Humans of Fintech

What does it take to scale a fintech company to millions of members without losing the personal touch that made it special in the first place?

In this episode of Humans of Fintech, Nicole Casperson sits down with Janelle Sallenave, Chief Operating Officer at Chime, to explore the leadership decisions, customer experiences and personal lessons behind one of fintech's most recognizable companies.

Janelle shares how Sunday afternoon financial lessons with her mother shaped her relationship with money, why she became fascinated with creating exceptional customer experiences, and what she learned during her career at Charles Schwab, Uber Eats and Chime.

They discuss Chime's evolution into a public, profitable company, the importance of staying close to members as a business scales, and why even the smallest customer frustrations deserve executive attention.

The conversation also turns to AI and the future of leadership. As technology takes on more tasks, Janelle explains why human judgment, taste and vulnerability are becoming increasingly valuable, and why leaders don't need to have all the answers.

It's a conversation about building companies that last, protecting what makes them special and remembering the real people behind every financial transaction.

This episode of Humans of Fintech is sponsored by Chime.

• How Janelle's mother taught her financial independence and the importance of understanding money
• The career path that took her from management consulting and Charles Schwab to Uber Eats and Chime
• Why scaling a fintech company requires protecting its culture and customer experience
• How Chime keeps its members at the center of decisions, from executive listening sessions to individual support escalations
• Why small details can have an outsized impact on consumer trust
• What established financial institutions and younger fintech companies can learn from each other
• How AI is shifting the value of work from completing tasks to exercising judgment and taste
• Why vulnerability, adaptability and reverse mentoring are essential leadership skills
• What Janelle hopes Chime's impact on financial health will look like in the years ahead

00:00 Highlights from the conversation

01:00 Meet Janelle Sallenave, COO of Chime

02:34 From consulting to building exceptional customer experiences

04:34 The financial lessons Janelle learned from her mother

07:54 Discovering your leadership superpower

10:32 How Chime has evolved as it scales

13:40 Keeping customer obsession and company culture alive

16:01 The responsibility of serving millions of members

18:18 Why leaders need to sweat the small stuff

20:53 How trust is built when something goes wrong

22:21 Fintech innovation versus legacy banking infrastructure

25:59 Why AI makes human judgment and taste more valuable

29:21 Vulnerability, change and the future of leadership

32:04 The impact Janelle hopes to leave behind

Humans of Fintech, hosted by Nicole Casperson, Founder and CEO of Fintech Is Femme, goes beyond the headlines to explore the people, personal stories and leadership lessons shaping the future of money.

Subscribe to Humans of Fintech on YouTube, Spotify and Apple Podcasts for more conversations with the people building the financial industry's future.

Sponsor disclosure: This episode is sponsored by Chime.

This episode of Humans of Fintech is sponsored by Alix, an AI-powered estate-settlement platform helping families navigate the process of transferring inherited wealth.

Learn more about Alix: https://www.meetalix.com/

The Great Wealth Transfer is expected to move roughly $100 trillion from older generations to the next. But there's a problem hiding underneath that enormous number.

How does the money actually get from one generation to another?

When someone dies, somebody still has to find the bank accounts, track down assets, navigate lawyers and financial advisors, deal with property and paperwork, and make sure the inheritance reaches the people entitled to it.

And much of that work falls on women.

Few people understand this better than Alexandra Mysoor, Co-Founder and CEO of Alix, an AI-powered estate-settlement platform that has raised more than $30 million from investors including Acrew Capital, Charles Schwab, and Edward Jones Ventures.

Alexandra didn't set out to build a company around inheritance. It started when her best friend's mother passed away and Alexandra volunteered to help with a to-do list on the refrigerator.

That simple promise turned into 900 hours of work over 18 months.

What she discovered was a massive financial process that remained fragmented, expensive, and overwhelmingly manual. Families were expected to coordinate the work themselves, even as trillions of dollars prepared to change hands.

In this episode of Humans of Fintech, Nicole Casperson sits down with Alexandra to explore how a deeply personal experience became a fintech company, why estate settlement is an overlooked piece of financial infrastructure, and how AI could make generational wealth more accessible to everyday families.

They unpack why women disproportionately carry the burden of settling estates, the surprising connection between inheritance and financial inequality, and what Alexandra learned from making 189 pitches to raise her seed round.

Alexandra also shares how an unexpected elevator encounter helped transform her fundraising journey, why she believes technology should solve fundamentally human problems, and what it means to build a company at a stage of life when many women are wondering whether it's too late to pursue their biggest ambitions.

At the heart of this conversation is a question that goes far beyond estate settlement:

What good is generational wealth if families can't actually access it?

This is a conversation about money, grief, women's economic power, entrepreneurship, and the invisible work standing between families and the wealth they've inherited.

Subscribe to Humans of Fintech for more conversations with the people building the future of financial services.

In this conversation, we dive into:

• 00:00 Why generational wealth should be accessible to everyone
• 00:38 Meet Alexandra Mysoor, Co-Founder & CEO of Alix
• 01:32 The ambition Alexandra had before becoming a founder
• 02:48 Why you don't need to see every step to pursue a big dream
• 04:39 Motherhood, ambition, and finding your next chapter
• 05:35 How Sallie Krawcheck's words shaped Alexandra's thinking
• 06:30 The family loss that changed everything
• 07:11 How a refrigerator to-do list became 900 hours of work
• 08:14 Why settling an estate is so complicated
• 09:37 The broken economics of estate settlement
• 10:35 What Mozart taught Alexandra about an ancient financial problem
• 11:48 The moment Alexandra decided to become a founder
• 12:10 Black Wall Street and the meaning of generational wealth
• 13:05 Why inheritance shouldn't require family-office resources
• 14:00 The missing infrastructure behind the $100 trillion wealth transfer
• 16:53 Building a fintech company as an industry outsider
• 17:50 Why estate settlement is also a women's economic issue
• 19:50 What 189 investor pitches taught Alexandra
• 21:15 The elevator encounter that changed her fundraising journey
• 22:45 Why human relationships still matter in the AI era
• 24:02 Using AI to solve deeply human problems
• 24:47 What's next for Alix
• 25:55 Why inheritance creates an opportunity for financial advisors
• 26:48 Final thoughts: Money, power, and women

YouTube: https://www.youtube.com/@humansoffintech

Apple Podcasts: https://podcasts.apple.com/us/podcast/humans-of-fintech/id1600731457

Spotify: https://open.spotify.com/show/3zA6yUb3D7I5ZRbehlsdX7

For more fintech news, founder stories, and FTW updates:

https://www.fintechisfemme.co/

In the age of AI, access to powerful technology is becoming universal. Standing out is not.

When every company can build faster, automate more, and deploy similar tools, the real competitive advantage becomes much more human: a clear story, a trusted face, and a reason for people to believe in what you’re building.

Few people understand the intersection of storytelling and growth better than Angelique Strauss, Founder and CEO of ScaleX.

Angelique entered fintech after immigrating to the United States and experiencing firsthand how difficult the financial system can be to navigate. Building credit, purchasing a first home, planning for retirement, and moving money across borders were unnecessarily complicated—even for many people who had lived in the country their entire lives.

That experience shaped her belief that fintech is not simply about better technology. It is about making the financial system more accessible and helping people understand how financial products can improve their everyday lives.

In this episode of Humans of Fintech, Nicole Casperson sits down with Angelique in front of San Francisco’s iconic Painted Ladies to explore why storytelling has become essential infrastructure for fintech growth.

They unpack why founders must become the faces of their brands, how trust changes go-to-market strategy in the age of AI, and why major business relationships are increasingly moving from virtual channels back into physical rooms.

Nicole and Angelique also go behind the scenes of building FTW San Francisco, following the success of New York FinTech Week. They discuss what traditional conferences get wrong, why smaller and more curated gatherings can produce better business outcomes, and how the strongest fintech ecosystems are built through collaboration—not competition.

Angelique also shares the fintech company whose go-to-market strategy has caught her attention, why access to capital remains painfully difficult for small-business owners, and how stablecoins could make global remittances faster and more affordable.

This is a conversation about storytelling, trust, access, community, and what it takes to build a fintech brand people will remember in a world flooded with AI-generated noise.

Subscribe to Humans of Fintech for more conversations with the people building the future of financial services.

YouTube Chapters / Timestamps

In this conversation, we dive into:

• 00:00 Why financial access remains unnecessarily complicated
• 00:45 Meet Angelique Strauss, Founder and CEO of ScaleX
• 01:41 Why fintech is being overlooked in the AI conversation
• 02:36 Angelique’s immigrant journey into fintech
• 03:22 Has fintech actually become more accessible?
• 04:20 Why financial data may be fintech’s greatest moat
• 04:53 In the AI era, features are no longer enough
• 05:30 How founders can build a memorable brand
• 06:08 Why fintech companies need a human face
• 06:27 Trust as the defining advantage in AI
• 06:53 Why major deals are moving back into physical rooms
• 07:18 AI is making people crave more human experiences
• 08:37 Why modern growth requires digital and physical touchpoints
• 09:04 Where fintech’s AI future comes to life
• 10:28 Why Angelique said yes to building FTW
• 11:26 What traditional fintech conferences are missing
• 12:00 Why smaller rooms can generate better business outcomes
• 12:27 Building a room for fintech’s “closers”
• 13:00 Why companies grow faster through community
• 13:57 Creating content that goes beyond product promotion
• 14:54 Personalizing the conference experience
• 15:33 What makes San Francisco’s fintech ecosystem different
• 16:01 Why fintech and big tech need each other
• 16:42 What Angelique wants attendees to take away from FTW
• 17:15 The fintech company everyone should be watching
• 18:04 Why access to capital still fails small businesses
• 19:01 The future of remittances and global money movement
• 19:56 Building a financial system that works across borders
• 20:28 Subscribe to Humans of Fintech

👇🏼 SUBSCRIBE + FOLLOW HUMANS OF FINTECH

YouTube: https://www.youtube.com/@humansoffintech

Apple Podcasts: https://podcasts.apple.com/us/podcast/humans-of-fintech/id1600731457

Spotify: https://open.spotify.com/show/3zA6yUb3D7I5ZRbehlsdX7

For more fintech news, founder stories, and FTW updates:

https://www.fintechisfemme.co/

Student debt in America isn’t just a balance sheet problem. It can delay investing, homeownership, entrepreneurship, starting a family, and decades of compound wealth creation.

Few people understand that better than Laurel Taylor, Founder and CEO of Candidly.

Laurel founded Candidly after living the problem herself. She grew up believing higher education was the path to economic mobility, but she and her mother also experienced the long-term cost of financing that dream: years spent paying down debt instead of building wealth.

That experience eventually led Laurel to help create what she describes as the 401(k) for student debt, enabling workers to pay down qualifying student loans while still receiving employer retirement contributions.

But student debt was only the beginning.

In this episode of Humans of Fintech, Nicole Casperson sits down with Laurel as Candidly celebrates ten years and enters its next chapter: building personalized, AI-powered financial guidance across debt, retirement, savings, college planning, and wealth.

They unpack why traditional financial wellness is too fragmented, how workplace-connected data can create a powerful advantage for financial guidance, why enterprise AI requires a much higher trust threshold than consumer AI, and what happens when technology can finally help answer one deceptively simple question:

What should I do with my next dollar?

Laurel also reflects on a decade of entrepreneurship, fundraising through difficult markets, leading with kindness, and why founders sometimes need an almost irrational level of conviction to keep going.

This is a conversation about debt, wealth, AI, trust, and what it would take to make personalized financial guidance available to far more people.

Subscribe to Humans of Fintech for more conversations with the people building the future of financial services.

YouTube Chapters / Timestamps

In this conversation, we dive into:

• 00:00 Why student debt is really a wealth problem
• 00:51 Laurel Taylor and the $1.7T student debt challenge
• 02:10 10 years of building Candidly
• 02:42 The problem Laurel saw before the market did
• 04:33 Why the name “Candidly”?
• 05:24 Inventing the 401(k) for student debt
• 06:23 Building wealth while paying down debt
• 07:45 How AI changes financial guidance
• 09:21 Why trust is becoming fintech’s defining advantage
• 11:20 Candidly’s enterprise distribution model
• 13:00 The “sacred truths” of enterprise AI
• 14:58 Why financial institutions need customer-facing AI
• 16:17 You don’t get to simply declare yourself AI-native
• 17:25 Why fragmented financial wellness is broken
• 18:00 Building personalized AI financial guidance
• 20:40 Moving fast when the margin for error is zero
• 22:25 Turning financial guidance into action
• 24:55 What 10 years taught Laurel about leadership
• 26:39 The irrational conviction founders need
• 28:40 The responsibility of reaching millions of workers
• 29:14 Why Laurel still defines success as kindness
• 31:21 Kindness is not the same thing as being nice
• 33:22 What’s next for Candidly

👇🏼 SUBSCRIBE + FOLLOW HUMANS OF FINTECH

YouTube: https://www.youtube.com/@humansoffintech

Apple Podcasts: https://podcasts.apple.com/us/podcast/humans-of-fintech/id1600731457

Spotify: https://open.spotify.com/show/3zA6yUb3D7I5ZRbehlsdX7?si=42f10417f6e44983

For more fintech news, founder stories, and FTW updates:

https://www.fintechisfemme.co/

AI is making products easier to build.

So what actually separates the companies that win?

In this episode of Humans of Fintech, Nicole Casperson sits down with Drew Glover, Co-Founder of Fiat Growth and General Partner at Fiat Ventures, at the Golden Gate Bridge to unpack the next phase of fintech in the AI era.

Drew argues that as software becomes easier to replicate, the strongest moats left are data, distribution, storytelling, and community.

The conversation explores why fintech may be uniquely positioned in the AI economy, why every scaled technology company eventually starts looking like a fintech company, how founder-led marketing is replacing faceless B2B brands, and why the companies sitting on decades of proprietary financial data may become some of the most important players in AI.

Nicole and Drew also go behind the scenes of FTW: San Francisco, September 29–October 1, and discuss why the next generation of fintech events should feel less like giant trade shows and more like curated rooms where executives, founders, investors, and operators can actually build together.

Because in the AI era, technology may be easier to create.

Trust, distribution, data, and community are not.

Subscribe to Humans of Fintech for more conversations with the people building the future of financial services.

In this conversation, we dive into:

00:00 What still creates a moat in the AI era?

00:54 Drew Glover returns to Humans of Fintech

01:13 Why fintech is missing from the AI narrative

01:59 Every fintech company is becoming an AI company

03:54 Why financial institutions have an AI data advantage

04:19 Build vs. partner: the legacy fintech dilemma

05:57 Is proprietary financial data the real moat?

07:11 Why fintech still struggles to look “sexy”

08:41 Drew’s unconventional path into fintech

10:48 Financial inclusion after the DEI boom

13:43 The B2B fintech storytelling problem

14:48 Why B2B brands now need mass-market storytelling

15:50 The rise of founder-led marketing

17:41 “Data and distribution are the only moats left”

18:43 Why storytelling still gets founders funded

18:53 What FTW: San Francisco is building

20:00 Big Tech × Fintech in San Francisco

21:06 Why curated rooms create better business

23:33 Fintech company Drew is watching

24:28 Why Drew joined FTW: San Francisco

24:48 Community as a moat

25:22 What’s broken about traditional conferences

27:57 Drew’s final takeaway: “I can’t do it alone”

👇🏼 SUBSCRIBE + FOLLOW HUMANS OF FINTECH

YouTube: https://www.youtube.com/@humansoffintech

Apple Podcasts: https://podcasts.apple.com/us/podcast/humans-of-fintech/id1600731457

Spotify: https://open.spotify.com/show/3zA6yUb3D7I5ZRbehlsdX7?si=42f10417f6e44983

And for more fintech news, founder stories, and FTW updates:

Fintech Is Femme: https://www.fintechisfemme.co/

Live from New York: a special mini episode recorded at the Solo Resilience Summit

Nicole Casperson sits down with Josh Arjuna Stephens, SVP of Product at Current, for a sharp, on-the-ground conversation about what it actually takes to build financial products people trust — and use — at scale.

During this special live recording of Humans of Fintech at the Solo Resilience Summit in New York City, Josh and Nicole dig into the evolution of financial infrastructure, the role of agentic AI in product development, why trust has become part of the product itself, and what product teams are most underestimating right now.

🎧 Hit play to hear how today's builders are designing the next generation of financial products — with trust, speed, and compliance all in the same room.

Live from Las Vegas: the Fintech Penthouse is back!

Nicole Casperson sits down with guests Rina Jariwala, Chief Operations Officer at Fundbox, ​Katy Ryan, Partner at Orrick, and Sergio Cordoba, Chief Acquisition Officer at Ontop. During this special live recording of Humans of Fintech at Fintech Meetup 2026, the group discusses’ what it takes to expand past your home market and how compliance, infrastructure, and trust play a role in it.

🎧 Hit play to learn how today’s leaders are scaling across borders and shaping a more connected financial future.

From helping launch Apple Pay at Citi to leading product across servicing, engagement, rewards, and customer experience at Bread Financial, Jyoti Menon has had a front-row seat to how financial services actually evolve.

Jyoti has spent her career building at the intersection of finance, payments, and product — long before “fintech” became the industry it is today. Nicole Casperson and Menon sit down live on the showroom floor of Fintech Meetup in the Humans of Fintech podcast booth to discuss her career path, product development strategies, and the evolving role of AI in fintech.

🎧 Hit play to learn how today’s leaders are scaling across borders and shaping a more connected financial future.

SPONSORED BY FINTECH MEETUP

Fintech Meetup brings together leaders from banks, fintechs, credit unions, and investing firms for 50,000+ one-to-one meetings designed to drive real partnerships and real ROI.

Katy Ryan is a Partner at Orrick, a global law firm focused on serving tech companies, but she’s also a builder, an operator, and someone who’s actually sat on both sides of the table as a founder herself.

Filmed on the showroom floor of Fintech Meetup, Nicole Casperson sits down with Katy to discuss one of the most misunderstood — and most powerful — intersections in fintech: regulation and growth.

🎧 Hit play to learn how today’s leaders are scaling across borders and shaping a more connected financial future.

SPONSORED BY FINTECH MEETUP

Fintech Meetup brings together leaders from banks, fintechs, credit unions, and investing firms for 50,000+ one-to-one meetings designed to drive real partnerships and real ROI.

Danny Friday isn’t your traditional fintech founder. Originally a software engineer, Sail was born out of necessity to create accessibility in our healthcare system’s reimbursement process.

Filmed at the Fintech Penthouse in Las Vegas during Fintech Meetup, Nicole Casperson sits down with Sail’s Founder and CEO to unpack one of the most complex, high-stakes, and misunderstood systems in our economy — and how Sail is building the infrastructure to fix it.

🎧 Hit play to learn how today’s leaders are scaling across borders and shaping a more connected financial future.

SPONSORED BY FINTECH MEETUP

Fintech Meetup brings together leaders from banks, fintechs, credit unions, and investing firms for 50,000+ one-to-one meetings designed to drive real partnerships and real ROI.