SEATTLE, WA – In this interview, Maureen Gilbert shares how she transitioned from building and selling businesses to mentoring women-led startups as a Venture Partner at MastersFund. With a career spanning over two decades, Maureen Gilbert is a seasoned expert in SME M&A, turnaround strategy, and risk management. As a Venture Partner at MastersFund, she draws from her diverse background – including roles in international banking, manufacturing systems consulting, and corporate strategy – to support and mentor women-led startups. Her experience includes consulting for Marcam Inc. and Price Waterhouse in Singapore, Hong Kong, Japan, and Chicago, as well as managing risk at ABN AMRO Bank in the Netherlands. Holding an MBA from INSEAD and a BA in Developmental Economics and Asian Studies from Georgetown University, Maureen brings a wealth of knowledge to the table.

Interview with Maureen Gilbert, Venture Partner at Mastersfund

Nhã: Thanks for joining me today! You’ve owned, operated and sold two successful businesses. And now, you are working as a Venture Partner at Mastersfund. Tell us how you got here.

Maureen: Absolutely, and thank you for having me. My journey has been a mix of serendipity and soul-searching. After selling my second company, I found myself in a reflective space, asking bigger questions about what I want from the next phase of my life. Around the same time, an opportunity opened at Mastersfund. Their mission – to champion women entrepreneurs – resonated with me, so I decided to jump in.

Nhã: It sounds like you were at a career crossroads. What influenced your decision most?

Maureen: I’d been wrestling with a question posed in Arthur Brooks’s book From Strength to Strength: Do you want to be special or happy? Do I want to double down on always being the top dog, or do I want to prioritize meaningful connections and greater impact? He talks about how our cognitive horsepower peaks in our late twenties or early thirties, and then we experience a slow decline. On the upside, there’s a different form of intelligence – wisdom, mentorship, teaching – that can flourish later in life. That really struck me.

Nhã: How did those insights shape your move into venture capital?

Maureen: Brooks’s idea got me thinking about my own path and how I’d spent years chasing the proverbial brass ring in my businesses. Don’t get me wrong. It was fulfilling to build and sell companies. But there was also a certain pressure: always be special. Always innovate, outperform, stay ahead of the next hotshot. Eventually, I realized I was tired of that treadmill. But I’m not exactly ready to retire and play golf all day, either! Focusing on mentorship and helping other founders succeed felt like the perfect pivot. Mastersfund invests in women-led startups, which means I can draw on my own experience and help female entrepreneurs navigate early pitfalls and scaling challenges.

Nhã: That’s a powerful way to pay it forward. You mentioned another influence: the concept of a “third quarter” of life. Can you tell us more about that?

Maureen: Sure. It’s a term Avivah Wittenberg-Cox uses to describe the period in life that’s no longer “young adulthood,” yet far from the retirement stage. Thanks to increased lifespans and better health, many of us have this bonus twenty-five years – an entire third quarter – during which we’re still vital and ambitious, but maybe not driven by the same cutthroat competitiveness we had in our twenties. We’re also not ready to just check out. So, we need new ways to channel our energy into something meaningful. For me, that means leveraging my background to help other women bring their visions to life.

Nhã: Your perspective is refreshing. Often, people think of midlife as a time of decline; you’re talking about it as an opportunity.

Maureen: Exactly. In my experience, that’s exactly the point where you ask yourself, Do I want to be special, or do I want to be happy? We joke about wanting both, but the reality is that constantly trying to “stand out” can become exhausting. It’s not that we lose ambition; it’s that we shift our focus. Instead of being center stage, I’m learning the joy of shining the spotlight on others. It’s a different brand of achievement. It’s less about personal glory, more about collective success. And let’s be honest, the women we’re investing in are phenomenal. Their energy and ideas are infectious!

Nhã: How does your experience as a founder shape your mentorship style?

Maureen: Having been in the trenches, I know how lonely and high-stakes it can feel. I also know the pitfalls, like burning out by trying to do everything yourself. Or chasing growth at the expense of culture and team cohesion. When I mentor or advise, I try to balance two perspectives: the practical side (like fundraising strategies, hiring smart, building scalable systems) and the personal side (like self-care, setting boundaries, and staying true to your mission). That’s where the lessons from my own journey, and from folks like Arthur Brooks, really shine. It’s about being more than just a “special” success story; it’s about thriving and being human in the process.

Nhã: We often see founders push themselves to the edge trying to prove something. Do you bring up those midlife “wake-up calls” when you talk to them?

Maureen: Absolutely. Even for younger entrepreneurs, it’s important to know that “winning” doesn’t have to come at the expense of personal joy or long-term relationships.  Prioritizing relationships, whether they’re with co-founders, employees, investors, or family, often leads to more sustainable success. The founders I work with might not be in the “third quarter” of life yet, but if they can cultivate that mindset early, they’ll be better prepared for the long haul.

Nhã: It sounds like you’re helping to build a legacy, not just a portfolio.

Maureen: Thank you. That’s definitely the goal. Mastersfund is about investing in the future and the motivation of the founders Gillian and Anne. For me personally, it’s about using my experiences – both the highs and the heartbreaks – to guide a new generation of women leaders. I’m not chasing external validation or “specialness” the way I used to. I’m channeling my drive into something broader, something that outlives my individual contributions. That might mean helping a founder avoid the mistakes I made, or encouraging someone who’s on the fence about starting her own venture. That’s a legacy that feels worth pouring my energy into.

Nhã: Any final thoughts for aspiring founders?

Maureen: Don’t let the pursuit of “special” overshadow your pursuit of purpose. Ambition is amazing, but it needs to be grounded in a bigger vision. Surround yourself with mentors and allies who genuinely want you to succeed, and don’t overlook your own well-being in the process. Above all, keep an open mind about what success can look like in different stages of your life. As you evolve, your definition of winning can, too.

Nhã: Thank you so much for sharing your story. It’s inspiring to see how you’ve turned big questions into big opportunities, both for yourself and for the founders you support.