We were lucky to catch up with Ashley Dreager recently and have shared our conversation below.

Ashley, looking forward to hearing all of your stories today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?

I think about how my business would have been different all the time had I started prior to 2020. There is a significant learning curve in starting a digital business from all the tech, systems, and processes to network and audience building. Sometimes I think I could have grown faster and accomplished more had I entered the freelance space in 2018 or 2019, but that could have also come with other challenges. I’ve seen others who experienced significant, fast growth during 2020 ultimately to restructure their business model to accommodate the market adjustments that were made in 2021/2022.

Weighing all the pros and cons (even though we can’t truly know how things would have played out), I believe the time I started my business was the perfect time. The lessons I’ve learned in business, the foundations I’ve been able to establish, and the group of amazing individuals I’ve connected with likely wouldn’t have been the same. I am very happy with the growth I’ve had and the lessons I’ve learned because I know it’s ultimately setting me up for long term, sustainable success, which is the goal!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

My name is Ashley, I live in the Pacific Northwest with my husband and two daughters. I’m a Director of Marketing offering mentorship, consulting, and full marketing management to small businesses and startups. I am passionate about making an impact and seeing business owners achieve their version of success whether that’s through making an impact on their family, local communities, or even on a greater scale.

I have a background in business administration, sales, and leadership roles. I’ve always loved business, business management, and project management. It had been a dream of mine to get into a consulting field so finding the online business space in 2020 was a dream come true. I started offering Virtual Assistant services as I established my systems and processes, and quickly moved into marketing and strategy work. I enrolled in a certification to become a Director of Marketing in 2021 and received my certification in March 2022.

Since then I’ve offered freelance and fractional management services through my brand Drager Marketing. In May 2023, I co-founded Scale & Thrive Co. with my business partner Safa Harris to bring together the ultimate full-service package of marketing and operations services under one umbrella.

Marketing is at the heart of every business- it’s essential for growth, brand awareness, brand loyalty, and sales. Most of my clients come to me saying one of two things: either they’re completely lost or overwhelmed with marketing and have no idea where to start or they’ve got several marketing activities going but need someone to pull it all together to reach more people and make a larger impact. I help them by developing a strategy, essentially their roadmap, for taking them from point A to point B making their marketing activities streamlined and highly effective. I oversee the tactics (activities) for their marketing to ensure they’re done on time, on brand, and at the quality needed to see growth and progress. That may look like managing their marketing team (social media managers, VA, copywriters, ad managers, etc), collaborating with the business owner or their OBM/DOO, or having my team within Scale & Thrive Co. do it. all.

What sets me apart from others in the marketing/online space is the transparency and collaboration that comes with my services. My clients must have proper expectations for marketing as it can take months to see significant growth (relationships with our audience take time to establish!). I never oversell or overpromise the results my clients can expect in hopes of winning the contract. I become invested in my client’s business, it’s not a transactional relationship to me. The teamwork and collaboration between me, the client/business owner, and their team are the keys to success. Communication, honesty, collaboration, and integrity are non-negotiables with the work I’m doing!

What else should we know about how you took your side hustle and scaled it up into what it is today?

When I entered the freelance space in 2020, the intent was to make a few hundred dollars extra each month. My oldest was almost 1 and wanted to replace the side gigs I had previously done as I would need to stay home with her. Freelancing quickly opened my eyes to all the online businesses and truly expanded my idea of what opportunities were out there, and what options there were for employment.

Before this point, my idea of a career in freelancing was limited to copywriters and graphic designers. I, unfortunately, am neither. I quickly learned of fractional roles and all the other services that are in demand giving an alternative to the traditional W2, full time/part time roles. After this, I knew the possibilities were endless. While I’ve always loved working with teams, I never felt like I was able to make the impact I wanted within the corporate environment. I always felt like a number.

I became all in on making what started as a side gig, freelance business my full time business and career so that I can make the impact I want, without being limited to one singular company, or a singular job description. I can help small businesses and startups achieve their goals and ambitions while having a ripple effect into society and the world.

One of the key milestones to the growth in my business was through the Director of Marketing Certification program by Lindsay White. This allowed me to further develop the skills and knowledge I had going into the freelance space while connecting with a new network of individuals. This was truly the turning point in my income, service offerings, brand, and overall business model. I shifted away from hourly packages to project based retainers as well as being able to work with clients on a higher level in their business (truly stepping into the management and project management side).

Can you share a story from your journey that illustrates your resilience?

When I first started my business, I was sold the idea of naptime hustles. Unfortunately, my kiddo never napped or slept consistently enough for me to get those solid chunks of work time! I know this is a common struggle for other work-at-home moms- trying to find time to grow their business while being fully present with their kids.

When you’re in a growth stage of business, this is very challenging because there’s always something needing your attention. Sales, marketing, bookkeeping, customer service… There were a lot of mindset shifts that needed to happen and I struggled to find that balance for a long time. I was also pregnant with my second daughter which added another layer of exhaustion and demands.

I truly believed in the work I was doing and what I was capable of, so even though it would have been easier to close up shop, I didn’t want to. I loved my clients. I loved the impact I was making on their lives and business. So, I needed to find a new way. Learning how to pivot, stay flexible and fluid, and taking each day moment by moment was key. There were tactical changes made such as weekly planning, working after bedtime, working from my phone while holding her during nap time (to get that extended nap in), and working while at the gym.

Once I learned how to pivot in the moment to meet the needs of both my kids and my business, it became much more manageable. This was a major learning curve, and isn’t always easy. Especially with the constant message on social media about how (seemingly) easy it is to build a business while being at home with your kids.

There were many days I wanted to quit, and questioned if I was doing something wrong to make my experience so difficult. I believe the work I’m doing positively serves my clients and shares a positive image to my kids as they see their mom building a business while being home with them. It shows strength, determination, resilience, and discipline.

Contact Info:

• Website: ashleydreager.com
• Instagram: instagram.com/ashleydreager
• Facebook: https://www.facebook.com/dreagermarketing
• Linkedin: www.linkedin.com/in/ashleydreager

Image Credits
Agnes Szuberla, owner of Pacific Mist Photography https://www.pacificmistphotography.com/