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- 🤑 Do you think, or do you know?
🤑 Do you think, or do you know?
In a world of AI deepfakes and compliance chaos, fintech’s edge isn’t automation — it’s authenticity. Middesk’s Jackie Wylie and Fundbox’s Rina Jariwala share how to turn trust into infrastructure, and EQ into ROI.

Hey, fintech fam! 💜
Survived Money20/20? Same. After a quick hibernation, the Fintech Is Femme team is back in build mode—debriefing what we learned, tightening what worked, and mapping the next chapter.
If this year taught me anything, it’s that our industry still runs on community.
Products matter. Distribution matters. But the flywheel is trust—between founders, partners, customers, and enterprises who are willing to collaborate. Too few are investing in that muscle. We are.
That’s the bar for our 2026 slate: programs and partnerships that compound trust, not just impressions (we like those too). We’re designing stages where ideas meet accountability, capital meets community, and the right people find each other faster.
Here’s what’s on deck for 2026 (and already in motion):
Fintech Penthouse series @ Fintech Meetup — intimate, high-signal salons and live recordings March 30-April 1, 2026.
New York Fintech Week — Leadership Summit + Security Summit focused on execution, resilience, community, and real-world AI. (Save the date: April 22, 2026).
San Francisco Fintech Week — Fintech, AI, and Security Summits built for builders, risk leaders, and growth teams. (Coming Fall 2026).
Money20/20 2026 — back, bigger, and louder—scaling the Penthouse experience on site.
I’m already deep in planning with core partners and curating where each story belongs.
If you want to co-create something meaningful—content, summits, research, or brand moments that actually move the needle—hit reply with “2026” and a line on your goals.
We’ll carve out time this month. Inventory is limited and filling fast.
Let’s make next year the year we operationalize trust—and grow because of it.
Let’s get into it.
INNOVATION
Fintech’s Next Currency Is Trust: Inside How Middesk and Fundbox Are Rebuilding the Foundation of Growth

Jackie Wylie, Head of Marketing and Sales Development at Middesk, and Rina Jariwala, Chief Operating Officer at Fundbox, take the stage at the Fintech Is Femme AI Summit, Oct 8, 2025. San Francisco.
When I walked into Money20/20 this year, one word kept following me — from the Summit stages to private meetings to late-night penthouse sessions: trust.
It wasn’t a buzzword. It was a reckoning.
For all the progress fintech has made — from real-time payments to agentic AI to the rise of embedded finance — we’ve entered an era where technology has outpaced trust.
The rails are faster, but the relationships riding on them are weaker.
As one founder shared, “Businesses move faster than institutions can keep up. If we don’t rise to meet this moment, trust collapses when it matters most.”
That founder was Kyle Mack, CEO and co-founder of Middesk, whose company just released The Trust Thesis — a framework that defines trust as the next great infrastructure layer of finance.
And after interviewing Jackie Wylie, Head of Marketing and Sales Development at Middesk, and Rina Jariwala, COO of Fundbox, at the Fintech Is Femme AI Summit in San Francisco, one thing is clear:
Trust is the new currency.
And it’s one that will decide which companies endure the next wave of disruption — and which fade into the noise.
Do You Think, Or Do You Know?
Every transaction begins with one question: who’s on the other side?
At a time when 1 in 5 new business applications are flagged for first-party fraud, and nearly 30% of businesses in the U.S. are conducted online and growing year over year, the foundation of fintech — identity — has never been more fragile.
The consequences are real: banks and fintechs lose an estimated $20 billion a year to onboarding delays and compliance inefficiencies. 2025 data indicates that 70% of financial institutions lost clients in the past year due to slow onboarding, the highest rate ever recorded.
And yet, most businesses still rely on patchwork data and outdated verification systems.
That’s the gap Middesk is solving.
Middesk’s platform helps financial institutions “trust faster” — giving banks, lenders, and payment platforms a real-time view into who they’re working with. Middesk’s work sits at the intersection of risk, compliance, and confidence — helping banks, lenders, and fintechs verify the legitimacy of the businesses they serve.
As digital onboarding becomes the norm, so does the challenge of knowing who’s really on the other side of a transaction.
Their model reframes compliance from a procedural burden into a strategic advantage, not as a cost center, but as a growth engine — because when you can trust your counterparties, you can move faster, serve better, and innovate freely.
By integrating verification into the flow of business, Middesk aims to make trust a measurable, operational layer of modern finance — one that determines how quickly institutions can make decisions, extend credit, and scale partnerships.
In that sense, trust becomes infrastructure — the unseen system that enables every transaction, partnership, and ecosystem to function with confidence.
Trust as Emotional Intelligence in Action
On stage at the Fintech Is Femme AI Summit, Jackie Wylie framed trust as more than a legal checkbox or a brand metric.
“Trust can’t be a gut feeling anymore,” she said. “There’s too much at stake. Fraudsters are more capable than ever. Trust has to be built on both empathy and facts.”
For Wylie, trust isn’t abstract. It’s operational. She calls it “EQ in action” — a system that scales credibility.
Her example? Middesk’s “Trust as a Lifestyle” campaign, which turned their Money20/20 booth into a high-end boutique filled with symbols of authenticity and integrity.
The concept was born out of frustration: too many fintechs treat trust like a compliance manual, gathering dust on a shelf.
“We wanted to make trust experiential — something you live and show up with every day,” Wylie explained.
That philosophy shaped Middesk’s partnership with GreatAmerica Financial Services. When they started working together, GreatAmerica’s team admitted they didn’t trust their own data. So Middesk didn’t just deliver better information; they built a relationship rooted in collaboration and transparency.
From that partnership came what Wylie calls the “trust flywheel”:
Lead with empathy.
Build confidence through transparency.
Accelerate growth through consistency.
“If you can help your customers know who they’re working with, trust the decisions they’re making, and grow their business — that’s when trust turns into momentum,” she said.
And that flywheel spins in both directions: for customers, and within teams.
The EQ Equation: Leading With Clarity, Not Control

If Wylie represents the architecture of trust, Rina Jariwala of Fundbox represents its heart.
“IQ gets you the plan,” Jariwala said. “But EQ rallies the team to deliver on it.”
At Fundbox — a platform powering working capital for businesses — Jariwala has led through some of the most turbulent times in fintech.
In 2022, Fundbox was forced to make difficult decisions to survive a shifting market, parting ways with half its workforce.
Rather than retreat, she led with radical transparency.
“We showed the team exactly what KPIs to watch, every milestone we had to hit, and how their work directly influenced our runway,” she recalled.
The result? Fundbox not only recovered — it built 10+ years of runway and regained profitability.
“When people understand why you’re doing what you’re doing, they trust you. And when they trust you, they execute with confidence.”
Her leadership lesson is deceptively simple: trust is built through clarity, not control.
That transparency turned surviving into thriving — a blueprint for every fintech leader navigating the uncertain years ahead.
Turning Trust Into a KPI
Both Wylie and Jariwala agree: trust may never fit neatly into a dashboard, but it shows up everywhere — in retention, referrals, and resilience.
“Trust isn’t just about onboarding speed or conversion,” Wylie said. “It’s measured in how long your customers stay, how much they grow with you, and how deep the relationship becomes.”
Or as Jariwala added,
“When your customers start opening doors for you — that’s when you know you’ve built trust into your product.”
At Middesk, that belief inspired the mantra “Know. Trust. Grow.”
It’s a simple idea with radical implications:
Know every business you serve.
Trust every decision you make.
Grow with confidence.
In a market obsessed with efficiency, Middesk and Fundbox are reminding fintech of something fundamental: efficiency means nothing without integrity.
Because when AI can fake intelligence, when deepfakes can clone credibility, and when regulation can’t keep up with innovation — the only differentiator left is trust.
Why It Matters

In an industry still recovering from a wave of overfunding, layoffs, and rebranding in the age of AI, resilience is the most valuable asset of all.
Fintech’s next chapter won’t be written by those who raised the biggest round or scaled the fastest. It’ll be written by those who built the deepest trust — across teams, customers, and communities.
Growth doesn’t start with scale — it starts with certainty.
Certainty is built on confidence.
And confidence only comes from experience — from the lessons, the setbacks, and the trust we build along the way.
The Future of Trust
At its core, trust is the bridge between technology and humanity — between what fintech can automate, and what it must still earn.
And the women leading this conversation — from Jackie Wylie turning compliance into connection, to Rina Jariwala transforming transparency into growth — are showing us how to operationalize it.
Because trust doesn’t just make fintech safer.
It makes it human.
It reminds us that we’re an industry built on relationships.
And that’s the foundation that will carry us through the chaos of the next few years — one handshake, one story, and one act of honesty at a time.
#SPONSORED
WhatsApp Business Calls, Now in Synthflow
Billions of customers already use WhatsApp to reach businesses they trust. But here’s the gap: 65% still prefer voice for urgent issues, while 40% of calls go unanswered — costing $100–$200 in lost revenue each time. That’s trust and revenue walking out the door.
With Synthflow, Voice AI Agents can now answer WhatsApp calls directly, combining support, booking, routing, and follow-ups in one conversation.
It’s not just answering calls — it’s protecting revenue and trust where your customers already are.
One channel, zero missed calls.
I WANT IT, I GOT IT
🎧 Today’s Listen: I’ve got a lineup of new podcast episodes dropping soon from Money20/20 — but while those are in the edit bay, I’m throwing it back to one of my favorite conversations from Humans of Fintech. This special episode features two powerhouse leaders: Nicole Mitchell, Partner at Aprio, and Tiffany Haynes, investor, advisor, and former COO of Fingercheck. Tune in to learn how to zoom out, see the bigger picture, and grow businesses that last.
🚀 Today’s Watch: Over Halloween weekend, a group of friends convinced me to watch The Shining — for the first time ever. I’ll admit it: I’m not a horror movie person. (I’m usually the one hiding behind a pillow five minutes in.) But this one? Iconic. Atmospheric. And honestly… not too scary — at least, not for my threshold. There’s something timeless about it — the slow-burning suspense, the visual storytelling, the way it explores isolation and obsession. It’s less about jump scares and more about the psychology of unraveling — which, if we’re being real, might be the most chilling part of all. 10/10 recommend if you want a classic that’s creepy without the nightmares.
🧘♀️Today’s Self-Care: After a whirlwind October — moderating panels, directing content, producing multiple events across multiple cities (with hundreds of you! showing up 💜) — my body officially tapped out and demanded recovery mode. So, I’ve been leaning hard into self-care. My go-to ritual? A massage a week to keep my nervous system in check, and plenty of hot yoga to reset my energy (and my posture). In fact, as you read this, I’m probably mid–sweat session in my second hot yoga class of the week. Here’s your reminder: you can’t pour from an empty cup — so fill yours first. Let’s get it.
FINTUNES
99% certain I walked by Rosalia on the streets of NYC.

LET’S CONNECT
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📚 The holidays are coming, in charge of purchasing office gifts? Grab my book, Fintech Feminists! It looks nice on the coffee table 😉
That wraps up today’s edition—thanks as always for reading! Until next time, keep innovating and challenging the status quo.
See you Thursday!
Love,
Nicole 💜

