Madeline’s Journey of Courage and Failing Forward

Some women are born into business. Others build it brick by brick with grit, passion, and faith. For Madeline Costa, it’s both. The founder of Succeeding Small, Madeline is a second-generation entrepreneur who has taken her family’s foundation of hustle and turned it into a story of scale, strategy, and self-discovery.

In this chapter of Her Story, we go behind the business plans and marketing campaigns to uncover the woman behind it all—a woman who believes in failing forward and helping others discover their own version of success.

Scaling Something Bigger Than Herself

“I’m not the first entrepreneur in my family,” Madeline shared. “But I’m the first to scale it like this.”

With a mom who modeled resilience and drive, Madeline grew up knowing entrepreneurship wasn’t just a dream—it was a choice. She learned the importance of ownership, the beauty of flexibility, and the hard-earned power of building something of your own. But it wasn’t until she launched Succeeding Small that she saw how far she could take it.

What started as a simple curiosity—Do small businesses need marketing?—quickly turned into a calling. Within days of printing her first business cards on cardstock in her basement and attending a networking event, she had five clients ready to work with her.

“That moment confirmed everything,” she said. “I quit my job and never looked back.”

The Power of Failing Forward

Madeline’s approach to business isn’t rooted in perfection—it’s rooted in action.

“I live by the philosophy of failing forward,” she said. “You have to try. You have to experience. That’s how you learn.”

In the early years of Succeeding Small, the growth came fast. Almost too fast. Without the infrastructure to support the demand, Madeline had to figure it out as she went. She made mistakes. She cried through the hard seasons. She asked herself if it was still worth it. And then she kept going.

“Every time I hit a hard moment, I check in with myself. Is there still a spark here? Does this still bring me joy? If yes, I keep going. If not, I pivot. That whisper in your heart—you’re not done yet—that’s what I listen to.”

Rebuilding Through Entrepreneurship

Kristen Faith, the founder of Boss Babe Networking, connected with Madeline not just because of her professional achievements, but because of her spirit. “When you’re a survivor of trauma or domestic violence, entrepreneurship becomes more than a business—it becomes your lifeline. Your way of taking your power back,” Kristen Faith said.

And while Madeline’s story isn’t rooted in trauma, she understands the healing and reclamation that can come through building something of your own.

“You’re in the driver’s seat,” she says. “You get to decide what your life looks like.”

- Madeline

Faith, Flexibility, and Family

Madeline’s journey is one of deep trust. Trust in her vision. Trust in herself. Trust in the process. She spoke about the heartbreak and joy that comes with building something bigger than yourself—the nights where you question everything and the mornings when you rise anyway.

She also credits her mom, her earliest inspiration, for modeling courage and showing her how to lead through life’s toughest moments. “I admire her so much,” Madeline shared. “She always did what she had to do. That strength runs in me, too.”

And now, as a mother herself, Madeline sees her role not just as a CEO—but as a mirror to her daughter. A reminder that dreams are worth pursuing and that women are capable of anything.

Advice to the Aspiring Boss Babe

To the woman standing on the edge of her next leap, Madeline offers this:

“You’re not alone. Don’t try to be perfect. Don’t wait until everything makes sense. Just try. Find your people. Share your truth. Build your community. And know this—failing is just learning in disguise.”

Madeline Costa is more than a marketer. More than a founder. She is a woman on a mission—to help others succeed small, dream big, and live boldly.

This is her story. And we’re honored to share it.