Woodbridge!  I am now traveling all over Virginia, and working on getting licensed in Maryland, D.C., Illinois, and a few other states.  Who knows, we may go international! I also want to focus on private parties, too.

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