5 Women to Study If You Have Expensive Ambitions

Because the lifestyle is cute, but the business model is better.

THE CREATIVE EXECUTIVE EDIT | BUSINESS, MONEY & POWER

Everybody wants the soft life. But who's studying the women who figured out how to fund it?

Let's talk about expensive ambitions. Not just designer bags, first-class flights, or a beautiful office with a view. We're talking about the kind of ambition that requires ownership, influence, financial intelligence, a strong team, and a business that can survive without you answering every email.

Because becoming that girl in business isn't just about looking successful. It's about understanding how success is built.

And while no businesswoman has a perfect playbook, there are lessons worth borrowing from women who have created recognizable brands, managed substantial capital, negotiated major partnerships, and built organizations with staying power.

Here are five women worth studying—and one legendary bonus—if you're serious about becoming a business tycoon.

01. Natalie Dawson: The Woman Who Knows That You Are Only as Good as Your Team

Her superpower: Leadership, people, and scaling businesses.

You can have the best business idea in the world, but if you don't know how to lead people, you'll eventually become the biggest bottleneck in your own company.

That's where Natalie Dawson comes in.

As co-founder and president of Cardone Ventures, Dawson has built her professional reputation around organizational growth, talent development, accountability, and operational discipline.

Her philosophy challenges one of the biggest misconceptions in entrepreneurship: that the hardest-working person should automatically be the most successful.

At a certain point, working harder isn't the answer. Developing a company that operates effectively is.

What to study: How she hires, establishes expectations, measures performance, and develops leadership capacity.

The million-dollar lesson: Stop building a business that needs you for everything. Start building a team capable of carrying your vision.

Your assignment: Identify three responsibilities you're currently handling that could eventually be delegated, automated, or systematized.

02. Kris Jenner: The Woman Who Turned a Last Name Into a Business Empire

Her superpower: Branding, publicity, and monetizing influence.

Say what you want about the Kardashians, but one thing you cannot deny is their ability to turn attention into commercial opportunity.

Kris Jenner understood something that many entrepreneurs still struggle with: visibility is only valuable when you know what to do with it.

From reality television to beauty, fashion, and lifestyle ventures, Jenner helped turn her family's public image into a powerful commercial platform.

And here's the fascinating part: she didn't need to be the person selling every product.

She understood positioning, personalities, audience relationships, negotiations, and how to maintain relevance across changing media landscapes.

What to study: Her approach to public relations, storytelling, audience development, partnerships, and brand extensions.

The million-dollar lesson: Don't just become visible. Build something valuable behind the visibility.

Your assignment: Look at your personal or business brand. What three products, services, partnerships, or intellectual properties could naturally grow from the audience you're building?

03. Emma Grede: The Woman Who Knows the Value of Being in the Room

Her superpower: Strategic partnerships, consumer insight, and equity.

Emma Grede is proof that you don't have to be the celebrity to build a successful celebrity-backed business.

As co-founder of Good American and a founding partner of SKIMS, she's established herself as an influential entrepreneur behind major consumer brands.

Before those partnerships, Grede developed experience connecting brands with entertainment and talent. She understood commercial opportunities and what audiences wanted.

That experience eventually positioned her to help build businesses alongside some of the most recognizable names in entertainment.

What makes her especially worth studying is her combination of relationship-building and commercial execution.

She doesn't simply understand how to get into rooms. She understands how to bring something valuable into them.

What to study: Partnership development, negotiating ownership, identifying underserved markets, and creating products with repeat demand.

The million-dollar lesson: Your relationships can open doors, but your expertise determines what you're able to negotiate once you're inside.

Your assignment: Identify five people or organizations that already serve your ideal audience. Think of a partnership you could pitch that would create measurable value for both parties.

04. Mellody Hobson: The Woman Who Understands That Wealth Is a Different Conversation

Her superpower: Investing, capital, and long-term financial strategy.

A woman can run a successful business, earn an impressive income, and still struggle to build lasting wealth.

That's why studying Mellody Hobson is essential.

As co-CEO of Ariel Investments, Hobson has spent her career in investment management, corporate governance, and expanding financial literacy.

Her career invites entrepreneurs to ask a different set of questions.

Not simply, "How much money did my business make this month?" but, "What am I doing with the money my business generates?"

How much is being reinvested? What assets am I acquiring? What is the value of my equity? How am I protecting the business against risk?

These are questions that separate earning money from managing and growing capital.

What to study: Investment fundamentals, capital allocation, corporate governance, and the difference between income and net worth.

The million-dollar lesson: Revenue can fund your lifestyle. Ownership and disciplined capital management can help build lasting wealth.

Your assignment: Review your company's finances. Determine how much revenue becomes actual profit, what financial reserves you need, and what opportunities exist to invest in future growth.

05. Janice Bryant Howroyd: The Woman Who Built an Empire Without Needing to Be Famous

Her superpower: Institutional growth, B2B services, and enterprise relationships.

Every aspiring business tycoon should study at least one woman whose business isn't built around personal fame.

Meet Janice Bryant Howroyd.

As founder of ActOne Group, Howroyd built a global workforce solutions company serving organizations through staffing and employment services.

Her story is a reminder that some of the largest opportunities in business exist in solving problems that companies consistently need addressed.

And unlike trend-driven consumer products, essential business services can become the foundation of long-term commercial relationships.

There's something especially powerful about that.

You don't necessarily need millions of followers, a reality show, or a viral product to build a substantial company.

You need a valuable solution, the ability to sell it, operational discipline, and customers willing to continue paying for it.

What to study: Business-to-business sales, enterprise client relationships, service delivery, organizational structure, and long-term contracts.

The million-dollar lesson: There's real money in becoming essential.

Your assignment: Ask yourself what recurring problem your business solves and how you could package that solution into a long-term relationship rather than a one-time sale.

THE BONUS ICON: Mary Kay Ash — The Woman Who Made Pink a Power Move

Her superpower: Brand identity, recognition, community, and sales culture.

Before pink Cadillacs became iconic symbols of achievement, a woman named Mary Kay Ash had a vision.

After experiencing professional limitations in the male-dominated business world, Ash founded Beauty by Mary Kay in 1963 with her life savings and support from her family.

She built a cosmetics company around more than products. It was an entire culture.

Think about it.

The pink packaging. The recognition ceremonies. The awards. The personal relationships. The independent beauty consultants. The unmistakable identity.

Mary Kay Ash understood something decades before the language of modern brand communities became fashionable: people don't simply buy products. They respond to experiences, relationships, recognition, and a sense of belonging.

Her company developed a highly recognizable direct-selling model, supported by training, personal relationships, and public celebration of achievement.

The business model has its own complexities, and an independent consultant's earnings are not equivalent to owning the parent company. But from a branding and organizational perspective, there are important lessons to study.

She built a business whose visual identity and core values remained recognizable long after her death in 2001.

What to study: Brand consistency, direct selling, customer relationships, recognition programs, sales-force development, and corporate culture.

The million-dollar lesson: A brand becomes powerful when people recognize it, remember how it makes them feel, and understand what it represents.

Your assignment: Identify three things your brand could become instantly recognizable for—whether that's a signature color, an experience, a recurring event, a customer ritual, or a distinct way of communicating.

Your Expensive Ambitions Need an Actual Business Plan

Here's the thing about studying successful women: the goal isn't to become a copy of them.

It's to recognize the skills, decisions, and business principles behind their success.

Learn leadership from Natalie Dawson. Study influence from Kris Jenner. Understand strategic partnerships through Emma Grede. Develop financial intelligence by studying Mellody Hobson. Learn institutional growth from Janice Bryant Howroyd. And study brand culture and recognition through Mary Kay Ash.

Then take the parts that fit your vision and apply them to your own business.

Because a beautiful lifestyle without a strong foundation is expensive to maintain.

But a business built on sound strategy, disciplined execution, valuable relationships, and lasting assets can create opportunities for years to come.

Don't just be inspired by powerful women. Study how they became powerful.

And more importantly, do the work required to become one in your own right.

Ready to Build Something Bigger?

At Green Book Group, we help entrepreneurs develop stronger brands, smarter business systems, executive leadership capabilities, and strategies for growth.

Whether you need strategic advisory, a more compelling brand presence, or creative visuals that position your business for bigger opportunities, we're here to help you build with intention.

Explore our services or book a strategy call to start building your next chapter.