John Andrew Entwistle is the founder and CEO of Wander—a company blending real estate, software, and hospitality to create a radically better way to travel.

John Andrew started young. At 13, he was running game servers and managing six-figure revenue. By 18, he’d co-founded Coder, raised $50M+, and partnered with giants like Palantir and Goldman Sachs. But after leaving that company, he set out to solve something more personal: why is booking a vacation rental still such a gamble?

Wander began as a vertically integrated hospitality brand—buying and operating luxury homes. But over time, it evolved into something bigger: a fully software-driven infrastructure layer for managing high-quality stays at scale. Powered by Wander OS and coordinated by AI agents, the company now runs thousands of homes without compromising on guest experience.

We talked about what it takes to build a brand customers love, why he optimizes for values over credentials when hiring, and how software—not scale—lets Wander promise the same standard, every time. John also opened up about his childhood rules for living, his philosophy of “massive good,” and what it means to build a company worth running into old age.

Learn more about John Andrew and his company below:

linkedin.com/in/jaentwistle/

wander.com/

Aaron Bai is the co-founder and CEO of Affiniti—a fintech company building a financial operating system for overlooked small businesses, starting with a no-fee credit card.

Aaron started college at 16, dropped out at 17, and raised his first round shortly after. His first company, a neobank, failed—strong product, weak market fit. So he reset. He and his co-founder spent months reading 10-Ks, talking to small business owners, and figuring out why existing fintechs weren’t working.

They landed on a simple insight: trust is the bottleneck. Most SMBs don’t need more features—they need something they believe in. Affiniti’s wedge is the card, but the goal is deeper: become the financial back-end for businesses that don’t have a CFO.

We talked about underwriting human risk, why most fintechs chase the wrong SMBs, and how Affiniti is turning everyday transactions into a data-rich, trust-first engine for financial clarity.

Learn more about Aaron and his company below:

linkedin.com/in/aaronybai/

affiniti.finance/

Marty Kausas, is the co-founder and CEO of Pylon—a post-sales CRM redefining how B2B companies manage customer relationships after the close.

Marty grew up in San Diego after his parents immigrated from Lithuania following the fall of the Soviet Union. He was writing code before he could vote, living off lentils, and leading Purdue’s elite hacker group by 19. But it was two tough years of “pivot hell”—false starts, failed ideas, and no clear path forward—that laid the real foundation for Pylon.

What began as a simple integration between Zendesk and Slack quickly revealed a deeper opportunity. After consistent feedback from B2B teams, Marty and his co-founders realized that legacy tools weren’t built for the complexity of modern post-sales.

Today, Pylon serves over 500 customers—replacing fragmented point solutions with a unified platform purpose-built for how B2B teams actually work.

We talked about Marty’s unorthodox path from robotics to startup resilience, why “sell before you build” should be the default, and how shared context—not just tickets—is the currency of modern post-sales teams.

We also dug into how Pylon raised $20M in record time without a pitch deck, why they’re betting big on video-first marketing, and what it means to build a $10B company that’s optimized for fun.

Learn more about Marty and his company below:

linkedin.com/in/martykausas/

usepylon.com/

Yash Sheth is the co-founder and COO of Galileo—a platform helping enterprises measure, test, and scale AI applications with confidence.

Yash’s journey started in Mumbai, moved through investment banking at JP Morgan, and shifted into engineering at Google, where he helped build core parts of the conversational AI stack behind products like Google Assistant and Glass. It was there he saw the real challenge: getting powerful models into production without breaking trust.

That’s what led to Galileo.

What began as a focus on data quality has evolved into a full-stack evaluation platform—used by leading enterprise teams to measure performance, prevent regressions, and ship AI features with confidence. Galileo is now 11x faster and 97% cheaper than traditional eval tools—and built from the ground up for production-scale use.

We talked about Yash’s transition from finance to AI, lessons from scaling models inside Google, and why measurement—not modeling—is the missing layer in most AI stacks. We also got into Galileo’s agentic evaluations, the limits of generic metrics, and what it really takes to deploy AI you can trust.

Learn more about Yash and his company below:

linkedin.com/in/yash-sheth-/

galileo.ai/

Nelson Chu is founder and CEO of Percent—a capital markets platform bringing transparency, liquidity, and standardisation to private credit.

Nelson’s path started with a $1,000 “experiment fund” from his dad and early side hustles in design. After stints at Merrill Lynch and BlackRock, he left corporate life behind, built a consulting firm that helped raise over $1B, and used that momentum to launch Percent.

What began as a short-duration credit platform with $500 minimums has evolved into the infrastructure behind over $1.5B in transactions—now positioning itself to power the future of a $25T market.

We talked about Nelson’s journey from design to finance, how art influences his thinking, and what it takes to earn trust in a space that’s opaque by design. We also dug into Percent’s tech, regulatory approach, and long-term plan to bring public-market efficiency to private credit.

Learn more about Nelson and his company below:

linkedin.com/in/nelson-chu/

percent.com/

Cobi Blumenfeld-Gantz is the co-founder and CEO of Chapter—the most consumer-aligned Medicare guidance platform in the U.S., built to radically improve how seniors navigate retirement.

He grew up hearing stories of his family’s journey across borders and generations—from Havana to Rochester, New York. That early exposure to resilience, migration, and responsibility shaped everything that came next—from studying at Cambridge to working at Palantir, where he learned how to navigate complex, regulated systems.

Then came a turning point: watching his own family struggle to make sense of Medicare. That experience sparked a question that would drive the next chapter of his life—what if there were a better way to help people age with clarity, trust, and dignity?

With Chapter, Cobi is building just that. Backed by industry leaders and growing 4x year-over-year, it’s the only Medicare brokerage invited to testify before Congress. And it’s setting a new standard—where incentives are aligned, ethics are built into the product, and seniors are treated not as leads, but as people.

We talked about the broken state of Medicare, the hidden incentive structures shaping the industry, why most startups underestimate the power of distribution, and how Chapter is quietly laying the foundation for a more human future of retirement.

Learn more about Cobi and his company below:

linkedin.com/in/cobibgantz/

askchapter.org/

Zac Townsend, the co-founder of Meanwhile—a life insurer where everything runs on Bitcoin: premiums, payouts, and reserves.

Zac grew up watching his father work as a postal clerk by day and study for his BA, MA, and PhD by night. That early exposure to discipline, sacrifice, and long-term ambition shaped everything that came next—from studying finance not to join Wall Street, but to understand how the system worked, to working in civic tech under Cory Booker, where he was tasked with figuring out why people in West Newark didn’t have bank accounts.

That question sparked a decade-long journey into financial infrastructure: first at Stripe, then co-founding Standard Treasury—an early banking-as-a-service startup later acquired by SVB.

Now, with Meanwhile, Zac is going even deeper. Backed by Sam Altman and licensed in Bermuda, he’s building a Bitcoin-native life insurer designed to protect families in places where inflation makes traditional savings impossible—like Nigeria, Argentina, and even parts of the U.S.

It’s simple: customers pay in Bitcoin, receive payouts in Bitcoin, and hold policies that grow in value—not lose it.

We talked about his life as a founder and father, why traditional life insurance is broken, what most entrepreneurs get wrong about focus, and how Meanwhile could help lay the foundation for a Bitcoin-based financial system.

Learn more and Zac and his company below:

linkedin.com/in/zactownsend/

meanwhile.bm/

Matthias Wagner is the founder of Flux, a collaborative, AI-native hardware design platform. But to call it that almost undersells it. What Flux is really doing is dragging hardware into the modern age—giving engineers the same creative velocity that software teams have enjoyed for decades.

The status quo in hardware design? Obsolete. Legacy PCB tools that haven’t changed since the ‘80s. No collaboration. No browser access. Locked behind $20,000 licenses. Engineers emailing project files. No GitHub, no Figma, no AI.

Matthias saw the absurdity firsthand.

In 2019, he left Meta—where he’d worked on Moments, AR/VR, and Oculus Quest—and took a summer off to build electronics for Burning Man. That’s when it hit him: this shouldn’t be this hard. Designing a basic board was painful. Tools were ancient. Workflows felt frozen in time.

So he started Flux.

He didn’t just want to modernize PCB design—he wanted to rethink it from first principles. Make it multiplayer. Make it programmable. Build it for the web. And inject AI into the workflows engineers hate most: routing traces, sourcing components, catching errors. Today, Flux is used by thousands—from African farmers building smart irrigation systems to world-class engineering teams shipping real hardware.

But here’s what makes Matthias different: he’s not chasing enterprise contracts. He’s not building for committees. He’s building for the individual. The 12-year-old with an idea. The kid who wants to build their own iPhone, not just an app. The founder in Nairobi who can’t afford $20K software but can learn online and make something real.

His worldview is equal parts sci-fi optimism and Burning Man pragmatism. He talks about LEGOs as foundational infrastructure. He sees Star Wars as a blueprint for the future (where a kid in a desert can build a sentient robot). And he believes the next industrial revolution won’t be driven by centralized R&D—but by distributed, AI-augmented creativity.

Flux isn’t just Figma-for-PCBs. It’s Figma and GitHub and OpenAI—for hardware.

And he’s not stopping.

The roadmap? Even more automation. Even less friction. A world where hardware engineers can work with AI agents just like software devs do—except they’re not just writing code, they’re creating physical things. Devices. Machines. Systems.

And the philosophy underneath it all? Simple: the future is obvious if you’re willing to unlearn the past.

This one stuck with me. Matthias isn’t loud. He’s not trying to be a hype machine. He’s just building—calmly, relentlessly—toward a future where anyone, anywhere, can create the physical tools they need to change their world.

And honestly? He might actually pull it off.

Learn more about Matthias and his company below:

linkedin.com/in/matthias-wagner-5220b047/

flux.ai/

Micha Benoliel's not just building a crypto network—he’s chasing a decades-long dream to make global connectivity free, sovereign, and owned by the people.

His company, Nodle, turns every smartphone into a low-energy base station—quietly building one of the largest decentralized wireless networks on the planet. No cables. No towers. No telecom monopolies. Just phones, sensors, and incentives.

But to really get Micha’s story, you have to go back.

He’s been hacking communications for 20+ years. In 2004, he helped Skype connect to mobile and landlines before anyone thought that was possible. By 2012, he was building mesh networks at Burning Man to help people message each other without cell service. That prototype became FireChat—a peer-to-peer messaging app that would go viral during the Hong Kong Umbrella Movement. No internet required. Just phones bouncing Bluetooth signals.

10 million people used it. And then? He got pushed out of his own company.

He didn’t stop.

Now with Nodle, he’s picking up where he left off—this time with crypto and edge tech. Phones become infrastructure. Users get paid in tokens just for participating. Enterprises already use it to recover stolen vehicles in Europe, track motorcycles in Africa, and monitor drivers for insurance underwriting.

And he’s just getting started.

What’s coming next? Messaging. Stablecoin payments. And AI agents. Yes—Micha’s building a wallet where you can earn, message, and eventually ask AI to handle your crypto interactions for you. He’s already shipped an AI-powered photography coach in Nodle’s camera app, and he’s building more into the core wallet experience.

The longer you talk to him, the more it clicks: Micha isn’t just building an app—he’s laying down the rails for a sovereign communication and financial layer, where billions of people can earn, transact, and connect—without middlemen.

He’s done it without paid installs. Without hype. Just product, persistence, and deep conviction.

This one stuck with me. In a world of overfunded noise, Micha’s quietly building something foundational. Not just for crypto. For infrastructure. For freedom.

And if he’s right—one day, your phone won’t just be a screen in your pocket. It’ll be your node, your wallet, your ID, your bank—and your link to a new kind of network: open, global, and owned by you.

Learn more about Micha and his company below:

linkedin.com/in/michabenoliel/

nodle.com/

Zach Lloyd's reinventing how every developer on Earth talks to a computer—and he might actually pull it off.

Right now, half a million devs use his company, Warp, a modern AI-powered terminal. But it’s what’s under the hood—and how he thinks about building—that sets him apart.

He’s lived many lives: law school dropout, philosophy major, musician, NASA systems analyst, principal engineer at Google. At Google, he scaled Sheets through 40x growth and helped shape the real-time collaboration model we now take for granted. Then he left. Why? He wanted to fix something most people wouldn’t touch: the terminal.

That blinking black box you see hackers using in movies? Developers still use it—the exact same interface—to build and deploy the internet. It’s powerful, but brutal. No mouse support. Cryptic errors. Zero collaboration. And no one dared change it. Too much risk of breaking things. No obvious business model. Total founder graveyard.

Zach saw an opportunity.

He calls it “building the bridge”—making Warp 100% backwards-compatible, so devs could bring their scripts, habits, and workflows—but layered with modern UX and AI. Clickable outputs. Instant command suggestions. Error correction. It’s like putting a co-pilot inside the terminal.

And now, Warp is going full-on AI agent mode. Zach’s vision? Developers won’t type commands. They’ll just tell their computer what to do. Deploy the backend. Debug the crash. Set up the dev environment. And Warp will just do it—autonomously, with memory, and context from your entire team’s knowledge base (Warp Drive).

He’s not naive about the competition either. He knows he’s in one of the most high-velocity races in tech right now—AI dev tools. But he’s betting on deep product quality, performance (they rewrote everything in Rust), and speed. Internally, they ship fast and joke in Slack with a hashtag: #warpspeed.

Also—his fundraising journey is wild. Didn’t pitch dozens of VCs. Didn’t need to. Dylan Field (Figma) led his Series A. Sequoia led his Series B. Sam Altman, Benioff, Elad Gil, Jeff Weiner—some of the sharpest minds in tech are already behind him.

And the endgame? Warp becomes the interface where devs orchestrate AI agents to build software. He doesn’t want to replace developers—he wants to amplify them. Let AI handle the toil, so humans can focus on the fun, creative parts of building.

This one hit different. Zach’s not chasing hype—he’s quietly building one of the most foundational tools in the new stack. And if he’s right, in a few years, we won’t be typing commands. We’ll just say what we want—and Warp will make it real.

Learn more about Zach and his company below:

linkedin.com/in/zachlloyd/

warp.dev/