The Succeeding Small Story


Spotify | Apple | Youtube | Stitcher

As the CEO and Founder of Succeeding Small, Madeleine Costa has always had a podcast written into her business strategy. After working on a podcast for about 2 years, our team is thrilled to be able to present you with the Succeeding Small Podcast! With every podcast episode, you’ll learn new strategies to help start, scale, and be successful with your business. You’ll also have the opportunity to hear from other community members and small business owners who have sat exactly where you’re sitting. What better way to kick off the Succeeding Small Podcast than by learning all about the Succeeding Small story? Keep on reading to find out how Madeleine first started and how she’s used her entrepreneurial skills to create a six-figure business. 

How Did Madeleine Costa Get Her Start?

Madeleine comes from a long line of entrepreneurs and small business owners. She followed in her family’s footsteps and started her first small business at the age of 16. All by herself, Madeleine created an e-commerce website, attended craft fairs and trade shows, and began an online clothing boutique selling women’s clothing. Madeleine continued running this boutique up until she founded Succeeding Small in 2017. 

While attending school to get a degree in English, Madeleine was trying to figure out how she could combine her passions for writing and business to create a career. For one of her digital marketing classes, Madeleine was tasked with building a website, creating advertisements, and driving traffic to said website. So, Madeleine decided to create a blog full of advice for small businesses and called it “Succeeding Small”. At that very moment, the Succeeding Small story began. 

In the same class, a company came in one day and gave a guest lecture and told the class they were hiring interns. Now, what do you think happened next? That’s right, Madeleine accepted an internship with this agency where she learned the ins and outs of search engine optimization. Quickly, Madeleine realized that SEO was an amazing tool that could be used to help make real, impactful changes for small businesses, including those of her family.

Starting Succeeding Small

When Madeleine founded Succeeding Small, she knew she wanted to be able to integrate what she learned about SEO into business strategies for other companies. She had seen how much SEO helped her family’s various small businesses and she wanted to be able to provide the same high-quality digital marketing services to help the small businesses of her community.

Believe it or not, Succeeding Small was created overnight. Madeleine bought her trade name, built a one-page website, made a logo on PowerPoint, printed out business cards on card stock, and decided to attend a networking event the following day to see what would happen. There may not have been a formal business plan or thought-out strategy, but Madeleine had the one thing you need to start a small business: passion. 

Many small business owners approached Madeleine after the networking event and were curious about learning more about Succeeding Small’s services. In fact, Madeleine got five clients simply from attending that networking event that she decided to attend on a whim. This solidified Madeleine’s belief that there was a gap in the market and she could truly help small businesses succeed. 

How Has Succeeding Small Grown?

Since Madeleine first began Succeeding Small nearly five years ago as a solopreneur, she has grown her company to include a team of eight creatives and has built an internship program. It was extremely important to Madeleine to create an internship program because that’s where she first got her exposure to a marketing agency. 

Madeleine understands that Succeeding Small continues to grow and develop every day, and where the agency is today is completely different than where it was 6 months ago, 2 years ago, and 4 years ago. She also knows that it will continue to develop and change, which is what drove her to launch a podcast in the first place. Madeleine was on her own when she began Succeeding Small and had to find answers and learn lessons along the way, but she doesn’t want you to be alone while you’re navigating your small business journey. 

The image features two women sitting at a table with headphones on recording a podcast.

The Stages Of Succeeding Small

Even though every business is unique, they usually all go through the same business stages. For example, Succeeding Small’s business stages look like the following:

Stage 1: Starting Stage Of Business

  • Succeeding Small’s starting stage of business was nothing but fast tracked. Without an infrastructure in place, Madeleine hit the ground running and created her business overnight. While Madeleine has proven that you don’t need a business plan in place to start your small business, she also knows that they’re extremely helpful. When deciding if you need a structured business plan beforehand, you have to consider whether or not you thrive with structure. Some entrepreneurs, like Madeleine, need to dive in headfirst and start their own business, while others need to get all their ducks in a row first. 
  • Although this “diving in headfirst” method ended up working well for Madeleine, that’s not to say it didn’t come without its challenges. Because there was no foundation built before Succeeding Small was created, Madeleine had to work backward and create that necessary foundation while trying to grow her business. About a year and a half into business, Madeleine hired her first employee, a 1099 contractor. While imparting her wisdom about SEO, web design, ads, social media, and business philosophies, that was the first real opportunity that Madeleine had to create a consistent business strategy. 
  • Rather than having to create these systems, employee instruction guides, and processes midway, try to create your business systems early on.

Stage 2: Scaling Stage Of Business

  • As the founder of Succeeding Small, Madeleine was very adamant about not selling services to people that she couldn’t complete herself. So, she was the one sitting on the computer designing websites, creating copy, doing SEO, signing up for directory listings, and so on. If Succeeding Small offered a service, then you better believe that Madeleine could complete that task herself. 
  • At one point, Madeleine had to decide if she wanted to stay where she was: two employees and herself working at their maximum capacity. She had to decide if she was going to cap her clientele list and turn people away or if she wanted to scale Succeeding Small to be able to serve more small businesses. 
  • Madeleine decided that she wanted to scale Succeeding Small because that was the reason for starting her business in the first place; to help as many small businesses in the community as possible reach their goals. Although this came with a lot of unknowns, such as working with new people, setting up a maintainable infrastructure, and creating a teaching system so new employees could replicate the Succeeding Small standard, Madeleine knew that she had to do whatever it took to help her fellow small business owners. 
  • Since Madeleine expanded her family and had her baby girl in late 2021, she has realized more than ever how important it is to have a solid foundation and team that can take the reins when you, as the CEO and leader, need to step away. If Madeleine hadn’t built a strong management team and trained her creative team properly, then Succeeding Small would have had tremendous difficulties trying to stay afloat while Madeleine was on maternity leave. So, as you’re scaling your business and creating your own systems and processes, make sure to ask yourself, “ What do I need to put in place for me to be able to step away and take a vacation, be present with my family, or enjoy the holidays?” You want to make sure that what you’re creating can be sustained even without you taking care of your normal day-to-day activities. 

Stage 3: Sustainable Stage Of Business

  • One of the most important aspects of being a successful small business is finding a way to become sustainable. For example, in 2022, Madeleine is focusing on different streams of revenue for Succeeding Small. Multiple streams of income allow Succeeding Small to be continuously growing, which means that Madeleine and her team can continue the beautiful cycle of finding more clients, hiring more people, and serving the small business community. 
  • By exploring multiple streams of income such as a podcast, products, and digital marketing courses, Madeleine can explore different ways to honor Succeeding Small’s mission, which is to help small business owners grow their businesses and reach their professional goals. 
  • Another part of sustainability is creating a company culture where team members thrive and are eager to do their best work. For example, Madeleine is focusing on what it means to be a Succeeding Small team member. This includes thorough onboarding and offboarding systems, different benefit opportunities, and celebrating milestones.

The image features a mini marquee that says "PODCASTING" and next to it is a pair of AirPods.

Keep Coming Back And Learn How To Succeed Small!

If reading this made you feel motivated and made you stop and analyze your own small business, good! Make sure you follow along with Succeeding Small’s journey and tune in every Wednesday to our brand new podcast to hear more tips and tricks and learn about Madeleine’s path to success. By tuning in to the podcast, you’ll learn everything from how to scale your business, how to hire someone, what is an SOP, how to create an SOP, generating more profit, and advice from experts in the industry. Follow along the journey and keep learning from Madeleine and learn how your business can also #SucceedSmall!

Grow your Small Business With Succeeding Small

Succeeding Small is an expert in growing small businesses through our amazing digital marketing, SEO, branding, web design and social media services.  Learn about our services today!

Get More

Small Business Education

Sign up below to get up-to-date resources to help you grow your small business!


We help small businesses get the visibility they deserve as a digital marketing agency based in Colorado Springs, CO. We are proud to be a small business advocate, resource, and partner as you grow online!

Get More

Small Business Education

Sign up below to get up-to-date resources to help you grow your small business!

More Small Business Resources



You deserve a site that SELLS! Figure out why your site isn’t converting and implement the solutions TODAY!

the best podcast for


Weekly episodes to help you start, scale, and succeed in business!