I started a side hustle with a Craigslist ad and $250: Now it makes six figures

"My best advice is to embrace change, welcome new ideas, and always continue to experiment."

Jen Glantz is the founder of Bridesmaid for Hire.
Photo by Chris Ziegler

When I started my business Bridesmaid for Hire back in 2014, at first people thought it was a joke. I remember friends asking me what I was thinking, and strangers emailing me wondering if this was all a prank. It was decidedly not. 

By 2014, I had been a bridesmaid for my friends almost a dozen times, and a few things had become clear to me. Being a bridesmaid can feel like a job. Not everyone has a close group of friends to take on that role. And there wasn't any vendor in the wedding industry whose job it was to support the bride, and the bridal party, in an emotional and personal way. 

That was something I knew I could do. I started the business by posting an ad on Craigslist. After I got hundreds of emails from people wanting to hire me, I took $250, built a website, created a couple of initial services, and started booking clients. 

My business (which turns 7 in July) now offers multiple services and products and brings in six figures every year. I have been in hundreds of weddings. Over the years, I've made many mistakes and launched a number of experiments that didn't work quite the way I thought they would. But running this business has been the ultimate learning experience. 

Here is my best advice for how to grow your side hustle to make the biggest impact. 

Stay open to new audiences

One of the best ways that I've found to grow my business was to expand and offer services or products to a new audience. I started by just offering services to brides, but year after year have found ways to introduce new services and products to different audiences.

Two years in, I realized that I could work with maids of honor and provide them with a speechwriting package. I enjoyed public speaking and I knew there was a need for this service because I received 5 to 10 emails each month from people asking if they could hire me to help them with their speech. With that proof of concept, I was able to create another income stream for the business. 

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Three years in, after receiving thousands of requests from people who wanted to work for me, I launched another product for a new audience, a course to teach people how to start their own professional bridesmaid business. Over 250 people have taken it. 

I've tested out other audiences over the years, from mothers of the bride to bridesmaids, and have tried out products or services that didn't fully take off. But each of those experiments taught me something. Staying open to new audiences and using their feedback and questions to create new products has helped me significantly grow and scale my business every year. 

Regularly audit your assets 

Early on, I was on autopilot, making sure everything was staying afloat and functioning. Because of that, I wasn't innovating, catching errors, or finding ways to optimize my business experience.

Two years in, I decided that at the end of every month, I'd spend time doing an internal audit and take inventory on my business, everything from my finances to the back end of my website. Doing this has helped me save money, become more efficient, and figure out when to bring in paid consultants to provide feedback on things like my marketing materials and overall product positioning.

Just last month, I noticed that there was a major error on the website. I did a couple of quick fixes and was able to solve the issue in under two hours. Years ago, because I was so busy and wasn't looking closely at my own business assets, this is something I might have missed. This strategy has helped me feel more in command when issues do come up.

Carve out time to learn new skills

Two years into running Bridesmaid for Hire, I was laid off from my full-time job. It was scary, and challenging, but instead of seeing it as a setback, I realized that I had the opportunity to take my side hustle full time. But I struggled with one aspect of being my own boss at first.

When I was working at my tech start-up job, I was constantly learning new things from the people around me. The marketing team introduced me to new tools, and the sales team taught me how to master negotiation. I was even given the opportunity to take new courses and workshops paid for by the company. 

But when I went off on my own, I felt like I lost a lot of those things. I was working by myself and didn't feel like I was growing. So four years into running my business, I made two big promises to myself. The first was that every quarter, I'd take a new workshop or class that would help me develop a useful skill for the business. The second was to go to a social event like a networking meetup or a conference.

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Since then, I've taken a number of classes including an intro to coding class, which helped me fix up my website; a digital marketing course, which helped me plan new marketing campaigns; and a Facebook Ad course.

Attending social events has helped me meet and build relationships with other entrepreneurs. I feel less alone having this community of other business owners, and these connections have helped me figure out everything from which new tools to try out to what kind of help to bring on. 

Don't be afraid to ask for help 

When I first started Bridesmaid for Hire, I was eager to do everything myself, from designing the website to figuring out my own bookkeeping. This was mostly because I wanted to save money.

After finding myself working 60-hour weeks for those first three years, I was feeling burned out. I felt at my current pace and getting mired in day-to-day tasks, bigger goals that I wanted to achieve like writing a book and creating a better customer experience seemed out of reach. 

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A friend encouraged me to hire help, even if it was temporary, to tackle tasks that I didn't necessarily need to take care of myself. I started to use websites like Fiverr and Upwork, and searched Facebook groups to hire freelancers to help with things like social media content creation and creating graphics for landing pages. 

I decided to invest in professionals to help with important aspects of the business, like taxes, accounting, and legal, and to make sure I wasn't making mistakes that could potentially cost me more in the long run. Doing this has allowed me to have less busy work on my calendar so I can spend time innovating and growing my business.

Pay attention to analytics 

Over the years, whenever I wasn't sure what to do next, I found that there was power in understanding my analytics. For the past three years, I've taken analytics very seriously.  Whether it was deciding how to optimize my website, deciding on a good topic for a new blog post, or developing content for social media, diving into the metrics and numbers behind my business always served me well.

I use a few tools, including Google Analytics. The metrics I received here helped me understand more about the people who viewed my website, and how they were spending time on it.

I look at this data on a weekly basis because it's helped me make changes to the layout of my website to better the user experience, and it's helped me understand the types of blog content that will catch my audience's attention and what topics matter most to them. 

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I make sure to look at my social media analytics to help me plan content for the week ahead, too. I get these analytics directly from the Instagram or Facebook app, and I am able to see which pieces of content had the most engagement from the previous week. User comments help guide me on what subjects to explore further. 

Even though sorting through all the data can be time-consuming, it's worth it. Doing this regularly has helped my bottom line. Recently, it allowed me to see that there was a certain package on my website that was popular and when I moved that package to my homepage, it got even more people's attention and helped me increase sales by 25% that month.

Update your pricing annually 

I initially decided on my pricing by researching similar types of business (such as wedding planners or day-of coordinators) because my business was new in the industry. After settling on a price that was in line with those other vendors, I maintained that pricing for almost two years, even though after my first year in business I realized I was significantly undercharging.

I felt that if I changed my pricing at all, I'd be doing a disservice to my customers and might even push some of them away who initially discovered me when I had my original pricing. None of that was true.

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After the second year of Bridesmaid for Hire, I made a decision to update my pricing at least once a year. I'd factor in any increased costs of doing business (such as overhead, paying contractors and freelancers, travel, and more), extra value that I added into the product or service, like extra hour-long phone calls, and other variables. 

Over the past seven years, I have changed my pricing close to 10 times. Always make sure that you are charging what you are worth. 

Be ready to pivot 

When the pandemic shut down much of the world, it forced wedding entrepreneurs to pivot. Before 2020, I didn't offer any virtual services, but after Covid-19 led many couples to elope virtually or create part of their wedding experience over video chat so it would be accessible to guests, I had to adapt and offer services that met this rising demand.

After getting a series of emails from potential customers who shared their wedding planning situations with me, I decided to launch a limited offering virtual series during the pandemic.

I launched two new packages: a virtual bridesmaid package and a virtual wedding planning package using insight from those email requests, rising wedding trends I found reported in the news, and conversations I read about in wedding Facebook groups.

Over the past seven years, I have changed my pricing close to 10 times. Always make sure that you are charging what you are worth.

This made me realize how important it is to pay close attention to changes and trends. Reading industry blogs, setting Google alerts on keywords, and staying in touch with my audience via their online communities, social media, and at conferences, has helped me see what kind of new services or products to offer, even if those are only offered for a limited time, whether that is during a certain season or a truly unique situation like the pandemic.

When I first started this side hustle, I never imagined what it would look like after getting through that first year. Now, seven years later, I've learned the number one most constant thing about being an entrepreneur, year after year, is that you can never simply be comfortable or content with your business. 

My best advice is to embrace change, welcome new ideas, and always continue to experiment. Doing those things is why I'm still in business today. 

Jen Glantz is the founder and CEO of the business Bridesmaid for Hire, the voice of the podcast "You're Not Getting Any Younger,″ and the author of the Amazon-bestselling books "All My Friends Are Engaged and "Always a Bridesmaid for Hire."

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