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 to members, and built a growing community of artists, entrepreneurs, and neighbors.

In this episode, we talk about the power of showing up - how consistency became the foundation for trust, belonging, and community. Miles shares why he left a conventional career, what he learned from serving tea every day for a month, and how The Tea Stand balances its mission with financial sustainability.

Miles didn't ignore sustainability forever, but he also didn't let the absence of a business model stop him from pursuing an idea whose value couldn't be measured on day one.

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, documenting the entrepreneurial journey in public through podcasting, and why curiosity and playfulness lead to richer experiences.

Beyond intentional travel, one thing Leeah said really stuck with me: "You'll have the highest high of your life and the lowest low of your life within 20 minutes of each other." It's one of the most honest descriptions of entrepreneurship I've heard and exactly why she started documenting her journey in public.

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 time since the 19th century, tariffs became a major revenue pillar again. More and more companies have to adapt the global supply chain reset, and SourceReady is built to navigate through it.

We talked about his journey from dropping out of UC Berkeley to becoming a serial founder, his experience of building in the ecosystems in China and the U.S, the challenges and opportunities in the global supply chain landscape, and what businesses should expect as trade policies and tariffs continue to evolve.

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.

She also opens up about rejecting preachy sustainability marketing, cutting through industry misinformation, and building a performance-driven brand without selling out - all while balancing motherhood and leadership.

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 each other’s strengths along the way.

We dive into:

• Operational bottlenecks in home health care and how AI can help
• The co-founder dynamic: how different expertise drives early-stage growth
• The early days of Claim Health and the key decisions that shaped its trajectory
• Market opportunities and the impact of healthcare policy changes

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 untangling an inherited codebase and finding the right partner to build alongside.

• Taking over a company you didn’t found
• Building vs. operating an existing business
• Lessons carried forward from Trevor's first startup
• How lawyers worked before Olive Legal and what changes after
• Designing tools that support, not replace, legal professionals
• Hiring a CEO as a technical founder
• Measuring success through retention and real usage

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 business model, from defining the ideal customer profile to balancing one-off projects with long-term collaborations, and shares their view on the future of AI in marketing.

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 matters and shares her long-term vision for Neptune as the company expands its services.

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 healthcare delivery through drone technology. We also touched on the future of drone delivery, the competitive landscape, and Brian's personal growth as an entrepreneur.