We were lucky to catch up with Madeleine Costa recently and have shared our conversation below.
Madeleine, appreciate you joining us today. One of the most important things small businesses can do, in our view, is to serve underserved communities that are ignored by giant corporations who often are just creating mass-market, one-size-fits-all solutions. Talk to us about how you serve an underserved community.
“Every year around the holidays, I don’t know if I can keep my business open another year.”
My client confided in me one morning, talking about how his business leads dry up every year around Thanksgiving and Christmas. He sipped his coffee, recounting how he didn’t know if he had enough funds to pay his bills come the beginning of the year or even be able to buy Christmas gifts for his kids. He thought many times about giving up his dream of entrepreneurship and getting a job.
This is not an unfamiliar story to the entrepreneur community. Small business owners have poured their heart and soul into their businesses, sacrificing financial security for the passion they have for running their own companies. This risk that entrepreneurs take to succeed in this world comes with the highest stakes.
In order to succeed in small business, we rely on sales and revenue to pay our bills, keep our business afloat, and put food on the tables for our families. We need funds so that we can buy gifts for our children to wake up to on Christmas morning. We need incoming customers to make payroll so that their employees can do the same.
Small businesses everywhere struggle with marketing their business and attracting new customers.
They struggle to compete in their marketplace against the corporate conglomerates that have billion-dollar marketing budgets.
They struggle to get the visibility they need to get in front of their target audience.
My own family of entrepreneurs lived and breathed that same struggle.
That’s why I set out to change the way that small businesses market. I began my digital marketing agency, Succeeding Small, with one mission: make marketing accessible to the small business community.
If anyone deserves visibility, the chance to be seen and heard in their local community, it’s a small business. With SEO, web design, social media marketing, and paid advertising, I am able to get small businesses the leads, customers, and revenue that they need to accomplish their goals and support their families.
Most marketing agencies target medium, large, and corporate businesses. Their services come at a premium, and their clients can afford it.
But every business starts out small, and sometimes they need someone who will take a chance on them.
I wanted to be that resource, that partner, that guide, for small business success.
In that same breath, my client told me something that affirmed my calling and something I’ll never forget. He said, “Because of the work you’ve done, this is the first year I haven’t had those fears.” He said that he was booked out for months, for the first time ever around the holidays.
Because I was able to market his business and get him the visibility that he deserved, he could keep pursuing his dream of small business ownership. He is no longer just “surviving” as a small business owner; he is THRIVING.


Madeleine, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I have always had an affinity for marketing. I started my first business at 16–an online women’s clothing boutique. I learned how to build my own website, market on social media, and promote my business at craft fairs and trade shows every weekend.
Growing up in a family of small business owners, I was no stranger to marketing either. We were always solving problems about “What business could we start today?” or “How do we sell this to more people?”
I was able to professionalize this interest of mine during an internship opportunity during college. It was there that I learned search engine optimization: the process of getting websites to show up online on Google. Paired with my degree in Rhetoric & Writing (the study of arguments and persuasion), and my minor in Marketing, I now had the tools that I needed to legitimately market and grow small businesses.
I saw firsthand how SEO can change lives, and I completely fell in love with it.
I started my agency at 21 years old, right before I graduated college. Now, I get to live and breathe my passion of serving my small business community by providing integrity-filled marketing to help get them the visibility they deserve.
Today, I have a team of 6 and an internship program of my own where I can give back to students in the same way that changed my life forever. I’m also the host of The Succeeding Small Podcast, where I produce free, action-oriented content to help small businesses start, scale, and succeed in business.
I have served hundreds of small business owners with marketing services and education, and am so honored to be a part of someone’s success.
How’d you build such a strong reputation within your market?
When I began my company, I learned one thing very quickly: there are many agencies that practice unethical digital marketing.
Whether it was shady, bait-and-switch sales tactics to trick businesses into paying thousands of dollars without real results or blackmailing small business owners by owning their websites/domains, there was no shortage of horror stories.
I knew that I wanted to be the light in this industry. I have vowed to practice integrity-filled digital marketing at my agency, and I lead with transparency in all that I do. I believe this has aided me in building a solid reputation in my community because small businesses can come to me for honest and ethical advice.
We include education lessons for all of our clients, clearly outlining what we will be doing for them and why it’s important. We have transparent, always accessible reporting dashboards that they can log into at any time to see the work being done and the progress being made.
Not only that, but I often share my marketing know-how publically on The Succeeding Small Podcast as well. Every week I dive into specific tips and action items that come directly from our own systems and processes.
I believe that a more educated, empowered community is what we need to elevate the digital marketing industry as a whole. I lead by example in this way, and hopefully my reputation exemplifies that.

Any advice for growing your clientele? What’s been most effective for you?
When I first started Succeeding Small, I grew my business through networking. I would browse Facebook Events and load up my calendar with as many opportunities as I could find. I met hundreds of business owners this way, which grew my company FAST.
However, that growth definitely came at a cost: my time and energy.
As the years went on, all the countless hours, events, and meetings started to burn me out.
By 2021, I was a ghost of myself. I was working all the time, I had no energy left for myself or my family, I had easily 30 meetings a week, and was drowning in obligation.
Yes, it was great for business, and I was meeting potential clients all the time, but it was not sustainable for myself.
So I started to cut back, trading my physical time to invest in my own digital marketing.
I could either reach 20 people in a room or I could reach 200 people online. It was (and is) still such a hard choice to make each day because I love networking–I love people, I love relationships. But I knew that I needed to scale my business, and that couldn’t be dependent on my time, energy, or mental health.
It’s so funny that choosing to invest in marketing is such a hard choice for business owners. It’s hard to spend time and money on an effort that doesn’t always produce immediate results.
But now, 50% of my leads are complete strangers who have found me online by typing in things like “small business marketing agency,” “SEO Colorado Springs,” and “web design company.”
I literally get my ideal, qualified clients IN MY INBOX every day. And I didn’t have to do anything to go and get them.
I didn’t have to spend 3 months nurturing a relationship. I didn’t have to spend $$$ on memberships and lunch meetings. I didn’t have to exhaust myself by booking up my calendar just to make 1 sale.
Instead, I started treating my business like a client. I invested in my own SEO. I built out my website. I created content. I marketed on social media.
Yes, it still took me a TON of time, but what I could accomplish in a day was tripping my results than when I was doing in-person selling.
And relationships are STILL front and center in my business. The method of introduction has just changed.
Digital marketing saved me from burnout. Digital marketing is the reason I can scale my business, maximize my time, and create the kind of life I want for myself and my family.
I am my own testimony to why I believe so much in what I do. 
Contact Info:
- Website: https://succeedingsmall.co/
- Instagram: https://www.instagram.com/succeedingsmall/
- Facebook: https://www.facebook.com/SucceedingSmall/
- Linkedin: https://www.linkedin.com/in/madeleine-costa/
- Twitter: https://twitter.com/succeedingsmall?lang=en
- Youtube: https://www.youtube.com/channel/UCRr2HOH5-q6aNX5uO5JLGAQ
- Yelp: https://www.yelp.com/biz/succeeding-small-colorado-springs
- Other: The Succeeding Small Podcast: https://succeedingsmall.co/the-succeeding-small-podcast/
Image Credits
HUGE thank you to Taryn Kimberly Photography for the Succeeding Small branding photos!

