The Way In

New New Patch was named in TIME’s Best Inventions of 2026 Special Mentions . Prue spent 18 years in product marketing before becoming a founder herself. New New Patch started with a very ordinary parenting problem: what do you do when your kids’ clothes are stained? Her answer was a peel-and-stick patch that makes repairing and personalizing clothes as easy as putting on a sticker. But turning tha...

Tim, founder of Bonsai Bar, discovered bonsai while working in software and eventually started wondering not just how he could make a living from bonsai, but how he could help grow the economy around the hobby. That idea eventually became Bonsai Bar. What started with small workshops in Boston has grown into a business operating across 18 states, with roughly 200 part-time instructors and more tha...

AI tools for investment research have exploded over the past year, but more information doesn't necessarily make research easier. In fact, it can make it harder to know what to pay attention to. In this episode, I talk to Tiffany Qiu, founder of Oxbridge Economics and the company behind FinFAST, an AI platform that turns unstructured macro and policy data into quantitative, decision-ready signals....

Natasa Tuohy grew up in Yugoslavia, moved to Florence at 19 to study architecture, and made her way to New York, where she spent nearly a decade working in architecture before starting her own studio in 2019. In this episode, we talk about that journey from Florence to New York, what she learned working inside established architecture firms, and what changed when she became responsible for not jus...

In this episode, I’m joined by Kim, founder of Utopia Club, a private community for software founders making high-stakes decisions around entering and scaling in the U.S. market. Kim started her career as a fractional marketing operator and founded Fua Collective three years ago. After working closely with founders, she noticed a recurring problem: founders were often making major business decisio...

Sports gels are everywhere in North America, but in much of Asia, the bigger challenge isn't convincing someone to switch brands - it’s convincing them to use a gel in the first place. In this episode, I’m joined by Anthea, founder of ANS, a Singapore-based sports nutrition brand built around the idea of “performance for the long run.” We talk about why she saw an opportunity to rethink the relati...

What does it actually take to build a jewelry business? She didn't start with Instagram. She didn't start with a consumer brand. She didn't chase trends. She didn't prioritize rapid scale. She didn't build a big team. Instead, Laura started in jewelry distribution, eventually building relationships with museum shops and airport retailers before putting her own name on the label and moving online....

After more than a decade in product marketing, Maggie left her corporate career in November 2024 without even knowing the term “portfolio career.” She initially thought she was simply making a pivot into events. But as she began freelancing, coaching, teaching, creating content, and taking on fractional marketing work, she realized she was building a career made up of multiple interests and income...

Eric left what many people would consider a dream job at Google after realizing that achievement alone wasn't enough. What he was missing was community, a realization that eventually led him to co-found Heylo, a platform that helps thousands of running clubs, hiking groups, book clubs, and social communities organize real-world activities. In this episode, Eric shares how a lonely marathon sparked...

When Miles left a stable career in biotech, he wasn't chasing the next startup idea. Instead, he began serving free tea in New York City parks— no agenda, just an open space for strangers to slow down and connect. What started as a simple experiment has since grown into The Tea Stand, a nonprofit that has poured more than 12,000 cups of tea, published a biannual zine, shipped hundreds of tea boxes...

In this episode, I sit down with Leeah, founder of Newberry Travel. After leaving a career in corporate sourcing, Leeah realized that just as every purchasing decision can shape a factory and its community, every travel dollar can shape the people and places we visit. She shares how a four-month journey across all seven continents inspired her to build a company centered on conscious travel, docum...

Ricky sold his first startup at 23. Instead of taking a break, he jumped straight into building SourceReady , an AI platform that helps companies source top products from global suppliers. In this episode of The Way In , Ricky shares his vision of building the “Google search for supplier data” . Why now? In 2025, the U.S. collected $287B in customs duties - up 192% year-over-year. For the first ti...

In a beauty industry obsessed with greenwashing and Amazon scale, Kate Assaraf, founder and CEO of Dip, chose a different path. In this episode of The Way In , Kate shares how she built a 7-figure haircare brand rooted in community and clear positioning. We talk about early product development, her decision to grow without Amazon, and why brand positioning matters more than massive distribution. S...

In this episode of The Way In , I speak with JJ Ram, CTO and co-founder of Claim Health , about his journey from a start-up bouncer to building an AI company for the $100B+ U.S. home health industry. JJ shares how he and his co-founder navigate the challenges of running a startup together - combining deep tech expertise with the operational knowledge of their clients and learning how to complement...

In this episode of The Way In , I speak with Trevor, CTO of Olive Legal, about stepping into leadership at a company he didn’t start. Trevor joined Olive Legal as the first engineering hire, drawn by the chance to learn from experienced founders. When those founders later moved on to a new venture, Trevor was faced with an unexpected opportunity: take over a revenue-generating business while untan...

In this episode of The Way In , I speak with Eric and Dev, the founder duo behind Marmalaide, a company using generative AI to create high-quality marketing content. Eric shares his background as an independent filmmaker and how the writers’ and actors’ strikes pushed him to experiment with AI, leading to a viral parody video that helped catalyze Marmalaide’s early momentum. Dev breaks down the bu...

In this episode of The Way In , I speak with Sid Sridharan, co-founder and CEO of Spendflo, about the evolution of the company from SaaS spend management to an AI-native platform. Sid shares lessons from founding and scaling Spendflo, the role of venture capital, the difficult decision to exit a market, and why he’s now focused on building AI teammates to reshape how procurement work gets done.

In this episode, Sol shares her personal journey with prenups and how Neptune is changing the narrative around these conversations. We discuss the lessons she learned from her first startup, the challenges couples face when talking about money and prenups, and how Neptune aims to simplify the process through education and access to trusted experts. Sol also reflects on the role of AI in legal matt...

Brian, founder of Verteel, didn’t start out in tech - he started in the cockpit. In this episode, Brian shares his journey from being a professional pilot to building a drone company focusing on transforming medical logistics. He discusses the challenges of navigating regulatory environments, the importance of customer discovery, and the innovative approaches Verteel is taking to improve healthcar...

In this episode, Maggi shares the journey behind Sumly, from its early prototype to its official launch after a year of development. During pilot testing, users saw an average savings of $2,350 , a clear signal that the product was solving a real and painful problem. From meeting her co-founder at Columbia to building a product focused on putting money back in users’ pockets, Maggi offers an hones...

Kartik’s journey checks all the classic tech-founder boxes -MIT dropout, YC alum - but the real story begins when he walks away from his first product. After realizing their hedge-fund modeling tool wasn’t sticking, he made a sharp pivot into a far more chaotic world: medical billing. With insights from his physician father and dozens of billers, Kartik quickly saw how broken and costly the system...

Dana’s path to founding Selformer Pilates is far from traditional. After nearly 20 years as a music photographer - constantly traveling and carrying heavy gear - she turned to Pilates to repair her body, eventually discovering a new calling. With no business background, she built Selformer by embracing her “misfit” identity and trusting her creative instincts. Based in the fitness-saturated neighb...

Launching a startup is often about timing - and Gu’s journey with Adzviser is a perfect example. As he was building the first version of the product, ChatGPT launched, creating a sudden surge of interest in AI tools. The timing was serendipitous: Adzviser quickly became one of the first tools recommended by OpenAI, giving it an early edge in the market. But timing alone doesn’t build a business. G...

Alvina, founder of SHUMINGYU, didn’t come from a traditional fashion background. A humanities student who later worked at Christie’s, she draws inspiration from a wide range of artistic genres and notices the subtle nuances in Chinese culture. From classical poetry to watercolor paintings, Alvina shares how Chinese art informs her clean, contemporary silhouettes, and how she creates clothing that...

In this episode, Kiki, co-founder of Sourmilk, breaks down how she built a sold-out yogurt brand in record time. In just 10 months, Sourmilk landed on shelves at two NYC grocery stores, sitting right next to industry giants like Chobani. Was it luck, relentless hustle, or the right partnership at the right time? Kiki shares how social media became her most powerful growth engine, what she’s learne...