I Left Freelancing and Built a Six-Figure E-Learning Business

For years, Emily Reagan freelanced to make money as a military spouse. The flexible freelance work allowed her to keep her income every time her family moved (usually every 1-3 years). But a few years ago, Emily transitioned away from freelancing to build an e-learning business. Today, her courses and online community help other women learn how to earn a great income as a marketing assistant.

In this interview, Emily shares the keys to growing her online education business. The interview is filled with practical takeaways that can be applied to the e-learning business model in any niche or industry.

How much revenue does the business generate?

$275,00 gross (and growing!)

Tell us about yourself and your business.

Even though I have degrees in journalism & electronic media and an MBA, finding meaningful, well-paying work as a military spouse was always a challenge. Every time we moved, I always struggled to bust into a new community and convince employers to hire me when I was just going to move away again in 1-3 years.

I made the best of it and had many jobs related to journalism, marketing, and public relations. In 2009, I fell into freelancing by accident. It turned into a new career that I never saw coming. I was able to offer my skills to brick-and-mortar and online business owners and bring my work with me every time I moved. No more starting over at the bottom!

My main services were all marketing-related in content marketing and marketing funnels. I booked out quickly because I stood out from all the other admin virtual assistants. I had a rare skill set with writing, graphic design, and being able to do technical work like website updates and integrations. 

I didn’t want to turn down clients, so I started a micro agency and trained 8 women to work with me. They came from different backgrounds but were able to dust off their skills and apply their previous work experience to these new marketing situations.

My client roster was so full, that I had to turn down clients all the time. Since I already had the training done and wanted to help more women find flexible work, I offered the training to the public and passed the job leads on to them. And that’s how my e-learning business was formed: from a place of wanting to help desperate business owners find reliable, marketing-savvy contractors and help my smart military spouse friends work again and not have to settle for crappy low-paying temporary jobs.

How does your business make money?

I never completely stepped out of the client work. Eventually, I shed my retainer clients but still took on marketing project work and consultations because I wanted to stay in the “how” of the business to be a better teacher for my community. So, my income here is not what it used to be as I focus on the e-learning products in my business.

Now I earn income from two main sources. My signature course, the Unicorn Digital Marketing Assistant School, runs as an evergreen self-paced program or as a live cohort in the fall. It helps women conquer the must-know marketing services to be competitive and helps them confidently think and take action in their clients’ businesses.

Our modules cover email marketing, funnels blogging & SEO, affiliate marketing, social media marketing, community management, and website updates. In this program I help students set up and launch their business too. Most VA courses just focus on the business setup (the easy part), and then VAs struggle with getting clients when they don’t know how to do the work or they’re trying to compete against lower rates of overseas workers.

Being a marketing generalist is the quickest way to get a foot in the door, without having to compete against the lower-paying admin VAs. From there my students can fork out in so many different directions within their services, business models, and roles. Many go on to become marketing managers, creative specialists, online business managers, etc. 

I continue to support them with advanced marketing training, client management conversations, and incoming job leads inside my community: the Digital Marketer’s Workgroup. This is a monthly membership to help freelance marketers get through the messy middle of freelancing – the part when we’re trying to specialize, raise rates, and get to the place where we’re only working with dream clients doing services in our zone of genius. I love this community because we rally to encourage, refer, and help each other. Otherwise, it’s a lonely world as a freelancer!

What was your inspiration for starting the business?

At first, it started, as I said above, to help business owners be able to hire someone like me since I was booked out. I would attend conferences and online events and get slammed with requests and have to turn them down. But I love connecting people. I knew if I could train Laura, a fellow military spouse in my town, in marketing and online business, she’d be able to help these clients and confidently scoop up the work during her kids’ school hours. I enjoyed helping both.

But the other side of this is helping an underrepresented community.  For years I undercharged and overdelivered to my clients because I didn’t know any better. I didn’t understand how marketing is value-based and brings in monetary results for my clients. I gave it away, helped clients make big money, (for one client, we hit $1 million on her launch), and was only charging $20 an hour! And that’s because I didn’t know anyone else like me doing similar work. I’m determined to help marketing service providers run sustainable and profitable businesses for the long term. 

How and when did you launch the business?

I started freelancing in 2007 while working as a Public Relations Director. My first project was writing press releases for local businesses. I didn’t have a master plan; I just attracted people who needed my help, and I said “yes.” Word got around.

For the next 10 years, I freelanced quietly behind the scenes of many businesses. I attracted a lot of creatives like designers and furniture painters with my content marketing services. I was totally happy behind the scenes, but in the summer of 2018, my husband at the time was deploying for a year and I knew I couldn’t keep up the agency model and run my house with four kids living nowhere close to family. I attended a conference with a client and, in those conversations, had the friendly push to become more visible and scale.

I filed my LLC and started being the face of my e-learning business. I launched my first course in January 2019 with an email list of 60. I had 20 students sign up for my beta. I opened my membership right after that group. I’ve been growing slowly and steadily ever since.

How is the business funded? 

My client work covered the start-up costs for the e-learning product tools and team. It was a tough two years doing both as I got the e-learning side growing and profitable.

How did you find your first few clients or customers?

My first students were from the military spouse world, and most I knew in person. I started in a small pond where I already had connections and then grew from there. Tactically I had started a free Facebook group and an even smaller email list that I had been nurturing.

What was your first year in business like?

The first year in business was a blur. It seems to be my mode of operation to have too much going on at once and somehow get through it. My husband was gone the first year, we sold our house, and PCSed (military term for moved). That summer he came back, I had a small surgery, there was family drama, and was juggling everything on my own – the business and my client work. But I kept one foot in front of the other and just took it at a pace I could handle. I knew that if I could just wow those first 20 students I could keep the momentum going.

It was a beautiful student success cycle. As I helped them develop skills and book their first clients, they shared their successes and others witnessed it and were eager to sign up with me. I launched again that summer and spread myself too thin. I realized that in the future I had to plan launches around my life so I would have the energy and capacity. I remember having to dial into a scheduled coaching call while my family was at Disney and not being happy with myself.

During that first year, I was not paying myself much, everything went back into the business to pay for tech stack and contractors. My client work was floating my digital products. I started to let some of my smaller retainer clients go to focus on building this course-model business, which was really scary. But I needed to free up time to learn live launching and prepare myself to be able to do webinars. By the end of the year I did my first webinar that brought in $8,000. If anything I proved the model, vetted my offer, and proved that I could do it. It was worth the stress.

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What strategies did you use to grow the business?

I started with the personal connections to get those first students and maximized their testimonials and wins to drive more buyers. On a marketing platform, I started blogging first. I knew the power of building up my presence online and ranking in Google. It was a great way for me to organize my thoughts and work through my messaging. I love it now because some of my articles get thousands of hits per month from very ready-to-buy prospects.

I’ve purposely been omnipresent showing up consistently on several platforms. I really haven’t gone all in with one marketing platform over another. But I play a mean repurposing game, taking something I’ve done to Instagram and finding ways to repurpose it across other channels and build it into my emails and funnels. It’s easy to get spread too thin here, and having a marketing assistant do this work is critical. I track everything to see what is converting, and right now, it’s still a mix with Google and Instagram sending the most new leads.

What was the biggest challenge you had to overcome?

The biggest challenge has been balancing a business with being a mom. There are so many times I wish I had a few days where I could just turn my brain solely on work and forget the world and my responsibilities. I would get done 10,000x more things in my business. I’ve had to walk that line of engaged, present mom with wanting to be a workaholic – not thinking about work and ideas when I’m “off the clock.” It’s hard because I love what I do, and I have the vision.

But time and resources are limited, so I have to focus on the most critical projects and cannot say yes to everything. I’m not sure how I’ve done it, working in the cracks of mom time for so long. I’ve had to be patient with myself and keep myself on track with my old reason for doing this business: for my kids. It’s balancing mom guilt with this better vision of the future in my brain. 

This is also why having help in our businesses is so important. It expands our capacity and allows us to work on the big-picture or money-making projects. Even though I’ve been on many teams, I’ve struggled to lead my team, hire the right people, and step up as a CEO who doesn’t do every little thing.

I’m in a messy growth stage of business where systems and processes need to be tightened up so everyone can operate smoothly and I don’t have to do it all. It’s a low-profit and tedious stage that will pay off with the ability to scale in the future. 

What have been the most significant keys to your business’ success?

It all goes into my “why story” and how intrinsically motivated I am to be successful. I really didn’t know if I could count on military retirement to support my family. I didn’t know if I was going to stay married. I knew I needed to bring home the bacon for myself in order to take care of my kids for the long term and the only person I can trust and control is myself. I can make that happen. So I did.

The need for financial independence and my desire to give my four children a good life keep me going when it’s tough and I face setbacks. It keeps me showing up consistently for my audience when I don’t feel like it. I wish I brought this type of discipline to the gym! 

I will say that when you have teammates working with you, waiting on you for deliverables to hit deadlines, there’s a fire to get it done so you’re not wasting time or money …and you treat your business like a real business.

Consistency. Teammates. Messaging. Those are my keys.

Tell us about your team.

I have about 6 part-time contractors who work with me monthly on a retainer model, just like how I started

1. Customer Service & Affiliate Manager
2. Marketing Assistant
3. Podcast & YouTube Editor
4. Community Manager
5. Membership Manager
6. Email Tech Specialist 

I also bring in specialists when needed: copywriters and ads manager.

How did you make the transition from side hustle to full-time?

The military made the choice for me to quit my full-time Communications Director role. I revved down for a few years to have babies but freelanced on the side.

In 2018 when my youngest was 1, I put her in daycare and went all in with my e-learning business and did everything I shared in this article. My journey was about being patient where I was in life with my capacity as a mother, military spouse, and default parent. I was itching to do things faster, but trying to be a present mom and not a workaholic.

I straddled balancing the client work and the digital product business for way too long. It was not easy. I went all in with the digital product business in the summer of 2022 when I left my last two big retainer clients and that’s when I had my $136,000 launch. The ‘all-in mentality’ was a huge part of that launch’s success. 

What was the turning point when you knew your business was successful?

It was actually a setback that got me to success. I had hired a lawyer to help me with a trademark, IP organization, and licensing for my business. Someone had copied my original course name (The Virtual Assistant Crash Course) and I realized I had a deeper problem: I didn’t stand out if I was that copy-able. 

I’d come up with the term Unicorn VA a few years early, but again, the problem was the same. People were copying that job title, which was also too vague.

I know we should be flattered by copycats, but it would continue unless I was bold and distinct. 

I spent a good 9 months percolating my messaging, the deep meaning of my business, and what our job title was. It was a deep existential conversation I had to have. I was so irritated by how this slowed me down but I wanted to get it right. Plus, my family was moving to a new state again, so I couldn’t do anything quickly with life happening.

This incubation time ended up being exactly what I needed. From this period, I came out strong with the specific job angle and trademarking “unicorn digital marketing assistant.”

Once I got clear on the industry I’m serving, what, and how, and went all in with my core rallying cry in my messaging, the rest fell into place.

I had a unique brand shoot with Shannon Claire that included an inflatable unicorn. I relaunched my course under a new name and made $75,000 in that launch, which put my name and business on the map. All kinds of name recognition and referrals happened once I was super clear on how I was different than everyone else.

What is the most important lesson you’ve learned growing the business?

I’ve learned that I can do hard things. Does that sound lame? Trusting myself, developing personally, and expanding have all been the best outcomes. There’s no prouder moment when we find ourselves rising to a challenge and taking it on. 

I did NOT want to be the face of my business. I was happy being behind the camera and one of my goals coming out of Journalism school was to be bossing everyone around from behind the curtain. I was the only person in my class who had no desire to be a TV reporter. However, once I had this vision of how I could help more women develop skills and find work, I knew I had to get over myself to be successful at my mission. I had to put myself out there to be comfortable.

I invested in myself to learn webinars, get better at speaking, get a branded photo shoot, and start showing up on social media. It was awkward. I felt so self-conscious but it paid off. I learned that the best thing I could do was show up consistently for my audience to build trust and show that I’m not a flash in the pan who’s going to fade away the second things get hard or stressful. It worked. 

What separates your business from your competitors?

Most Virtual Assistant coaches do not teach skills or how to do the client work. They pass out templates and help everyone start a business, which is the easy part and available on Google anyway. They’re also using the job title virtual assistant, which really doesn’t mean anything or carry certain responsibilities. Their students are ill-prepared to get inside a business and perform a duty. I even heard one of my competitors say she “wouldn’t teach skills with a ten-foot pole.” That’s because the tech and the strategist are always changing and their training isn’t dialed into a specific role and outcome.

I’m different in that I teach the actual marketing services to perform and operate as a Marketing Assistant, a real job title and position. This is someone who is trained tactically to implement a marketing plan and strategy. It’s the same work I’ve been doing for 10+ years. 

My training mixes the client work with online business strategies so my students can THINK once they’re inside a business. They can adapt to different clients and still bring value. Many of my peers are frustrated with their VAs because they do the bare minimum and don’t understand the next steps or purpose. With a solid business and marketing acumen, my Marketing Assistants can go above and beyond.

Some students will quickly level up into manager roles within a business. We can’t have leadership and initiative if we don’t understand the purpose and the vision. What’s interesting: I’ve seen students who have corporate marketing experience still need my training so they can understand the digital landscape. Of course, they progress really fast.

What advice do you have for other entrepreneurs?

Get help. No successful business owner does it alone. Yet I see so many in this online space think they can start and scale a business with very little human capital. They end up in the weeds or trying to function as their entire marketing and sales department and not actually building a business. The truth is that the right people in your business will be the fuel to growth. And that takes an investment of money.

This is why my marketing assistants have no trouble finding work. Everyone needs marketing help, and it’s not something a CEO or founder should focus on.

What is your favorite quote?

“Your business will grow to the level of healing that you have within your own life.” James Wedmore said this at Heather Sager’s PitchFest 2024. It reminds me that my personal growth and expansion are the best outcomes during this entire entrepreneurial journey.

What are your future plans for the business?

I’ve been live-launching for a few years now. My goal is to get my course on an evergreen model that sells and can help women start on their own timeline instead of waiting for me to open the course again in October.

I would love to take on the stage and motivate women to look out for themselves in their careers and ability to make money. I feel so passionate that every woman should have the ability to earn income with high-paying skills and provide for herself and her family. I am all about financial independence and giving women options.

A book. A movie (just kidding). I really don’t want to be famous but I love helping women get back to work after a baby break and seeing their confidence soar when they have a new professional identity outside the home.

If you had to start from scratch, where would you begin?

The million-dollar question! I would go all in with networking and relationship building to fast-track growing an audience. The start-up phase is so hard: You’re trying to do market research, build your offer, and vet your offer all while bringing in leads. If I could have done it differently, I would have done more audience-building first. I would reach out to affiliate and collaboration partners to tap into aligned communities. It’s such a simple and genuine way to connect with potential customers.

I’d also come out strong with my messaging. It took me a few years to really understand how my training and viewpoints are different from my competitors. Now, it seems so obvious, but four years ago, it didn’t! 

The lesson is the differentiated messages stand out— don’t be afraid to be bold! If I were starting over, I’d cut through the noise and get a messaging expert to help me with the positioning of my course promise and unique selling proposition. I’d be pushing the envelope with my thought leadership and content so it also stands out. I wasted too many years figuring this out, being afraid to speak up, insult someone, or get it wrong. Fear of judgment does not make my business money or help my students find me!

What are some of your favorite books, blogs, podcasts, or YouTube channels?

I go through seasons of consuming and then turning it all off to focus. Right now I’m in a nonconsumption season.

I’m currently reading Clockwork by Mike Michalowicz and 10x is Easier Than 2x by Dan Sullivan

I listen to Amy Porterfield’s and James Wedmore’s podcasts. I’m also a big fan of Ellen Yin’s case studies she shares on Cubicle to CEO.