Masculine Traits, Motherhood & Money: What It Really Takes to Succeed as a Female Entrepreneur

Why Most People Oversimplify What It Means to Be a Woman in Business

When people ask me what it’s like to be a woman in real estate or entrepreneurship, they usually expect me to talk about sexism.

But that’s not really the story.

The truth is that the experience of being a female entrepreneur or investor is a complex mix of personality traits, social expectations, and life seasons — all of which shape how we show up and succeed in business.

In this week’s episode of The Real Escape Investing Podcast, I explore how traits we often label as “masculine” or “feminine” can shape our entrepreneurial paths, how expectations can quietly become advantages, and how motherhood redefines what success looks like.

It’s Not About Sexism — It’s About Traits

If you strip away the politics, success in entrepreneurship often comes down to a few psychological traits:

• Conscientiousness: being organized and consistent.

• Assertiveness: being confident and direct.

• Agreeableness: balancing collaboration with boundaries.

• Confidence: believing your ideas have value.

These traits aren’t gendered — but statistically, men and women express them differently.

Many women are naturally higher in agreeableness and conscientiousness, which makes us excellent communicators, collaborators, and managers.
Men, on average, score higher in assertiveness and disagreeableness, which makes them more comfortable with confrontation and risk.

The takeaway?
If you’re a woman, success might mean learning to flex traits that don’t always come naturally — like assertiveness — while leveraging the feminine strengths that do.

“Confidence, like muscle, can be trained. So can assertiveness. The key is knowing which muscles you need to build.”

Leveraging Feminine Strengths in a Masculine World

I’ve spent most of my career in male-dominated rooms — real estate, martial arts, investing.
Early on, I learned that trying to “act like one of the guys” wasn’t sustainable.

Instead, I leaned into what was natural:
Building strong relationships. Communicating clearly. Managing details others overlooked.

Feminine traits like empathy and organization can be huge assets in business — if you know how to use them strategically.
The challenge is knowing when to temper them.

For example, being overly agreeable can make it harder to say no or push for better terms.
That’s where “training” comes in — learning how to negotiate, how to take up space, and how to assert value without losing authenticity.

The Advantage of Low Expectations

Here’s a funny truth:
In many professional settings, women are still underestimated — and that can be a secret advantage.

When people don’t expect much, you get to surprise them.

As I shared on the podcast, I used to walk into sports competitions and boardrooms where the assumption was that I was inexperienced, soft-spoken, or there to take notes.
Then I’d overdeliver.

It’s oddly freeing when no one’s watching for you to fail — because you’re playing a game no one expects you to win.

So instead of resenting the “low bar,” use it as your stealth strategy.
Deliver excellence quietly — and let the results speak.

Motherhood, Mental Load, and the New Definition of “Balance”

When I was single, I could work till 9 p.m., travel constantly, and take big risks.
Now, as a mother and wife, I’m still ambitious — but my time and emotional energy are split differently.

Motherhood adds another layer to entrepreneurship:
It’s not just about hours; it’s about mental bandwidth.

Women often carry the emotional labor of family life — remembering the dentist appointments, sports schedules, permission slips, and grocery lists — even when they’re also running businesses.

That invisible workload affects how much creative energy and focus you can bring to work.

My male peers rarely face that same trade-off. But that doesn’t mean women can’t thrive — it just means we have to build systems and supports that recognize this reality instead of ignoring it.

Success Comes in Seasons

There was a time when I could grind endlessly.
Now, I see my career in seasons — times to build, times to nurture, and times to pause.

That’s not a setback; it’s an evolution.

If you’re in a high-output season, maximize it.
If you’re in a caregiving or slower phase, use that to refine, plan, or train others.

Every season brings different strengths. The key is to play the hand you’re dealt — fully, without apology.

What Female Entrepreneurs Should Remember

• Understand your traits. Know what comes naturally and what needs development.

• Feminine strengths are assets. Communication and empathy build trust — leverage them.

• Train confidence and boundaries. They’re not fixed; they’re skills.

• Redefine balance. Success looks different across life phases.

• Play your own game. Don’t measure your pace against anyone else’s.

“This isn’t a story about gender. It’s a story about self-awareness — and how to build a business that fits who you are, not who you think you should be.”

🎧 Listen to the Full Episode

Hear the full discussion on EP#213: Masculine Traits, Motherhood & Money on The Real Escape Investing Podcast. 

Listen on Apple Podcasts or Spotify