The Way In

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...

Chef Cipollone knows what it takes to earn a Michelin star -and more importantly, to keep one. In this episode, he shares how years in top kitchens shaped his approach to leadership, creativity, and building a team that lasts. We talk about the mentors who pushed him, the lessons behind Francie’s success, and how his new project, Allegretto , brings together design, energy, and heart in a whole ne...

Logan started out as a Paulie Gee’s fan - now he’s behind the counter running his own location in Gowanus. In this episode, he shares how a love for great pizza turned into a full-time pursuit, what he learned opening a restaurant in New York City, and why consistency, community, and craft matter more than ever in the food business. Chapters 01:05 The Journey into Pizza Making 04:39 Training and L...

This episode is full of energy, grit, and heart — just like Kiah herself. After years in the Bay Area restaurant scene and co-founding Far Out Catering , Chef Kiah Fuller took a leap to start Plated by Chef Kiah — a private dining brand that brings high-end experiences to people’s homes and communities. In this episode, Kiah shares what she learned from her time in fine dining, the scrappy early d...

In this episode of The Way In, I sit down with Daniel, the new owner of three PingPod franchise locations in Williamsburg, Downtown Brooklyn, and the Lower East Side. Daniel shares what inspired him to move from investor and advisor to franchise owner, his transition from analyzing businesses to operating them, how he's applying his analytical toolkit to optimize pricing models and community build...

When it comes to protein bars, 99% of the market is dominated by chocolate or peanut butter flavors. Frustrated by the lack of variety, Gene set out to create something different - savory protein bars inspired by international flavors. After hundreds of recipe iterations, he and his mom hand-made 40,000 bars at a commercial kitchen. Four years later, Afar Foods’ savory bars can now be found in air...

From her early days as a hostess at COTE Korean Steakhouse to partnering with wine bars across New York City, Jennifer has carved her own path with Club Soda — a proof of concept that Chinese dishes and natural wine can be a perfect match. In this episode, Jennifer shares what motivated her to pursue a career in food, how she pushed herself to create original dishes, and the lessons she’s learned...

If you visit Puerto Rico, chances are you'll find yourself exploring the breathtaking El Yunque rainforest. And if you're there, you'll likely go on one of the waterfall hikes that have become a must-do experience. But these adventure tours didn't exist until just 5-6 years ago, when a few local companies began offering immersive outdoor experiences to travelers. Among the pioneers is Spotin, foun...

From in-house designer to cofounder of Koi Studios, Anyi has never shied away from taking risks - including sponsoring herself as a foreigner working in the U.S. What started as juggling client needs, design work, and even accounting has evolved into her leading business development at the company. In this episode, Anyi opens up about the realities of entrepreneurship, her hot take on AI in design...

As a firm believer in the power of compounding, Ryan began managing money for his family and friends at the age of 25. But in the early days, his fund lost more than 30% in just two quarters. In this episode, Ryan shares how he pushed through those tough times and stayed laser-focused on research. Three years later, his strategy has paid off - he’s outperformed the market by more than 70%. He also...