Adriana Cowdin – Overcoming Adversity to Achieve Success

Adriana Cowdin brings 20+ years expertise in marketing to the table with a strong emphasis on digital marketing. She’s the Founder and CEO of Dekaf Digital, a social media marketing agency servicing mid-size companies.

This former corporate executive, turned published author and 4-time entrepreneur, came from the ranks of Corporate America where she was a Chief Digital Marketing Officer for a $5B home services company and Division Vice President of Social and Mobile Marketing for a $40B retailer.

Cowdin holds a Bachelor’s degree in Business Management and has completed leadership courses from Harvard Business School’s advanced program. She has been featured on ABC, WGN, CNNMoney, FoxBusiness, Forbes, Hoovers, Reuters, NYTimes, Inc. 500, and more.

A unique tidbit about Cowdin is she lives with 9 chronic diseases and has undergone nearly 30 procedures/surgeries since 2015. Her zest for life keeps her fighting every day to get up, exercise, take care of her family, and exude energy into her businesses.

What is Dekaf Digital all about?

Dekaf Digital is a social media marketing agency that delivers data-driven social media strategies, campaigns, and management to mid-size businesses in the U.S.

Tell us a little bit about your background and how you started your company?

I was a social media and mobile marketing executive at a $40B retailer overseeing 150 brands and 30 business units. From there I went to serve as the Chief Digital Marketing Officer of a household name home services company. After my first year in that role, I became very sick with chronic pancreatic disease. As I adjusted to this new disease, I had to balance my life with less work and more focus on my health. Starting Dekaf Digital 5 years ago gave me that opportunity for balance. I’m known to work anywhere as I’m often hospitalized or bedridden.

What would you say are the top 3 skills needed to be a successful entrepreneur, and why?

The top 3 skills needed to be a successful entrepreneur are: grit, commitment, and focus.

  • Grit because courage, resolve and strength of character will permeate the business, client relationships and partnerships. There are times when you’ll go months without a new client, or struggle to make payroll. You’ll face naysayers and have family and financial pressures constantly. These things happen and you have to have the grit to persevere.
  • Commitment because owning, and operating, a business is a non-stop, 24×7, 365-day a year lifestyle. You have to be committed to what you’re doing, and love it, or you’ll falter. If you’re halfway in, you might as well be halfway out.
  • Lastly, focus because the world has so many needs to solve. If you find that solution and it’s working, focus in on that niche. For example, when I started Dekaf Digital we were an full-service digital marketing agency for any client essentially. Over the years, we’ve focused in on strictly social media and on mid-market clients. That’s not to say we don’t have some start-up and Fortune 100 clients, but we do have a clear focus on where we stand in the market.

What are your plans for the future, how do you plan to grow this company?

When it comes to future planning, I’ve always got my health top of mind. I can only be successful in life if I’m healthy and with 9 chronic diseases that’s a daily challenge. To address this, I keep a smart and savvy group of medical experts around for my care and balance my diet and exercise.

For Dekaf Digital specifically, we have two paths we’re pursuing. The first is to partner with more agencies and be their go-to social media provider for their clients. This has been in the works for about a year and we’re seeing stellar results.

The second plan is to expand our services internationally; we’re currently in talks with a client that is looking for a global provider to cover EMEA.

How have the pandemic and Lockdown affected you or your new business?

I like to look at things through a positive lens. The pandemic gave us some fantastic opportunities to diversify our team. Previously we’d hired locally and the digital marketing talent here is scarce. Embracing the idea of remote work has elevated our team’s skills and happiness. We now have team members in IN, IL, FL, MI, and abroad.

For me personally, it has increased my client facing meetings. Typically I’d have to travel to a client meeting, which can be very hard on me physically. But with the pandemic, everything has moved to video meetings. I’m able to rest and catch up on work between meetings v. commuting.

How do you separate yourself from your competitors?

What separates Dekaf Digital from its competitors is our focus on data-driven social media marketing. Many social media agencies pull together a plan on what they “think” their audience will respond to and then, what I call, “post and ghost”. We first lean into audience intelligence data so we “know” the audience will respond to what we’re posting, pinning, tweeting, etc. Once we’ve posted, we actively engage with the audience and interact on other complimentary business pages and groups.

What were the top three mistakes you made starting your business, and what did you learn from them?

  • Only 3 mistakes huh? As an entrepreneur, the learning cycle is continuous. I mentioned it earlier in this interview but, in the beginning, we were providing full digital marketing services (SEO, PPC, Email, Site, Social, Content, etc). That left us too lean to really focus on any one thing and be an expert in it.
  • Lacking focus – In the beginning, we took on any client that could pay. Bad idea. You have to know what your client target market is and zone in on it to truly deliver the best results. Once we defined our market, we had much better success.
  • The 3rd mistake is doing everything myself. When you’re starting out you’re managing finances extra carefully and every new hire means new cost. I kept the team too lean for a while and noticed it was having a marked impact on my ability to both lead the company and service our clients. Once identified, I quickly staffed up – not overly staffed – to balance out the company and our client’s. needs.

Tell us a little bit about your marketing process, what has been the most successful form of marketing for you?

Our most effective, and successful, marketing approach has been to build agency partnerships. These partnerships not only drive new clients to the business but allow us to provide holistic strategies to new direct clients that need more than social media services.

What have been your biggest challenges and how did you overcome them?

My biggest challenge is energy, kind of an odd one, but it’s definitely mine. I live with 9 chronic diseases and that takes quite a toll on a body. I’ve had to learn how to balance leading a business while staying out of the hospital. I do this by leaving at least 15 mins. between meetings and only booking 3 meetings/day (to the best of my ability).

The next closest challenge has been finding quality team members. When we first started out, I was focused on hiring quality talent but didn’t look to my inner circle to find it because I have a family member who’s had 3 companies, always hires family and friends, and it never works out. Hiring “strangers” can be a mixed bag – much like hiring family and friends. When I leaned into my network, I found the BEST people and they’re so talented! Win-win-win

What was your first business idea and what did you do with it?

My first business idea was a product called HR In-A-Box. I wrote an entire set of policies, procedures, handbooks, etc., and put them all on one CD (yes, we used CDs back then) for small business owners. The idea was to provide a full suite of HR to companies with under 75 people as the business owner is typically also the HR person.

We had great success for about a year and then the market changed. We had run out of WOM clients and marketing, a lot of which was by mail back then, was not working. After a few years, I shut the business down.

What are you learning now? Why is that important?

What I’m learning now is how to manage life challenges (like my health) with my passion for the business. If it were up to me,  I’d work 14 hours a day every day of the week…simply because I love it. Unfortunately, my body simply cannot keep up and that seems to be a lesson I learn over and over again. #HardHeaded

If you started your business again, what things would you do differently?

If I started a new business, what I’d do differently is hire a business success coach and lean into networking with other entrepreneurs. It’s very hard to go it alone, with no one to bounce ideas off of, no one to collaborate or commiserate with, no one to hold you accountable, etc. It’s always nice to have someone to support the business and toss ideas around with.

What are the top 3 online tools and resources you’re currently using to grow your company?

  • One of my favorite tools is Canva. We use Canva to design presentations, infographics, social media creative and lead magnets. It’s so easy to use for anyone.
  • The next tool I use on a daily basis is HubSpot. HubSpot has been a fantastic CRM (Customer Relationship Management) system to hold all our customer contact info, meeting notes, emails, call logs and reminder tasks. I love it!
  • The 3rd tool we’re using to grow our company is Basecamp. This is a robust project management tool that allows the entire team to stay on top of tasks. It’s essential for those working with remote teams.

What’s a productivity tip you swear by?

If I have to narrow it down to just one productivity tip I’d say delegate/outsource tasks that don’t need your attention.

Can you recommend one book, one podcast, and one online course for entrepreneurs?

  • One online course I’d recommend is 100 Steps 2 Startup. This breaks down the entrepreneurial journey into 7 phases, step by step.
  • I’d recommend the podcast, The Shrimp Tank. They bring listeners interviews with some of the most successful business owners in the U.S. to learn the Do’s and Don’ts of starting, and running, a successful business.

If you only had $1000 dollars to start a new business, knowing everything you know now, how would you spend it?

This one is easy for me…and probably many entrepreneurs because we innately are always thinking of new ideas and businesses. It’s a blessing and curse J I’d start an online course marketed exclusively via social media ads targeted to those who need to learn about social media marketing.

What helps you stay driven and motivated to keep going in your business?

I stay driven to continue this journey professionally because social media is changing by the day and our clients are seeing phenomenal results for their businesses.

What is your favorite quote?

Be grateful for what you have and you’ll have more to be grateful for. – Me

What valuable advice would you give new entrepreneurs starting out?

When you’ve started several businesses, like I have, you have a lot of advice simply because you’ve learned over the years what works and what doesn’t.  I’d say first and foremost, have a solid business plan and prepare for financial challenges. Also, don’t be afraid to ask for help and put your faith in a trusted mentor/business coach.

Who should we interview next and why?

Lee Heisman, CEO of SavantCTS and Founder/Host of The Shrimp Tank Podcast.

What is your definition of success?

My definition of success is knowing my life is filled with abundance – both professionally and personally.

How do you personally overcome fear?

I personally overcome fear with 3 strategies:

  • Face it head on – I have a direct personality and prefer to face all things in life head-on with eyes wide open. When I’m fearful of something, I’d prefer to jump right in to it and conquer it.
  • Meditate – I’m a big believer of the mind and body connection and that inspires me to meditate daily, sometimes more than once. It centers me and helps keep any anxiety at bay.
  • Exercise –  I find the best way to clear my mind is to move my body through exercise. Increasing those endorphins and moving lets me clear out all other distractions and I’m more centered when I’m done.

How can readers get in touch with you?

I’d be happy to talk with any entrepreneurs about my journey, or theirs. I can be reached at, or through our website at

Adriana L Cowdin – How to Overcome FEAR & The Definition of SUCCESS