Endless, exhausting waitressing shifts were common for me in my 20s as I bounced around, unclear of my passion, purpose, or what I wanted to do for work the rest of my life.
I distinctly remember the night I hit my breaking point. The restaurant where I worked was short staffed and packed. The kitchen and bar staff were stressed. Tables kept piling up. I started to have a cold-sweat, ears-ringing, mind-going-blank kind of panic, and I ended up hiding in the keg room.
It was 2013, and at that point, I had been waitressing on and off since 2001. Shortly after that shift, I heard a DJ on the radio saying Kelly Clarkson had been determined to make it as a singer so that she would never have to go back to waitressing again.
That struck a chord with me. I wrote that down on my serving notepad and taped it to the cash register so I would see it everyday. My goal was to start a business and be my own boss. But getting there was something of a winding road.
I finally quit waitressing for good in 2016, when I was eight months pregnant with my kid, and officially launched HerPaperRoute in 2017. I started the company to help other people start their own online businesses and share the marketing and growth-hacking strategies I learned from my side hustling experience.
My company has steadily grown. In 2020, it made seven figures. Here are some of the most valuable lessons I learned along the way about money, side hustles, and finding work that is meaningful to you.
In 2007, I decided to start my first side hustle, a clothing drop-shipping business. I'm a fan of the drop-shipping model because it completely eliminates inventory and shipping management from your pipeline, which was quite necessary for me at the time since I was living out of my office space with my dog.
With drop-shipping, for example, you put an image of a dress in your online shop and list it for sale at $100. When someone buys the dress from your site, you buy the dress from your wholesale supplier for $25. The supplier then ships the dress directly to your customer. Your profit: $75.
Around the same time, I started building websites, including one for myself: I offered social media services, and when I got orders, I would hire and connect my customers with freelancers, typically through platforms like Fiverr.
With these businesses I was able to usually generate around $1,000 to $1,500 per week to give myself some financial stability. I was able to pay off my student debt, pay my rent, build up my savings, and invest back in my businesses.
I ran these side hustles for about three years, and while they weren't my passion, what they gave me was so valuable: time and space to think about what I really wanted to do, including the ability to travel and gain new experiences.
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I loved building, monetizing, and selling niche websites because it let me combine all of the tech and marketing skills I studied in college with the sales skills I developed in my years as a side hustler. Over time, people started asking me to help them start their own online and blogging businesses, which was the foundation for HerPaperRoute.
From day one, I focused on building the HerPaperRoute community through a weekly email. Over time, I grew that email list from zero to 30,000 people, and today I have a dedicated email list for each element of my business.
If you're having trouble deciding what to write, or what to communicate to your audience, ask them what they are struggling with and what is important to them.
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Send out a quiz or questionnaire. Meet your customers where they are on social media, and pay attention to what they are saying. Understanding their pain points will inform the growth of your product or service, and consistent interaction through something like a regular newsletter will help establish you and your brand as a resource.
A great way to provide value through your email list is to include offers — such as coupons, a trial subscription, discounted samples of your product, or even a one-on-one consultation from you, depending on what your service is.
When you're starting a side hustle, my best advice is to set aside some of your start up budget to put towards tools that will help you grow.
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I'm also a fan of platforms like SmarterQueue for social media management, ConvertKit for email marketing, and HoneyBook for contracts and payments. Having the right tools at your disposal can automate your business functions and help you scale faster. For me, I found that once I had those systems in place, I was able to generate traffic and make sales on autopilot.
I use the time I saved to focus on creating content, such as new lessons for my courses, new offers for my audience, and resources for members of my group coaching program. I also am able to spend time on social media platforms like Clubhouse, sharing growth strategies with people in real-time, which in turn drives more people back to HerPaperRoute.
Growing up in a single-parent, low-income household, I was taught the value of work. But the messages I got about money were fraught. From an early age, I developed a sense that money was hard to come by, hard to deserve, and harder to keep — and that wealth often came from greed or luck.
When I started my own businesses, I realized that the things I had overheard as a child about money, bills, and worth had negatively affected my mindset. It was a challenge at first for me to accept that I had earned and was deserving of the money I was making. And while I had always been a scrupulous saver, in order to grow a business, I had to learn how to spend with intention.
I began reading personal finance blogs and attending business seminars, and they really helped. I started getting to know the businessmen and women who frequented the restaurant. I shared what I was working on with them, started to tag along with them to events and their speaking engagements, and began building a network I could rely on.
One of the biggest lessons I learned from my mentors was that investing wisely and for the long term, both in my business — and even in the stock market — wasn't something that was scary. I could be strategic. I had a tight budget and didn't spend a dollar on advertising or outsourcing that first year. But I did invest in a quality web host and email marketing platform, and took some relevant online courses.
As my business grew, I made room in my budget for advertising and to eventually hire a team. Ultimately my biggest expense was the time I invested. When you bootstrap something on your own and are doing everything yourself, no doubt you will spend more time than anything else.
Overall, my experience with HerPaperRoute was transformative. I began to have more positive associations with money and I realized that I could use my own earning power to help empower others.
Even on days when it felt like I was a naïve kid playing dress up, I still put my head down and did the work. It can be easy to stay stuck in an "employee mindset" when you first start your own business. It takes time and some work to begin viewing yourself as a founder and creator, and most importantly, the CEO.
A strategy that really helped at this stage was setting up joint ventures with other entrepreneurs in my space. Through co-workshops, co-sales, and affiliate partnerships I was able to leverage and connect with other people's audiences, and position myself as an authority early on, which in turn helped open more doors.
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Like in 2019, when I created a brokerage for small business owners to sell their companies and for investors to acquire them. Last year, during the pandemic, it was gratifying to help other founders sell their companies to the right buyers and put $400,000 in the pockets of small business owners.
Three years in, HerPaperRoute has grown into a lively community, podcast, blog, and a series of online business courses. In 2020, the company generated seven figures, and I'm excited to continue to grow.
I know how scary it can be to make a major change. But if change is calling out to you at this moment, then my best advice is prepare as well as you can and take that leap. I hung around waiting tables for far too long, simply because I didn't believe I had what it took to be a successful entrepreneur.
I realize now that what I thought was wasted time was actually fuel to help me stay focused on my goals. Even now on my most stressful day as a business owner, it isn't the same kind of stress I experienced when I was a server and a bartender. Because I'm passionate about my work, I ultimately feel energized rather than drained.
But I can still make a mean margarita upon special request. You never know what transferable skills will be useful in the long run.
Chelsea Clarke is a business strategist, investor, business broker, and the founder of entrepreneurship blog, podcast, and school HerPaperRoute. Chelsea paid off $30,000 debt in less than two years. In 2019, Chelsea launched the Blogs For Sale brokerage, where she helps investors and content creators buy and sell niche online businesses, blogs, and media properties.
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