In this episode, Priya Malani sits down with journalist and author Stephanie O'Connell to name something ambitious women feel constantly but rarely have language for: you can do everything right and still feel like you're paying for it. Stephanie's book, The Ambition Penalty, traces why the gender pay gap hasn't moved in two decades and why treating structural problems as personal failures is exactly how those systems stay intact. The conversation covers everything from workplace dynamics to the unpaid labor quietly subsidizing men's careers at home — and why opting out of ambition isn't the answer.

Takeaways:

• The gender pay gap has been locked in place for over 20 years, even as women have outpaced men in education for decades.
• Married men earn significantly more than single men, largely because women's unpaid labor subsidizes their availability at work.
• When women internalize frustration as a personal failure, it protects the systems producing unequal outcomes, which is not a side effect of those systems. It is the point.

  
  

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Guest Bio:

Stefanie O’Connell is an award-winning journalist covering money, power, and ambition whose work has been published in Slate, Bloomberg, Newsweek, USA Today, Glamour UK, Business Insider, and CNBC.com. She wrote, hosted, and co-produced Real Simple magazine’s Webby Award–winning podcast Money Confidential and publishes the Too Ambitious newsletter. O’Connell lives in New York City.

Guest Links:

Pre-order The Ambition Penalty

The Stuff Our Lawyers Want Us to Say:

Stash Wealth is a Registered Investment Advisor. Content presented is for informational and educational purposes only and is not intended to make an offer or solicitation for any specific securities product, service, or strategy. Consult with a qualified investment adviser (that's us) before implementing any strategy. Investing involves risk, including the loss of principal. Past performance does not guarantee future results. There…we said it.

In this episode, Priya sits down with Roni Hirschberg, founder and CEO of Generation Love, to trace 18 years of building a fashion brand from a waitressing job, a mom's foyer, and $100K that never got spent. Roni didn't go to fashion school, didn't have industry contacts, and didn't take outside funding. She and her business partner cold-called factories, learned every part of production by showing up in person, and worked full-time jobs for five years to fund the company without touching their savings cushion. This conversation is a real-time reframe on what entrepreneurship actually requires and why persistence, not planning, is the thing that keeps most businesses alive long enough to matter.

Takeaways:

• Working a day job while building a business isn't a hedge. For Roni, it was what let her stay ethical, pay her factories, and never compromise the thing she was building.
• You don't need a network to start. You need to be willing to show up, call strangers, and learn the parts of the business no one else wants to know.
• Being your own boss doesn't mean fewer people to answer to. It means more and the ones counting on you make quitting feel less like an option.
• Financial independence isn't about accumulation. It's about having enough to choose, where you live, how you work, what you walk away from.

Follow Priya Malani:

LinkedIn | Instagram | Stash Wealth | YouTube

Guest Bio:

Born and raised in New York City, Roni Hirshberg has always had an eye for fashion. In 2008, along with her partner Audrey Bressa, she co-founded Generation Love to empower women to feel confident and beautiful every day. Drawing from their shared appreciation of European style and modern NYC edge, the duo set out to create a brand where bold design meets everyday wearability.

Guest Links:

Website: generationloveclothing.com

IG: @rones_nyc, @generationlovelcothing

TT: @generationloveclothing

The Stuff Our Lawyers Want Us to Say:

Stash Wealth is a Registered Investment Advisor. Content presented is for informational and educational purposes only and is not intended to make an offer or solicitation for any specific securities product, service, or strategy. Consult with a qualified investment adviser (that's us) before implementing any strategy. Investing involves risk, including the loss of principal. Past performance does not guarantee future results. There…we said it.

Most financial businesses are built to grow fast and serve the clients who are already wealthy. In this episode, Priya Malani pulls back the curtain on six decisions she made building Stash Wealth that slowed growth, made the firm harder to scale, and prioritized what clients actually need over what's easiest to sell them. The episode isn't a pitch. It's an education in how incentive structures inside financial services quietly shape the advice you receive, and why that matters more than almost any single investment decision. Listeners walk away with a clear-eyed view of how to evaluate any advisor they work with.

Takeaways:

• The way your advisor gets paid shapes the advice you get, whether they're aware of it or not.
• The financial industry has decided people in their 30s aren't profitable enough to deserve real advice yet, and that calculation is working against you.
• Investing before you understand your strategy isn't being proactive, it's just gambling with a cleaner interface.
• A portfolio can't be evaluated as good or bad without knowing the person's goals, so performance comparisons are mostly noise.
• Financial freedom requires a trusted team across multiple disciplines, and who assembles that team for you matters.

  
  

Follow Priya Malani:

LinkedIn | Instagram | Stash Wealth | YouTube

The Stuff Our Lawyers Want Us to Say:

Stash Wealth is a Registered Investment Advisor. Content presented is for informational and educational purposes only and is not intended to make an offer or solicitation for any specific securities product, service, or strategy. Consult with a qualified investment adviser (that's us) before implementing any strategy. Investing involves risk, including the loss of principal. Past performance does not guarantee future results. There…we said it.