Rewriting the Rules of Business: Madeline Reeves on Building Fearlessly and Scaling Authentically

The journey to building a million-dollar business is often wrapped in myth—overnight success, effortless scaling, and magical funding falling into the hands of the “lucky few.” But for those who’ve actually done it, the reality is a lot messier. It’s full of hard choices, financial risks, and a constant balancing act between ambition and personal identity.

Enter Madeline Reeves, Founder & CEO of Fearless Foundry, a powerhouse entrepreneur rewriting the rules of business—on her terms. In this episode of Badass Women in Business, Madeline gets real about the untold truths of scaling, the emotional toll of entrepreneurship, and why women must shift their mindset around money if they want to build sustainable, thriving businesses.

She’s not just talking theory—she’s lived it. From bootstrapping her way to a million-dollar business, to losing half a million dollars in projected revenue overnight, to completely rethinking how she structures her company, Madeline’s story is a masterclass in resilience, reinvention, and unapologetic ambition.

Success Isn’t About Luck—It’s About Financial Strategy

Madeline is quick to call out the real reason most women struggle to scale: pricing and financial strategy.

“The number one mistake women make when scaling service-based businesses is not charging enough,” she explains. “If your pricing isn’t aligned with what it takes to actually grow—hiring, reinvesting, paying yourself properly—you’ll never break through to the next level.”

She learned this lesson the hard way. In the early days of Fearless Foundry, she was working 70-90 hours a week, taking on too much, and constantly grinding to make ends meet. But her pricing structure was all wrong. She was stuck in a cycle of over-delivering and undercharging—until one day, she hit a breaking point.

A friend found her, face-down in a parking lot, completely burnt out. The advice was simple but life-changing: You can’t do this alone. Hire help. Raise your prices. Build smarter.

And that’s exactly what she did.

The Scarcity Mindset is Killing Women’s Businesses

Funding is another area where Madeline challenges conventional wisdom. Too many women, she says, buy into a scarcity mindset, believing that resources are limited and that they should feel “lucky” if someone chooses to invest in them.

Wrong.

“There’s no shortage of money,” Madeline insists. “But women have been conditioned to believe we should only be invested in based on past results. Meanwhile, men are constantly getting millions thrown at them based on potential. That needs to change.”

She doesn’t just talk the talk—she’s taken bold, unconventional approaches to funding, from leveraging CDFIs (Community Development Financial Institutions) to SBA loans to even learning how a friend funded her business by leveraging cattle. Yes, cows.

Madeline believes every woman needs to understand the full spectrum of funding options available, before they’re desperate for capital. She’s seen too many women fall into the trap of predatory lenders when they hit a cash flow crisis, simply because they didn’t know better options existed.

“We have to start talking about money more,” she says. “Not in whispers. Not in secrecy. Out loud, in rooms where decisions are being made.”

Redefining Leadership: Building a Business That Works for You

For Madeline, success isn’t just about revenue—it’s about ownership and autonomy. After years in tech, where she was always the only woman (and often the youngest) in the room, she knew she wanted to build something different.

That meant breaking away from the traditional corporate structure—one designed to extract as much value from employees as possible—and instead creating a collaborative, equity-driven model.

Her company now operates as a Creative Collective, where each team member owns their own LLC, sets their own rates, and builds their own entrepreneurial equity.

“I realized that I was making equity in my company, but my team wasn’t,” she says. “And that felt wrong. So I flipped the model. Now, every person who works with me is also building their own business. That’s how we create real change.”

The result? Happier employees. More financial freedom. Less burnout. Better work.

And proof that women don’t have to build businesses the way men have.

Fearless Isn’t About the Absence of Fear—It’s About Doing It Anyway

So what’s Madeline’s biggest lesson from her journey?

That being “fearless” isn’t about not feeling fear. It’s about pushing forward despite it.

Entrepreneurship is scary. Scaling is terrifying. Walking away from financial security to bet on yourself? That’s a whole other level of risk.

But Madeline is proof that when you own your ambition, charge what you’re worth, and demand the funding and opportunities you deserve—the results follow.

So to every woman out there second-guessing herself, underpricing her services, or waiting for permission to take the next step—stop waiting. The resources are there. The money is there. The opportunity is there. You just have to go after it.

And if you need a reminder that you belong in those rooms, making those big moves? Just listen to Madeline.

She’s built a multi-million dollar business on her own terms. And so can you.

Want More of Madeline?

Follow her journey, learn more about her work, and get connected with the Fearless Foundry community:

🌐 Website: Fearless Foundry
🔗 LinkedIn: Madeline Reeves | Fearless Foundry
📸 Instagram: @itsmaddyreeves | @fearlessfoundry
🐦 Twitter/X: @itsmaddyreeves | @fearlessfoundry

🎧 Listen to the full episode on Badass Women in Business Podcast and start making fearless, game-changing moves in your own business today.

Because the future isn’t waiting for you to feel ready. It’s waiting for you to take action. 🚀