Middesk

Do you think — or do you know? That question has been stuck in my head ever since I read Middesk’s Trust Thesis and the letter from CEO Kyle Mack. And after a week of conversations at Money20/20, I know I’m not the only one asking it. Because for all the talk about faster payments and more intelligent AI… There’s one word that kept surfacing — in panels, off-stage meetings, and those rare, unfiltered late-night convos: Trust. But not as a marketing buzzword. As a reckoning. We’re moving faster than ever — across markets, across borders, across platforms. But what happens when speed outpaces certainty? When onboarding breaks before it begins? When “authenticity” can be AI-generated? That’s what tonight's Fintech Is Femme newsletter column is about. I sat down with Jackie Wylie, Head of Marketing and Sales Dev at Middesk, and Rina Jariwala, COO of Fundbox, at the Fintech Is Femme AI Summit to explore what trust actually looks like in motion — not just as a value, but as an operational layer. What stuck with me? → That trust isn’t built in dashboards — it shows up in the decisions teams make when no one’s watching. → That EQ isn’t soft — it’s what lets you lead through layoffs and still build momentum. → That the companies who survive the next few years won’t just be the fastest or best funded — they’ll be the ones people believe in. So much of fintech’s next chapter won’t be decided by product features or funding rounds. It’ll be decided by whether we can build systems — and relationships — people trust. 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. That’s the story. Coming to your inbox at 8:45 pm ET tonight. And it’s one I’ll be thinking about for a while. 👀 I look forward to seeing you in your inboxes. 💜

The Middesk team showed up big at Money20/20 and I couldn’t be prouder of what we built together. What started as a creative idea to make “trust” something people could see, touch, and wear, turned into a full-blown retail experience that stopped people in their tracks. The Trust Club pushed the boundaries on what a trade show booth should be, and became space that made trust feel less like a corporate buzzword and more like a culture. Every detail was intentional. The shelving, the lighting, the typography, the playlist, and the merch. All of it was designed, written and sourced by this team. From concept to launch, they spent months obsessing over the smallest details, staying late to perfect copy, finalize samples, and rehearse every inch of the customer experience. Our booth became the hottest Club in Vegas. Duffles were gone within hours. Our shopping bags became a fixture on the show floor. We were slammed from opening to close, and still the team kept smiling, greeting, restocking, filming, troubleshooting, and making it all look effortless. It wasn’t effortless. It was hard work, long hours, and intense collaboration. And it was so worth it. I’ve never been prouder of this team. For the creativity, the craft, the hustle, and the heart that went into making an abstract idea real. To the Middesk team: you made something extraordinary, and I’m endlessly grateful to have been part of it 💚 🖤 Kate Young, PhD, CMP, Executive Producer of the Trust Club 🪩 Maranda Idoni, Director of Trust Club Vibes 🎨 Scout Stowe, Creative Director of Trust Club Aesthetics 👑 Gabrielle Bier, Trust Club Content Queen 🐝 Yvo C., Director of Trust Club Buzz ⚙️ Emily Kucharczyk, Head of Trust Club Operations 📊 Leigh Kloss, Head of Trust Club Product Experience 📷 Photo credit: Renowned Photos