Ambition and Identity: The Pressure of What Comes Next

Inviting Yourself Into the Room: Why AI Needs More Than Engineers

What happens when someone trained to protect consumers realizes the system itself is no longer built for the world we live in? On this episode of Between Builds, Tiffany Haynes sits down with Delicia Reynolds-Hand, Senior Director of Digital Marketplace at Consumer Reports and former Deputy Associate Director at the Consumer Financial Protection Bureau, to unpack the collision between AI, financial systems, and human trust. Delicia shares how her career evolved from community economic development law to helping shape consumer protection at one of the most influential regulatory agencies in modern finance. Together, Tiffany and Delicia explore why today’s regulatory frameworks are struggling to keep pace with AI-driven systems, what it means to build responsibly in an era of agentic technology, and why the people who understand human systems may be just as important as the people building the technical ones. The conversation also dives into imposter syndrome, technical fluency vs. technical expertise, and what it looks like to step into deeply technical spaces without a traditional engineering background. At its core, this episode is about redefining who gets to be called a builder and why the future of AI needs more people willing to invite themselves into the room.

Ambition and Identity: The Pressure of What Comes Next

In this episode of Between Builds, Tiffany Haynes sits down with Stephany (Yerger) Kirkpatrick —fintech operator, founder, and now, someone intentionally exploring what happens after the apex moments. After building, scaling, and exiting, Stephany finds herself in a different kind of chapter: one defined not by urgency, but by curiosity and the pressure of what comes next. Instead of rushing into the next build, she’s choosing to sit in the discomfort of not knowing by redefining ambition, identity, and success on her own terms. Together, Tiffany and Stephany explore: * The grief that comes with leaving behind a company, a role, and a version of yourself * Why the “encore” question can feel more like pressure than opportunity * How performance addiction shows up and what it means to recover from it * Rethinking ambition in mid-career, especially for women with financial optionality * Navigating money, risk, and decision-making in a dual-income household * Why choosing not to chase the next title isn’t “downshifting,” but intentional living and choosing what matters * The role of curiosity, experimentation, and AI in shaping what comes next Stephany also shares how this season has opened her up to new ways of thinking: from agentic commerce to health, aging, and community-driven ideas and why giving yourself permission to be a beginner again might be the most powerful move. This conversation is about resisting external timelines, honoring the messy middle, and learning how to build not just a career, but a life that you don’t have to apologize for.

Power and Purpose: Rebuilding Fintech Around the People It Serves

In this episode of Between Builds, Tiffany Haynes sits down with fintech and payments leader Amanda Estiverne-Colas to talk about what it means to reclaim your career and your purpose after burnout. After stepping away from a major corporate role, Amanda entered what she calls a season of professional recovery: a time to reflect, reconnect with family, and rethink what leadership looks like beyond titles. What followed was a new chapter spanning board service, advisory work, global speaking, and advocacy focused on financial literacy, inclusion, and consumer-centered innovation. Together, Tiffany and Amanda explore: * What “professional recovery” looks like after leaving a major role * The vulnerability and power of asking your network for help * Why more women in fintech are redefining ambition beyond corporate titles * The importance of empathy in designing financial products * How fintech leaders can rebuild the industry around the people it’s meant to serve Amanda also shares how initiatives like NAFLI and her work with Consumer Reports are pushing the industry toward a more human-centered approach to innovation - one where financial systems work not just efficiently, but fairly and transparently for the people who depend on them. This conversation is about leadership between chapters, protecting your energy, and building a career that aligns with both power and purpose.

Fintech with Heart: Translating Power Between Banks and Venture

In this episode of Between Builds, Tiffany sits down with Pam Kaur, a powerhouse in Fintech who operates at the high-stakes intersection of banking, venture capital, and platform leadership. Pam currently leads platform at Alloy Labs and was recently honored by NYC Fintech Women as one of the "Inspiring Fintech Females of 2025." But as Pam explains, her journey isn't just a collection of impressive titles—it’s a masterclass in the "unlearning" required to lead with conviction. From her upbringing as a child of immigrants where "women should be seen and not heard," to navigating male-dominated boardrooms where she was once told she’d be the "prettiest boss," Pam has had to fight to keep her voice from shrinking. Tiffany and Pam dive deep into: * Fintech with Heart: Why Pam traded her dream of being a fashion editor for computer science, and how her Substack is humanizing an industry often blinded by transactions. * The "Hostess" Mindset: How Pam uses her platform to open doors for others, acting as a translator between founders’ lived realities and VCs’ financial goals. * Strong Opinions, Loosely Held: Managing the tension of having a voice in rooms where you weren’t designed to be, and the power of being willing to be wrong. * The Power of the Ask: Why women often struggle to bridge the gap between personal friendship and professional networking, and how to stop "shrinking" out of fear of asking for too much. This conversation is for anyone sitting in their own "between" season—learning to trust their intuition, advocate for their worth, and step into the arena even when imposter syndrome is screaming the loudest.

When a Newsletter Becomes Infrastructure: Nik Milanovic on Building the Fintech Nervous System

Most media stories skip what happens when a “side project” becomes the backbone of an entire industry. This one lives there. Nik Milanović didn’t set out to build fintech’s connective tissue. This Week in Fintech started as a simple weekly write-up - habit, a curiosity, a way to make sense of what was happening in the market. But somewhere between the late-night drafts, the exploding inbox, and the growing community, it turned into infrastructure: 10 newsletters, multiple podcasts, a global team, and now a 1,000-person conference shaping the future of stablecoins. But when your project becomes a platform, what does it demand from you? And who do you have to become to sustain it? In this Between Builds episode, Tiffany and Nik step into the in-between years when your public persona grows faster than your comfort zone, when parasocial expectations collide with introversion, and when the “mess in the kitchen” forces you to build a team that can do things you no longer have time to touch. Nik shares the discipline of saying no when everything looks like an opportunity, and why pressure is still a privilege. Tiffany brings her operator lens, exploring the chaos, identity shifts, and internal recalibration that define every founder’s quiet evolution. This is a story about building something bigger than yourself, unlearning the instinct to do everything alone, and trusting the next chapter long before you can see where it leads.